Design, Synthesis And Biological Evaluation Of Amides Compounds Containing Azobenzene Moiety

Photoswithchable azobenzene derivatives between cis and trans isomer have broad application in many areas, such as optical memory material, light induced motor, drug delivery and other aspects. Photoactivated pesticide was a new type of pollution-free pesticide with great potential. Compared with tranditional chemical pesticides, it has the advantages of high efficiency, low toxicity, low residue and high selectivity.Based on the diamide insecticides, novel amides analogues containing azobenzene were designed through rational design. Two series of total29compounds were synthesized; all the compounds were characterized by nuclear magnetic resonance spectroscopy (1H NMR and13C NMR) and high resolution mass spectrometry (HR-MS).The photoswitchable behaviors of all the compounds were evaluated by UV visible spectra, NMR and ultra performance liquid chromatography. In addition to3compounds with strong electron withdrawing groups, all the other compounds could undergo reversible trans-to-cis isomerization upon light irradiation.All the compounds were assayed for insecticidal activity, but most of them had no activity or low activity due to poor solubility, which was unable to accurately evaluate the difference between cis and trans isomers.Some of the compounds were test for their ability to detect ion as probes, the trans isomer has good selective to fluoride ion anong other tested ions, while the cis-one had no ability for recognizing any ion.