CH653329A5 - Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation. - Google Patents
Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation. Download PDFInfo
- Publication number
- CH653329A5 CH653329A5 CH1157/82A CH115782A CH653329A5 CH 653329 A5 CH653329 A5 CH 653329A5 CH 1157/82 A CH1157/82 A CH 1157/82A CH 115782 A CH115782 A CH 115782A CH 653329 A5 CH653329 A5 CH 653329A5
- Authority
- CH
- Switzerland
- Prior art keywords
- thiazolyl
- methanol
- radical
- compounds
- benzyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001298 alcohols Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 oct-cyano (2-benzyl 5-thiazolyl) methanol Chemical compound 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- QMCGUQMAJDZBAM-UHFFFAOYSA-N (2-benzyl-1,3-thiazol-4-yl)methanol Chemical compound OCC1=CSC(CC=2C=CC=CC=2)=N1 QMCGUQMAJDZBAM-UHFFFAOYSA-N 0.000 claims description 6
- 150000004678 hydrides Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- SJRIITISXFXAMS-UHFFFAOYSA-N ethyl 2-benzyl-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(CC=2C=CC=CC=2)=N1 SJRIITISXFXAMS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- CJXBHFANXQMZBF-UHFFFAOYSA-N 2-phenylethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1 CJXBHFANXQMZBF-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 230000009102 absorption Effects 0.000 description 19
- 238000010521 absorption reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000012141 concentrate Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000002198 insoluble material Substances 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- JVQGDYICRHZZTO-UHFFFAOYSA-N (2-phenoxy-1,3-thiazol-4-yl)methanol Chemical compound OCC1=CSC(OC=2C=CC=CC=2)=N1 JVQGDYICRHZZTO-UHFFFAOYSA-N 0.000 description 5
- YCCGJWDLYVDAGX-UHFFFAOYSA-N (2-phenoxy-1,3-thiazol-5-yl)methanol Chemical compound S1C(CO)=CN=C1OC1=CC=CC=C1 YCCGJWDLYVDAGX-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 239000000460 chlorine Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LTCAMJOUWGMXSQ-UHFFFAOYSA-N 2-phenoxy-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(OC=2C=CC=CC=2)=N1 LTCAMJOUWGMXSQ-UHFFFAOYSA-N 0.000 description 3
- BMXGMWGLALFECH-UHFFFAOYSA-N 2-phenoxy-1,3-thiazole-5-carbaldehyde Chemical compound S1C(C=O)=CN=C1OC1=CC=CC=C1 BMXGMWGLALFECH-UHFFFAOYSA-N 0.000 description 3
- FSNSVTQGVPCJNA-UHFFFAOYSA-N 3-(chloromethyl)-5-phenoxy-1,2,4-thiadiazole Chemical compound ClCC1=NSC(OC=2C=CC=CC=2)=N1 FSNSVTQGVPCJNA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- XQKLMFURVIKDJX-UHFFFAOYSA-N ethyl 2-phenoxy-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(OC=2C=CC=CC=2)=N1 XQKLMFURVIKDJX-UHFFFAOYSA-N 0.000 description 3
- UGZLGCRHVXYZGB-UHFFFAOYSA-N ethyl 2-phenoxy-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OCC)=CN=C1OC1=CC=CC=C1 UGZLGCRHVXYZGB-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VBWHPHJUZDWSQL-UHFFFAOYSA-N (2-benzyl-1,3-thiazol-5-yl)methanol Chemical compound S1C(CO)=CN=C1CC1=CC=CC=C1 VBWHPHJUZDWSQL-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SHQWBLZVUMDPNX-UHFFFAOYSA-N 2-benzyl-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(CC=2C=CC=CC=2)=N1 SHQWBLZVUMDPNX-UHFFFAOYSA-N 0.000 description 2
- FFFMIFUBJZBTCG-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole Chemical compound ClCC1=NSC(Cl)=N1 FFFMIFUBJZBTCG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical group [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OYDPVRNLLQZQFY-YUMQZZPRSA-N (1r,3s)-2,2-dimethyl-3-[(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@H]1C=C1C(=O)SCC1 OYDPVRNLLQZQFY-YUMQZZPRSA-N 0.000 description 1
- CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 1
- MMOPHTBJNNBLFU-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-piperidin-1-ylpropan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCN1CCCCC1 MMOPHTBJNNBLFU-UHFFFAOYSA-N 0.000 description 1
- HXUXKGNBCHSELU-UHFFFAOYSA-N 2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-2-phenylacetonitrile Chemical compound C(#N)C(C1=CC=CC=C1)C=1SC(=CN1)CO HXUXKGNBCHSELU-UHFFFAOYSA-N 0.000 description 1
