Design and One-Pot Ultrasound Synthesis of Inorganic Base-Promoted Fluorescent Ligand-Gated Ion Channel Fused Arylpyrazole Sulfonamide Skeletons to Enhance Phloem Mobility and Insecticidal Activity as GABA and nACh Receptors Inhibitors

Abstract

Ligand-gated ion channels are essential in living organisms, and sulfonamides have antibacterial effects and can be readily coordinated with metal ions with good biological activity. A series of fluorescent ligand-gated ion channel fused arylpyrazole sulfonamide skeletons (APSn M ) were synthesized based on a one-pot ultrasound strategy promoted by an inorganic base. APSn M had a high fluorescence quantum yield and a large Stokes shift in ethanol solvent. The ligand bonded ions took on a different color from the ligand and can be used as a probe to detect their own residue on plant surfaces. Their hydrophobic parameters and the fluorescence distribution in Chinese cabbage leaves indicated that APSn M significantly increased the phloem mobility of the plant. The insecticidal activity of APS3 Na was higher (LC 50 = 7.2423 μg/mL) than that of fipronil (15.2312 μg/mL) against Plutella xylostella, and the mechanism of high insecticidal activity of APS3 Na was simulated by molecular docking, which confirmed its strong interactions with the GABA and nACh receptors of Plutella xylostella. Analysis of the crystal structure of these ligand-gated ion channels further confirmed the consistency of their structure and biological activity.