WO2003000058A1 - Herbicides selectifs a base de derives de pyrimidine - Google Patents
Herbicides selectifs a base de derives de pyrimidine Download PDFInfo
- Publication number
- WO2003000058A1 WO2003000058A1 PCT/EP2002/006314 EP0206314W WO03000058A1 WO 2003000058 A1 WO2003000058 A1 WO 2003000058A1 EP 0206314 W EP0206314 W EP 0206314W WO 03000058 A1 WO03000058 A1 WO 03000058A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- chloro
- ethyl
- phenyl
- urea
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 29
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 6
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 239000004480 active ingredient Substances 0.000 claims abstract description 53
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 34
- 244000038559 crop plants Species 0.000 claims abstract description 10
- -1 cyano, phenyl Chemical group 0.000 claims description 131
- 239000000203 mixture Substances 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 26
- 239000013543 active substance Substances 0.000 claims description 25
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 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 20
- 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
- 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 17
- 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 17
- 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 17
- 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 16
- 150000003839 salts Chemical class 0.000 claims description 16
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 15
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 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 15
- 239000005574 MCPA Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 14
- 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 14
- 239000005562 Glyphosate Substances 0.000 claims description 13
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 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
- 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 12
- 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 12
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 12
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 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 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 11
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000003666 Amidosulfuron Substances 0.000 claims description 9
- 239000005566 Imazamox Substances 0.000 claims description 9
- 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 9
- 239000005583 Metribuzin Substances 0.000 claims description 9
- 239000005618 Sulcotrione Substances 0.000 claims description 9
- 239000005629 Tritosulfuron Substances 0.000 claims description 9
- LVKBXDHACCFCTA-UHFFFAOYSA-N bencarbazone Chemical compound C1=C(C(N)=S)C(NS(=O)(=O)CC)=CC(N2C(N(C)C(=N2)C(F)(F)F)=O)=C1F LVKBXDHACCFCTA-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 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 9
- 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 9
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 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 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 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 9
- 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 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
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
- 239000005484 Bifenox Substances 0.000 claims description 8
- 239000005507 Diflufenican Substances 0.000 claims description 8
- 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 8
- 239000005529 Florasulam Substances 0.000 claims description 8
- 239000005582 Metosulam Substances 0.000 claims description 8
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 8
- 239000005596 Picolinafen Substances 0.000 claims description 8
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 8
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 8
- 229940097068 glyphosate Drugs 0.000 claims description 8
- 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 8
- 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 8
- 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 8
- 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 8
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 8
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 7
- 239000005558 Fluroxypyr Substances 0.000 claims description 7
- 229940100389 Sulfonylurea Drugs 0.000 claims description 7
- 235000013877 carbamide Nutrition 0.000 claims description 7
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000011734 sodium Chemical class 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- MJVXHAPMFSPZRH-UHFFFAOYSA-N 2-ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide Chemical compound C1=CC=CN2C(S(N)(=O)=O)=C(S(=O)(=O)CC)N=C21 MJVXHAPMFSPZRH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 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 6
- 239000005489 Bromoxynil Substances 0.000 claims description 6
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 6
- 239000005494 Chlorotoluron Substances 0.000 claims description 6
- 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 6
- 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 6
- 239000005531 Flufenacet Substances 0.000 claims description 6
- 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 6
- 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 6
- 239000005577 Mesosulfuron Substances 0.000 claims description 6
- 239000005619 Sulfosulfuron Substances 0.000 claims description 6
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound 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 6
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 6
- XVPAYLVQXRJFBG-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate;sodium Chemical compound [Na].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XVPAYLVQXRJFBG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 6
- JRORQDJBTMAFRO-UHFFFAOYSA-N 5-ethyl-2-(4-methyl-5-oxo-4-propyl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound N1C(=O)C(CCC)(C)N=C1C1=NC=C(CC)C=C1C(O)=O JRORQDJBTMAFRO-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 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 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 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 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- BFGQTWYXWNCTSX-UHFFFAOYSA-N triazine-4,5-dione Chemical class O=C1C=NN=NC1=O BFGQTWYXWNCTSX-UHFFFAOYSA-N 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- AXORVIZLPOGIRG-UHFFFAOYSA-N β-methylphenethylamine Chemical compound NCC(C)C1=CC=CC=C1 AXORVIZLPOGIRG-UHFFFAOYSA-N 0.000 claims description 5
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- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 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
- 108010050014 systemin Proteins 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Definitions
- the invention relates to new herbicidal, synergistic active ingredient combinations consisting of at least three mixing partners which consist of known pyrimidine derivatives on the one hand and known, herbicidally active compounds and, if appropriate, safeners on the other hand and can be used with particularly good success for selective weed control in different crops.
