| The goal of this research was to prepare sufficient amounts of pheromone compounds for the development and formulation of integrated pest management (IPM) methods. These IPM methods included "attract and kill" and mating disruption. Insect pheromone components for five different insect species were synthesized. The preparation of 9E,11Z-hexadecadienal, the major sex pheromone component of the pecan nut casebearer, Acrobasis nuxvorella (Neunzig), is described in the second chapter. The major pheromone component was produced using two different synthetic pathways. The second pathway allowed for the preparation of significant quantities of material that were later incorporated into both mating disruption and "attract and kill" experiments. Synthesis of a structurally similar compound, 5E,7Z-dodecadien-1-ol and the corresponding aldehyde, the sex pheromone components of the eastern tent caterpillar, Malacasoma americanum, are summarized in the third chapter. Using a similar synthetic procedure, gram quantities of the pheromone components were easily generated. The synthesis of the A1 sex pheromone component, 6-isopropenyl-3-methyl-9-decenyl acetate, of the California red scale, Aonidiella aurantii, is summarized in the fourth chapter. Within six steps, significant amounts of the major sex pheromone component could be obtained. In the fifth chapter, two short routes to prepare (1R)-(+)-cis-2,2-dimethyl-3-isopropenylcyclobutane methanol acetate, the sex pheromone of the citrus mealybug, Planococcus citri (Risso), are described. Again, the second route afforded sufficient amounts of material that was effectively formulated for mating disruption. The synthesis of the sex pheromone mimic of the carob moth, Ectomyelois ceratoniae, 7Z,9E,11-dodecatrienyl formate, is summarized in the sixth chapter. Unfortunately, only small amounts of the mimic were collected due to the tedious purifications necessary. All sex pheromone components prepared were characterized using GC/FID and NMR (1H and 13C). |
