JPH0662536B2 - 活性種に富むシペルメスリンまたはシフルスリンの異性体の混合物の製造 - Google Patents
活性種に富むシペルメスリンまたはシフルスリンの異性体の混合物の製造Info
- Publication number
- JPH0662536B2 JPH0662536B2 JP2514365A JP51436590A JPH0662536B2 JP H0662536 B2 JPH0662536 B2 JP H0662536B2 JP 2514365 A JP2514365 A JP 2514365A JP 51436590 A JP51436590 A JP 51436590A JP H0662536 B2 JPH0662536 B2 JP H0662536B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- trans
- configuration
- phenoxyphenylacetonitrile
- hydroxy
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 33
- 239000005946 Cypermethrin Substances 0.000 title claims description 12
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical class CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 title claims description 12
- 229960005424 cypermethrin Drugs 0.000 title claims description 12
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical class CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 title claims description 9
- 229960001591 cyfluthrin Drugs 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 7
- 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 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 30
- -1 (2,2-dichloroethenyl) -2,2-dimethylcyclopropane carbonyl chloride Chemical compound 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 10
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CHLAOFANYRDCPD-UJURSFKZSA-N (1s,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O CHLAOFANYRDCPD-UJURSFKZSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- CHLAOFANYRDCPD-INEUFUBQSA-N (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O CHLAOFANYRDCPD-INEUFUBQSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 2
- BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 2
- UMTRHZBMIRLIKP-UHFFFAOYSA-N 2-phenoxy-2-phenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)OC1=CC=CC=C1 UMTRHZBMIRLIKP-UHFFFAOYSA-N 0.000 description 2
- CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 description 1
- OHAMOQALFCXZBV-UHFFFAOYSA-N 2,2-dichloroethenyl 2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)CC1C(=O)OC=C(Cl)Cl OHAMOQALFCXZBV-UHFFFAOYSA-N 0.000 description 1
- SFBGIISWPCQUIL-UHFFFAOYSA-N 2,3-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1C(C1C)C(=O)Cl SFBGIISWPCQUIL-UHFFFAOYSA-N 0.000 description 1
- VEQMUQZKBLIXLT-UHFFFAOYSA-N 2,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C)C1C(O)=O VEQMUQZKBLIXLT-UHFFFAOYSA-N 0.000 description 1
- FYIOXXUKFQPTJS-UHFFFAOYSA-N 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyacetonitrile Chemical compound N#CC(O)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 FYIOXXUKFQPTJS-UHFFFAOYSA-N 0.000 description 1
- LXXVVAQPCWSZJW-UHFFFAOYSA-N 2-hydroxy-2-phenoxy-2-phenylacetonitrile Chemical compound C=1C=CC=CC=1C(O)(C#N)OC1=CC=CC=C1 LXXVVAQPCWSZJW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241001012098 Omiodes indicata Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical class ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C07C255/39—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups with hydroxy groups esterified by derivatives of 2,2-dimethylcyclopropane carboxylic acids, e.g. of chrysanthemumic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Instrument Panels (AREA)
- Digital Computer Display Output (AREA)
- Controls And Circuits For Display Device (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US438,657 | 1989-11-17 | ||
