Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests.
Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests.
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DOI：
10.1021/acs.jafc.1c05853
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发表时间：
2021-12
影响因子：
6.1
通讯作者：
Ruige Yang;Meiyue Han;J. Fan;Wanqing Cheng;Nannan Ma;Xiaoting Yan;Yong Guo
中科院分区：
文献类型：
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作者：
Ruige Yang;Meiyue Han;J. Fan;Wanqing Cheng;Nannan Ma;Xiaoting Yan;Yong Guo
为了提高（+）-诺卡酮的杀虫活性，合成了一系列含1，3，4-恶二唑/噻二唑结构的42（+）-诺卡酮硫醚，并对其对粘虫（Mythimna separata步行者）、桃蚜（Myzus persicae Sulzer）和小菜蛾（Plutella xylostella Linnaeus）的杀虫活性进行了评价。首次生物活性评价表明，在（+）-诺卡酮上引入1，3，4-恶二唑/噻二唑后，大部分目标化合物的杀虫活性均高于前体（+）-诺卡酮。在所有的（+）-诺卡酮衍生物中，化合物8 c（1 mg/mL）对M. 8 c的最终校正死亡率（CMR）为71.4%，分别是（+）-诺卡酮和川楝素的1.54倍和1.43倍; 8 s对小菜蛾的LC 50为0.27 mg/mL，是川楝素的3.37倍，略高于乙螨唑（0.28 mg/mL）。此外，在温室盆栽试验中，8 s对小菜蛾的防治效果优于乙螨唑。构效关系（SAR）表明，在（+）-诺卡酮的C-13位引入含卤代苯基的1，3，4-恶二唑/噻二唑，在大多数情况下可以得到对M. separata，M. persicae和P. xylostella的含量高于其它类群。此外，毒性试验表明，这些（+）-诺卡酮衍生物对昆虫的选择性优于非靶标生物（正常哺乳动物NRK-52 E细胞和C. idella和N. denticulata薯条），毒性相对较低。因此，上述结果表明，这些（+）-诺卡酮衍生物可以进一步探索作为新的先导化合物，开发潜在的生态友好型农药。
To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.