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

Abstract

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. A5, A31 and A33 showed strong antibacterial activity against Xoo, with EC50 values of 4.24, 6.77 and 9.35 μg/mL, respectively. Compounds A1, A3, A5 and A33 showed remarkable activity against Xac (EC50 was 79.02, 82.28, 70.80 and 44.11 μg/mL, respectively). In addition, A5 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.

Design and Synthesis of Novel Antimicrobial Agents

“…Irrational use of pesticides leads to the emergence of drug resistance. The need for the development of a new broad-spectrum pesticide to control plant pests and disease infestations led Li et al [ 215 ] to combine pyrimidine with sulfonate ester for the development of interesting bioactive compounds. A novel series of pyrimidine derivatives containing sulfonate esters were designed.…”

Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies

“…Aryl sulfonate esters have been widely used for agricultural and pharmaceutical research due to their antiviral [ 14 , 15 ], antibacterial [ 16 ], antifungal [ 17 ], insecticidal [ 18 ], and anticancer [ 19 ] properties. And more aryl sulfonate compounds with high efficacy in insecticidal, antibacterial, and antiviral activities can be obtained by structural modification [ 20 , 21 ], such as, genite, irosustat, chlorfenson and nimrod, etc. In recent years, 1,3,4-thiadiazole derivatives and amide derivatives have become a major focus for the development of novel bactericides, insecticides, and fungicides [ 22 – 26 ], and a number of commercial agents containing thiadiazole/amide structures have been discovered and commercialized, such as bismerthiazol, thiodiazole copper, boscalid, diflubenzuron, and chlorantraniliprole, etc.…”

“…In recent years, 1,3,4-thiadiazole derivatives and amide derivatives have become a major focus for the development of novel bactericides, insecticides, and fungicides [ 22 – 26 ], and a number of commercial agents containing thiadiazole/amide structures have been discovered and commercialized, such as bismerthiazol, thiodiazole copper, boscalid, diflubenzuron, and chlorantraniliprole, etc. [ 21 ]. In view of the above, a series of novel sulfonate derivatives containing 1,3,4-thiadiazole/amide backbone was designed and synthesized for further development of efficient and active lead compounds (Fig.…”

Discovery of 3-Formyl-N-(un)Substituted Benzylindole Pyrimidines as an Acaricidal Agent and Their Mechanism of Action

“…It also occurs in the oil of jasmine, cloves, and coal tar . Indole and its derivatives possess diverse biological properties including anticancer, antioxidant, , anti-inflammatory, and pesticidal activities. − On the other hand, it is worth noting that the pyrimidine heterocycle as the most common diazine showed some important agricultural biological activities, including antifungal (A, Figure ), insecticidal (B, Figure ), antiviral (C, Figure ), and antibacterial (D, Figure ) effects . To find the potent acaricide candidate, consequently, in this study, we wanted to prepare a series of 3-formyl- N -(un)­substituted benzylindole pyrimidines (Figure ) by introduction of the pyrimidine fragment into the indole skeleton through the successive Vilsmeier–Haack–Arnold (VHA), aldol condensation, and cyclization reactions.…”