Design, synthesis, and insecticidal activity of novel neonicotinoid derivatives containing N-oxalyl groups

Abstract

Two series of novel neonicotinoid derivatives containing N-oxalyl groups were designed and synthesized, and their structures were characterized by 1 H NMR spectroscopy, high-resolution mass spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 13c, 13d, 13g, 13h, and 13i against bean aphids at 12.5 mg kg -1 were 100%; the insecticidal activities against bean aphids of the derivative 13 c, 13d, 13g, 13h, and 14h were comparable to imidacloprid at 6.25 mg kg -1 . Surprisingly, the results indicated that the activity of ethyl 2-(3-((6-chloropyridin-3-yl)methyl)-2-(nitroimino)imidazolidin-1-yl)-2-oxoacetate (13b) against bean aphids at 6.25 mg kg -1 was 96%, which was higher than the commercialized imidacloprid.

Design, Synthesis, Crystal Structure, Insecticidal Activity, Molecular Docking, and QSAR Studies of Novel N3-Substituted Imidacloprid Derivatives

“…Meanwhile, it has been widely known that the physical properties of an insecticidal compound may be manipulated to obtain products with other selected types of activity by proper selection of the derivative moiety. Encouraged by these investigations, some N 3 -substituted imidacloprid derivatives, such as bis-imidacloprid, crown-capped imidacloprid, N 3 -oxalyl imidacloprid derivatives, have been prepared by different groups in recent years. It should be noted that these reported N 3 -substituted compounds may act as pro-drug by hydrolyzing to IMI.…”