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Evaluation of Dimboa Analogs as Antifeedants and Antibiotics Towards the Aphid Sitobion avenae in Artificial Diets

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Abstract

A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.

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Authors and Affiliations

  1. Departamento de Ciencias Ecológicas, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile

    Carlos A. Escobar

  2. Institut für Organische Chemie der Universität Leipzig, D-04103, Leipzig, Germany

    Dieter Sicker

  3. Departamento de Ciencias Ecológicas, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile

    Hermann M. Niemeyer

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  1. Carlos A. Escobar
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  2. Dieter Sicker
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  3. Hermann M. Niemeyer
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Escobar, C.A., Sicker, D. & Niemeyer, H.M. Evaluation of Dimboa Analogs as Antifeedants and Antibiotics Towards the Aphid Sitobion avenae in Artificial Diets. J Chem Ecol 25, 1543–1554 (1999). https://doi.org/10.1023/A:1020832731546

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