NO309264B1 - Fremgangsmåte for fremstilling av syklopropankarboksylsyrer og mellomprodukter av disse - Google Patents

Fremgangsmåte for fremstilling av syklopropankarboksylsyrer og mellomprodukter av disse Download PDF

Info

Publication number: NO309264B1
Authority: NO; Norway
Prior art keywords: ppm; dichloro; dimethyl; cyclopropane carboxylic; carboxylic acid
Prior art date: 1995-07-21

Application number

NO980256A

Other languages

English (en)

Norwegian (no)

Other versions

NO980256L (no

NO980256D0 (no

Inventor

Per Dausell Klemmensen

Hans Kolind-Andersen

Ib Winckelmann

Original Assignee

Cheminova Agro As

Priority date (The priority date 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 date listed.)

1995-07-21

Filing date

1998-01-20

Publication date

2001-01-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8098295&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO309264(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-01-20 Application filed by Cheminova Agro As filed Critical Cheminova Agro As

1998-01-20 Publication of NO980256L publication Critical patent/NO980256L/no

1998-01-20 Publication of NO980256D0 publication Critical patent/NO980256D0/no

2001-01-08 Publication of NO309264B1 publication Critical patent/NO309264B1/no

Links

239000000543 intermediate Substances 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 9
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
239000012467 final product Substances 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
229910052725 zinc Inorganic materials 0.000 claims description 7
239000011701 zinc Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
DKWHBVHUOGYKOM-OVEKKEMJSA-N (1r,3s)-3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical group CC1(C)[C@@H](C(O)C(Cl)(Cl)C(F)(F)F)[C@H]1C(O)=O DKWHBVHUOGYKOM-OVEKKEMJSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000012024 dehydrating agents‎ Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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 group O=C1OC(C(Cl)(Cl)C(F)(F)F)[C@H]2[C@@H]1C2(C)C GMWQNPAZOIIJSH-OVEKKEMJSA-N 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 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000007769 metal material Substances 0.000 claims 1
239000000047 product Substances 0.000 description 11
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
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 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
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
238000005481 NMR spectroscopy Methods 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000000203 mixture Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 5
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
239000008346 aqueous phase Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000002728 pyrethroid Substances 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
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
-1 2-methylbiphenyl-3-ylmethyl Chemical group 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
238000004458 analytical method Methods 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
238000000605 extraction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012528 membrane Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000843 powder 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WHMLUGIVZXSLKN-YIWLUXHESA-N (1s,3r)-3-(2-bromo-2-chloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C(O)C(Cl)(Br)C(F)(F)F)[C@@H]1C(O)=O WHMLUGIVZXSLKN-YIWLUXHESA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
GMWQNPAZOIIJSH-UHFFFAOYSA-N 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)C2C1C2(C)C GMWQNPAZOIIJSH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
239000013543 active substance Substances 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
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
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
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000013067 intermediate product Substances 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
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 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
230000037361 pathway Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 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
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)

NO980256A 1995-07-21 1998-01-20 Fremgangsmåte for fremstilling av syklopropankarboksylsyrer og mellomprodukter av disse NO309264B1 (no)

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.
PCT/DK1996/000326 WO1997003941A1 (en)	1995-07-21	1996-07-17	A process for the preparation of cyclopropane carboxylic acids and intermediates therefor

Publications (3)

Publication Number	Publication Date
NO980256L NO980256L (no)	1998-01-20
NO980256D0 NO980256D0 (no)	1998-01-20
NO309264B1 true NO309264B1 (no)	2001-01-08

Family

ID=8098295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO980256A NO309264B1 (no)	1995-07-21	1998-01-20	Fremgangsmåte for fremstilling av syklopropankarboksylsyrer og mellomprodukter av disse

Country Status (31)

