JPS5910677B2 - リン酸エステルハライドおよびその製造法 - Google Patents
リン酸エステルハライドおよびその製造法Info
- Publication number
- JPS5910677B2 JPS5910677B2 JP51017191A JP1719176A JPS5910677B2 JP S5910677 B2 JPS5910677 B2 JP S5910677B2 JP 51017191 A JP51017191 A JP 51017191A JP 1719176 A JP1719176 A JP 1719176A JP S5910677 B2 JPS5910677 B2 JP S5910677B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ester
- phosphoric acid
- halogen
- chlorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Phosphate ester halide Chemical class 0.000 title description 32
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229910019142 PO4 Inorganic materials 0.000 title description 3
- 239000010452 phosphate Substances 0.000 title description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 description 29
- 229910052801 chlorine Inorganic materials 0.000 description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 15
- 150000001336 alkenes Chemical class 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 13
- 238000009835 boiling Methods 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 8
- 230000002140 halogenating effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- KNLUSLUJCULKTE-UHFFFAOYSA-N propyl dihydrogen phosphate;dihydrochloride Chemical compound Cl.Cl.CCCOP(O)(O)=O KNLUSLUJCULKTE-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100496114 Caenorhabditis elegans clc-2 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- BHCNNWHXJDOTPE-UHFFFAOYSA-N (3,3,4,4-tetrafluorocyclobuten-1-yl)benzene Chemical compound FC1(F)C(F)(F)C=C1C1=CC=CC=C1 BHCNNWHXJDOTPE-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 1
- OZCRKDNRAAKDAN-HNQUOIGGSA-N (e)-but-1-ene-1,4-diol Chemical compound OCC\C=C\O OZCRKDNRAAKDAN-HNQUOIGGSA-N 0.000 description 1
- VOGHDWQJCXXBMH-RQOWECAXSA-N (z)-1,2-dichlorobut-2-ene Chemical compound C\C=C(/Cl)CCl VOGHDWQJCXXBMH-RQOWECAXSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
- MUDYCSPLOKOTRJ-UHFFFAOYSA-N 1-chloropropa-1,2-diene Chemical compound ClC=C=C MUDYCSPLOKOTRJ-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 1
- KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical group FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 description 1
- UKQJZQQPMIFNHE-UHFFFAOYSA-N 2-isocyanatoprop-1-ene Chemical compound CC(=C)N=C=O UKQJZQQPMIFNHE-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- FAYFWMOSHFCQPG-UHFFFAOYSA-N 3-Methyl sulfolene Chemical compound CC1=CCS(=O)(=O)C1 FAYFWMOSHFCQPG-UHFFFAOYSA-N 0.000 description 1
- MHMUCYJKZUZMNJ-UHFFFAOYSA-N 3-chloroacrylic acid Chemical compound OC(=O)C=CCl MHMUCYJKZUZMNJ-UHFFFAOYSA-N 0.000 description 1
- LNGQLHZIYFQUIR-UHFFFAOYSA-N 3-chlorocyclohexene Chemical compound ClC1CCCC=C1 LNGQLHZIYFQUIR-UHFFFAOYSA-N 0.000 description 1
- LXJDXBGQVSHLOJ-UHFFFAOYSA-N 3-isocyanoprop-1-ene Chemical compound C=CC[N+]#[C-] LXJDXBGQVSHLOJ-UHFFFAOYSA-N 0.000 description 1
- QVGKEZQXVLUDED-UHFFFAOYSA-N 4-chloro-1-isocyanatobut-1-ene Chemical compound ClCCC=CN=C=O QVGKEZQXVLUDED-UHFFFAOYSA-N 0.000 description 1
