DK174092B1 - Fremgangsmåde til fremstilling af en blanding af enantiomerpar af permethrinsyre-alfa-cyano-3-phenoxy-4-fluor-benzylester - Google Patents

Fremgangsmåde til fremstilling af en blanding af enantiomerpar af permethrinsyre-alfa-cyano-3-phenoxy-4-fluor-benzylester Download PDF

Info

Publication number: DK174092B1
Authority: DK; Denmark
Prior art keywords: mixture; cyano; phenoxy; preparing; fluoro
Prior art date: 1985-06-25

Application number

DK198602963A

Other languages

Danish (da)

English (en)

Other versions

DK296386A (da

DK296386D0 (da

Inventor

Rainer Fuchs

Andreas Wittig

Original Assignee

Bayer Ag

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.)

1985-06-25

Filing date

1986-06-24

Publication date

2002-06-10

1986-06-24 Application filed by Bayer Ag filed Critical Bayer Ag

1986-06-24 Publication of DK296386D0 publication Critical patent/DK296386D0/da

1986-12-26 Publication of DK296386A publication Critical patent/DK296386A/da

2002-06-10 Application granted granted Critical

2002-06-10 Publication of DK174092B1 publication Critical patent/DK174092B1/da

Links

239000000203 mixture Substances 0.000 title claims description 25
-1 permethric acid alpha-cyano-3-phenoxy-4-fluoro-benzyl ester Chemical class 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title claims description 3
238000000034 method Methods 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
150000003335 secondary amines Chemical class 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 10
239000002904 solvent Substances 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000006345 epimerization reaction Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
IFEMCSICGXTDGN-UHFFFAOYSA-N 1-[cyano-(3-phenoxyphenyl)methyl]-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1(C(O)=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 IFEMCSICGXTDGN-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
102000016726 Coat Protein Complex I Human genes 0.000 description 1
108010092897 Coat Protein Complex I Proteins 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical group [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK198602963A 1985-06-25 1986-06-24 Fremgangsmåde til fremstilling af en blanding af enantiomerpar af permethrinsyre-alfa-cyano-3-phenoxy-4-fluor-benzylester DK174092B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19853522629 DE3522629A1 (de)	1985-06-25	1985-06-25	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester
DE3522629		1985-06-25

Publications (3)

Publication Number	Publication Date
DK296386D0 DK296386D0 (da)	1986-06-24
DK296386A DK296386A (da)	1986-12-26
DK174092B1 true DK174092B1 (da)	2002-06-10

Family

ID=6274089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198602963A DK174092B1 (da)	1985-06-25	1986-06-24	Fremgangsmåde til fremstilling af en blanding af enantiomerpar af permethrinsyre-alfa-cyano-3-phenoxy-4-fluor-benzylester

Country Status (25)

