DE10129856A1 - Selective herbicides based on pyrimidine derivatives - Google Patents
Selective herbicides based on pyrimidine derivativesInfo
- Publication number
- DE10129856A1 DE10129856A1 DE2001129856 DE10129856A DE10129856A1 DE 10129856 A1 DE10129856 A1 DE 10129856A1 DE 2001129856 DE2001129856 DE 2001129856 DE 10129856 A DE10129856 A DE 10129856A DE 10129856 A1 DE10129856 A1 DE 10129856A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chloro
- phenyl
- ethyl
- methoxy
- 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.)
- Withdrawn
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 31
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 5
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 32
- 244000038559 crop plants Species 0.000 claims abstract description 10
- -1 cyano, phenyl Chemical group 0.000 claims description 140
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 24
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 22
- 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 claims description 22
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 22
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 22
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 22
- 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 22
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 20
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 20
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 20
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 19
- 239000013543 active substance Substances 0.000 claims description 19
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 19
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 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 16
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 16
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 16
- 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 compound C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 16
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 16
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical compound S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 16
- 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 description 15
- 239000005562 Glyphosate Substances 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims description 15
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 claims description 15
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 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 13
- 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 13
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
- 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 description 13
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 claims description 13
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 12
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical compound N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 claims description 12
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 12
- OHZCQCALUWOZIW-UHFFFAOYSA-N 1-[4-methoxy-6-(trifluoromethoxy)-1,3,5-triazin-2-yl]-3-[2-(trifluoromethyl)phenyl]sulfonylurea Chemical compound FC(F)(F)OC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 OHZCQCALUWOZIW-UHFFFAOYSA-N 0.000 claims description 11
- 239000003666 Amidosulfuron Substances 0.000 claims description 11
- 239000005484 Bifenox Substances 0.000 claims description 11
- 239000005529 Florasulam Substances 0.000 claims description 11
- 239000005558 Fluroxypyr Substances 0.000 claims description 11
- 239000005566 Imazamox Substances 0.000 claims description 11
- 239000005582 Metosulam Substances 0.000 claims description 11
- 239000005583 Metribuzin Substances 0.000 claims description 11
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 11
- 239000005618 Sulcotrione Substances 0.000 claims description 11
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 11
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 claims description 11
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims description 11
- MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 claims description 10
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005629 Tritosulfuron Substances 0.000 claims description 10
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 claims description 10
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 10
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 10
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims description 10
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 9
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 9
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 9
- MZZBPDKVEFVLFF-UHFFFAOYSA-N Cyanazine Natural products CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 9
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 9
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229940097068 glyphosate Drugs 0.000 claims description 9
- 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 9
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 claims description 8
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 claims description 8
- MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 claims description 8
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000005489 Bromoxynil Substances 0.000 claims description 8
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 8
- 239000005507 Diflufenican Substances 0.000 claims description 8
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 8
- 239000005531 Flufenacet Substances 0.000 claims description 8
- 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 8
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 claims description 8
- 239000005577 Mesosulfuron Substances 0.000 claims description 8
- 239000005596 Picolinafen Substances 0.000 claims description 8
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 8
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims description 8
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 claims description 8
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical group C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 claims description 8
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 claims description 8
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 8
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 claims description 8
- 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 claims description 8
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229940100389 Sulfonylurea Drugs 0.000 claims description 7
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims description 7
- 235000013877 carbamide Nutrition 0.000 claims description 7
- FFCCBBNQPIMUJI-UHFFFAOYSA-N methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-para-toluate Chemical compound COC(=O)C1=CC=C(C)C=C1C1=NC(C)(C(C)C)C(=O)N1 FFCCBBNQPIMUJI-UHFFFAOYSA-N 0.000 claims description 7
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical compound C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 claims description 7
- 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 claims description 6
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
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- IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 0.000 claims description 5
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 claims description 5
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- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 claims description 4
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- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004094 surface-active agent Substances 0.000 description 1
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- HOWHQWFXSLOJEF-MGZLOUMQSA-N systemin Chemical compound NCCCC[C@H](N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)OC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]2N(CCC2)C(=O)[C@H]2N(CCC2)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)N)C(C)C)CCC1 HOWHQWFXSLOJEF-MGZLOUMQSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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
Die Erfindung betrifft neue herbizide, synergistische Wirkstoffkombinationen bestehend aus zumindest drei Mischpartnern, die aus bekannten Pyrimidin-Derivaten einerseits und bekannten, herbizid wirksamen Verbindungen sowie gegebenenfalls Safenern andererseits bestehen und mit besonders gutem Erfolg zur selektiven Unkrautbekämpfung in verschiedenen Nutzpflanzenkulturen verwendet werden können. The invention relates to new herbicidal, synergistic combinations of active ingredients consisting of at least three mixed partners, the known pyrimidine derivatives on the one hand and known, herbicidally active compounds and, if appropriate On the other hand, safeners exist and are particularly successful at selective Weed control can be used in various crops.
Pyrimidin-Derivate sind als breit wirksame Herbizide Gegenstand einer Reihe von Patentanmeldungen (vgl. US 4 906 285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4 427 437). Die bekannten Pyrimidin-Derivate weisen jedoch eine Reihe von Wirkungslücken auf. Die Verträglichkeit dieser Verbindungen gegenüber Kulturpflanzen ist ebenfalls nicht unter allen Bedingungen ganz zufriedenstellend. Pyrimidine derivatives are the subject of a number of broad-spectrum herbicides Patent applications (cf. US 4 906 285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4,427,437). The known pyrimidine derivatives, however, have a number of Impact gaps. The tolerability of these compounds Cultivated plants are also not entirely satisfactory under all conditions.
Überraschenderweise wurde nun gefunden, dass eine Reihe von bekannten Wirkstoffen aus der Reihe der Phenoxypyrimidin-Derivate bei gemeinsamer Anwendung mit bekannten herbizid wirksamen Verbindungen aus verschiedenen Stoffklassen ausgesprochen synergistische Effekte hinsichtlich der Wirkung gegen Unkräuter zeigen und besonders vorteilhaft als breit wirksame Kombinationspräparate zur selektiven Bekämpfung von Unkräutern in verschiedenen Nutzpflanzenkulturen wie z. B. in Soja, Kartoffeln, Mais oder Reis und insbesondere in Getreide, wie z. B. Gerste, Roggen, Triticale und besonders Weizen, verwendet werden können. Surprisingly, it has now been found that a number of known active ingredients from the series of phenoxypyrimidine derivatives when used together with known herbicidally active compounds from various classes of substances show pronounced synergistic effects with regard to the action against weeds and particularly advantageous as a broadly effective combination preparation for selective Control of weeds in various crops such as B. in soy, Potatoes, corn or rice and especially in cereals, such as. B. barley, rye, Triticale and especially wheat, can be used.
Überraschenderweise wurde ebenfalls gefunden, dass die Phenoxypyrimidin-Derivate
zusammen mit anderen, bevorzugt zwei weiteren bekannten herbizid wirksamen
Verbindungen bei gemeinsamer Anwendung, gegebenenfalls mit den im Weiteren
beschriebenen, die Kulturpflanzenverträglichkeit verbessernden Verbindungen
(Safenern/Antidots) besonders vorteilhaft als breit wirksame Kombinationspräparate
zur selektiven Bekämpfung von Unkräutern in Nutzpflanzenkulturen wie Getreide, so
z. B. Weizen, Gerste, Roggen und Reis, aber auch in Mais verwendet werden können.
Gegenstand der Erfindung sind selektiv-herbizide Mittel, gekennzeichnet durch einen
wirksamen Gehalt an einer Wirkstoftkombination umfassend
- a) zumindest ein Phenoxypyrimidin-Derivat der allgemeinen Formel (I)
in welcher
R für Wasserstoff, -CH2CH2S(O)nR1 (wobei R1 für C1-C4-Alkyl und n für 0, 1 oder 2 steht) oder
steht,
wobei
R2 für Wasserstoff, Halogen, Cyano, Phenyl, C1-C8-Alkyl, C1-C4- Alkoxy, C1-C4-Alkylthio, C1-C4-Alkoxycarbonyl, Mono- oder Di-C1-C4-Alkylaminocarbonyl, Phenyl-C1-C4 -Alkylaminocarbonyl steht, wobei die Phenylgruppe gegebenenfalls durch Halogen, C1-C2-Alkyl oder C1-C2-Alkoxy, Furylmethylaminocarbonyl oder Phenyl substituiert sein kann, und
R3 für jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1- C4-Alkyl, C1-C4-Alkoxy oder Allyloxy substituiertes Phenyl, für gegebenenfalls durch C1-C4-Alkyl, Phenoxy, Benzyloxy oder Acetoxy substituiertes Amino, für C1-C4-Alkylthio oder für die Gruppierung -COR4 steht, wobei R4 für C1-C4-Alkoxy, C1- C4-Alkyl, Benzyloxy oder Benzylamino steht,
A für Chlor oder Methoxy steht und
D und E, die gleich oder unterschiedlich sein können, für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Alkoxy oder durch Halogen substituiertes C1-C8- Alkoxy stehen,
und/oder einem Salz einer Verbindung der Formel (I)
("Wirkstoffe der Gruppe 1"),
und - b) zumindest eine Verbindung aus einer weiteren Gruppe von Herbiziden, welche
die nachstehend genannten Wirkstoffe enthält:
Methyl-2-[[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazonesodium) der Formel
und
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)phenyl]sulfonyl]-1H-1,2,4-triazol-1-carboxamid, Natrium-Salz (Flucarbazone-sodium) der Formel
("Wirkstoffe der Gruppe 2"),
sowie - c) einer oder mehrerer Verbindungen aus einer weiteren Gruppe von Herbiziden,
welche die nachstehend genannten Wirkstoffe enthält:
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-Natriumsalz (Acifluorfen-sodium), 2-Chlor-6-nitro-3-phenoxybenzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethyl-phenyl)-acetamid (Alachlor), N-Ethyl-N'-i-propyl-6-methylthio-1,3,5-triazin-2,4-diamin (Ametryn), 4-Amino-N-(1,1-Dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-1H- 1,2,4-triazol-1-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), 1H-1,2,4-Triazol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(1-isopropyl)- amino]-2-oxo-ethyl]-O,O-dimethyl-phosphorodithioate (Anilofos), 6-Chlor-4- ethylamino-2-isopropylamino-1,3,5-triazin (Atrazin), 2-[2,4-Dichlor-5-(2- propinyloxy)-phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)- on (Azafenidin), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-[1-methyl-4-(2- methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-ylsulfonyl]-harnstoff (Azimsulfuron), N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4- Chlor-2-oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6- dinitro-4-trifluormethyl-benzenamin (Benfluralin), 2,3-Dihydro-3,3-dimethyl- 5-benzofuranylethansulfonat (Benfuresate), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuronmethyl), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thiobencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1(2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-on (Benzobicyclon), 2-[[4-(2,4-Dichlor-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]-oxy]-1-(4-methyl-phenyl)-ethanon (Benzofenap), Ethyl N-benzoyl-N-(3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-1H-2,1,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 5- Brom-6-methyl-3-(1-methyl-propyl)-2,4(1H,3H)pyrimidindion (Bromacil), 2- Brom-3,3-dimethyl-N-(1-methyl-1-phenyl-ethyl)-butanamid (Bromobutide), 3,5-Dibrom-4-hydroxy-benzaldehyd-O-(2,4-dinitro-phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), N-Butoxymethyl-2- chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2-Chlor-5-(3,6-dihydro-3- methyl-2,6-dioxo-4-trifluormethyl-1(2H)-pyrimidinyl)-benzoesäure-[1,1-dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(1-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxo-butyl)-phenyl]-2-cyclohexen-1-on (Butroxydim), S-Ethyl-bis-(2-methyl-propyl)-thiocarbamat (Butylate), N,N-Diethyl-3-(2,4,6-trimethyl-phenylsulfonyl)-1H-1,2,4-triazol-1- carboxamid (Cafenstrole), 2-[1-[(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3- hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)- phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-1-(3-methoxy-4-nitro-phenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6- methoxy-pyrimidin-2-yl)-N'-(2-ethoxycarbonyl-phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), 1,3,5-Trichlor-2-(4-nitro-phenoxy)-benzol (Chlornitrofen), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)- harnstoff (Chlorsulfuron), N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo- 2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl), Exo-1- methyl-4-isopropyl-2-(2-methyl-phenyl-methoxy)-7-oxabicyclo-[2.2.1]- heptan (Cinmethylin), N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenylsulfonyl)-harnstoff (Cinosulfuron), 2-[1-[2-(4-Chlorphenoxy)-propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexandion (Clefoxydim), (E,E)-(+)-2-[1-[[(3-Chlor-2-propenyl)-oxy]-imino]- propyl]-3-hydroxy-2-cyclohexen-1-on (Clethodim), (R)-(2-Propinyl)-2-[4-(5- chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 2-(2,4-Dichlor-3-methyl-phenoxy)-N-phenyl-propanamid (Clomeprop), 3,6- Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5-ethoxy-7- fluor[1,2,4]triazolo[1,5-c]pyrimidin-2-yl-sulfonyl)-amino]-benzoat (Cloransulam-methyl), N-[(2-Chlor-phenyl)-methyl]-N'-(1-methyl-1-phenyl-ethyl)- harnstoff (Cumyluron), 2-Chlor-4-ethylamino-6-(1-cyano-1-methyl-ethylamino)-1,3,5-triazin (Cyanazine), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2- cyclopropylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(1- Ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen- 1-on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propansäure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor- [1,2,4]-triazolo-[1,5-c]-pyrimidin-2-sulfonamid (Diclosulam), 1,2-Dimethyl- 3,5-diphenyl-1H-pyrazolium-methylsulfat (Difenzoquat), N-(2,4-Difluorphenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), 2-[1-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3-carbonsäure (Diflufenzopyr), S-(1-Methyl-1-phenyl-ethyl)-1-piperidin-carbothioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-methoxyethyl)-acetamid (Dimethachlor), N-(1,2-Dimethyl-propyl)-N'-ethyl-6-methylthio-1,3,5-triazin-2,4-diamin (Dimethametryn), (S-)2-Chlor-N-(2,4-dimethyl- 3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamid (S-) (Dimethenamid), 2- Amino-4-(1-fluor-1-methyl-ethyl)-6-(1-methyl-2-(3,5-dimethyl-phenoxy)- ethylamino)-1,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl-1,3-diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[1,2- a:2',1'-c]pyrazindiium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6- trifluormethyl-pyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlorphenyl)-N,N-dimethyl-harnstoff (Diuron), N-(4-Methyl-phenyl)-N'-(1- methyl-1-phenyl-ethyl)-harnstoff (Dymron, Daimuron), 2-[2-(3-Chlorphenyl)-oxiranylmethyl]-2-ethyl-1H-inden-1,3(2H)-dion (Epropodan), S- Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N-(1,2-dimethyl-propyl)-thiocarbamat (Esprocarb), N-Ethyl-N-(2-methyl-2-propenyl)- 2,6-dinitro-4-trifluormethyl-benzenamin (Ethalfluralin), (S)-(2-Ethoxy-1- methyl-2-oxoethyl)-2-chlor-5-(2-chlor-4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), N-(2,3-Dichlor-phenyl)-4-ethoxymethoxybenzamid (Etobenzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N- ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L-alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)-DL- alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy- [1,2,4]-triazolo-[1,5-c]-pyrimidin-2-sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure-butylester (Fluazifop, -butyl, -P-butyl), 5-(4-Brom-1-methyl-5-trifluormethyl-1H-pyrazol-3-yl)-2- chlor-4-fluor-benzoesäure-i-propylester (Fluazolate), 4,5-Dihydro-3-methoxy- 4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-1-H-1,2,4-triazol-1- carboxamid-Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)-N-i- propyl-2-(5-trifluormethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), N-(2,6-Difluor-phenyl)-5-methyl-1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Flumetsulam), Pentyl-[2-chlor-4-fluor-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4- dihydro-3-oxo-4-(2-propinyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro- 1H-isoindol-1,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(1-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-1H-isoindol-1,3(2H)-dion (Flumipropyn), 3-Chlor-4-chlormethyl-1-(3-trifluormethyl-phenyl)-2-pyrrolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), 1-(4-Chlor-3- (2,2,3,3,3-pentafluor-propoxymethyl)-phenyl)-5-phenyl-1H-1,2,4-triazol-3- carboxamid (Flupoxam), 1-Isopropyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-1(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2- yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 9- Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor-6-fluorpyridin-2-yl-oxy)-essigsäure (-2-butoxy-1-methyl-ethylester, -1-methylheptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl- 4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4- fluor-5-(tetrahydro-3-oxo-1H,3H-[1,3,4]-thiadiazolo-[3,4-a]-pyridazin-1- yliden)-amino-phenyl]-thioacetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl-phenoxy)-N-methylsulfonyl-2-nitro-benzamid (Fomesafen), 2- [[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4- formylamino-N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4- (hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluormethylpyridin-2-yl-oxy)-phenoxy]-propansäure (-methylester, -2-ethoxy-ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-Cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazin-2,4(1H,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)- 4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-iso- propyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5- methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethylpyridin-3-carbonsäure (Imazethapyr), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'- (2-chlor-imidazo[1,2-a]-pyridin-3-yl-sulfonyl)-harnstoff (Imazosuliron), N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N' -(5-iod-2-methoxycarbonylphenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 4- Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl-N'-(4-isopropylphenyl)-harnstoff (Isoproturon), N-(3-(1-Ethyl-1-methyl-propyl)-isoxazol-5- yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methylsulfonyl-phenyl)- (5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5-Cyclopropylisoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)-methanon (Isoxaflutole), 2-[2-[4-[3,5-Dichlor-2-pyridinyl)-oxy]-phenoxy]-1-oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Ethoxy-1-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoat (Lactofen), N'-(3,4-dichlor-phenyl)-N- methoxy-N-methyl-harnstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2- (2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6- Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 2-(4- Methylsulfonyl-2-nitro-benzoyl)-1,3-cyclohexandion (Mesotrione), 4-Amino- 3-methyl-6-phenyl-1,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(1 H-pyrazol-1-yl-methyl)-acetamid (Metazachlor), N'-(4- (3,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)- phenyl)-N-methoxy-N-methyl-harnstoff (Metobenzuron), N'-(4-Bromphenyl)-N-methoxy-N-methylharnstoff (Metobromuron), (S)-2-Chlor-N-(2- ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methyl-ethyl)-acet-amid (Metolachlor, S-Metolachlor), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- 1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4- methoxy-phenyl)-N,N-dimethyl-harnstoff (Metoxuron), 4-Amino-6-tertbutyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-1H-azepin-1-carbothioat (Molinate), 2-(2-Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N-Butyl-N'- (3,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfuron), 4-Chlor-5-methylamino-2-(3-trifluormethyl-phenyl)-3(2H)pyridazinon (Norflurazon), S-(2-Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4-Dipropylamino-3,5-dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-on (Oxadiargyl), 3-[2,4-Dichlor-5-(1-methyl-ethoxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2-yl)-N'-(2-oxetan- 3-yl-oxycarbonyl-phenylsulfonyl)-harnstoff (Oxasulfuron), 