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
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 2
- GKMCOESXWFIGKS-UHFFFAOYSA-N 4H-2,1,3-benzoxadiazol-4-ide Chemical class N=1ON=C2C=1C=CC=[C-]2 GKMCOESXWFIGKS-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- 241001101998 Galium Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000008061 acetanilides Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000005489 dwarf bean Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 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 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- YTGWKOHORKGMHD-UHFFFAOYSA-N n-(2,3-dinitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O YTGWKOHORKGMHD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- NSMXQKNUPPXBRG-SECBINFHSA-N (R)-lisofylline Chemical group O=C1N(CCCC[C@H](O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-SECBINFHSA-N 0.000 description 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- GOWMBYUZXIZENX-CAUSLRQDSA-N 1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hexadecylamino)pyrimidin-2-one Chemical compound O=C1N=C(NCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 GOWMBYUZXIZENX-CAUSLRQDSA-N 0.000 description 1
- KJIODIGXKBFFRW-UHFFFAOYSA-N 1h-benzimidazol-2-yl pyridine-3-carboxylate Chemical compound N=1C2=CC=CC=C2NC=1OC(=O)C1=CC=CN=C1 KJIODIGXKBFFRW-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- SEUOXNQCSYDBKF-UHFFFAOYSA-N 2-phenylmethoxy-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1OCC1=CC=CC=C1 SEUOXNQCSYDBKF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FZRNMFVEXPERKP-UHFFFAOYSA-N 3-ethyl-6-(4-methyl-2-nitrophenyl)pyrrolo[3,4-b]pyridine-5,7-dione Chemical compound O=C1C2=CC(CC)=CN=C2C(=O)N1C1=CC=C(C)C=C1[N+]([O-])=O FZRNMFVEXPERKP-UHFFFAOYSA-N 0.000 description 1
- QKZQJBBZKDVVFI-UHFFFAOYSA-N 4-fluoro-2,1,3-benzoxadiazole Chemical compound FC1=CC=CC2=NON=C12 QKZQJBBZKDVVFI-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000726103 Atta Species 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- 244000104272 Bidens pilosa Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000722731 Carex Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910020364 ClSO2 Inorganic materials 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241000237537 Ensis Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 241001527806 Iti Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241001355178 Setaria faberi Species 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 240000000359 Triticum dicoccon Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 244000067505 Xanthium strumarium Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 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 (https=) |
| JP (1) | JPH05112557A (https=) |
| KR (1) | KR920019773A (https=) |
| CN (1) | CN1067653A (https=) |
| AU (1) | AU646552B2 (https=) |
| BR (1) | BR9201460A (https=) |
| CA (1) | CA2065198A1 (https=) |
| CS (1) | CS110592A3 (https=) |
| FI (1) | FI921614A7 (https=) |
| GB (1) | GB9107742D0 (https=) |
| HU (1) | HUT60728A (https=) |
| IE (1) | IE921154A1 (https=) |
| IL (1) | IL101549A0 (https=) |
| MA (1) | MA22498A1 (https=) |
| MX (1) | MX9201653A (https=) |
| OA (1) | OA09575A (https=) |
| PL (1) | PL294186A1 (https=) |
| TR (1) | TR26643A (https=) |
| TW (1) | TW213908B (https=) |
| YU (1) | YU37792A (https=) |
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 |
| AU5881394A (en) * | 1994-01-08 | 1995-08-01 | Rhone-Poulenc Agriculture Limited | Benzimidazolyl quinoline-3-carboxylate derivatives, intermediates thereto, and their use as herbicides |
| EP1313734B1 (en) | 2000-09-01 | 2009-11-11 | Novartis Vaccines and Diagnostics, Inc. | Aza heterocyclic derivatives and their therapeutic use |
| CZ304344B6 (cs) | 2000-09-11 | 2014-03-19 | Novartis Vaccines & Diagnostics, Inc. | Chinolinonový derivát a jeho použití a farmaceutický prostředek s obsahem tohoto derivátu |
| US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| CA2496164C (en) | 2002-08-23 | 2010-11-09 | Chiron Corporation | Benzimidazole quinolinones and uses thereof |
| AU2003290699B2 (en) | 2002-11-13 | 2009-08-27 | Novartis Vaccines And Diagnostics, Inc. | Methods of treating cancer and related methods |
