DK174170B1 - Fremgangsmåde til separation af et enantiomerpar - Google Patents
Fremgangsmåde til separation af et enantiomerpar Download PDFInfo
- Publication number
- DK174170B1 DK174170B1 DK198304626A DK462683A DK174170B1 DK 174170 B1 DK174170 B1 DK 174170B1 DK 198304626 A DK198304626 A DK 198304626A DK 462683 A DK462683 A DK 462683A DK 174170 B1 DK174170 B1 DK 174170B1
- Authority
- DK
- Denmark
- Prior art keywords
- cis
- cyano
- chloro
- phenoxybenzyl
- trifluoroprop
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- 239000013078 crystal Substances 0.000 claims description 27
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 22
- 239000002178 crystalline material Substances 0.000 claims description 15
- -1 prop-1-ene 1-yl Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
- 229940043279 diisopropylamine Drugs 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical class CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 abstract description 5
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 48
- 239000000203 mixture Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YRVIZJAHOHOQGV-UHFFFAOYSA-N 2-[3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropyl]-2-(3-phenoxyphenyl)acetonitrile Chemical compound CC1(C)C(C=C(Cl)C(F)(F)F)C1C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YRVIZJAHOHOQGV-UHFFFAOYSA-N 0.000 description 1
- WQAZXRGPWRCXCW-UNOMPAQXSA-N 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-1-[cyano-(3-phenoxyphenyl)methyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1(C(O)=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 WQAZXRGPWRCXCW-UNOMPAQXSA-N 0.000 description 1
- LJQRTRWRVDBRBB-KCWVNHISSA-N C(C1=CC=CC=C1)OC(=O)[C@@H]1C([C@@H]1\C=C(\C(F)(F)F)/Cl)(C)C Chemical group C(C1=CC=CC=C1)OC(=O)[C@@H]1C([C@@H]1\C=C(\C(F)(F)F)/Cl)(C)C LJQRTRWRVDBRBB-KCWVNHISSA-N 0.000 description 1
- 101100489581 Caenorhabditis elegans par-5 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZXQYGBMAQZUVMI-HQMWCCLBSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] (1s,3s)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-HQMWCCLBSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PKAHQJNJPDVTDP-UHFFFAOYSA-N methyl cyclopropanecarboxylate Chemical compound COC(=O)C1CC1 PKAHQJNJPDVTDP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Pulleys (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8229724 | 1982-10-18 | ||
| GB8229724 | 1982-10-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK462683D0 DK462683D0 (da) | 1983-10-07 |
| DK462683A DK462683A (da) | 1984-04-19 |
| DK174170B1 true DK174170B1 (da) | 2002-08-12 |
Family
ID=10533672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198304626A DK174170B1 (da) | 1982-10-18 | 1983-10-07 | Fremgangsmåde til separation af et enantiomerpar |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4512931A (enExample) |
| EP (1) | EP0107296B1 (enExample) |
| JP (2) | JPS5988454A (enExample) |
| AT (1) | ATE28324T1 (enExample) |
| AU (1) | AU555545B2 (enExample) |
| CA (1) | CA1208656A (enExample) |
| CS (1) | CS251767B2 (enExample) |
| DE (1) | DE3372480D1 (enExample) |
| DK (1) | DK174170B1 (enExample) |
| ES (1) | ES8600222A1 (enExample) |
| GB (1) | GB2128607A (enExample) |
| HU (1) | HU192856B (enExample) |
| IL (1) | IL69775A (enExample) |
| MY (1) | MY100551A (enExample) |
| NZ (1) | NZ205562A (enExample) |
| ZA (1) | ZA836965B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8418331D0 (en) * | 1984-07-18 | 1984-08-22 | Ici Plc | Insecticidal ester |
| GB8422872D0 (en) * | 1984-09-11 | 1984-10-17 | Ici Plc | Insecticidal product |
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| HU198373B (en) * | 1986-01-08 | 1989-10-30 | Chinoin Gyogyszer Es Vegyeszet | Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components |
| DE3522629A1 (de) * | 1985-06-25 | 1987-01-08 | Bayer Ag | Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester |
| US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
| ATE90338T1 (de) * | 1989-01-17 | 1993-06-15 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung von cypermethrinisomeren. |
| US5128497A (en) * | 1990-01-03 | 1992-07-07 | Fmc Corporation | Conversion of pyrethroid isomers to more active species |
