Functionalized Thiacalix[4]arenes as Dual Metal-Ion Extractants and Insecticidal Agents: Synthesis, Characterization,...

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Agrochemical Research

Background:

• Thiacalixarenes are versatile macrocyclic hosts with potential applications in ion recognition and pest control.
• Modifying thiacalixarene structures can tune their binding affinities and biological activities.

Purpose of the Study:

• To synthesize novel carbonyl thiacalixarene derivatives.
• To evaluate their metal ion extraction capabilities.
• To assess their potential as synergists in insecticide formulations.

Main Methods:

• Synthesis of five thiacalixarene derivatives (5, 6, 7, 9, 10) using various reagents.
• Characterization of synthesized compounds via IR and NMR spectroscopy.
• Liquid-liquid extraction of metal picrates to determine ion-binding affinities.
• Insecticidal assays against Spodoptera littoralis larvae in combination with chlorfenapyr.

Main Results:

• Compounds 7, 9, and 10 exhibited moderate to high metal ion extraction efficiencies.
• Thiacalixarene 9 demonstrated superior Cs+ extraction (93.4%) and broad-spectrum metal ion binding.
• The synthesized derivatives enhanced the insecticidal activity of chlorfenapyr against Spodoptera littoralis larvae.

Conclusions:

• Carbonyl-to-thionyl conversion in thiacalixarenes significantly impacts metal-ligand interactions.
• These novel thiacalixarene derivatives show promise for selective metal ion separation.
• Thiacalixarene derivatives can act as effective synergists, improving pesticide performance and offering a strategy for next-generation agrochemicals.