Insect pest management agents: hormonogen esters (juvenogens).
The chemical part of this investigation focused on designing structures and synthesizing a series of six new esters (juvenogens), derived from biologically active insect juvenile hormone bioanalogues (juvenoids, JHAs) and unsaturated short-chain linear and branched fatty acids for possible application as biochemically targeted insect hormonogen agents. The structures of the new compounds were assigned on the basis of a detailed NMR analysis of their (1)H and (13)C NMR spectra. The biological part of this investigation focused on introductory biological screening tests with these compounds against the red firebug (Pyrrhocoris apterus), termites (Reticulitermes santonensis and Prorhinotermes simplex), and the blowfly (Neobellieria bullata). The biological activity of the juvenogens was studied in relation to the fatty acid functionality in the structures. Notable biological activity in topical tests and medium activity in peroral tests was found for the juvenogens 3 and 7 with P. apterus. The compounds 6 and 8 showed the lowest activity in both topical and oral assays with P. apterus. Considerable effect of all tested juvenogens was observed in P. simplex; however, the juvenogens 5 and 6 (derivatives of the only branched short-chain fatty acid) showed no activity against R. santonensis. The effect of the compounds 3-8 on larval hatching of N. bullata was only moderate (larval hatching 80-90%); however, the proliferation effect caused by 5, 6, and 8 is more pronounced than the effect caused by 3, 4, and 7.
Wimmer
Zdenek
Z
Laboratory of Chemistry, Institute of Experimental Botany, Academy of Sciences of the Czech Republic, VídenskA 1083, CZ-14220 Prague 4, Czech Republic. wimmer@ueb.cas.cz
Jurcek
Ondrej
O
Jedlicka
Pavel
P
Hanus
Robert
R
Kuldová
Jelena
J
Hrdý
Ivan
I
Bennettová
Blanka
B
Saman
David
D
D000818:Animals; D004175:Diptera; D004952:Esters / Q000008:administration & dosage / Q000737:chemistry; D007306:Insecticides / Q000008:administration & dosage / Q000737:chemistry; D020049:Isoptera; D007605:Juvenile Hormones / Q000008:administration & dosage / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
D004952:Esters; D007306:Insecticides; D007605:Juvenile Hormones