Synthesis and biological activity of point-fluorinated pheromone analogues of Eldana saccharina

Substitution of fluorine atoms on an organic molecule makes it possible to modify the molecular orbital and electron density of the surface without changing its molecular shape. Point-fluorinated analogues of the sex pheromone of the male African sugarcane borer were synthesized in optically active forms and their pheromone activities were investigated using an EAG test. The EAG activity of these point-fluorinated pheromone analogues indicates that the point of fluorination has a critical influence on the pheromone activity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).