Cost Effective Pheromone Production Using Novel Synthetic Routes

Currently, many thousands of tons of pesticides are used annually to control agricultural pests. These general purpose non species specific agents have many drawbacks including negative impacts on human health and ecosystem damage. This work’s purpose was to investigate if previously characterised pheromones of pest insect species could be synthesised in a simpler manner for use as a more sustainable form of pest control. Attempts were made to synthesise three pheromone chemicals. The first of these was 12-dodecanolide via the Baeyer-Villiger oxidation of cyclododecanone as the saturated analogue of (3Z)-dodecen-12-olide. The unsaturated chemical is secreted by the female Emerald-ash borer. An attempt to synthesise (Z,E)-7,9,11-dodecatrienyl formate, a mimic of the major sex pheromone of the Carob moth was made using a convergent three-step synthesis. The current method uses seven steps. Finally, (2S,12Z)-2-acetoxy-12-heptadecene, the female secreted pheromone of the pistachio twig borer was attempted by replication of a recent patent. The methods were arrived at by use of Scifinder-n, a synthesis aiding computer package and more conventional literature searching. The synthesis of 12-dodecanolide was a success and the product was trialled successfully by the partner company, IPS in Birkenhead. The synthesis of (2S,12Z)-2-acetoxy-12-heptadecene was a partial success but had to be abandoned due to time constraints. The synthesis of (Z,E)-7,9,11-dodecatrienyl formate was attempted using different methods but did not yield any useful product.