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含环丙甲酸类活性片段的新型二酰胺衍生物的设计、合成及生物活性

陈睿嘉 冯婷婷 王港澳 徐晓勇 李忠

陈睿嘉, 冯婷婷, 王港澳, 徐晓勇, 李忠. 含环丙甲酸类活性片段的新型二酰胺衍生物的设计、合成及生物活性[J]. 农药学学报, 2022, 24(2): 248-259. doi: 10.16801/j.issn.1008-7303.2021.0160
引用本文: 陈睿嘉, 冯婷婷, 王港澳, 徐晓勇, 李忠. 含环丙甲酸类活性片段的新型二酰胺衍生物的设计、合成及生物活性[J]. 农药学学报, 2022, 24(2): 248-259. doi: 10.16801/j.issn.1008-7303.2021.0160
CHEN Ruijia, FENG Tingting, WANG Gang'ao, XU Xiaoyong, LI Zhong. Design, synthesis and biological activities of novel diamide derivatives containing bioactive cyclopropanecarboxylic acid fragments[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 248-259. doi: 10.16801/j.issn.1008-7303.2021.0160
Citation: CHEN Ruijia, FENG Tingting, WANG Gang'ao, XU Xiaoyong, LI Zhong. Design, synthesis and biological activities of novel diamide derivatives containing bioactive cyclopropanecarboxylic acid fragments[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 248-259. doi: 10.16801/j.issn.1008-7303.2021.0160

含环丙甲酸类活性片段的新型二酰胺衍生物的设计、合成及生物活性

doi: 10.16801/j.issn.1008-7303.2021.0160
基金项目: 国家重点研发计划(2017YFD0200505).
详细信息
    作者简介:

    陈睿嘉,chenruijia_ecust@163.com

    通讯作者:

    李忠,lizhong@ecust.edu.cn.

  • 中图分类号: O624.5;O623.626;TQ450.11

Design, synthesis and biological activities of novel diamide derivatives containing bioactive cyclopropanecarboxylic acid fragments

Funds: the National Key Research and Development Program of China (2017YFD0200505)
  • 摘要: 为探索具有新颖结构的杀虫剂先导,将多种含环丙甲酸的活性片段引入二酰胺类杀虫剂,设计并合成了21个新型的二酰胺类衍生物,其结构均经过核磁共振波谱 (NMR)及高分辨质谱 (HRMS)表征。测试了所有目标衍生物对苜蓿蚜Aphis craccivora、东方黏虫Mythimna separate、小麦赤霉病菌Fusarium graminearum及小麦白粉病菌Blumeria graminis的生物活性。结果显示:大部分邻位二酰胺类衍生物的对两种供试病原菌的杀菌活性不够理想,而对两种害虫靶标均有良好的杀虫活性。在500 mg/L质量浓度下,衍生物 10h 对苜蓿蚜的致死率为90%, 10k 对东方黏虫的致死率达100%,这两个衍生物均可作为潜在的杀虫先导衍生物加以进一步研究。
  • 1  具有生物活性的二酰胺类衍生物

    1.  Diamides with biological activities

    2  含环丙甲酸片段的天然产物、药物及农药

    2.  Natural products, drugs and pesticides containing cyclopropanecarboxylic acid fragments

    3  目标衍生物的分子设计

    3.  Molecular design of target derivatives

    4  目标衍生物的合成路线

    4.  Synthetic routes of target derivatives

    表  1  500 mg/L下8a~8c、9a~9c和10a~10c对4种靶标的杀虫或杀菌活性

    Table  1.   The insecticidal or fungicidal activities against 4 targets of 8a-8c, 9a-9c and 10a-10c at 500 mg/L

    衍生物
    Derative
    结构通式
    General structure
    R1死亡率c
    Mortality ratec/%
    抑制率
    Inhibitory rate/%
    苜蓿蚜
    A. craccivora
    东方黏虫
    M. separate
    小麦赤霉病菌
    F. graminearum
    小麦白粉病菌
    B. graminis
    8a 20 15 10 0
    8b a 50 0 15 5
    8c 20 5 5 0
    9a 0 0 40 0
    9b a 35 10 35 20
    9c 25 30 30 50
    10a 20 65 15 0
    10b a 60 25 35 0
    10c 25 45 20 0
    高效氯氟氰菊酯b lambda-cyhalothrin b 100
    氯虫苯甲酰胺b chlorantraniliprole b 100
    氰烯菌酯b phenamacril b 100
    戊唑醇b tebuconazole b 100
    注:a 衍生物为消旋体,此处结构式为相对构型。b 作为阳性对照的氯虫苯甲酰胺、高效氯氟氰菊酯、氰烯菌酯和戊唑醇测试浓度均为100 mg/L。c 对两种害虫靶标的空白对照的死亡率为0。Note: a The derivitives were racemic, and relative configurations were shown. b Chlorantraniliprole, lambda-cyhalothrin, phenamacril and tebuconazole were tested at 100 mg/L. c The mortality rate of blank control were both zero for the 2 insect targets.
    下载: 导出CSV

    表  2  10d~10o对4种靶标的杀虫或杀菌活性

    Table  2.   The insecticidal and fungicidal activities against 4 targets of 10d-10o

    衍生物
    Deriv.
    R1含该活性片段的   
    代表性药物或农药   
    Representative drug    
    or pesticide containing    
    this bioactive fragment   
    质量浓度
    Conc./
    (mg/L)
    致死率b
    Mortalityb/%
    抑制率
    Inhibitory rate/%
    苜蓿蚜
    A. craccivora
    东方黏虫
    M. separate
    小麦赤霉病菌
    F. graminearum
    小麦白粉病菌
    B. graminis
    10d a 西司他丁 cilastatin 500 25 30 5 0
    10e 甲氰菊酯 fenpropathrin 500 10 15 20 5
    10f a 胺菊酯 tetramethrin 500 70 20 30 10
    10g a 氯菊酯 permethrin 500 75 25 20 5
    10h a 高效氯氟氰菊酯 lambda-cyhalothrin 500 90 40 15 0
    200 55
    10i a 氟氯苯菊酯 bayticol 500 65 30 35 15
    10j RO5444101 500 15 40 10 0
    10k RO5459072 [22] 500 10 100 15 0
    200 70
    10l VH298 [23] 500 10 80 5 0
    200 20
    10m VZ185 [24] 500 25 35 25 15
    10n 鲁玛卡托 lumacaftor 500 15 65 35 10
    10o a 仑布雷生 lemborexant 500 30 40 45 20
    高效氯氟氰菊酯 lambda-cyhalothrin 100 100
    氯虫苯甲酰胺 chlorantraniliprole 100 100
    氰烯菌酯 phenamacril 100 100
    戊唑醇 tebuconazole 100 100
    注:a衍生物为消旋体,此处结构式为相对构型。b对两害虫靶标的空白对照的死亡率为0。Note: a The derivitives were racemic and relative configurations were shown. b The mortality rate of blank control were both zero for the 2 insect targets.
    下载: 导出CSV
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出版历程
  • 收稿日期:  2021-09-04
  • 录用日期:  2021-10-12
  • 网络出版日期:  2021-10-26
  • 刊出日期:  2022-04-10

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