PH26457A - Process for the preparation of insecticidally active diphenyl ether compounds - Google Patents

Process for the preparation of insecticidally active diphenyl ether compounds Download PDF

Info

Publication number: PH26457A
Authority: PH; Philippines
Prior art keywords: formula; compound; phenoxyphenyl; hydrogen; fluoro
Prior art date: 1987-02-17

Application number

PH36454A

Other languages

English (en)

Inventor

Michael John Bushell

Ralph Alexander Raphael

Original Assignee

Ici Plc

Priority date (The priority date 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 date listed.)

1987-02-17

Filing date

1988-02-03

Publication date

1992-07-27

1988-02-03 Application filed by Ici Plc filed Critical Ici Plc

1992-07-27 Publication of PH26457A publication Critical patent/PH26457A/en

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)

PH36454A 1987-02-17 1988-02-03 Process for the preparation of insecticidally active diphenyl ether compounds PH26457A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Publication	Publication Date	Title
Buss et al.	1985	The stereocontrolled Horner-Wittig reaction: synthesis of disubstituted alkenes
Burton et al.	1996	Fluorinated ylides and related compounds
Begue et al.	1992	The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones
US6924389B2 (en)	2005-08-02	Method for producing diphosphines and the use thereof
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US4942264A (en)	1990-07-17	Process for the preparation of insecticidally active diphenylether compounds
JP2002512593A (ja)	2002-04-23	重合可能なビアリール、それらの調製方法及び使用
AU607127B2 (en)	1991-02-28	Insecticidally active, fluorinated phenylalkane and phenylalkene derivatives
WO1992015544A1 (en)	1992-09-17	Method of making 2,7-dimethyl-2,4,6-octatrienedial and derivatives thereof
Vinson et al.	1983	Synthesis of carbon and phosphorus esters of. alpha.-fluoro alcohols
WO2011110091A1 (zh)	2011-09-15	番茄红素中间体1，3，6，10-四双键十五碳膦酸酯及其制备方法和应用
RU2184108C2 (ru)	2002-06-27	Способ получения фторолефиновых гербицидов и промежуточные соединения
Delapierre et al.	2000	Enantioselective Conjugate Addition of Diethylzinc to Enones with Chiral Copper‐QUIPHOS Catalyst Influence of the Addition of Water on the Enantioselectivity
GB2234509A (en)	1991-02-06	Intermediates for the preparation of insecticidally active compounds
Guedira et al.	1992	Ambident behavior of ketone enolate anions in SNAr substitutions on fluorobenzonitrile substrates
US6159956A (en)	2000-12-12	Process and intermediate compounds for the preparation of difluorovinylsilane insecticidal and acaricidal agents
EP0805133B1 (de)	1998-10-07	Verfahren zur Substitution von Cyclopentadien
JP2004352724A (ja)	2004-12-16	フェニルアルキレンカルボン酸誘導体の製造方法
Bencivengo et al.	1981	Nonprotic procedure for transesterification of methyl esters
US6232516B1 (en)	2001-05-15	Process for cyclopentadiene substitution
EP0007142B1 (de)	1982-05-12	Zwischenprodukte zur Herstellung von Cyclopropancarbonsäureestern und Verfahren zu ihrer Herstellung
US6207846B1 (en)	2001-03-27	Process and intermediate compounds for the preparation of difluorovinylsilane insecticidal and acaricidal agents
US4966987A (en)	1990-10-30	Fluoro-containing 1-arylalkoxytris(dialkylamino)phosphonium salt, a process for their preparation and their use
Keller	1998	Catalytic enantioselective conjugate addition reactions: with a focus on water