CA2065198A1 - Herbicides - Google Patents
HerbicidesInfo
- Publication number
- CA2065198A1 CA2065198A1 CA002065198A CA2065198A CA2065198A1 CA 2065198 A1 CA2065198 A1 CA 2065198A1 CA 002065198 A CA002065198 A CA 002065198A CA 2065198 A CA2065198 A CA 2065198A CA 2065198 A1 CA2065198 A1 CA 2065198A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethylsulphamoyl
- methylpyridine
- carboxylic acid
- carbon atoms
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000004009 herbicide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
- 241000196324 Embryophyta Species 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- -1 methoxy, ethoxy, n-propyloxy Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004550 soluble concentrate Substances 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 2
- PTJHAIRDKTVMMT-UHFFFAOYSA-N 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=CC(Cl)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O PTJHAIRDKTVMMT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000004563 wettable powder Substances 0.000 claims description 2
- XQFMUGDFOSEYOY-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4,5-dimethylbenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O XQFMUGDFOSEYOY-UHFFFAOYSA-N 0.000 claims 1
- RLICNNSWFUACJQ-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4,5-dimethylbenzimidazol-2-yl]quinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C=3N(C4=CC=C(C)C(C)=C4N=3)S(=O)(=O)N(C)C)=NC2=C1 RLICNNSWFUACJQ-UHFFFAOYSA-N 0.000 claims 1
- PALGUBPJTVQCQW-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-ethoxybenzimidazol-2-yl]-5-ethylpyridine-3-carboxylic acid Chemical compound N=1C=2C(OCC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC=C(CC)C=C1C(O)=O PALGUBPJTVQCQW-UHFFFAOYSA-N 0.000 claims 1
- NLHAEQLDYFXEKG-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-ethoxybenzimidazol-2-yl]quinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C=3N(C=4C=CC=C(C=4N=3)OCC)S(=O)(=O)N(C)C)=NC2=C1 NLHAEQLDYFXEKG-UHFFFAOYSA-N 0.000 claims 1
- IDCCYMABHLZRHF-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methoxybenzimidazol-2-yl]-5-ethylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC2=C(OC)C=CC=C2N1S(=O)(=O)N(C)C IDCCYMABHLZRHF-UHFFFAOYSA-N 0.000 claims 1
- CUWMVJNDJRVUFM-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methoxybenzimidazol-2-yl]-5-methylpyridine-3-carboxylic acid Chemical compound N=1C=2C(OC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(O)=O CUWMVJNDJRVUFM-UHFFFAOYSA-N 0.000 claims 1
- XKIPMLRYMMVZPD-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methoxybenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C=2C(OC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O XKIPMLRYMMVZPD-UHFFFAOYSA-N 0.000 claims 1
- STLCWGSTXILUJE-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methoxybenzimidazol-2-yl]quinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C=3N(C=4C=CC=C(C=4N=3)OC)S(=O)(=O)N(C)C)=NC2=C1 STLCWGSTXILUJE-UHFFFAOYSA-N 0.000 claims 1
- FKVLWSZNBIWRJM-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methylbenzimidazol-2-yl]-5-methylpyridine-3-carboxylate;propan-2-ylazanium Chemical compound CC(C)[NH3+].N=1C2=C(C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C([O-])=O FKVLWSZNBIWRJM-UHFFFAOYSA-N 0.000 claims 1
- FUIPPRQJCLZPOW-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methylbenzimidazol-2-yl]-5-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(O)=O FUIPPRQJCLZPOW-UHFFFAOYSA-N 0.000 claims 1
- RGUQDWMWFUZVQS-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-methylbenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O RGUQDWMWFUZVQS-UHFFFAOYSA-N 0.000 claims 1
- QAPNTPOKXPDNDL-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-5-fluorobenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=CC(F)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O QAPNTPOKXPDNDL-UHFFFAOYSA-N 0.000 claims 1
- VDKWAXZKKFJXRM-UHFFFAOYSA-N 2-[4-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C2=C(Cl)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O VDKWAXZKKFJXRM-UHFFFAOYSA-N 0.000 claims 1