- AAMIYSNERSMTFE-UHFFFAOYSA-N 4-chloro-1-isocyanobut-1-ene Chemical compound ClCCC=C[N+]#[C-] AAMIYSNERSMTFE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- XKZJIDFRFYQNMX-UHFFFAOYSA-N COP(O)(OC)=O.F Chemical compound COP(O)(OC)=O.F XKZJIDFRFYQNMX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- TZWVUUJCEAZKPK-UHFFFAOYSA-N Cl.COP(=O)OC Chemical compound Cl.COP(=O)OC TZWVUUJCEAZKPK-UHFFFAOYSA-N 0.000 description 1
- AXWYWVKDJKQDBR-UHFFFAOYSA-N Cl.COP(C)(O)=O Chemical compound Cl.COP(C)(O)=O AXWYWVKDJKQDBR-UHFFFAOYSA-N 0.000 description 1
- MWLOLDRBELJKDK-UHFFFAOYSA-N Cl.COP(O)(=O)C1=CC=CC=C1 Chemical compound Cl.COP(O)(=O)C1=CC=CC=C1 MWLOLDRBELJKDK-UHFFFAOYSA-N 0.000 description 1
- KGWOWBJZJMKPKQ-UHFFFAOYSA-N Cl.Cl.CC(C)OP(O)(O)=O Chemical compound Cl.Cl.CC(C)OP(O)(O)=O KGWOWBJZJMKPKQ-UHFFFAOYSA-N 0.000 description 1
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical group COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WIQHNEPWZZQSDK-UHFFFAOYSA-N F.F.CCOP(O)(O)=O Chemical compound F.F.CCOP(O)(O)=O WIQHNEPWZZQSDK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- DFNOZMSCNCSJIP-UHFFFAOYSA-N OP(O)(OC(CCl)F)=O.Cl.Cl Chemical compound OP(O)(OC(CCl)F)=O.Cl.Cl DFNOZMSCNCSJIP-UHFFFAOYSA-N 0.000 description 1
- WEPRHPXRNFQBSY-UHFFFAOYSA-N OP(OC(CCl)Cl)(OC(CCl)Cl)=O.Cl Chemical compound OP(OC(CCl)Cl)(OC(CCl)Cl)=O.Cl WEPRHPXRNFQBSY-UHFFFAOYSA-N 0.000 description 1
- XXHJFACWDVECEX-UHFFFAOYSA-N OP(OC(CCl)F)(OC(CCl)F)=O.Cl Chemical compound OP(OC(CCl)F)(OC(CCl)F)=O.Cl XXHJFACWDVECEX-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- XAJHYPAQCYNPIV-UHFFFAOYSA-N but-3-ene-1,3-diol Chemical compound OCCC(O)=C XAJHYPAQCYNPIV-UHFFFAOYSA-N 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- YVWBQGFBSVLPIK-UHFFFAOYSA-N cyclohex-2-ene-1-carboxylic acid Chemical compound OC(=O)C1CCCC=C1 YVWBQGFBSVLPIK-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- ONXOMWCDSXXELR-UHFFFAOYSA-N dibutyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCCCOP(O)(=O)OCCCC ONXOMWCDSXXELR-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SNVCRNWSNUUGEA-UHFFFAOYSA-N dichlorophosphoryloxymethane Chemical compound COP(Cl)(Cl)=O SNVCRNWSNUUGEA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- NBMUEQRPPMFTJL-UHFFFAOYSA-N diethyl hydrogen phosphate hydrobromide Chemical compound Br.CCOP(O)(=O)OCC NBMUEQRPPMFTJL-UHFFFAOYSA-N 0.000 description 1
- YBBUMZUSUMRUKT-UHFFFAOYSA-N dimethyl hydrogen phosphate hydrochloride Chemical compound Cl.COP(O)(=O)OC YBBUMZUSUMRUKT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CBWXWSRHBSRSMA-UHFFFAOYSA-N ethoxy(ethyl)phosphinic acid hydrochloride Chemical compound Cl.CCOP(O)(=O)CC CBWXWSRHBSRSMA-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- BZAAYLBSHWLBGS-UHFFFAOYSA-N ethyl dihydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(O)=O BZAAYLBSHWLBGS-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XUJBUAFHPKSYHS-UHFFFAOYSA-N methyl dihydrogen phosphate;dihydrochloride Chemical compound Cl.Cl.COP(O)(O)=O XUJBUAFHPKSYHS-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2507779A DE2507779C2 (de) | 1975-02-22 | 1975-02-22 | Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51110521A JPS51110521A (es) | 1976-09-30 |
