MXPA98001955A - Herbicides mixes with sinerget action - Google Patents
Herbicides mixes with sinerget actionInfo
- Publication number
- MXPA98001955A MXPA98001955A MXPA/A/1998/001955A MX9801955A MXPA98001955A MX PA98001955 A MXPA98001955 A MX PA98001955A MX 9801955 A MX9801955 A MX 9801955A MX PA98001955 A MXPA98001955 A MX PA98001955A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- alkoxy
- alkyl
- halogen
- carry
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract description 12
- -1 methoxy, ethoxy Chemical group 0.000 claims abstract description 94
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 229940100389 Sulfonylurea Drugs 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 230000002195 synergetic effect Effects 0.000 claims abstract description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims abstract description 5
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 claims abstract description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 210000001268 chyle Anatomy 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 239000000047 product Substances 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 13
- MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 description 11
- 239000005562 Glyphosate Substances 0.000 description 10
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 10
- 239000005476 Bentazone Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- 239000005507 Diflufenican Substances 0.000 description 8
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 8
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000003666 Amidosulfuron Substances 0.000 description 7
- 239000005472 Bensulfuron methyl Substances 0.000 description 7
- 239000005504 Dicamba Substances 0.000 description 7
- 239000005574 MCPA Substances 0.000 description 7
- 239000005584 Metsulfuron-methyl Substances 0.000 description 7
- 239000005616 Rimsulfuron Substances 0.000 description 7
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 7
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 7
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 7
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000005501 Cycloxydim Substances 0.000 description 6
- 239000005586 Nicosulfuron Substances 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 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 description 6
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 6
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 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 description 5
- ONNQFZOZHDEENE-UHFFFAOYSA-N 2-[5-(but-3-yn-2-yloxy)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione Chemical compound C1=C(Cl)C(OC(C)C#C)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F ONNQFZOZHDEENE-UHFFFAOYSA-N 0.000 description 5
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 5
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 5
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 5
- 239000005484 Bifenox Substances 0.000 description 5
- 239000005489 Bromoxynil Substances 0.000 description 5
- 239000005498 Clodinafop Substances 0.000 description 5
- 239000005499 Clomazone Substances 0.000 description 5
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 5
- 239000005514 Flazasulfuron Substances 0.000 description 5
- 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 description 5
- 239000005564 Halosulfuron methyl Substances 0.000 description 5
- 239000005570 Isoxaben Substances 0.000 description 5
- 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 description 5
- 239000005582 Metosulam Substances 0.000 description 5
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 5
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 5
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 5
- 239000005606 Pyridate Substances 0.000 description 5
- 239000005608 Quinmerac Substances 0.000 description 5
- 239000005618 Sulcotrione Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 5
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 5
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 5
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 5
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 5
- XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 5
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 5
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 5
- 229940097068 glyphosate Drugs 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 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 description 5
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 5
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 5
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 5
- 229960002939 metizoline Drugs 0.000 description 5
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 5
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 5
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 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 description 5
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group 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 description 4
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 4
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 4
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005469 Azimsulfuron Substances 0.000 description 4
- 239000005497 Clethodim Substances 0.000 description 4
- 239000005500 Clopyralid Substances 0.000 description 4
- DQZCVNGCTZLGAQ-UHFFFAOYSA-N Cycluron Chemical compound CN(C)C(=O)NC1CCCCCCC1 DQZCVNGCTZLGAQ-UHFFFAOYSA-N 0.000 description 4
- 239000005502 Cyhalofop-butyl Substances 0.000 description 4
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 4
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 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 description 4
- 239000005576 Mecoprop-P Substances 0.000 description 4
- 239000005580 Metazachlor Substances 0.000 description 4
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 4
- 239000005594 Phenmedipham Substances 0.000 description 4
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 4
- 239000005604 Prosulfuron Substances 0.000 description 4
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 4
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 4
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 4
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 4
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 4
- 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 description 4
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 4
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 description 4
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- 239000003979 granulating agent Substances 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 210000004124 hock Anatomy 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- IDFXUDGCYIGBDC-UHFFFAOYSA-N n-[4-ethylsulfanyl-2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound CCSC1=CC=C(NS(C)(=O)=O)C(C(F)(F)F)=C1 IDFXUDGCYIGBDC-UHFFFAOYSA-N 0.000 description 1
- KDOKZLSGPVBDLS-UHFFFAOYSA-N n-[5-(1-chloro-2-methylpropan-2-yl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide Chemical compound S1C(C(C)(CCl)C)=NN=C1NC(=O)C1CC1 KDOKZLSGPVBDLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005486 naphthalic acid group Chemical group 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-O propan-1-aminium Chemical compound CCC[NH3+] WGYKZJWCGVVSQN-UHFFFAOYSA-O 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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Abstract
The present invention relates to: Herbicidal mixture containing a) at least one derivative of the sulfonylurea of the formula I: wherein the substituents have the following meanings: R1 C1-C6-alkyl, which may carry one to five of the following groups: methoxy, ethoxy, SO2CH3, cyano, chloro, fluoro, SCH3, S (O) CH3, halogen, an ER6 group, where E means O, S, or NR7, COOR8, NO2, S (O) pR9, SO2NR10R11, CONR10R11; R2 hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, halogen, C1-C4-alkoxy, C1-C4-halogenoalkoxy, C1-C4-halogenoalkyl, a C1-C2-alkylsulfonyl group nitro, cyano or C1-C4-alkylthio, R3 F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or when R1 means CO2CH3 and R2 means at the same time fluoro, Cl, or when R1 signifies CH2CF3 or CF2CF3, methyl, or , when R4 means OCF3 or OCF2Cl, OCF2H0OCF2Br, R4 C1-C2-alkoxy, C1-C2-alkyl, C1-C2-alkylthio, C1-C2-alkylamino, di-C1-C2-alkylamino, halogen, C1-C2- haloalkyl, C1-C2-haloalkoxy, R5 hydrogen, C1-C2-a lcoxy, C1-C4-alkyl, R6 C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which may contain from 1 to 5 halo atoms, with the exception of allyl, difluoromethoxy, chlorodifluoromethoxy and 2-chloroethoxy, when E means O or S. In addition, R denotes, when E is O or NR, additionally methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, allylsulfonyl, propargylsulfonyl or dimethylsulphamoyl; R7 hydrogen, methyl or ethyl R8 a group C1- C6-alkyl which can carry up to three of the following radicals: halogen, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-halogenoalkoxy, C1-C4-alkoxy-C1-C2-alkoxy, C3-C7-cycloalkyl and / or phenyl, a C5-C7-cycloalkyl group which can carry up to three C1-C4-alkyl groups, C3-C6-alkenyl or C3-C6-alkynyl group, R9 a C1-C6-alkyl group which can carry from one to three of the following halogen radicals, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy, C1-C4-C1-C2-alkoxy-alkoxy, C3-C7-cycloalkyl and / or phenyl; a C5 group -C7-cycloalkyl that p can carry one to three C1-C4-alkyl groups, a C2-C6-alkenyl group or a C3-C6-alkynyl group, R10 hydrogen, a C1-C2-alkoxy group, a C1-C6-alkyl group or R10 form together with R11 a C4-C6-alkylene chain where a methylene group can be substituted by an oxygen atom or a C1-C4-alkylimino group; R11 a C1-C4-alkyl group which can carry from one to four C1-C4 halogen radicals -alkoxy, C3-C6-cycloalkylon 0-3 or 1-2 N, CH or its ecologically tolerated salts, and b) an active synergistic amount of at least one herbicidal compound of groups B1 to b41 indicated in claim 1, herbicides, as well as a procedure to combat the growth of unwanted plants
Description
Herbicide mixtures with synergetic action
Description
The present invention relates to herbicidal mixtures with synergistic action from a derivative of the sulfonylurea (a) of the formula I and one or more herbicidal compounds bl a b41.
