Synthesis and Insecticidal Activities of Tetrahydroimidazo[1,2-a]pyridinones: Further Exploration on <i>cis</i>-Neonicotinoids

<div><p></p><p> <i>cis</i>-Neonicotinoid, in which the nitro and cyano pharmacophore point to the same position relative to the heteroaromatic moiety, is a further extension of the neonicotinoid library. While seeking new <i>cis</i>-neonicotinoid candidates, a series of tetrahydroimidazo[1,2-a]pyridinone derivatives were synthesized by reactions of nitromethylene analogs with itaconic anhydride. All the compounds were confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and high-resolution mass spectroscopy. The target compounds had excellent insecticidal activities against cowpea aphids (<i>Aphis craccivora</i>) and brown planthopper (<i>Nilaparvata lugens</i>). Against armyworm, most of the compounds showed moderate activities. Interestingly, compound <b>12p</b> was active against <i>Tetranychus cinnabarinus.</i> The synthesized compounds displayed good insecticidal activities against different insect species, which might provide useful guidance for further design of <i>cis</i>-neonicotinoid candidates.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications</i>® for the following free supplemental resource(s): Full experimental and spectral details.]</p> </div>