Ecdysones and analogs: effects on development and reproduction of insects.

Ingestion of certain synthetic ecdysone analogs inhibited larval growth and development in several species of insects, whereas 20-hydroxyecdysone was inactive or considerably less active. Natural 20-hydroxyecdysone and ponasterone A, and a synthetic ecdysone analog inhibited ovarian maturation and egg production in the adult housefly. These effects appeared to be related to hormonal activity.

Utilization and metabolism of dietary sterols in the honey bee and the yellow fever mosquito.

The honey bee, Apis mellifera, does not convert C28 and C29 phytosterols to cholesterol as found in most previous studies of phytophagous or omnivorous insects, but instead the workers and queens selectively transfer 24-methylenecholesterol, sitosterol and isofucosterol from their endogenous sterol pools to the brood larvae regardless of the sterol in the worker diet. Administering radiolabeled sterols by feeding and injection has made it possible to trace this selective transfer through a second generation of the honey bee. In further comparative sterol metabolism studies, the yellow fever mosquito, Aedes aegypti, was shown to be capable of dealkylating and converting a radiolabeled C29 dietary sterol ([14C]sitosterol) to cholesterol. Metabolic studies with several radiolabeled dietary sterols and an inhibitor of steroid metabolism in the yellow fever mosquito further verified this capability.

Nonsteroidal secondary and tertiary amines: inhibitors of insect development and metamorphosis and delta-24-sterol reductase system of tobacco hornworm.

Several new branched and straight chain secondary and tertiary amines were shown to have inhibitive effects upon development and metamorphosis and the delta-24-sterol reductase system in larvae of the tobacco hornworm similar to those previously observed with a number of azasteroids. Certain of the amines which are related structurally to compounds with juvenile hormone activity in insects also blocked development and metamorphosis in three other species of insects. These compounds are lethal or inhibit development in all larval stages and thus differ in action from compounds with juvenile hormone activity where the principal effect is to block the penultimate or ultimate molt.

Inhibitive effects of structurally modified azasteroids and related nitrogen containing steroids on insect growth and development.

A number of azasteroids and other nitrogen containing steroids with a modified nucleus or side chain were prepared and tested for their inhibitory effects on the growth and development of several species of insects. Structure-activity studies showed that compounds with a structurally related steroid nucleus and side chain were approximately equal in inhibitory activity for a particular species. The replacement of the tertiary amino group in the side chain of the 5beta-steroid with other nitrogen substituents, such as nitro, cyano, acetylamino, or a quaternary ammonium salt, resulted in a considerable loss of inhibitive activity in the tobacco hornworm or the yellowfever mosquito. However, certain modifications of the azasteroid nucleus resulted in compounds that still retained high biological activity. As a result, a compound was synthesized that lacked the A and B rings of the steroid nucleus and that inhibited insect growth, molting, and metamorphosis and the delta24-sterol reductase enzyme system of the tobacco hornworm.