FR2500452A1 - 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
- FR2500452A1 FR2500452A1 FR8103830A FR8103830A FR2500452A1 FR 2500452 A1 FR2500452 A1 FR 2500452A1 FR 8103830 A FR8103830 A FR 8103830A FR 8103830 A FR8103830 A FR 8103830A FR 2500452 A1 FR2500452 A1 FR 2500452A1
- Authority
- FR
- France
- Prior art keywords
- formula
- attributed
- radical
- compounds
- thiazolyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001298 alcohols Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- -1 HYDROXYL GROUP Chemical group 0.000 claims abstract description 26
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 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 8
- 150000004678 hydrides Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 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 claims description 6
- 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 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 4
- CJXBHFANXQMZBF-UHFFFAOYSA-N 2-phenylethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1 CJXBHFANXQMZBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 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 3
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 claims description 3
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical group [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 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 claims 1
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical group CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 22
- 150000001721 carbon Chemical class 0.000 abstract description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 230000009102 absorption Effects 0.000 description 48
- 238000010521 absorption reaction Methods 0.000 description 48
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- 239000001257 hydrogen Substances 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 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
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- HKHXJOJUZSYKAJ-UHFFFAOYSA-N 2-phenoxy-1,3-thiazole Chemical compound C=1C=CC=CC=1OC1=NC=CS1 HKHXJOJUZSYKAJ-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- 150000001299 aldehydes Chemical class 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
- 239000012141 concentrate Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 2
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 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 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- OBQVIRQQMCDJIO-UHFFFAOYSA-N 2-(2-benzyl-1,3-thiazol-4-yl)-2-hydroxyacetonitrile Chemical compound N#CC(O)C1=CSC(CC=2C=CC=CC=2)=N1 OBQVIRQQMCDJIO-UHFFFAOYSA-N 0.000 description 1
- PXLDJFLSFVPGMB-UHFFFAOYSA-N 2-(2-benzyl-1,3-thiazol-5-yl)-2-hydroxyacetonitrile Chemical compound S1C(C(C#N)O)=CN=C1CC1=CC=CC=C1 PXLDJFLSFVPGMB-UHFFFAOYSA-N 0.000 description 1
- ABCSPNANFXDHDU-UHFFFAOYSA-N 2-benzyl-1,3-thiazole Chemical compound C=1C=CC=CC=1CC1=NC=CS1 ABCSPNANFXDHDU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MKDHSWDOKHSXNF-UHFFFAOYSA-N 2-hydroxy-2-(2-phenoxy-1,3-thiazol-4-yl)acetonitrile Chemical compound N#CC(O)C1=CSC(OC=2C=CC=CC=2)=N1 MKDHSWDOKHSXNF-UHFFFAOYSA-N 0.000 description 1
- UJNPYPORTLSJJV-UHFFFAOYSA-N 2-hydroxy-2-(2-phenoxy-1,3-thiazol-5-yl)acetonitrile Chemical compound S1C(C(C#N)O)=CN=C1OC1=CC=CC=C1 UJNPYPORTLSJJV-UHFFFAOYSA-N 0.000 description 1
- RAQPUQNVEDZZEE-UHFFFAOYSA-N 4-ethyl-2-phenoxy-1,3-thiazole Chemical compound CCC1=CSC(OC=2C=CC=CC=2)=N1 RAQPUQNVEDZZEE-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- FFFMIFUBJZBTCG-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole Chemical compound ClCC1=NSC(Cl)=N1 FFFMIFUBJZBTCG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001035 drying Methods 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
- 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
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 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)
Priority Applications (11)
| 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 |
| NL8200704A NL8200704A (nl) | 1981-02-26 | 1982-02-23 | Heterocyclische alcoholen en functionele derivaten daarvan, alsmede werkwijze voor hun bereiding. |
| BE0/207419A BE892287A (fr) | 1981-02-26 | 1982-02-25 | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation |
| HU82582A HU191345B (en) | 1981-02-26 | 1982-02-25 | Process for production of heterocyclic alcohols and their esther derivatives |
| US06/352,256 US4501894A (en) | 1981-02-26 | 1982-02-25 | Heterocyclic alcohols and their derivatives |
| IT47869/82A IT1147646B (it) | 1981-02-26 | 1982-02-25 | Alcoli eterociclici,loro derivati funzionali,e procedimento per la loro preparazione |
| GB8205541A GB2093840B (en) | 1981-02-26 | 1982-02-25 | Thiazole and thiadiazole alcohols and derivatives thereof |
| CH1157/82A CH653329A5 (fr) | 1981-02-26 | 1982-02-25 | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation. |
| AU80784/82A AU546363B1 (en) | 1981-02-26 | 1982-02-25 | Thiazolyl and (1,2,4)thiadiazoyl methanols and their derivatives |
| DE19823207043 DE3207043A1 (de) | 1981-02-26 | 1982-02-26 | Heterocyclische alkohole und funktionelle derivate sowie deren herstellungsverfahren |
| JP57029116A JPS57156471A (en) | 1981-02-26 | 1982-02-26 | Heterocyclic alcohols, functional derivatives and manufacture |
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2500452A1 true FR2500452A1 (fr) | 1982-08-27 |
| FR2500452B1 FR2500452B1 (US20020128544A1-20020912-P00008.png) | 1983-07-18 |
Family
ID=9255649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8103830A Granted FR2500452A1 (fr) | 1981-02-26 | 1981-02-26 | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation |
Country Status (11)
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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2242094A1 (US20020128544A1-20020912-P00008.png) * | 1973-08-29 | 1975-03-28 | Roussel Uclaf | |
| FR2248835A1 (US20020128544A1-20020912-P00008.png) * | 1973-10-24 | 1975-05-23 | Shionogi & Co | |
| FR2298329A2 (fr) * | 1975-01-22 | 1976-08-20 | Roussel Uclaf | Nouv |
| EP0027913A2 (de) * | 1979-10-26 | 1981-05-06 | Ciba-Geigy Ag | Druckempfindliches oder wärmeempfindliches Aufzeichnungsmaterial |
Family Cites Families (4)
| 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 (US20020128544A1-20020912-P00008.png) * | 1965-10-07 | |||
| US3573317A (en) * | 1968-08-12 | 1971-03-30 | Olin Corp | 3-trichloromethyl-5-substituted-1,2,4-thiadiazoles |
| DE2719561A1 (de) * | 1976-05-05 | 1977-11-17 | Ciba Geigy Ag | Chrysanthemumsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel |
-
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 BE BE0/207419A patent/BE892287A/fr not_active IP Right Cessation
- 1982-02-25 AU AU80784/82A patent/AU546363B1/en not_active Ceased
- 1982-02-25 GB GB8205541A patent/GB2093840B/en not_active Expired
- 1982-02-25 IT IT47869/82A patent/IT1147646B/it active
- 1982-02-25 CH CH1157/82A patent/CH653329A5/fr not_active IP Right Cessation
- 1982-02-25 HU HU82582A patent/HU191345B/hu unknown
- 1982-02-25 US US06/352,256 patent/US4501894A/en not_active Expired - Fee Related
- 1982-02-26 DE DE19823207043 patent/DE3207043A1/de not_active Withdrawn
- 1982-02-26 JP JP57029116A patent/JPS57156471A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2242094A1 (US20020128544A1-20020912-P00008.png) * | 1973-08-29 | 1975-03-28 | Roussel Uclaf | |
| FR2248835A1 (US20020128544A1-20020912-P00008.png) * | 1973-10-24 | 1975-05-23 | Shionogi & Co | |
| FR2298329A2 (fr) * | 1975-01-22 | 1976-08-20 | Roussel Uclaf | Nouv |
| EP0027913A2 (de) * | 1979-10-26 | 1981-05-06 | Ciba-Geigy Ag | Druckempfindliches oder wärmeempfindliches Aufzeichnungsmaterial |
Also Published As
| Publication number | Publication date |
|---|---|
| AU546363B1 (en) | 1985-08-29 |
| BE892287A (fr) | 1982-08-25 |
| IT8247869A0 (it) | 1982-02-25 |
| US4501894A (en) | 1985-02-26 |
| FR2500452B1 (US20020128544A1-20020912-P00008.png) | 1983-07-18 |
| JPS57156471A (en) | 1982-09-27 |
| GB2093840A (en) | 1982-09-08 |
| NL8200704A (nl) | 1982-09-16 |
| GB2093840B (en) | 1985-02-27 |
| HU191345B (en) | 1987-02-27 |
| DE3207043A1 (de) | 1982-09-16 |
| IT1147646B (it) | 1986-11-19 |
| CH653329A5 (fr) | 1985-12-31 |
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Legal Events
| Date | Code | Title | Description |
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| ST | Notification of lapse |