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Effect of substituent and ring changes in naturally occurring naphthoquinones on the feeding response of larvae of the Mexican bean beetle, Epilachna varivestis

Effect of substituent and ring changes in naturally occurring naphthoquinones on the feeding response of larvae of the Mexican bean beetle, Epilachna varivestis. Weissenberg, M.; Meisner, J.; Klein, M.; Schaeffler, I.; Eliyahu, M.; Schmutterer, H.; Ascher, K. R. S. (Lab. Nat. Prod. Chem., Volcani Cent.Several reagents such as 117-80-6 is used here., Bet Dagan 50250, Israel). Journal of Chemical Ecology, 23(1), 3-18 (English) 1997 Plenum. CODEN: JCECD8. ISSN: 0098-0331. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) Behavioral evaluation of the antifeedant effect of 10 naturally occurring 1,4-naphthoquinones on larvae of the Mexican bean beetle, Epilachna varivestis was undertaken concurrently with that of a series of synthetic analogs and model compds. in order to assess structure-activity relationships. Plumbagin, 1,4-naphthoquinone, juglone, menadione, and naphthazarin, which were active at 0.3%, were also bioassayed at 0.1, 0.05, and 0.01%, at which concn. 1,4-naphthoquinone still retained some activity. The model studies suggest that two structural features might be operative independently against E. varivestis: one consisting of a properly substituted naphthoquinone moiety and the other requiring a benzo- or naphthohydroquinone. Within the naphthoquinone group, the relative activity is detd. by a substituent effect which is the outcome of a complex interplay of electronic, steric,electrochem., and positional requirements. Among the model compds., 2-chloro-3-amino-1,4-naphthoquinone and a-naphthylamine displayed activity, even at 0.01%. The results should enable selection of plant sources for naphthoquiones possessing larval inhibition properties. .