HU210098B - Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures - Google Patents
Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures Download PDFInfo
- Publication number
- HU210098B HU210098B HU678089A HU678089A HU210098B HU 210098 B HU210098 B HU 210098B HU 678089 A HU678089 A HU 678089A HU 678089 A HU678089 A HU 678089A HU 210098 B HU210098 B HU 210098B
- Authority
- HU
- Hungary
- Prior art keywords
- acid
- reactor
- mixture
- weight
- optionally
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 34
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound 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 43
- 239000005946 Cypermethrin Substances 0.000 title claims description 35
- 229960005424 cypermethrin Drugs 0.000 title claims description 35
- 239000012141 concentrate Substances 0.000 title claims description 4
- 230000000749 insecticidal effect Effects 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 230000009466 transformation Effects 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 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 abstract description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 84
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 74
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- 239000003586 protic polar solvent Substances 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000011976 maleic acid Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000011260 aqueous acid Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008043 acidic salts Chemical class 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical group O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 9
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 claims 2
- 239000002516 radical scavenger Substances 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 230000017105 transposition Effects 0.000 claims 1
- 239000000725 suspension Substances 0.000 abstract description 6
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000000844 transformation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000002178 crystalline material Substances 0.000 description 12
- -1 2,2-Dimethyl-3- (2 ', 2'-dichloro-vinyl) -cyclopropanecarboxylic acid α-cyano (m-phenoxybenzyl) ester Chemical class 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KAATUXNTWXVJKI-FLXSOZOKSA-N [(S)-cyano-(3-phenoxyphenyl)methyl] (1R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-FLXSOZOKSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- 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 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-N 2,2-diethylpropanedioic acid Chemical compound CCC(CC)(C(O)=O)C(O)=O LTMRRSWNXVJMBA-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229910002018 Aerosil® 300 Inorganic materials 0.000 description 1
- 229940099580 Aldehyde binder Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU678089A HU210098B (en) | 1989-12-27 | 1989-12-27 | Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures |
| AT90901870T ATE90338T1 (de) | 1989-01-17 | 1990-01-17 | Verfahren zur herstellung von cypermethrinisomeren. |
| US07/601,767 US5153349A (en) | 1989-01-17 | 1990-01-17 | Process for the preparation of cypermethrine isomers |
| BR909004617A BR9004617A (pt) | 1989-01-17 | 1990-01-17 | Processo para a preparacao de isomeros de cipermetrina |
| CA002020356A CA2020356C (en) | 1989-01-17 | 1990-01-17 | Process for the preparation of cypermethrine isomers |
| DK90901870.7T DK0404922T3 (da) | 1989-01-17 | 1990-01-17 | Fremgangsmåde til fremstilling af cypermethrin-isomerer |
| MD94-0336A MD466G2 (ro) | 1989-12-27 | 1990-01-17 | Procedeu de preparare a amesticurilor de izomeri ai cipermetrinei |
| ES90901870T ES2057531T3 (es) | 1989-01-17 | 1990-01-17 | Procedimiento para la preparacion de isomeros de cipermetrina. |
| DE9090901870T DE69001866T2 (de) | 1989-01-17 | 1990-01-17 | Verfahren zur herstellung von cypermethrin-isomeren. |
| EP90901870A EP0404922B1 (en) | 1989-01-17 | 1990-01-17 | Process for the preparation of cypermethrine isomers |
| KR1019900702058A KR940003358B1 (ko) | 1989-01-17 | 1990-01-17 | 사이퍼메트린 이성체 혼합물의 제조방법 |
| PCT/HU1990/000006 WO1990008132A1 (en) | 1989-01-17 | 1990-01-17 | Process for the preparation of cypermethrine isomers |
| SU905010694A RU2045516C1 (ru) | 1989-12-27 | 1990-01-17 | Способ получения смесей изомеров циперметрина |
| AR90316104A AR247726A1 (es) | 1989-12-27 | 1990-02-07 | Procedimiento para obtener mezclas de isomeros de cipermetrina y composicion artropodicida a base de las mismas |
| TR20790A TR25674A (tr) | 1989-12-27 | 1990-02-28 | Sipermetrin izomerlerini hazirlamaya mahsus yöntem |
| LVP-93-586A LV10232B (en) | 1989-12-27 | 1993-06-15 | Process for the preparation of cypermethrine isomers |
| LVP-93-628A LV10771B (en) | 1989-01-17 | 1993-06-19 | Process for the preparation of cypermetrine isomers |
