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<p><i>Of</i>ChtI and <i>Of</i>Chi-h are ideal targets for developing agricultural inhibitors against <i>Ostrinia furnacalis</i>. In order to further confirm the importance of conjugated systems in rhodanine derivatives, sixteen novel 1,4-benzodioxane-tethered-rhodanine derivatives were designed and synthesized with or without C=C double bond of 5-alkenyl rhodanine skeleton. Among them, compounds <b>3a</b>–<b>3h</b>, with preserved 5-alkenyl rhodanine skeleton, all exhibited much better inhibitory activities against both <i>Of</i>ChtI and <i>Of</i>Chi-h, compared to that of the corresponding reduced compounds <b>4a</b>–<b>4h</b> without its C=C double bond. The inhibitory mechanism demonstrated that the 5-alkenyl rhodanine conjugated plane was conducive to improving the binding affinity with both two chitinases. Compound <b>3g</b> was identified as the most potential dual-chitinases inhibitor against <i>Of</i>ChtI (<i>K</i><sub>i</sub> = 2.57 μM) and <i>Of</i>Chi-h (<i>K</i><sub>i</sub> = 2.03 μM). The bioassay study also indicated that compound <b>3g</b> displayed the best insecticidal activity against <i>O. furnacalis</i> and distinctive sublethal effect in regulating its growth and development. These 1,4-benzodioxane-tethered-rhodanine derivatives deserved further investigation as novel dual-chitinases inhibitor candidates in the control of <i>O. furnacalis</i>.</p><p></p>

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Novel conjugated 5-alkenyl rhodanine tethered 1,4-benzodioxane derivatives as dual-chitinases inhibitors to hinder the growth of Asian corn borer

  • 期刊论文

  • 发表日期：

    2025年2月12日

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  • Jinxiu Chen,
  • Dongmei Shi,
  • Zhiyang Jiang,
  • Renxuan Zou,
  • Jingyu Zhang,
  • Qing Han,
  • Na Wang,
  • Zhijian Xu,
  • Qing Yang,
  • Hongxia Duan

摘要

OfChtI and OfChi-h are ideal targets for developing agricultural inhibitors against Ostrinia furnacalis. In order to further confirm the importance of conjugated systems in rhodanine derivatives, sixteen novel 1,4-benzodioxane-tethered-rhodanine derivatives were designed and synthesized with or without C=C double bond of 5-alkenyl rhodanine skeleton. Among them, compounds 3a–3h, with preserved 5-alkenyl rhodanine skeleton, all exhibited much better inhibitory activities against both OfChtI and OfChi-h, compared to that of the corresponding reduced compounds 4a–4h without its C=C double bond. The inhibitory mechanism demonstrated that the 5-alkenyl rhodanine conjugated plane was conducive to improving the binding affinity with both two chitinases. Compound 3g was identified as the most potential dual-chitinases inhibitor against OfChtI (Ki = 2.57 μM) and OfChi-h (Ki = 2.03 μM). The bioassay study also indicated that compound 3g displayed the best insecticidal activity against O. furnacalis and distinctive sublethal effect in regulating its growth and development. These 1,4-benzodioxane-tethered-rhodanine derivatives deserved further investigation as novel dual-chitinases inhibitor candidates in the control of O. furnacalis.