Design, synthesis, and insecticidal activity evaluation of novel 4-(N, N-diarylmethylamines)furan-2(5H)-one derivatives as potential acetylcholine receptor insecticides.

BACKGROUND: Flupyradifurone is a member of a novel class of insecticides that possess excellent insecticidal activities. Halogen-containing phenyl groups are important and indispensable structural components of many pesticides. However, replacement of the difluoromethyl group of flupyradifurone with halogen-containing phenyl groups has not been reported. Hence, a series of novel butenolide derivatives containing phenyl groups were synthesized and bioassayed to discover novel compounds with excellent insecticidal activities. RESULTS: Some target molecules exhibited good insecticidal activities against Aphis craccivora. Among the title compounds, 4cc showed the best insecticidal activities with an 50% lethal concentration (LC50 ) value of 1.72 µg mL-1 , which is superior to that of pymetrozine (LC50  = 6.86 µg mL-1 ). Molecular docking indicated that 4cc lacks oxidative metabolism by CYP6CM1 and metabolic resistance with imidacloprid. Furthermore, label-free quantitative proteomic analysis indicated that 4cc may be a potential acetylcholine receptor insecticide that acts on the nicotinic acetylcholine receptor. Compound 4cc also decreased the capability for oxidative metabolism, which further supported the molecular docking results. CONCLUSION: This work can be used to further investigate the mechanism underlying the insecticidal activity of butenolide derivatives and develop potential novel butenolide insecticides. © 2018 Society of Chemical Industry.

Novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities.

BACKGROUND: The literature shows that bisthioether and 1,3,4-oxadiazole derivatives exhibit a wide variety of biological activities. In this study, a series of novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety were synthesized and their antibacterial and nematocidal activities investigated. RESULTS: Among the title compounds evaluated, compound 4f demonstrated the best antibacterial activities against rice bacterial leaf blight, rice bacterial leaf streak and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas axonopodis pv. citri (Xac), with EC50 values of 4.82, 11.15 and 16.57 µg mL-1 , respectively, which were even better than those of thiodiazole copper and bismerthiazol. Meanwhile, compound 4f had better in vitro nematocidal activity against Caenorhabditis elegans at 48 h, with an LC50 value of 2.89 µg mL-1 , which was superior to those of ethoprophos and fosthiazate. In addition, greenhouse trials indicated that compound 4f was effective in reducing rice bacterial leaf blight relative to thiodiazole copper and bismerthiazol. CONCLUSION: A series of novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety were synthesized and bioassay results showed that compound 4f exhibited the best antibacterial and nematocidal activities. © 2017 Society of Chemical Industry.