ZA200100315B - Herbicides with substituted phenylsulfonylureas for controlling weeds in rice. - Google Patents
Herbicides with substituted phenylsulfonylureas for controlling weeds in rice. Download PDFInfo
- Publication number
- ZA200100315B ZA200100315B ZA200100315A ZA200100315A ZA200100315B ZA 200100315 B ZA200100315 B ZA 200100315B ZA 200100315 A ZA200100315 A ZA 200100315A ZA 200100315 A ZA200100315 A ZA 200100315A ZA 200100315 B ZA200100315 B ZA 200100315B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- och
- herbicides
- compounds
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 61
- 241000196324 Embryophyta Species 0.000 title claims description 50
- 235000007164 Oryza sativa Nutrition 0.000 title claims description 50
- 235000009566 rice Nutrition 0.000 title claims description 50
- 240000007594 Oryza sativa Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 92
- 239000000203 mixture Substances 0.000 claims description 68
- 241000209094 Oryza Species 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 241000234646 Cyperaceae Species 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 241000209504 Poaceae Species 0.000 claims description 20
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- -1 1,3- dimethylbutyl Chemical group 0.000 claims description 15
- 239000005504 Dicamba Substances 0.000 claims description 11
- 229940100389 Sulfonylurea Drugs 0.000 claims description 11
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 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 10
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 9
- UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 claims description 9
- 239000005574 MCPA Substances 0.000 claims description 9
- 239000005590 Oxyfluorfen Substances 0.000 claims description 9
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims description 9
- 239000005591 Pendimethalin Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 8
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 6
- 239000005582 Metosulam Substances 0.000 claims description 6
- 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 6
- 239000005586 Nicosulfuron Substances 0.000 claims description 6
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003851 azoles Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000002195 synergetic effect Effects 0.000 claims description 6
- MPPOHAUSNPTFAJ-SECBINFHSA-N (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-SECBINFHSA-N 0.000 claims description 5
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 claims description 5
- 239000005513 Fenoxaprop-P Substances 0.000 claims description 5
- 239000005576 Mecoprop-P Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000011885 synergistic combination Substances 0.000 claims description 4
- 230000009261 transgenic effect Effects 0.000 claims description 4
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 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 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims 5
- 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 5
- 239000005627 Triclopyr Substances 0.000 claims 5
- 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 claims 5
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims 5
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims 5
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 claims 4
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims 4
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims 4
- 239000005469 Azimsulfuron Substances 0.000 claims 4
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims 4
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims 4
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims 4
- 239000005501 Cycloxydim Substances 0.000 claims 4
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 claims 4
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 239000005567 Imazosulfuron Substances 0.000 claims 4
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims 4
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 claims 4
- 239000005588 Oxadiazon Substances 0.000 claims 4
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims 4
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims 4
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims 4
