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Inhibitive effects of structurally modified azasteroids and related nitrogen containing steroids on insect growth and development
Author(s) -
Thompson M. J.,
Serban N. N.,
Robbins W. E.,
Svoboda J. A.,
Shortino T. J.,
Dutky S. R.,
Cohen C. F.
Publication year - 1975
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532726
Subject(s) - lipidology , chemistry , insect , nitrogen , clinical chemistry , biology , organic chemistry , botany , biochemistry
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 5β‐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 Δ 24 ‐sterol reductase enzyme system of the tobacco hornworm.