DK171797B1 - Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. - Google Patents
Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. Download PDFInfo
- Publication number
- DK171797B1 DK171797B1 DK085495A DK85495A DK171797B1 DK 171797 B1 DK171797 B1 DK 171797B1 DK 085495 A DK085495 A DK 085495A DK 85495 A DK85495 A DK 85495A DK 171797 B1 DK171797 B1 DK 171797B1
- Authority
- DK
- Denmark
- Prior art keywords
- ppm
- compound
- cyclopropane
- dichloro
- iii
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 6
- 150000001942 cyclopropanes Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 239000011701 zinc Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- DKWHBVHUOGYKOM-QRHDOFTISA-N (1r,3r)-3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C(O)C(Cl)(Cl)C(F)(F)F)[C@H]1C(O)=O DKWHBVHUOGYKOM-QRHDOFTISA-N 0.000 claims description 8
- GMWQNPAZOIIJSH-OVEKKEMJSA-N (1r,5s)-4-(1,1-dichloro-2,2,2-trifluoroethyl)-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound O=C1OC(C(Cl)(Cl)C(F)(F)F)[C@H]2[C@@H]1C2(C)C GMWQNPAZOIIJSH-OVEKKEMJSA-N 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000007769 metal material Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- QHAPONCMFJQXEN-MROZADKFSA-N (1r,4r,5s)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound [C@H]1([C@@H](OC2=O)O)[C@@H]2C1(C)C QHAPONCMFJQXEN-MROZADKFSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- SPVZAYWHHVLPBN-WREUKLMHSA-N (1r,3r)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(O)=O SPVZAYWHHVLPBN-WREUKLMHSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- -1 α-cyano-3-phenoxybenzyl Chemical group 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002728 pyrethroid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SPVZAYWHHVLPBN-AVCLAYCWSA-N (1s,3s)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-AVCLAYCWSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YSAQNUKCLXBCEI-UHFFFAOYSA-N 2-diazonio-1-(2,2-dichloro-1,1,1-trifluoro-5-methylhex-4-en-3-yl)oxyethenolate Chemical compound CC(C)=CC(C(Cl)(Cl)C(F)(F)F)OC(=O)C=[N+]=[N-] YSAQNUKCLXBCEI-UHFFFAOYSA-N 0.000 description 1
- PTQGFDXPHNRDCV-UHFFFAOYSA-N 3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=O)C1C(O)=O PTQGFDXPHNRDCV-UHFFFAOYSA-N 0.000 description 1
- 241000596871 Ixia Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom 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
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005356 chiral GC Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- 238000012866 crystallographic experiment Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AOLAMWZAGOXVJB-RNFRBKRXSA-N methyl (1s,3s)-3-(dimethoxymethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(OC)[C@H]1[C@H](C(=O)OC)C1(C)C AOLAMWZAGOXVJB-RNFRBKRXSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/35—Unsaturated compounds having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (40)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK085495A DK171797B1 (da) | 1995-07-21 | 1995-07-21 | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. |
| ZA965688A ZA965688B (en) | 1995-07-21 | 1996-07-04 | A process for the preparing of cyclopropane carboxylic acids and intermediates therefor |
| CA002224818A CA2224818C (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| HU9802288A HU218983B (hu) | 1995-07-21 | 1996-07-17 | Eljárás ciklopropánkarbonsavak előállítására és köztitermékeik |
| US09/000,034 US5986130A (en) | 1995-07-21 | 1996-07-17 | Process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| UA98010033A UA59338C2 (uk) | 1995-07-21 | 1996-07-17 | Спосіб одержання циклопропанкарбонових кислот та проміжні сполуки |
| PCT/DK1996/000326 WO1997003941A1 (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| CNB021440948A CN1258514C (zh) | 1995-07-21 | 1996-07-17 | 一种制备环丙烷羧酸及其中间体的方法 |
| DK96924795T DK0842137T3 (da) | 1995-07-21 | 1996-07-17 | Fremgangsmåde til fremstilling af cyclopro-pancarboxylsyrer og mellemprodukter herfor |
