TWI572587B - 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 - Google Patents
丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 Download PDFInfo
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- TWI572587B TWI572587B TW101145232A TW101145232A TWI572587B TW I572587 B TWI572587 B TW I572587B TW 101145232 A TW101145232 A TW 101145232A TW 101145232 A TW101145232 A TW 101145232A TW I572587 B TWI572587 B TW I572587B
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- Prior art keywords
- group
- phenyl
- compound
- formula
- alkyl
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- 238000000034 method Methods 0.000 title claims description 178
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title description 39
- 125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 245
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
- 125000001424 substituent group Chemical group 0.000 claims description 87
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 77
- 150000002367 halogens Chemical class 0.000 claims description 77
- 125000004076 pyridyl group Chemical group 0.000 claims description 76
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 53
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 32
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 29
- 229910052700 potassium Inorganic materials 0.000 claims description 28
- 229910052708 sodium Inorganic materials 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 230000002140 halogenating effect Effects 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 150000003462 sulfoxides Chemical class 0.000 claims description 8
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052788 barium Inorganic materials 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 4
- JNTDLFKBNBKNRI-UHFFFAOYSA-L dichloroantimony Chemical compound Cl[Sb]Cl JNTDLFKBNBKNRI-UHFFFAOYSA-L 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- MAQVJOQDDWLWHS-UHFFFAOYSA-N [P].[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [P].[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 MAQVJOQDDWLWHS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical group ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- 239000000203 mixture Substances 0.000 description 91
- 238000006243 chemical reaction Methods 0.000 description 54
- 239000000460 chlorine Substances 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 50
- 239000011734 sodium Substances 0.000 description 45
- 238000002360 preparation method Methods 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 21
- 238000004821 distillation Methods 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 238000005658 halogenation reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 230000026030 halogenation Effects 0.000 description 14
- 239000000376 reactant Substances 0.000 description 14
- 239000000010 aprotic solvent Substances 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000370 acceptor Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- MYJACJGIRSMGIO-UHFFFAOYSA-N dimethyl 2-(3,5-dichlorophenyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=CC(Cl)=CC(Cl)=C1 MYJACJGIRSMGIO-UHFFFAOYSA-N 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- PEISNPFOKRAAEV-UHFFFAOYSA-L disodium;2-[3-(trifluoromethyl)phenyl]propanedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(C([O-])=O)C1=CC=CC(C(F)(F)F)=C1 PEISNPFOKRAAEV-UHFFFAOYSA-L 0.000 description 5
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- XQRPCXSCASOJDW-UHFFFAOYSA-N dimethyl 2-[3-(trifluoromethyl)phenyl]propanedioate Chemical compound COC(=O)C(C(=O)OC)C1=CC=CC(C(F)(F)F)=C1 XQRPCXSCASOJDW-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- DLAKEJZPXICNSC-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)acetonitrile Chemical compound ClC1=CC(Cl)=CC(CC#N)=C1 DLAKEJZPXICNSC-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
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- AOGBPIWNJUXYKK-UHFFFAOYSA-N CC(C(O)=O)(C1=CC(Cl)=CC(Cl)=C1)C#N Chemical compound CC(C(O)=O)(C1=CC(Cl)=CC(Cl)=C1)C#N AOGBPIWNJUXYKK-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- BDROYLJCVXAINE-UHFFFAOYSA-L dipotassium;2-(3,5-dichlorophenyl)propanedioate Chemical compound [K+].[K+].[O-]C(=O)C(C([O-])=O)C1=CC(Cl)=CC(Cl)=C1 BDROYLJCVXAINE-UHFFFAOYSA-L 0.000 description 2
- RWKMXHMCQLVSRQ-UHFFFAOYSA-L disodium;2-(3,5-dichlorophenyl)propanedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(C([O-])=O)C1=CC(Cl)=CC(Cl)=C1 RWKMXHMCQLVSRQ-UHFFFAOYSA-L 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004995 haloalkylthio group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- VCRMDEZFONERTH-UHFFFAOYSA-L dicesium;dichloride Chemical compound [Cl-].[Cl-].[Cs+].[Cs+] VCRMDEZFONERTH-UHFFFAOYSA-L 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- AXAIHGXEQFPLFL-UHFFFAOYSA-L dichlorobismuth Chemical compound Cl[Bi]Cl AXAIHGXEQFPLFL-UHFFFAOYSA-L 0.000 description 1
- AIHLBNSXDBFHSF-UHFFFAOYSA-L dipotassium;2-[3-(trifluoromethyl)phenyl]propanedioate Chemical compound [K+].[K+].[O-]C(=O)C(C([O-])=O)C1=CC=CC(C(F)(F)F)=C1 AIHLBNSXDBFHSF-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- AXDDJHKBOYNJPY-UHFFFAOYSA-L dipotassium;carboxylato carbonate Chemical compound [K+].[K+].[O-]C(=O)OC([O-])=O AXDDJHKBOYNJPY-UHFFFAOYSA-L 0.000 description 1
- CEALXSHFPPCRNM-UHFFFAOYSA-L disodium;carboxylato carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OC([O-])=O CEALXSHFPPCRNM-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 230000036541 health Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- FQMYXUZNOBYEBJ-UHFFFAOYSA-N methyl 2-(3,5-dichlorophenyl)ethanimidate;hydrochloride Chemical compound Cl.COC(=N)CC1=CC(Cl)=CC(Cl)=C1 FQMYXUZNOBYEBJ-UHFFFAOYSA-N 0.000 description 1
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- VVSSRZAVOQVJHG-UHFFFAOYSA-N n-(3-methylpyridin-2-yl)formamide Chemical compound CC1=CC=CN=C1NC=O VVSSRZAVOQVJHG-UHFFFAOYSA-N 0.000 description 1
- FPKKPPXMUGIKKC-UHFFFAOYSA-N n-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1NCC1=CN=C(Cl)S1 FPKKPPXMUGIKKC-UHFFFAOYSA-N 0.000 description 1
- XLVVEEAVMUODOZ-UHFFFAOYSA-N n-pyridin-2-yl-1-pyrimidin-5-ylmethanimine Chemical compound C=1N=CN=CC=1C=NC1=CC=CC=N1 XLVVEEAVMUODOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/36—Acyl halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
- C07C57/36—Phenymalonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/72—Acyl halides containing six-membered aromatic rings
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| TWI528899B (zh) * | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| IN2015DN00375A (enExample) | 2012-06-21 | 2015-06-12 | Du Pont | |
| CN105254515A (zh) * | 2015-11-13 | 2016-01-20 | 浙江汇能生物股份有限公司 | 一种氯化琥珀胆碱的制备方法 |
| TW201738229A (zh) | 2016-04-26 | 2017-11-01 | 杜邦股份有限公司 | 製備ｎ－［（５－嘧啶基）甲基］－２－吡啶胺之方法 |
| EP3553051A4 (en) * | 2016-12-06 | 2020-04-22 | Nippon Kayaku Kabushiki Kaisha | METHOD FOR PRODUCING 3- (PYRIDYL-2-AMINO) PROPIONITRILE AND ANALOGUE THEREOF |
| JP6916161B2 (ja) * | 2018-02-20 | 2021-08-11 | インディアン オイル コーポレーション リミテッド | ポリオレフィンポリマー用添加剤および熱可塑性組成物 |
| WO2019173173A1 (en) | 2018-03-05 | 2019-09-12 | E. I. Du Pont De Nemours And Company | Process and intermidiates for the preparation of certain mesoionic pesticides |
| CN108373468B (zh) * | 2018-05-18 | 2019-12-17 | 武汉工程大学 | 一种n-2-吡啶-5-嘧啶甲胺的制备方法 |
| CN109020952A (zh) * | 2018-11-01 | 2018-12-18 | 雅本化学股份有限公司 | 一种n-2-吡啶基-5-嘧啶甲胺的制备方法 |
| JP2024541320A (ja) | 2021-11-10 | 2024-11-08 | コルテバ アグリサイエンス エルエルシー | 特定のメソイオン性殺虫剤の調製プロセス |
| JP2025526908A (ja) | 2022-08-18 | 2025-08-15 | コルテバ アグリサイエンス エルエルシー | ある特定のメソイオン性殺有害生物剤の中間体の調製及び単離プロセス |
| CN116003253A (zh) * | 2022-12-31 | 2023-04-25 | 上海试四化学品有限公司 | 一种三氟苯嘧啶中间体2-[3-(三氟甲基)苯基]丙二酸二甲酯的制备方法 |
| CN118359606A (zh) * | 2023-01-19 | 2024-07-19 | 华东理工大学 | 三氟苯嘧啶多晶型及其制备方法 |
| CN116715573B (zh) * | 2023-06-29 | 2025-08-19 | 河北华旭化工有限公司 | 一种2,2-二甲基丁酰氯的合成方法 |
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| US20030153728A1 (en) * | 2001-10-02 | 2003-08-14 | Kolb Hartmuth C. | Modified safe and efficient process for the environmentally friendly synthesis of lmidoesters |