The sulfonylureas of the formula i with herbicidal action are known from the state of the art, for example, from patents EP-388 873, EP-559 814, EP-291 851 and DE-40 07 683 and from Confe-rence Proccedings " Fluorine in Agriculture ", January 9-11, 1995, Manchester, Cap. "New Fluoro Intermediates for Herbici-dal Sulfonylureas".
The herbicidal compounds bl to b41 are described, for example, in '? Erbizide ", Hock, Fedtke, Schmidt, edition, Thieme 1995 (see" Quinclorac "page 238," Molinat "page 32," Butachlor "p. 32, "Pretilachlor" page 32, "Dithiopyr" page 32, "Mefenacet" page 32, "Fenoxapropethyl" page 216, "Dimepi-perate" page 32, "Pyrazolate" page 146, "Pyrazoxyfen" page 146, "Bensulfuronmethyl page 31," Pyrazosulfuron-Ethyl "page 31," Cinosulfuron "page 31," Benfuresate "page 233," Bromobu-tide "page 243," Dymron "page 243," Dimethyametryn page 118, "Esprocarb" page 229, "Pyributicarb" page 32, "Cinemthylin" page 32, "Propanil" page 32, "2, 4-D" page 30, "Bentazon" page 30, "DPX-A-8947" page 175, "Mecoprop-P" page 237, "Chlorpro-pham" page 205, "Thiocarbazil" page 229, "Ethoxyfen" page 30, "Haloxyfop-P-Methyl" page 38, "Haloxyfop-Ethoxyethyl" page 38, "Flumiclorac-Pentyl" page 35, "Flupropacil" page 143, "Nipy-raclofen" page 145, "Metosulam" page 33, "Ethametsul furon-Methyl "page 36," Thifensulfuron-Methyl ". p. 35 or in "Agricultural Chemicals", Book II Herbicides, 1993 see "Thi-obencarb" p. 85, "Benzofenap" p. 221, "Napropanilid" p. 49, "Piperophos" p. 102, "Anilofos" p. 241, "TH-913" p. 150, "H -52" p. 54, "ICIA-0051" p. 268, "Poast" p. 253, "Focus" p. 222, "Dimethenamid" p. 48, "Sulfosate" p. 236, "2,4-DB" p. 10, "Dichlorprop-P" p. 6, "Flupoxam" p. 44, "Prosulfocarb" p. 84, "Quinmerac" p. 233, "Metazach-lor" p. 64, "Flurtamone" p. 265, "Bromofenoxim" p. 228, "Fomesafen" p. 248, "Imazethabenz-Methyl" p. 153, "Clodi-nafop" p. 214, "Fenoxaprop-P-Ethyl" p. 208, "Fluazifop-P-Butyl" p. 207, "Quizalofop-P-Ethyl" p. 210, "Quizalofop-Terfuryl" p. 211, "Flumioxazin" p. 43, "Flumipropyn" p. 267, "Sulfentrazone" p. 261, "Thiazopyr" p. 226, "Pyri-thiobac-Sodium" p. 266, "Flumetsulam" p. 227, "Amido-sulfuron" p. 151, "Halosulfuron-Methyl" p. 148, "Rimsulfu-ron" p. 138, "Tribenuron-Methyl" p. 139, "Triflusulfuron-Methyl" p. 137, "Primisulfuron" p. 147 or in "Short Review of Herbicides &PGRs 1991, Hodogaya Chemicals see" Furyloxyfen "page 142," Triazophenamid "page 268," KH-218"page 52," NSK-850"page 52," JC -940"page 0," AC-92553"page 58," Buthidazole "page 88," Cyprazole "page 38," Allidochlor "page 48," Benzoylprop-ethyl "page 38," Chlorthiamid "page 150, "Diphenamid" page 34, "Flamprop-methyl" page 40, "Fosamin" page 232, "Isoxaben" page 42, "Mo-nalide" page 32, "Naptalam" page 36, " Pronamid "page 34," Bia-laphos "page 234," Glufosinate-ammonium "page 234," Glypho-sate "page 232," Amitrol "p.254," Clomeprop p. 20, "Dichlorprop" p. 6, "Fenoprop" p. 8, "Fluroxypyr" p.156, "MCPA" p. 4, "MCPB" p. 8, "Mecoprop" p. 6, "Napropamide" p. 16, "Triclopyr" p. 154, "Chloramben" p. 28, "Dicamba" p. 26, "Clomazone" p. 268, "Diflufenican" p. 42, "Fluorochloridone" p. 266, "Fluridone," p. 156, "Asulam" p. 112, "Barban" p. 100, "Butylate" p. 106, "Carbeta-mide" p. 36, "Chlorobufam" p. 100, "Cycloate" p. 108,
"Desmedipham" p. 104, "Diallate" p. 106, "EPTC" p. 108, "Orbencarb" p. 112, "Pebulate" p. 106, "Phenisopham" p. 118, "Pendimedipham" p. 104, "Propham" p. 100, "Sulfalíate" p. 110, "Terbucarb" p. 102, "Triallate" p. 108, "Vernolate" p. 108, "Acetochlor" p. 48, "Alachlor" p.
46, "Diethathyl-ethyl" p. 48, "Dimethachlor" p. 50, "Meto-lachlor" p. 46, "Propachlor" p. 44, "Pyrnachlor" p. 44, "Terbuchlor" p. 48, "Xylachlor" p. 52, "Alloxydim" p. 260, "Clethodim" p. 270, "Cloproxydim" p. 268, "Tralkoxy-dim" p. 270, "Dalapon" p. 212, "Ethofumesate" p. 124, "Benefin" p. 54, "Butralin" p. 58, "Dinitramin" p. 56, "Ethalfluralin" p. 60, "Fluchloralin" p. 54, "Isopropalin" p. 58, "Nitralin" p. 58, "Oryzalin" p. 60, "Prodiamine" p. 62, "Profluralin" p. 54, "Trifluralin" p. 54, "Dino- p. 128, "DinoAcet t" p. 128, "Dinoterb" p. 128, "DNOC" p. 126, "Acylfluorfen-Sodium" p. 142, "Aclonifen" p. 146, "Bifenox" p. 140, "Chlornitrofen" p. 138, "Dife-noxuron" p. 76, "Fluorodifen" p. 138, "Fluoroglycofen-Ethyl" p. 146, "Lactofen" p. 144, "Nitrofen" p. 136, "Nitrofluorfen" p. 140, "Oxyfluorfen" p. 140, "Cypercjuat" p. 158, "Difenzoquat" p. 160, "Diquat" p. 158, "Para-cjuat" p. 158, "Benzthiazuron" p. 82, "Buturon" p. 66, "Chlorbromuron" p. 72, "Chloroxuron" p. 76, "Chlortoluron" p. 74, "Cycluron" p. 84, "Dimeturon" p. 88, "Diuron" p. 70, "Ethidimuron" p. 86, "Fenuron" p. 64, "Fluometu-ron" p. 68, "Isoproturon" p. 80, "Isouron" p. 88, "Kar-butilat" p. 76, "Linuron" p. 72, "Methabenzthiazuron" p.
