Juvenile hormonal activity of mono- and polyenehomobenzenes in Drosophila virilis, Spodoptera frugiperda and Araschnia levana.
A series of mono- and polyenehomobenzenes was synthesised by a highly regioselective palladium-catalysed allylic alkylation of substituted and unsubstituted benzylic Grignard reagents employing catalytic amounts of catalyst and tested for juvenile hormone activity on the fruit fly Drosophila virilis Sturtevant (Diptera: Drosophilidae), on an important agricultural pest species, the fall armyworm Spodoptera frugiperda JE Smith (Lepidoptera: Noctuidae), and on the map butterfly Araschnia levana L. (Lepidoptera: Nymphalidae). In D. virilis only polyenehomobenzenes with a geranyl chain and a methyl, methoxy or isopropyl group at the para position of the aromatic ring displayed significant juvenile hormonal activity at low doses. A monoenehomobenzene and polyenehomobenzenes with longer allylic chains or without a substituted aromatic ring were not active. In S. frugiperda and in A. levana, a mono-, a di- and a tetraene displayed juvenile hormonal activity. In the lepidopteran species, a trend for the necessity of a substitution at position 4 of the phenyl group for high juvenile hormonal activity was also found.
Demuth
Martin
M
Max-Planck Institute for Bioinorganic Chemistry, D-45413 Mülheim an der Ruhr, Germany.
Zambrano
Jorge L
JL
Rosales
Viale
V
Lorenz
Matthias W
MW
D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000494:pharmacology*; D004330:Drosophila / Q000187:drug effects*; D007605:Juvenile Hormones / Q000032:analysis*; D008018:Life Cycle Stages / Q000187:drug effects*; D009036:Moths / Q000187:drug effects; D018411:Spodoptera / Q000187:drug effects*
D004224:Diterpenes; D007605:Juvenile Hormones