Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety

Abstract

A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by (1)H and (13)C nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 μg/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c, 5'h, 5'i, and 5'j could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC(50)) at 39.8, 60.3, 47.9, and 32.1 μg/mL, respectively. Among them, compound 5'j was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 5'j against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities

“…Substituted 1,3,4-oxadiazoles are one of the most important heterocyclic compounds, which have gained attention because of their remarkable biological and pharmacological properties [6][7][8][9][10][11][12][13][14][15] . Substituted 1,3,4-oxadiazoles are one of the most important heterocyclic compounds, which have gained attention because of their remarkable biological and pharmacological properties [6][7][8][9][10][11][12][13][14][15] .…”

Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III

“…Antimycin A, [21] a nature product isolated from streptomyces sp. [27][28] Initially, we envisioned that the integration of the biphenyl ether, which has been demonstrated their inherent importance in agrochemistry, with the sulfonamide azolyl pharmacophore may result in a novel class of structure as depicted in Figure 1 with efficient Q i site inhibition. [23][24][25] Bolgunas and Tokutake have successfully simplified antimycin scaffold by replacing the dilactone portion of the molecule with biphenyl and biphenyl ether group ( Figure 1).…”

Synthesis and Biological Activities of 1, 3, 4-Oxadiazole Derivatives: A Review of Literature.

“…, [22] (2012) were designed and synthesised 1,3,4-oxadiazole moiety containing sulfone groups (scheme: 5) and were reported to have ability to mycelia growth of Ralstonia solanacearum in vitro also having better control effect against tobacco bacterial wilt so sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants. Scheme 5:-Puthiyapurayil P, et al, [12] (2012), were synthesised S-substituted-1, 3, 4-oxadiazole bearing N-methyl4 (trifluoromethyl)phenyl pyrazole moiety (scheme: 6) and reported to have anticancer activity.…”