Country	Link
US (1)	US4782174A (pt)
EP (1)	EP0206149B1 (pt)
JP (1)	JPH0676368B2 (pt)
KR (1)	KR940010763B1 (pt)
CN (1)	CN1009273B (pt)
AR (1)	AR247727A1 (pt)
AT (1)	ATE45728T1 (pt)
AU (1)	AU574924B2 (pt)
BR (1)	BR8602915A (pt)
CA (1)	CA1280763C (pt)
DD (1)	DD251549A5 (pt)
DE (2)	DE3522629A1 (pt)
DK (1)	DK174092B1 (pt)
EG (1)	EG18080A (pt)
ES (1)	ES8707178A1 (pt)
GR (1)	GR861632B (pt)
HU (1)	HU202833B (pt)
IE (1)	IE58563B1 (pt)
IL (1)	IL79197A (pt)
NZ (1)	NZ216623A (pt)
PH (1)	PH22399A (pt)
PL (1)	PL146571B1 (pt)
PT (1)	PT82770B (pt)
TR (1)	TR22455A (pt)
ZA (1)	ZA864705B (pt)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3522629A1 (de) *	1985-06-25	1987-01-08	Bayer Ag	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester
US4997970A (en) *	1987-06-15	1991-03-05	Fmc Corporation	Conversion of pyrethroid isomers to move active species
EP0404922B1 (en) *	1989-01-17	1993-06-09	CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT.	Process for the preparation of cypermethrine isomers
US5128497A (en) *	1990-01-03	1992-07-07	Fmc Corporation	Conversion of pyrethroid isomers to more active species
DE4216535A1 (de) *	1991-08-21	1993-02-25	Bayer Ag	Formkoerper zur bekaempfung von schaedlingen
DE19953775A1 (de)	1999-11-09	2001-05-10	Bayer Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
DE10007411A1 (de) *	2000-02-18	2001-08-23	Bayer Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
AR029677A1 (es) *	2000-06-29	2003-07-10	Bayer Ag	Combinaciones de compuestos activos con propiedades insecticidas y acaricidas
DE10203688A1 (de)	2002-01-31	2003-08-07	Bayer Cropscience Ag	Synergistische insektizide Mischungen
DE10207241A1 (de) *	2002-02-21	2003-09-04	Bayer Cropscience Ag	Synergistische insektizide Mischungen
GB0229803D0 (en) †	2002-12-20	2003-01-29	Syngenta Ltd	Chemical process
DE102004001271A1 (de) *	2004-01-08	2005-08-04	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden Eigenschaften
US20090281157A1 (en) *	2006-07-11	2009-11-12	Bayer Cropscience Ag	Active Ingredient Combinations With Insecticidal and Acaricidal Properties
DE102006046688B3 (de) *	2006-09-29	2008-01-24	Siemens Ag	Kälteanlage mit einem warmen und einem kalten Verbindungselement und einem mit den Verbindungselementen verbundenen Wärmerohr
WO2008037379A1 (de) *	2006-09-30	2008-04-03	Bayer Cropscience Aktiengesellschaft	Suspensionskonzentrate zur verbesserung der wurzelaufnahme von agrochemischen wirkstoffen
DE102007045953B4 (de)	2007-09-26	2018-07-05	Bayer Intellectual Property Gmbh	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
NZ589018A (en) *	2008-05-07	2012-07-27	Bayer Cropscience Ag	Synergistic active ingredient combinations
EP2127522A1 (de)	2008-05-29	2009-12-02	Bayer CropScience AG	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
EP2227951A1 (de)	2009-01-23	2010-09-15	Bayer CropScience AG	Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren
WO2010108505A1 (de)	2009-03-25	2010-09-30	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften
BR122020019020B1 (pt)	2009-03-25	2021-05-04	Bayer Cropscience Aktiengesellschaft	Combinação de substância ativa nematicida, seus usos, composição e seu processo de produção, semente resistente a pestes, e método para combate de pestes animais
DE102009028001A1 (de)	2009-07-24	2011-01-27	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
EP2382865A1 (de)	2010-04-28	2011-11-02	Bayer CropScience AG	Synergistische Wirkstoffkombinationen
EP2446742A1 (de)	2010-10-28	2012-05-02	Bayer CropScience AG	Insektizide oder akarizide Zusammensetzungen enthaltend Mono- oder Disacchariden als Wirkungsverstärker
CN105997976A (zh) *	2016-05-09	2016-10-12	黄中心	一种治疗蛀牙的组合物

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2375161A1 (fr) *	1976-04-23	1978-07-21	Roussel Uclaf	Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)
JPS5657756A (en) *	1979-10-15	1981-05-20	Sumitomo Chem Co Ltd	Preparation of more highly active carboxylic ester
CA1150301A (en) *	1979-11-27	1983-07-19	Michael J. Bull	Cyclopropane carboxylic acid ester derivatives
GB2128607A (en) *	1982-10-18	1984-05-02	Ici Plc	An enantiomeric pair of cyhalothrin isomers and process for preparation thereof
DE3401483A1 (de) *	1984-01-18	1985-07-25	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl-ester
GB8418331D0 (en) *	1984-07-18	1984-08-22	Ici Plc	Insecticidal ester
CA1275108A (en) *	1985-01-16	1990-10-09	Laszlo Pap	Insecticidal composition comprising more than one active ingredients
DE3522629A1 (de) *	1985-06-25	1987-01-08	Bayer Ag	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester

1985
- 1985-06-25 DE DE19853522629 patent/DE3522629A1/de not_active Withdrawn
1986
- 1986-06-12 EP EP86108037A patent/EP0206149B1/de not_active Expired
- 1986-06-12 AT AT86108037T patent/ATE45728T1/de not_active IP Right Cessation
- 1986-06-12 DE DE8686108037T patent/DE3665170D1/de not_active Expired
- 1986-06-16 US US06/874,989 patent/US4782174A/en not_active Expired - Lifetime
- 1986-06-16 PT PT82770A patent/PT82770B/pt unknown
- 1986-06-19 JP JP61141527A patent/JPH0676368B2/ja not_active Expired - Fee Related
- 1986-06-20 AU AU59127/86A patent/AU574924B2/en not_active Ceased
- 1986-06-22 EG EG37986A patent/EG18080A/xx active
- 1986-06-23 ZA ZA864705A patent/ZA864705B/xx unknown
- 1986-06-23 CN CN86104832A patent/CN1009273B/zh not_active Expired
- 1986-06-23 DD DD86291571A patent/DD251549A5/de not_active IP Right Cessation
- 1986-06-23 NZ NZ216623A patent/NZ216623A/xx unknown
- 1986-06-23 IL IL79197A patent/IL79197A/xx not_active IP Right Cessation
- 1986-06-23 CA CA000512143A patent/CA1280763C/en not_active Expired - Lifetime
- 1986-06-24 ES ES556533A patent/ES8707178A1/es not_active Expired
- 1986-06-24 IE IE168686A patent/IE58563B1/en not_active IP Right Cessation
- 1986-06-24 GR GR861632A patent/GR861632B/el unknown
- 1986-06-24 KR KR1019860005043A patent/KR940010763B1/ko not_active Expired - Fee Related
- 1986-06-24 PL PL1986260245A patent/PL146571B1/pl unknown
- 1986-06-24 TR TR29639/86A patent/TR22455A/xx unknown
- 1986-06-24 BR BR8602915A patent/BR8602915A/pt not_active IP Right Cessation
- 1986-06-24 DK DK198602963A patent/DK174092B1/da not_active IP Right Cessation
- 1986-06-25 PH PH33942A patent/PH22399A/en unknown
- 1986-06-25 AR AR86304358A patent/AR247727A1/es active
- 1986-06-25 HU HU862658A patent/HU202833B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA1280763C (en)	1991-02-26
HUT42051A (en)	1987-06-29
PT82770A (en)	1986-07-01
KR870000287A (ko)	1987-02-17
IL79197A0 (en)	1986-09-30
ATE45728T1 (de)	1989-09-15
JPH0676368B2 (ja)	1994-09-28
CN86104832A (zh)	1986-12-31
EP0206149A3 (en)	1987-05-13
ZA864705B (en)	1987-02-25
TR22455A (tr)	1987-07-13
US4782174A (en)	1988-11-01
EP0206149B1 (de)	1989-08-23
AR247727A1 (es)	1995-03-31
NZ216623A (en)	1989-01-27
GR861632B (en)	1986-10-20
PT82770B (pt)	1988-12-15
JPS62456A (ja)	1987-01-06
IE58563B1 (en)	1993-10-06
AU574924B2 (en)	1988-07-14
KR940010763B1 (ko)	1994-11-11
DK296386A (da)	1986-12-26
IL79197A (en)	1990-06-10
ES556533A0 (es)	1987-07-16
BR8602915A (pt)	1987-02-17
EP0206149A2 (de)	1986-12-30
HU202833B (en)	1991-04-29
PH22399A (en)	1988-08-26
CN1009273B (zh)	1990-08-22
ES8707178A1 (es)	1987-07-16
DE3665170D1 (en)	1989-09-28
PL146571B1 (en)	1989-02-28
DD251549A5 (de)	1987-11-18
DE3522629A1 (de)	1987-01-08
DK296386D0 (da)	1986-06-24
AU5912786A (en)	1987-01-08
EG18080A (en)	1994-07-30
IE861686L (en)	1986-12-25

Publication	Publication Date	Title
DK174092B1 (da)	2002-06-10	Fremgangsmåde til fremstilling af en blanding af enantiomerpar af permethrinsyre-alfa-cyano-3-phenoxy-4-fluor-benzylester
DE60009407T2 (de)	2005-03-03	Verfahren zur Herstellung von N-carbamat-geschütztem beta-Aminoepoxid und beta-Aminoalkohol
DK173881B1 (da)	2002-01-28	Fremgangsmåde til fremstilling af enantiomerparrene (1R-3R-alfaS + 1S-3S-alfaR) og (1R-3S-alfaS + 1S-3R-alfaR) ud fra blandingen af alle 8 stereoisomere af forbindelsen R/S-cyano-3-phenoxy-4-fluorbenzyl-3R/S-(2,2-dichlorvinyl)-2,2-dimethyl-1R/S-
JPS59101452A (ja)	1984-06-12	シクロプロパンカルボン酸エステル誘導体の製造法
FR2470117A1 (fr)	1981-05-29	Derives d'esters d'acides cyclopropanecarboxyliques, leur preparation et leur application comme pesticides
US4427598A (en)	1984-01-24	Process for preparing cyclopropane carboxylic acid ester derivatives
US4436667A (en)	1984-03-13	Process for preparing cyclopropane carboxylic acid ester derivatives
FI114465B (fi)	2004-10-29	Menetelmä pyretroidi-insektisidiyhdisteen aikaansaamiseksi
KR850001176B1 (ko)	1985-08-19	시클로프로판 카르복시산 에스테르유도체 제조방법
GB2075011A (en)	1981-11-11	Process for Preparing Cyclopropane Carboxylic Acid Ester Derivatives
CS257291B2 (cs)	1988-04-15	Způsob výroby směsi párů enantiomerů a-kyan-3-fenoxy-4-fluorbenzylesteru permethrinové kyseliny
ES2020789A6 (es)	1991-09-16	Procedimiento de resolucion de intermedios utiles para la preparacion de diltiazem.
KR850001178B1 (ko)	1985-08-19	시클로프로판 카르복실산 에스테르 유도체의 제조방법
GB2074573A (en)	1981-11-04	Process for Preparing Cyclopropane Carboxylic Acid Ester Derivatives

Legal Events

Date	Code	Title	Description
2002-06-10	B1	Patent granted (law 1993)
2006-03-06	PBP	Patent lapsed	Country of ref document: DK