| US7875624B2 (en) | 2004-02-20 | 2011-01-25 | Novartis Vaccines And Diagnostics, Inc. | Modulating and measuring cellular adhesion |
| CA2608171C (en) | 2005-05-13 | 2014-02-04 | Novartis Ag | Use of quinolinone compounds for treating drug resistant cancers |
| JP5545925B2 (ja) | 2005-05-17 | 2014-07-09 | ノバルティス アーゲー | ヘテロ環化合物の合成方法 |
| MX2007014782A (es) | 2005-05-23 | 2008-02-19 | Novartis Ag | Formas cristalinas y otras formas de las sales de acido lactico de 4-amino-5-fluoro-3-[6-(4-metilpiperazin-1-il)-1h-bencimidazol-2 -il]-1h quinolin-2-ona. |
| 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 |
| EP2938601B1 (en) | 2012-12-27 | 2018-05-16 | Sumitomo Chemical Company Limited | 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 |
| RU2015138924A (ru) * | 2013-02-13 | 2017-03-20 | Сумитомо Кемикал Компани, Лимитед | Композиция для борьбы с вредителями и ее применение |
| KR102871914B1 (ko) * | 2020-10-29 | 2025-10-15 | 니혼노야쿠가부시키가이샤 | 옥심기를 갖는 함질소 축합복소환 화합물 및 상기 화합물을 함유하는 농원예용 제초제 및 이들의 사용 방법 |
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 |
| EP0298029B1 (de) * | 1987-07-01 | 1992-12-02 | Ciba-Geigy Ag | Substituierte Imidazolone mit herbizider Wirkung |
| 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 AU AU14752/92A patent/AU646552B2/en not_active Ceased
- 1992-04-09 TW TW081102739A patent/TW213908B/zh active
- 1992-04-09 IL IL101549A patent/IL101549A0/xx unknown
- 1992-04-10 PL PL29418692A patent/PL294186A1/xx unknown
- 1992-04-10 CS CS921105A patent/CS110592A3/cs unknown
- 1992-04-10 EP EP92303197A patent/EP0508800A1/en not_active Withdrawn
- 1992-04-10 OA OA60183A patent/OA09575A/en unknown
- 1992-04-10 MA MA22780A patent/MA22498A1/fr unknown
- 1992-04-10 HU HU9201235A patent/HUT60728A/hu unknown
- 1992-04-10 YU YU37792A patent/YU37792A/sh unknown
- 1992-04-10 JP JP4091018A patent/JPH05112557A/ja active Pending
- 1992-04-10 IE IE115492A patent/IE921154A1/en unknown
- 1992-04-10 TR TR92/0333A patent/TR26643A/xx unknown
- 1992-04-10 FI FI921614A patent/FI921614A7/fi not_active Application Discontinuation
- 1992-04-10 MX MX9201653A patent/MX9201653A/es unknown
- 1992-04-11 KR KR1019920006068A patent/KR920019773A/ko not_active Withdrawn
- 1992-04-11 CN CN92102670A patent/CN1067653A/zh active Pending
- 1992-04-13 BR BR929201460A patent/BR9201460A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CS110592A3 (en) | 1992-10-14 |
| GB9107742D0 (en) | 1991-05-29 |
| FI921614A7 (fi) | 1992-10-12 |
| IE921154A1 (en) | 1992-10-21 |
| IL101549A0 (en) | 1992-12-30 |
| AU1475292A (en) | 1992-10-15 |
| TW213908B (https=) | 1993-10-01 |
| FI921614A0 (fi) | 1992-04-10 |
| HU9201235D0 (en) | 1992-07-28 |
| BR9201460A (pt) | 1992-12-01 |
| PL294186A1 (en) | 1993-04-19 |
| CN1067653A (zh) | 1993-01-06 |
| KR920019773A (ko) | 1992-11-20 |
| EP0508800A1 (en) | 1992-10-14 |
| MX9201653A (es) | 1992-11-01 |
| AU646552B2 (en) | 1994-02-24 |
| HUT60728A (en) | 1992-10-28 |
| TR26643A (tr) | 1995-03-15 |
| OA09575A (en) | 1993-01-31 |
| JPH05112557A (ja) | 1993-05-07 |
| YU37792A (sh) | 1994-06-10 |
| MA22498A1 (fr) | 1992-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2065198A1 (en) | Herbicides | |
| EP0496630B1 (en) | 2-Cyano-1,3-dione herbicides | |
| EP0527036B1 (en) | 4-Benzoylisoxazole derivatives and their use as herbicides | |
| JP3310039B2 (ja) | 除草剤 | |
| AU654729B2 (en) | Herbicides | |
| AU676576B2 (en) | New compositions of matter | |
| HK1003790B (en) | 4-benzoylisoxazole derivatives and their use as herbicides | |
| EP0634413A1 (en) | Herbicides | |
| US5371064A (en) | Herbicidal 4-benzoylisoxazole derivatives | |
| US6013805A (en) | Pentafluorothio-substituted isoxazoles | |
| EP0588357B1 (en) | Isoxazoles derivatives and their use as herbicides | |
| CA2065197A1 (en) | Herbicides | |
| AP439A (en) | "4-benzoyl isoxazoles and their use as herbcides". | |
| US6369270B1 (en) | Benzoic acid intermediates to 4-benzoylisoxazole herbicides | |
| AU656447B2 (en) | New herbicides | |
| WO1995025105A1 (en) | Isoxazole derivatives and their use as herbicides | |
| CA2177586C (en) | 4-benzoylisoxazoles and their use as herbicides | |
| GB2311288A (en) | Herbicidal pentafluorosulfanyl compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |