PH26457A - Process for the preparation of insecticidally active diphenyl ether compounds - Google Patents
Process for the preparation of insecticidally active diphenyl ether compounds Download PDFInfo
- Publication number
- PH26457A PH26457A PH36454A PH36454A PH26457A PH 26457 A PH26457 A PH 26457A PH 36454 A PH36454 A PH 36454A PH 36454 A PH36454 A PH 36454A PH 26457 A PH26457 A PH 26457A
- Authority
- PH
- Philippines
- Prior art keywords
- formula
- compound
- phenoxyphenyl
- hydrogen
- fluoro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 150000001993 dienes Chemical class 0.000 claims abstract description 6
- 238000007239 Wittig reaction Methods 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 halide anion Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000004714 phosphonium salts Chemical class 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- FTLCSCOMAQFCHL-BACBYAOASA-M [(e)-3-(3-phenoxyphenyl)prop-2-enyl]-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C(C=1)=CC=CC=1OC1=CC=CC=C1 FTLCSCOMAQFCHL-BACBYAOASA-M 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- UEEXSKUQFMMNML-IERUDJENSA-M [(e)-3-(4-fluoro-3-phenoxyphenyl)prop-2-enyl]-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(OC=2C=CC=CC=2)C(F)=CC=C1\C=C\C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UEEXSKUQFMMNML-IERUDJENSA-M 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003003 phosphines Chemical class 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- UZRFBWDHVIEVAQ-FNORWQNLSA-N 1-[(e)-3-bromoprop-1-enyl]-3-phenoxybenzene Chemical compound BrC\C=C\C1=CC=CC(OC=2C=CC=CC=2)=C1 UZRFBWDHVIEVAQ-FNORWQNLSA-N 0.000 claims description 3
- DTMXOLQBAQULLC-SNAWJCMRSA-N 4-[(e)-3-chloroprop-1-enyl]-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(\C=C\CCl)C=C1OC1=CC=CC=C1 DTMXOLQBAQULLC-SNAWJCMRSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 3
- CFEIUJYRYSRJJF-DUXPYHPUSA-N 1-chloro-4-[3-[(e)-3-chloroprop-1-enyl]phenoxy]benzene Chemical compound ClC\C=C\C1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 CFEIUJYRYSRJJF-DUXPYHPUSA-N 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004794 vinyl magnesium halides Chemical class 0.000 claims description 2
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical group [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 35
- 239000000203 mixture Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 150000001793 charged compounds Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- XSFFZLMYUGMVBS-UHFFFAOYSA-N 4-[5-chloro-5,5-difluoro-4-[4-(trifluoromethoxy)phenyl]penta-1,3-dienyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1C=CC=C(C(F)(F)Cl)C1=CC=C(OC(F)(F)F)C=C1 XSFFZLMYUGMVBS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BFXRXGRUCURCGC-FNORWQNLSA-N 1-[(e)-3-chloroprop-1-enyl]-3-phenoxybenzene Chemical compound ClC\C=C\C1=CC=CC(OC=2C=CC=CC=2)=C1 BFXRXGRUCURCGC-FNORWQNLSA-N 0.000 description 3
- FTLCSCOMAQFCHL-UHFFFAOYSA-M 3-(3-phenoxyphenyl)prop-2-enyl-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC=CC(C=1)=CC=CC=1OC1=CC=CC=C1 FTLCSCOMAQFCHL-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KJZKHJGMDINZHI-UHFFFAOYSA-N 1-(3-phenoxyphenyl)prop-2-en-1-ol Chemical compound C=CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 KJZKHJGMDINZHI-UHFFFAOYSA-N 0.000 description 2
- NUBWJTCIWOUPAY-UHFFFAOYSA-N 1-[1,1-difluoro-5-(3-phenoxyphenyl)penta-2,4-dien-2-yl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)F)=CC=CC1=CC=CC(OC=2C=CC=CC=2)=C1 NUBWJTCIWOUPAY-UHFFFAOYSA-N 0.000 description 2
- LGHAOPKAYGCSCS-UHFFFAOYSA-N 1-[1,1-difluoro-5-(3-phenoxyphenyl)pentan-2-yl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)F)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 LGHAOPKAYGCSCS-UHFFFAOYSA-N 0.000 description 2
- NZTDDZUMHYFRGR-UHFFFAOYSA-N 1-fluoro-2-phenoxy-4-[5,5,5-trifluoro-4-[4-(trifluoromethoxy)phenyl]penta-1,3-dienyl]benzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1C=CC=C(C(F)(F)F)C1=CC=C(OC(F)(F)F)C=C1 NZTDDZUMHYFRGR-UHFFFAOYSA-N 0.000 description 2