Country	Link
US (1)	US5986130A (cs)
EP (1)	EP0842137B1 (cs)
JP (3)	JP3457005B2 (cs)
KR (1)	KR100284147B1 (cs)
CN (2)	CN1117061C (cs)
AR (2)	AR002899A1 (cs)
AT (1)	ATE191446T1 (cs)
BR (1)	BR9609740A (cs)
CA (1)	CA2224818C (cs)
CZ (1)	CZ293407B6 (cs)
DE (1)	DE69607627T2 (cs)
DK (2)	DK171797B1 (cs)
EA (1)	EA000683B1 (cs)
EE (1)	EE03521B1 (cs)
ES (1)	ES2145467T3 (cs)
GR (1)	GR3033832T3 (cs)
HU (1)	HU218983B (cs)
IL (2)	IL137108A (cs)
MX (1)	MX9800440A (cs)
NO (1)	NO309264B1 (cs)
NZ (1)	NZ313133A (cs)
PL (1)	PL182824B1 (cs)
PT (1)	PT842137E (cs)
RO (1)	RO117790B1 (cs)
SI (1)	SI0842137T1 (cs)
SK (1)	SK282494B6 (cs)
TR (1)	TR199800090T1 (cs)
TW (1)	TW339331B (cs)
UA (1)	UA59338C2 (cs)
WO (1)	WO1997003941A1 (cs)
ZA (1)	ZA965688B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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
AR097362A1 (es)	2013-08-16	2016-03-09	Cheminova As	Combinación de 2-metilbifenil-3-ilmetil (z)-(1r)-cis-3-(2-cloro-3,3,3-trifluorprop-1-enil)-2, 2-dimetilciclopropanocarboxilato con por lo menos un insecticida, acaricida, nematicida y/o fungicida

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 CN CN96196866A patent/CN1117061C/zh not_active Expired - Lifetime
- 1996-07-17 PT PT96924795T patent/PT842137E/pt unknown
- 1996-07-17 IL IL13710896A patent/IL137108A/xx not_active IP Right Cessation
- 1996-07-17 US US09/000,034 patent/US5986130A/en not_active Expired - Lifetime
- 1996-07-17 MX MX9800440A patent/MX9800440A/es unknown
- 1996-07-17 ES ES96924795T patent/ES2145467T3/es not_active Expired - Lifetime
- 1996-07-17 DK DK96924795T patent/DK0842137T3/da active
- 1996-07-17 IL IL12262496A patent/IL122624A/xx not_active IP Right Cessation
- 1996-07-17 DE DE69607627T patent/DE69607627T2/de not_active Expired - Lifetime
- 1996-07-17 KR KR1019980700441A patent/KR100284147B1/ko not_active Expired - Lifetime
- 1996-07-17 CN CNB021440948A patent/CN1258514C/zh not_active Expired - Lifetime
- 1996-07-17 AT AT96924795T patent/ATE191446T1/de active
- 1996-07-17 UA UA98010033A patent/UA59338C2/uk unknown
- 1996-07-17 CZ CZ1998186A patent/CZ293407B6/cs not_active IP Right Cessation
- 1996-07-17 SI SI9630194T patent/SI0842137T1/xx unknown
- 1996-07-17 NZ NZ313133A patent/NZ313133A/xx not_active IP Right Cessation
- 1996-07-17 HU HU9802288A patent/HU218983B/hu unknown
- 1996-07-17 TR TR1998/00090T patent/TR199800090T1/xx unknown
- 1996-07-17 BR BR9609740-0A patent/BR9609740A/pt not_active IP Right Cessation
- 1996-07-17 WO PCT/DK1996/000326 patent/WO1997003941A1/en not_active Ceased
- 1996-07-17 JP JP50618997A patent/JP3457005B2/ja not_active Expired - Lifetime
- 1996-07-17 EP EP96924795A patent/EP0842137B1/en not_active Expired - Lifetime
- 1996-07-17 RO RO98-00083A patent/RO117790B1/ro unknown
- 1996-07-17 EE EE9800019A patent/EE03521B1/xx not_active IP Right Cessation
- 1996-07-17 SK SK71-98A patent/SK282494B6/sk not_active IP Right Cessation
- 1996-07-17 CA CA002224818A patent/CA2224818C/en not_active Expired - Lifetime
- 1996-07-17 PL PL96324867A patent/PL182824B1/pl unknown
- 1996-07-17 EA EA199800143A patent/EA000683B1/ru not_active IP Right Cessation
- 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
2000
- 2000-06-30 GR GR20000401533T patent/GR3033832T3/el unknown
2001
- 2001-11-20 JP JP2001354657A patent/JP3807605B2/ja not_active Expired - Fee Related
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Publication number	Publication date
WO1997003941A1 (en)	1997-02-06
JP3457005B2 (ja)	2003-10-14
BR9609740A (pt)	1999-12-21
CA2224818C (en)	2008-02-26
NZ313133A (en)	1999-01-28
IL122624A0 (en)	1998-08-16
PT842137E (pt)	2000-09-29
PL182824B1 (pl)	2002-03-29
KR19990035782A (ko)	1999-05-25
JPH11509534A (ja)	1999-08-24
SK7198A3 (en)	1998-09-09
TR199800090T1 (xx)	1998-04-21
HUP9802288A2 (hu)	1999-01-28
NO980256L (no)	1998-01-20
EA199800143A1 (ru)	1998-08-27
UA59338C2 (uk)	2003-09-15
AR002899A1 (es)	1998-04-29
IL137108A (en)	2003-10-31
DE69607627T2 (de)	2000-07-27
CN1513829A (zh)	2004-07-21
NO980256D0 (no)	1998-01-20
CA2224818A1 (en)	1997-02-06
RO117790B1 (ro)	2002-07-30
CZ293407B6 (cs)	2004-04-14
AU6513696A (en)	1997-02-18
US5986130A (en)	1999-11-16
EE03521B1 (et)	2001-10-15
JP2002193879A (ja)	2002-07-10
CN1196043A (zh)	1998-10-14
EE9800019A (et)	1998-08-17
TW339331B (en)	1998-09-01
GR3033832T3 (en)	2000-10-31
EA000683B1 (ru)	2000-02-28
CN1258514C (zh)	2006-06-07
IL122624A (en)	2000-12-06
DK171797B1 (da)	1997-06-02
HK1015350A1 (zh)	1999-10-15
JP2002201188A (ja)	2002-07-16
HUP9802288A3 (en)	1999-03-01
JP3807605B2 (ja)	2006-08-09
MX9800440A (es)	1998-04-30
EP0842137A1 (en)	1998-05-20
DK85495A (da)	1997-01-22
HK1066210A1 (en)	2005-03-18
CN1117061C (zh)	2003-08-06
KR100284147B1 (ko)	2001-04-02
ZA965688B (en)	1997-01-24
AU701546B2 (en)	1999-01-28
EP0842137B1 (en)	2000-04-05
DK0842137T3 (da)	2000-09-04
ATE191446T1 (de)	2000-04-15
DE69607627D1 (de)	2000-05-11
HU218983B (hu)	2001-01-29
AR010461A2 (es)	2000-06-28
PL324867A1 (en)	1998-06-22
SK282494B6 (sk)	2002-02-05
CZ18698A3 (cs)	1998-06-17
SI0842137T1 (en)	2000-08-31
ES2145467T3 (es)	2000-07-01

