Submitted to: Book Chapter
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: June 14, 2004
Publication Date: July 11, 2005
Citation: Petroski, R.J., Cosse, A.A., Bartelt, R.J., Zilkowski, B.W. 2005. Practical syntheses of selected insect pheromones. In: Petroski, R.J., Tellez, M.R., Behle, R.W., editors. Semiochemicals in Pest and Weed Control. American Chemical Society, Washington, DC. p. 29-43. Interpretive Summary: There is a continuing need to develop more efficient pest and weed control strategies. The use of insect pheromones has become an important part of the process because of cost savings and selectivity. Difficulties occur when the chemical synthesis of the pheromone substances is lengthy or expensive. This paper describes the use of standard methods to produce certain insect pheromones for agricultural use. These results are important to scientists, especially those in industry, because synthetic pathways must be capable of scale-up in order to be viable for commercial production.
Technical Abstract: Practical examples of several insect pheromone syntheses are presented. Examples of key reactions in synthetic pathways include: kinetic versus thermodynamic control of cycloheptanone dimethylation (flea beetles), in situ oxidation/Wittig olefination (salt cedar leaf beetle), preparation of a 1,4-diol using a four-carbon homologating agent (currant stem girdler), preparation of trisubstituted alkenoic acids (cowpea weevil), and regiospecific epoxidation followed by cleavage of the epoxide to form a key aldehyde intermediate (cereal leaf beetle).