# US 4,400,523 A · Process for the preparation of styryl-cyclopropanecarboxylic acid esters and new intermediate products for this process

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- Number: US 4,400,523 A
- Document ID: US4400523A
- Status: Granted
- Kind: A
- Application number: 06/319,768
- Filed: 1981-11-09
- Granted: 1983-08-23
- Earliest claimed: 1979-04-23
- Assignees: Bayer Aktiengesellschaft
- Inventors: Manfred Jautelat; Dieter Arlt; Reinhard Lantzsch; Rainer Fuchs; Hans-Jochem Riebel; Rolf Schroder; Horst Harnisch
- Web page: https://patentgrep.com/patent/US4400523A

## CPC

- C07D 307/33: in position 2, the oxygen atom being in its keto or unsubstituted enol form
- A01N 53/00: Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C07C 59/64: containing six-membered aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for the preparation of a styryl-cyclopropane-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids, R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen, R.sup.2 is hydrogen or alkoxy, or R.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, and R.sup.3 is hydrogen or chlorine, comprising reacting a compound of the formula ##STR2## with, respectively, one, two or three equivalents of a base at a temperature below 60.degree. C. The products are insecticidally active when R is the residue of a pyrethroid-type alcohol. Various syntheses are given for the starting materials which are new.

## Claims

### Claim 1

A compound of the formula ##STR34## in which R.sup.1 is C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.2 -fluoroalkoxy, C.sub.1 -C.sub.2 -chlorofluoroalkoxy or C.sub.1 -C.sub.2 -fluoroalkylthio, and
R.sup.2 is hydrogen or methoxy or, together with R.sup.1, C.sub.1 -C.sub.2 -alkylenedioxy or C.sub.1 -C.sub.2 -fluoroalkylenedioxy.