Projuvenoids: synthesis and biological evaluation of sulfenylated, sulfinylated, and sulfonylated carbamates.
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 biscarbamates 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 biscarbamates 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.
Ujváry
I
I
Plant Protection Institute, Hungarian Academy of Sciences, Budapest, Hungary.
Matolcsy
G
G
Bélai
I
I
Szurdoki
F
F
Bauer
K
K
Varjas
L
L
Kramer
K J
KJ
D000818:Animals; D001681:Biological Assay; D002080:Butterflies; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001517:Coleoptera; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007605:Juvenile Hormones / Q000494:pharmacology; D018716:Molecular Mimicry; D015394:Molecular Structure; D048448:Phenylcarbamates; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013455:Sulfur / Q000737:chemistry
D002219:Carbamates; D007306:Insecticides; D007605:Juvenile Hormones; D048448:Phenylcarbamates; D011355:Prodrugs; D013455:Sulfur; C052034:fenoxycarb