3-[1-(3,5-Dichlorphenyl)-1-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-on (Oxaziclomefone), 2-Chlor-1-(3-ethoxy-4-nitro-phenoxy)-4-trifluormethylbenzen (Oxyfluorfen), 1,1'-Dimethyl-4,4'-bipyridinium (Paraquat), 1-Amino- N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t- Butyl)-N-(1-ethyl-propyl)-2,6-dinitro-benzenamin (Pendralin), 3-(4-Chlor-5- cyclopentyloxy-2-fluor-phenyl)-5-(1-methyl-ethyliden)-2,4-oxazolidin-dion (Pentoxazone), 4-Amino-3,5,6-trichlor-pyridin-2-carbonsäure (Picloram), N- (4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2-carboxamid (Picolinafen), S-[2-(2-Methyl-1-piperidinyl)-2-oxo-ethyl]-O,O-dipropyl-phosphorodithioat (Piperophos), 2-Chlor-N-(2,6-diethyl-phenyl)-N-(2-propoxyethyl)-acetamid (Pretilachlor), N-(4,6-Bis-difluormethoxy-pyrimidin-2-yl)- N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Primisulfuron-methyl), 1- Chlor-N-[2-chlor-4-fluor-5-[(6S,7aR)-6-fluor-tetrahydro-1,3-dioxo-1H- pyrrolo[1,2-c]imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Profluazol), 2- Chlor-N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlor-phenyl)- propanamid (Propanil), (R)-[2-[[(1-Methyl-ethyliden)-amino]-oxy]-ethyl]-2- [4-(6-chlor-2-chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2- Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[(1-methyl-ethoxy)-methyl]-acetamid (Propisochlor), 2-[[[(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)-carbonyl]-amino]-sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazone-sodium), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Prosulfocarb), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluor-propyl)-phenylsulfonyl)-harnstoff (Prosulfuron), Ethyl-[2-Chlor-5-(4- chlor-5-difluormethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 1-(3-Chlor-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-2- yl)-5-(methyl-2-propinylamino)-1H-pyrazol-4-carbonitril (Pyraclonil, Pyrazogyl), 4-(2,4-Dichlor-benzoyl)-1,3-dimethyl-5-(4-methyl-phenylsulfonyloxy)- pyrazol (Pyrazolate), 4-(2,4-Dichlor-benzoyl)-1,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenylmethanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2- yl-oxy)-benzoyl]-oxim (Pyribenzoxim), O[3-(1,1-Dimethyl-ethyl)-phenyl]-(6- methoxy-2-pyridinyl)-methylthiocarbamat (Pyributicarb), 6-Chlor-3-phenyl- 4-pyridazinol (Pyridafol), O-(6-Chlor-3-phenyl-pyridazin-4-yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl-1(3H)-isobenzofuranon (Pyriftalid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)-benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-ylthio)-benzoesäure- Natriumsalz (Pyrithiobacsodium), 3,7-Dichlor-chinolin-8-carbonsäure (Quinchlorac), 7-Chlor-3-methyl-chinolin-8-carbonsäure (Quinmerac), 2-[4-(6- Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, -tetrahydro-2- furanyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfuron), 2-(1-Ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2- cyclohexen-1-on (Sethoxydim), 6-Chlor-2,4-bisethylamino-1,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Sulfentrazone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]- benzoate (Sulfometuron-methyl), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[1,2-a]pyridin-3-sulfonamid (Sulfosuliron), 6-Chlor-4- ethylamino-2-tertbutylamino-1,3,5-triazin (Terbuthylazine), 2-tert-Butylamino-4-ethylamino-6-methylthio-1,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6- dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluormethyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6- dimethyl-3H,5H-pyrrolo[2,1-c]-1,2,4-thiadiazol-3-ylidenamino)-7-fluor-4-(2- propinyl)-2H-1,4-benzoxazin-3(4H)-on (Thidiazimin), N-(4-Methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen-1-on (Tralkoxydim), S-(2,3,3-Trichlor-2- propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl- 1,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulf uron), N-Methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)- pyridin-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2-trichlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]- carbonyl]-3-(2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), 1-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-1,3,5-triazin-2- yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfuronmethyl), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), N-[[(4,6-Dimethoxy-2- pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulfonyl-amino])-2- pyridinsulfonamid, (vgl. WO-A-92/10660), 4-[4,5-Dihydro-4-methyl-5-oxo- (3-trifluormethyl)-1H-1,2,4-triazol-1-yl]-2-((ethylsulfonyl)amino]-5-fluorbenzencarbothioamid (vgl. WO-A-95/30661), Phenylcarbothiamid-,4-[4,5- dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H-1,2,4-triazol-1-yl]-2- ((ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991) und 2-Chloro-N-[1-[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-1H- pyrazol-5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599).
("Wirkstoffe der Gruppe 3"),
sowie gegebenenfalls zusätzlich - d) zumindest eine die Kulturpflanzen-Verträglichkeit verbessernde Verbindung
aus der folgenden Gruppe von Verbindungen:
α-(1,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), α-(Cyanomethoximino)-phenylacetonitril (Cyometrinil), 4-Chlor-N-(1,3-dioxolan-2- yl-methoxy)-α-trifluor-acetophenonoxim (Fluxofenim), 4,6-Dichlor-2-phenylpyrimidin (Fenclorim), 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin (Benoxacor), 5-Chlor-chinoxalin-8-oxy-essigsäure-(1-methyl-hexylester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N- (2-propenyl)-acetamid (DKA-24), 1,8-Naphthalsäureanhydrid, 1-(2,4-Dichlor-phenyl)-5-trichlormethyl-1H-1,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäure-phenylmethylester (Flurazole), 3-Dichloracetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (Furilazole, MON-13900), 4-Dichloracetyl-1-oxa-4-aza-spiro[4.5]-decan (AD-67), 2-Dichlormethyl-2-methyl-1,3-dioxolan (MG-191), 2,2-Dichlor-N- (1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamid (PPG-1292), 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-(1- methyl-1-phenyl-ethyl)-harnstoff (Dymron), 1-Dichloracetyl-hexahydro- 3,3,8atrimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-on (BAS-145138), N-(2- Methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl- 4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), (4-Chlor- 2-methylphenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methylphenoxy)-propionsäure (Mecoprop), Diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl- 1H-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate
("Wirkstoffe der Gruppe 4").
- a) at least one phenoxypyrimidine derivative of the general formula (I)
in which
R is hydrogen, -CH 2 CH 2 S (O) n R 1 (where R 1 is C 1 -C 4 alkyl and n is 0, 1 or 2) or
stands,
in which
R 2 represents hydrogen, halogen, cyano, phenyl, C 1 -C 8 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, phenyl-C 1 -C 4 -alkylaminocarbonyl, where the phenyl group may optionally be substituted by halogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy, furylmethylaminocarbonyl or phenyl, and
R 3 for phenyl optionally substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or allyloxy, for amino optionally substituted by C 1 -C 4 alkyl, phenoxy, benzyloxy or acetoxy stands for C 1 -C 4 alkylthio or for the grouping -COR 4 , where R 4 stands for C 1 -C 4 alkoxy, C 1 - C 4 alkyl, benzyloxy or benzylamino,
A represents chlorine or methoxy and
Are alkoxy, - D, which may be the same or different, is hydrogen, halogen, C 1 -C e, 8 alkyl, C 1 -C 8 alkoxy or halogen-substituted C 1 -C 8
and / or a salt of a compound of formula (I)
("Active substances of group 1"),
and - b) at least one compound from a further group of herbicides which contains the active compounds mentioned below:
Methyl 2 - [[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino] sulfonyl] benzoic acid, sodium Salt (propoxycarbazone sodium) of the formula
and
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [[2- (trifluoromethoxy) phenyl] sulfonyl] -1H-1,2,4-triazole-1-carboxamide, sodium salt ( Flucarbazone-sodium) of the formula
("Active substances of group 2"),
such as - c) one or more compounds from a further group of herbicides which contains the active compounds mentioned below:
2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid sodium salt (Acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxybenzenamine (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor), N- Ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine-2,4-diamine (Ametryn), 4-Amino-N- (1,1-dimethyl-ethyl) -4,5- dihydro-3- (1-methyl-ethyl) -5-oxo-1H-1,2,4-triazole-1-carboxamide (amicarbazone), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1,2,4-triazol-3-amine (amitrole), S- [2 - [(4-chlorophenyl) - (1-isopropyl) - amino] -2-oxo-ethyl] -O, O-dimethyl-phosphorodithioate (anilofos), 6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2,4-triazolo- [4,3-a] pyridine-3 ( 2H) - one (azafenidin), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) -1H- pyrazol-5-ylsulfonyl] -harnsto ff (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl- N-ethyl-2,6-dinitro-4-trifluoromethylbenzamine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulfonate (benfuresate), N- (4,6-dimethoxypyrimidine-2 - yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuronmethyl), S - [(4-chlorophenyl) methyl] diethylthiocarbamate (benthiocarb, thiobencarb), 2- [2- [4- ( 3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinylphenoxymethyl] -5-ethyl-phenoxypropanoic acid methyl ester (benzfendizone), 3- (2-chloro-4- methylsulfonyl-benzoyl) -4-phenylthio-bicyclo- [3.2.1] oct-3-en-2-one (benzobicyclone), 2 - [[4- (2,4-dichloro-3-methylbenzoyl) -1, 3-dimethyl-1H-pyrazol-5-yl] -oxy] -1- (4-methylphenyl) ethanone (benzofenap), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL- alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) -2-nitro - benzoate (bifenox), 5-bromo-6-methyl-3- (1-methyl-propyl) -2.4 (1H, 3H) pyrimidinedione (bromoacil), 2-bromo-3,3-dimethyl-N- (1st -methyl-1-phenyl-ethyl) -butanamide (bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) -oxime (bromofenoxime), 3,5-dibromo- 4-hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2,6-diethyl-phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl -2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid- [1,1-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3- (1-oxo-butyl) phenyl] -2-cyclohexen-1-one (butroxydim), S-ethyl bis (2-methyl-propyl) -thiocarbamate (butylate), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) -1H-1,2,4-triazole-1-carboxamide ( Cafenstrole), 2- [1 - [(3-chloro-2-propenyl) oxyimino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1 -one (caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) phenyl) -4-difluoromethyl-5-methyl-2, 4-dihydro-3H-1,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-1- (3-methoxy-4-nitro-phenoxy) -benzene (chloromethoxyfen), 3- Amino-2,5-dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) urea (chlorimuron-ethyl), 1 , 3,5-trichloro-2- (4-nitro-phenoxy) benzene (chloronitrofen), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- ( 2-chlorophenylsulfonyl) urea (chlorosulfuron), N '- (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlorotoluron), 2-chloro-3- [2-chloro-5 - (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), exo-1-methyl -4-isopropyl-2- (2-methyl-phenyl-methoxy) -7-oxabicyclo- [2.2.1] heptane (cinmethylin), N- (4,6-dimethoxy-1,3,5-triazine-2 -yl) -N '- (2- (2-methoxy-ethoxy) phenylsulfonyl) urea (cinosulfuron), 2- [1- [2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H- thiopyran-3-yl) -1,3-cyclohexanedione (clefoxydim), (E, E) - (+) - 2- [1 - [[(3-chloro-2-propenyl) -oxy] -imino] - propyl ] -3-hyd roxy-2-cyclohexen-1-one (clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate ( Clodinafop-propargyl), 2- (2,4-dichloro-3-methyl-phenoxy) -N-phenyl-propanamide (Clomeprop), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralide), methyl-3-chloro -2 - [(5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) amino] benzoate (chlorosulam-methyl), N - [( 2-chlorophenyl) methyl] -N '- (1-methyl-1-phenyl-ethyl) urea (cumyluron), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino ) -1,3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 2- (1- Ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen- 1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluoro- phenoxy) -phenoxy] -propanoic acid-butyl ester (cyhalofop-butyl), 2,4-dichloro-phenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -2 - (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenox y) -phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro [1,2,4] triazolo- [1,5-c] -pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium-methylsulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (diflufenican), 2- [1 - [(3,5-difluoro-phenyl) -amino-carbonyl-hydrazono] -ethyl] -pyridine-3-carboxylic acid (diflufenzopyr), S- (1- Methyl 1-phenyl-ethyl) -1-piperidine-carbothioate (dimepiperate), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (2-methoxyethyl) -acetamide (dimethachlor), N- ( 1,2-dimethyl-propyl) -N'-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine (dimethametryn), (S-) 2-chloro-N- (2,4- dimethyl-3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-methyl-2- (3,5-dimethyl-phenoxy) ethylamino) -1,3,5-triazine (dimexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3 -diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2- a: 2 ', 1'-c] pyrazinediium (diquat), S, S-dimethyl-2-dif luormethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl-urea (diuron), N- (4- Methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron, Daimuron), 2- [2- (3-chlorophenyl) -oxiranylmethyl] -2-ethyl-1H-inden-1 , 3 (2H) -dione (epropodane), S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Esprocarb), N-ethyl -N- (2-methyl-2-propenyl) - 2,6-dinitro-4-trifluoromethylbenzamine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro 5- (2-chloro-4-trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (ethoxysulfuron) , N- (2,3-dichlorophenyl) -4-ethoxymethoxybenzamide (etobenzanide), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate ( Fenoxaprop- (P) -ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl- N-benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate ( Flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4 -fluorophenoxy) -DL- alaninate (flamprop-methyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [1,5- c] pyrimidine-2-sulfonamide (florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) phenoxy] propanoic acid butyl ester (fluazifop, butyl, -P- butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), 4,5-dihydro- 3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1-H-1,2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N - (4-Fluoro-phenyl) -nipropyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (Flufenacet), N- (2,6-difluorophenyl ) -5-methyl-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), pentyl- [2-chloro-4-fluoro-5- (1,3,4, 5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro-3-oxo 4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5- [(1-methyl-2-propynyl) -oxy] phenyl] -4,5,6,7-tetrahydro-1H-isoindole-1,3 (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl -1- (3-trifluoromethyl-phenyl) -2-pyrrolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1- (4- Chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2- chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidyl) benzoate (flupropacil), N- (4,6-dimethoxy pyrimidine-2 -yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol) , (4-Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methylheptyl ester) (fluroxypyr, -butoxypropyl, -meptyl) , 5-methylamino-2-phenyl-4- (3-trifluorme thylphenyl) -3 (2H) -furanone (Flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1,3,4] -thiadiazolo- [3,4-a] pyridazin-1-ylidene) amino-phenyl] thioacetate (fluthiacet-methyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) -N-methylsulfonyl-2-nitro-benzamide (Fomesafen), 2- [[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N-dimethyl-benzamide (foramsulfuron), 2 -Amino-4- (hydroxymethylphosphinyl) -butanoic acid (-ammonium salt) (glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium), (R) -2- [4- (3rd -Chlor-5-trifluoromethylpyridin-2-yl-oxy) -phenoxy] -propanoic acid (-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-Cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4 (1H, 3H) -dione (Hexazinone), methyl-2- (4,5-dihydro-4-methyl-4 -isopropyl-5-oxo-1H-imidazol-2-yl) - 4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo 1 H -imidazo l-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) - 5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquin ), 2- (4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) -5-ethylpyridine-3-carboxylic acid (imazethapyr), N- (4, 6-Dimethoxy-pyrimidin-2-yl) -N'- (2-chloro-imidazo [1,2-a] -pyridin-3-yl-sulfonyl) urea (imazosulirone), N- (4-methoxy-6 -methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonylphenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodo- benzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3- (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2 , 6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropylisoxazol-4-yl) - ( 2-methylsulfonyl-4-trifluoromethylphenyl) methanone (isoxaflutole), 2- [2 - [4- [3,5-dichloro-2-pyridinyl) oxy] phenoxy] -1-oxo-propyl] isoxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2-oxo-ethyl) - 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3,4-dichlorophenyl) -N-methoxy-N-methyl-urea (Linuron), ( 4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl -acetamide (Mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid -methyl ester (mesosulfuron), 2- (4-methylsulfonyl-2-nitro-benzoyl) -1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-1,2,4-triazine-5 (4H) -one (metamitron), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (1 H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N '- (4th - (3,4-Dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy) - phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4-Bromophenyl) -N-methoxy-N-methylurea (metobromuron), (S) -2-chloro-N- (2-ethyl-6-methy l-phenyl) -N- (2-methoxy-1-methyl-ethyl) -acet-amide (metolachlor, S-metolachlor), N- (2,6-dichloro-3-methylphenyl) -5,7- dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron ), 4-Amino-6-tertbutyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1,3,5-triazine -2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-1H-azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N -phenyl-propanamide (naproanilide), N-butyl-N'- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) pyridazinone (norflurazone), p - (2-Chlorobenzyl) -N, N-diethylthiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy ) -phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3 - [2,4-dichloro-5- (1-methylethoxy) phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiazon), N- ( 4,6-Dimethyl-pyrimidin-2-yl) -N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [1- (3,5-dichlorophenyl) -1- i-propyl] -2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1- (3-ethoxy-4-nitro-phenoxy ) -4-trifluoromethylbenzene (oxyfluorfen), 1,1'-dimethyl-4,4'-bipyridinium (paraquat), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6- dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (1-ethyl-propyl) -2,6-dinitro-benzenamine (pendralin), 3- (4-chloro-5-cyclopentyloxy-2-fluorine -phenyl) -5- (1-methyl-ethylidene) -2,4-oxazolidinedione (pentoxazone), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N- (4th -Fluorophenyl) -6- (3-trifluoromethylphenoxy) pyridine-2-carboxamide (picolinafen), S- [2- (2-methyl-1-piperidinyl) -2-oxo-ethyl] -O, O -dipropyl-phosphorodithioate (Piperophos), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxyethyl) -acetamide (pretilachlor), N- (4,6-bis-difluoromethoxy-p yrimidin-2-yl) - N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), 1-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6 -fluoro-tetrahydro-1,3-dioxo-1H-pyrrolo [1,2-c] imidazole-2 (3H) -yl] -phenyl] -methanesulfonamide (profluazole), 2-chloro-N-isopropyl-N-phenyl -acetamide (propachlor), N- (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(1-methylethylidene) amino] oxy] ethyl] -2 - [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(1-methyl-ethoxy) -methyl] -acetamide (propisochlor), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] -amino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarbazone-sodium), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-methoxy-6-methyl-1,3,5- triazin-2-yl) -N '- (2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (prosulfuron), ethyl- [2-chloro-5- (4-chloro-5-difluoromethoxy -1-methyl-1H-pyrazol-3-yl) -4-fluoro-phenoxy] acetate (pyraflufen-ethyl), 1- (3-chloro-4,5,6 , 7-tetrahydro-pyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -1H-pyrazole-4-carbonitrile (pyraclonil, pyrazogyl), 4- (2,4- Dichlorobenzoyl) -1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5- (phenylcarbonylmethoxy) - pyrazole (pyrazoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenylmethanone -O- [2,6-bis- (4,6-dimethoxypyrimidin-2-yl-oxy) benzoyl] oxime (pyribenzoxime), O [3- (1,1-dimethylethyl) phenyl] - (6-methoxy-2-pyridinyl) methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O- (6-chloro-3-phenyl-pyridazin-4-yl) -S -octyl-thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 (3H ) -Isobenzofuranone (pyriftalid), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidine-2 -ylthio) -benzoic acid- sodium alz (pyrithiobacsodium), 3,7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy ) -phenoxy] -propanoic acid (-ethyl ester, -tetrahydro-2-furanyl-methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidin-2-yl ) -N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfuron), 2- (1-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1- on (Sethoxydim), 6-chloro-2,4-bisethylamino-1,3,5-triazine (simazine), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (Sulcotrione) , 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone), methyl 2 - [[[[((4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoate (sulfometuron methyl), N-phosphonomethyl glycine trimethyl sulfonium (sulfosate), N- ( 4,6-Dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3-sulfonamide (sulfosulirone), 6-chloro-4-ethylam ino-2-tertbutylamino-1,3,5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N- (2nd , 6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- ( 2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2,1-c] - 1,2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) -2H-1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy- 6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-methyl), 2- (ethoximino-propyl) -3 -hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) -diisopropylcarbamothioate (triallate), N - (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl- N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) pyridin-2-yloxy acetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloroethyl) oxirane (Tridiphane), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), 1 -Amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -1,3,5 -triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (triflusulfuronmethyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N' - (2-trifluoromethylphenylsulfonyl) urea (tritosulfuron), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino]) -2- pyridine sulfonamide, (cf. WO-A-92/10660), 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2- ( (ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide (see WO-A-95/30661), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1 , 2,4-triazol-1-yl] -2- ((ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and 2-chloro-N- [1- [2, 6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2; SLA5599).
("Active substances of group 3"),
as well as, if necessary, additionally - d) at least one compound which improves the tolerance of crop plants from the following group of compounds:
α- (1,3-Dioxolan-2-yl-methoximino) phenylacetonitrile (oxabetrinil), α- (cyanomethoximino) phenylacetonitrile (cyometrinil), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy ) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (Fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (Benoxacor), 5 Chloro-quinoxaline-8-oxyacetic acid (1-methyl-hexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2 -propenyl) -acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole -ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] decane (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N - (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichlormid) , N- ( 4-methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-3,3,8atrimethylpyrrolo [1,2-a] pyrimidine-6 ( 2H) -one (BAS-145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) benzenesulfonamide, ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl) , (4-Chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (Mecoprop), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro -5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives
("Active substances of group 4").
Bevorzugte Substituenten der in der vorstehend gezeigten Formel (I) aufgeführten
Reste werden im folgenden erläutert.
R steht bevorzugt für Wasserstoff oder
wobei
R2 bevorzugt für Wasserstoff, Chlor, Cyano, Phenyl, C1-C8-Alkyl, Methoxy,
Methylthio, C1-C2-Alkoxycarbonyl, Propylaminocarbonyl,
Dimethylaminocarbonyl, Benzylaminocarbonyl (wobei die Benzylgruppe gegebenenfalls durch
Chloro, Methyl oder Methoxy substituiert ist), 2'-Phenylethylaminocarbonyl
oder Furylmethylaminocarbonyl steht, und
R3 bevorzugt für gegebenenfalls durch Chlor, Fluor, Cyano, Nitro, Methyl,
Methoxy, Ethoxy, Butoxy, Allyloxy, Methylthio, Dimethylamino, Phenoxy,
Benzyloxy oder Acetoxy substituiertes Phenyl oder für -COR4 steht, worin
R4 für Methoxy, Ethoxy, Methyl, Benzyloxy oder Benzylamino steht,
A bevorzugt für Chlor oder Methoxy steht und
D und E, die gleich oder unterschiedlich sein können, bevorzugt für Wasserstoff,
Methoxy oder Ethoxy stehen.
R2 steht besonders bevorzugt für Wasserstoff, Methyl, Methylthio, Cyano,
Methoxycarbonyl oder Phenyl.
R3 steht besonders bevorzugt für gegebenenfalls durch Methyl oder Methoxy
substituiertes Phenyl.
A steht besonders bevorzugt für Methoxy.
D und E stehen besonders bevorzugt für Methoxy.
R2 steht ganz besonders bevorzugt für Phenyl.
R3 steht ganz besonders bevorzugt für Phenyl.
Preferred substituents of the radicals shown in the formula (I) shown above are explained below.
R preferably represents hydrogen or
in which
R 2 is preferably hydrogen, chlorine, cyano, phenyl, C 1 -C 8 alkyl, methoxy, methylthio, C 1 -C 2 alkoxycarbonyl, propylaminocarbonyl, dimethylaminocarbonyl, benzylaminocarbonyl (the benzyl group being optionally substituted by chloro, methyl or methoxy ), 2'-phenylethylaminocarbonyl or furylmethylaminocarbonyl, and
R 3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR 4 , where R 4 represents methoxy, ethoxy, Is methyl, benzyloxy or benzylamino,
A preferably represents chlorine or methoxy and
D and E, which may be the same or different, are preferably hydrogen, methoxy or ethoxy.
R 2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
R 3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
A particularly preferably represents methoxy.
D and E are particularly preferably methoxy.
R 2 very particularly preferably represents phenyl.
R 3 very particularly preferably represents phenyl.
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden eine oder
mehrere Verbindungen aus einer Gruppe von Herbiziden bevorzugt, welche die
nachstehend genannten Wirkstoffe enthält:
4-Amino-N-(1,1-Dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-1H-1,2,4-triazol-1-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-
methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), N-Benzyl-2-(4-
fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 3-i-Propyl-1H-2,1,3-
benzothiadiazin-4(3H)-on (Bentazon),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitrobenzoat (Bifenox), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 2-(4-Chlor-2-
fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), N-(4-Methoxy-6-methyl-1,3,5-
triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N'-(3-Chlor-4-
methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-
(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl),
(R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure
(Clopyralid), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure
(Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2-[4-
(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl),
1,2-Dimethyl-3,5-diphenyl-1H-pyrazolium-methylsulfat (Difenzoquat),
N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican),
N-(4,6-Dimethoxypyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysuliron), (R)-
Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-
ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-
carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-
alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L-
alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)-
DL-alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[1,2,4]-
triazolo-[1,5-c]-pyrimidin-2-sulfonamid (Florasulam), 5-(4-Brom- 1
-methyl-5-trifluormethyl-1H-pyrazol-3-yl)-2-chlor-4-fluor-benzoesäure-i-propylester (Fluazolate),
4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-1-
H-1,2,4-triazol-1-carboxamid-Natriumsalz (Flucarbazone-sodium),
N-(4-Fluorphenyl)-N-i-propyl-2-(5-trifluormethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamid
(Flufenacet),
5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl),
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz
(Flupyrsulfuron-methyl-sodium), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure
(-2-butoxy-1-methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl,
-meptyl), 5-Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-furanon
(Flurtamone), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz)
(Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz),
(Glyphosate, -isopropylammonium), Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-
oxo-1H-imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-
4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure
(Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-
methoxymethyl-pyridin-3-carbonsäure (Imazamox),
2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin),
2-(4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure
(Imazethapyr),
N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 4-
Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-
harnstoff (Isoproturon),
N-(3-(1-Ethyl-1-methyl-propyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben),
(4-Chlor-2-methylsulfonyl-phenyl)-(5-cyclopropylisoxazol-4-yl)-methanon (Isoxachlortole),
(5-Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethyl-phenyl)-methanon (Isoxaflutole),
(4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop),
2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet),
2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-
amino]methyl]-benzoesäure-methylester (Mesosulfuron), 4-Amino-3-methyl-6-
phenyl-1,2,4-triazin-5(4H)-on (Metamitron), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-
dimethoxy-1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam), 4-Amino-6-
tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6-
methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff
(Metsulfuron-methyl), 1-Amino-N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol
(Pendimethalin), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2-carboxamid
(Picolinafen), N-(3,4-Dichlor-phenyl)-propanamid (Propanil), Ethyl-(2-Chlor-5-(4-
chlor-5-difluormethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat
(Pyraflufen-ethyl), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione),
N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate),
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo[1,2-a]pyridin-3-sulfonamid (Sulfosuliron),
N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-
sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-
(2,4,6-trimethyl-phenyl)-2-cyclohexen-1-on (Tralkoxydim), S-(2,3,3-Trichlor-2-
propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl-1,3,5-
triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-
Methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl),
1-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-
yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),
Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H-1,2,4-triazol-1-yl]-2-
[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991) und (2-
Chloro-N-[1-[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-1H-pyrazol-5-yl]-
propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599).
Preferred mixture components from the active ingredients in group 3 are one or more compounds from a group of herbicides which contain the active ingredients mentioned below:
4-amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro-3- (1-methyl-ethyl) -5-oxo-1H-1,2,4-triazole-1-carboxamide ( Amicarbazones), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N-benzyl-2- (4-fluoro- 3-trifluoromethyl-phenoxy) butanamide (beflubutamide), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) ) -2-nitrobenzoate (bifenox), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl ) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (carfentrazone-ethyl), N- (4-methoxy-6-methyl-1,3, 5- triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlorotoluron) , 2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (clodinafop propargyl), 3,6-dichloro-py ridin-2-carboxylic acid (clopyralide), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4- Dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), 1,2-dimethyl-3,5-diphenyl -1H-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), N- (4,6-dimethoxypyrimidine) 2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (ethoxysuliron), (R) - ethyl 2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (Fenoxaprop- (P) - ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl -N-benzoyl-N- (3-chloro-4-fluro-phenyl) -DL- alaninate (Flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L- alaninate (flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) - DL-alaninate (flamprop-methyl), N- (2,6-difluorophenyl) - 8-fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyr imidin-2-sulfonamide (florasulam), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1- H-1,2,4-triazole-1-carboxamide sodium salt ( Flucarbazone-sodium), N- (4-fluorophenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (Flufenacet), 5- (2-chlorine -4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridine -2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy- 1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (flurtamone) , 2-Amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopro pylammmonium salt), (glyphosate, isopropylammonium), methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz- methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4th , 5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4- methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo -1H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N'- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4- isopropyl-phenyl) -urea (isoproturon), N- (3- (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro- 2-methylsulfonylphenyl) - (5-cyclopropylisoxazol-4-yl) methanone (isoxachlorotole ), (5-Cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole), (4-chloro-2-methyl-phenoxy) -acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mefenacet), 2 - [[[[(4,6-dimethoxy -2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), 4-amino-3-methyl-6-phenyl- 1,2,4-triazin-5 (4H) -one (metamitron), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1, 5-a] pyrimidine-2-sulfonamide (metosulam), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), N- (4th -Methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), 1-amino-N- (1-ethyl-propyl ) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), N- (4-fluoro-phenyl) -6- (3-trifluoromethyl-phenoxy) -pyridine-2-carboxamide (picolinafen), N- (3,4-dichlorophenyl) propanamide (propanil), ethyl (2-chloro-5- (4-chloro 5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), 2- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3 -dione (Sulcotrione), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine -3-sulfonamide (sulfosulirone), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl sulfonyl) urea (Thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2,3, 3-trichloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloro-ethoxy ) -phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Tribenuron-methyl), 1-amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazine 2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea ff (tritosulfuron), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2- [( ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and (2-chloro-N- [1- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro -1H-pyrazol-5-yl] - propanecarboxamide (CAS number 121750-17-2; SLA5599).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 3 werden in besonderem
Maße Herbizide der Klasse der Sulfonylharnstoffe, Triazolopyrimidine Imidazolinone,
Harnstoffe, Triazindione, Triketone, Triazolinone, Benzonitrile,
Phenoxypropionsäurederivate, Dichlorphenoxysäurederivate, Carboxamide, Oxyacetamide sowie
weitere herbizide Wirkstoffe hervorgehoben, die nach stehend im einzelnen aufgeführt
werden:
- a) Sulfonylharnstoffe:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)- N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N-(4,6-Dimethoxypyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), N-(4- Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(2-ethylsulfonyl-imidazo[1,2-a]pyridin-3-sulfonamid (Sulfosulfuron), N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-ylsulfonyl)-harnstoff (Thifensulfuron-methyl), N-(4-Methoxy-6-methyl-1,3,5- triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxy- carbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), - b) Triazolopyrimidine:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidin- 2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- 1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam), - c) Imidazolinone:
Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-4- methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5- Dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridin-3- carbonsäure (Imazethapyr), - d) Harnstoffe:
N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), N,N- Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), - e) Triazindione:
4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), - f) Triketone:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione), - g) Triazolinone:
2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H- 1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluoro-(CAS-Nummer 173980-17-1, HWH4991), - h) Benzonitrile:
3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 4-Hydroxy-3,5-diiodbenzonitril (Ioxynil), - i) Phenoxypropionsäurederivate:
(R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), - j) Dichlorphenoxysäurederivate:
2,4-Dichlor-phenoxyessigsäure (2,4-D), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2- (4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), - k) Carboxamide:
N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen), - l) Oxyacetamide:
N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-1,3,4-thiadiazol-2-yl- oxy)-acetamid (Flufenacet),
(2-Chloro-N-[1-[2,6-dichl oro-4-(difluoromethyl)phenyl]-4-nitro-1H-pyrazol-5-yl]- propancarbonsäureamid (CAS-Nummer 121750-12-2; SLA5599),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox),
2-Chlor-3-[2-chlor-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2- propansäure-ethylester (Cinidon-ethyl),
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1-methylethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),
2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)),
N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium),
N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate).
- a) Sulfonylureas:
N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3 , 5-triazin-2-yl) - N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N- (4,6-dimethoxypyrimidin-2-yl) -N' - (3-methoxycarbonyl-6- trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- ( 5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl ] -4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- ( 2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N- (4,6-dimethoxypyrimidin-2-yl) - N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3- sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-ylsulfonyl) urea (thifensulfuron-methyl) , N- (4-methoxy-6-methyl-1,3,5- t riazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3,5- triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), - b) Triazolopyrimidines:
N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyrimidine- 2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), - c) Imidazolinones:
Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1 H -imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4.5 Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl- 4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo -1H-imidazol-2-yl) -quinolin-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), - d) ureas:
N '- (3-chloro-4-methyl-phenyl) -N, N-dimethyl-urea (chlorotoluron), N, N-dimethyl-N' - (4-isopropyl-phenyl) -urea (isoproturon), - e) Triazinediones:
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), - f) Triketones:
2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), - g) triazolinones:
2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4- triazol-3-one (carfentrazone-ethyl), phenylcarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl ] -2 - [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991), - h) Benzonitrile:
3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), - i) Phenoxypropionic acid derivatives:
(R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxypropanoate (clodinafop-propargyl), methyl 2- [4- ( 2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop - (P) -ethyl), - j) dichlorophenoxyacid derivatives:
2,4-dichlorophenoxyacetic acid (2,4-D), (R) -2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), (4-chloro-2-methylphenoxy) - acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), - k) carboxamides:
N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) -pyridine-2-carboxamide (picolinafen), - l) oxyacetamides:
N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet),
(2-Chloro-N- [1- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propane carboxamide (CAS number 121750-12-2; SLA5599),
Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox),
2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid - ethyl ester (cinidon-ethyl),
(4-Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-1-methylethyl ester, -1-methyl-heptyl ester) (fluroxypyr, butoxypropyl, meptyl )
2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)),
N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium),
N-phosphonomethyl-glycine trimethyl sulfonium (sulfosate).
Als Mischungskomponenten aus den Wirkstoffen der Gruppe 4 werden besonders
hervorgehoben:
5-Chlor-chinoxalin-8-oxy-essigsäure-(1-methylhexylester) (Cloquintocet),
1-(2,4-Dichlor-phenyl)-5-trichlormethyl-1H-1,2,4-triazol-3-carbonsäure-ethylester
(Fenchlorazol-ethyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl),
(4-Chlor-2-methylphenoxy)-essigsäure (MCPA),
2-(4-Chlor-2-methylphenoxy)-propionsäure (Mecoprop), Diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-
pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlorophenoxyessigsäure
(2,4-D) und dessen Derivate.