| GB9127355D0 (en) * | 1991-12-24 | 1992-02-19 | Ici Plc | Isomerisation process |
| US5711956A (en) * | 1994-12-08 | 1998-01-27 | American Cyanamid Company | Solid insecticidal formulation |
| US6801817B1 (en) * | 2001-02-20 | 2004-10-05 | Advanced Micro Devices, Inc. | Method and apparatus for integrating multiple process controllers |
| GB0118137D0 (en) * | 2001-07-25 | 2001-09-19 | Syngenta Ltd | Insecticidal mixture |
| GB0229803D0 (en) * | 2002-12-20 | 2003-01-29 | Syngenta Ltd | Chemical process |
| DE102004006324A1 (de) | 2004-02-10 | 2005-08-25 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| CN101643414B (zh) * | 2009-09-03 | 2012-11-07 | 贵阳柏丝特化工有限公司 | 一种含氯氟环丙烷羧酸酯类化合物及其制备和应用 |
| PT106198B (pt) | 2012-03-08 | 2014-10-07 | Sapec Agro S A | Formulação inseticida, método para a sua preparação e utilização da mesma |
| CN103918706B (zh) * | 2014-03-26 | 2015-12-09 | 河北省农林科学院植物保护研究所 | 含有噻嗪酮和高效氯氟氰菊酯的杀虫组合物及其应用 |
| WO2018050213A1 (en) | 2016-09-14 | 2018-03-22 | Endura S.P.A. | Improved process for the preparation of pyrethroids |
| CN109111373A (zh) * | 2018-10-09 | 2019-01-01 | 南通天泽化工有限公司 | 一种三氟氯氰菊酯的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2375161A1 (fr) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| JPS55104253A (en) * | 1979-02-06 | 1980-08-09 | Sumitomo Chem Co Ltd | Stereoisomer of more active carboxylic ester, method of obtaining it, insecticide and acaricide comprising it |
| BE886160A (nl) * | 1979-11-27 | 1981-05-14 | Shell Int Research | Cyclopropaan-carbonzure ester-derivaten |
| CA1150301A (en) * | 1979-11-27 | 1983-07-19 | Michael J. Bull | Cyclopropane carboxylic acid ester derivatives |
| GB2074573B (en) * | 1980-04-23 | 1983-11-16 | Shell Int Research | Process for preparing cyclopropane carboxylic acid ester derivatives |
| GB2075011B (en) * | 1980-04-23 | 1983-11-16 | Shell Int Research | Process for preparing cyclopropane carboxylic acid ester derivatives |
| GB2130199A (en) * | 1982-10-11 | 1984-05-31 | Ici Plc | An enantiomeric pair of cyhalothrin isomers and process for the preparation thereof |
-
1983
- 1983-08-31 AT AT83305006T patent/ATE28324T1/de not_active IP Right Cessation
- 1983-08-31 DE DE8383305006T patent/DE3372480D1/de not_active Expired
- 1983-08-31 GB GB08323360A patent/GB2128607A/en not_active Withdrawn
- 1983-08-31 EP EP83305006A patent/EP0107296B1/en not_active Expired
- 1983-09-12 NZ NZ205562A patent/NZ205562A/en unknown
- 1983-09-14 AU AU19118/83A patent/AU555545B2/en not_active Expired
- 1983-09-19 ZA ZA836965A patent/ZA836965B/xx unknown
- 1983-09-20 IL IL69775A patent/IL69775A/xx not_active IP Right Cessation
- 1983-09-26 US US06/535,625 patent/US4512931A/en not_active Expired - Lifetime
- 1983-10-06 CA CA000438485A patent/CA1208656A/en not_active Expired
- 1983-10-07 DK DK198304626A patent/DK174170B1/da not_active IP Right Cessation
- 1983-10-07 HU HU833475A patent/HU192856B/hu unknown
- 1983-10-11 JP JP58188563A patent/JPS5988454A/ja active Granted
- 1983-10-11 ES ES526410A patent/ES8600222A1/es not_active Expired
- 1983-10-13 CS CS837529A patent/CS251767B2/cs unknown
-
1987
- 1987-08-11 MY MYPI87001286A patent/MY100551A/en unknown
-
1990
- 1990-08-06 JP JP2206925A patent/JPH0372451A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4512931A (en) | 1985-04-23 |
| CA1208656A (en) | 1986-07-29 |
| ATE28324T1 (de) | 1987-08-15 |
| GB8323360D0 (en) | 1983-10-05 |
| AU555545B2 (en) | 1986-10-02 |
| JPS5988454A (ja) | 1984-05-22 |
| AU1911883A (en) | 1984-05-03 |
| DK462683A (da) | 1984-04-19 |
| MY100551A (en) | 1990-11-15 |
| CS752983A2 (en) | 1986-12-18 |
| ES526410A0 (es) | 1985-10-01 |
| ZA836965B (en) | 1984-06-27 |
| CS251767B2 (en) | 1987-08-13 |
| ES8600222A1 (es) | 1985-10-01 |
| EP0107296B1 (en) | 1987-07-15 |
| DE3372480D1 (en) | 1987-08-20 |
| HU192856B (en) | 1987-07-28 |
| JPH0336828B2 (enExample) | 1991-06-03 |
| EP0107296A1 (en) | 1984-05-02 |
| DK462683D0 (da) | 1983-10-07 |
| IL69775A (en) | 1986-11-30 |
| GB2128607A (en) | 1984-05-02 |
| NZ205562A (en) | 1986-04-11 |
| JPH0372451A (ja) | 1991-03-27 |
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