| JPS5910677B2 true JPS5910677B2 (ja) | 1984-03-10 |
Family
ID=5939608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51017191A Expired JPS5910677B2 (ja) | 1975-02-22 | 1976-02-20 | リン酸エステルハライドおよびその製造法 |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5910677B2 (es) |
| AT (1) | AT341543B (es) |
| BE (1) | BE838737A (es) |
| BR (1) | BR7601096A (es) |
| CA (1) | CA1072574A (es) |
| CH (1) | CH623058A5 (es) |
| CS (1) | CS181696B2 (es) |
| DD (1) | DD125577A5 (es) |
| DE (1) | DE2507779C2 (es) |
| DK (1) | DK141936C (es) |
| ES (1) | ES445370A1 (es) |
| FR (1) | FR2301531A1 (es) |
| GB (1) | GB1513341A (es) |
| HU (1) | HU175203B (es) |
| IL (1) | IL49077A (es) |
| IT (1) | IT1053874B (es) |
| LU (1) | LU74395A1 (es) |
| NL (1) | NL187355C (es) |
| PL (1) | PL99859B1 (es) |
| RO (1) | RO68979A (es) |
| SU (1) | SU604499A3 (es) |
| ZA (1) | ZA761006B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2630561A1 (de) * | 1976-07-07 | 1978-01-19 | Bayer Ag | 1-fluor-2-halogen-aethyl-thionophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL30533A (en) * | 1967-09-01 | 1972-01-27 | Bayer Ag | Thiol-or thionothiol-phosphoric or-phosphonic acid esters |
| DE2417143C2 (de) * | 1974-04-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
-
1975
- 1975-02-22 DE DE2507779A patent/DE2507779C2/de not_active Expired
-
1976
- 1976-01-21 HU HU76BA3358A patent/HU175203B/hu unknown
- 1976-02-18 CH CH200576A patent/CH623058A5/de not_active IP Right Cessation
- 1976-02-19 NL NLAANVRAGE7601697,A patent/NL187355C/xx not_active IP Right Cessation
- 1976-02-19 RO RO7684853A patent/RO68979A/ro unknown
- 1976-02-20 FR FR7604795A patent/FR2301531A1/fr active Granted
- 1976-02-20 ZA ZA761006A patent/ZA761006B/xx unknown
- 1976-02-20 CA CA246,203A patent/CA1072574A/en not_active Expired
- 1976-02-20 GB GB6791/76A patent/GB1513341A/en not_active Expired
- 1976-02-20 DK DK70576A patent/DK141936C/da not_active IP Right Cessation
- 1976-02-20 CS CS7600001144A patent/CS181696B2/cs unknown
- 1976-02-20 BR BR7601096A patent/BR7601096A/pt unknown
- 1976-02-20 PL PL1976187346A patent/PL99859B1/pl unknown
- 1976-02-20 IL IL7649077A patent/IL49077A/xx unknown
- 1976-02-20 AT AT122076A patent/AT341543B/de not_active IP Right Cessation
- 1976-02-20 IT IT48195/76A patent/IT1053874B/it active
- 1976-02-20 JP JP51017191A patent/JPS5910677B2/ja not_active Expired
- 1976-02-20 ES ES445370A patent/ES445370A1/es not_active Expired
- 1976-02-20 DD DD191380A patent/DD125577A5/xx unknown
- 1976-02-20 LU LU74395A patent/LU74395A1/xx unknown
- 1976-02-20 SU SU762325907A patent/SU604499A3/ru active
- 1976-02-20 BE BE2054842A patent/BE838737A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| LU74395A1 (es) | 1977-01-06 |
| IT1053874B (it) | 1981-10-10 |
| DE2507779C2 (de) | 1982-07-01 |