- OPBJLUQALKORFP-UHFFFAOYSA-N 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-5-methylpyridine-3-carboxylic acid Chemical compound N=1C2=CC(Cl)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(O)=O OPBJLUQALKORFP-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 239000004495 emulsifiable concentrate Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- LIOXJJWQGJRAEZ-UHFFFAOYSA-M potassium;2-[1-(dimethylsulfamoyl)-4-methylbenzimidazol-2-yl]-5-methylpyridine-3-carboxylate Chemical compound [K+].N=1C2=C(C)C=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C([O-])=O LIOXJJWQGJRAEZ-UHFFFAOYSA-M 0.000 claims 1
- NYGBRWTZYPACLF-UHFFFAOYSA-N prop-2-ynyl 2-[1-(dimethylsulfamoyl)-4-methoxybenzimidazol-2-yl]-6-methylpyridine-3-carboxylate Chemical compound N=1C=2C(OC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(=O)OCC#C NYGBRWTZYPACLF-UHFFFAOYSA-N 0.000 claims 1
- MABTWQLNAJGORM-UHFFFAOYSA-N prop-2-ynyl 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-5-methylpyridine-3-carboxylate Chemical compound N=1C2=CC(Cl)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(=O)OCC#C MABTWQLNAJGORM-UHFFFAOYSA-N 0.000 claims 1
- HBZJEHUAHQMJRC-UHFFFAOYSA-N prop-2-ynyl 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-6-methylpyridine-3-carboxylate Chemical compound N=1C2=CC(Cl)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(=O)OCC#C HBZJEHUAHQMJRC-UHFFFAOYSA-N 0.000 claims 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000879 imine group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000010992 reflux Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000002500 ions Chemical class 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 239000011149 active material Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 5
- 101150047265 COR2 gene Proteins 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- DSPHFASHOJAOKN-UHFFFAOYSA-N 1-[(7-oxobenzo[a]phenalen-2-yl)amino]anthracene-9,10-dione Chemical compound C1=CC2=CC(NC3=C4C(=O)C5=CC=CC=C5C(C4=CC=C3)=O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 DSPHFASHOJAOKN-UHFFFAOYSA-N 0.000 description 3
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical class C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000285774 Cyperus esculentus Species 0.000 description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000021506 Ipomoea Nutrition 0.000 description 3
- 241000207783 Ipomoea Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical compound [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- VASIZKWUTCETSD-UHFFFAOYSA-N manganese(II) oxide Inorganic materials [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FJEVKYZLIRAAKE-UHFFFAOYSA-N n,n-dimethylpyridine-3-carboxamide Chemical compound CN(C)C(=O)C1=CC=CN=C1 FJEVKYZLIRAAKE-UHFFFAOYSA-N 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- WGDRAVMHLDKGGA-UHFFFAOYSA-N prop-2-en-1-imine Chemical compound [CH2]C=C[NH] WGDRAVMHLDKGGA-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919107742A GB9107742D0 (en) | 1991-04-11 | 1991-04-11 | New compositions of matter |
| GB9107742.0 | 1991-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2065198A1 true CA2065198A1 (en) | 1992-10-12 |
Family
ID=10693110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002065198A Abandoned CA2065198A1 (en) | 1991-04-11 | 1992-04-06 | Herbicides |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0508800A1 (enExample) |
| JP (1) | JPH05112557A (enExample) |
| KR (1) | KR920019773A (enExample) |
| CN (1) | CN1067653A (enExample) |
| AU (1) | AU646552B2 (enExample) |
| BR (1) | BR9201460A (enExample) |
| CA (1) | CA2065198A1 (enExample) |
| CS (1) | CS110592A3 (enExample) |
| FI (1) | FI921614A7 (enExample) |
| GB (1) | GB9107742D0 (enExample) |
| HU (1) | HUT60728A (enExample) |
| IE (1) | IE921154A1 (enExample) |
| IL (1) | IL101549A0 (enExample) |
| MA (1) | MA22498A1 (enExample) |
| MX (1) | MX9201653A (enExample) |
| OA (1) | OA09575A (enExample) |
| PL (1) | PL294186A1 (enExample) |
| TR (1) | TR26643A (enExample) |
| TW (1) | TW213908B (enExample) |
| YU (1) | YU37792A (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9108369D0 (en) * | 1991-04-18 | 1991-06-05 | Rhone Poulenc Agriculture | Compositions of matter |
| DE4323916A1 (de) * | 1993-07-16 | 1995-01-19 | Basf Ag | Substituierte 2-Phenylpyridine |