| DE69607627T DE69607627T2 (de) | 1995-07-21 | 1996-07-17 | Verfahren zur herstellung von cyclopropancarbonsäuren und zwischenprodukte für dieses verfahren |
| NZ313133A NZ313133A (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| EA199800143A EA000683B1 (ru) | 1995-07-21 | 1996-07-17 | Способ получения циклопропанкарбоновых кислот и их промежуточных соединений |
| PT96924795T PT842137E (pt) | 1995-07-21 | 1996-07-17 | Processo para a preparacao de acidos ciclopropanocarboxilicos e intermediarios para esta preparacao |
| AT96924795T ATE191446T1 (de) | 1995-07-21 | 1996-07-17 | Verfahren zur herstellung von cyclopropancarbonsäuren und zwischenprodukte für dieses verfahren |
| EE9800019A EE03521B1 (et) | 1995-07-21 | 1996-07-17 | Protsess tsüklopropaankarboksüülhapete ja nende vaheühendite valmistamiseks |
| JP50618997A JP3457005B2 (ja) | 1995-07-21 | 1996-07-17 | 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 |
| SK71-98A SK282494B6 (sk) | 1995-07-21 | 1996-07-17 | Spôsob výroby cyklopropánkarboxylových kyselín a medziprodukty |
| PL96324867A PL182824B1 (pl) | 1995-07-21 | 1996-07-17 | Sposób wytwarzania kwasów cyklopropanokarboksylowych i nowe związki pośrednie |
| MX9800440A MX9800440A (es) | 1995-07-21 | 1996-07-17 | Procedimiento para la preparacion de acidos ciclopropano carboxilicos e intermediarios de los mismos. |
| CN96196866A CN1117061C (zh) | 1995-07-21 | 1996-07-17 | 一种制备环丙烷羧酸及其中间体的方法 |
| IL12262496A IL122624A (en) | 1995-07-21 | 1996-07-17 | Process for the preparation of 2-chloro-3,3,3-trifluoro-1-propenyl cyclopropane carboxylic acid and intermediates therefor |
| SI9630194T SI0842137T1 (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| BR9609740-0A BR9609740A (pt) | 1995-07-21 | 1996-07-17 | Processo para a preparação de composto, e, composto |
| EP96924795A EP0842137B1 (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| ES96924795T ES2145467T3 (es) | 1995-07-21 | 1996-07-17 | Un procedimiento para la preparacion de acidos ciclopropano-carboxilicos e intermedios de los mismos. |
| TR1998/00090T TR199800090T1 (xx) | 1995-07-21 | 1996-07-17 | Siklopropan karboksilik asitleri ve bunlar�n ara bile�iklerini haz�lamak i�in y�ntem. |
| RO98-00083A RO117790B1 (ro) | 1995-07-21 | 1996-07-17 | Procedeu de preparare a acizilor ciclopropan-carboxilici si intermediari pentru realizarea procedeului |
| KR1019980700441A KR100284147B1 (ko) | 1995-07-21 | 1996-07-17 | 사이클로프로판 카복실산 및 이의 중간체의 제조방법 |
| CZ1998186A CZ293407B6 (cs) | 1995-07-21 | 1996-07-17 | Způsob výroby cyklopropankarboxylových kyselin |
| IL13710896A IL137108A (en) | 1995-07-21 | 1996-07-17 | (1r, 5s)-4- (1,1-dichloro-2,2,2-trifluoroethyl)-6,6-dimethyl-3-oxabicyclo [3.1.0] hexan-2-one |
| AU65136/96A AU701546C (en) | 1995-07-21 | 1996-07-17 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| ARP960103668A AR002899A1 (es) | 1995-07-21 | 1996-07-19 | Un procedimiento para la preparacion de acidos ciclopropano carboxilicos |
| TW085111305A TW339331B (en) | 1995-07-21 | 1996-09-16 | Process for the preparation of cyclopropane carboxylic acids and the intermediates |
| ARP970101469A AR010461A2 (es) | 1995-07-21 | 1997-04-11 | Derivados de ciclopropano utiles como intermediarios para la preparacion de acidos ciclopropano carboxilicos |
| NO980256A NO309264B1 (no) | 1995-07-21 | 1998-01-20 | Fremgangsmåte for fremstilling av syklopropankarboksylsyrer og mellomprodukter av disse |
| HK99100255A HK1015350A1 (en) | 1995-07-21 | 1999-01-19 | Process for the preparation of cyclopropane carboxylic acid and intermediates therefor |
| GR20000401533T GR3033832T3 (en) | 1995-07-21 | 2000-06-30 | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor |
| JP2001354657A JP3807605B2 (ja) | 1995-07-21 | 2001-11-20 | シクロプロパンカルボン酸エステルの製造における中間体 |
| JP2001354656A JP2002201188A (ja) | 1995-07-21 | 2001-11-20 | シクロプロパンカルボン酸エステルの製造における中間体 |