| WO2011017351A2 (en) * | 2009-08-05 | 2011-02-10 | E. I. Du Pont De Nemours And Company | Mixtures of mesoionic pesticides |
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| FR2290412A1 (fr) * | 1974-11-09 | 1976-06-04 | Gema Sa | Procede pour la preparation de chlorures d'acide a partir d'esters silyliques |
| US5358924A (en) | 1991-03-21 | 1994-10-25 | Bayer Aktiengesellschaft | 3-hydroxy-4-aryl-5-oxo-pyrozoline derivatives, compositions and use |
| TR199801990T2 (xx) * | 1996-04-02 | 2000-06-21 | Bayer Aktiengesellschaft | Yeni ikameli fenilketoenoller. |
| DE19649665A1 (de) * | 1996-04-02 | 1997-10-09 | Bayer Ag | Neue substituierte Phenylketoenole |
| US6297400B1 (en) * | 1999-07-02 | 2001-10-02 | The Clorox Company | Synthesis of a tetraamido macrocycle ligand from a novel diamidodiol |
| JP3824483B2 (ja) * | 2000-10-31 | 2006-09-20 | 住友ベークライト株式会社 | 芳香族カルボン酸とその酸塩化物、および合成法 |
| JP4644957B2 (ja) * | 2001-03-09 | 2011-03-09 | 住友ベークライト株式会社 | 芳香族カルボン酸及びその酸塩化物誘導体、並びにそれらの合成法 |
| US7060818B2 (en) * | 2003-02-21 | 2006-06-13 | Carnegie Mellon University | Synthesis of macrocyclic tetraamido compounds and new metal insertion process |
| JP2004292393A (ja) * | 2003-03-27 | 2004-10-21 | Sumitomo Bakelite Co Ltd | 芳香族カルボン酸及びその酸塩化物誘導体の合成法 |
| JP2005187368A (ja) * | 2003-12-25 | 2005-07-14 | Sumitomo Chemical Co Ltd | カルボン酸クロリドの製造方法 |
| CN100402520C (zh) * | 2006-07-28 | 2008-07-16 | 马启明 | 2-取代丙二酸钙盐的制备方法及钙盐的用途 |
| RU2373182C2 (ru) * | 2007-12-19 | 2009-11-20 | Государственное образовательное учреждение высшего профессионального образования "Курский государственный технический университет" (КурскГТУ) | Способ получения малоната и сукцината марганца (ii) |
| TWI401023B (zh) | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| MX2012001651A (es) | 2009-08-05 | 2012-03-16 | Du Pont | Pesticidas mesoionicos. |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| US20120122680A1 (en) | 2009-08-05 | 2012-05-17 | E.I. Du Pont De Nemours And Company | Mesoionic pesticides |
| JP2013518062A (ja) * | 2010-01-28 | 2013-05-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃ型肝炎阻害化合物 |
| TWI528899B (zh) | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) * | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
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2012
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- 2012-12-13 JP JP2014547413A patent/JP2015501841A/ja active Pending
- 2012-12-13 CN CN201280061781.4A patent/CN104066713B/zh active Active
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030153728A1 (en) * | 2001-10-02 | 2003-08-14 | Kolb Hartmuth C. | Modified safe and efficient process for the environmentally friendly synthesis of lmidoesters |
| WO2011017351A2 (en) * | 2009-08-05 | 2011-02-10 | E. I. Du Pont De Nemours And Company | Mixtures of mesoionic pesticides |
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| Title |
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| CAS Registry Number: 1196533-04-6及1196155-85-7 * |
Also Published As
| Publication number | Publication date |
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| JP2018058840A (ja) | 2018-04-12 |
| US9108965B2 (en) | 2015-08-18 |
| KR20140107420A (ko) | 2014-09-04 |
| JP6579399B2 (ja) | 2019-09-25 |
| JP2015501841A (ja) | 2015-01-19 |
| ZA201403383B (en) | 2015-12-23 |
| IL232632A (en) | 2017-04-30 |
| IL232632A0 (en) | 2014-06-30 |
| AR089221A1 (es) | 2014-08-06 |
| CO7121339A2 (es) | 2014-11-20 |
| HUE044394T2 (hu) | 2019-10-28 |
| AU2012352256A1 (en) | 2014-05-29 |
| BR112014014232B1 (pt) | 2020-01-28 |
| EP2791107A1 (en) | 2014-10-22 |
| CA2857333A1 (en) | 2013-06-20 |
| KR102066682B1 (ko) | 2020-01-16 |
| AU2012352256B2 (en) | 2017-05-25 |
| RU2636942C2 (ru) | 2017-11-29 |
| BR112014014232A2 (pt) | 2018-05-22 |
| RU2014128826A (ru) | 2016-02-10 |
| WO2013090547A1 (en) | 2013-06-20 |
| US20140343284A1 (en) | 2014-11-20 |
| MX352470B (es) | 2017-11-27 |
| TW201329037A (zh) | 2013-07-16 |
| EP2791107B1 (en) | 2019-03-13 |
| CN104066713B (zh) | 2016-08-24 |
| CN104066713A (zh) | 2014-09-24 |
| MX2014006992A (es) | 2014-08-01 |
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