The following are particularly emphasized as components of the group 4 active ingredients:
5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (cloquintocet), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4th - Chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
Erfindungsgemäß ganz besonders bevorzugt sind die oben genannten
selektivherbiziden Mittel, die gekennzeichnet sind durch einen Gehalt an einer
Wirkstoffkombination umfassend
- a) mindestens ein Phenoxypyrimidin-Derivat aus der folgenden Gruppe von
Verbindungen:
2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribacsodium, KIH 2023) der Formel
oder
Diphenyl-methanon-O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]- oxim (Pyribenzoxim) der Formel
- b) der Verbindung Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-
1,2,4-triazol-1-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz
(Propoxycarbazone-sodium) der Formel
sowie - c) zumindest einen der vorstehend genannten Wirkstoffe der Gruppe 3,
sowie gegebenenfalls - d) zumindest eine der vorstehend genannten, die Kulturpflanzen-Verträglichkeit verbessernden Verbindung der Gruppe 4, wobei solche Verbindungen bevorzugt sind, die vorstehend in bevorzugten Bereichen genannt wurden.
- a) at least one phenoxypyrimidine derivative from the following group of compounds:
2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribacsodium, KIH 2023) of the formula
or
Diphenylmethanone-O- [2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoyl] oxime (pyribenzoxime) of the formula
- b) the compound methyl-2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino] sulfonyl] -benzoic acid, sodium salt (Propoxycarbazone-sodium) of the formula
such as - c) at least one of the above-mentioned active ingredients of group 3,
and if necessary - d) at least one of the above-mentioned compounds of group 4 which improve crop plant tolerance, preference being given to those compounds which have been mentioned above in preferred ranges.
Erfindungsgemäß am meisten bevorzugt sind selektiv-herbizide Mittel, die
gekennzeichnet sind durch einen Gehalt an einer Wirkstoftkombination umfassend
- a) 2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy)-benzoat (Natrium),
(Bispyribacsodium) der Formel
und - b) Methyl-2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)
carbonyl]amino)sulfonyl]-benzoesäure, Natrium-Salz
(Propoxycarbazonesodium) der Formel
sowie - c) zumindest eine weitere Verbindung ausgewählt aus den folgenden
Wirkstoffen der Gruppe 3:
- a) Sulfonylharnstoffe:
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)- N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N- Methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylphenylsulfonyl)-harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), - b) Triazolopyrimidine:
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidin- 2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy- 1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam), - c) Imidazolinone:
2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), - d) Harnstoffe:
N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), - e) Triazindione:
4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), - f) Triketone:
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione), - g) Triazolinone:
Benzenecarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H- 1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS 173980-17-1, HWH4991),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), und
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1-methylethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),
sowie gegebenenfalls - a) Sulfonylharnstoffe:
- d) zumindest eine der vorstehend genannten, die Kulturpflanzen-Verträglichkeit verbessernden Verbindung der Gruppe 4, wobei solche Verbindungen bevorzugt sind, die vorstehend in bevorzugten Bereichen genannt wurden.
- a) 2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy) benzoate (sodium), (bispyribacsodium) of the formula
and - b) Methyl-2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino) sulfonyl] benzoic acid , Sodium salt (propoxycarbazone sodium) of the formula
such as - c) at least one further compound selected from the following active ingredients of group 3:
- a) Sulfonylureas:
N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3 , 5-triazin-2-yl) - N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazine -2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N' - ( 2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), - b) Triazolopyrimidines:
N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyrimidine- 2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), - c) Imidazolinones:
2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1 H -imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), - d) ureas:
N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), - e) Triazinediones:
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), - f) Triketones:
2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), - g) triazolinones:
Benzenecarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H- 1,2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] - 5-fluoro- (CAS 173980-17-1, HWH4991),
Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), and
(4-Amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-1-methylethyl ester, -1-methyl-heptyl ester) (fluroxypyr, butoxypropyl, meptyl )
and if necessary - a) Sulfonylureas:
- d) at least one of the above-mentioned compounds of group 4 which improve crop plant tolerance, preference being given to those compounds which have been mentioned above in preferred ranges.
Es wurde nun überraschend gefunden, dass die oben definierten Wirkstoffkombinationen aus den Phenoxypyrimidin-Derivaten der Formel (I) und dem Wirkstoff der Gruppe 2 in Kombination mit Wirkstoffen der Gruppe 3, gegebenenfalls in Kombinationen mit Wirkstoffen der Gruppe 4 bei sehr guter Nutzpflanzen-Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Nutzpflanzenkulturen wie z. B. in Soja, Kartoffeln, Mais oder Reis und insbesondere in Getreide, wie z. B. Gerste, Roggen, Triticale und besonders Weizen zur selektiven Unkrautbekämpfling verwendet werden können. It has now surprisingly been found that those defined above Active ingredient combinations of the phenoxypyrimidine derivatives of the formula (I) and the active ingredient of Group 2 in combination with active ingredients of group 3, optionally in Combinations with active ingredients of group 4 with very good crop tolerance have a particularly high herbicidal activity and in different Crop crops such as B. in soy, potatoes, corn or rice and especially in Cereals such as B. barley, rye, triticale and especially wheat for selective Weed control can be used.
Überraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirkstoffkombinationen aus Verbindungen der oben aufgeführten Gruppen 1, 2 und 3 erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe. Surprisingly, the herbicidal activity of the invention Active ingredient combinations of compounds from groups 1, 2 and 3 listed above considerably higher than the sum of the effects of the individual active ingredients.
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungsergänzung. Die neuen Wirkstoftkombinationen sind in vielen Kulturen gut verträglich, wobei die neuen Wirkstoftkombinationen auch sonst schwer bekämpftbare Unkräuter gut bekämpfen. Die neuen Wirkstoftkombinationen stellen somit eine wertvolle Bereicherung der Selektivherbizide dar. There is therefore an unforeseeable synergistic effect and not just one Addition of activities. The new combinations of active ingredients are good in many cultures tolerated, whereby the new active substance combinations are otherwise difficult to fight Control weeds well. The new combinations of active ingredients therefore represent one valuable enrichment of selective herbicides.
Es wurde außerdem überraschend gefunden, dass die oben definierten Wirkstoffkombinationen aus Phenoxypyrimidin-Derivaten der Formel (I) bzw. deren Salze und einem Safener/Antidot ("Wirkstoffe der Gruppe 4") in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und Gruppe 3 bei sehr guter Nutzpflanzen-Verträglichkeit eine besonders hohe herbizide Wirksamkeit aufweisen und in verschiedenen Kulturen, insbesondere in Getreide, vor allem Weizen, aber auch in Soja, Kartoffeln, Mais und Reis zur selektiven Unkrautbekämpfung verwendet werden können. It was also surprisingly found that those defined above Active ingredient combinations of phenoxypyrimidine derivatives of the formula (I) or their salts and one Safener / antidote ("active substances of group 4") in combination with one or more the group 2 and group 3 active ingredients listed above with very good Crop crop tolerance has a particularly high herbicidal activity and in different cultures, especially in cereals, especially wheat, but also used in soy, potatoes, corn and rice for selective weed control can be.
Überraschenderweise wurde zudem gefunden, dass auch die herbizidwirksame Substanz MCPA sowie die Substanz 2,4-Dichlorophenoxyessigsäure (2,4-D) und ihre Derivate die oben beschriebene Safeneraufgabe übernehmen können. Surprisingly, it was also found that the herbicidal Substance MCPA and the substance 2,4-dichlorophenoxyacetic acid (2,4-D) and their Derivatives can take over the safener task described above.
Eine bevorzugte Ausführungsform ist daher auch eine Mischung enthaltend eine Verbindung der Formel (I) und/oder deren Salze einerseits und 2,4-D und/oder dessen Derivate andererseits, in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und 3. Typische Derivate von 2,4-D sind z. B. deren Ester. A preferred embodiment is therefore also a mixture containing one Compound of formula (I) and / or its salts on the one hand and 2,4-D and / or its Derivatives, on the other hand, in combination with one or more of the above Active ingredients listed in groups 2 and 3. Typical derivatives of 2,4-D are e.g. B. their esters.
Eine bevorzugte Ausführungsform ist weiterhin eine Mischung enthaltend eine Verbindung der Formel (I) und/oder deren Salze einerseits und MCPA andererseits in Kombination mit dem oben angeführten Wirkstoff der Gruppe 2 und einem oder mehreren Verbindungen der Gruppe 3. A preferred embodiment is also a mixture containing one Compound of formula (I) and / or their salts on the one hand and MCPA on the other hand in Combination with the above-mentioned active ingredient of group 2 and one or several Group 3 compounds.
Die Verbindungen Diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole- 3,5-dicarboxylate (Mefenpyr-diethyl), (1-methylhexyl)-[(5-chloro-8-quinolinyl)oxy]- acetate (Cloquintocet-mexyl) und Ethyl-1-(2,4-dichlorophenyl)-5-(trichloromethyl)- 1H-1,2,4-triazole-3-carboxylate (Fenchlorazole-ethyl) sind in den folgenden Patentanmeldungen beschrieben: DE-A-39 39 503, EP- A-191 736 bzw. DE-A-35 25 205. 2,4-D ist ein bekanntes Herbizid. (4-Chloro-2-methylphenoxy)-essigsäure (MCPA) ist ebenfalls ein bekanntes Herbizid. The compounds diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole- 3,5-dicarboxylates (mefenpyr-diethyl), (1-methylhexyl) - [(5-chloro-8-quinolinyl) oxy] - acetate (Cloquintocet-mexyl) and ethyl 1- (2,4-dichlorophenyl) -5- (trichloromethyl) - 1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl) are in the following Patent applications described: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a well-known herbicide. (4-Chloro-2-methylphenoxy) acetic acid (MCPA) also a well known herbicide.
Als überraschend ist weiterhin anzusehen, dass aus einer Vielzahl von bekannten Safenern oder Antidots, die befähigt sind, die schädigende Wirkung eines Herbizids auf die Kulturpflanzen zu antagonisieren, gerade die oben aufgeführten Verbindungen der Gruppe 4 geeignet sind, die schädigende Wirkung von Verbindungen der Formel (I) und deren Salzen in Kombination mit einem oder mehreren des bzw. der oben angeführten Wirkstoffe der Gruppe 2 und 3, auf die Kulturpflanzen armähernd vollständig aufzuheben, ohne dabei die herbizide Wirksamkeit gegenüber den Unkräutern zu beeinträchtigen. It is also to be regarded as surprising that from a large number of known Safeners or antidotes that are capable of the harmful effects of a herbicide to antagonize the crops, just the compounds of the above Group 4 are suitable, the damaging effect of compounds of formula (I) and their salts in combination with one or more of the above Active ingredients listed in groups 2 and 3, approximate to the crop plants completely repeal without the herbicidal activity against the To affect weeds.
Die erfindungsgemäßen Wirkstoffkombinationen können z. B. bei den folgenden
Pflanzen verwendet werden:
Dikotyle Unkräuter der Gattungen: Sinapis, Lepidium, Galium, Stellaria, Matricaria,
Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,
Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus,
Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex,
Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dikotyle Kulturen der Gattungen: Gossypium, Glycine, Beta, Daucus, Phaseolus,
Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica,
Lactuca, Cucumis, Cuburbita.
Monokotyle Unkräuter der Gattungen: Echinochloa, Setaria, Panicum, Digitaria,
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,
Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,
Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus,
Apera, Phalaris.
Monokotyle Kulturen der Gattungen: Oryza, Zea, Triticum, Hordeum, Avena, Secale,
Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
The active substance combinations according to the invention can, for. B. can be used in the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.
Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
Die Verwendung der erfindungsgemäßen Wirkstoffkombinationen ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen. However, the use of the active compound combinations according to the invention is by no means limited to these genres, but extends in the same way other plants.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods can be obtained, including and including the transgenic plants plant varieties that can or cannot be protected by plant breeders' rights. Plant parts should include all above-ground and underground parts and organs of plants, such as sprout, leaf, flower and root are understood, whereby for example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. To the plant parts also includes crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, habitat or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and in the case of propagation material, especially in the case of seeds, further by single or multi-layer coating.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert. As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild existing or by conventional organic breeding methods, such as crossing or protoplast fusion obtained plant species and plant varieties and their Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties, if necessary by genetic engineering methods in combination with conventional methods (Genetically Modified Organisms) and their parts. The term "parts" or "parts of." Plants "or" parts of plants "was explained above.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit bestimmten Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Bio- und Genotypen sein. Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with certain properties ("traits") that are characterized by both conventional breeding, by mutagenesis or by recombinant DNA techniques have been obtained. These can be varieties, bio and genotypes.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Eniteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus thuringiensis (z. B. durch die Gene CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb und CryIF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinothricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z. B. Mais, Baumwolle, Soja), KnockOut® (z. B. Mais), StarLink® (z. B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z. B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z. B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z. B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z. B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften ("Traits"). Among the preferred transgenes to be treated according to the invention (Genetically preserved) plants or plant varieties include all plants that received genetic material through the genetic modification, which gives these plants particular beneficial properties ("traits"). Examples of such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the enite products, higher shelf life and / or Machinability of crop products. Further and particularly highlighted examples for such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. The important ones are examples of transgenic plants Crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and Grapes) mentioned, especially corn, soybeans, potatoes, cotton and rapeseed be highlighted. As properties ("traits") become special highlighted the increased defense of plants against insects by in the Plant-derived toxins, especially those caused by the genetic material from Bacillus thuringiensis (e.g. through the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF as well as their Combinations) are generated in the plants (hereinafter "Bt plants"). As Properties ("traits") are also particularly emphasized the increased defense of plants against fungi, bacteria and viruses by systemic acquirers Resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and appropriately expressed proteins and toxins. As traits further emphasized the increased tolerance of plants certain herbicidal active ingredients, for example imidazolinones, Sulfonylureas, glyphosate or phosphinothricin (e.g. "PAT" gene). The each the desired properties ("traits") conferring genes can also in Combinations with each other occur in the transgenic plants. As examples for "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties under the trade names YIELD GARD® (e.g. maize, Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and Soybeans known as Roundup Ready® (Tolerance to glyphosates e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. Rape), IMI® (tolerance to imidazolinones) and STS® (Tolerance to sulfonylureas e.g. maize). As a herbicide resistant (conventionally grown to herbicide tolerance) plants are also the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to future developed or future plant varieties with these or in the future developed genetic traits.
Der synergistische Effekt der erfindungsgemäßen Wirkstoftkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I) jeweils 0,001 bis 1000 Gewichtsteile, vorzugsweise jeweils 0,005 bis 200 Gewichtsteile und besonders bevorzugt jeweils 0,01 bis 100 Gewichtsteile Wirkstoff der Gruppe 2 und 3. Insbesondere entfallen auf 1 Gewichtsteil der Gruppe 1 jeweils 0,1 bis 1 Gewichtsteile der Wirkstoffe der Gruppe 2 und 3. The synergistic effect of the active substance combinations according to the invention is at certain concentration ratios particularly pronounced. However, they can Weight ratios of the active ingredients in the active ingredient combinations in relatively large Ranges can be varied. In general, 1 part by weight of the active ingredient Formula (I) 0.001 to 1000 parts by weight each, preferably 0.005 to 200 parts by weight Parts by weight and particularly preferably 0.01 to 100 parts by weight of active ingredient of groups 2 and 3. In particular, 1 part by weight of group 1 accounts for 0.1 each up to 1 part by weight of the active ingredients in groups 2 and 3.
Der vorteilhafte Effekt der Kulturpflanzenverträglichkeit der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen ebenfalls besonders stark ausgeprägt. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil Wirkstoff der Formel (I), seinen Salzen oder dessen Mischungen mit Wirkstoffen der Gruppe 2 und 3 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis 100 Gewichtsteile und besonders bevorzugt 0,1 bis 10 Gewichtsteile einer der oben unter (d) genannten, die Kulturpflanzen Verträglichkeit verbessernden Verbindungen (Antidots/Safener). The advantageous effect of the crop plant tolerance of the invention Active ingredient combinations is also available at certain concentration ratios particularly pronounced. However, the weight ratios of the active ingredients in the Drug combinations can be varied in relatively large areas. In general account for 1 part by weight of active ingredient of the formula (I), its salts or its Mixtures with active ingredients of groups 2 and 3 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 Parts by weight of one of the crops tolerated above under (d) improving compounds (antidots / safeners).
Die Wirkstoffkombinationen können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoffimprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen. The active substance combinations can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, Pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymers Substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, if appropriate using surface-active agents, that is Emulsifiers and / or dispersants and / or foaming agents.
Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols, such as Butanol or glycol and their ethers and esters, ketones such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as Dimethylformamide and dimethyl sulfoxide, as well as water.
Als feste Trägerstoffe kommen in Frage:
z. B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum,
Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische
Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste
Trägerstoffe für Granulate kommen in Frage: z. B. gebrochene und fraktionierte natürliche
Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate
aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material
wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstengeln; als Emulgier-
und/oder schaumerzeugende Mittel kommen in Frage: z. B. nichtionogene und
anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-
Ether, z. B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate
sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z. B.
Lignin-Sulfitablaugen und Methylcellulose.
The following are suitable as solid carriers:
z. B. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other additives can mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent an Wirkstoffen einschließlich der safenden Wirkstoffe, vorzugsweise zwischen 0,5 und 90%. The formulations generally contain between 0.1 and 95 percent by weight of active substances, including the safe active substances, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffkombinationen werden im allgemeinen in Form von Fertigformulierungen zur Anwendung gebracht. Die in den Wirkstoffkombinationen enthaltenen Wirkstoffe können aber auch in Einzelformulierungen bei der Anwendung gemischt, d. h. in Form von Tankmischungen zur Anwendung gebracht werden. The active compound combinations according to the invention are generally in the form of Ready formulations applied. The one in the drug combinations Active ingredients contained can also be used in individual formulations mixed, d. H. be used in the form of tank mixes.
Die neuen Wirkstoffkombinationen können als solche oder in ihren Formulierungen weiterhin auch in Mischung mit anderen bekannten Herbiziden Verwendung finden, wobei wiederum Fertigformulierungen oder Tankmischungen möglich sind. Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Wuchsstoffen, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich. Für bestimmte Anwendungszwecke, insbesondere im Nachauflauf-Verfahren, kann es ferner vorteilhaft sein, in die Formulierungen als weitere Zusatzstoffe pflanzenverträgliche mineralische oder vegetabilische Öle oder Ammoniumsalze wie z. B. Ammoniumsulfat oder Ammoniumrhodanid aufzunehmen. The new drug combinations can be used as such or in their formulations continue to be used in a mixture with other known herbicides, ready formulations or tank mixes are possible. Also one Mixture with other known active ingredients, such as fungicides, insecticides, Acaricides, nematicides, bird repellants, growth substances, Plant nutrients and soil structure improvers are possible. For certain Applications, especially in the post-emergence process, it can also be advantageous in the Formulations as additional additives plant-compatible mineral or vegetable oils or ammonium salts such as B. ammonium sulfate or Absorb ammonium rhodanide.
