Insect pheromones from olefin metathesis

Abstract

The cross-metathesis of simple olefins with olefinic esters is a convenient method of preparing many insect pheromone chemicals or precursors. Insect pheromones represent a new, safe method of controlling insect pest populations. The stereochemistry of cross-metathesis products is the critical factor in determining the applicability of metathesis pheromones to insect control. A number of olefinic esters and simple olefins have been reacted with one another using homogeneous catalysts based upon Fischer-type carbene complexes. Careful determination of cross-product stereochemistry indicated that partial control of the product isomer content is possible. Field tests of these metathesis mixtures indicate that, in certain cases, these mixtures can be used to control insect pests. © 1985.