82, "Metoxuron" p. 72, "Monolinuron" p. 66, "Monuron" p. 64, "Neburon" p. 72, "Siduron" p. 68, "Tebuthiuron" p. 86, "Trimeturon" p. 64, "Isocarbamid" p. 168, "Imazametha-pyr" p. 172, "Imazapyr" p. 170, "Imazacrjuin" p. 170, "Imazethapyr" p. 172, "Methazole" p. 162, "Oxadiazon" p. 162, "Tridiphane" p. 266, "Bromoxynil" p. 148, "loxynil" p. 148, "Diclofop-Methyl" p. 16, "Fenthiaprop-Ethyl" p. 20, "Fluazifop-Butyl" p. 18, "Haloxyfop-Methyl" p. 18, "Isoxapyrifop" p. 22, "Propa" quizafop "p. 24, "Quizalofop-Ethyl" p. 20, "Chlorfenac" p. 258, "Chlorophenprop-Methyl" p. 258, "Chloridazon" p. 174, "Maleic Hydrazide" p. 162, "Norflurazon" p. 174, "Pyridate" p. 176, "Clopyralid" p. 154, "Piclora" p. 154, "Chlorimuron-Ethyl" p. 92, "Chlor-sulfuron" p. 92, "Flazasulfuron" p. 96, "Metsulfuron-Methyl" p.92, "Nicosulfuron" p. 96, "Sulfometuron-Methyl" p. 92, "Triasulfuron" p. 94, "Ametryn" p. 198, "Atrazin" p. 188, "Aziprotryne" p. 206, "Cyanazine" p. 192, "Cy-prazine" p. 192, "Desmetryne" p. 200, "Dipropetryn" p. 202, "Eglinazin-Ethyl" p. 208, "Hexazinon" p. 208, "Pro-cyazine" p. 192, "Prometone" p. 196, "Prometryn" p. 196, "Propazin" p. 188, "Secbumeton" p. 196, "Simazine" p. 188, "Simetryn" p. 196, "Terbumeton" p. 204, "Terbutryn" p. 198, "Terbutylazin" p. 190, "Trietazine" p. 188, "Ethiozin" p. 210, "Metamitron" p. 206, "Metribuzin" p. 202, "Bromacil" p. 180, "Lenacil" p. 180, "Terbacil" p. 180, "Benazolin" p. 262, "Bensulide" p. 228, "Benzofluor" p. 266, "Butamifos" p. 228, "DCPA" p. 28, "Dichlobenil" p. 148, "Endothal" p. 264, "Mefluidide" p. 306, "Per-fluidone" p. 260, "Terbuchlor" p. 48 or in "Global Herbicide Directory" First Edition, 1994 see "Oxa-diargyl" p. 96, or in "European Directory of Agrochemical Products" Volume 2 - Herbicides "Fourth Edition, see" Bumi-nafos "on page 255. The compound" DEH-112"is known from the application for registration of European patent EP 0 302 203 The compound "Caloxydim" is known from DE 3 336 140, the compound "Cinidon-Ethyl" is described in 3,603,789 and the compendium "Fluorbentranil" in EP 84 893. Other compounds are known from "Brighton" crop Protection conference - eeds - 1993 (see "Thidiazimin" page 29, "AC-322140" page 41, "KIH-6127" page 47, "Prosulfuron" page 53, "KIH-2023" page 61, "Metoben-zuron" page 67). The compound "CH-900" is described in EP 0 332 133.
In phytosanitary products, it is, in principle, desirable to increase the specific action of an active substance and increase the safety of action. Therefore, the purpose of the invention was to increase the action of the known sulfonylureas of herbicidal action corresponding to formula I.
It has been found, now a herbicidal mixture containing
a) at least one derivative of the sulfonylurea of the formula I
wherein the substituents have the following meanings:
R1 Ci-Cβ-alkyl, which may carry one to five of the following groups: methoxy, ethoxy, S02CH3, cyano, chloro, fluoro, SCH3, S (0) CH3;
halogen;
a group ER6, where E means 0, S or NR7;
COOR8;
N02;
S (0) or R9, S02NR10R1: L, CONR10R1: L;
R 2 hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -al "quenyl, C 2 -C 4 -alkynyl, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy; C? -C4-halogenoalkyl, a C? -C2-alkylsulphonyl, nitro, cyano or C? -C4-alkylthio group,
R3 F, CF3, CF2C1, CF2H, 0CF3, 0CF2C1 or, when R1 means
C02CH3 and R2 means at the same time fluoro, Cl, or, when R1 signifies CH2CF3 or CF2CF, methyl, or, when R4 signifies OCF3 or 0CF2C1, 0CF2H or 0CF2Br;
R4 C? -C2-alkoxy, C? -C2-al "chyle, C? -C2-alkylthio, C? -C2-alkylamino, di-C? -C2-alkylamino, halogen, C? -C2-haloalkyl , C1-C2-haloalkoxy,
R5 hydrogen, C? -C2-alkoxy, C? -C4-alkyl;
R6 C? -C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or
C3-C6-cycloalkyl, which can carry from 1 to 5 halogen atoms, with the exception of allyl, difluoromethoxy, chlorodifluoromethoxy and 2-chloroethoxy, when E means O or S. In addition, it means R6, when E is 0 or NR, additionally methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, allylsulfonyl, propargyl sulphonyl or dimethylsulphamoyl; R7 hydrogen, methyl or ethyl
R8 a Ci-Cß-alkyl group which can carry up to three of the following radicals: halogen, C?-C4-alkoxy, C?-C4-alkylthio, C?-C4-haloalkoxy, C?-C4-alkoxy-C? -C2-alkoxy, C3-C-cycloalkyl and / or phenyl; a C5-C-cycloalkyl group which can carry up to three C? -C4 alkyl groups; C3-C6-alkenyl or C3-C6-l "quinilo;
R9 a C? -C6-alkyl group which can carry from one to three of the following radicals: halogen, C? -C4-alkoxy,
C? -C4-alkylthio, C? -C4-haloalkoxy, C? -C4-alkoxy-C? -C2-alkoxy, C3-C-cycloalkyl and / or phenyl; a C5-C-cycloalkyl group that can carry one to three C? -C4-alkyl groups; a C2-C6-al group "quenyl or a C3-C6-alkynyl group;
Ri ° hydrogen, a C? -C2-alkoxy group, a C! -C6-alkyl group or R10 together with R11 forms a C4-C6 ~ alkylene chain where a methylene group can be substituted by a oxygen atom or a C? -C4 ~ alky1imino group;
Rii a C? -C4-alkyl group which can carry from one to four halogen or C? -C4-alkoxy radicals; C3-C6-cycloalkyl
n 0 - 3
or 1 - 2
z N, CH
an active synergistic amount of at least one herbicidal compound of groups bl to b41
bl 1, 3,4-thiadiazoles: butidazoles, ciprazoles
b2 alidochloride amides (CDAA), benzoylprop-ethyl, bromobutides, chlorothiamide, dimepiperates, dimethenamid, diphenamide, ethobenzanide (benzchlomet), flamprop-methyl, fosamine, isoxaben, monalide, naptalame, proamylidene, propanil
b3 aminophosphoric acid: bilanafos,. { bialaphos), buminaphos, glufosinate-ammonium, glyphosate, sulfosate
b4 aminotriazoles: amitrol b5 anuidas: anilofos, mefenacet
b6 aryloxyalkanoic acids: 2, 4-D, 2,4-DB, clomeprop, dichloroprop, dichloroprop-P, dichloroprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoro- Rooxipyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr
b7 benzoic acids: cloroamben, dicamba
b8 benzothiadiazinones: bentazone
b9 bleacher: clomazone (dimetazone), diflufenican, fluorochloroid, flupoxam, fluridone, pyrazolate, sulcotrione (chloromesulone)
carbamates: asulam, barban, butilate, carbetamid, chlorobufam, chloropropham, cycloate, desmedipham, diallate, EPTC, esprocarb, molinate, orbencarb, pebulate, phenisopham, phenmedipham, propham, prosulfocarb, pyributicarb, sulfallate (CDEC), terbucarb, thioben- carb (benthiccarb), thiocarbazyl, triallate, vernolate
bll quinolinecarboxylic acids: quinclorac, quinmerac bl2 chloroacetanilides: acetochlor, alachlor, butachlor, butenachlor, diethyl ethyl, dimethachlor, metazachlor, metolachlor, pretilachlor, propachlor, prynachlor, terbuclor, thenilchlor, xylachlor
bl3 cyclohexenones: alloxidim, caloxidim, clethodim, cloproxydim, cycloxidim, sethoxydim, tralcoxydim, 2-. { 1- [2- (4-chlorophenoxy) propyloxyimino] butyl} - 3-hydroxy-5- (2H-tetrahydropothiopyran-3-yl) -2-cyclohexen-1-one
bl4 dichloropropionic acids: dalapon
bl5 dihydrobenzofurans: etofumesate
bl6 dihydrofuran-3-ones: flurtamone
bl7 dinitroanilines: benefina, butralina, dinitramina, etalfluralina, flucloroalina, isopropalina, nitralina, oryzalina, penidimetalina, prodiaminas, profluralina, trifluralina
bl8 dinitrophenols: bromophenoxy, dinoseb, dinoseb-acetat, dinoterb, DNOC
bl9 diphenylethers: acifluorophen-sodium, aclonifen, bifenox, chloronitrofen (CNP), diphenoxuron, ethoxifen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furiloxifen, lactofen, nitrofen, nitrofluorofen, oxyfluorofen
b20 dipyridylenes: cyperquat, diphenoquat-methylsulfate, diquat, paraquat hydrochloride
b21 ureas: benzthiazurone, buturone, chlorobromuron, chlorooxuron, chlorotoluron, cumiluron, dibenziluron, cycluron, dimefuron, diuron, dymrona, etidimuron, fenuron, fluorometuron, isoproturon, isourone, karbutylate, lyuron, metabenzthiazuronase, metobenzuron, methoxuron , monolinurone, monurone, neburone, sidurone, tebutiurone, trimeturon
b22 imidazoles: isocarbamide
b23 imidazolinones: imazametapyr, imazapyr, imazaquin, imazetabenz-methyl (imazame), imazetapyr
b24 oxadiazoles: metazoles, oxadiargyl, oxadiazone
b25 oxiranes: tridiphane b26 phenols: bromoxynil, ioxinil
b27 phenoxyphenoxypropionates: clodinafop, cyhalofop-butyl, diclofop-methyl, phenoxapropyl, fenoxaprop-p-ethyl, fentiapropethyl, fluazifop-butyl, fluazifop-p-butyl, haloxifop-ethoxyethyl, haloxifop-methyl, haloxifop-p -methyl, isoxapyrifop, propa "quizafop," quizalofop-ethyl, quizalofop-p-ethyl, quizalofop-tefuril
b28 phenylacetic acids: chlorophenac (fenac)
b29 phenylpropionic acids: chlorophenprop-methyl
b30 protoporphyrinogen-IX-oxidase inhibitors: benzophenap, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, flutiacet-methyl, pyrazoxifen, sulfentrazone, tidiazimin
b31 pyrazoles: nipyraclofen
b32 pyridazines: chloroidazon, maleic hydrazide, norflurazon, pyridate
b33 pyridinecarboxylic acids: clopyralid, dithiopyr, picloram, thiazopyr b34 pyrimidyl ethers pyritiobac acid, pyrithiobac-sodium, KIH-2023, KIH-6127
b35 sulfonamides: flumetsulam, metosulam
b36 sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, chloroimuron-ethyl, chlorosulfuron, cyosulfuron, cyclo-sulfamuron, ethemethyl sulfurone methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfurone, metsulfuron-methyl, nicosulfuronase, primulfuron, prosulfurone, pyrazosulfuron-ethyl, rim-sulfuron, sulfometurone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl
b37 triazines: ametryn, atrazine, aziprotryn, cyanazine, cipracin, desmetryn, dimethametryn, dipropetryn, eglinazin-ethyl, hexazinone, procyanide, prometon, prometryn, propane, secbumeton, simazine, symmetry, terbumeth, terbutryn, terbutylazine, trietacin
b38 triazinones: etiozin, metamitron, metribuzin
b39 triazolecarboxamides: triazophenamide b40 uracils: bromacil, lenacil, terbacil
b41 various: benazoline, benfuresate, bensulide, benzofluoro, butamifos, cafenstrole, chlorothal ^ dimethyl (DCPA), cinmetilin, dichlobenil, endothall, fluorobentranil, mefluidide, perfluidone, piperophos
or its ecologically tolerated salts.
The herbicidal mixture according to the invention has a super-oxidative synergetic action and is selective against "those crop plants" which tolerate individual substances.
Sulfonylureas of the formula I "which are especially preferred with respect to their synergistic herbicidal action are those, where
R means C? 2CH3, C02C2H5, C02iC3H7, CF3, CFH; OS02CH3, OS02N (CH3) 2, Cl, N02, S02N (CH3) 2, S02CH3 and N (CH3) S02CH3
R2 means hydrogen, Cl, F or C? -C2-alkyl
R3 means CF2H, 0CF3, 0CF2C1, CF2C1, CF3 or F
R4 means 0CH3, OC2H5, OCF3, 0CF2C1; CF3, Cl, F, NH (CH3), N (CH3) 2 or C? -C2-al "chyl
R5 is hydrogen means N or CH
n is 0 or 1.
Preferred compounds of the formula I are summarized in the following table.
Table
Preferred compounds (b) are, for example:
Bromobutide Dimetenamide Isoxaben Propane Glufosinate-ammonium Glyphosate Sulfosate Mefenacet 2,4-D 2,4-DBEE 2,4-DBEE Dichloroprop Dichloroprop-p Dichloroprop-p (2,4-DP-P) Fluroxipyr MCPA Mecoprop Mecoprop-p Dicamba Bentazone Clomazone Diflufenican Sulcotrione Phenmedipham Thiobencarb Quinclorac Quinmerac Acetochlor Alachlor Acid Butachlor Acid Metabolite Methochloride Pretilachlor Butroxydim Caloxidim Cletodim Cycloxydim Sethoxydim Tralkoxydim 2-. { 1- [2- (4-chlorophenoxy) propyloxyimino] butyl} -3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl) -2-cyclohexen-l-one Pendi etalin Acifluorophen-sodium Bifenox Fluoroglycofen-ethyl Fomesafen Lactofen chlorotoluron Cycluron Dymron Isoproturon Metabenzthiazuron Imazaquin Imazetabenz-methyl Imazetapyr Bromoxinil Ioxinil Clodinafop Cyhalofop- butyl Fenoxiprop-ethyl Fenoxaprop-p-etiol Haloxifop-p-methyl Cinidon-ethyl Flumiclorac-pentyl Flumipropyn Flutiacet-methyl Pyridate Clopyralide Bispyribac-sodium KIH-8555 KUH- 20 Flumetsulam Metosulam Amidosulfuron Azimsulfuron Bensulfuron-methyl chloroimuron-ethyl chlorosulfuron Cinoslufurone cyclosulfamurone ethoxysulfuronase Flazasulfuron Halosulfuron-methyl HOE-107925 Imazosulfuron Metsulfuron-methyl Nicosulfuron Primisulfuron Prosulfuron Pyrazosulfuron-ethyl Rimsulfuron tifensulfuron-meyl Triasulfuron tribenuron-methyl Atracin Cyanazine Terbutylazine Benazoline Benfuresate Cafenstrole Cinemethiline Ammonium-Bentazone Cloquintocet ET-751 F-8426 KPP-314
The following compounds are especially preferred: 2, 4-D Dichloroprop-P MCPA Mecoprop-p Dicamba Bentazone Diflufenican Sulcotrione Quinclorac Caloxidim Cycloxydim Sethoxydim 2-. { 1- [2- (4-chlorophenoxy) propyloxyimino] butyl} -3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl) -2-cyclohexen-l-one Acifluorophen-sodium fluoroglycofen-ethyl Bromoxinyl Fenoxiprop-ethyl Cinidon-ethyl Amidosulfuron Bensulfuron-methyl Metsulfuron-methyl Nicosulfuron Pyrazosulfuron-ethyl Rimsulfuron Triasulfuron tribenuron-methyl Atracta Terbutilacin Ammonium-Bentazone Cloquintocet
The following compounds are especially preferred: Dichloroprop-P Mecoprop-P Ammonium-Bentazone Bentazone Diflufenican Quinclorac 2- (1- [2- (4-chlorophenoxy) propyloxyimino] butyl) -3-hydroxy-5 - (2H-tetrahydrothiopyran-3) -yl) -2-cyclohexen-1-one Caloxidim Cycloxydim Sethoxydim fluorooglycofen-ethyl Cinidon-ethyl Nicosulfurone Pyrazosulfuron-ethyl Rimsulfurone Atractant Terbutylazine.
The present invention also relates to products which contain at least one herbicidal active amount of a sulfonylurea (a) of the formula I described above or their salts tolerated by the environment, one active synergistic amounts of one of the herbicidal compounds (b) described above or their salt tolerated by the environment, at least one liquid and / or solid support and, if desired, at least one adjuvant.
In the herbicidal mixtures and in the herbicidal products according to the invention, the sulfonylureas of the formula I or their ecologically compatible salts and the herbicidal compounds (b) or their ecologically compatible compounds are used in the proportions by weight necessary to obtain the effect if -energetic desired. Preferably, the mixing ratios between the sulfonylurea of the formula I and one of the herbicidal compounds (b) are from 1 to 1: 0.1 to 1: 40, especially to: 0.2 to 1: 20, in particular to 1. : 0.5 to 1: 15.
The herbicidal mixtures and the herbicidal products according to the invention from the sulfonylureas of the formula I, or their ecologically tolerated salts, for example alkali metals, alkaline earth metals or ammonia and amines and the herbicidal compounds (b), or either its ecologically tolerated salts, for example, of alkali metals, alkaline earth metals or ammonia and of amines are well suited to be used in rice cultivation to change unwanted grasses, without causing damage to crop plants, especially in low application amounts
Considering the many possible methods of application, the herbicidal mixtures and the herbicidal products according to the invention can be used in many other crops to eliminate the growth of unwanted plants therein. The following crops are considered: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum , Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis,
Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sor-ghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
In addition, the herbicidal mixtures and the herbicidal porducts according to the invention can also be used in crops "which by culture or genetic engineering methods have become tolerant to the action of herbicides.
The herbicidal mixtures and the herbicidal products according to the invention can be applied before or after emergence. When the active substances are less tolerated by the crop plants, then application methods can be used in which "the herbicidal products are sprayed with the aid of spraying apparatus in such a way" that they do not fall on the leaves of the plants. sensitive crops, but «that only on the leaves of unwanted plants that grow below the first ones or on the ground covered with unwanted plants (post-directed, lay-by).
The herbicidal mixtures and the herbicidal products according to the invention can be used, for example, in the form of aqueous solutions, powders directly sprayable suspensions, also in the form of suspensions, dispersions or emulsions aqueous, oleic or otherwise, dispersions of oil, pastes, spraying, dusting or granulating agents, by means of spraying, spraying, sprinkling or sprinkling. The forms of application depend on the purpose of the use; In any case, they must guarantee the finest possible distribution of the active substances of the invention.
Inert additives are appropriate mineral fractions from medium boil to high boiling point, such as "kerosene or diesel oil, in addition, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as paraffin, tetrahydronaphthaline, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone. or strongly polar solvents, such as N-methylpyrrolidone or water.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders or granules dispersible in water by the addition of water. To obtain emulsions, pastes or oil dispersions, the substances can be homogenized as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers, in water. However, a humectant, adherent, dispersant or emulsifier and, optionally, a solvent or oil, can also be prepared from the active substance, which can be diluted with water.
Suitable surfactants are alkali metal, alkaline earth metal, ammonium salts of lignin sulphonic acids, for example lignin sulphonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene sulphonic acid, as well as fatty acids, alkyl and alkylaryl sulphonates, sulfates of lauryl ether and fatty alcohol, as well as the salts of sulphonated hexa, hepta and octadecanols, as well as glycol ethers of fatty alcohol, the condensates of sulfonated naphthalene and their derivatives with formaldehyde, the condensates of naphthalene or of naphthalic acids -sulfinsulphonates with phenol and formaldehyde, polyoxyethylenectyl-phenol ethers, isooctylphenol, octylphenol or nonylphenol ethoxylated, alkylphenol polyglycol ethers, tributylphenylpolyolol ethers, alkylaryl polyol alcohols, iso-tridecyl alcohol, fatty alcohol condensates eti-wood, ethoxylated castor oil, polyoxyethylene alkyl ethers, pol ioxypropylene, acetal polyglycol ether lauryl alcohol, sorbitol esters, sulphite residual liquors and methylcellulose.
The spraying, spraying and atomizing agents can be obtained by mixing the active substances together with a solid support.
Granules, eg coated granules, impregnates and homogeneous granules can be prepared by bonding the active substances with solid supports. Appropriate solid supports are mineral earth, such as silica gel, silicic acids, silicic gels, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and plant products, such as stone powders, tree bark powders, wood and nut shell powders, cellulose powders or other solid supports.
The formulations generally contain 0.01 to 95% by weight, preferably 0.5 to 90% by weight of the herbicidal mixture.
Furthermore, it may be useful to apply the mixtures or the herbicidal products according to the invention mixed with other plant protection products, for example with a product for controlling pests or fungi or bacteria. It is also interesting the miscibi-lidad with solutions of mineral salts, "which are used to ali-viar nutritive deficiencies or in microelements. You can also add oils and non-phytotoxic oil concentrates.
The amounts of application in pure herbicide mixture, namely without the formulation aids, amount, depending on the object to be combated, of the season, of the plants to be combated and their growth status, at 0.01 to 5 kg / has, preferably 0.03 to 4 kg / ha, especially 0.1 to 3.0 kg / ha of active substance (sa).
The herbicide products are applied to the plants mainly by spray, leaf ation. The application can be carried out in this case using water as support, using the usual techniques and spray quantities of approx. 100 up to 1000 1 / ha. It is also possible to use the products in the procedures called "Low Volume" and "Ultra-low-Volume" as well as the application of so-called granules.
Application examples
The herbicidal mixtures are applied after the emergence (treatment of the leaves), using the sulfonylurea derivatives as 10 to 75% granules and the herbicidal compounds in the formulation, in which it is present as a commercial product.
These are trials in the open field in small plots in a sandy loam (pH 6.2 to 7.0) or sandy clay (pH 5.0 to 6.7) as a substrate.
Weeds have different heights and states of growth, on average they have a height of 5 to 20 cm, depending on their form of growth.
The herbicidal products are used alone or together, in the latter case partly as tank mixes, partly as ready formulations. The application is carried out in water (350 1 / ha) as distribution medium, in which «the active substances are emulsified, dissolved or suspended. The herbicide products are applied with the help of a parcel sprayer.
The trial period lasts 3 to 8 weeks, but cultures are also observed after this period.
The damage caused by the herbicide products is evaluated according to a graduated scale of 0% up to 100%, compared to untreated control plots, meaning 0 no damage and 100 the total destruction of the plants.
In the following examples the action of the herbicidal products to be used according to the invention is demonstrated, without it being possible to exclude the possibility of other types of applications with them.
In these tests, it is calculated according to the method of S.R. Colby (1967): Calculating synergistic and antagonistic responses of herbicid combinations, Weeds 15, pgs. 20 and next the E value to be expected in an additive effet of the individual active substances.
The calculation is made based on the following formula
XY E = X + Y 100 where
X = means the effect in percent achieved with preparation A with an application amount at Y = means the effect in percent achieved with preparation B with an application amount b E = means the effect to be expected (in%) when A + B is used in the application quantities a + b.
When the observed value is greater than the value E calculated according to Colby, then there is a synergetic action.
The herbidic products have a higher herbicidal effect than the value to be expected according to Colby from the observed effects of the individual components when they are used alone.
Claims
1. Herbicidal mixture containing
a) at least one derivative of the sulfonylurea of the formula
I
wherein the substituents have the following meanings:
Ri Ci-Cß-alkyl, which may carry one to five of the following groups: methoxy, ethoxy, SO2CH3, cyano, chloro, fluoro, SCH3, S (0) CH3;
halogen;
a group ER6, where E means O, S or NR7;
COOR8;
N02;
S (0) oR9, S02NRl ° RH, CONRlORll;
R2 hydrogen, C? -C4-alkyl, C2-C -al "quenyl, C2-C4-al" quinyl, halogen, C? -C4-alkoxy, C? -C4-halogenoalkoxy; C? -C4-halogenoalkyl, a C? -C2-alkylsulfonyl, nitro, cyano or C? -C4-alkylthio group,
R3 F, CF3, CF2C1, CF2H, OCF3, 0CF2C1 O, when R1 means CO2CH3 and R2 means at the same time fluoro, Cl, or, when Rx means CH2CF3 or CF2CF3, methyl, or, when R4 means 0CF3 or
0CF2C1, OCF2H or 0CF2Br;
R4 C? -C-alkoxy, C? -C2-al "chyl, C? -C2-alkylthio,
C? -C2-alkylamino, di-C? -C2-alkylamino, halogen, C? -C2-haloalkyl, C? -C2-halogenoalkoxy,
R5 hydrogen, C? -C2-alkoxy, C? -C4-alkyl;
R6 C? -C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which can carry from 1 to 5 halogen atoms, with the exception of allyl, difluoromethoxy, chlorodifluoromethoxy and 2- chloroethoxy, when E means O or S; furthermore, it means R6, when E is O or NR, additionally methylsulphonyl, ethylsulphonyl, trifluoromethylsulfonyl, allylsulfonyl, propargyl sulfonyl or dimethylsulfamoyl;
R7 hydrogen, methyl or ethyl R8 a Ci-Ce-alkyl group which can carry up to three of the following radicals: halogen, C? -C4-alkoxy, C? -C4-alkylthio, C? -C -haloalkoxy, C C4-alkoxy-C? -C2-alkoxy, C3-C-cycloalkyl and / or phenyl; a Cs-C7-cycloalkyl group which can carry up to three C? -C4-alkyl groups; C3-C6-alkenyl or C3-C6-alkynyl;
R9 a Ci-Cß-alkyl group which can carry from one to three of the following radicals: halogen,
C? -C-alkoxy, C? -C4-alkylthio, C? -C4-haloalcoxy, C? -C4-alkoxy-C? -C2-alkoxy, C3-C-cycloalkyl and / or phenyl; a C5-C-cycloalkyl group that can carry one to three C? -C4-alkyl groups; a C2-C6-alkenyl group or a C3-C6-alkynyl group;
Ri ° hydrogen, a C? -C2-alkoxy group, a Ci-Cg-alkyl group or R10 together with Rn forms a C4-C-alkylene chain where a methylene group can be substituted by an oxygen atom or a C group C4-alkylimino;
Rii a C? -C4-alkyl group which can carry from one to four halogen or C? -C4-alkoxy radicals; C3-C6-cycloalkyl