| NL187355C (nl) | 1991-09-02 |
| HU175203B (hu) | 1980-06-28 |
| CH623058A5 (en) | 1981-05-15 |
| PL99859B1 (pl) | 1978-08-31 |
| DK141936C (da) | 1980-12-01 |
| DD125577A5 (es) | 1977-05-04 |
| NL187355B (nl) | 1991-04-02 |
| DK70576A (da) | 1976-08-23 |
| JPS51110521A (es) | 1976-09-30 |
| ES445370A1 (es) | 1977-07-01 |
| FR2301531B1 (es) | 1980-11-21 |
| DE2507779A1 (de) | 1976-09-02 |
| IL49077A (en) | 1979-07-25 |
| CA1072574A (en) | 1980-02-26 |
| SU604499A3 (ru) | 1978-04-25 |
| AT341543B (de) | 1978-02-10 |
| IL49077A0 (en) | 1976-04-30 |
| DK141936B (da) | 1980-07-21 |
| CS181696B2 (en) | 1978-03-31 |
| RO68979A (ro) | 1981-05-30 |
| BR7601096A (pt) | 1976-09-14 |
| ZA761006B (en) | 1977-02-23 |
| BE838737A (fr) | 1976-08-20 |
| ATA122076A (de) | 1977-06-15 |
| FR2301531A1 (fr) | 1976-09-17 |
| GB1513341A (en) | 1978-06-07 |
| NL7601697A (nl) | 1976-08-24 |
| AU1130776A (en) | 1977-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2690450A (en) | Method for preparation of sulfur-containing esters of phosphoric acid | |
| US2891059A (en) | Thiophosphoric acid esters and their production | |
| IL29899A (en) | Wealthy ester of acid 2,2- dichloro vinylphosphoric | |
| DE2417143C2 (de) | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern | |
| US3003916A (en) | Vinyl phosphate insecticides | |
| JPS5910677B2 (ja) | リン酸エステルハライドおよびその製造法 | |
| US3180890A (en) | Imino-halo compounds and process for their production | |
| US3200146A (en) | Tetrahaloethylsulfenyl halide | |
| US4182733A (en) | Process for preparing phosphoric acid esterhalides | |
| US7435841B2 (en) | Preparation of halohydrocarbyl phosphonic acid diesters | |
| US2867564A (en) | Halogenated bicycl oheptenyl sulfite derivatives | |
| US4138452A (en) | Process for preparing phosphoric acid esterhalides | |
| US3219680A (en) | Thiolfluoroformates and method for their preparation | |
| Haubein | New organophosphorus derivatives of p-thioxane and 2, 6-dimethyl-p-thioxane with insecticidal and acaricidal activity | |
| US3081329A (en) | S-halo-o-hydrocarbon phosphorochloridothiolates | |
| US3035082A (en) | Disulfides of the phosphoric, phosphonic and phosphinic acid series and process for the production thereof | |
| US3299190A (en) | Omicron, omicron-dialkyl-omicron-dichlorovinyl phosphates | |
| US3166581A (en) | S-acyloxyalkyl and s-acyloxyalkenyl esters of o, o-diorgano-phosphorothiolic acids | |
| US4003939A (en) | Addition of sulfenyl halides to olefins and acetylenes | |
| NO148473B (no) | Middel til aa drepe midder og deres egg og anvendelse av middelet. | |
| US3184465A (en) | Alkenyl thionophosphonic acid fluoramides | |
| US4112024A (en) | Phosphoryl sulfenyl chloride olefin adducts | |
| EP0107163B1 (de) | Dihalogenvinylphenyl-phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| IL25831A (en) | Nematocidal compositions containing esters of o-ethyl-s,s-dipropyl-dithiolphosphoric acid | |
| US2776988A (en) | Esters of alpha-dichloromethyl benzhydrols and process |