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细交链孢菌酮酸及其衍生物的合成与杀虫活性

尤伟晨 刘小雨 刘现坤 柴源卿 王晓菲 吕培 花日茂

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. doi: 10.16801/j.issn.1008-7303.2022.0001
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. doi: 10.16801/j.issn.1008-7303.2022.0001
YOU Weichen, LIU Xiaoyu, LIU Xiankun, CHAI Yuanqing, WANG Xiaofei, LYU Pei, HUA Rimao. Synthesis and insecticidal activity of tenuazonic acid and derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 260-271. doi: 10.16801/j.issn.1008-7303.2022.0001
Citation: YOU Weichen, LIU Xiaoyu, LIU Xiankun, CHAI Yuanqing, WANG Xiaofei, LYU Pei, HUA Rimao. Synthesis and insecticidal activity of tenuazonic acid and derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 260-271. doi: 10.16801/j.issn.1008-7303.2022.0001

细交链孢菌酮酸及其衍生物的合成与杀虫活性

doi: 10.16801/j.issn.1008-7303.2022.0001
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).
详细信息
    作者简介:

    尤伟晨,you19950720@163.com

    通讯作者:

    吕培,lvpei@ahau.edu.cn.

  • 中图分类号: O626.1;TQ450.11

Synthesis and insecticidal activity of tenuazonic acid and derivatives

Funds: the National Natural Science Foundation of China (31901906) and College student innovation and entrepreneurship training program of Anhui Province (S202010364275).
  • 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、7a8a ,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 5d7a 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、7a8a 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。
  • 1  3-酰基特胺酸的生物合成[4]

    1.  Biosynthetic route of 3-acylated tetramic acid[4]

    2  TeA (1) 及其5R, 6S-异构体 (2) 的结构

    2.  Structures of tenuazonic acid and its 5R,6S-isomer

    3  目标化合物4a~4s和5a~5g的合成路线

    3.  The synthetic route of the target compounds 4a-4s and 5a-5g

    4  目标化合物7a和8a的合成路线

    4.  The synthetic route of the target compounds 7a and 8a

    5  3-酰基特胺酸互变异构[18]

    5.  Tautomerism of 3-acylated tetramic acid[18]

    表  1  目标化合物的质谱分析参数

    Table  1.   Mass spectrometry parameters of target compounds

    化合物
    Compd
    保留时间
    Retention time/min
    母离子
    Precursor ion, m/z
    子离子
    Product ion, m/z
    驻留时间
    Dwell time/s
    锥孔电压
    Declustering potential/V
    碰撞能量
    Collision energy/eV
    4e2.38198.0796.70.055018
    138.80.055016
    5c3.40252.12153.920.055020
    177.890.055022
    7a2.58311.95158.780.055034
    196.620.055026
    8a4.06410.0370.880.055016
    311.90.055016
    下载: 导出CSV

    表  2  目标化合物在100 μg/mL下对麦蚜的杀虫活性

    Table  2.   Insecticidal activity of target compounds against wheat aphid under the concentration of 100 μg/mL

    化合物
    Compd.
    校正死亡率
    Corrected mortality/%
    24 h48 h72 h
    4a0750
    4b01772
    4c06294
    4d04190
    4e04198
    4f06890
    4g04458
    4h05582
    4i23794
    4j33872
    4k22476
    4l307091
    4m36494
    4n072100
    4o34778
    4p46694
    4q3977100
    4r (TeA)488697
    4s4481100
    5a468896
    5b826894
    5c3594100
    5d77100
    5e4497100
    5f5473100
    5g6278100
    7a1100
    8a1793100
    螺虫乙酯 spirotetramat4190100
    下载: 导出CSV

    表  3  目标化合物在麦苗中的平均添加回收率和相对标准偏差 (RSD) (n = 5)

    Table  3.   The average recoveries and RSD of target compounds in wheat seedlings (n = 5)

    化合物
    Compd.
    添加水平
    Spiked level/(mg/kg)
    平均回收率
    Average recovery/%
    相对标准偏差
    RSD/%
    4e10950.4
    1001010.7
    5001002.4
    5c10990.4
    1001010.5
    5001010.9
    7a101100.06
    1001010.09
    500962.3
    8a10970.08
    1001010.2
    500990.4
    下载: 导出CSV

    表  4  目标化合物在麦苗中的残留量

    Table  4.   Residue of target compounds in wheat seedlings

    化合物
    Compd.
    线性回归方程
    Linear regression equation

    决定系数
    R2
    残留量
    Residue/(mg/kg)
    4ey=9538023.74x ‒ 5889.381.0013.58
    5cy=39382191.04x ‒ 131984.321.0022.67
    7ay=32284991.98x + 19998.061.000.97
    8ay=1358715.13x + 24016.241.00358.52
    下载: 导出CSV
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  • 细交链孢菌酮酸及其衍生物的合成与杀虫活性_化合物核磁共振谱图及色谱图.pdf
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出版历程
  • 收稿日期:  2021-07-16
  • 录用日期:  2021-08-08
  • 网络出版日期:  2022-03-06
  • 刊出日期:  2022-04-10

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