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Projuvenoids: Synthesis and biological evaluation of sulfenylated, sulfinylated, and sulfonylated carbamates
Author(s) -
Ujváry István,
Matolcsy György,
Bélai Iván,
Szurdoki Ferenc,
Bauer Krisztina,
Varjas László,
Kramer Karl J.
Publication year - 1996
Publication title -
archives of insect biochemistry and physiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.576
H-Index - 66
eISSN - 1520-6327
pISSN - 0739-4462
DOI - 10.1002/(sici)1520-6327(1996)32:3/4<659::aid-arch37>3.0.co;2-9
Subject(s) - carbamate , lipophilicity , carbaryl , biology , biological activity , sitophilus , disulfide bond , biochemistry , chromatography , chemistry , pesticide , botany , in vitro , agronomy
Abstract Applying the proinsecticide principle developed earlier for neurotoxic carbamate insecticides, a series of new N ‐sulfenylated, N ‐sulfinylated, and N ‐sulfonylated derivatives of fenoxycarb were synthesized and evaluated for juvenile hormone mimicking activity. Laboratory evaluations of the compounds using Pieris brassicae and Sitophilus oryzae, as well as field experiments using Bemisia tabaci, showed that several symmetrical bis carbamates with either a sulfenyl or sulfinyl bridge possessed higher activity than the parent carbamate. From the unsymmetrical compounds containing biologically inert derivatizing moieties, one of the sulfenylated bis carbamates also showed improved activity against P. brassicae. The changes in the biological activity of the sulfur‐containing derivatives compared to that of the parent compound are attributed to the modified physicochemical characteristics, i.e., increased lipophilicity facilitating penetration, transport, as well as protection of the compound from metabolism. © 1996 Wiley‐Liss, Inc.