A Convenient Method for the Preparation of Pheromones from Inexpensive Starting Materials

Many aliphatic compounds having 12, 14, or 16 carbon atoms and one or two double bonds are known to function as “chemical messengers” be­ tween different sexes of the same insect species [1]. Saturation of a mating area with high concentrations of such a “pheromone” may be used to inhibit olfactory orientation between sexes. Moreover, by using sex attractant pheromones, certain insects may be drawn into traps. Hence, pheromones can be used for the biological control of insect pests [1]. The preparation of sex attractants by chemical synthesis is tedious, mainly because o f the difficulties encountered in separating the mixtures of (Z)and (£)-isomers formed. (Z)-9-Tetradecenol, for exam­ ple, the sex pheromone of the fall army worm (.Laphygma frugiperda) can be obtained together with the (£)-isomer by a Wittig synthesis; the desired (Z)-9-tetradecenol must be isolated by chromatography [2], We have found beef tallow and fats from slaugh­ tering wastes to be excellent raw materials for the isolation of (Z)-9-tetradecenoic acid. The aim of the present work was the isolation of this acid in high purity, and the preparation of the corresponding alcohol, alkyl acetate and aldehyde, derivatives, which can serve as pheromones for the control of a variety of insects. In view of the abundance and the low cost of the starting material, the process described can be con­