Sex pheromones produced by male boll weevil: isolation, identification, and synthesis.

The response of female boll weevils to males, Anthonomus grandis Boheman, in laboratory bioassays can be reproduced by exposure to a mixture of compounds I, II, and either III or IV, all isolated from male weevils and their fecal material. The same response was elicited by mixtures of tile synthesized coimpounds. Compound I is (+)-cis-2-isopropenyl-l-methylcyclobtutaneethanol; II, cis-3,3-dimethiyl->(1,beta)cyclohexaneethanol; III, cis-3,3-dimethlyl->(1,alpha)-cyclohexaneacetaldehyde; and IV, trans-3,3-dimethyl->(1,alpha)-cyclohexanecetaldehyde.