Síntese régio e estereosseletiva do feromônio sexual e isômero geométrico da mariposa Telchin licus licus (Leptoptera: Castaniidae)

Abstract

The importance of sugarcane culture in Brazil is analyzed in this work, aiming at its social, economic and environmental aspects. More specifically, the culture damages caused by the giant sugarcane borer, Telchin licus licus, are presented, along with the current methods of field control of this problem and the importance of pheromones use in the integrated pest management. It is also shown the main types of reactions involved in the synthesis of pheromones of Lepidoptera, with emphasis on preparing regio-stereoselective reactions with double bonds. The first synthesis of 3, 13-octadecadien-1-ol by other synthetic route is presented. Finally, is shown the regio-stereospecific synthesis of (3E, 13Z)-octadecadien-1-ol (1) and its stereoisomer (3Z, 13Z)-octadecadien-1-ol (2), the likely constituents of the sex pheromone of the moth Telchin licus licus Drury, 1773 (Lepidoptera: Castniidae). The presented short synthetic routes starts with same raw materials. In four steps and a unique way, the reactions achieved 26% and 56% overall yield, respectively. Thus, the work concludes exhibiting an alternative to minimize losses and increase agricultural productivity of the sugar and alcohol industry with the use of synthetic pheromones on the monitoring and pest control.