Studies on relationship between activity and electron density on carbonyl oxygen in sex pheromone mimics of the American cockroach,part XI

From the relationship between structures of the 2-substituents of verbanyl analogs and their sex pheromone activities to the American cockroach, electron density of the carbonyl oxygen atom in the substituent, as estimated by the [¹⁷O]NMR chemical shift, was estimated to be an important factor which influenced the activity, in addition to length of the substituent and the position of the carbonyl group. (+)-Verbanyl methylcarbonate (XX), possessing the highest electron density on the carbonyl oxygen atom, showed the strongest activity among the analogs.For Part X, see Manabe et al., 1983. J. Chem. Ecol. 9:533–549.