- QRPFSGBBSUBSQP-UHFFFAOYSA-N 1-phenoxy-3-[5,5,5-trifluoro-4-[4-(trifluoromethoxy)phenyl]penta-1,3-dienyl]benzene Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C(F)(F)F)=CC=CC1=CC=CC(OC=2C=CC=CC=2)=C1 QRPFSGBBSUBSQP-UHFFFAOYSA-N 0.000 description 2
- RTONLFPQGZSPLG-UHFFFAOYSA-N 1-phenoxy-3-[5,5,5-trifluoro-4-[4-(trifluoromethoxy)phenyl]pentyl]benzene Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C(F)(F)F)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 RTONLFPQGZSPLG-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- GFIWENSXVCDTKC-BNSHTTSQSA-M [(e)-3-[3-(4-chlorophenoxy)phenyl]prop-2-enyl]-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1OC1=CC=CC(\C=C\C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GFIWENSXVCDTKC-BNSHTTSQSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 2
- TYTAQHBVMKOWHI-UHFFFAOYSA-N 1-[1,1-difluoro-5-(3-phenoxyphenyl)penta-2,4-dien-2-yl]-4-(trifluoromethoxy)benzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(F)F)=CC=CC(C=1)=CC=CC=1OC1=CC=CC=C1 TYTAQHBVMKOWHI-UHFFFAOYSA-N 0.000 description 1
- BXFHQTIFPVRTQU-UHFFFAOYSA-N 1-[1,1-difluoro-5-(3-phenoxyphenyl)pentan-2-yl]-4-(trifluoromethoxy)benzene Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(F)F)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 BXFHQTIFPVRTQU-UHFFFAOYSA-N 0.000 description 1
- UIRVESRQSAPKOO-UHFFFAOYSA-N 1-[1-chloro-1,1-difluoro-5-(3-phenoxyphenyl)penta-2,4-dien-2-yl]-4-(trifluoromethoxy)benzene Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C(F)(F)Cl)=CC=CC1=CC=CC(OC=2C=CC=CC=2)=C1 UIRVESRQSAPKOO-UHFFFAOYSA-N 0.000 description 1
- MIFKZMITESRWAB-UHFFFAOYSA-N 1-[1-chloro-1,1-difluoro-5-(3-phenoxyphenyl)penta-2,4-dien-2-yl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)Cl)=CC=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MIFKZMITESRWAB-UHFFFAOYSA-N 0.000 description 1
- SAZPNBMLLIUGAK-UHFFFAOYSA-N 1-[1-chloro-1,1-difluoro-5-(3-phenoxyphenyl)pentan-2-yl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)Cl)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 SAZPNBMLLIUGAK-UHFFFAOYSA-N 0.000 description 1
- OZVMTGZZXACPAV-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)phenyl]prop-2-en-1-ol Chemical compound C=CC(O)C1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 OZVMTGZZXACPAV-UHFFFAOYSA-N 0.000 description 1
- IEXQWUOBLHIYFV-UHFFFAOYSA-N 1-chloro-4-[3-[5,5,5-trifluoro-4-[4-(trifluoromethoxy)phenyl]pentyl]phenoxy]benzene Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(C(F)(F)F)CCCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 IEXQWUOBLHIYFV-UHFFFAOYSA-N 0.000 description 1
- TYNZKFRDFCQCCH-UHFFFAOYSA-N 1-fluoro-2-phenoxy-4-[5,5,5-trifluoro-4-[4-(trifluoromethoxy)phenyl]pentyl]benzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CCCC(C(F)(F)F)C1=CC=C(OC(F)(F)F)C=C1 TYNZKFRDFCQCCH-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- UEEXSKUQFMMNML-UHFFFAOYSA-M 3-(4-fluoro-3-phenoxyphenyl)prop-2-enyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(OC=2C=CC=CC=2)C(F)=CC=C1C=CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UEEXSKUQFMMNML-UHFFFAOYSA-M 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GFIWENSXVCDTKC-UHFFFAOYSA-M [Cl-].C1=CC(Cl)=CC=C1OC1=CC=CC(C=CC[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 Chemical compound [Cl-].C1=CC(Cl)=CC=C1OC1=CC=CC(C=CC[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GFIWENSXVCDTKC-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006042 reductive dechlorination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878703653A GB8703653D0 (en) | 1987-02-17 | 1987-02-17 | Preparation of insecticidally active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26457A true PH26457A (en) | 1992-07-27 |
Family
ID=10612439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH36454A PH26457A (en) | 1987-02-17 | 1988-02-03 | Process for the preparation of insecticidally active diphenyl ether compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4942264A (de) |
| EP (1) | EP0279531B1 (de) |
| JP (1) | JPS63203641A (de) |
| KR (1) | KR880009892A (de) |
| CN (1) | CN1013857B (de) |
| AT (1) | ATE86598T1 (de) |
| AU (1) | AU604833B2 (de) |
| BR (1) | BR8800613A (de) |
