Discovery of 3-Formyl-N-(un)Substituted Benzylindole Pyrimidines as an Acaricidal Agent and Their Mechanism of Action

Le résumé fourni par la source

To discover the pronounced acaricide candidate, herein, a series of 3-formyl- N -(un)substituted benzylindole pyrimidines were prepared by structural modification of indoles at the N-1 and C-3 positions via the successive Vilsmeier–Haack–Arnold (VHA), aldol condensation, and cyclization reactions. The steric structures of nine compounds were undoubtedly confirmed by X-ray single-crystallography. Against Tetranychus cinnabarinus Boisduval, compounds V-15, V-31, V-34, V-42, V-44, and V-60 exhibited promising acaricidal activity with LC 50 values of 0.299 – 0.481 mg/mL. In particular, compound V-34 displayed 4.2 times the acaricidal activity of its precursor 6-methylindole. Scanning electron microscopy (SEM) imaging revealed that the construction of the cuticle layer of V-34 -treated T. cinnabarinus was seriously destroyed. Furthermore, RNA-Seq analysis indicated that compound V-34 could regulate the homeostasis metabolism of T. cinnabarinus through arachidonic acid and linoleic acid metabolism and lysosome pathways. These results suggested that compound V-34 can be further studied as a lead acaricidal agent.

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