Synthesis And Evaluation Of Novel Saccharin Derivatives Containing 1,2,3-Trizole Moiety

Saccharin, 1,2-benzisothiazole-3-one-1,1-dioxide, has gained considerable attention since the discovery of it. Its derivatives which are important classes of pharmaceuticals have been reported to possess a broad spectrum of biological activities such as inhibitors of histone deacetylase, tumor-associated carbonic anhydrase XII, kinase, human mast cell tryptase and tyrosinase, and anti-anxiety and antibacterial.1,2,3-Triazole is a versatile moiety that displays diverse biological activities, especially antifungal and antiviral in agriculture,which has been reviewed in introduction parts of some most recently published literatures. Several drug molecules containing 1,2,3-triazole group such as tazobactam and the cephalosporin cefatrizine are examples of antibiotic drugs that are clinically used for the treatment of bacterial infection. By introducing 1,2,3-triazole into organic molecules, we can get compounds with special properties like moderate dipole character, hydrogen bonding capability, rigidity and stability. Previous studies about the biological activities of saccharin containing 1,2,3-triazole moiety are not very much. To the best of our knowledge, litter data have been reported on the biological activities of saccharin derivatives containing 1,2,3-triazole moiety in the field of pesticide chemistry. In this study, both saccharin derivatives without 1,2,3-triazole moiety and a series of saccharin derivatives containing 1,2,3-triazole moiety were synthesized and evaluated their agricultural chemical activities.We designed and synthesized 23 saccharin derivative, there are 15 compounds containing 1,2,3-triazole which have not been reported in published literatures. The structures of all the newly synthesized compounds were elucidated and confirmed by FTIR, 1HNMR, 13CNMR, and high resolution mass spectrometer(HRMS). Compounds 5c, 10e, 10h and 10o with representative structure were preliminarily screened for their antifungal activities, plant growth regulatory activities, herbicidal activities, and antiviral activities against TMV. Excitingly, most selected compounds showed some extent herbicidal activities to two weeds, Rape and Barnyard grass. Therefore, the herbicidal activities of the other compounds had been done. All of compounds were tested in both 100 μg/mL and 10 μg/mL. The bioassays indicated that most of the title compounds displayed some extent herbicidal activities at 100 μg/mL. However, their activities decreased remarkably when then dose was reduced to 10 μg/mL. Most of compounds containing 1,2,3-triazole moiety 9 exhibited better herbicidal activities against rape than those compounds 4a-f, even though they were unfavorable to the enhancement of herbicidal activities for barnyard grass. For example, compound 9f (56.2%) show higher herbicidal activities against rape than its analogue 4c (15.9%) at 100 μg/mL, while the decreasing activity for barnyard grass was observed.