Legal Events

Date	Code	Title	Description
2016-08-08	MK1K	Patent expired

Publication	Publication Date	Title
CA2224818C (en)	2008-02-26	A process for the preparation of cyclopropane carboxylic acids and intermediates therefor
US4479005A (en)	1984-10-23	Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids
EP0221635B1 (en)	1990-03-14	Fluoro alcohols and insecticidal esters thereof
MXPA98000440A (en)	1998-04-01	Procedure for the preparation of carboxilic and intermediary cyclopropan acids of the mis
AU701546C (en)	1999-10-14	A process for the preparation of cyclopropane carboxylic acids and intermediates therefor
US4258202A (en)	1981-03-24	Cyclopropanecarboxylic acids and esters
US4902835A (en)	1990-02-20	Fluorinated butene derivatives and methods for their preparation
CA1165770A (en)	1984-04-17	Process for stereoselectively synthetizing cyclopropane carboxylates as intermediates for pyrethroids
NO781113L (no)	1978-10-03	2-(2`,2`,2`-dihalogenvinyl)- og 2-(2`,2`,2`-trihalogenetyl)-cyklobutanon
US4255351A (en)	1981-03-10	Sulfonic acid esters of 2,2,2-trichloroethylhydroxycyclobutanones
US4211720A (en)	1980-07-08	Preparation of cyano-substituted cyclopropane derivatives
HK1066210B (en)	2007-01-19	A process for the preparation of cyclopropane carboxylic acids and its intermediates therefor
HK1015350B (en)	2004-04-23	Process for the preparation of cyclopropane carboxylic acid and intermediates therefor
US4515956A (en)	1985-05-07	Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids
HU201321B (en)	1990-10-28	Process for producing cyclopropane lactons
JPH05213823A (ja)	1993-08-24	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
DK161704B (da)	1991-08-05	Cyclopropancarboxylsyrelactonderivater og fremgangsmaader til fremstilling deraf
JPH07133270A (ja)	1995-05-23	クロマン誘導体およびその製法
GB2151625A (en)	1985-07-24	Process for the preparation of 3,5-ethano-2-2,4-dodecadienoates
JP2008094807A (ja)	2008-04-24	セダネノライドの製造方法
FR2555166A1 (fr)	1985-05-24	Procede de preparation de derives a-alkyles de l'acide acetique