CS110592A3 - Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives - Google Patents
Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives Download PDFInfo
- Publication number
- CS110592A3 CS110592A3 CS921105A CS110592A CS110592A3 CS 110592 A3 CS110592 A3 CS 110592A3 CS 921105 A CS921105 A CS 921105A CS 110592 A CS110592 A CS 110592A CS 110592 A3 CS110592 A3 CS 110592A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- dimethylsulfamoyl
- carboxylic acid
- methylpyridine
- carbon atoms
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 23
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 152
- 239000000203 mixture Substances 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- -1 n-propyloxy group Chemical group 0.000 claims description 56
- 241000196324 Embryophyta Species 0.000 claims description 51
- 230000002363 herbicidal effect Effects 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 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 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011591 potassium Chemical group 0.000 claims description 6
- 229910052700 potassium Chemical group 0.000 claims description 6
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 239000004550 soluble concentrate Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- QLCLAXJIYIFPMC-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-propoxybenzimidazol-2-yl]-6-methylpyridine-3-carboxylic acid Chemical compound N=1C=2C(OCCC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C(O)=O QLCLAXJIYIFPMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- DJDHHXDFKSLEQY-UHFFFAOYSA-N 5-methylpyridine-3-carboxylic acid Chemical compound CC1=CN=CC(C(O)=O)=C1 DJDHHXDFKSLEQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- RZOKQIPOABEQAM-UHFFFAOYSA-M 6-methylpyridine-3-carboxylate Chemical compound CC1=CC=C(C([O-])=O)C=N1 RZOKQIPOABEQAM-UHFFFAOYSA-M 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical group CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000004546 suspension concentrate Substances 0.000 claims description 3
- 239000004563 wettable powder 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
- 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 description 2
- 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 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- FZOJRZYPOWEVBD-UHFFFAOYSA-N 4,5-dihydro-3h-thieno[3,2-e]benzimidazole Chemical group C1=2N=CNC=2CCC2=C1C=CS2 FZOJRZYPOWEVBD-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 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
- VHPIIJIYVWFCAA-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-propoxybenzimidazol-2-yl]-5-methylpyridine-3-carboxylic acid Chemical compound N=1C=2C(OCCC)=CC=CC=2N(S(=O)(=O)N(C)C)C=1C1=NC=C(C)C=C1C(O)=O VHPIIJIYVWFCAA-UHFFFAOYSA-N 0.000 claims 1
- BWRJWOPYPHBARV-UHFFFAOYSA-N 2-[1-(dimethylsulfamoyl)-4-propoxybenzimidazol-2-yl]quinoline-3-carboxylic acid Chemical compound CN(S(=O)(=O)N1C(=NC2=C1C=CC=C2OCCC)C2=NC1=CC=CC=C1C=C2C(=O)O)C BWRJWOPYPHBARV-UHFFFAOYSA-N 0.000 claims 1
- GZRGSIJJOYLWQG-UHFFFAOYSA-N 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-5-ethylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC2=CC(Cl)=CC=C2N1S(=O)(=O)N(C)C GZRGSIJJOYLWQG-UHFFFAOYSA-N 0.000 claims 1
- XULVHQXHFBNGSC-UHFFFAOYSA-N 2-[5-chloro-1-(dimethylsulfamoyl)benzimidazol-2-yl]-6-methylpyridine-3-carboxylate;propan-2-ylazanium Chemical compound CC(C)[NH3+].N=1C2=CC(Cl)=CC=C2N(S(=O)(=O)N(C)C)C=1C1=NC(C)=CC=C1C([O-])=O XULVHQXHFBNGSC-UHFFFAOYSA-N 0.000 claims 1
- LVZRNHKTXXNFAA-UHFFFAOYSA-N 4,5-dihydro-3h-furo[3,2-e]benzimidazole Chemical group C1=2N=CNC=2CCC2=C1C=CO2 LVZRNHKTXXNFAA-UHFFFAOYSA-N 0.000 claims 1
- 241000796522 Olene Species 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- QKZQJBBZKDVVFI-UHFFFAOYSA-N 4-fluoro-2,1,3-benzoxadiazole Chemical compound FC1=CC=CC2=NON=C12 QKZQJBBZKDVVFI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- BHSSXQLSMUDQIV-UHFFFAOYSA-N 1-(4-methyl-2-nitrophenyl)pyrrole-2,5-dione Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N1C(=O)C=CC1=O BHSSXQLSMUDQIV-UHFFFAOYSA-N 0.000 description 4
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
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- 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 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000005580 one pot reaction Methods 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
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- 244000025254 Cannabis sativa Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 239000000543 intermediate Substances 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
- 238000002156 mixing Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical class C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 2
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- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 1