| HK04109284A HK1066210A1 (en) | 1995-07-21 | 2004-11-24 | A process for the preparation of cyclopropane carboxylic acids and its intermediates therefor |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK085495A DK171797B1 (da) | 1995-07-21 | 1995-07-21 | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. |
| DK85495 | 1995-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK85495A DK85495A (da) | 1997-01-22 |
| DK171797B1 true DK171797B1 (da) | 1997-06-02 |
Family
ID=8098295
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK085495A DK171797B1 (da) | 1995-07-21 | 1995-07-21 | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. |
| DK96924795T DK0842137T3 (da) | 1995-07-21 | 1996-07-17 | Fremgangsmåde til fremstilling af cyclopro-pancarboxylsyrer og mellemprodukter herfor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK96924795T DK0842137T3 (da) | 1995-07-21 | 1996-07-17 | Fremgangsmåde til fremstilling af cyclopro-pancarboxylsyrer og mellemprodukter herfor |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5986130A (xx) |
| EP (1) | EP0842137B1 (xx) |
| JP (3) | JP3457005B2 (xx) |
| KR (1) | KR100284147B1 (xx) |
| CN (2) | CN1117061C (xx) |
| AR (2) | AR002899A1 (xx) |
| AT (1) | ATE191446T1 (xx) |
| BR (1) | BR9609740A (xx) |
| CA (1) | CA2224818C (xx) |
| CZ (1) | CZ293407B6 (xx) |
| DE (1) | DE69607627T2 (xx) |
| DK (2) | DK171797B1 (xx) |
| EA (1) | EA000683B1 (xx) |
| EE (1) | EE03521B1 (xx) |
| ES (1) | ES2145467T3 (xx) |
| GR (1) | GR3033832T3 (xx) |
| HK (2) | HK1015350A1 (xx) |
| HU (1) | HU218983B (xx) |
| IL (2) | IL137108A (xx) |
| MX (1) | MX9800440A (xx) |
| NO (1) | NO309264B1 (xx) |
| NZ (1) | NZ313133A (xx) |
| PL (1) | PL182824B1 (xx) |
| PT (1) | PT842137E (xx) |
| RO (1) | RO117790B1 (xx) |
| SI (1) | SI0842137T1 (xx) |
| SK (1) | SK282494B6 (xx) |
| TR (1) | TR199800090T1 (xx) |
| TW (1) | TW339331B (xx) |
| UA (1) | UA59338C2 (xx) |
| WO (1) | WO1997003941A1 (xx) |
| ZA (1) | ZA965688B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK174698B1 (da) * | 1998-02-18 | 2003-09-22 | Cheminova Agro As | Fremgangsmåde til fremstilling af cyclopropancarboxylsyrer |
| GB9808619D0 (en) * | 1998-04-22 | 1998-06-24 | Zeneca Ltd | Chemical process |
| CN100500307C (zh) * | 2007-04-02 | 2009-06-17 | 浙江工业大学 | 一种基于连续输送的条烟异步分拣法 |
| WO2015021991A1 (en) | 2013-08-16 | 2015-02-19 | Cheminova A/S | Combination of 2-methylbiphenyl-3-ylmethyl (z)-(1r)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate with at least one insecticide, acaricide, nematicide and/or fungicide. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2000764B (en) * | 1977-03-23 | 1982-04-28 | Ici Ltd | Halogenated esters |
| FR2396006A1 (fr) * | 1977-06-27 | 1979-01-26 | Roussel Uclaf | Nouveaux composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliques |
| CA1146581A (en) * | 1977-12-16 | 1983-05-17 | Pieter A. Verbrugge | Intermediates in the preparation of cyclopropylcarboxylate esters and process for their manufacture |
| US4333950A (en) * | 1979-05-24 | 1982-06-08 | Fmc Corporation | (+)-4-Substituted-2-indanol insecticidal ester derivatives |
| FR2607133B1 (fr) * | 1986-11-20 | 1989-05-05 | Roussel Uclaf | Nouveaux derives de l'acide 2,2-dimethyl cyclopropane carboxylique portant en 3 une chaine halogenee saturee, leur procede de preparation et leur application comme pesticides |
-
1995
- 1995-07-21 DK DK085495A patent/DK171797B1/da not_active IP Right Cessation
-
1996
- 1996-07-04 ZA ZA965688A patent/ZA965688B/xx unknown
- 1996-07-17 DK DK96924795T patent/DK0842137T3/da active
- 1996-07-17 EA EA199800143A patent/EA000683B1/ru not_active IP Right Cessation
- 1996-07-17 US US09/000,034 patent/US5986130A/en not_active Expired - Lifetime
- 1996-07-17 EP EP96924795A patent/EP0842137B1/en not_active Expired - Lifetime
- 1996-07-17 UA UA98010033A patent/UA59338C2/uk unknown
- 1996-07-17 WO PCT/DK1996/000326 patent/WO1997003941A1/en active IP Right Grant
- 1996-07-17 MX MX9800440A patent/MX9800440A/es unknown
- 1996-07-17 CN CN96196866A patent/CN1117061C/zh not_active Expired - Lifetime