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims 4
- 239000005618 Sulcotrione Substances 0.000 claims 4
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 claims 4
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 claims 4
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 claims 4
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 claims 4
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 claims 4
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 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 4
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims 4
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 claims 4
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 claims 4
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims 4
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 4
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims 4
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims 3
- 239000005595 Picloram Substances 0.000 claims 3
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims 3
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims 3
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 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 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19832017A DE19832017A1 (de) | 1998-07-16 | 1998-07-16 | Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200100315B true ZA200100315B (en) | 2002-11-08 |
Family
ID=7874301
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200100315A ZA200100315B (en) | 1998-07-16 | 2001-01-11 | Herbicides with substituted phenylsulfonylureas for controlling weeds in rice. |
Country Status (27)
Country | Link |
---|---|
US (2) | US6492301B1 (xx) |
EP (1) | EP1096855B1 (xx) |
JP (1) | JP4621353B2 (xx) |
KR (1) | KR100676019B1 (xx) |
CN (2) | CN1314785B (xx) |
AR (1) | AR019782A1 (xx) |
AT (1) | ATE281077T1 (xx) |
AU (1) | AU769790B2 (xx) |
BG (1) | BG65083B1 (xx) |
BR (1) | BR9912829B1 (xx) |
CA (1) | CA2337521C (xx) |
CO (1) | CO5221021A1 (xx) |
CZ (1) | CZ300185B6 (xx) |
DE (2) | DE19832017A1 (xx) |
ES (1) | ES2233061T3 (xx) |
HU (1) | HU229832B1 (xx) |
ID (1) | ID28899A (xx) |
IL (1) | IL140765A0 (xx) |
MX (1) | MX224001B (xx) |
MY (1) | MY126471A (xx) |
PL (1) | PL198867B1 (xx) |
RU (1) | RU2235466C2 (xx) |
SK (1) | SK286315B6 (xx) |
TR (1) | TR200100100T2 (xx) |
UA (1) | UA70954C2 (xx) |
WO (1) | WO2000003597A1 (xx) |
ZA (1) | ZA200100315B (xx) |
Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19520839A1 (de) * | 1995-06-08 | 1996-12-12 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern |
GB9920281D0 (en) * | 1999-08-26 | 1999-10-27 | Collag Ltd | Novel compositions of biologically active agents and their use |
JP2001172107A (ja) * | 1999-12-14 | 2001-06-26 | Mitsubishi Chemicals Corp | 除草剤 |
BRPI0111008B1 (pt) * | 2000-05-22 | 2015-12-15 | Bayer Cropscience Ag | agentes herbicidas seletivos à base de heteroarilóxi acetamidas, seu emprego e seu processo de preparação, bem como processo para o combate de plantas indesejadas |
DE10036184A1 (de) * | 2000-07-24 | 2002-02-14 | Aventis Cropscience Gmbh | Substituierte Sulfonylaminomethylbenzoesäure(derivate) und Verfahren zu ihrer Herstellung |
GB2370096A (en) | 2000-12-18 | 2002-06-19 | Fluid Controls U K Ltd | Constant flow control valve |
HUP0303981A3 (en) * | 2001-01-31 | 2012-10-29 | Bayer Cropscience Ag | Herbicide-safener combination based on isoxozoline carboxylate safeners and its use |
US20030060494A1 (en) * | 2001-05-18 | 2003-03-27 | Nobuyuki Yasuda | Pharmaceutical use of N-carbamoylazole derivatives |
DE10135642A1 (de) | 2001-07-21 | 2003-02-27 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
DE10142336A1 (de) | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide enthaltend ein Tetrazolinon-Derivat |
AR036580A1 (es) * | 2001-09-27 | 2004-09-15 | Syngenta Participations Ag | Composicion herbicida |
PL207276B1 (pl) * | 2001-09-27 | 2010-11-30 | Syngenta Participations Ag | Kompozycja chwastobójcza oraz sposób selektywnego zwalczania chwastów i traw w uprawach roślin użytkowych |
GB2381568A (en) | 2001-10-31 | 2003-05-07 | Fluid Controls U K Ltd | Flow control valve |
DE10157339A1 (de) * | 2001-11-22 | 2003-06-12 | Bayer Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Benzoylpyrazole |