| WO1995018801A1 (en) * | 1994-01-08 | 1995-07-13 | Rhone-Poulenc Agriculture Ltd. | Benzimidazolyl quinoline-3-carboxylate derivatives, intermediates thereto, and their use as herbicides |
| JP4341949B2 (ja) | 2000-09-01 | 2009-10-14 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | アザ複素環式誘導体およびその治療的使用 |
| BRPI0113757B8 (pt) | 2000-09-11 | 2017-11-07 | Chiron Corp | derivados de quinolinona como inibidores de tirosina quinase |
| US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| EP2573079A3 (en) | 2002-08-23 | 2015-03-11 | Novartis AG | Benzimidazole quinolinones and uses thereof |
| SG148864A1 (en) | 2002-11-13 | 2009-01-29 | Chiron Corp | Methods of treating cancer and related methods |
| EP1718306A2 (en) | 2004-02-20 | 2006-11-08 | Chiron Corporation | Modulation of inflammatory and metastatic processes |
| AU2006247803B2 (en) | 2005-05-13 | 2011-12-22 | Novartis Ag | Methods for treating drug resistant cancer |
| CA2608087C (en) | 2005-05-17 | 2013-12-10 | Gabriel Calvin | Methods for synthesizing heterocyclic compounds |
| EP2270000B1 (en) | 2005-05-23 | 2015-07-29 | Novartis AG | Crystalline and other forms of 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one lactic acid salts |
| TWI545119B (zh) | 2011-08-04 | 2016-08-11 | 住友化學股份有限公司 | 稠合雜環化合物及其在病蟲害防制上之用途 |
| CA2896453C (en) | 2012-12-27 | 2021-06-08 | Masaki Takahashi | Fused oxazole compounds and use thereof for pest control |
| TWI621616B (zh) * | 2013-01-31 | 2018-04-21 | 住友化學股份有限公司 | 有害生物防治組成物及有害生物之防治方法 |
| JP2016511220A (ja) * | 2013-02-13 | 2016-04-14 | 住友化学株式会社 | 有害生物防除組成物およびその用途 |
| CN116529240B (zh) * | 2020-10-29 | 2025-06-27 | 日本农药株式会社 | 具有肟基的含氮缩合杂环化合物、含该化合物的农业园艺用除草剂及其使用方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1805548A1 (de) * | 1968-10-26 | 1970-10-08 | Agfa Gevaert Ag | Benzimidazol-Derivate und ihre photographische Verwendung |
| US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
| FR2653432A1 (fr) * | 1989-10-20 | 1991-04-26 | Rhone Poulenc Agrochimie | Herbicides derives de 2-azolyl nicotinate. |
| GB9108369D0 (en) * | 1991-04-18 | 1991-06-05 | Rhone Poulenc Agriculture | Compositions of matter |
-
1991
- 1991-04-11 GB GB919107742A patent/GB9107742D0/en active Pending
-
1992
- 1992-04-06 CA CA002065198A patent/CA2065198A1/en not_active Abandoned
- 1992-04-09 IL IL101549A patent/IL101549A0/xx unknown
- 1992-04-09 AU AU14752/92A patent/AU646552B2/en not_active Ceased
- 1992-04-09 TW TW081102739A patent/TW213908B/zh active
- 1992-04-10 TR TR92/0333A patent/TR26643A/xx unknown
- 1992-04-10 JP JP4091018A patent/JPH05112557A/ja active Pending
- 1992-04-10 EP EP92303197A patent/EP0508800A1/en not_active Withdrawn
- 1992-04-10 IE IE115492A patent/IE921154A1/en unknown
- 1992-04-10 FI FI921614A patent/FI921614A7/fi not_active Application Discontinuation
- 1992-04-10 HU HU9201235A patent/HUT60728A/hu unknown
- 1992-04-10 CS CS921105A patent/CS110592A3/cs unknown
- 1992-04-10 PL PL29418692A patent/PL294186A1/xx unknown
- 1992-04-10 YU YU37792A patent/YU37792A/sh unknown
- 1992-04-10 OA OA60183A patent/OA09575A/en unknown
- 1992-04-10 MA MA22780A patent/MA22498A1/fr unknown
- 1992-04-10 MX MX9201653A patent/MX9201653A/es unknown
- 1992-04-11 CN CN92102670A patent/CN1067653A/zh active Pending
- 1992-04-11 KR KR1019920006068A patent/KR920019773A/ko not_active Withdrawn
- 1992-04-13 BR BR929201460A patent/BR9201460A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL101549A0 (en) | 1992-12-30 |
| MA22498A1 (fr) | 1992-12-31 |
| BR9201460A (pt) | 1992-12-01 |
| MX9201653A (es) | 1992-11-01 |
| OA09575A (en) | 1993-01-31 |
| AU1475292A (en) | 1992-10-15 |
| KR920019773A (ko) | 1992-11-20 |
| PL294186A1 (en) | 1993-04-19 |
| TR26643A (tr) | 1995-03-15 |
| CS110592A3 (en) | 1992-10-14 |
| AU646552B2 (en) | 1994-02-24 |
| FI921614A0 (fi) | 1992-04-10 |
| HU9201235D0 (en) | 1992-07-28 |
| FI921614A7 (fi) | 1992-10-12 |
| GB9107742D0 (en) | 1991-05-29 |
| TW213908B (enExample) | 1993-10-01 |
| CN1067653A (zh) | 1993-01-06 |
| JPH05112557A (ja) | 1993-05-07 |
| YU37792A (sh) | 1994-06-10 |
| EP0508800A1 (en) | 1992-10-14 |
| HUT60728A (en) | 1992-10-28 |
| IE921154A1 (en) | 1992-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |