Design, Synthesis and Bioactivity of Novel Pyrimidine Sulfonate Esters Containing Thioether Moiety

Pesticides play an important role in crop disease and pest control. However, their irrational use leads to the emergence of drug resistance. Therefore, it is necessary to search for new pesticide-lead compounds with new structures. We designed and synthesized 33 novel pyrimidine derivatives containing sulfonate groups and evaluated their antibacterial and insecticidal activities. Results: Most of the synthesized compounds showed good antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Pseudomonas syringae pv. actinidiae (Psa) and Ralstonia solanacearum (Rs), and certain insecticidal activity. A(5), A(31) and A(33) showed strong antibacterial activity against Xoo, with EC50 values of 4.24, 6.77 and 9.35 mu g/mL, respectively. Compounds A(1), A(3), A(5) and A(33) showed remarkable activity against Xac (EC50 was 79.02, 82.28, 70.80 and 44.11 mu g/mL, respectively). In addition, A(5) could significantly improve the defense enzyme (superoxide dismutase, peroxidase, phenylalanine ammonia-lyase and catalase) activity of plants against pathogens and thus improve the disease resistance of plants. Moreover, a few compounds also showed good insecticidal activity against Plutella xylostella and Myzus persicae. The results of this study provide insight into the development of new broad-spectrum pesticides.

Automated summary

This study designed and synthesized 33 novel pyrimidine derivatives containing sulfonate groups and evaluated their antibacterial and insecticidal activities. Results showed that most of the synthesized compounds exhibited good antibacterial activity against various plant pathogens and certain insecticidal activity against Plutella xylostella and Myzus persicae.