| US07/438,657 US5028731A (en) | 1989-11-17 | 1989-11-17 | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
| PCT/US1990/005578 WO1991007379A1 (en) | 1989-11-17 | 1990-10-01 | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05501110A JPH05501110A (ja) | 1993-03-04 |
| JPH0662536B2 true JPH0662536B2 (ja) | 1994-08-17 |
Family
ID=23741488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2514365A Expired - Lifetime JPH0662536B2 (ja) | 1989-11-17 | 1990-10-01 | 活性種に富むシペルメスリンまたはシフルスリンの異性体の混合物の製造 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5028731A (https=) |
| EP (1) | EP0500572B1 (https=) |
| JP (1) | JPH0662536B2 (https=) |
| KR (1) | KR940011906B1 (https=) |
| BR (1) | BR9007850A (https=) |
| CA (1) | CA2068532C (https=) |
| DE (1) | DE69025478T2 (https=) |
| DK (1) | DK0500572T3 (https=) |
| ES (1) | ES2085916T3 (https=) |
| HU (1) | HU208304B (https=) |
| IL (1) | IL96298A (https=) |
| MX (1) | MX171955B (https=) |
| RU (1) | RU2060990C1 (https=) |
| TR (1) | TR25423A (https=) |
| TW (1) | TW200447B (https=) |
| WO (1) | WO1991007379A1 (https=) |
| ZA (1) | ZA908570B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| US5164411A (en) * | 1991-01-25 | 1992-11-17 | Fmc Corporation | Pyrethroid compositions |
| US8153145B2 (en) * | 2005-12-22 | 2012-04-10 | Fmc Corporation | Formulations of bifenthrin and enriched cypermethrin |
| US20120301532A1 (en) * | 2011-05-26 | 2012-11-29 | Allergy Technologies, Llc | Compositions and methods for treating materials with insecticides and potentiating agents |
| WO2019145221A1 (en) | 2018-01-29 | 2019-08-01 | BASF Agro B.V. | New agrochemical formulations |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769835A (en) * | 1953-12-09 | 1956-11-06 | Monsanto Chemicals | Process of producing alkyl acrylates by dehydrohalogenation using an anhydrous calcium sulfate catalyst |
| US3078306A (en) * | 1958-04-24 | 1963-02-19 | Basf Ag | Process for the production of alphachloroximes and their hydrochlorides |
| US3082236A (en) * | 1959-04-29 | 1963-03-19 | Wallace & Tiernan Inc | Peroxy esters of p-menthane hydroperoxides |
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| DE2850502A1 (de) * | 1977-11-24 | 1979-05-31 | Ciba Geigy Ag | 2,4,4,4-tetrachlorbuttersaeure-1,2,4, 4,4-pentachlor-but-1-enylester |
| DE2928986A1 (de) * | 1979-07-18 | 1981-02-05 | Bayer Ag | (+)-cis und (+) trans-2,2-dimethyl- 3-(2,2-dichlor-vinyl)-cyclopropan-1- carbonsaeure-(+-) - alpha -cyano-3-phenoxy4-fluor-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
| FR2471369A1 (fr) * | 1979-12-17 | 1981-06-19 | Roussel Uclaf | Nouvelles imines, derivant d'esters d'acides formyl cyclopropane carboxyliques, leur procede de preparation et leur application a la preparation d'esters insecticides |
| DE3200484A1 (de) * | 1982-01-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Aminoalkylester, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmittel |
| JPS60202843A (ja) * | 1984-03-27 | 1985-10-14 | Sumitomo Chem Co Ltd | エステル誘導体の合成方法 |
| JP2982339B2 (ja) * | 1991-02-25 | 1999-11-22 | ソニー株式会社 | 光ディスクカートリッジと光ディスク装置 |
-
1989
- 1989-11-17 US US07/438,657 patent/US5028731A/en not_active Expired - Lifetime
-
1990
- 1990-10-01 ES ES90915553T patent/ES2085916T3/es not_active Expired - Lifetime
- 1990-10-01 CA CA002068532A patent/CA2068532C/en not_active Expired - Fee Related
- 1990-10-01 KR KR1019920701159A patent/KR940011906B1/ko not_active Expired - Fee Related