- 1996-07-17 BR BR9609740-0A patent/BR9609740A/pt not_active IP Right Cessation
- 1996-07-17 PL PL96324867A patent/PL182824B1/pl unknown
- 1996-07-17 JP JP50618997A patent/JP3457005B2/ja not_active Expired - Lifetime
- 1996-07-17 AT AT96924795T patent/ATE191446T1/de active
- 1996-07-17 NZ NZ313133A patent/NZ313133A/xx not_active IP Right Cessation
- 1996-07-17 SI SI9630194T patent/SI0842137T1/xx unknown
- 1996-07-17 CN CNB021440948A patent/CN1258514C/zh not_active Expired - Lifetime
- 1996-07-17 TR TR1998/00090T patent/TR199800090T1/xx unknown
- 1996-07-17 CA CA002224818A patent/CA2224818C/en not_active Expired - Lifetime
- 1996-07-17 KR KR1019980700441A patent/KR100284147B1/ko not_active IP Right Cessation
- 1996-07-17 CZ CZ1998186A patent/CZ293407B6/cs not_active IP Right Cessation
- 1996-07-17 EE EE9800019A patent/EE03521B1/xx not_active IP Right Cessation
- 1996-07-17 IL IL13710896A patent/IL137108A/xx not_active IP Right Cessation
- 1996-07-17 ES ES96924795T patent/ES2145467T3/es not_active Expired - Lifetime
- 1996-07-17 PT PT96924795T patent/PT842137E/pt unknown
- 1996-07-17 RO RO98-00083A patent/RO117790B1/ro unknown
- 1996-07-17 IL IL12262496A patent/IL122624A/xx not_active IP Right Cessation
- 1996-07-17 HU HU9802288A patent/HU218983B/hu unknown
- 1996-07-17 SK SK71-98A patent/SK282494B6/sk not_active IP Right Cessation
- 1996-07-17 DE DE69607627T patent/DE69607627T2/de not_active Expired - Lifetime
- 1996-07-19 AR ARP960103668A patent/AR002899A1/es active IP Right Grant
- 1996-09-16 TW TW085111305A patent/TW339331B/zh not_active IP Right Cessation
-
1997
- 1997-04-11 AR ARP970101469A patent/AR010461A2/es active IP Right Grant
-
1998
- 1998-01-20 NO NO980256A patent/NO309264B1/no not_active IP Right Cessation
-
1999
- 1999-01-19 HK HK99100255A patent/HK1015350A1/xx not_active IP Right Cessation
-
2000
- 2000-06-30 GR GR20000401533T patent/GR3033832T3/el unknown
-
2001
- 2001-11-20 JP JP2001354657A patent/JP3807605B2/ja not_active Expired - Fee Related
- 2001-11-20 JP JP2001354656A patent/JP2002201188A/ja active Pending
-
2004
- 2004-11-24 HK HK04109284A patent/HK1066210A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4405640A (en) | Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides | |
| JPH0643369B2 (ja) | ピレトリン酸と関連したシクロプロパンカルボン酸のエステル及びそれらの製造方法 | |
| US4429153A (en) | Halogenated esters | |
| DK171797B1 (da) | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. | |
| EP0221635B1 (en) | Fluoro alcohols and insecticidal esters thereof | |
| US4479005A (en) | Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids | |
| CH638485A5 (it) | Piretroidi e loro processi di preparazione. | |
| MXPA98000440A (en) | Procedure for the preparation of carboxilic and intermediary cyclopropan acids of the mis | |
| HU203309B (en) | Process for producing unsaturated alcohol derivatives | |
| AU701546C (en) | A process for the preparation of cyclopropane carboxylic acids and intermediates therefor | |
| US4902835A (en) | Fluorinated butene derivatives and methods for their preparation | |
| US4429149A (en) | 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid | |
| JPS5930710B2 (ja) | 殺虫殺だに中間体とその製法 | |
| HU201321B (en) | Process for producing cyclopropane lactons | |
| US4299972A (en) | Preparation of cyclopropanecarboxylic acid esters | |
| US4515956A (en) | Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids | |
| US4071542A (en) | Synthesis of hydroxycyclopenten-1-ones | |
| US4032577A (en) | Unsaturated ketones | |
| DK161704B (da) | Cyclopropancarboxylsyrelactonderivater og fremgangsmaader til fremstilling deraf | |
| JPH0380788B2 (xx) | ||
| HU185218B (en) | Process for producing new lactolalcohol-cyclopropane-carboxylate derivatives | |
| GB2151625A (en) | Process for the preparation of 3,5-ethano-2-2,4-dodecadienoates | |
| JPH05213823A (ja) | 光学活性２−イソプロペニル−シクロブタンカルボン酸エステル類の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |
Country of ref document: DK |