DE10209478A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
WO2004066730A1 (en) * | 2003-01-27 | 2004-08-12 | Plant Research International B.V. | Compositions comprising lignosulfonates for improving crop yields and quality |
CN100496246C (zh) | 2004-06-07 | 2009-06-10 | 辛根塔参与股份公司 | 减轻线虫损害的方法 |
JP2006257063A (ja) * | 2005-03-17 | 2006-09-28 | Maruwa Biochemical Co Ltd | 保存安定性を向上させた油性懸濁除草製剤。 |
AR053563A1 (es) * | 2005-03-21 | 2007-05-09 | Basf Ag | Mezclas insecticidas |
US20110098177A1 (en) * | 2006-03-28 | 2011-04-28 | Novus International Inc. | Methods and compositions of plant micronutrients |
US20070232693A1 (en) * | 2006-03-28 | 2007-10-04 | Novus International, Inc. | Compositions for treating infestation of plants by phytopathogenic microorganisms |
JP5094039B2 (ja) * | 2006-04-20 | 2012-12-12 | バイエルクロップサイエンス株式会社 | 芝生用除草剤組成物 |
US8138122B2 (en) * | 2006-04-28 | 2012-03-20 | Sumitomo Chemical Company, Limited | Herbicidal composition |
CN102027978B (zh) * | 2009-09-28 | 2014-12-10 | 南京华洲药业有限公司 | 一种含烟嘧磺隆的混合除草组合物及其应用 |
WO2011082954A2 (de) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2011082964A1 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
RS55256B1 (sr) | 2009-12-17 | 2017-02-28 | Bayer Ip Gmbh | Herbicidno sredstvo koje sadrži flufenacet |
WO2011082968A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2011082955A2 (de) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
DK2512249T3 (en) | 2009-12-17 | 2016-09-19 | Bayer Ip Gmbh | HERBICIDE AGENTS CONTAINING FLUFENACET |
WO2011082959A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2011082956A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
DK2515658T3 (en) * | 2009-12-17 | 2016-09-12 | Bayer Ip Gmbh | HERBICIDE AGENTS CONTAINING FLUFENACET |
WO2011082953A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2011082957A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
CN102461549B (zh) * | 2010-11-19 | 2013-12-25 | 南京华洲药业有限公司 | 一种含醚磺隆、二氯喹啉酸与氰氟草酯的混合除草剂及其应用 |
CN102461530B (zh) * | 2010-11-19 | 2013-12-25 | 南京华洲药业有限公司 | 一种含醚磺隆、苄嘧磺隆与二甲戊乐灵的混合除草剂及其应用 |
CN102461542B (zh) * | 2010-11-19 | 2013-09-18 | 南京华洲药业有限公司 | 一种含醚磺隆、双草醚与丁草胺的混合除草剂及其应用 |
CN102197812A (zh) * | 2011-04-07 | 2011-09-28 | 北京燕化永乐农药有限公司 | 一类水田新除草剂 |
CN102792959A (zh) * | 2011-05-23 | 2012-11-28 | 山东滨农科技有限公司 | 含有甲基二磺隆和麦草畏的除草剂组合物 |
CN103181396B (zh) * | 2011-09-27 | 2016-01-20 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103190426A (zh) * | 2011-09-27 | 2013-07-10 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103190427A (zh) * | 2011-09-27 | 2013-07-10 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103210941A (zh) * | 2011-09-27 | 2013-07-24 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103190431A (zh) * | 2011-09-27 | 2013-07-10 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103190428A (zh) * | 2011-09-27 | 2013-07-10 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103210951A (zh) * | 2011-09-27 | 2013-07-24 | 娄底农科所农药实验厂 | 一种稻田除草组合物 |
CN103039482A (zh) * | 2011-10-17 | 2013-04-17 | 南京华洲药业有限公司 | 一种含醚磺隆与敌稗的混合除草剂及其应用 |
CN102365967A (zh) * | 2011-12-01 | 2012-03-07 | 联保作物科技有限公司 | 一种小麦田除草组合物及其制剂 |
WO2014001248A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2014001361A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
WO2014001357A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
CN104519737B (zh) | 2012-06-27 | 2016-11-09 | 拜尔农作物科学股份公司 | 含有氟噻草胺的除草剂 |
CN103891747A (zh) * | 2012-12-28 | 2014-07-02 | 青岛锦涟鑫商贸有限公司 | 一种改进的除草剂 |
UA118765C2 (uk) | 2013-08-09 | 2019-03-11 | Байєр Кропсайєнс Акцієнгезелльшафт | Третинні гербіцидні комбінації, що містять дві сульфонілсечовини |
JP6545161B2 (ja) * | 2013-10-17 | 2019-07-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Acc阻害剤を含む除草組成物 |
US9072298B2 (en) * | 2013-11-01 | 2015-07-07 | Rotam Agrochem Intrnational Company Limited | Synergistic herbicidal composition |
CN106413403A (zh) | 2014-03-11 | 2017-02-15 | 爱利思达生命科学公司 | 除草剂组合物 |
CN103988837A (zh) * | 2014-04-10 | 2014-08-20 | 临沂丰邦农业科技有限公司 | 一种园林苗圃除草剂及其使用方法 |
EP2936983A1 (de) | 2014-04-25 | 2015-10-28 | Bayer CropScience AG | Wirkstoffe zur Ertragssteigerung in Baumwollkulturen |
TW201620384A (zh) * | 2014-04-28 | 2016-06-16 | 陶氏農業科學公司 | 由施用合氯氟(haloxyfop)及als抑制劑除草劑之協同性雜草控制 |