0
N, CH or its ecologically tolerated salts,
an active synergistic amount of at least one herbicidal compound of groups bl to b41
bl 1, 3,4-thiadiazoles: butidazoles, ciprazoles
b2 alidochlor amides (CDAA), benzoylprop-ethyl, bromobutides, chlorothiamide, dimepiperates, dimethenamid, diphenamide, ethobenzanide (benzchlomet), flam-prop-methyl, fosamine, isoxaben, monalide, naptalame, propyl ammonium, propanil
b3 aminophosphoric acid: bilanafos, (bialafos), buminafos, glufosinate-ammonium, glyphosate, sulfosate
b5 anuidas: anilofos, mefenacet
b6 aryloxyalkanoic acids: 2, 4-D, 2,4-DB, clomeprop, dichloroprop, dichloroprop-P, dichloroprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluorooxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr b7 benzoic acids: cloroamben, dicamba
b8 benzothiadiazinones: bentazone
b9 bleacher: clomazone (dimethazone), diflufenican, fluorochloro- ronone, flupoxam, fluridone, pyrazolate, sulcopione (chloromesulone)
carbamates: asulam, barban, butilate, carbetamid, chlorobufam, chloropropham, cycloate, desmedipharm, diallate, EPTC, esprocarb, molinate, orbencarb, pebulate, phenisopham, phenmedipham, propham, prosulfocarb, pyributicarb, sulphonate (CDEC), terbucarb, ti- obencarb (benthiccarb), thiocarbazil, triallate, vernolate
bll acids «quinolinecarboxylic acids: quinelorac, quinmerac
bl2 chloroacetanilides: acetochlor, alachlor, butachlor, butenachlor, dietyl ethyl, dimethachlor, metazachlor, metolachlor, pretilachlor, propachlor, prynachlor, tertiary, thenilchlor, xylachlor
bl3 cyclohexenones: alloxidim, caloxidim, clethodim, cloproxydim, cycloxydim, sethoxydim, tralcoxydim, 2-. { 1- [2- (4-chlorophenoxy) propyloxyimino] butyl} -3-hydroxy-5- (2H-tetrahydrothiopran-3-yl) -2-cyclohexen-l-one
bl4 dichloropropionic acids: dalapon
bl5 dihydrobenzofurans: etofumesate
bl6 dihydrofuran-3-ones: flurtamone
bl7 dinitroanilines: benefin, butralin, dinitramm, etalfluralin, flu- chloroaline, isopropalin, nitralin, oryzalin, pen- dimetalin, prodiamine, profluralin, trifluralin
bl8 dinitrophenols: bromophenoxy, dinoseb, dinoseb-acetat, dinoterb, DNOC
bl9 diphenyl ethers: acifluorofen-sodiio, aclonifen, bifenox, chloronitrofen (CNP), diphenoxuron, ethoxifen, fluoroodi'en, fluoroglycofen-ethyl, fomesafen, furiloxifen, lactofen, nitrophen, nitrofluorofen, oxyfluorofen b20 dipyridylenes: cyperquat, difenzoquat- methylsulf to, di «quat, paraquat hydrochloride
b21 ureas: benzthiazurone, buturone, chlorobromuron, chloro-oxurone, chlorotoluron, cumiluron, dibenzyluron, cyclurone, dimefurone, diurone, dymrona, etidimuron, fenurone, fluorometurone, isoproturon, isourone, karbutylate, linurone, metabenzthiazurone, methobenzurone , methoxuron, monolinuron, monuron, neburone, siduron, tebutiurone, trimeturon
b22 imidazoles: isocarbamide
b23 imidazolinones: imazametapyr, imazapyr, imaza «quin, imazetabenz-methyl (imazame), imazetapyr
b24 oxadiazoles: metazoles, oxadiargyl, oxadiazone
b25 oxiranes: tridiphane
b26 phenols: bromoxynil, ioxinyl b27 phenoxyphenoxypropionates: clodinafop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fentiaproperyl, fluazifop-butyl, f luazifop-p-butyl, haloxypho-ethoxyethyl, haloxifop-methyl, haloxifop-p-methyl, isoxapyrifop, propaquizafop, quizalo-fop-ethyl, quizalofop-p-ethyl, quizalofop-tefuril
b28 phenylacetic acids: chlorophenac (fenac)
b29 phenylpropionic acids: chlorophenprop-methyl
b30 protoporphyrinogen-IX-oxidase inhibitors: benzophenap, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, lupropacil, flutiacet-methyl, pyrazoxifen, sulfentrazone, thidiazimide
b31 pyrazoles: nipyraclofen
b32 pyridazines: chloroidazon, maleic hydrazide, norflurazon, pyridate
b33 pyridinecarboxylic acids: clopyralid, dithiopyr, picloram, thiazopyr b34 pyrimidyl ethers pyritiobac acid, pyrithiobac-sodium, KIH-2023, KIH-6127
b35 sulfonamides: flumetsulam, metosulam
b36 sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, chloroimuron-ethyl, chlorosulfuron, cyno-sulfuronase, cyclo- sulfamuron, ethemethyl sulfurone methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, py- razosulfuron-ethyl, rimsulfuron, sulfometurone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl
b37 triazines: ametryn, atrazine, aziprotryn, cyanazine, cyprocine, desmetryn, dimethametryn, dipropetryn, egininazine-ethyl, hexazinone, procyanid, prometon, prometryn, propane, secbumeton, simazine, symmetry, terbumeton, terbutryn, terbutylazine , trietacina
b38 triazinones: etiozin, metamitron, metribuzin
b39 triazolecarboxamides: triazophenamide b40 uracils: bromacil, lenacil, terbacil
b41 various: benazoline, benfuresate, bensulide, benzofluoro, butamifos, cafenstrole, chlorot-al-dimethyl (DCPA), cinmetilin, dichlobenil, endothall, fluorobentranil, mefluidide, perfluidone, pipero-phos
or its ecologically tolerated salts.
The herbicidal mixture according to claim 1, which contains a sulfonylurea of the formula I, in which
R1 means C02CH3, C02C2H5, C02iC3H7, CF3, CF2H, CH2CF3, CF2CF3, OSO2CH3, OS02N (CH3) 2, Cl, N02, S02N (CH3) 2, SO2CH3, S02C2H5 and N (CH3) S02CH3,
R2 means hydrogen, halogen or methyl,
R3 means CF2H, 0CF3, 0CF2C1, CF3 or, when R is
C02CH3 and R2 means both fluorine, Cl, or when R1 means F3, CH2CF3 or CF2CF3, methyl,
R4 means OCH3, R5 hydrogen and
Z means N or CH.
Herbicidal mixture according to claim 1 or 2, which contains a sulfonylurea of the formula I, in which Ri means halogen, an ER6 group, a C02R8, S02CH3 or S02C2H5 group,
R2 means hydrogen,
R3 means F,
R4 means OCF3, 0CF2C1, OCH3,
R5 means hydrogen,
R6 and R8 have the meanings indicated in claim 1, and
Z means N or CH.
Herbicidal mixture according to one of claims 1 to 3, containing a sulfonylurea of the formula I, in which
Ri means CF3,
R2 means hydrogen,
R3 means CF3,
R4 means 0CH3,
R5 means hydrogen and
Z means N.
