Quantitative structure-activity relationships of larvicidal N-[5-(substituted phenyl)-1, 3, 4-thiadiazol-2-yl]-benzamides in the inhibition of N-acetylglucosamine incorporation into a cultured integument system

Twenty-nine N-[5-(substituted phenyl)-1, 3, 4-thiadiazol-2-yl] benzamides with various substituents on both benzene rings were synthesized. Most of them inhibited the incorporation of N-acetyl-[1-14C]-glucosamine into cultured rice stem borer (Chilo suppresssalis WALKER) integument in the presence a...

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Bibliographic Details
Published in:Journal of Pesticide Science 1996-01, Vol.21 (2), p.195-201
Main Authors: Nakagawa, Y. (Kyoto Univ. (Japan). Coll. of Agriculture), Nishimura, K, Izumi, K, Kinoshita, K, Kimura, T, Kurihara, N, Fujita, T
Format: Article
Language:English
Subjects:
ACCION DE LOS PLAGUICIDAS
ACTION DES PESTICIDES
Biological and medical sciences
Chemical control
CHEMICAL STRUCTURE
Chilo suppressalis
Control
ESTRUCTURA QUIMICA
Fundamental and applied biological sciences. Psychology
INSECTICIDAS
INSECTICIDE
INSECTICIDES
PESTICIDE ACTIONS
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrates
Pyralidae
STRUCTURE CHIMIQUE
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Summary:Twenty-nine N-[5-(substituted phenyl)-1, 3, 4-thiadiazol-2-yl] benzamides with various substituents on both benzene rings were synthesized. Most of them inhibited the incorporation of N-acetyl-[1-14C]-glucosamine into cultured rice stem borer (Chilo suppresssalis WALKER) integument in the presence and absence of a metabolic inhibitor for oxidative degradation, piperonyl butoxide. Variations in the activity under each experimental condition were quantitatively analyzed with physicochemical substituent parameters and regression analyses. After the separation of the hydrophobic effect, para substituents on the benzene ring at the 5-position of the thiadiazole ring showed peculiar electronic and steric effects on the inhibitory activity. The greater the inductive component of the electron-withdrawing property and the molecular hydrophobicity, the higher the activity. Introduction of electron-donating groups such as OMe and Me at the ortho position of the benzoyl moiety seemed to be favorable to the activity. A limited number of compounds showed larvicidal activity against the insects via topical application.
ISSN:0385-1559
1348-589X
1349-0923
DOI:10.1584/jpestics.21.195