- GUPOZVHRTJYZCX-UHFFFAOYSA-N 2-chloroethanimidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])CCl GUPOZVHRTJYZCX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 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 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- GILVNZWYCBUGMT-UHFFFAOYSA-N ethyl 2-chloro-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(Cl)=N1 GILVNZWYCBUGMT-UHFFFAOYSA-N 0.000 description 1
- IZIJOEOJKFKHQR-UHFFFAOYSA-N ethyl 2-chloro-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)S1 IZIJOEOJKFKHQR-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- PKAHQJNJPDVTDP-UHFFFAOYSA-N methyl cyclopropanecarboxylate Chemical compound COC(=O)C1CC1 PKAHQJNJPDVTDP-UHFFFAOYSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- WFOPLDPCLHCWRG-UHFFFAOYSA-N o-ethyl 2-phenylethanethioate Chemical compound CCOC(=S)CC1=CC=CC=C1 WFOPLDPCLHCWRG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8103830A FR2500452A1 (fr) | 1981-02-26 | 1981-02-26 | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH653329A5 true CH653329A5 (fr) | 1985-12-31 |
Family
ID=9255649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1157/82A CH653329A5 (fr) | 1981-02-26 | 1982-02-25 | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4501894A (show.php) |
| JP (1) | JPS57156471A (show.php) |
| AU (1) | AU546363B1 (show.php) |
| BE (1) | BE892287A (show.php) |
| CH (1) | CH653329A5 (show.php) |
| DE (1) | DE3207043A1 (show.php) |
| FR (1) | FR2500452A1 (show.php) |
| GB (1) | GB2093840B (show.php) |
| HU (1) | HU191345B (show.php) |
| IT (1) | IT1147646B (show.php) |
| NL (1) | NL8200704A (show.php) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3431272A1 (de) * | 1984-08-25 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Substituierte phenylharnstoffe |
| EP0467840A3 (en) * | 1990-07-18 | 1992-10-28 | Ciba-Geigy Ag | Derivatives of cyclopropyle acetic acid |
| YU128891A (sh) * | 1990-07-27 | 1994-06-10 | Ciba Geigy Ag. | Derivati karboksimetilciklopropana |
| US5693594A (en) * | 1993-05-27 | 1997-12-02 | American Cyanamid Company | Herbicidal thiazole derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1452171A (fr) * | 1965-07-26 | 1966-02-25 | Chimetron Sarl | Cyanhydrines dérivées des thiazoles et thiadiazoles |
| NL130759C (show.php) * | 1965-10-07 | |||
| US3573317A (en) * | 1968-08-12 | 1971-03-30 | Olin Corp | 3-trichloromethyl-5-substituted-1,2,4-thiadiazoles |
| FR2242094B1 (show.php) * | 1973-08-29 | 1977-01-28 | Roussel Uclaf | |
| CA1051906A (en) * | 1973-10-24 | 1979-04-03 | Shionogi And Co. | Thiazole derivatives and production thereof |
| FR2298329A2 (fr) * | 1975-01-22 | 1976-08-20 | Roussel Uclaf | Nouv |
| DE2719561A1 (de) * | 1976-05-05 | 1977-11-17 | Ciba Geigy Ag | Chrysanthemumsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel |
| EP0027913A3 (de) * | 1979-10-26 | 1981-10-21 | Ciba-Geigy Ag | Druckempfindliches oder wärmeempfindliches Aufzeichnungsmaterial |
-
1981
- 1981-02-26 FR FR8103830A patent/FR2500452A1/fr active Granted
-
1982
- 1982-02-23 NL NL8200704A patent/NL8200704A/nl not_active Application Discontinuation
- 1982-02-25 IT IT47869/82A patent/IT1147646B/it active
- 1982-02-25 AU AU80784/82A patent/AU546363B1/en not_active Ceased
- 1982-02-25 BE BE0/207419A patent/BE892287A/fr not_active IP Right Cessation
- 1982-02-25 US US06/352,256 patent/US4501894A/en not_active Expired - Fee Related
- 1982-02-25 GB GB8205541A patent/GB2093840B/en not_active Expired
- 1982-02-25 HU HU82582A patent/HU191345B/hu unknown
- 1982-02-25 CH CH1157/82A patent/CH653329A5/fr not_active IP Right Cessation
- 1982-02-26 JP JP57029116A patent/JPS57156471A/ja active Pending
- 1982-02-26 DE DE19823207043 patent/DE3207043A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2500452B1 (show.php) | 1983-07-18 |
| GB2093840A (en) | 1982-09-08 |
| BE892287A (fr) | 1982-08-25 |
| DE3207043A1 (de) | 1982-09-16 |
| AU546363B1 (en) | 1985-08-29 |
| IT8247869A0 (it) | 1982-02-25 |
| JPS57156471A (en) | 1982-09-27 |
| FR2500452A1 (fr) | 1982-08-27 |
| IT1147646B (it) | 1986-11-19 |
| NL8200704A (nl) | 1982-09-16 |
| GB2093840B (en) | 1985-02-27 |
| HU191345B (en) | 1987-02-27 |
| US4501894A (en) | 1985-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1237135A (fr) | Esters d'acides cyclopropane carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation, leur application a la lutte des parasites des vegetaux et des locaux,les compositions les renfermant et les nouveaux intermediaires obtenus | |
