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Design, synthesis and fungicidal activities of phenazine-1-carboxamida conjugates of 1,3,4-thia(oxa)diazole

Min HE Jingwen GU Sicheng LI Xuwen XIANG Shan JIANG Zining CUI

何敏, 古景文, 李司丞, 向绪稳, 姜珊, 崔紫宁. 含1,3,4-噻 (噁) 二唑吩嗪-1-甲酰胺类衍生物的合成与杀菌活性[J]. 农药学学报, 2021, 23(2): 287-295. doi: 10.16801/j.issn.1008-7303.2021.0022
引用本文: 何敏, 古景文, 李司丞, 向绪稳, 姜珊, 崔紫宁. 含1,3,4-噻 (噁) 二唑吩嗪-1-甲酰胺类衍生物的合成与杀菌活性[J]. 农药学学报, 2021, 23(2): 287-295. doi: 10.16801/j.issn.1008-7303.2021.0022
Min HE, Jingwen GU, Sicheng LI, Xuwen XIANG, Shan JIANG, Zining CUI. Design, synthesis and fungicidal activities of phenazine-1-carboxamida conjugates of 1,3,4-thia(oxa)diazole[J]. Chinese Journal of Pesticide Science, 2021, 23(2): 287-295. doi: 10.16801/j.issn.1008-7303.2021.0022
Citation: Min HE, Jingwen GU, Sicheng LI, Xuwen XIANG, Shan JIANG, Zining CUI. Design, synthesis and fungicidal activities of phenazine-1-carboxamida conjugates of 1,3,4-thia(oxa)diazole[J]. Chinese Journal of Pesticide Science, 2021, 23(2): 287-295. doi: 10.16801/j.issn.1008-7303.2021.0022

含1,3,4-噻 (噁) 二唑吩嗪-1-甲酰胺类衍生物的合成与杀菌活性

doi: 10.16801/j.issn.1008-7303.2021.0022
详细信息
  • 中图分类号:  O626.2;TQ450.1

Design, synthesis and fungicidal activities of phenazine-1-carboxamida conjugates of 1,3,4-thia(oxa)diazole

Funds: the National Key Research and Development Program of China (2017YFD0200504); the National Natural Science Foundation of China (32072450, 31570122); the International Cooperation Special Project of Guangdong Province (2020A0505100048); the National Key Project for Basic Research (973 Program, 2015CB150600).
More Information
    Author Bio:

    # Equal contribution. #HE Min, female, postgraduate student, E-mail: 724832376@qq.com;

    #GU Jingwen, male, undergraduate student, E-mail: VinciGu653@outlook.com;

    #LI Sicheng, female, undergraduate student, E-mail: 1035433630@qq.com;

    Corresponding author: CUI Zining, author for correspondence, male, professor, engaged in molecular design and synthesis of new pesticides, E-mail: ziningcui@scau.edu.cn
  • 摘要: 对广泛存在于链霉菌和铜绿假单胞菌中的一种天然活性物质——申嗪霉素进行了结构修饰,合成了一系列高活性的含1,3,4-噻(噁)二唑的申嗪霉素衍生物 I 1 ~ I 28 。杀菌活性测定结果表明:所有目标化合物对禾谷镰刀菌具有较好的杀菌活性,均明显优于母体申嗪霉素。离体杀菌活性测定结果显示,化合物 I 8 (EC50 = 33.25 μg/mL)和化合物 I 22 (EC50 = 46.52 μg/mL)对禾谷镰刀菌的杀菌活性是申嗪霉素 (EC50 = 128.54 μg/mL)的3~4倍。活体杀菌活性显示,在500 μg/mL质量浓度下,化合物 I 8 (58.69%)和化合物 I 22 (55.37%)对禾谷镰刀菌的抑制率是申嗪霉素 (25.14%) 的两倍。构效关系分析结果表明,在苯环上引入吸电子基团对化合物的活性不利;而引入给电子基团则有利于提高其杀菌活性。同时,同一取代基在苯环上的取代位置依据活性的高低排列顺序为:邻位>对位>间位。这些结果可用于指导该类化合物的进一步结构改造。
  • 1.  The proposed synthetic route for the title compounds

