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Design, synthesis, and insecticidal activity evaluation of novel 4-(N, N-diarylmethylamines) furan-2(5H)-one derivatives as potential acetylcholine receptor insecticides.
Pest Management Science 2018 June 29
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, the 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 LC50 value of 1.72 μg mL-1 , which was superior to that of pymetrozine (LC50 = 6.86 μg mL-1 ). The result of molecular docking indicated that 4cc will 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 nicotinic acetylcholine receptor. Compound 4cc also decreased the ability for oxidative metabolism, which further supported the result of molecular docking.
CONCLUSION: This work can be used to further investigate the mechanism underlying the insecticidal activity of butenolide derivatives and develop potential novel butenolide insecticides. This article is protected by copyright. All rights reserved.
RESULTS: Some target molecules exhibited good insecticidal activities against Aphis craccivora. Among the title compounds, 4cc showed the best insecticidal activities with an LC50 value of 1.72 μg mL-1 , which was superior to that of pymetrozine (LC50 = 6.86 μg mL-1 ). The result of molecular docking indicated that 4cc will 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 nicotinic acetylcholine receptor. Compound 4cc also decreased the ability for oxidative metabolism, which further supported the result of molecular docking.
CONCLUSION: This work can be used to further investigate the mechanism underlying the insecticidal activity of butenolide derivatives and develop potential novel butenolide insecticides. This article is protected by copyright. All rights reserved.
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