| DE (1) | DE3878943T2 (de) |
| GB (2) | GB8703653D0 (de) |
| MY (1) | MY103195A (de) |
| NZ (1) | NZ223405A (de) |
| PH (1) | PH26457A (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8605281D0 (en) * | 1986-03-04 | 1986-04-09 | Ici Plc | Diphenyl ether derivatives |
| GB8703653D0 (en) * | 1987-02-17 | 1987-03-25 | Ici Plc | Preparation of insecticidally active compounds |
| GB2234509B (en) * | 1987-02-17 | 1991-07-31 | Ici Plc | Diphenyl ether intermediates for the preparation of insecticidally active compounds |
| GB8822792D0 (en) * | 1988-09-28 | 1988-11-02 | Ici Plc | Insecticidal compounds |
| IL107161A0 (en) * | 1992-10-15 | 1993-12-28 | Schering Ag | Process for the preparation of 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentane derivatives and intermediates for use in the preparation thereof |
| DE4318370C1 (de) * | 1993-05-28 | 1994-05-11 | Schering Ag | Verfahren und Zwischenprodukte zur Herstellung von substituierten 2-Phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluorpentanen |
| TR27159A (tr) * | 1993-11-12 | 1994-11-10 | Schering Ag | Sübstitüe edilmis 2 -fenil-5-(3-fenoksifelin (1,1,1-trifloropentanlari hazirlamaya mahsus yöntem ve aramaddeler. |
| EP1879454A1 (de) * | 2005-05-07 | 2008-01-23 | Merial Ltd. | Pestizide substituierte phenylether |
| US7374135B2 (en) * | 2006-04-13 | 2008-05-20 | Melanie J. N. Romero | Method and apparatus for collecting yard debris |
| CN113683509B (zh) * | 2021-10-27 | 2022-01-04 | 南京农业大学 | 一种二苯醚酯类化合物及其应用和农药杀菌剂 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58201737A (ja) * | 1982-05-18 | 1983-11-24 | Mitsui Toatsu Chem Inc | 新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
| DE3505370A1 (de) * | 1985-02-14 | 1986-08-14 | Schering AG, 1000 Berlin und 4709 Bergkamen | Aromatische alkanderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| GB8605281D0 (en) * | 1986-03-04 | 1986-04-09 | Ici Plc | Diphenyl ether derivatives |
| GB2187452A (en) * | 1986-03-04 | 1987-09-09 | Ici Plc | Insecticidal fluoroalkyl benzene derivatives |
| FI874121A7 (fi) * | 1986-09-24 | 1988-03-25 | Sumitomo Chemical Co | Heterocykliska foereningar, och deras framstaellning och anvaendning. |
| GB8703653D0 (en) * | 1987-02-17 | 1987-03-25 | Ici Plc | Preparation of insecticidally active compounds |
-
1987
- 1987-02-17 GB GB878703653A patent/GB8703653D0/en active Pending
-
1988
- 1988-01-27 GB GB8801829A patent/GB2201957B/en not_active Expired - Lifetime
- 1988-01-27 AT AT88300669T patent/ATE86598T1/de active
- 1988-01-27 EP EP88300669A patent/EP0279531B1/de not_active Expired - Lifetime
- 1988-01-27 DE DE8888300669T patent/DE3878943T2/de not_active Expired - Fee Related
- 1988-02-03 PH PH36454A patent/PH26457A/en unknown
- 1988-02-04 NZ NZ223405A patent/NZ223405A/xx unknown
- 1988-02-05 AU AU11334/88A patent/AU604833B2/en not_active Ceased
- 1988-02-05 MY MYPI88000115A patent/MY103195A/en unknown
- 1988-02-12 US US07/158,232 patent/US4942264A/en not_active Expired - Fee Related
- 1988-02-12 BR BR8800613A patent/BR8800613A/pt unknown
- 1988-02-15 CN CN88100991A patent/CN1013857B/zh not_active Expired
- 1988-02-17 JP JP63034948A patent/JPS63203641A/ja active Pending
- 1988-02-17 KR KR1019880001684A patent/KR880009892A/ko not_active Withdrawn
-
1989
- 1989-11-30 US US07/443,369 patent/US5081273A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR8800613A (pt) | 1988-09-27 |
| US5081273A (en) | 1992-01-14 |
| ATE86598T1 (de) | 1993-03-15 |
| GB8703653D0 (en) | 1987-03-25 |
| MY103195A (en) | 1993-05-29 |
| KR880009892A (ko) | 1988-10-05 |
| GB8801829D0 (en) | 1988-02-24 |
| GB2201957B (en) | 1991-07-03 |
| AU604833B2 (en) | 1991-01-03 |
| AU1133488A (en) | 1988-08-18 |
| EP0279531A3 (en) | 1990-02-07 |
| EP0279531B1 (de) | 1993-03-10 |
| DE3878943D1 (de) | 1993-04-15 |
| DE3878943T2 (de) | 1993-07-01 |
| EP0279531A2 (de) | 1988-08-24 |
| CN88100991A (zh) | 1988-08-31 |
| CN1013857B (zh) | 1991-09-11 |
| US4942264A (en) | 1990-07-17 |
| JPS63203641A (ja) | 1988-08-23 |
| GB2201957A (en) | 1988-09-14 |
| NZ223405A (en) | 1990-05-28 |
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