    2.  The synthetic route of the novel phenazine-1-carboxylic acid derivatives

    Table  1.   Physical and chemical data of title compounds I1-I28

    Compd.XRAppearanceYield/%Elemental analysis (Calcd., %)
    CHN
    I1SHYellow solid8465.78(65.98)3.42(3.82)18.27(18.54)
    I2S2-ClYellow solid8260.36(60.12)2.89(3.04)16.76(16.53)
    I3S3-ClYellow solid9160.36(60.55)2.89(2.64)16.76(16.89)
    I4S4-ClYellow solid9060.36(60.60)2.89(3.01)16.76(16.49)
    I5S2-FYellow solid8962.83(62.99)3.01(3.22)17.45(17.19)
    I6S3-FYellow solid9062.83(62.61)3.01(2.86)17.45(17.68)
    I7S4-FYellow solid9362.83(63.03)3.01(3.25)17.45(17.27)
    I8S2-OCH3Yellow solid9463.91(64.12)3.66(3.87)16.94(16.72)
    I9S3-OCH3Yellow solid8863.91(63.82)3.66(3.49)16.94(17.11)
    I10S4-OCH3Yellow solid9363.91(64.19)3.66(3.92)16.94(16.71)
    I11S2-CH3Yellow solid9166.48(66.25)3.80(3.61)17.62(17.83)
    I12S3-CH3Yellow solid8966.48(66.66)3.80(3.98)17.62(17.48)
    I13S4-CH3Yellow solid9166.48(66.30)3.80(3.59)17.62(17.91)
    I14S4-CF3Yellow solid9058.53(58.75)2.68(2.41)15.51(15.68)
    I15OHYellow solid8868.66(68.79)3.57(3.38)19.06(19.29)
    I16O2-ClYellow solid8962.77(62.98)3.01(3.22)17.43(17.16)
    I17O3-ClYellow solid8862.77(63.01)3.01(2.86)17.43(17.24)
    I18O4-ClYellow solid9462.77(62.54)3.01(3.18)17.43(17.59)
    I19O2-FYellow solid9165.45(65.71)3.14(3.37)18.17(18.29)
    I20O3-FYellow solid8065.45(65.22)3.14(3.01)18.17(18.33)
    I21O4-FYellow solid8365.45(65.67)3.14(2.86)18.17(17.91)
    I22O2-OCH3Yellow solid8566.49(66.24)3.80(3.62)17.62(17.87)
    I23O3-OCH3Yellow solid8066.49(66.71)3.80(4.06)17.62(17.41)
    I24O4-OCH3Yellow solid8866.49(66.67)3.80(3.58)17.62(17.70)
    I25O2-CH3Yellow solid8169.28(69.01)3.96(4.15)18.36(18.24)
    I26O3-CH3Yellow solid8669.28(69.52)3.96(4.20)18.36(18.12)
    I27O4-CH3Yellow solid8869.28(69.45)3.96(3.75)18.36(18.54)
    I28O4-CF3Yellow solid8060.69(60.91)2.78(2.54)16.09(16.37)
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    Table  2.   1H NMR of title compounds I1-I28

    Compd.1H NMR (Chloroform-d, 400 MHz), δESI-MS
    I1 15.05 (s, 1H), 9.10 (dd, J = 7.2, 1.5 Hz, 1H), 8.54 (ddd, J = 7.7, 6.1, 1.5 Hz, 2H), 8.33 (dd, J = 8.6, 1.4 Hz, 1H), 8.10 – 8.00 (m, 4H), 8.00 – 7.94 (m, 1H), 7.50 (qd, J = 4.8, 1.6 Hz, 3H) 384.3
    I2 15.13 (s, 1H), 9.18 – 9.12 (m, 1H), 8.63 – 8.56 (m, 2H), 8.40 – 8.33 (m, 2H), 8.13 – 8.09 (m, 1H), 8.09 – 8.05 (m, 1H), 8.02 (ddd, J = 8.2, 6.7, 1.5 Hz, 1H), 7.58 (dt, J = 7.9, 3.1 Hz, 1H), 7.49 – 7.43 (m, 2H) 418.2
    I3 15.14 (s, 1H), 9.12 (dd, J = 7.2, 1.5 Hz, 1H), 8.61 – 8.53 (m, 2H), 8.38 – 8.32 (m, 1H), 8.12 – 8.03 (m, 3H), 8.00 (ddd, J = 8.3, 6.6, 1.6 Hz, 1H), 7.89 (dt, J = 6.4, 1.9 Hz, 1H), 7.49 – 7.42 (m, 2H) 418.3
    I4 15.10 (s, 1H), 8.32 (dd, J = 8.8, 1.5 Hz, 1H), 8.21 (dd, J = 7.9, 1.5 Hz, 1H), 8.03 – 7.97 (m, 1H), 7.81 – 7.73 (m, 3H), 7.65 (dd, J = 5.8, 3.4 Hz, 2H), 7.62 – 7.56 (m, 1H), 7.48 – 7.42 (m, 2H) 418.1
    I5 15.10 (s, 1H), 9.13 (dd, J = 7.1, 1.4 Hz, 1H), 8.61 – 8.52 (m, 2H), 8.44 (td, J = 7.6, 1.7 Hz, 1H), 8.38 – 8.31 (m, 1H), 8.12 – 8.06 (m, 1H), 8.06 – 8.02 (m, 1H), 8.00 (ddd, J = 8.2, 6.6, 1.5 Hz, 1H), 7.49 (tdd, J = 8.2, 4.8, 2.2 Hz, 1H), 7.33 (td, J = 7.8, 1.1Hz, 1H), 7.30 – 7.27 (m, 1H) 402.1
    I6 15.14 (s, 1H), 9.12 (dd, J = 7.1, 1.3 Hz, 1H), 8.70 – 8.45 (m, 2H), 8.41 – 8.29 (m, 1H), 8.14 – 7.91 (m, 3H), 7.88 – 7.70 (m, 2H), 7.48 (td, J = 7.9, 5.8 Hz, 1H), 7.22 – 7.15 (m, 1H) 402.3
    I7 15.10 (s, 1H), 9.12 (d, J = 6.9 Hz, 1H), 8.62 – 8.48 (m, 2H), 8.35 (d, J = 8.3 Hz, 1H), 8.03 (tt, J = 13.6, 7.5 Hz, 5H), 7.21 (t, J = 8.5 Hz, 2H) 402.2
    I8 15.01 (s, 1H), 9.15 (dd, J = 7.1, 1.5 Hz, 1H), 8.63 – 8.53 (m, 3H), 8.40 – 8.32 (m, 1H), 8.13 – 8.02 (m, 2H), 8.02 – 7.97 (m, 1H), 7.54 – 7.45 (m, 1H), 7.17 (td, J = 7.6, 1.1 Hz, 1H), 7.10 (dd, J = 8.4, 1.1 Hz, 1H), 4.12 (s, 3H) 414.4
    I9 15.09 (s, 1H), 9.12 (dd, J = 7.1, 1.5 Hz, 1H), 8.61 – 8.51 (m, 2H), 8.38 – 8.31 (m, 1H), 8.12 – 7.95 (m, 3H), 7.64 (t, J = 2.0 Hz, 1H), 7.58 (d, J = 7.6 Hz, 1H), 7.41 (t, J = 7.9 Hz, 1H), 7.04 (dd, J = 8.3, 2.6 Hz, 1H), 3.92 (s, 3H) 414.1
    I10 15.01 (s, 1H), 9.11 (dd, J = 7.2, 1.5 Hz, 1H), 8.59 – 8.50 (m, 2H), 8.37 – 8.30 (m, 1H), 8.10 – 7.93 (m, 5H), 7.06 – 6.98 (m, 2H), 3.89 (s, 3H) 414.3
    I11 15.11 (s, 1H), 9.16 – 9.10 (m, 1H), 8.62 – 8.53 (m, 2H), 8.40 – 8.30 (m, 1H), 8.12 – 7.98 (m, 3H), 7.79 (d, J = 7.5 Hz, 1H), 7.46 – 7.32 (m, 3H), 2.70 (s, 3H) 398.4
    I12 15.04 (s, 1H), 9.11 (dd, J = 7.2, 1.5 Hz, 1H), 8.56 (ddd, J = 8.9, 3.4, 1.4 Hz, 2H), 8.38 – 8.30 (m, 1H), 8.11 – 8.02 (m, 2H), 7.99 (ddd, J = 8.3, 6.6, 1.5 Hz, 1H), 7.90 – 7.79 (m, 2H), 7.39 (t, J = 7.6 Hz, 1H), 7.30 (d, J = 7.7 Hz, 1H), 2.46 (s, 3H) 398.1
    I13 15.02 (s, 1H), 9.10 (dd, J = 7.2, 1.5 Hz, 1H), 8.54 (ddd, J = 8.6, 4.7, 1.5 Hz, 2H), 8.36 – 8.29 (m, 1H), 8.08 – 8.05 (m, 1H), 8.05 – 8.01 (m, 1H), 7.98 (ddd, J = 8.2, 6.6, 1.6 Hz, 1H), 7.92 (d, J = 7.9 Hz, 2H), 7.30 (d, J = 7.9 Hz, 2H), 2.43 (s, 3H) 398.2
    I14 15.19 (s, 1H), 9.12 (dd, J = 7.2, 1.5 Hz, 1H), 8.62 – 8.51 (m, 2H), 8.41 – 8.31 (m, 1H), 8.16 (d, J = 8.1 Hz, 2H), 8.13 – 7.96 (m, 3H), 7.78 (d, J = 8.1 Hz, 2H) 452.3
    I15 8.46 (dd, J = 8.7, 1.4 Hz, 1H), 8.39 (s, 1H), 8.31 – 8.23 (m, 1H), 8.21 – 8.14 (m, 1H), 8.04 (dd, J = 6.9, 1.4 Hz, 1H), 7.95 (dd, J = 8.7, 6.8 Hz,1H), 7.85 (dddd, J = 21.6, 8.2, 6.6, 1.5 Hz, 2H), 7.64 – 7.56 (m, 2H), 7.49 – 7.40 (m, 1H), 7.40 – 7.26 (m, 2H) 368.3
    I16 14.84 (s, 1H), 9.14 (dd, J = 7.1, 1.5 Hz, 1H), 8.57 (dd, J = 8.7, 1.5 Hz, 1H), 8.46 – 8.38 (m, 1H), 8.38 – 8.31 (m, 1H), 8.14 – 7.95 (m, 4H), 7.59 (dd, J = 7.9, 1.5 Hz, 1H), 7.55 – 7.40 (m, 2H) 402.2
    I17 8.47 (dd, J = 8.7, 1.4 Hz, 1H), 8.41 (s, 1H), 8.31 – 8.25 (m, 1H), 8.20 – 8.13 (m, 1H), 8.04 (dd, J = 6.8, 1.4 Hz, 1H), 7.95 (dd, J = 8.7, 6.9Hz, 1H), 7.86 (dddd, J = 20.8, 8.2, 6.6, 1.4 Hz, 2H), 7.57 (t, J = 1.7 Hz, 1H), 7.50 (dt, J = 7.8, 1.2 Hz, 1H), 7.41 (ddd, J = 8.0, 2.0, 1.0 Hz, 1H), 7.28 (d, J = 8.1 Hz, 1H) 402.3
    I18 14.80 (s, 1H), 9.13 (dt, J = 7.2, 1.2 Hz, 1H), 8.57 (dt, J = 8.6, 1.1 Hz, 1H), 8.44 (dd, J = 8.2, 1.5 Hz, 1H), 8.35 (dd, J = 8.7, 1.5 Hz, 1H), 8.14 – 7.95 (m, 5H), 7.56 – 7.48 (m, 2H) 402.2
    I19 14.81 (s, 1H), 9.15 (dd, J = 7.2, 1.5 Hz, 1H), 8.57 (dd, J = 8.7, 1.5 Hz, 1H), 8.47 – 8.39 (m, 1H), 8.39 – 8.31 (m, 1H), 8.23 – 8.12 (m, 1H), 8.12 – 7.95 (m, 3H), 7.56 (dddd, J = 8.4, 7.4, 5.0, 1.8 Hz, 1H), 7.36 – 7.31 (m, 1H), 7.31 – 7.27 (m, 1H) 386.2
    I20 14.82 (s, 1H), 9.14 (dd, J = 7.1, 1.4 Hz, 1H), 8.58 (dd, J = 8.7, 1.4 Hz, 1H), 8.47 – 8.42 (m, 1H), 8.38 – 8.34 (m, 1H), 8.12 – 7.94 (m, 4H), 7.87 (dt, J = 9.2, 2.3 Hz, 1H), 7.53 (td, J = 7.9, 5.6 Hz, 1H), 7.24 (d, J = 1.8 Hz, 2H) 386.3
    I21 14.77 (s, 1H), 9.14 (dd, J = 7.2, 1.5 Hz, 1H), 8.58 (dd, J = 8.7, 1.5 Hz, 1H), 8.50 – 8.41 (m, 1H), 8.40 – 8.32 (m, 1H), 8.17 (ddd, J = 9.9, 5.2, 2.5 Hz, 2H), 8.12 – 7.96 (m, 3H), 7.23 (d, J = 8.6 Hz, 2H) 386.3
    I22 8.44 (dd, J = 8.8, 1.3 Hz, 1H), 8.34 – 8.23 (m, 2H), 8.22 – 8.15 (m, 1H), 8.10 (dd, J = 6.8, 1.3 Hz, 1H), 7.98 – 7.78 (m, 3H), 7.54 (dd, J = 7.8, 1.7 Hz, 1H), 7.41 – 7.32 (m, 1H), 6.89 (td, J = 7.8, 0.8 Hz, 1H), 6.77 (d, J = 8.4 Hz, 1H), 3.24 (s, 3H) 398.4
    I23 14.74 (s, 1H), 9.15 (dd, J = 7.2, 1.5 Hz, 1H), 8.57 (dd, J = 8.7, 1.5 Hz, 1H), 8.49 – 8.41 (m, 1H), 8.40 – 8.32 (m, 1H), 8.14 – 7.95 (m, 3H), 7.81 – 7.66 (m, 2H), 7.45 (t, J = 8.0 Hz, 1H), 7.12 – 7.06 (m, 1H), 3.93 (s, 3H) 398.3
    I24 14.67 (s, 1H), 9.14 (dd, J = 7.2, 1.5 Hz, 1H), 8.56 (dd, J = 8.7, 1.5 Hz, 1H), 8.48 – 8.41 (m, 1H), 8.39 – 8.32 (m, 1H), 8.15 – 7.95 (m, 5H), 7.04 (d, J = 8.9 Hz, 2H), 3.91 (s, 3H) 398.2
    I25 8.45 (dd, J = 8.7, 1.4 Hz, 1H), 8.38 (s, 1H), 8.30 – 8.23 (m, 1H), 8.21 – 8.13 (m, 1H), 8.04 (dd, J = 6.8, 1.4 Hz, 1H), 7.99 – 7.93 (m, 1H), 7.93 – 7.84 (m, 1H), 7.82 (ddd, J = 8.2, 6.6, 1.5 Hz, 1H), 7.49 (d, J = 8.3 Hz, 2H), 7.10 (s, 2H), 2.32 (s, 3H) 382.2
    I26 8.46 (dd, J = 8.7, 1.4 Hz, 1H), 8.38 (s, 1H), 8.30 – 8.23 (m, 1H), 8.22 – 8.14 (m, 1H), 8.04 (dd, J = 6.8, 1.4 Hz, 1H), 7.95 (dd, J = 8.7, 6.8 Hz, 1H), 7.85 (dddd, J = 21.2, 8.2, 6.6, 1.5 Hz, 2H), 7.41 (dd, J = 4.3, 1.8 Hz, 2H), 7.21 (q, J = 8.2, 7.8 Hz, 2H), 2.26 (s, 3H) 382.3
    I27 8.45 (dd, J = 8.8, 1.4 Hz, 1H), 8.38 (s, 1H), 8.30 – 8.23 (m, 1H), 8.21 – 8.13 (m, 1H), 8.04 (dd, J = 6.8, 1.4 Hz, 1H), 7.94 (dd, J = 8.7, 6.8 Hz, 1H), 7.84 (dddd, J = 21.8, 8.2, 6.6, 1.5 Hz, 2H), 7.48 (d, J = 8.3 Hz, 2H), 7.11 (d, J = 8.1 Hz, 2H), 2.32 (s, 3H) 382.3
    I28 14.88 (s, 1H), 9.13 (dd, J = 7.2, 1.5 Hz, 1H), 8.58 (dd, J = 8.7, 1.5 Hz, 1H), 8.52 – 8.40 (m, 1H), 8.39 – 8.32 (m, 1H), 8.32 – 8.26 (m, 2H), 8.13 – 7.96 (m, 3H), 7.85 – 7.77 (m, 2H) 436.2
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    Table  3.   EC50 values (μg/mL) against M. oryzae, B. cinerea, P. capsici, R. solani and F. graminearum

    Compd.F. graminearumP. capsiciR. solaniM. oryzaeB.cinerea
    PCA128.54 ± 4.687.26 ± 1.057.56 ± 0.9912.63 ± 1.1419.76 ± 1.31
    I171.25 ± 2.9558.17 ± 3.1252.45 ± 1.9665.21 ± 2.8978.15 ± 2.65
    I278.23 ± 3.0367.15 ± 2.2464.89 ± 2.0372.15 ± 2.3589.54 ± 3.01
    I399.45 ± 4.0889.25 ± 3.1784.36 ± 3.0892.14 ± 3.12102.47 ± 4.01
    I486.12 ± 4.1168.58 ± 2.6472.78 ± 2.6178.56 ± 3.1490.13 ± 3.12
    I574.12 ± 3.2672.34 ± 2.9869.78 ± 2.3568.47 ± 2.5890.65 ± 2.99
    I698.31 ± 3.4689.17 ± 3.2297.54 ± 3.9789.22 ± 2.64120.34 ± 3.25
    I780.24 ± 3.9580.57 ± 2.9975.81 ± 2.6880.17 ± 2.9998.54 ± 3.13
    I833.25 ± 2.0631.25 ± 2.018.64 ± 1.1125.23 ± 1.9546.28 ± 2.01
    I962.48 ± 3.1154.27 ± 2.6134.62 ± 2.0656.47 ± 2.0871.56 ± 2.56
    I1049.47 ± 2.3539.46 ± 1.9415.78 ± 1.6442.13 ± 1.9761.54 ± 2.11
    I1145.95 ± 2.2141.03 ± 1.9624.38 ± 1.9835.48 ± 1.3452.47 ± 1.98
    I1267.36 ± 3.1255.36 ± 1.3349.31 ± 2.0865.78 ± 2.5477.67 ± 2.31
    I1350.49 ± 2.6849.55 ± 1.6540.27 ± 2.3155.87 ± 2.3170.15 ± 1.96
    I1484.12 ± 3.02125.34 ± 4.7482.06 ± 3.2180.49 ± 3.21128.56 ± 4.56
    I1566.39 ± 2.4654.23 ± 2.0352.38 ± 2.2649.34 ± 2.3165.72 ± 1.98
    I1670.23 ± 2.3457.35 ± 1.6561.26 ± 3.0650.23 ± 2.2268.23 ± 2.35
    I1785.34 ± 3.0568.14 ± 2.3775.34 ± 2.6161.58 ± 2.6180.66 ± 3.14
    I1876.55 ± 2.6160.89 ± 2.1663.33 ± 2.3952.36 ± 2.1374.13 ± 3.02
    I1975.06 ± 2.8060.37 ± 2.3155.14 ± 2.1153.57 ± 1.9870.56 ± 2.68
    I2089.61 ± 3.2271.24 ± 3.0469.46 ± 2.4963.89 ± 3.0186.49 ± 3.28
    I2180.07 ± 2.6765.81 ± 2.6860.18 ± 2.6552.38 ± 2.4178.05 ± 2.66
    I2246.52 ± 3.547.24 ± 1.0126.16 ± 2.0116.56 ± 1.3445.08 ± 2.05
    I2353.53 ± 2.6734.51 ± 2.6840.23 ± 2.1342.34 ± 1.9659.23 ± 2.34
    I2449.97 ± 2.3922.37 ± 1.6736.72 ± 1.9431.43 ± 1.9952.11 ± 2.16
    I2556.48 ± 2.0330.64 ± 2.5348.83 ± 2.5336.54 ± 1.2544.54 ± 2.25
    I2653.13 ± 2.1524.35 ± 1.8430.22 ± 1.8334.13 ± 1.6751.37 ± 1.99
    I2762.08 ± 3.1549.72 ± 2.3846.57 ± 2.0546.31 ± 2.0560.52 ± 1.97
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    Table  4.   Fungicidal activity of compounds against five plant fungi in vivo at 500 μg/mL (inhibition rate/%)