Die neuen Wirkstoftkombinationen können als solche, in Form ihrer Formulierungen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z. B. durch Gießen, Spritzen, Sprühen, Stäuben oder Streuen. The new active substance combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules be applied. The application happens in the usual way, e.g. B. by casting, Spraying, spraying, dusting or sprinkling.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auflaufen der Pflanzen appliziert werden, also im Vorauflauf und Nachauflauf-Verfahren. Sie können auch vor der Saat in den Boden eingearbeitet werden. The active substance combinations according to the invention can be used before and after emergence of the plants are applied, i.e. pre-emergence and post-emergence. she can also be worked into the soil before sowing.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbizide Wirkung der Wirkstoftkombination größer ist als die der einzelnen applizierten Wirkstoffe. A herbicide always has a synergistic effect if the herbicide Effect of the combination of active ingredients is greater than that of the individual applied Agents.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie
folgt berechnet werden (vgl. COLBY, S. R.: "Calculating synergistic and antagonistic
responses of herbicide combinations", Weeds 15, Seiten 20-22, 1967):
Wenn X = % Schädigung durch Herbizid A (Wirkstoff der Gruppe
1) bei p kg/ha Aufwandmenge
und Y = % Schädigung durch Herbizid B (Wirkstoff der Gruppe
2) bei q kg/ha Aufwandmenge
und Z = % Schädigung durch Herbizid C (Wirkstoff der Gruppe
3) bei r kg/ha Aufwandmenge
und E = die erwartete Schädigung der Herbizide A B und C bei
p, q und r kg/ha Aufwandmenge,
dann ist
The expected effect for a given combination of two herbicides can be calculated as follows (cf. COLBY, SR: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
If X =% damage from herbicide A (active ingredient of group 1) at p kg / ha application rate
and Y =% damage by herbicide B (active ingredient of group 2) at q kg / ha application rate
and Z =% damage by herbicide C (active ingredient of group 3) at an application rate of r kg / ha
and E = the expected damage to the herbicides AB and C at p, q and r kg / ha,
then
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt. If the actual damage is greater than calculated, the combination is in its Effect over additive, that is, it shows a synergistic effect.
Claims (14)
in welcher
R für Wasserstoff, -CH2CH2S(O)nR1 (wobei R1 für C1-C4-Alkyl und n für 0, 1 oder 2 steht) oder
steht,
wobei
R2 für Wasserstoff, Halogen, Cyano, Phenyl, C1-C8-Alkyl, C1-C4- Alkoxy, C1-C4-Alkylthio, C1-C4-Alkoxycarbonyl, Mono- oder Di-C1-C4-Alkylaminocarbonyl, Phenyl-C1-C4 -Alkylaminocarbonyl steht, wobei die Phenylgruppe gegebenenfalls durch Halogen, C1-C2-Alkyl oder C1-C2-Alkoxy, Furylmethylaminocarbonyl oder Phenyl substituiert sein kann, und
R3 für jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1- C4-Alkyl, C1-C4-Alkoxy oder Allyloxy substituiertes Phenyl, für gegebenenfalls durch C1-C4-Alkyl, Phenoxy, Benzyloxy oder Acetoxy substituiertes Amino, für C1-C4-Alkylthio oder für die Gruppierung -COR4 steht, wobei R4 für C1-C4-Alkoxy, C1- C4-Alkyl, Benzyloxy oder Benzylamino steht,
A für Chlor oder Methoxy steht und
D und E, die gleich oder unterschiedlich sein können, für Wasserstoff, Halogen, C1-C8-Alkyl, C1-C8-Alkoxy oder durch Halogen substituiertes C1-C8-Alkoxy stehen,
und/oder einem Salz einer Verbindung der Formel (I)
("Wirkstoffe der Gruppe 1"),
und
Methyl-2-[[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol- 1-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazone-sodium) der Formel
und
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)- phenyl]sulfonyl]-1H-1,2,4-triazol-1-carboxamid, Natrium-Salz (Flucarbazone-sodium) der Formel
("Wirkstoffe der Gruppe 2"),
sowie
2-Chlor-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamid (Acetochlor), 5-(2-Chlor-4-trifluormethyl-phenoxy)-2-nitro-benzoesäure-Natriumsalz (Acifluorfen-sodium), 2-Chlor-6-nitro-3-phenoxybenzenamin (Aclonifen), 2-Chlor-N-(methoxymethyl)-N-(2,6-diethylphenyl)-acetamid (Alachlor), N-Ethyl-N'-i-propyl-6-methylthio-1,3,5- triazin-2,4-diamin (Ametryn), 4-Amino-N-(1,1-Dimethyl-ethyl)-4,5- dihydro-3-(1-methyl-ethyl)-5-oxo-1H-1,2,4-triazol-1-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N- methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), 1H-1,2,4-Triazol-3-amin (Amitrole), S-[2-[(4-Chlor-phenyl)-(1-isopropyl)-amino]- 2-oxo-ethyl]-O,O-dimethyl-phosphorodithioate (Anilofos), 6-Chlor-4- ethylamino-2-isopropylamino-1,3,5-triazin (Atrazin), 2-[2,4-Dichlor- 5-(2-propinyloxy)-phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]- pyridin-3(2H)-on (Azafenidin), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-ylsulfonyl]harnstoff (Azimsulfuron), N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 4-Chlor-2-oxo-3(2H)-benzthiazolessigsäure (Benazolin), N-Butyl-N-ethyl-2,6-dinitro-4-trifluormethylbenzenamin (Benfluralin), 2,3-Dihydro-3,3-dimethyl-5-benzofuranylethansulfonat (Benfuresate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'- (2-methoxycarbonyl-phenylmethylsulfonyl)-harnstoff (Bensulfuronmethyl), S-[(4-Chlor-phenyl)-methyl]-diethylthiocarbamat (Benthiocarb, Thiobencarb), 2-[2-[4-(3,6-Dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-1(2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propansäure-methylester (Benzfendizone), 3-(2-Chlor-4-methylsulfonylbenzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-on (Benzobicyclon), 2-[[4-(2,4-Dichlor-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]- oxy]-1-(4-methyl-phenyl)-ethanon (Benzofenap), Ethyl N-benzoyl-N- (3,4-dichlor-phenyl)-DL-alaninat (Benzoylprop-ethyl), 3-i-Propyl-1H- 2,1,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlorphenoxy)-2-nitro-benzoat (Bifenox), 5-Brom-6-methyl-3-(1-methylpropyl)-2,4(1H,3H)pyrimidindion (Bromacil), 2-Brom-3,3-dimethyl- N-(1-methyl-1-phenyl-ethyl)-butanamid (Bromobutide), 3,5-Dibrom- 4-hydroxy-benzaldehyd-O-(2,4-dinitro-phenyl)-oxim (Bromofenoxim), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), N-Butoxymethyl-2-chlor-N-(2,6-diethyl-phenyl)-acetamid (Butachlor), 2-Chlor- 5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl-1(2H)-pyrimidinyl)-benzoesäure-[1,1-dimethyl-2-oxo-2-(2-propenyloxy)]-ethylester (Butafenacil-allyl), 2-(1-Ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxo-butyl)-phenyl]-2-cyclohexen-1-on (Butroxydim), S- Ethyl-bis-(2-methyl-propyl)-thiocarbamat (Butylate), N,N-Diethyl-3- (2,4,6-trimethyl-phenylsulfonyl)-1H-1,2,4-triazol-1-carboxamid (Cafenstrole), 2-[1-[(3-Chlor-2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-on (Caloxydim, Tepraloxydim), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonylethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), 2,4-Dichlor-1-(3-methoxy-4-nitrophenoxy)-benzol (Chlomethoxyfen), 3-Amino-2,5-dichlor-benzoesäure (Chloramben), N-(4-Chlor-6-methoxy-pyrimidin-2-yl)-N'-(2- ethoxycarbonyl-phenylsulfonyl)-harnstoff (Chlorimuron-ethyl), 1,3,5- Trichlor-2-(4-nitro-phenoxy)-benzol (Chlornitrofen), N-(4-Methoxy- 6-methyl-1,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(1,3,4,5,6,7-hexahydro-1,3- dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidonethyl), Exo-1-methyl-4-isopropyl-2-(2-methyl-phenyl-methoxy)-7- oxabicyclo-[2.2.1]-heptan (Cinmethylin), N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy-ethoxy)-phenylsulfonyl)-harnstoff (Cinosuliron), 2-[1-[2-(4-Chlorphenoxy)-propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexandion (Clefoxydim), (E,E)- (+)-2-[1-[[(3-Chlor-2-propenyl)-oxy]-imino]-propyl]-3-hydroxy-2- cyclohexen-1-on (Clethodim), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluorpyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 2-(2,4- Dichlor-3-methyl-phenoxy)-N-phenyl-propanamid (Clomeprop), 3,6- Dichlor-pyridin-2-carbonsäure (Clopyralid), Methyl-3-chloro-2-[(5- ethoxy-7-fluor[1,2,4]triazolo[1,5-c]pyrimidin-2-yl-sulfonyl)-amino]- benzoat (Cloransulam-methyl), N-[(2-Chlor-phenyl)-methyl]-N'-(1- methyl-1-phenyl-ethyl)-harnstoff (Cumyluron), 2-Chlor-4-ethylamino- 6-(1-cyano-1-methyl-ethylamino)-1,3,5-triazin (Cyanazine), N-(4,6- Dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenylsulfonyl)-harnstoff (Cyclosulfamuron), 2-(1-Ethoximinobutyl)-3- hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-on (Cycloxydim), (R)-2-[4-(4-Cyano-2-fluor-phenoxy)-phenoxy]-propansäure-butylester (Cyhalofop-butyl), 2,4-Dichlor-phenoxyessigsäure (2,4-D), 3,6-Dichlor-2-methoxy-benzoesäure (Dicamba), (R)-2-(2,4- Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofop-methyl), N-(2,6-Dichlor-phenyl)-5-ethoxy-7-fluor-[1,2,4]-triazolo-[1,5-c]-pyrimidin-2- sulfonamid (Diclosulam), 1,2-Dimethyl-3,5-diphenyl-1H-pyrazoliummethylsulfat (Difenzoquat), N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), 2-[1-[(3,5-Difluor-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridin-3-carbonsäure (Diflufenzopyr), S-(1-Methyl-1-phenyl-ethyl)-1-piperidin-carbothioat (Dimepiperate), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(2-methoxy-ethyl)-acetamid (Dimethachlor), N-(1,2-Dimethyl-propyl)-N'- ethyl-6-methylthio-1,3,5-triazin-2,4-diamin (Dimethametryn), (S-) 2- Chlor-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamid (S-) (Dimethenamid), 2-Amino-4-(1-fluor-1-methyl-ethyl)-6-(1- methyl-2-(3,5-dimethyl-phenoxy)-ethylamino)-1,3,5-triazin (Dimexyflam), N3,N3-Diethyl-2,4-dinitro-6-trifluormethyl-1,3-diamino-benzol (Dinitramine), 6,7-Dihydro-dipyrido[1,2-a:2',1'-c]pyrazindiium (Diquat), S,S-Dimethyl-2-difluormethyl-4-i-butyl-6-trifluormethylpyridin-3,5-dicarbothioat (Dithiopyr), N'-(3,4-Dichlor-phenyl)-N,N- dimethyl-harnstoff (Diuron), N-(4-Methyl-phenyl)-N'-(1-methyl-1- phenyl-ethyl)-harnstoff (Dymron, Daimuron), 2-[2-(3-Chlor-phenyl)- oxiranylmethyl]-2-ethyl-1H-inden-1,3(2H)-dion (Epropodan), S- Ethyl-dipropylthiocarbamat (EPTC), S-(Phenylmethyl)-N-ethyl-N- (1,2-dimethyl-propyl)-thiocarbamat (Esprocarb), N-Ethyl-N-(2- methyl-2-propenyl)-2,6-dinitro-4-trifluormethyl-benzenamin (Ethalfluralin), (S)-(2-Ethoxy-1-methyl-2-oxoethyl)-2-chlor-5-(2-chlor-4-trifluormethyl-phenoxy)-benzoat (Ethoxyfen), N-(4,6-Dimethoxypyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), N-(2,3-Dichlor-phenyl)-4-ethoxymethoxybenzamid (Etobenzanid), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]- propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N-cyclohexyl- N-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L- alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4- fluor-phenoxy)-DL-alaninat (Flamprop-methyl), N-(2,6-Difluorphenyl)-8-fluor-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidin-2- sulfonamid (Florasulam), (R)-2-[4-(5-Trifluormethyl-pyridin-2-yl- oxy)-phenoxy]-propansäure-butylester (Fluazifop, -butyl, -P-butyl), 5- (4-Brom-1-methyl-5-trifluormethyl-1H-pyrazol-3-yl)-2-chlor-4-fluorbenzoesäure-i-propylester (Fluazolate), 4,5-Dihydro-3-methoxy-4- methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-1-H-1,2,4- triazol-1-carboxamid-Natriumsalz (Flucarbazone-sodium), N-(4- Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-1,3,4-thiadiazol-2-yloxy)-acetamid (Flufenacet), N-(2,6-Difluor-phenyl)-5-methyl-1,2,4- triazolo[1,5-a]-pyrimidin-2-sulfonamid (Flumetsulam), Pentyl-[2- chlor-4-fluor-5-(1, 3, 4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)- phenoxy]-acetat (Flumiclorac-pentyl), 2-[7-Fluor-3,4-dihydro-3-oxo- 4-(2-propinyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-iso- indol-1,3-dion (Flumioxazin), 2-[4-Chlor-2-fluor-5-[(1-methyl-2-propinyl)-oxy]-phenyl]-4,5,6,7-tetrahydro-1H-isoindol-1,3(2H)-dion (Flumipropyn), 3-Chlor-4-chlormethyl-1-(3-trifluormethyl-phenyl)-2- pyrrolidinon (Fluorochloridone), 5-(2-Chlor-4-trifluormethylphenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofen-ethyl), 1-(4-Chlor-3-(2,2,3,3,3-pentafluor-propoxymethyl)- phenyl)-5-phenyl-1H-1,2,4-triazol-3-carboxamid (Flupoxam), 1-Isopropyl-2-chlor-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluormethyl- 1(2H)-pyrimidyl)-benzoat (Flupropacil), N-(4,6-Dimethoxypyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-ylsulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methyl-sodium), 9- Hydroxy-9H-fluoren-9-carbonsäure (Flurenol), (4-Amino-3,5-dichlor- 6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1-methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5- Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)-furanon (Flurtamone), Methyl-[(2-chlor-4-fluor-5-(tetrahydro-3-oxo-1H,3H- [1,3,4]-thiadiazolo- [3,4-a]-pyridazin-1-yliden)-amino-phenyl]-thioacetat (Fluthiacet-methyl), 5-(2-Chlor-4-trifluormethyl-phenoxy)-N- methylsulfonyl-2-nitro-benzamid (Fomesafen), 2-[[[[(4,6-Dimethoxy- 2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-formylamino- N,N-dimethyl-benzamid (Foramsulfuron), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), (R)-2-[4-(3-Chlor-5-trifluormethyl-pyridin-2-yl-oxy)-phenoxy]-propansäure (-methylester, -2-ethoxy-ethylester, -butylester) (Haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-Cyclohexyl-6-dimethylamino-1-methyl-1,3,5- triazin-2,4(1H,3H)-dion (Hexazinone), Methyl-2-(4,5-dihydro-4- methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5- oxo-1H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)- 5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro- 4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4-methyl-4-i-propyl-5-oxo-1H- imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4,6- Dimethoxy-pyrimidin-2-yl)-N'-(2-chlor-imidazo [1,2-a]-pyridin-3-yl- sulfonyl)-harnstoff (Imazosulfuron), N-(4-Methoxy-6-methyl-1,3,5- triazin-2-yl)-N'-(5-iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff- Natriumsalz (Iodosulfuron-methyl-sodium), 4-Hydroxy-3,5-diiodbenzonitril (Ioxynil), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3-(1-Ethyl-1-methyl-propyl)-isoxazol-5-yl)- 2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2-methylsulfonylphenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5- Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethylphenyl)-methanon (Isoxaflutole), 2-[2-[4-[3,5-Dichlor-2-pyridinyl)- oxy]-phenoxy]-1-oxo-propyl]-isoxazolidin (Isoxapyrifop), (2-Ethoxy- 1-methyl-2-oxo-ethyl)-5-(2-chlor-4-trifluormethyl-phenoxy)-2-nitrobenzoat (Lactofen), N'-(3,4-dichlor-phenyl)-N-methoxy-N-methylharnstoff (Linuron), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2-(2-Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6- Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4- [[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 2-(4-Methylsulfonyl-2-nitro-benzoyl)-1,3-cyclohexandion (Mesotrione), 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-on (Metamitron), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl- methyl)-acetamid (Metazachlor), N'-(4-(3,4-Dihydro-2-methoxy- 2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N- methylharnstoff (Metobenzuron), N'-(4-Brom-phenyl)-N-methoxy-Nmethylharnstoff (Metobromuron), (S)-2-Chlor-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methyl-ethyl)-acet-amid (Metolachlor, S- Metolachlor), N-(2,6-Dichlor-3-methyl-phenyl)-5,7-dimethoxy-1,2,4- triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam), N'-(3-Chlor-4- methoxy-phenyl)-N,N-dimethyl-harnstoff (Metoxuron), 4-Amino-6- tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), N-(4- Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), S-Ethyl-hexahydro-1H- azepin-1-carbothioat (Molinate), 2-(2-Naphthyloxy)-N-phenyl-propanamid (Naproanilide), N-Butyl-N'-(3,4-dichlor-phenyl)-N-methyl-harnstoff (Neburon), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl)-harnstoff (Nicosulfuron), 4-Chlor-5- methylamino-2-(3-trifluormethyl-phenyl)-3(2H)pyridazinon (Norflurazon), S-(2-Chlor-benzyl)-N,N-diethyl-thiocarbamat (Orbencarb), 4- Dipropylamino-3,5-dinitro-benzensulfonamid (Oryzalin), 3-[2,4-Dichlor-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-on (Oxadiargyl), 3-[2,4-Dichlor-5-(1-methyl-ethoxy)-phenyl-5-(t-butyl)- 1,3,4-oxadiazol-2(3H)-on (Oxadiazon), N-(4,6-Dimethyl-pyrimidin-2- yl)-N'-(2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl)-harnstoff (Oxasulfuron), 3-[1-(3,5-Dichlor-phenyl)-1-i-propyl]-2,3-dihydro-6- methyl-5-phenyl-4H-1,3-oxazin-4-on (Oxaziclomefone), 2-Chlor-1- (3-ethoxy-4-nitro-phenoxy)-4-trifluormethyl-benzen (Oxyfluorfen), 1,1'-Dimethyl-4,4'-bipyridinium (Paraquat), 1-Amino-N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), 4-(t-Butyl)- N-(1-ethyl-propyl)-2,6-dinitro-benzenamin (Pendralin), 3-(4-Chlor-5- cyclopentyloxy-2-fluor-phenyl)-5-(1-methyl-ethyliden)-2,4-oxazolidin-dion (Pentoxazone), 4-Amino-3,5,6-trichlor-pyridin-2-carbonsäure (Picloram), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin- 2-carboxamid (Picolinafen), S-[2-(2-Methyl-1-piperidinyl)-2-oxoethyl]-O,O-dipropyl-phosphorodithioat (Piperophos), 2-Chlor-N-(2,6- diethyl-phenyl)-N-(2-propoxyethyl)-acetamid (Pretilachlor), N-(4,6- Bis-difluormethoxy-pyrimidin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Primisulfuron-methyl), 1-Chlor-N-[2-chlor-4- fluor-5-[(6S,7aR)-6-fluor-tetrahydro-1,3-dioxo-1 H-pyrrolo[1,2-c]- imidazol-2(3H)-yl]-phenyl]-methansulfonamid (Profluazol), 2-Chlor- N-isopropyl-N-phenyl-acetamid (Propachlor), N-(3,4-Dichlorphenyl)-propanamid (Propanil), (R)-[2-[[(1-Methyl-ethyliden)- amino]-oxy]-ethyl]-2-[4-(6-chlor-2-chinoxalinyloxy)-phenoxy]-propanoat (Propaquizafop), 2-Chlor-N-(2-ethyl-6-methyl-phenyl)-N-[(1- methyl-ethoxy)-methyl]-acetamid (Propisochlor), 2-[[[(4,5-Dihydro-4- methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)-carbonyl]-amino]- sulfonyl]-benzoesäure-methylester-Natriumsalz (Propoxycarbazonesodium), S-Phenylmethyl-N,N-dipropyl-thiocarbamat (Prosulfocarb), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluorpropyl)-phenylsulfonyl)-harnstoff (Prosuliron), Ethyl-[2-Chlor-5-(4- chlor-5-difluormethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluor-phenoxy]- acetat (Pyraflufen-ethyl), 1-(3-Chlor-4,5,6,7-tetrahydro-pyrazolo[1,5- a]pyridin-2-yl)-5-(methyl-2-propinylamino)-1H-pyrazol-4-carbonitril (Pyraclonil, Pyrazogyl), 4-(2,4-Dichlor-benzoyl)-1,3-dimethyl-5-(4- methyl-phenylsulfonyloxy)-pyrazol (Pyrazolate), 4-(2,4-Dichlorbenzoyl)-1,3-dimethyl-5-(phenylcarbonylmethoxy)-pyrazol (Pyrazoxyfen), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl-1- methyl-pyrazol-5-yl-sulfonyl)-harnstoff (Pyrazosulfuron-ethyl), Diphenylmethanon-O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)- benzoyl]-oxim (Pyribenzoxim), O[3-(1,1-Dimethyl-ethyl)-phenyl]-(6- methoxy-2-pyridinyl)-methylthiocarbamat (Pyributicarb), 6-Chlor-3- phenyl-4-pyridazinol (Pyridafol), O-(6-Chlor-3-phenyl-pyridazin-4- yl)-S-octyl-thiocarbonat (Pyridate), 6-Chlor-3-phenyl-pyridazin-4-ol (Pyridatol), 7-[(4,6-Dimethoxy-2-pyrimidinyl)-thio]-3-methyl-1(3H)- isobenzofuranon (Pyrifialid), 2-(4,6-Dimethoxy-pyrimidin-2-yl-oxy)- benzoesäure-methylester (Pyriminobac-methyl), 2-Chlor-6-(4,6-dimethoxy-pyrimidin-2-ylthio)-benzoesäure-Natriumsalz (Pyrithiobacsodium), 3,7-Dichlor-chinolin-8-carbonsäure (Quinchlorac), 7-Chlor- 3-methyl-chinolin-8-carbonsäure (Quimnerac), 2-[4-(6-Chlor-2-chinoxalinyloxy)-phenoxy]-propansäure (-ethylester, -tetrahydro-2- furanyl-methylester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N-(4,6- Dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-harnstoff (Rimsulfuron), 2-(1-Ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-on (Sethoxydim), 6-Chlor-2,4-bisethylamino-1,3,5-triazin (Simazin), 2-(2-Chlor-4-methylsulfonylbenzoyl)-cyclohexan-1,3-dion (Sulcotrione), 2-(2,4-Dichlor-5-methylsulfonylamino-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H- 1,2,4-triazol-3-on (Sulfentrazone), Methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-benzoate (Sulfometuronmethyl), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo [1,2- a]pyridin-3-sulfonamid (Sulfosulfuron), 6-Chlor-4-ethylamino-2-tertbutylamino-1,3,5-triazin (Terbuthylazine), 2-tert-Butylamino-4-ethylamino-6-methylthio-1,3,5-triazin (Terbutryn), 2-Chlor-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamid (Thenylchlor), 2-Difluormethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methylpropyl)-6-trifluormethyl-pyridin-3-carbonsäure-methylester (Thiazopyr), 6-(6,7-Dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c]-1,2,4-thiadiazol-3-ylidenamino)-7-fluor-4-(2-propinyl)-2H-1,4-benzoxazin-3(4H)- on (Thidiazimin), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2- methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuronmethyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-on (Tralkoxydim), S-(2,3,3-Trichlor-2- propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)-phenylsulfonyl]- harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6-methyl-1,3,5- triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), (3,5,6-Trichlor)-pyridin-2-yl-oxy-essigsäure (Triclopyr), 2-(3,5-Dichlor-phenyl)-2-(2,2,2-trichlor-ethyl)-oxiran (Tridiphane), N-[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3- (2,2,2-trifluor-ethoxy)-2-pyridinsulfonamid-Natriumsalz (Trifloxysulfuron), 1-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethyl-benzol (Trifluralin), N-[4-Dimethylamino-6-(2,2,2-trifluor-ethoxy)-1,3,5- triazin-2-yl]-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Triflusulfuron-methyl), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2- yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), N- [[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N- methylsulfonyl-amino])-2-pyridinsulfonamid, (vgl. WO-A-92/10660), 4-[4,5-Dihydro-4-methyl-5-oxo-(3-trifluormethyl)-1H-1,2,4-triazol-1- yl]-2-[(ethylsulfonyl)amino]-5-fluorbenzencarbothioamid (vgl. WO- A-95/30661), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3- (trifluormethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5- fluoro- (CAS-Nummer 173980-17-1, HWH4991) und 2-Chloro-N-[1- [2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-1 H-pyrazol-5-yl]- propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599).
("Wirkstoffe der Gruppe 3"),
sowie gegebenenfalls zusätzlich
α-(1,3-Dioxolan-2-yl-methoximino)-phenylacetonitril (Oxabetrinil), α- (Cyanomethoximino)-phenylacetonitril (Cyometrinil), 4-Chlor-N- (1,3-dioxolan-2-yl-methoxy)-α-trifluor-acetophenonoxim (Fluxofenim), 4,6-Dichlor-2-phenylpyrimidin (Fenclorim), 4-Dichloracetyl- 3,4-dihydro-3-methyl-2H-1,4-benzoxazin (Benoxacor), 5-Chlorchinoxalin-8-oxy-essigsäure-(1-methyl-hexylester) (Cloquintocet), 2,2-Dichlor-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)- acetamid (DKA-24), 1,8-Naphthalsäureanhydrid, 1-(2,4-Dichlorphenyl)-5-trichlormethyl-1H-1,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), 2-Chlor-4-trifluormethyl-thiazol-5-carbonsäurephenylmethylester (Flurazole), 3-Dichloracetyl-5-(2-furanyl)-2,2- dimethyl-oxazolidin (Furilazole, MON-13900), 4-Dichloracetyl-1- oxa-4-aza-spiro[4.5]-decan (AD-67), 2-Dichlormethyl-2-methyl-1,3- dioxolan (MG-191), 2,2-Dichlor-N-(1,3-dioxolan-2-yl-methyl)-N-(2- propenyl)-acetamid (PPG-1292), 2,2-Dichlor-N,N-di-2-propenyl-acetamid (Dichlormid), N-(4-Methyl-phenyl)-N'-(1-methyl-1-phenylethyl)-harnstoff (Dymron), 1-Dichloracetyl-hexahydro-3,3,8a- trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-on (BAS-145138), N-(2- Methoxy-benzoyl)-4-(methylaminocarbonylamino)-benzolsulfonamid, Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifenethyl), (4-Chlor-2-methylphenoxy)-essigsäure (MCPA), 2-(4-Chlor-2- methylphenoxy)-propionsäure (Mecoprop), Diethyl-1-(2,4- dichlorophenyl)-4,5-dihydro-5-methyl-1 H-pyrazol-3,5-dicarboxylat (Mefenpyr-diethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate
("Wirkstoffe der Gruppe 4").
in which
R is hydrogen, -CH 2 CH 2 S (O) n R 1 (where R 1 is C 1 -C 4 alkyl and n is 0, 1 or 2) or
stands,
in which
R 2 represents hydrogen, halogen, cyano, phenyl, C 1 -C 8 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, phenyl-C 1 -C 4 -alkylaminocarbonyl, where the phenyl group may optionally be substituted by halogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy, furylmethylaminocarbonyl or phenyl, and
R 3 for phenyl optionally substituted by halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or allyloxy, for amino optionally substituted by C 1 -C 4 alkyl, phenoxy, benzyloxy or acetoxy stands for C 1 -C 4 alkylthio or for the grouping -COR 4 , where R 4 stands for C 1 -C 4 alkoxy, C 1 - C 4 alkyl, benzyloxy or benzylamino,
A represents chlorine or methoxy and
D and E, which may be the same or different, represent hydrogen, halogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy or C 1 -C 8 alkoxy substituted by halogen,
and / or a salt of a compound of formula (I)
("Active substances of group 1"),
and
Methyl 2 - [[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino] sulfonyl] benzoic acid, sodium Salt (Propoxycarbazone-sodium) of the formula
and
4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [[2- (trifluoromethoxy) phenyl] sulfonyl] -1H-1,2,4-triazole-1-carboxamide, sodium salt (Flucarbazone-sodium) of the formula
("Active substances of group 2"),
such as
2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid sodium salt (Acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxybenzenamine (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethylphenyl) -acetamide (alachlor), N-ethyl- N'-i-propyl-6-methylthio-1,3,5-triazine-2,4-diamine (ametryn), 4-amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro- 3- (1-methyl-ethyl) -5-oxo-1H-1,2,4-triazole-1-carboxamide (amicarbazone), N- (4,6-dimethoxypyrimidin-2-yl) -N'- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1,2,4-triazol-3-amine (amitrole), S- [2 - [(4-chlorophenyl) - (1 -isopropyl) -amino] - 2-oxo-ethyl] -O, O-dimethyl-phosphorodithioate (anilofos), 6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2,4-triazolo- [4,3-a] pyridine-3 (2H) -one (azafenidin), N- (4,6-dimethoxypyrimidin-2-yl) - N '- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) -1H-pyrazole- 5-ylsulfonyl] harnstof f (azimsulfuron), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2-oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl- N-ethyl-2,6-dinitro-4-trifluoromethylbenzenamine (benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulfonate (benfuresate), N- (4,6-dimethoxypyrimidin-2-yl ) -N'- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuronmethyl), S - [(4-chlorophenyl) methyl] diethylthiocarbamate (benthiocarb, thiobencarb), 2- [2- [4- (3, 6-Dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinylphenoxymethyl] -5-ethyl-phenoxypropanoic acid methyl ester (benzfendizone), 3- (2-chloro-4-methylsulfonylbenzoyl) -4-phenylthio-bicyclo- [3.2.1] oct-3-en-2-one (benzobicyclone), 2 - [[4- (2,4-dichloro-3-methylbenzoyl) -1,3-dimethyl- 1H-pyrazol-5-yl] - oxy] -1- (4-methylphenyl) ethanone (benzofenap), ethyl N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate (benzoylprop- ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) -2-nitro-benzo at (bifenox), 5-bromo-6-methyl-3- (1-methylpropyl) -2.4 (1H, 3H) pyrimidinedione (bromoacil), 2-bromo-3,3-dimethyl-N- (1-methyl -1-phenyl-ethyl) -butanamide (bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde-O- (2,4-dinitro-phenyl) -oxime (bromofenoxime), 3,5-dibromo-4- hydroxy-benzonitrile (bromoxynil), N-butoxymethyl-2-chloro-N- (2,6-diethyl-phenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2 , 6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid- [1,1-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (1 -Ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3- (1-oxo-butyl) phenyl] -2-cyclohexen-1-one (butroxydim), S-ethyl-bis - (2-methyl-propyl) -thiocarbamate (butylate), N, N-diethyl-3- (2,4,6-trimethyl-phenylsulfonyl) -1H-1,2,4-triazole-1-carboxamide (cafenstrole) , 2- [1 - [(3-chloro-2-propenyl) oxyimino] propyl] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1-one (Caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonylethyl) phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro -3H-1,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro-1- (3-methoxy-4-nitrophenoxy) benzene (chloromethoxyfen), 3-amino-2,5 -dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidin-2-yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) -urea (chlorimuron-ethyl), 1,3,5- Trichloro-2- (4-nitro-phenoxy) benzene (chloronitrofen), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl ) urea (chlorosulfuron), N '- (3-chloro-4-methylphenyl) -N, N-dimethylurea (chlorotoluron), 2-chloro-3- [2-chloro-5- (1.3 , 4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid, ethyl ester (cinidonethyl), exo-1-methyl-4-isopropyl-2- (2-methyl-phenyl-methoxy) -7-oxabicyclo- [2.2.1] -heptane (cinmethylin), N- (4,6-dimethoxy-1,3,5-triazin-2-yl) -N'- (2- (2-methoxyethoxy) phenylsulfonyl) urea (cinosulirone), 2- [1- [2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) - 1,3-cyclohexanedione (Clefoxydim), (E, E) - (+) - 2- [1 - [[(3-chloro-2-propenyl) -oxy] imino] propyl] -3-hydroxy-2 - cycl ohexen-1-one (clethodim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (clodinafop propargyl), 2 - (2,4-dichloro-3-methyl-phenoxy) -N-phenyl-propanamide (Clomeprop), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralide), methyl-3-chloro-2 - [(5 - ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) -amino] - benzoate (chlorosulam-methyl), N - [(2-chlorophenyl) -methyl] -N '- (1-methyl-1-phenyl-ethyl) -urea (cumyluron), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino) -1,3, 5-triazine (cyanazine), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (cyclosulfamuron), 2- (1-ethoximinobutyl) -3-hydroxy -5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen-1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] - butanoic acid propyl (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4- Dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy ] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) -5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine-2 - sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3 carboxamide (diflufenican), 2- [1 - [(3,5-difluorophenyl) amino carbonyl hydrazono] ethyl] pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1- phenyl-ethyl) -1-piperidine-carbothioate (dimepiperate), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (2-methoxy-ethyl) -acetamide (dimethachlor), N- (1, 2-dimethyl-propyl) -N'-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine (dimethametryn), (S-) 2-chloro-N- (2,4-dimethyl- 3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (S-) (dimethenamid), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6- (1 - methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -1,3,5-triazine (dimexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diamino -benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', 1'-c] pyrazinediium (diquat), S, S-dimethyl-2-difluoromethyl -4-i-butyl-6-trifluoromethylpyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) -N, N-dimethyl-urea (diuron), N- (4-methyl -phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron, Daimuron), 2- [2- (3-chlorophenyl) - oxiranylmethyl] -2-ethyl-1H-inden- 1,3 (2H) -dione (epropodane), S-ethyl-dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Esprocarb), N- Ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4-trifluoromethyl-benzenamine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro -5- (2-chloro-4-trifluoromethylphenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (ethoxysulfuron), N- (2,3-dichlorophenyl) -4-ethoxymethoxybenzamide (etobenzanide), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop - (P) -ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N -benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate (Flamprop -isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4- fluorophenoxy) -DL-alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [1,5-c] - butyl pyrimidin-2-sulfonamide (Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yloxy) phenoxy] propanoic acid (fluazifop, butyl, -P-butyl), 5- (4-Bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluorobenzoic acid i-propyl ester (fluazolates), 4,5-dihydro-3-methoxy-4 - methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1-H-1,2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium), N- (4-fluor -phenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy) acetamide (Flufenacet), N- (2,6-difluorophenyl) -5-methyl-1 , 2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), pentyl- [2-chloro-4-fluoro-5- (1, 3, 4,5,6,7-hexahydro -1,3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro-3-oxo 4- (2-propynyl) -2H- 1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5- [ (1-methyl-2-propynyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-1H-isoindole-1,3 (2H) -dione (flumipropyn), 3-chloro-4-chloromethyl- 1- (3-trifluoromethyl-phenyl) -2-pyrrolidinone (fluorochloridone), 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1- (4-chloro-3 - (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5 - (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidyl) benzoate (flupropacil), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-ylsulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3 , 5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5- methylamino-2-phenyl-4- (3-trifluormethy l-phenyl) -3 (2H) -furanone (Flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1,3,4] -thiadiazolo- [3,4-a] pyridazin-1-ylidene) aminophenyl] thioacetate (fluthiacet-methyl), 5- (2-chloro-4-trifluoromethylphenoxy) -N-methylsulfonyl-2-nitro-benzamide (Fomesafen), 2 - [[[((4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N-dimethyl-benzamide (foramsulfuron), 2 -Amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammmonium salt), (glyphosate, isopropylammonium), (R) -2- [4- (3rd -Chlor-5-trifluoromethyl-pyridin-2-yl-oxy) -phenoxy] -propanoic acid (-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl ), 3-Cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4 (1H, 3H) -dione (Hexazinone), methyl-2- (4,5-dihydro-4-methyl -4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo 1H-imidazole 2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) - 5- methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquine), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4, 6- Dimethoxy-pyrimidin-2-yl) -N '- (2-chloro-imidazo [1,2-a] -pyridin-3-yl-sulfonyl) -urea (imazosulfuron), N- (4-methoxy-6 -methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5- diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproturon), N- (3- (1-ethyl-1-methyl-propyl) -isoxazol-5-yl) - 2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methylsulfonylphenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethylphenyl) methanone (isoxaflutole), 2- [2- [4- [3,5-dichloro-2-pyridinyl) oxy] phenoxy] -1-oxo-propyl] isoxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2-oxo-ethyl) ) -5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate (lactofen), N '- (3,4-dichlorophenyl) -N-methoxy-N-methylurea (Linuron), (4- Chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 2 - [[[[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4- [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (Mesosulfuron), 2- (4-methylsulfonyl-2-nitro-benzoyl) -1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-1,2,4-triazine-5 (4H ) -one (metamitron), 2-chloro-N- (2,6-dimethyl-phenyl) -N- (1H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N '- (4- (3rd , 4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy) phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4- Bromophenyl) -N-methoxy-Nmethylurea (metobromuron), (S) -2-chloro-N- (2-ethyl-6-methylph enyl) -N- (2-methoxy-1-methyl-ethyl) -acet-amide (metolachlor, S-metolachlor), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy- 1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4-methoxyphenyl) -N, N-dimethyl-urea (metoxuron), 4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1,3,5-triazine -2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-1H-azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N -phenyl-propanamide (naproanilide), N-butyl-N '- (3,4-dichlorophenyl) -N-methyl-urea (neburon), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), 4-chloro-5-methylamino-2- (3-trifluoromethyl-phenyl) -3 (2H) pyridazinone (norflurazone), p - (2-Chloro-benzyl) -N, N-diethylthiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy ) -phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5- (1-methylethoxy) phenyl-5- (t-butyl) - 1,3,4-oxadiazol-2 (3H) -one (oxadiazon), N- ( 4,6-Dimethyl-pyrimidin-2-yl) -N '- (2-oxetan-3-yl-oxycarbonyl-phenylsulfonyl) -urea (oxasulfuron), 3- [1- (3,5-dichlorophenyl) - 1-i-propyl] -2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1- (3-ethoxy-4-nitro -phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), 1,1'-dimethyl-4,4'-bipyridinium (paraquat), 1-amino-N- (1-ethylpropyl) -3,4-dimethyl-2, 6-dinitro-benzene (pendimethalin), 4- (t-butyl) - N- (1-ethyl-propyl) -2,6-dinitro-benzenamine (pendralin), 3- (4-chloro-5-cyclopentyloxy-2 -fluorophenyl) -5- (1-methylethylidene) -2,4-oxazolidinedione (pentoxazone), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) pyridine-2-carboxamide (picolinafen), S- [2- (2-methyl-1-piperidinyl) -2-oxoethyl] -O, O -dipropyl-phosphorodithioate (Piperophos), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxyethyl) -acetamide (pretilachlor), N- (4,6-bis-difluorometho xy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), 1-chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-1,3-dioxo-1 H-pyrrolo [1,2-c] imidazole-2 (3H) -yl] phenyl] methanesulfonamide (profluazole), 2-chloro-N-isopropyl -N-phenyl-acetamide (propachlor), N- (3,4-dichlorophenyl) propanamide (propanil), (R) - [2 - [[(1-methylethylidene) - amino] -oxy] -ethyl] -2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoate (propaquizafop), 2-chloro-N- (2-ethyl-6-methylphenyl) -N - [(1-methyl- ethoxy) methyl] acetamide (propisochlor), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) - carbonyl] amino] sulfonyl] benzoic acid methyl ester sodium salt (propoxycarbazone sodium), S-phenylmethyl-N, N-dipropyl thiocarbamate (prosulfocarb), N- (4-methoxy-6-methyl-1,3,5- triazin-2-yl) -N '- (2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (prosulirone), ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1 -methyl-1H-pyrazol-3-yl) -4-fluoro-phenoxy] - acetate (pyraflufen-ethyl), 1- (3-chloro-4, 5,6,7-tetrahydro-pyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -1H-pyrazole-4-carbonitrile (pyraclonil, pyrazogyl), 4- (2nd , 4-dichlorobenzoyl) -1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5- (phenylcarbonylmethoxy) -pyrazole (pyrazoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), Diphenylmethanone-O- [2,6-bis- (4,6-dimethoxypyrimidin-2-yloxy) benzoyl] oxime (pyribenzoxime), O [3- (1,1-dimethylethyl) phenyl ] - (6-methoxy-2-pyridinyl) methylthiocarbamate (pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol), O- (6-chloro-3-phenyl-pyridazin-4-yl) - S-octyl-thiocarbonate (pyridate), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) thio] -3-methyl-1 ( 3H) -isobenzofuranone (pyrifialide), 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidine- 2-ylthio) benzoic acid Natr Ium salt (pyrithiobacsodium), 3,7-dichloro-quinoline-8-carboxylic acid (Quinchlorac), 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quimnerac), 2- [4- (6-chloro-2-quinoxalinyloxy ) -phenoxy] -propanoic acid (-ethyl ester, -tetrahydro-2-furanyl-methyl ester) (quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidin-2-yl ) -N '- (3-ethylsulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfuron), 2- (1-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1- on (Sethoxydim), 6-chloro-2,4-bisethylamino-1,3,5-triazine (simazine), 2- (2-chloro-4-methylsulfonylbenzoyl) -cyclohexane-1,3-dione (Sulcotrione), 2 - (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone), methyl 2- [ [[[((4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoates (sulfometuronmethyl), N-phosphonomethylglycine trimethyl sulfonium (sulfosates), N- (4,6- Dimethoxy-pyrimidin-2-yl) -N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-eth ylamino-2-tertbutylamino-1,3,5-triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N- (2nd , 6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- ( 2-methylpropyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2,1-c] -1, 2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) -2H-1,4-benzoxazin-3 (4H) - one (thidiazimin), N- (4-methoxy-6- methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuronmethyl), 2- (ethoximino-propyl) -3-hydroxy-5 - (2,4,6-trimethylphenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallate), N- (4-methoxy- 6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy- 6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) pyridin-2-yloxy acetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloroethyl) oxirane (Tridiphane), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron), 1 -Amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -1,3,5 - triazin-2-yl] -N '- (2-methoxycarbonylphenylsulfonyl) urea (triflusulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) - N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), N- [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (N-methyl-N-methylsulfonylamino ]) - 2-pyridine sulfonamide, (cf. WO-A-92/10660), 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2- [ (ethylsulfonyl) amino] -5-fluorobenzenecarbothioamide (see WO-A-95/30661), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1 , 2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5- fluoro- (CAS number 173980-17-1, HWH4991) and 2-chloro-N- [1- [2, 6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propanecarboxamide (CAS number 121750-17-2; SLA5599).
("Active substances of group 3"),
as well as, if necessary, additionally
α- (1,3-Dioxolan-2-yl-methoximino) phenylacetonitrile (oxabetrinil), α- (cyanomethoximino) phenylacetonitrile (cyometrinil), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy ) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 5 Chloroquinoxaline-8-oxyacetic acid (1-methylhexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl ) - acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1- oxa-4-aza-spiro [4.5] decane (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N- (1,3- dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichlormid), N - (4-methyl-phenyl) -N '- (1-methyl-1-phenylethyl) urea (Dymron), 1-dichloroacetyl-hexahydro-3,3,8-trimethylpyrrolo [1,2-a] pyrimidine - 6 (2H) -one (BAS-145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) benzenesulfonamide, ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifenethyl) , (4-Chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (Mecoprop), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro -5-methyl-1 H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives
("Active substances of group 4").
in welcher
R für Wasserstoff oder
steht, wobei
R2 bevorzugt für Wasserstoff, Chlor, Cyano, Phenyl, C1-C8-Alkyl, Methoxy, Methylthio, C1-C2-Alkoxycarbonyl, Propylaminocarbonyl, Dimethylaminocarbonyl, Benzylaminocarbonyl (wobei die Benzylgruppe gegebenenfalls durch Chloro, Methyl oder Methoxy substituiert ist), 2'-Phenylethylaminocarbonyl oder Furylmethylaminocarbonyl steht, und
R3 bevorzugt für gegebenenfalls durch Chlor, Fluor, Cyano, Nitro, Methyl, Methoxy, Ethoxy, Butoxy, Allyloxy, Methylthio, Dimethylamino, Phenoxy, Benzyloxy oder Acetoxy substituiertes Phenyl oder für -COR4 steht, worin R4 für Methoxy, Ethoxy, Methyl, Benzyloxy oder Benzylamino steht,
A bevorzugt für Chlor oder Methoxy steht und
D und E, die gleich oder unterschiedlich sein können, bevorzugt für Wasserstoff, Methoxy oder Ethoxy stehen.
R2 steht besonders bevorzugt für Wasserstoff, Methyl, Methylthio, Cyano, Methoxycarbonyl oder Phenyl.
R3 steht besonders bevorzugt für gegebenenfalls durch Methyl oder Methoxy substituiertes Phenyl.
A steht besonders bevorzugt für Methoxy.
D und E stehen besonders bevorzugt für Methoxy.
R2 steht ganz besonders bevorzugt für Phenyl.
R3 steht ganz besonders bevorzugt für Phenyl. 2. Herbicidal compositions according to claim 1, characterized in that they contain a compound of the formula (I) as active ingredients in group 1,
in which
R for hydrogen or
stands where
R 2 is preferably hydrogen, chlorine, cyano, phenyl, C 1 -C 8 alkyl, methoxy, methylthio, C 1 -C 2 alkoxycarbonyl, propylaminocarbonyl, dimethylaminocarbonyl, benzylaminocarbonyl (the benzyl group being optionally substituted by chloro, methyl or methoxy ), 2'-phenylethylaminocarbonyl or furylmethylaminocarbonyl, and
R 3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR 4 , where R 4 represents methoxy, ethoxy, Is methyl, benzyloxy or benzylamino,
A preferably represents chlorine or methoxy and
D and E, which may be the same or different, are preferably hydrogen, methoxy or ethoxy.
R 2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
R 3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
A particularly preferably represents methoxy.
D and E are particularly preferably methoxy.
R 2 very particularly preferably represents phenyl.
R 3 very particularly preferably represents phenyl.
4-Amino-N-(1,1-Dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-1H- 1,2,4-triazol-1-carboxamid (Amicarbazone), N-(4,6-Dimethoxy-pyrimidin-2- yl)-N'-(N-methyl-N-methylsulfonyl-sulfamoyl)-harnstoff (Amidosulfuron), N-Benzyl-2-(4-fluor-3-trifluormethyl-phenoxy)-butanamid (Beflubutamid), 3- i-Propyl-1H-2,1,3-benzothiadiazin-4(3H)-on (Bentazon), Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), 3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4-difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), 2-Chlor-3-[2-chlor-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propansäure-ethylester (Cinidon-ethyl), (R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), 3,6-Dichlor-pyridin-2-carbonsäure (Clopyralid), 2,4-Dichlor-phenoxyessigsäure (2,4-D),3,6-Dichlor-2-methoxybenzoesäure (Dicamba), (R)-2-(2,4-Dichlor-phenoxy)-propansäure (Dichlorprop-P), Methyl-2-[4-(2,4-dichlor-phenoxy)-phenoxy]-propanoat (Diclofopmethyl), 1,2-Dimethyl-3,5-diphenyl-1H-pyrazolium-methylsulfat (Difenzoquat), N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-phenoxysulfonyl)-harnstoff (Ethoxysulfuron), (R)-Ethyl-2-[4-(6-chlor-benzoxazol- 2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl), 4-(2-Chlor-phenyl)-N- cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-carboxamid (Fentrazamide), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-DL-alaninat (Flamprop-isopropyl), Isopropyl-N-benzoyl-N-(3-chlor-4-fluro-phenyl)-L-alaninat (Flamprop-isopropyl-L), Methyl-N-benzoyl-N-(3-chlor-4-fluor-phenoxy)- DL-alaninat (Flamprop-methyl), N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy- [1,2,4]-triazolo-[1,5-c]-pyrimidin-2-sulfonamid (Florasulam), 5-(4-Brom-1- methyl-5-trifluormethyl-1H-pyrazol-3-yl)-2-chlor-4-fluor-benzoesäure-i- propylester (Fluazolate), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluormethoxy-phenyl)-sulfonyl]-1-H-1,2,4-triazol-1-carboxamid-Natriumsalz (Flucarbazone-sodium), N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl- 1,3,4-thiadiazol-2-yl-oxy)-acetamid (Flufenacet), 5-(2-Chlor-4-trifluormethylphenoxy)-2-nitro-benzoesäure-ethoxycarbonylmethylester (Fluoroglycofenethyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfuron-methylsodium), (4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1-methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 5-Methylamino-2-phenyl-4-(3-trifluormethyl-phenyl)-3(2H)- furanon (Flurtamone), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium), Methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo- 1H-imidazol-2-yl)-5-methyl-pyridin-3-carbonsäure (Imazamethapyr), 2-(4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxymethylpyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5- oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro- 4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5-iod-2- methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuronmethyl-sodium), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil), N,N-Dimethyl- N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon), N-(3-(1-Ethyl-1-methylpropyl)-isoxazol-5-yl)-2,6-dimethoxy-benzamid (Isoxaben), (4-Chlor-2- methylsulfonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanon (Isoxachlortole), (5-Cyclopropyl-isoxazol-4-yl)-(2-methylsulfonyl-4-trifluormethylphenyl)-methanon (Isoxaflutole), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop), 2-(2- Benzthiazolyloxy)-N-methyl-N-phenyl-acetamid (Mefenacet), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]methyl]-benzoesäure-methylester (Mesosulfuron), 4-Amino- 3-methyl-6-phenyl-1,2,4-triazin-5(4H)-on (Metamitron), N-(2,6-Dichlor-3- methyl-phenyl)-5,7-dimethoxy-1,2,4-triazolo [1,5-a]-pyrimidin-2-sulfonamid (Metosulam), 4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), 1-Amino-N-(1- ethyl-propyl)-3,4-dimethyl-2,6-dinitro-benzol (Pendimethalin), N-(4-Fluorphenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2-carboxamid (Picolinafen), N- (3,4-Dichlor-phenyl)-propanamid (Propanil), Ethyl-[2-Chlor-5-(4-chlor-5-difluormethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluor-phenoxy]-acetat (Pyraflufen-ethyl), 2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione), N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate), N- (4,6-Dimethoxy-pyrimidin-2-yl)-N'-(2-ethylsulfonyl-imidazo [1,2-a]pyridin- 3-sulfonamid (Sulfosulfuron), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'- (2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), 2-(Ethoximino-propyl)-3-hydroxy-5-(2,4,6-trimethyl-phenyl)-2-cyclohexen- 1-on (Tralkoxydim), S-(2,3,3-Trichlor-2-propenyl)-diisopropylcarbamothioat (Triallate), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-[2-(2-chlorethoxy)-phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuron-methyl), 1-Amino-2,6-dinitro-N,N-dipropyl-4-trifluormethylbenzol (Trifluralin), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-yl)-N'- (2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron), Phenylcarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H-1,2,4-triazol-1- yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS-Nummer 173980-17-1, HWH4991) und (2-Chloro-N-[1-[2,6-dichloro-4-(difluoromethyl)phenyl]-4- nitro-1H-pyrazol-5-yl]-propancarbonsäureamid (CAS-Nummer 121750-17-2; SLA5599). 3. Herbicidal composition according to claim 1 or 2, characterized in that it contains, as an active ingredient in group 3, one or more active ingredients from the following group of active ingredients:
4-amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro-3- (1-methyl-ethyl) -5-oxo-1H-1,2,4-triazole-1-carboxamide ( Amicarbazones), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N-benzyl-2- (4-fluoro- 3-trifluoromethylphenoxy) butanamide (beflubutamide), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl-5- (2,4-dichlorophenoxy) ) -2-nitro-benzoate (bifenox), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Carfentrazone-ethyl), N- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methylphenyl) -N, N-dimethylurea ( Chlorotoluron), 2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2 -propanoic acid ethyl ester (cinidon-ethyl), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) -phenoxy-propanoate (clodinafop-propargyl ), 3,6-dichloropyride in-2-carboxylic acid (clopyralide), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4-dichloro- phenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofopmethyl), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium -methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (diflufenican), N- (4,6-dimethoxy-pyrimidine-2- yl) -N '- (2-ethoxy-phenoxysulfonyl) urea (ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop - (P) -ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N -benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate (Flamprop-isopropyl), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate ( Flamprop-isopropyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) - DL-alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8- fluoro-5-methoxy- [1,2,4] triazolo- [1,5-c] pyrimidine-2 -sulfonamide (florasulam), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro-benzoic acid i-propyl ester (fluazolates), 4.5 -Dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1-H-1,2,4-triazole-1-carboxamide sodium salt (Flucarbazone-sodium ), N- (4-fluorophenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), 5- (2-chloro 4-trifluoromethylphenoxy) -2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofenethyl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl- sulfonyl) urea sodium salt (flupyrsulfuron-methylsodium), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, - 1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) - furanone (flurtamone), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammmon ium salt), (glyphosate, isopropylammonium), methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz- methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4th , 5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethylpyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl- 4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquine), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H -imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5 -iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuronmethyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), N- (3- (1-ethyl-1-methylpropyl) isoxazol-5-yl) -2,6-dimethoxybenzamide (isoxaben), (4-chloro-2-methylsulfonylphenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5-cy clopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethylphenyl) methanone (isoxaflutole), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2- methyl-phenoxy) -propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 2 - [[[((4,6-dimethoxy-2-pyrimidinyl) amino ] -carbonyl] -amino] -sulfonyl] -4 - [[(methylsulfonyl) -amino] methyl] -benzoic acid methyl ester (mesosulfuron), 4-amino-3-methyl-6-phenyl-1,2,4-triazine -5 (4H) -one (metamitron), N- (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine - 2-sulfonamide (metosulam), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl- 1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (metsulfuron-methyl), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl -2,6-dinitro-benzene (pendimethalin), N- (4-fluorophenyl) -6- (3-trifluoromethyl-phenoxy) -pyridine-2-carboxamide (picolinafen), N- (3,4-dichlorophenyl) -propanamide (propanil), ethyl- [2-chloro-5- (4-chloro-5-difluorom ethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] acetate (pyraflufen-ethyl), 2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (Sulcotrione), N-phosphonomethyl-glycine trimethylsulfonium (sulfosate), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3 -sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N'- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron -methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen- 1-one (tralkoxydim), S- (2,3,3- Trichloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl ), 1-Amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethylbenzene (trifluralin), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (Tritos sulfuron), phenylcarbothiamide-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5-fluoro- (CAS number 173980-17-1, HWH4991) and (2-chloro-N- [1- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H -pyrazol-5-yl] -propane carboxamide (CAS number 121750-17-2; SLA5599).
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonylsulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-1,3,5- triazin-2-yl)-N'-(2-chlor-phenylsulfonyl)-harnstoff (Chlorsulfuron), N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(3-methoxycarbonyl-6-trifluormethyl-pyridin-2-yl-sulfonyl)-harnstoff-Natriumsalz (Flupyrsulfitronmethyl-sodium), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(5- iod-2-methoxycarbonyl-phenylsulfonyl)-harnstoff-Natriumsalz (Iodosulfuron-methyl-sodium), 2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)- amino]-carbonyl]-amino]-sulfonyl]-4-[[(methylsulfonyl)-amino]- methyl]-benzoesäure-methylester (Mesosulfuron), N-(4-Methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Metsulfuron-methyl), N-(4,6-Dimethoxy-pyrimidin-2-yl)- N'-(2-ethylsulfonyl-imidazo[1,2-a]pyridin-3-sulfonamid (Sulfosulf uron), N-(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-thien-3-yl-sulfonyl)-harnstoff (Thifensulfuron-methyl), N- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-[2-(2-chlor-ethoxy)- phenylsulfonyl]-harnstoff (Triasulfuron), N-Methyl-N-(4-methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)- harnstoff (Tribenuron-methyl), N-(4-Methoxy-6-trifluormethoxy- 1,3,5-triazin-2-yl)-N'-(2-trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[1,2,4]-triazolo-[1,5-c]- pyrimidin-2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo [1,5-a]-pyrimidin-2-sulfonamid (Metosulam),
Methyl-2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2- yl)-4-methyl-benzoat (Imazamethabenz-methyl), 2-(4,5-Dihydro-4- methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridin-3- carbonsäure (Imazamethapyr), 2-(4,5-Dihydro-4-methyl-4-isopropyl- 5-oxo-1H-imidazol-2-yl)-5-methoxymethyl-pyridin-3-carbonsäure (Imazamox), 2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-chinolin-3-carbonsäure (Imazaquin), 2-(4,5-Dihydro-4- methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridin-3-carbonsäure (Imazethapyr),
N'-(3-Chlor-4-methyl-phenyl)-N,N-dimethyl-harnstoff (Chlortoluron), N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon),
4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin),
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione),
2-(4-Chlor-2-fluor-5-(2-chlor-2-ethoxycarbonyl-ethyl)-phenyl)-4- difluormethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-on (Carfentrazone-ethyl), Phenylcarbothiamid-, 4-[4,5-dihydro-4-methyl-5-oxo-3- (trifluormethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5- fluoro-(CAS-Nummer 173980-17-1, HWH4991),
3,5-Dibrom-4-hydroxy-benzonitril (Bromoxynil), 4-Hydroxy-3,5-diiod-benzonitril (Ioxynil),
(R)-(2-Propinyl)-2-[4-(5-chlor-3-fluor-pyridin-2-yl-oxy)-phenoxy-propanoat (Clodinafop-propargyl), Methyl-2-[4-(2,4-dichlor-phenoxy)- phenoxy]-propanoat (Diclofop-methyl), (R)-Ethyl-2-[4-(6-chlor-benzoxazol-2-yl-oxy)-phenoxy]-propanoat (Fenoxaprop-(P)-ethyl),
2,4-Dichlor-phenoxyessigsäure (2,4-D), (®2-(2,4-Dichlor-phenoxy)- propansäure (Dichlorprop-P), (4-Chlor-2-methyl-phenoxy)-essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-propionsäure (Mecoprop),
N-(2,4-Difluor-phenyl)-2-(3-trifluormethyl-phenoxy)-pyridin-3-carboxamid (Diflufenican), N-(4-Fluor-phenyl)-6-(3-trifluormethyl-phenoxy)-pyridin-2- carboxamid (Picolinafen),
N-(4-Fluor-phenyl)-N-i-propyl-2-(5-trifluormethyl-1,3,4-thiadiazol-2-yl- oxy)-acetamid (Flufenacet),
(2-Chloro-N-[1-[2,6-dichloro-4-(difluoromethyl)phenyl]-4-nitro-1H-pyrazol- 5-yl]-propancarbonsäureamid (CAS-Nummer 121750-12-2; SLA5599),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox),
2-Chlor-3-[2-chlor-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)- phenyl]-2-propansäure-ethylester (Cinidon-ethyl),
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1- methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl), 2-Amino-4-(hydroxymethylphosphinyl)-butansäure (-ammoniumsalz) (Glufosinate (-ammonium)), N-Phosphonomethyl-glycin (-isopropylammmoniumsalz), (Glyphosate, -isopropylammonium) oder N-Phosphonomethyl-glycin-trimethylsulfonium (Sulfosate).
N- (4,6-Dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3,5 - triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N- (4,6-dimethoxypyrimidin-2-yl) -N' - (3-methoxycarbonyl-6- trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfitronmethyl-sodium), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5- iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 2 - [[[[((4,6-dimethoxy-2-pyrimidinyl) - amino] carbonyl] amino] sulfonyl] - 4 - [[(methylsulfonyl) amino] methyl] benzoic acid methyl ester (mesosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2nd -methoxycarbonyl-phenylsulfonyl) - urea (metsulfuron-methyl), N- (4,6-dimethoxy-pyrimidin-2-yl) - N '- (2-ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (Sulfosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron- methyl), N- (4-methoxy-6-methyl-1 , 3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1 , 3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (tribenuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2 -yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron),
N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [1,5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam),
Methyl 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5- Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4 -isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo 1H-imidazol-2-yl) -quinolin-3-carboxylic acid (imazaquin), 2- (4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl) - 5-ethyl-pyridine-3-carboxylic acid (imazethapyr),
N '- (3-chloro-4-methyl-phenyl) -N, N-dimethyl-urea (chlorotoluron), N, N-dimethyl-N' - (4-isopropyl-phenyl) -urea (isoproturon),
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin),
2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione),
2- (4-chloro-2-fluoro-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4- triazol-3-one (carfentrazone-ethyl), phenylcarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl ] -2 - [(ethylsulfonyl) amino] -5- fluoro- (CAS number 173980-17-1, HWH4991),
3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil),
(R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxypropanoate (clodinafop-propargyl), methyl 2- [4- ( 2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop - (P) -ethyl),
2,4-dichlorophenoxyacetic acid (2,4-D), (®2- (2,4-dichlorophenoxy) propanoic acid (dichloroprop-P), (4-chloro-2-methylphenoxy) acetic acid ( MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop),
N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) -pyridine-2-carboxamide (picolinafen),
N- (4-fluoro-phenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet),
(2-Chloro-N- [1- [2,6-dichloro-4- (difluoromethyl) phenyl] -4-nitro-1H-pyrazol-5-yl] propane carboxamide (CAS number 121750-12-2; SLA5599 )
Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox),
2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl),
(4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 2-amino-4- (hydroxymethylphosphinyl) -butanoic acid (-ammonium salt) (glufosinate (-ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium) or N-phosphonomethyl-glycine- trimethylsulfonium (sulfosates).
5-Chlor-chinoxalin-8-oxy-essigsäure-(1-methylhexylester) (Cloquintocet), 1- (2,4-Dichlor-phenyl)-5-trichlormethyl-1H-1,2,4-triazol-3-carbonsäure-ethylester (Fenchlorazol-ethyl), Ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolcarboxylat (Isoxadifen-ethyl), (4-Chlor-2-methylphenoxy)-essigsäure (MCPA), 2- (4-Chlor-2-methylphenoxy)-propionsäure (Mecoprop), Diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylat (Mefenpyrdiethyl) und 2,4-Dichlorophenoxyessigsäure (2,4-D) und dessen Derivate. 5. Herbicidal composition according to one of claims 1 to 4, characterized in that it contains, as active ingredient in group 4, one or more active ingredients in the following group of active ingredients:
5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (cloquintocet), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4th Chloro-2-methylphenoxy) propionic acid (mecoprop), diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyrdiethyl) and 2, 4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.
2,6-Bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium), (Bispyribac-sodium, KIH 2023) der Formel
oder
Diphenyl-methanon-O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)- oxy]benzoyl]oxim (Pyribenzoxim) der Formel
sowie
sowie gegebenenfalls
2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium), (bispyribac-sodium, KIH 2023) of the formula
or
Diphenylmethanone-O- [2,6-bis [(4,6-dimethoxy-2-pyrimidinyl) oxy] benzoyl] oxime (pyribenzoxime) of the formula
such as
and if necessary
und
sowie
N-(4,6-Dimethoxy-pyrimidin-2-yl)-N'-(N-methyl-N-methylsulfonylsulfamoyl)-harnstoff (Amidosulfuron), N-(4-Methoxy-6-methyl-1,3,5- triazin-2-yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Metsulfuron-methyl), N-Methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2- yl)-N'-(2-methoxycarbonyl-phenylsulfonyl)-harnstoff (Tribenuronmethyl), N-(4-Methoxy-6-trifluormethoxy-1,3,5-triazin-2-yl)-N'-(2- trifluormethyl-phenylsulfonyl)-harnstoff (Tritosulfuron),
N-(2,6-Difluor-phenyl)-8-fluor-5-methoxy-[1,2,4]-triazolo-[1,5-c]- pyrimidin-2-sulfonamid (Florasulam), N-(2,6-Dichlor-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo[1,5-a]-pyrimidin-2-sulfonamid (Metosulam),
2-(4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1 H-imidazol-2-yl)-5- methoxymethyl-pyridin-3-carbonsäure (Imazamox),
N,N-Dimethyl-N'-(4-isopropyl-phenyl)-harnstoff (Isoproturon),
4-Amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-on (Metribuzin),
2-(2-Chlor-4-methylsulfonyl-benzoyl)-cyclohexan-1,3-dion (Sulcotrione),
Benzenecarbothiamid-,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluormethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluoro- (CAS 173980-17-1, HWH4991),
Methyl-5-(2,4-dichlor-phenoxy)-2-nitro-benzoat (Bifenox), und
(4-Amino-3,5-dichlor-6-fluor-pyridin-2-yl-oxy)-essigsäure (-2-butoxy-1- methyl-ethylester, -1-methyl-heptylester) (Fluroxypyr, -butoxypropyl, -meptyl),
sowie gegebenenfalls
and
such as
N- (4,6-Dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), N- (4-methoxy-6-methyl-1,3,5 - triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (metsulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2 - yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (tribenuronmethyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N' - (2- trifluoromethyl-phenylsulfonyl) urea (tritosulfuron),
N- (2,6-difluorophenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [1,5-c] pyrimidine-2-sulfonamide (florasulam), N- ( 2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam),
2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1 H -imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox),
N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon),
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin),
2- (2-chloro-4-methylsulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione),
Benzenecarbothiamid-, 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] - 5-fluoro- (CAS 173980-17-1, HWH4991),
Methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), and
(4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) -acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl)
and if necessary
2,6-Bis [4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoat (Natrium) (Bispyribacsodium)
enthalten. 9. Herbicidal composition according to one of claims 1 to 8, characterized in that it is an active ingredient in group 1
2,6-bis [4,6-dimethoxy-2-pyrimidinyl) oxy] benzoate (sodium) (bispyribacsodium)
contain.
Methyl-2-[[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl]amino]sulfonyl]-benzoesäure, Natrium-Salz (Propoxycarbazonesodium
enthalten. 10. Herbicidal agent according to one of claims 1 to 9, characterized in that it is an active ingredient of group 2
Methyl 2 - [[[(4,5-dihydihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino] sulfonyl] benzoic acid, sodium Salt (propoxycarbazone sodium
contain.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001129856 DE10129856A1 (en) | 2001-06-21 | 2001-06-21 | Selective herbicides based on pyrimidine derivatives |
| PCT/EP2002/006314 WO2003000058A1 (en) | 2001-06-21 | 2002-06-10 | Selective herbicides based on pyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001129856 DE10129856A1 (en) | 2001-06-21 | 2001-06-21 | Selective herbicides based on pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10129856A1 true DE10129856A1 (en) | 2003-01-02 |
Family
ID=7688906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2001129856 Withdrawn DE10129856A1 (en) | 2001-06-21 | 2001-06-21 | Selective herbicides based on pyrimidine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE10129856A1 (en) |
| WO (1) | WO2003000058A1 (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10334303A1 (en) * | 2003-07-28 | 2005-03-10 | Bayer Cropscience Gmbh | Herbicide combinations with special sulfonamides |
| CN100384840C (en) * | 2005-09-02 | 2008-04-30 | 中国科学院上海有机化学研究所 | 2-pyrimidinyloxybenzoic acid [2-(pyrimidineaminomethyl)]phenyl ester compound, preparation method and use thereof |
| ES2407657T3 (en) * | 2006-03-28 | 2013-06-13 | Riceco, Llc | Synergistic effects of ALS inhibitor herbicides when combined with propanil |
| WO2009089165A2 (en) * | 2008-01-07 | 2009-07-16 | Auburn University | Combinations of herbicides and safeners |
| CN102027971B (en) * | 2009-09-28 | 2013-09-18 | 南京华洲药业有限公司 | Herbicide composition containing diflufenzopyr, dicamba and nicosulfuron and application of herbicidal composition |
| US9723836B2 (en) * | 2009-11-19 | 2017-08-08 | Bayer Cropscience Ag | Synergistic pre-emergent and post-emergent weed control compositions and methods of use thereof |
| CN102461539B (en) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | A kind of mixed herbicide containing ethersulfuron, acetochlor and bispyribac and its application |
| CN102461547B (en) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | Hybrid herbicide containing Cinosulfuron, Bispyribac-sodium and cinmethylin and application of hybrid herbicide |
| CN102461508A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and butachlor |
| CN102461509A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and fluroxypyr and application thereof |
| CN102461505A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and quinclorac |
| CN102461511A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and cyhalofop-butyl |
| CN102461504A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and pretilachlor |
| CN102461519A (en) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | Mixed weeding composition containing bispyribac-sodium and oxadiargyl |
| CN103210932B (en) * | 2012-01-18 | 2015-02-11 | 山东滨农科技有限公司 | Herbicide composition containing pyribenzoxim and florasulam |
| CN104012544A (en) * | 2014-05-07 | 2014-09-03 | 广东中迅农科股份有限公司 | Weeding composition containing fenoxaprop-p-ethyl and bispyribac-sodium |
| CN104222095B (en) * | 2014-09-26 | 2016-06-15 | 青岛瀚生生物科技股份有限公司 | Herbicidal combinations containing dimethenamid and pyribenzoxim |
| CN105230644B (en) * | 2015-09-30 | 2017-10-03 | 河南科技学院 | A kind of Herbicidal combinations containing triflusulfuronmethyl and bromoxynil octanoate and its application |
| CN105851018A (en) * | 2016-05-27 | 2016-08-17 | 创新美兰(合肥)股份有限公司 | Oxaziclomefone and bispyribac-sodium compound suspending agent and preparation method thereof |
| CN106561663A (en) * | 2016-11-16 | 2017-04-19 | 江苏省农业科学院 | Pesticide composition containing picloram and bispyribac sodium, and application thereof |
| CN107683858A (en) * | 2017-09-19 | 2018-02-13 | 浙江天丰生物科学有限公司 | A kind of complex herbicidal composition |
| CN109645013A (en) * | 2019-02-21 | 2019-04-19 | 上海祥霖农业技术有限公司 | A kind of Herbicidal combinations and its application, herbicide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19947918A1 (en) * | 1999-10-06 | 2001-04-12 | Bayer Ag | Selective herbicides based on pyrimidine derivatives |
| HUP0301968A3 (en) * | 1999-11-17 | 2004-06-28 | Bayer Ag | Selective and synergistic herbicide compositions containing 2,6-disubstituted pyridine derivatives, preparation and use thereof |
| PL355974A1 (en) * | 1999-11-18 | 2004-05-31 | Bayer Aktiengesellschaft | Synergistic herbicidal active substance combinations |
| DE10031825A1 (en) * | 2000-06-30 | 2002-01-10 | Bayer Ag | Selective herbicides based on arylsulfonylaminocarbonyltriazolinones |
-
2001
- 2001-06-21 DE DE2001129856 patent/DE10129856A1/en not_active Withdrawn
-
2002
- 2002-06-10 WO PCT/EP2002/006314 patent/WO2003000058A1/en not_active Ceased
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| Publication number | Publication date |
|---|---|
| WO2003000058A1 (en) | 2003-01-03 |
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Owner name: BAYER CROPSCIENCE AG, 40789 MONHEIM, DE |
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