- 1990-10-01 EP EP90915553A patent/EP0500572B1/en not_active Expired - Lifetime
- 1990-10-01 JP JP2514365A patent/JPH0662536B2/ja not_active Expired - Lifetime
- 1990-10-01 BR BR909007850A patent/BR9007850A/pt not_active IP Right Cessation
- 1990-10-01 RU SU905052420A patent/RU2060990C1/ru not_active IP Right Cessation
- 1990-10-01 DE DE69025478T patent/DE69025478T2/de not_active Expired - Fee Related
- 1990-10-01 WO PCT/US1990/005578 patent/WO1991007379A1/en not_active Ceased
- 1990-10-01 HU HU921627A patent/HU208304B/hu unknown
- 1990-10-01 DK DK90915553.3T patent/DK0500572T3/da active
- 1990-10-23 TW TW079108928A patent/TW200447B/zh active
- 1990-10-25 ZA ZA908570A patent/ZA908570B/xx unknown
- 1990-11-09 IL IL9629890A patent/IL96298A/en not_active IP Right Cessation
- 1990-11-14 TR TR90/1096A patent/TR25423A/xx unknown
- 1990-11-16 MX MX023375A patent/MX171955B/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69025478D1 (de) | 1996-03-28 |
| HU9201627D0 (en) | 1993-04-28 |
| IL96298A (en) | 1995-10-31 |
| US5028731A (en) | 1991-07-02 |
| TW200447B (https=) | 1993-02-21 |
| KR920703518A (ko) | 1992-12-18 |
| JPH05501110A (ja) | 1993-03-04 |
| EP0500572A4 (en) | 1992-10-07 |
| KR940011906B1 (ko) | 1994-12-27 |
| WO1991007379A1 (en) | 1991-05-30 |
| BR9007850A (pt) | 1992-10-06 |
| EP0500572A1 (en) | 1992-09-02 |
| MX171955B (es) | 1993-11-24 |
| IL96298A0 (en) | 1991-08-16 |
| DE69025478T2 (de) | 1996-10-24 |
| CA2068532C (en) | 1995-05-16 |
| HU208304B (en) | 1993-09-28 |
| DK0500572T3 (da) | 1996-06-24 |
| RU2060990C1 (ru) | 1996-05-27 |
| ES2085916T3 (es) | 1996-06-16 |
| TR25423A (tr) | 1993-03-01 |
| CA2068532A1 (en) | 1991-05-18 |
| EP0500572B1 (en) | 1996-02-21 |
| ZA908570B (en) | 1991-08-28 |
| HUT62554A (en) | 1993-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH620890A5 (https=) | ||
| JP5603169B2 (ja) | （ｅ）−３−メチル−２−シクロペンタデセノンの製造方法 | |
| Tai et al. | Stereochemical studies of the hydrogenation with an asymmetrically modified Raney nickel catalyst. The hydrogenation of acetylacetone. | |
| JPH0662536B2 (ja) | 活性種に富むシペルメスリンまたはシフルスリンの異性体の混合物の製造 | |
| JP3053872B2 (ja) | （＋）−（１ｒ）−シス−３−オキソ−２−ペンチル−１−シクロペンタン酢酸の製造法 | |
| EP3506748A1 (en) | Improved method for the synthesis of permethrin | |
| HU225613B1 (en) | Method for producing optically active chrysantaemic acid | |
| EP0165070B1 (en) | Method for racemization of chrysanthemic acid or its ester | |
| JP3032447B2 (ja) | 光学活性な２−プロピルオクタン酸の製造方法 | |
| HU207712B (en) | Process for pransforming piretroide isomeresinto formes of stronger pesticide activity | |
| JPH0453850B2 (https=) | ||
| CA1140565A (fr) | PROCEDE DE PREPARATION D'ALCOOLS .alpha.-CYANES OPTIQUEMENTS ACTIFS | |
| TWI329100B (en) | Chemical process | |
| JPH05201881A (ja) | 環状化合物の転移方法 | |
| EP0342843B1 (en) | Process for preparing racemic dihalovinylcyclopropane carboxylic acid halides | |
| KR100884558B1 (ko) | 고수율 및 고 광학순도의 광학활성 아미드의 제조방법 | |
| JPH11509534A (ja) | シクロプロパンカルボン酸及びそれらの中間体の製造方法 | |
| CN1298862A (zh) | 制备(+)－反－菊－酸的方法 | |
| JPH0253429B2 (https=) | ||
| JP3197914B2 (ja) | 新規シクロプロパンカルボン酸エステルを含有する衣料用防虫剤 | |
| CH624917A5 (en) | Process for the stereoselective hydrogenation of cyclic compounds | |
| EP1728781A1 (en) | Process for production of (1-alkenyl)cyclopropanes | |
| KR960010531B1 (ko) | 퍼메스린의 새로운 제조방법 | |
| US4948914A (en) | Process for preparing trans-2,2-dimethyl-3-(2,2-dihalovinyl)cyclopropane carboxylic acid esters | |
| JPH06335398A (ja) | シクロヘキセンジオール誘導体 |