| EP0041021B1 (fr) | Nouveaux dérivés de l'acide cyclopropane carboxylique, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermédiaires obtenus | |
| CA1237134A (fr) | Derives de l'acide cyclopropane carboxylique, leur preparation, leur application a la lutte contre les parasites des vegetaux et des locaux, les compositions les renfermant et les nouveaux intermediaires obtenus | |
| EP0176387B1 (fr) | Nouveaux dérivés du pyrrole, leur procédé de préparation et leur application comme pesticides | |
| EP0281439B1 (fr) | Nouveaux esters d'acides cyclopropanecarboxyliques apparentés à l'acide pyréthrique, leur procédé de préparation et leur application à la lutte contre les parasites | |
| CA1237144A (fr) | Derives de l'acide cyclopropane carboxylique, leur preparation, leur application a lutte contre les parasites des vegetaux les compositions les renfermant et les nouveaux intermediaires obtenus | |
| FR2670087A1 (fr) | Utilisation de thiazolylalkoxyacrylates pour la fabrication de compositions insecticides et/ou acaricides. | |
| EP0556123A1 (fr) | Nouveaux esters pyréthrinoides dérivés d'alcools thiazoliques, leur procédé de préparation et leur application comme pesticides | |
| EP0132168B1 (fr) | Esters d'acides cyclopropane carboxyliques comportant un groupement cyano, procédé et intermédiaires de préparation, leur application comme pesticides et les compositions les renfermant | |
| EP0378026A1 (fr) | Nouveaux dérivés fluorés de l'acide 3-éthényl 2,2-diméthyl cyclopropane carboxylique, leur procédé de préparation, leur application comme pesticides et les compositions les renfermant | |
| CH653329A5 (fr) | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation. | |
| CH637371A5 (fr) | Esters d'acide acetique substitue et d'alcool benzylique substitue leur procede de preparation et les compositions insecticides les renfermant. | |
| EP0018894B1 (fr) | Esters de dérivés de l'alléthrolone et d'acides carboxyliques, leur procédé de préparation et les compositions les renfermant | |
| EP0107570B1 (fr) | Nouveaux dérivés de l'acide cyclopropane carboxylique substitués en 3 par une chaîne vinylique elle-même substituée, leur procédé et leurs intermédiaires de préparation, leur application comme pesticides et les compositions les renfermant | |
| EP0573361B1 (fr) | Procédé de préparation d'esters de l'acide 2,2-diméthyl 3-((Z)-2-(alcoxycarbonyl)ethenyl cyclopropane carboxylique et intermédiaires | |
| WO1989008096A1 (fr) | Nouveaux esters pyrethrinoides portant un noyau indanyle, leur procede de preparation et leur application comme pesticides | |
| EP0105006A1 (fr) | Cyclopropane carboxylates à structure allénique, leur procédé et leurs intermédiaires de préparation, leur application à la lutte contre les parasites et les compositions les renfermant | |
| FR2689886A1 (fr) | Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides. | |
| EP0007255B1 (fr) | Esters d'acides cyclopropane carboxyliques substitués d'alcool alpha-cyané, leur procédé de préparation, les compositions pesticides les renfermant ainsi que leur application à titre de médicaments à usage vétérinaire | |
| EP0557192A1 (fr) | Esters pyréthrinoides, dérivés de l'alcool 6-(trifluorométhyl)benzylique, leur procédé de préparation et leur application comme pesticides | |
| EP0538097A1 (fr) | Nouveaux dérivés de l'acide 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides | |
| FR2500451A1 (fr) | Esters d'alcools heterocycliques derives du thiazole ou du thiadiazole, leur procede de preparation et les compositions pesticides les renfermant | |
| EP0498724A1 (fr) | Nouveaux esters de l'acide 3-(3,3,3-trifluoro 2-chloropropényl) 2,2-diméthyl cyclopropanecarboxylique, leur procédé de préparation et leur application comme pesticides | |
| EP0030505B1 (fr) | Nouvelles lactones substituées par un reste d'acide aminé, leur préparation et leur application au dédoublement de ces lactones et de ces acides aminés | |
| EP0551035A1 (fr) | Nouveaux dérivés de l'acide 2,2-diméthyl cyclopropane carboxylique portant en 3 une chaîne but-1-èn-3-ynyle, leur procédé de préparation et leur application comme pesticides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |