Síntese de substâncias candidatas a feromônios de lepidópteros pragas

Abstract

Agriculture has great importance in the Brazilian economy and the presence of pests has caused great economic losses for producers of the most diverse crops in Brazil. One of them is Telchin licus, a pest that causes losses of sugar cane production in all regions where it is present. Andiroba is a tree with high potential for exploration, from its seeds an oil widely used in cosmetics and popular medicine in the Amazon region is extracted and it has also suffered from the presence of pests, especially Hypsipyla ferrealis, which attacks the seed, making its use impracticable. In oil palm and coconut crops, defoliating caterpillars cause problems and the attack mainly by Automeris liberia has been causing damage to the arecaceae crops. As the use of pesticides can be harmful to health, the use of pheromones has become possible due to its great selectivity and low toxicity. To enable the use of pheromones for these pests, the aim of the work is to synthesize (Z,E)-2,13-octadecadien-1-ol and (E,Z)-2,13-octadecadien-1-ol isomers, (Z,E)-9,12-tetradecadien-1-ol, (E,Z)-9,12-tetradecadien-1-ol, (Z,Z)-9,12-tetradecadien-1-ol and (E,E)-9,12-tetradecadien-1-ol isomers and (±)-9-methylnonadecane which are candidates for pheromones of these species respectively. The syntheses have shown good individual yields and the compounds obtained have been characterized by hydrogen and carbon NMR, GC-MS and also by Infrared. From structures proposed in the work, (±)-9-methylnonadecane was synthesized with an overall yield of 51.4%, while (E,Z)-2,13-octadecadien-1-ol was synthesized with an overall yield of 12.5%. Were also synthesized 10-pentadecyn-1-ol, intermediate of (Z,E)-2,13-octadecadien-1-ol and the two isomers of tetradec-12-en-9-in-1-ol, which are intermediates for the formation of the 9,12-tetradecadien-1-ol isomers.