CN104126598B (zh) * | 2014-08-25 | 2016-09-07 | 河南远见农业科技有限公司 | 一种小麦田除草剂组合物及应用 |
RU2579201C1 (ru) * | 2014-10-20 | 2016-04-10 | Андрей Рудольфович Предтеченский | Способ получения гумата калия и установка |
US11059015B2 (en) * | 2015-06-10 | 2021-07-13 | Council Of Scientific And Industrial Research | Microcapsules modified with nanomaterial for controlled release of active agent and process for preparation thereof |
DK3319442T3 (da) * | 2015-07-10 | 2021-12-20 | Basf Agro Bv | Fremgangsmåde til bekæmpelse af herbicidresistent eller -tolerant ukrudt |
CN110122150B (zh) * | 2019-05-24 | 2021-07-06 | 四川大学 | 一种治理毛叶钝果寄生对二球悬铃木危害的方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA92970B (en) * | 1991-02-12 | 1992-10-28 | Hoechst Ag | Arylsulfonylureas,processes for their preparation,and their use as herbicides and growth regulators |
DE4209475A1 (de) * | 1992-03-24 | 1993-09-30 | Hoechst Ag | Synergistische Mittel zur Bekämpfung unerwünschten Planzenwuchses |
DE4333249A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Schering Agrevo Gmbh | Neue Mischungen aus Herbiziden und Antidots |
DE4335297A1 (de) * | 1993-10-15 | 1995-04-20 | Hoechst Schering Agrevo Gmbh | Phenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE19520839A1 (de) * | 1995-06-08 | 1996-12-12 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern |
DE19534910A1 (de) * | 1995-09-20 | 1997-03-27 | Basf Ag | Herbizide Mischungen mit synergistischer Wirkung |
DE19642082A1 (de) * | 1996-10-04 | 1998-04-09 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit synergistischer Wirkung |
DE19650955A1 (de) * | 1996-12-07 | 1998-06-10 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit N- [(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl] -5-methylsulfonamidomethyl-2-alkoxycarbonylbenzolsulfonamiden |
DE19834627A1 (de) * | 1998-07-31 | 1998-12-03 | Novartis Ag | Herbizides Mittel |
DE19851854A1 (de) * | 1998-11-10 | 1999-04-15 | Novartis Ag | Herbizides Mittel |
DE19919951A1 (de) * | 1999-04-30 | 1999-09-16 | Novartis Ag | Herbizides Mittel |
-
1998
- 1998-07-16 DE DE19832017A patent/DE19832017A1/de not_active Withdrawn
-
1999
- 1999-07-12 JP JP2000559741A patent/JP4621353B2/ja not_active Expired - Lifetime
- 1999-07-12 ES ES99936516T patent/ES2233061T3/es not_active Expired - Lifetime
- 1999-07-12 WO PCT/EP1999/004881 patent/WO2000003597A1/de active IP Right Grant
- 1999-07-12 PL PL345665A patent/PL198867B1/pl unknown
- 1999-07-12 IL IL14076599A patent/IL140765A0/xx not_active IP Right Cessation
- 1999-07-12 CZ CZ20010200A patent/CZ300185B6/cs not_active IP Right Cessation
- 1999-07-12 RU RU2001104530/04A patent/RU2235466C2/ru active
- 1999-07-12 DE DE59911002T patent/DE59911002D1/de not_active Expired - Lifetime
- 1999-07-12 ID IDW20010118A patent/ID28899A/id unknown
- 1999-07-12 CN CN998102016A patent/CN1314785B/zh not_active Expired - Lifetime
- 1999-07-12 BR BRPI9912829-2A patent/BR9912829B1/pt not_active IP Right Cessation
- 1999-07-12 HU HU0104456A patent/HU229832B1/hu unknown
- 1999-07-12 CN CN200710002369A patent/CN100581364C/zh not_active Expired - Lifetime
- 1999-07-12 SK SK52-2001A patent/SK286315B6/sk not_active IP Right Cessation
- 1999-07-12 TR TR2001/00100T patent/TR200100100T2/xx unknown
- 1999-07-12 AU AU51587/99A patent/AU769790B2/en not_active Expired
- 1999-07-12 EP EP99936516A patent/EP1096855B1/de not_active Expired - Lifetime
- 1999-07-12 KR KR20017000608A patent/KR100676019B1/ko not_active IP Right Cessation
- 1999-07-12 AT AT99936516T patent/ATE281077T1/de not_active IP Right Cessation
- 1999-07-12 MX MXPA01000572 patent/MX224001B/es active IP Right Grant
- 1999-07-12 UA UA2001021086A patent/UA70954C2/uk unknown
- 1999-07-12 CA CA2337521A patent/CA2337521C/en not_active Expired - Lifetime
- 1999-07-14 CO CO99044511A patent/CO5221021A1/es not_active Application Discontinuation
- 1999-07-14 AR ARP990103451A patent/AR019782A1/es active IP Right Grant
- 1999-07-14 US US09/353,701 patent/US6492301B1/en not_active Expired - Lifetime
- 1999-07-15 MY MYPI99003000A patent/MY126471A/en unknown
-
2001
- 2001-01-10 BG BG105138A patent/BG65083B1/bg unknown
- 2001-01-11 ZA ZA200100315A patent/ZA200100315B/en unknown
-
2002
- 2002-09-10 US US10/238,153 patent/US6864217B2/en not_active Expired - Lifetime
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