| 细交链孢菌酮酸及其衍生物的合成与杀虫活性 |
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| 引用本文： | 尤伟晨,刘小雨,刘现坤,柴源卿,王晓菲,吕培,花日茂.细交链孢菌酮酸及其衍生物的合成与杀虫活性[J].农药学学报,2022,24(2):260-271. |
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| 作者姓名： | 尤伟晨 刘小雨 刘现坤 柴源卿 王晓菲 吕培 花日茂 |
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| 作者单位： | 1.安徽农业大学 资源与环境学院，合肥 230036 |
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| 基金项目： | 国家自然科学基金青年基金项目(31901906)；安徽省省级大学生创新创业训练计划项目(S202010364275). |
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| 摘 要： | 为了寻找具有较高杀虫活性的特胺酸化合物，以天然活性产物细交链孢菌酮酸(TeA)作为先导化合物，利用酰基化米氏酸作为酰基化试剂，设计、合成了26个3-位不同酰基取代和5-位不同取代的含特胺酸骨架衍生物 4a~4s、5a~5g、7a 和 8a ，其中14个化合物未见文献报道，所有目标化合物的结构均经核磁共振氢谱、碳谱和高分辨质谱确证。初步杀虫活性测定结果表明，在100 μg/mL下处理72 h内，所有目标化合物对麦长管蚜Macrosiphum avenae (Fabricius)均表现出良好的杀虫活性，并具有内吸性，其中化合物 5d 和 7a 48 h致死率为100%，高于对照药剂螺虫乙酯，具有作为先导化合物进一步研究的价值。对处理后的小麦植株进行残留量测定，结果表明目标化合物 4e、5c、7a 和 8a 能被植株较好的吸收 。 该研究结果可为进一步研究具有特胺酸骨架化合物的构效关系提供参考。
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| 关 键 词： | 特胺酸 细交链孢菌酮酸 衍生物 杀虫活性 构效关系 |
| 收稿时间： | 2021-07-16 |
Synthesis and insecticidal activity of tenuazonic acid and derivatives |
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| Affiliation: | 1.College of Resources and Environment, Anhui Agricultural University, Hefei 230036, China |
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| Abstract: | In order to find tetramic acids with high insecticidal activity, the natural product tenuazonic acid (TeA) was used as lead compound, 26 tetramic acid derivatives 4a-4s , 5a-5g , 7a and 8a were designed and synthesized using acyl Meldrum's acid as acylation reagent with different substituted groups of tetramic acids at 3-position and 5-position, in which fourteen target compounds were not reported in the literature. The target compounds were confirmed by 1H NMR, 13C NMR and HRMS. The preliminary insecticidal activity eveluation showed that the target compounds had good insecticidal activity against wheat aphids (Macrosiphum avenae (Fabricius)) with systemic action at 100 μg/mL concentration for 72 h. Compounds 5d and 7a showed excellent insecticidal activities with the lethal rate of 100% in 48 h at the concentration of 100 μg/mL, which was higher than that of spirotetramat. 5d and 7a could be used as lead compounds for further research. The residues of 4e , 5c , 7a and 8a in wheat plants showed that the target compounds could be well absorbed. The study may provide a guideline of further studies on for structure-insecticidal activity relationships of tetramic acid derivatives. |
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