Structure-activity relationships among aromatic analogs of trail-following pheromone of subterranean termites

A series of 12 substituted (Z)-4-phenyl-3-buten-l-ol (PBO) derivatives were synthesized and evaluated for trail-following activity in five species of subterranean termites in the generaCoptotermes, Prorhinotermes, Reticulitermes, andSchedorhinotermes (Isoptera: Rhinotermitidae). The unsubstituted parent PBO was the most active for all species, and electron-withdrawing and electron-donating groups both reduced potency. Sensitivity to substitution in the ortho position suggests steric inhibition of binding by the 2-substituted analogs. Different sensitivities to these pheromone analogs were found among the five species, withR.flavipes andS. lamanianus showing the highest level of trail-following activity for the PBO analogs.Fellow of the Alfred P. Sloan Foundation (1981–85) and Camille and Henry Dreyfus Teacher-Scholar (1981–86).