Herbicidal mixture according to one of claims 1 to 4, containing at least one herbicidal compound (b) from 1 group: Bromobutide, Dimethenamid, Isoxaben, Propanil, Glufosi-nate-Ammonium, Glyphosate, Sulfosate, Mefenacet, 2, 4 -D, 2, 4-DB, 2,4-DBEE, Dichlorprop, Dichlorprop-p (2,4-DP-P), Fluroxypyr, MCPA, Mecoprop, Mecoprop-p, Dicamba, Bentazon, Clomazone, Diflufenican, Sulcotrione, Phenmedipham, Thiobencarb, Quinclorac, Quinmerac, Acetoch-lor, Alachlor, Butachlor, Metazachlor, Metolachlor, Preti-lachlor, Butroxydim, Clethodim, Cycloxydim, Sethoxydim, Tralkoxydim, Caloxydim, 2-. { 1- [2- (4-chlorophenoxy) propyloxy-mino] butyl} -3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl) -2-cyclohexen-1-one, Pendimethalin, Acifluorophen-sodium, Bife-nox, fluorooglycofen-ethyl, Fomesafen, Lactofen, Chlorto-luron, Cycluron , Dymron, Isoproturon, Methabenzthiazuron, Imazaquin, Imazethabenz-methyl, Imazethapyr, Bromoxynil, loxynil, Clodinafop, Cyhalofop-butyl, Fenoxyprop-ethyl, Fenoxaprop-p-ethyl, Haloxyfop-p-methyl, Cinidon-ethyl, Flumiclorac-pentyl, Flumipropyn , Fluthiacet-methyl, Pyridate, Clopyralid, Bispyribac-sodium, KIH-8555., KUH-920, Flumetsula, Metosulam, Amidosulfuron, Azimsulfuron, Ben-sulfuron-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cinos-lufuron, Cyclosulfamuron, Ethoxysulfuron, Flazasulfuron, Halosulfuron-methyl, HOE-107925, Imazosulfuron, Metsulfu-ron-methyl, Nicosulfuron, Primisulfuron, Prosulfuron, Py-razosulfuron-ethyl, Rimsulfuron, thifensulfuron-methyl, Triasulfuron, Tribenuron-methyl, Atrazin, Cyanazine, Ter-butylazin, Benazolin, Benfuresate, Cafenstrole, Cinemthy-.lin, Ammonium-Bentazon, Clo «quintocet, ET -751, F-8426,
KPP-314.
6. Herbicidal mixture according to one of claims 1 to 5, which contains at least one herbicidal compound (b) from the group: 2, 4-D, MCPA, Dichlorprop-p, Mecoprop-p, Dicamba, Bentazon, - Diflufenican, Sulcotrione , Quinclorac, Caloxydim, Cycloxydim, Sethoxydim, 2-. { l- [2- (4-chlorophenoxy) propyloxy-mino] butyl} -3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl) -2-cyclohexen-1-one, Acifluorophen-sodium, fluorooglycofen-ethyl, Bromoxynil, Fenoxyprop-ethyl, Cinidon-ethyl, Amido-sulfuron, Bensulfuron -methyl, Metsulfuron-methyl, Nicosulfuron, Pyrazosulfuron-ethyl, Rimsulfuron, Triasulfuron, Tribenuron-methyl, Atrazin, Terbutylazin, ammonium-bentazone, Clocruintocet.
7. The herbicidal mixture according to one of claims 1 to 6, which contains a sulfonylurea (a) of the formula I and one or more herbicidal compounds (b) in the weight ratio of 1: 0.1 to 1: 40.
8. The herbicidal mixture according to claim 7, which contains a sulfonylurea (a) of the formula I and one or more herbicidal compounds (b) in the weight ratio of 1: 0.2 to 1: 20.
9. Herbicidal product, containing a quantity - herbicidal active of a sulfonylureas (a) of the formula I according to one of claims 1 to 4, a synergistic active amount of at least one herbicidal compound (b) according to one of the claims 1, 5 or 6, at least one liquid and / or solid support and, if desired, at least one adjuvant.
Herbicidal product according to claim 9, characterized in that they contain the sulfonylurea (a) of the formula I and one or more herbicidal compounds (b) in the weight ratio of 1: 0.1 to 1: 40.
Herbicidal product according to claim 9, characterized in that it contains the sulfonylurea (a) of the formula I and one or more herbicidal compounds (b) in the weight ratio of 1: 0.2 to 1: 20.
Process for controlling the growth of unwanted plants, characterized in that a sulfonylurea (a) of the formula I according to one of claims 1 to 4 and one or more herbicidal compounds (b) according to claim 1, are applied simultaneously or successively. , during or after the emergence of unwanted plants.
Process for combating the growth of in-desired plants, characterized in that the leaves of the crop plants and unwanted plants are treated simultaneously or successively with a sulfonylurea (a) of the formula I according to one of claims 1 to 4 and one or various compounds (b) according to claim 1.
Claims (1)
- Summary of the Invention Herbicidal mixture containing a) at least one derivative of the sulfonylurea of the formula I wherein the substituents have the following meanings: Ri Ci-Cß-alguilo, which can carry one to five of the following groups: methoxy, ethoxy, S? 2CH3, cyano, chloro, fluoro, SCH3, S (0) CH3; halogen; a group ER6, where E means O, S or NR7; COOR8; N02; S (0) oR9, S02NRl? RH, CONRl ° Rll; R 2 hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy; C? -C4-halogenoalkyl, a C? -C2-alkylsulfonyl, nitro, cyano or C? -C4-alkylthio group, R3 F, CF3, CF2C1, CF2H, OCF3, 0CF2C1 or, when R1 means CO2CH3 and R2 means at the same time fluoro, Cl, or, when R1 means CH2CF3 or CF2CF3, methyl, or, when R4 means OCF3 or 0CF2C1, OCF2H or 0CF2Br; R4 C? -C-alkoxy, C? -C2-al "chyle, C? -C-alkylthio, C? -C2-alkylamino, di-C? -C2-alkylamino, halogen, C? -C2-haloalkyl, C ? -C2-halogenoalkoxy, R5 hydrogen, C? -C2-alkoxy, C? -C4-alkyl; R6 C? -C4-alkyl, C2-C4-alkenyl, C -Calkynyl or C3-C6-cycloalkyl, which can carry from 1 to 5 halogen atoms, with the exception of allyl, difluoromethoxy, chlorodifluoromethoxy and 2-chloroethoxy, when E means O or S. In addition, it means R6, when E is O or NR, additionally methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, allylsulfonyl, propargyl sulphonyl or dimethylsulphamoyl; R7 hydrogen, methyl or ethyl R8 a C? -C6-alkyl group which can carry up to three of the following radicals: halogen, C? -C4-alkoxy, C? -C-alkylthio, C? -C4-halogenoalkoxy, C? -C4-alkoxy-C? -C2-alkoxy, C3-C7-cycloalkyl and / or phenyl; a C5-C7-cycloalkyl group which can carry up to three C? -C4 alkyl groups; C3 ~ C6-alkenyl or C3-C6-alkynyl; R9 a Ci-Cg-alkyl group which can carry from one to three of the following radicals halogen, C? -C4-alkoxy, C? -C4-alkylthio, C? -C4-haloalkoxy, C? -C4-alkoxy- C C2-alkoxy, C3-C7-cycloalkyl and / or phenyl; a C5-C7-cycloalkyl group which can carry one to three C? -C4 alkyl groups; a C2-C6-alkenyl group or a C3-C6-alkynyl group; Ri ° hydrogen, a C? -C2-alkoxy group, a Ci-C? -alkyl group or Ri? Together with R11 form a C4-C6 ~ alkylene chain where a methylene group can be substituted by an oxygen or a C? -C4-alky1imino group; Rii is a C? -C4-alkyl group which can carry from one to four halogen or C? -C4-alkoxy radicals; C3-C6-cycloalkyl z N, CH or its ecologically tolerated salts, and an active synergistic amount of at least one herbicidal compound of the groups bl to b41 indicated in claim 1, herbicidal products, - as well as a method for controlling the growth of unwanted plants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19534910.5 | 1995-09-20 | ||
| DE19534910A DE19534910A1 (en) | 1995-09-20 | 1995-09-20 | Herbicidal mixtures with a synergistic effect |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX9801955A MX9801955A (en) | 1998-08-30 |
| MXPA98001955A true MXPA98001955A (en) | 1998-11-12 |
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