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Antifeedant and Phytotoxic Activity of the Sesquiterpene p -Benzoquinone Perezone and Some of its Derivatives



The sesquiterpene p -benzoquinone perezone ( 1 ), isolated from Perezia adnata var . alamani (Asteraceae), and its non-natural derivatives isoperezone ( 2 ), dihydroperezone ( 3 ), dihydroisoperezone ( 4 ), and anilidoperezone ( 5 ) were tested as antifeedants against the herbivorous insects Spodoptera littoralis , Leptinotarsa decemlineata , and Myzus persicae . Compounds 1 – 5 exhibited strong antifeedant activity against L. decemlineata and M. persicae , and elicited a low response by S. littoralis . Antifeedant activity on L. decemlineata and M. persicae increased when the hydroxyl group at C-3 in perezone ( 1 ) was changed to C-6 to give isoperezone ( 2 ). The same effect was found with hydrogenation of the double bond of the alkyl chain of (1) to yield dihydroperezone ( 3 ). In contrast, hydrogenation of this double bond in isoperezone ( 2 ) to give dihydroisoperezone ( 4 ) led to a reduction in antifeedant activity. Determination of the phytotoxic activity of 1 – 5 revealed that 3 had a significant inhibition effect on Lactuca sativa radicle length growth.



Journal of Chemical EcologySpringer Journals

Published: Jun 1, 2008

DOI: 10.1007/s10886-008-9495-2

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