    Compd.F. graminearumP. capsiciR. solaniM. oryzaeB.cinerea
    PCA 25.14 ± 0.86 93.48 ± 1.67 90.25 ± 1.69 92.18 ± 1.63 80.57 ± 1.35
    I1 45.68 ± 1.03 48.21 ± 1.07 60.23 ± 1.36 52.14 ± 1.02 35.21 ± 0.98
    I8 58.69 ± 1.14 66.89 ± 1.32 91.34 ± 1.58 69.38 ± 1.34 63.45 ± 1.37
    I9 45.69 ± 1.03 50.23 ± 1.24 69.16 ± 1.35 52.33 ± 1.20 40.12 ± 1.25
    I10 50.39 ± 1.31 59.21 ± 1.38 77.59 ± 1.63 62.55 ± 1.36 45.68 ± 1.34
    I11 52.61 ± 1.22 60.33 ± 1.39 68.28 ± 1.29 68.16 ± 1.64 56.95 ± 1.54
    I12 44.33 ± 0.99 49.62 ± 1.09 60.14 ± 1.46 44.83 ± 1.04 36.49 ± 0.99
    I13 49.61 ± 1.21 55.97 ± 1.22 63.21 ± 1.43 45.82 ± 1.11 40.55 ± 1.06
    I15 40.46 ± 1.11 50.29 ± 1.62 45.86 ± 1.03 50.23 ± 1.22 32.56 ± 1.02
    I22 55.37 ± 1.37 94.23 ± 1.98 76.38 ± 1.38 85.94 ± 1.86 48.37 ± 1.23
    I23 43.66 ± 1.35 64.55 ± 1.32 55.67 ± 1.61 56.28 ± 1.32 42.28 ± 1.09
    I24 50.15 ± 2.01 70.54 ± 1.54 62.13 ± 1.30 60.71 ± 1.56 45.68 ± 1.37
    I25 42.68 ± 1.35 70.61 ± 1.60 66.71 ± 1.65 62.13 ± 1.34 42.88 ± 1.26
    I26 35.27 ± 0.97 52.68 ± 1.34 51.46 ± 1.05 51.04 ± 1.05 38.98 ± 0.99
    I27 40.57 ± 1.09 60.11 ± 1.75 60.57 ± 1.62 56.69 ± 1.18 41.21 ± 1.21
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  • 1HNMR spectra of the compounds I1-I28.doc
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  • 收稿日期:  2020-09-05
  • 录用日期:  2020-11-07
  • 刊出日期:  2021-04-10

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