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Cyclopropane carboxylic acid derivatives
| Details |
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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. |
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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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