2-Acetylpyridine thiosemicarbazones as inhibitors of ecdysis in Oncopeltus fasciatus: structure-activity relationship study

Effects of structural variations of (1-(2-pyridinyl)ethylidene)hydrazide of 1-pyrrolidinecarbothioic acid (23) on ecdysis of Oncopeltus fasciatus were examined in 50 related compounds. Marked ecdysis-inhibiting effects were elicited by substituted thiosemicarbazones of 2-acetyl-, 2-propionyl-, and 2...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1983-07, Vol.31 (4), p.713-718
Main Authors: DeMilo, Albert B, Redfern, Robert E, Borkovec, Alexej B
Format: Article
Language:English
Subjects:
Lygaeidae
Oncopeltus fasciatus
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Summary:Effects of structural variations of (1-(2-pyridinyl)ethylidene)hydrazide of 1-pyrrolidinecarbothioic acid (23) on ecdysis of Oncopeltus fasciatus were examined in 50 related compounds. Marked ecdysis-inhibiting effects were elicited by substituted thiosemicarbazones of 2-acetyl-, 2-propionyl-, and 2-butyrylpyridine but 2-formyl, 2-phenylacetyl, and 2-benzoyl derivatives were inactive. Essential for activity was the thiocarbonyl moiety: analogues containing C = O or C = NH groups were inactive. Substitutents on the thiosemicarbazone portion of the molecule had variable effects: the 1-piperidinecarbothioic acid analogue of 23 exceeded the activity of 23, and five other analogues were as active as 23. Hydrogenation of the exocyclic C = N in 23 did not reduce its biological activity.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00118a009