| GEAP19931388A GEP19981465B (en) | 1989-01-17 | 1993-08-12 | Process for the preparation of cypermethrine isomers |
| GEAP19931389A GEP19981466B (en) | 1989-01-17 | 1993-08-12 | Process for the preparation of cypermethrine isomers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU678089A HU210098B (en) | 1989-12-27 | 1989-12-27 | Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU896780D0 HU896780D0 (enrdf_load_stackoverflow) | 1990-03-28 |
| HUT55746A HUT55746A (en) | 1991-06-28 |
| HU210098B true HU210098B (en) | 1995-02-28 |
Family
ID=10972006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU678089A HU210098B (en) | 1989-01-17 | 1989-12-27 | Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR247726A1 (enrdf_load_stackoverflow) |
| HU (1) | HU210098B (enrdf_load_stackoverflow) |
| LV (1) | LV10232B (enrdf_load_stackoverflow) |
| MD (1) | MD466G2 (enrdf_load_stackoverflow) |
| RU (1) | RU2045516C1 (enrdf_load_stackoverflow) |
| TR (1) | TR25674A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039961A1 (es) * | 2002-06-06 | 2005-03-09 | Novartis Ag | Derivados de amidoacetonitrilo y su uso como pesticida |
Family Cites Families (2)
| 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 |
| US4751634A (en) * | 1985-06-14 | 1988-06-14 | International Business Machines Corporation | Multiple port communications adapter apparatus |
-
1989
- 1989-12-27 HU HU678089A patent/HU210098B/hu not_active IP Right Cessation
-
1990
- 1990-01-17 MD MD94-0336A patent/MD466G2/ro active IP Right Grant
- 1990-01-17 RU SU905010694A patent/RU2045516C1/ru not_active IP Right Cessation
- 1990-02-07 AR AR90316104A patent/AR247726A1/es active
- 1990-02-28 TR TR20790A patent/TR25674A/xx unknown
-
1993
- 1993-06-15 LV LVP-93-586A patent/LV10232B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2045516C1 (ru) | 1995-10-10 |
| HUT55746A (en) | 1991-06-28 |
| LV10232A (lv) | 1994-10-20 |
| MD466F1 (en) | 1996-09-30 |
| LV10232B (en) | 1995-04-20 |
| HU896780D0 (enrdf_load_stackoverflow) | 1990-03-28 |
| AR247726A1 (es) | 1995-03-31 |
| TR25674A (tr) | 1993-07-01 |
| MD466G2 (ro) | 1997-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69624657T2 (de) | Verbesserung bei der Herstellung von N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethyl-acetamide | |
| EP0039844A2 (de) | Verfahren zur Herstellung von O-substituierten Derivaten des (+)-Cyanidan-3-ols | |
| PL146571B1 (en) | Method of obtaining a mixture of volatile enantiomers of alpha-cyno-3-phenoxy-4-fluorobenzyl-permetrinic ester | |
| DE1518934A1 (de) | Verfahren zur Herstellung von Silylgruppenhaltigen Verbindungen | |
| DE1966974A1 (de) | Dimethylformiminiumhalogensulfit- n-halogenide, verfahren zu deren herstellung sowie deren verwendung | |
| WO2007009143A2 (de) | Verfahren zur herstellung nebivolol | |
| EP1087945B1 (de) | Verfahren zur herstellung von carbonyldiimidazol | |
| HU210098B (en) | Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures | |
| DE69001866T2 (de) | Verfahren zur herstellung von cypermethrin-isomeren. | |
| EP0915840A1 (de) | Verfahren zur herstellung von substituierten valinamid-derivaten | |
| DE2640616C3 (de) | Verfahren zur Herstellung von N-Acyl-2-aiylglycinen | |
| DD273250A5 (de) | Verfahren zur herstellung von alpha-(1-methylethyl)-3,4-dimethoxybenzolacetonitril | |
| DE3411203C1 (de) | Verfahren zur Herstellung von N-Cyanimidoestern | |
| DE69008431T2 (de) | Verfahren zur Herstellung von Imidazol-Derivaten. | |
| DE2627709C2 (de) | Malonsäure-pentachlorphenylester und deren Herstellung | |
| EP3392237A1 (de) | Verfahren zur herstellung von acroleincyanhydrinen | |
| DE3543021A1 (de) | Verbesserte verfahren zur herstellung von d-threo-1-(p-methylsulfonylphenyl) -2-dichloracetamido-propandiol-1,3-(thiamphenicol) sowie verwendung geeigneter zwischenprodukte | |
| DE2362687A1 (de) | Verfahren zur razematspaltung von d,l-penicillamin | |
| RU2051886C1 (ru) | Способ получения смеси изомеров циперметрина в форме стабилизированного кристаллического продукта | |
| EP4519248A1 (de) | Verfahren zur herstellung von 4-[5-[bis(2-chlorethyl)amino]-1-methyl-1h-benzo[d]imidazol-2-yl]butansäurealkylestern und formylierten derivaten | |
| DE2619321C2 (de) | Oxalsäurederivate, ihre Herstellung und ihre Verwendung | |
| DE850297C (de) | Verfahren zur Herstellung von Amidinsalzen | |
| EP1070706B1 (de) | Verfahren zur Herstellung von 1-substituierten 5-Hydroxy-imidazolin-2,4-dionen und 1-substituierten 5-Alkoxy-imidazolin-2,4-dionen | |
| EP0293752A2 (de) | Verfahren zur Herstellung von E-2-Propyl-2-pentensäure und physiologisch verträglichen Salzen derselben | |
| DE1926857A1 (de) | 6-Nitro-2-oximinohexansaeurederivate und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HPC4 | Succession in title of patentee |
Owner name: AGRO-CHEMIE NOEVENYVEDOESZER GYARTO, ERTEKESITOE E |
|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |