• Fulltext

       

        Click here to view fulltext PDF


      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/127/04/0687-0699

    • Keywords

       

      Lactones; aromatic ring; feeding deterrents; storage pests; antifungal activity.

    • Abstract

       

      Eighteen racemic 𝛽-aryl-𝛾-lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (𝐸)-4-(benzo[𝑑][1′,3′]-dioxol-5′-yl)- but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a–c and 6a–c afforded 𝛾-ethyl-𝛾-lactones (7a–c, 8a–c) whereas the unsaturated lactones (9a–c, 10a–c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. 𝛾-Ethyl-𝛾-lactones 7a–c, 8a–c and unsaturated lactones 9a–c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a–c and 6a–c. trans-Iodolactones 6a–c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [𝑑][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

    • Author Affiliations

       

      Andrzej Skrobiszewski1 Witold Gładkowski1 Paulina Walczak1 Anna Gliszczyńska1 Gabriela Maciejewska2 Tomasz Klejdysz3 Jan Nawrot3 Czesław Wawrzeńczyk1

      1. Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
      2. Central Laboratory of the Instrumental Analysis, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
      3. Institute of Plant Protection – National Research Institute, Węgorka 20, 60-318 Poznań, Poland
    • Dates

       
    • Supplementary Material

       
  • Journal of Chemical Sciences | News

© 2021-2022 Indian Academy of Sciences, Bengaluru.