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- 239000002184 metal Substances 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
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-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
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- 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 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 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
- FTVQJPGTLLVZLJ-UHFFFAOYSA-N pyrrolo[1,2-a]benzimidazol-5-one Chemical compound C1=CC=C2N=C3C(N21)=CC=CC3=O FTVQJPGTLLVZLJ-UHFFFAOYSA-N 0.000 description 1
- QJLQVBWAHWJVBT-UHFFFAOYSA-N pyrrolo[1,2-a]benzimidazol-7-one Chemical compound O=C1C=CC2=NC3=CC=CN3C2=C1 QJLQVBWAHWJVBT-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000007944 thiolates Chemical class 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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919107742A GB9107742D0 (en) | 1991-04-11 | 1991-04-11 | New compositions of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS110592A3 true CS110592A3 (en) | 1992-10-14 |
Family
ID=10693110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS921105A CS110592A3 (en) | 1991-04-11 | 1992-04-10 | Benzimidazolyl derivatives, process of their preparation and herbicidalcompositions containing said derivatives |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0508800A1 (zh) |
| JP (1) | JPH05112557A (zh) |
| KR (1) | KR920019773A (zh) |
| CN (1) | CN1067653A (zh) |
| AU (1) | AU646552B2 (zh) |
| BR (1) | BR9201460A (zh) |
| CA (1) | CA2065198A1 (zh) |
| CS (1) | CS110592A3 (zh) |
| FI (1) | FI921614A7 (zh) |
| GB (1) | GB9107742D0 (zh) |
| HU (1) | HUT60728A (zh) |
| IE (1) | IE921154A1 (zh) |
| IL (1) | IL101549A0 (zh) |
| MA (1) | MA22498A1 (zh) |
| MX (1) | MX9201653A (zh) |
| OA (1) | OA09575A (zh) |
| PL (1) | PL294186A1 (zh) |
| TR (1) | TR26643A (zh) |
| TW (1) | TW213908B (zh) |
| YU (1) | YU37792A (zh) |
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 |
| ATE448226T1 (de) | 2000-09-01 | 2009-11-15 | Novartis Vaccines & Diagnostic | Aza heterocyclische derivate und ihre therapeutische verwendung |
| KR100732206B1 (ko) | 2000-09-11 | 2007-06-27 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 티로신 키나제 억제제로서의 퀴놀리논 유도체 |
| US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
| US7470709B2 (en) | 2002-08-23 | 2008-12-30 | Novartis Vaccines And Diagnostics, Inc. | Benzimidazole quinolinones and uses thereof |
| JP2006511616A (ja) | 2002-11-13 | 2006-04-06 | カイロン コーポレイション | 癌の処置方法およびその関連方法 |
| CN1960731B (zh) | 2004-02-20 | 2011-12-07 | 诺华疫苗和诊断公司 | 调节炎性和转移过程的方法 |
| WO2006124413A2 (en) | 2005-05-13 | 2006-11-23 | Novartis Ag | Methods for treating drug resistant cancer |
| BRPI0610355A2 (pt) | 2005-05-17 | 2010-06-15 | Novartis Ag | métodos par sintetizar compostos heterocìclicos |
| 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 |
| TWI589570B (zh) * | 2011-08-04 | 2017-07-01 | 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 |
| KR102062422B1 (ko) | 2012-12-27 | 2020-01-03 | 수미토모 케미칼 컴퍼니 리미티드 | 융합된 옥사졸 화합물 및 그의 해충 방제를 위한 용도 |
| 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 |
| EP2961275A4 (en) * | 2013-02-13 | 2016-07-27 | Sumitomo Chemical Co | PEST CONTROL COMPOSITION AND USE THEREOF |
| TWI793831B (zh) * | 2020-10-29 | 2023-02-21 | 日商日本農藥股份有限公司 | 具肟基之含氮縮合雜環化合物及含有該化合物之農園藝用除草劑、以及彼等之使用方法 |
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 |
| 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 MA MA22780A patent/MA22498A1/fr unknown
- 1992-04-10 OA OA60183A patent/OA09575A/en unknown
- 1992-04-10 PL PL29418692A patent/PL294186A1/xx unknown
- 1992-04-10 JP JP4091018A patent/JPH05112557A/ja active Pending
- 1992-04-10 YU YU37792A patent/YU37792A/sh 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 TR TR92/0333A patent/TR26643A/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 MX MX9201653A patent/MX9201653A/es unknown
- 1992-04-10 IE IE115492A patent/IE921154A1/en 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 |
|---|---|
| EP0508800A1 (en) | 1992-10-14 |
| FI921614A0 (fi) | 1992-04-10 |
| HU9201235D0 (en) | 1992-07-28 |
| OA09575A (en) | 1993-01-31 |
| IL101549A0 (en) | 1992-12-30 |
| CA2065198A1 (en) | 1992-10-12 |
| KR920019773A (ko) | 1992-11-20 |
| AU646552B2 (en) | 1994-02-24 |
| BR9201460A (pt) | 1992-12-01 |
| GB9107742D0 (en) | 1991-05-29 |
| MA22498A1 (fr) | 1992-12-31 |
| TW213908B (zh) | 1993-10-01 |
| CN1067653A (zh) | 1993-01-06 |
| TR26643A (tr) | 1995-03-15 |
| MX9201653A (es) | 1992-11-01 |
| HUT60728A (en) | 1992-10-28 |
| JPH05112557A (ja) | 1993-05-07 |
| YU37792A (sh) | 1994-06-10 |
| FI921614A7 (fi) | 1992-10-12 |
| IE921154A1 (en) | 1992-10-21 |
| AU1475292A (en) | 1992-10-15 |
| PL294186A1 (en) | 1993-04-19 |
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