- Pyrimidine derivatives are the subject of a number of broad-spectrum herbicides
- Patent applications see US 4,906,285, EP-A-321 846, EP-A 658 549, US 4 248 619, US 4427 437.
- the known pyrimidine derivatives have a number of activity gaps.
- the compatibility of these compounds with crop plants is also not entirely satisfactory under all conditions.
- the phenoxypyrimidine derivatives together with other, preferably two further, known herbicidally active compounds when used together, if appropriate with the compounds (safeners / antidots) which improve crop tolerance and are described below, are particularly advantageous as broadly active combination preparations for selective use Control of weeds in crops such as cereals, such as wheat, barley, rye and rice, but can also be used in maize.
- the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising
- R is hydrogen, -CH 2 CH 2 S (O) n R 1 (where Rj is C r C 4 alkyl and n is 0.1 or 2) or
- R 2 for hydrogen, halogen, cyano, phenyl, C j -Cs-alkyl, C1-C4- alkoxy, C ⁇ -C4-alkylthio, C ⁇ -C -alkoxycarbonyl, mono- or di-C i -C4- alkylaminocarbonyl, phenyl- C j -C4-Alkylaminocarb- onyl, where the phenyl group may optionally be substituted by halogen, -CC C2-alkyl or C C2-alkoxy, furylmethylaminocarb- onyl or phenyl, and
- R3 represents in each case optionally substituted by halogen, cyano, nitro, C j - C4 substituted alkyl, C C4-alkoxy or allyloxy phenyl, optionally substituted by C ⁇ - alky !, phenoxy, benzyloxy or acetoxy-substituted amino, for -C-C4-alkylthio or for the grouping -COR 4 , where R 4 is C j - C4-alkyl, benzyloxy or benzylamino,
- A represents chlorine or methoxy
- D and E which may be the same or different, represent hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxy substituted by halogen,
- N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron-methyl), 1 - chloro-N- [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-l, 3-dioxo-lH-pyrrolo [l, 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 - [[(l-methylethylidene) amino] oxy] ethyl] -2-
- phenylcarbothiamide- 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -1H-1, 2,4-triazole - 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).
- R preferably represents hydrogen or
- R 2 preferably represents hydrogen, chlorine, cyano, phenyl, C Cg-alkyl, methoxy,
- R 3 preferably represents phenyl optionally substituted by chlorine, fluorine, cyano, nitro, methyl, methoxy, ethoxy, butoxy, allyloxy, methylthio, dimethylamino, phenoxy, benzyloxy or acetoxy or -COR4, in which
- R4 represents methoxy, ethoxy, methyl, benzyloxy or benzylamino
- A preferably represents chlorine or methoxy
- R 2 particularly preferably represents hydrogen, methyl, methylthio, cyano, methoxycarbonyl or phenyl.
- R3 particularly preferably represents phenyl optionally substituted by methyl or methoxy.
- D and E are particularly preferably methoxy.
- R 2 very particularly preferably represents phenyl.
- R 3 very particularly preferably represents phenyl.
- 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:
- 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-l, 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),
- Herbicides from the class of the sulfonylureas, triazolopyrimidines, are used in particular as mixture components from the active ingredients of group 3.
- Imidazolinones ureas, triazinediones, triketones, triazolinones, benzonitriles, Phenoxypropionic acid derivatives, dichlo ⁇ henoxyacid derivatives, carboxamides, oxyacetamides and other herbicidal active ingredients, which are listed in detail below:
- bromoxynil 3,5-dibromo-4-hydroxy-benzonitrile
- ioxynil 4-hydroxy-3,5-diiodobenzonitrile
- N-phosphonomethyl-glycine (-isopropylammmonium salt), (glyphosate, -isopropylammonium),
- N-phosphonomethyl-glycine trimethyl sulfonium (sulfosate).
- the active substance combinations defined above from the phenoxypyrimidine derivatives of the formula (I) and the active substance from group 2 in combination with active substances from group 3, if appropriate in combinations with active substances from group 4, with very good crop plant tolerance have particularly high herbicidal activity and in various crops such as. B. in soy, potatoes, corn or rice and especially in Cereals such as barley, rye, triticale and especially wheat can be used for selective weed control.
- the herbicidal activity of the active substance combinations according to the invention composed of compounds from groups 1, 2 and 3 listed above is considerably higher than the sum of the effects of the individual active substances.
- the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
- the new active ingredient combinations thus represent a valuable addition to the selective herbicides.
- active substances of group 4 in combination with one or more of the one or more Listed active ingredients of group 2 and group 3 with very good crop tolerance, have a particularly high herbicidal activity and can be used in various crops, in particular in cereals, especially wheat, but also in soybeans, potatoes, corn and rice for selective weed control.
- a preferred embodiment is therefore also a mixture comprising a compound of the 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 active ingredients or of the group mentioned above 2 and 3.
- Typical derivatives of 2,4-D are their esters.
- a preferred embodiment is also a mixture comprising a compound of formula (I) and / or its 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 more compounds of group 3.
- Safeners or antidots which are capable of antagonizing the damaging effect of a herbicide on the cultivated plants, are particularly suitable for the group 4 compounds listed above, the damaging effect of compounds of the formula (I) and their salts in combination with one or more of the or the above-mentioned active ingredients of groups 2 and 3, to almost completely cancel the cultivated plants without impairing the herbicidal activity against the weeds.
- the active substance combinations according to the invention can e.g. can be used in the following plants:
- Brassica, lactuca, cucumis, cuburbita Brassica, lactuca, cucumis, cuburbita.
- plants and parts of plants can be treated.
- Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
- Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
- Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being used
- Roots are listed.
- the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
- the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
- plants and their parts can be treated according to the invention.
- transgenes are also preferred.
- Plants and plant varieties that have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts treated.
- the term “parts” or “parts of plants” or “plant parts” was explained above.
- Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
- Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
- the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”).
- Such properties are better plant growth, increased Tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products , Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
- the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton,
- Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton and rapeseed are particularly emphasized.
- the properties (“traits”) that are particularly emphasized are the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CrylA), Cry ⁇ A ( c), CryllA, CrylHA, CryIIIB2, Cry9c, Cry2Ab, CrySBb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
- the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),
- Plant plants are maize varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
- YIELD GARD® e.g. corn, cotton, soy
- KnockOut® e.g. corn
- StarLink® e.g. corn
- Bollgard® Cotton
- Nucoton® cotton
- NewLeaf® potato
- herbicide Tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rape), IMI® (tolerance to imidazolinones) and ST
- Plants (conventionally bred to herbicide tolerance) should also be mentioned the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
- Clearfield® e.g. maize
- the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
- the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. Generally 1 part by weight
- Active ingredient of the formula (I) in each case 0.001 to 1000 parts by weight, preferably 0.005 to 200 parts by weight in each case and particularly preferably in each case 0.01 to 100 parts by weight of active ingredient of groups 2 and 3.
- 1 to 1 part by weight of group 1 each contains 0.1 to 1 part by weight of active substances in groups 2 and 3.
- the advantageous effect of the compatibility of cultivated plants of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
- the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 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 1 to 1 part by weight of active compound of the formula (I), its salts or mixtures thereof with active compounds of groups 2 and 3 Above under (d), the crop plants tolerability-improving compounds (antidots / safeners).
- 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 substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
- formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents
- organic solvents can also be used as auxiliary solvents.
- auxiliary solvents e.g. organic solvents
- aromatics such as xylene, toluene, or alkylnaphthalenes
- chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
- 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, and water.
- 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, and water.
- Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. 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 stalks;
- suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
- Possible dispersing agents are, for example,
- Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments, e.g. 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.
- the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, including the safing active ingredients, preferably between 0.5 and 90%.
- the active compound combinations according to the invention are generally used in the form of finished formulations.
- the active substances contained in the active substance combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
- the new combinations of active ingredients can also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible. Also a mixture with other known active ingredients, such as fungicides, insecticides, Acaricides, nematicides, bird repellants, growth agents, plant nutrients and soil structure improvers are possible. For certain applications, particularly in the post-emergence process, it may also be advantageous to include plant-compatible mineral or vegetable oils or ammonium salts such as ammonium sulfate or ammonium rhodanide in the formulations as further additives.
- the new active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
- the active compound combinations according to the invention can be applied before and after emergence of the plants, ie in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
- Herbicides always have a synergistic effect if the herbicidal activity of the active ingredient combination is greater than that of the individual active ingredients applied.
- the effect of the combination is super-additive, that is, it shows a synergistic effect.
- the required amounts of the formulations were mixed with one another and optionally other substances were added, and then diluted with water to the desired concentration.
- the amount of formulation in the solutions to be tested corresponds to the desired application rates per hectare. preemergence
- Seeds of the test plants are sown in normal soil. After 24 hours, the desired amount of active substance is sprayed onto the soil surface as a formulation.
- the concentration of the active substances in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
- Test plants are grown under controlled temperature and light conditions. Spraying with the test solution takes place when the plants have reached a height of 5 to 15 cm.
- the concentration of the active substance in the spray solution is chosen so that the desired application rate can be applied in 500 l of water / ha.
- the evaluation takes place about three weeks after the application.
- the herbicidal activity is assessed visually in comparison to the untreated control. Mean it
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Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2001129856 DE10129856A1 (de) | 2001-06-21 | 2001-06-21 | Selektive Herbizide auf Basis von Pyrimidin-Derivaten |
DE10129856.0 | 2001-06-21 |
Publications (1)
Publication Number | Publication Date |
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WO2003000058A1 true WO2003000058A1 (fr) | 2003-01-03 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP2002/006314 WO2003000058A1 (fr) | 2001-06-21 | 2002-06-10 | Herbicides selectifs a base de derives de pyrimidine |
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DE (1) | DE10129856A1 (fr) |
WO (1) | WO2003000058A1 (fr) |
Cited By (22)
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WO2005011381A1 (fr) * | 2003-07-28 | 2005-02-10 | Bayer Cropscience Gmbh | Combinaisons herbicides comprenant des sulfonamides particuliers |
CN100384840C (zh) * | 2005-09-02 | 2008-04-30 | 中国科学院上海有机化学研究所 | 2-嘧啶氧基苯甲酸[2-(嘧啶氨基甲基)]苯酯类化合物、制备方法及其用途 |
EP1998613A2 (fr) * | 2006-03-28 | 2008-12-10 | Riceco, LLC | Effets synergiques des herbicides inhibiteurs als combinés avec du propanil |
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Cited By (29)
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WO2005011381A1 (fr) * | 2003-07-28 | 2005-02-10 | Bayer Cropscience Gmbh | Combinaisons herbicides comprenant des sulfonamides particuliers |
EA009765B1 (ru) * | 2003-07-28 | 2008-04-28 | Байер Кропсайенс Гмбх | Тройные гербицидные комбинации, включающие сульфонамиды |
CN100384840C (zh) * | 2005-09-02 | 2008-04-30 | 中国科学院上海有机化学研究所 | 2-嘧啶氧基苯甲酸[2-(嘧啶氨基甲基)]苯酯类化合物、制备方法及其用途 |
EP1998613A2 (fr) * | 2006-03-28 | 2008-12-10 | Riceco, LLC | Effets synergiques des herbicides inhibiteurs als combinés avec du propanil |
EP1998613A4 (fr) * | 2006-03-28 | 2010-06-23 | Riceco Llc | Effets synergiques des herbicides inhibiteurs als combinés avec du propanil |
WO2009089165A2 (fr) * | 2008-01-07 | 2009-07-16 | Auburn University | Combinaisons d'herbicides et de phytoprotecteurs |
WO2009089165A3 (fr) * | 2008-01-07 | 2010-08-26 | Auburn University | Combinaisons d'herbicides et de phytoprotecteurs |
CN102027971A (zh) * | 2009-09-28 | 2011-04-27 | 南京华洲药业有限公司 | 含氟吡草腙、麦草畏及烟嘧磺隆的除草剂组合物及其应用 |
JP2013511523A (ja) * | 2009-11-19 | 2013-04-04 | バイエル クロップサイエンス エルピー | 相乗的発芽前および発芽後雑草防除組成物およびその使用方法 |
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