State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, China.
J Agric Food Chem. 2012 Feb 1;60(4):1036-41. doi: 10.1021/jf203772d. Epub 2012 Jan 19.
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.
一系列含有 1,3,4-噁二唑部分的新型砜类化合物被设计和合成。它们的结构通过 (1)H 和 (13)C 核磁共振和元素分析得到确认。抗菌生物测定表明，大多数化合物在 200 μg/mL 时对烟草细菌性萎蔫具有有前途的体外抗菌生物活性。还讨论了结构与抗菌活性之间的关系。在标题化合物中，5'c、5'h、5'i 和 5'j 在 39.8、60.3、47.9 和 32.1 μg/mL 时分别可以抑制丁香假单胞菌的菌丝生长约 50%（EC(50)）。其中，化合物 5'j 是最有前途的候选物，因为它在相同浓度范围内的效果比 Kocide 3000 [Cu(OH)(2)]更强。田间试验表明，化合物 5'j 对烟草细菌性萎蔫的防治效果优于商业杀菌剂噻菌铜。这是首次证明含有 1,3,4-噁二唑的砜衍生物可用于开发潜在的植物杀菌剂。
