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One-pot synthesis, spectroscopic characterization and DFT study of novel 8-azacoumarin derivatives as eco-friendly insecticidal agents

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Abstract

A series of sixteen 8-azacoumarin derivatives bearing aryl moieties at C-5 and C-7 was designed and synthesized by a concise and facile procedure utilizing grinding and ultrasound approaches. The efficient multi-component protocols proceeded smoothly and in the absence of solvent to furnish the target products in moderate to good yields. All the synthesized molecules were characterized via 1HNMR, 13CNMR, IR, mass spectra, and elemental analyses. The density functional theory (DFT) was then used to discover the structural and electronic characteristics of such compounds. Finally, an insecticidal study against Plutella xylostella and Helicoverpa armigera on the synthesized compounds is reported. The bioassay results indicated that some of the tested compounds showed potency ranging from good to moderate. In particular, analogs 6i and 6l, among the tested compounds, showed even more potency than commercial chlorpyrifos. On the other hand, the rest of the tested compounds showed moderate to weak activities.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt

    Sameh A. Rizk, Galal A. Elsayed & Maher A. El-Hashash

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  1. Sameh A. Rizk
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  2. Galal A. Elsayed
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  3. Maher A. El-Hashash
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Correspondence to Sameh A. Rizk.

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Rizk, S.A., Elsayed, G.A. & El-Hashash, M.A. One-pot synthesis, spectroscopic characterization and DFT study of novel 8-azacoumarin derivatives as eco-friendly insecticidal agents. J IRAN CHEM SOC 15, 2093–2105 (2018). https://doi.org/10.1007/s13738-018-1402-3

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