TW200447B - - Google Patents
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- Publication number
- TW200447B TW200447B TW079108928A TW79108928A TW200447B TW 200447 B TW200447 B TW 200447B TW 079108928 A TW079108928 A TW 079108928A TW 79108928 A TW79108928 A TW 79108928A TW 200447 B TW200447 B TW 200447B
- Authority
- TW
- Taiwan
- Prior art keywords
- configuration
- patent application
- hydroxy
- reaction
- item
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- -1 α-hydroxy-3-phenoxyphenyl ethyl Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound 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 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 229960001591 cyfluthrin Drugs 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 2
- 239000012346 acetyl chloride Substances 0.000 claims 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 241000270295 Serpentes Species 0.000 claims 1
- 101100070120 Xenopus laevis has-rs gene Proteins 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001804 chlorine Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000011049 filling Methods 0.000 description 8
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052704 radon Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 230000032050 esterification Effects 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- LLMLSUSAKZVFOA-INEUFUBQSA-N (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-INEUFUBQSA-N 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000004460 Tanacetum coccineum Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 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
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 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 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 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 1
- BAJXOIWQMMCIGQ-UHFFFAOYSA-N 2-(3-anilinophenyl)-2-hydroxyacetonitrile Chemical compound N#CC(O)C1=CC=CC(NC=2C=CC=CC=2)=C1 BAJXOIWQMMCIGQ-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HKKDKUMUWRTAIA-UHFFFAOYSA-N nitridooxidocarbon(.) Chemical compound [O]C#N HKKDKUMUWRTAIA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/438,657 US5028731A (en) | 1989-11-17 | 1989-11-17 | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200447B true TW200447B (https=) | 1993-02-21 |
Family
ID=23741488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW079108928A TW200447B (https=) | 1989-11-17 | 1990-10-23 |
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 |
| 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 |
| JPH0662536B2 (ja) | 1994-08-17 |
| 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 |
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