Attractant for the mediterranean fruit fly, the method of preparation and method of use

• Main Authors: Raw, Andre S, Jang, Eric B
• Format: Patent
• Language: English
• Published: 23.04.2002

This invention relates to a method of attracting the Mediterranean fruit fly by subjecting the Mediterranean fruit fly to an attractant, wherein the attractant is ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate in an enantomeric excess of at least 70% and a regio and diastereo chemical purity of >5:1. The compound ethyl (1R,2R,5R)-5-iodo-2-methyl cyclohexane-1-carboxylate, in an enantomeric excess of at least 70% and a regio and diastereochemical purity of >5:1, may be prepared by reacting ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate with Ph P-imidazole-I (or Ph P-2,6-lutidine-I ) in a carbon tetrachloride/methlylene chloride mixture. A method of attracting the Mediterranean fruit fly by subjecting the Mediterranean fruit fly to an attractant, wherein the attractant is ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1. The compound ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate, in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1, may be stereoselectively synthesized on a multigram scale in 15% yield by reacting ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate with PhP-imidazole-I(or PhP-2,6-lutidine-I) in a carbon tetrachloride/methlylene chloride mixture. The 1R,2R,5R enantiomer is significantly more attractive than its enantiomeric counterpart (1S,2S,5S), or either of the commercial products trimedlure or ceralure, each a mixture of 16 regio and stereoisomers.