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Juvenile hormonal activity of mono‐ and polyenehomobenzenes in Drosophila virilis, Spodoptera frugiperda and Araschnia levana
Author(s) -
Demuth Martin,
Zambrano Jorge L,
Rosales Viale,
Lorenz Matthias W
Publication year - 2007
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.1396
Subject(s) - juvenile hormone , lepidoptera genitalia , noctuidae , spodoptera , biology , regioselectivity , sex pheromone , stereochemistry , allylic rearrangement , methoprene , drosophila virilis , botany , chemistry , insect , drosophila (subgenus) , biochemistry , catalysis , gene , recombinant dna
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. Copyright © 2007 Society of Chemical Industry