Abstract
Amide alkaloids and amine alkaloids play an important role in insecticidal and antibacterial activity, respectively. What activity is produced when they fuse with phenylpyrazole parent structure to form a two-site alkaloid? A series of sulfonyl phenylpyrazole alkaloids (PAs) incorporating amides and amine two-site moiety were diversified designed and one-pot sonic solvothermal synthesized for the first time, which were fully characterized and crystal analysis. Preliminary bioassays indicated that PA5b had excellent insecticidal bioactivity against 3rd instar larvae of P. xylostella and M. separata and 4.1 times more bacteriostatic activity against A. tumefaciens than parent compound. The results of molecular docking revealed that amides and amine units in PAs had strong synergistic interactions with GABA receptors, such as hydrogen, halogen and hydrophobic bonds, resulting in high insecticidal activity and strong bacteriostatic effects through two-site combination. Furthermore, PA5b formed π-cation interactions with the GABA receptor, verified by crystal structure and Hirshfeld surface analysis. Photophysical tests exhibited that amide and amine moiety of PAs expanded the conjugation system to improve their light absorption and fluorescence, and PAs possessed photo-self-degradability under simulated natural light irradiation, which could be reconverted to phenylpyrazole parental fragments, thus improving their bioactivity and reducing residues. The structure-properties relationship of sulfonyl phenylpyrazole two-site alkaloids was analyzed by CoMFA modeling and Hirshfeld surface for the presence of bioactive sites at the sulfone and amine sites. These findings lay the foundation for the development of two-site alkaloid insecticides and provide new ideas for their natural degradation and fluorescent detection.
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