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Home Vasodialators Cyclopropane-carboxylic-acid-derivatives

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 Cyclopropane carboxylic acid derivatives

Details
Inventors: Tessier, Jean; Demoute, Jean-Pierre; Cadiergue, Joseph;
Assignee: Roussel Uclaf (Paris, FR)
Primary Examiner:
Assistant Examiner:
Attorney, Agent or Firm:

All stereoisomeric forms and mixtures of stereoisomers of compounds of the formula ##STR1## wherein X is selected from the group consisting of oxygen, sulfur, sulfoxide and sulfone, R.sub.1 and R.sub.3 are individually selected from the group consisting of optionally unsaturated alkyl of 1 to 7 carbon atoms and optionally unsaturated cycloalkyl of 3 to 7 carbon atoms optionally substituted with at least one halogen and optionally interrupted with at least one heteroatom and aryl and aralkyl of 6 to 18 carbon atoms and R.sub.2 is the residue of a R.sub.2 OH alcohol used in pyrethrinoids synthesis having pesticidal activity and their preparation and novel intermediates.

DETAILED DESCRIPTION What we claim is: 1.
A compound selected from the group consisting of all stereoisomer forms and mixtures of stereoisomers of compounds of the formula ##STR25## wherein X is selected from the group consisting of oxygen, sulfur, sulfoxide and sulfone, R.
sub.
1 and R.
sub.
3 are individually selected from the group consisting of alkyl of 1 to 7 carbon atoms, alkenyl and alkadienyl of 2 to 7 carbon atoms and cycloalkyl and cycloalkenyl of 3 to 7 carbon atoms optionally substituted with at least one halogen and optionally interrupted with at least one heteroatom and aryl and aralkyl of 6 to 18 carbon atoms and R.
sub.
2 is selected from the group consisting of ##STR26## 2.
A compound of claim 1 wherein X is oxygen.
3.
A compound of claim 1 wherein X is sulfur.
4.
A compound of claim 1 selected from the group consisting of (S).
alpha.
-cyano-3-phenoxy-benzyl (1R,trans,.
DELTA.
Z) 2,2-dimethyl-3-dimethyl-3-[2-methoxy-2-methoxycarbonyl-ethenyl]-cyclopropa ne-carboxylate, (S).
alpha.
-cyano-3-phenoxy-benzyl (1R,trans,.
DELTA.
Z) 2,2-dimethyl-3-[2-methoxy-2-methoxycarbonyl-ethenyl]-cyclopropane-carboxyl ate, 3-allyl-2-methyl-4-oxo-2-cyclopenten-1-yl (1R,trans,.
DELTA.
Z) 2,2-dimethyl-3-[2-methoxy-2-methoxycarbonyl-ethenyl]-cyclopropane-carboxyl ate, 3-alkyl-2-methyl-4-oxo-2-cyclopenten-1-yl (1R, trans,.
DELTA.
E) 2,2-dimethyl-3-[2-methoxy-2-methoxycarbonyl-ethenyl]-cyclopropane-carboxyl ate, [1-(3-propyn-2-yl)-2,5-dioxo-imidazolidinyl]-methyl (1R,trans,.
DELTA.
Z) 2,2-dimethyl-3-[2-methoxy-2-methoxycarbonyl-ethenyl]-c yclopropane-carboxylate, (S).
alpha.
-cyano-3-phenoxy-4-fluoro-benzyl (1R, trans,.
DELTA.
Z or .
DELTA.
E) 2,2-dimethyl-3-[2-methoxy-2methoxycarbonyl-ethenyl]-cyclopropane-carboxyla te, (R,S).
alpha.
-cyano-6'-phenoxy-2'-pyridyl-methyl (1R,trans,.
DELTA.
Z or .
DELTA.
E) 2,2-dimethyl -3-[2-methoxy-2-methoxycarbonyl-ethenyl]-cyclopropane-carboxylate, (S).
alpha.
-cyano-3-phenoxy-benzyl (1R,trans,.
DELTA.
Z) 2,2-dimethyl-3-[2-methoxy-2-ethoxycarbonyl-ethenyl]-cyclopropane-carboxyla te, (S).
alpha.
-cyano-3-phenoxy-benzyl (1R,trans,



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