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三氟羧草醚类似物的合成及除草活性

赵卓然 李佳康 李占斌 陈雨 黄玉乾 李文琪 姬志勤 魏少鹏

赵卓然, 李佳康, 李占斌, 陈雨, 黄玉乾, 李文琪, 姬志勤, 魏少鹏. 三氟羧草醚类似物的合成及除草活性[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2022.0019
引用本文: 赵卓然, 李佳康, 李占斌, 陈雨, 黄玉乾, 李文琪, 姬志勤, 魏少鹏. 三氟羧草醚类似物的合成及除草活性[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2022.0019
ZHAO Zhuoran, LI Jiakang, LI Zhanbin, CHEN Yu, HUANG Yuqian, LI Wenqi, JI Zhiqin, WEI Shaopeng. Synthesis and herbicidal activity of acifluorfen analogues[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2022.0019
Citation: ZHAO Zhuoran, LI Jiakang, LI Zhanbin, CHEN Yu, HUANG Yuqian, LI Wenqi, JI Zhiqin, WEI Shaopeng. Synthesis and herbicidal activity of acifluorfen analogues[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2022.0019

三氟羧草醚类似物的合成及除草活性

doi: 10.16801/j.issn.1008-7303.2022.0019
基金项目: 国家自然科学基金(31872011).
详细信息
    作者简介:

    赵卓然,zhaozhuoran@nwafu.edu.cn

    通讯作者:

    魏少鹏,weishaopeng@nwsuaf.edu.cn.

  • 中图分类号: O625.5;TQ450.11

Synthesis and herbicidal activity of acifluorfen analogues

Funds: the National Natural Science Foundation of China (31872011).
  • 摘要: 以2,5-二羟基苯甲酸甲酯和三氟羧草醚为起始原料,设计合成了3个系列20个新的三氟羧草醚类似物,通过核磁共振氢谱、碳谱对其结构进行了表征。分别采用小杯法和室内盆栽法测定了目标化合物的除草活性。结果表明,化合物 III-02 [5-(2-氯-4-三氟甲基苯氧基)-2-硝基苯甲酸-(6-甲基苯并噻唑-2-基)酯]对单子叶杂草的除草活性明显高于对照药剂三氟羧草醚,其对稗草Echinochloa crusgalli和马唐Digitaria sanguinalis根茎生长的EC50值分别为2.03、0.93 μg/mL和1.49、0.52 μg/mL;在有效成分100 g/hm2的施药剂量下,化合物 III-02 对单子叶杂草稗草、马唐及狗尾草Setaria viridis的防治效果均在85%以上,明显高于三氟羧草醚,对阔叶杂草马齿苋Portulaca oleracea、反枝苋Amaranthus retroflexus及苘麻Abutilon theophrasti的防治效果可达100%。初步构效关系表明,2-硝基苯甲酰衍生物的除草活性明显优于其2-甲氧基衍生物,三氟羧草醚苯甲酸酯衍生物对单子叶杂草的除草活性明显高于其苯甲酰胺衍生物。
  • 1  化合物A27、I-00、氟吡酰草胺和三氟羧草醚的化学结构式

    1.  The structural formulas of A27, I-00, picolinafen and acifluorfen

    2  目标化合物I-01~I-06的合成路线

    2.  The synthetic routes of target compounds I-01 to I-06

    3  目标化合物II-01~II-10和III-01~III-04的合成路线

    3.  The synthetic routes of target compounds II-01 to II-10 and III-01 to III-04

    表  1  目标化合物中取代基R的结构

    Table  1.   The structural formulas of target compounds

    化合物
    Compd.
    R化合物
    Compd.
    R化合物
    Compd.
    R化合物
    Compd.
    R
    I-01 I-06 II-05 4-Cl II-10 6-Br
    I-02 II-01 II-06 6-Me III-01 H
    I-03 II-02 H II-07 6-OMe III-02 6-Me
    I-04 II-03 4-Me II-08 6-OEt III-03 6-Cl
    I-05 II-04 4-OMe II-09 6-Cl III-04 6-Br
    下载: 导出CSV

    表  2  目标化合物在5.0 μg/mL下的除草活性 (小杯法)

    Table  2.   Herbicidal activities of target compounds at 5.0 μg/mL (petri dish assay)

    化合物
    Compounds
    抑制率 Inhibition rate/%*
    稗草
    E. crusgalli
    马唐
    D. sanguinalis
    马齿苋
    P. oleracea
    野油菜
    B. juncea
    根/茎
    Root/Stem
    根/茎
    Root/Stem
    根/茎
    Root/Stem
    根/茎
    Root/Stem
    I-013.2/8.64.8/11.914.5/30.917.2/31.1
    I-022.3/7.12.0/5.612.9/36.820.7/49.8
    I-031.7/5.13.7/8.46.7/21.510.9/25.6
    I-043.5/9.97.2/17.116.3/40.126.5/58.8
    I-050.2/1.24.7/9.315.0/39.45.9/21.5
    I-061.6/4.52.5/6.66.2/23.33.5/9.3
    II-0113.2/34.085.0/93.4100/10096.9/97.6
    II-024.3/11.710.3/19.2100/10096.2/100
    II-030.2/1.32.7/6.511.8/30.210.4/29.9
    II-045.9/20.63.8/9.180.3/85.989.2/94.5
    II-051.0/3.23.0/6.723.8/58.532.6/69.4
    II-062.8/9.113.9/22.098.3/99.2100/100
    II-076.5/22.65.2/11.110.4/36.812.5/41.9
    II-084.7/20.30.2/1.271.7/75.977.2/79.2
    II-095.6/13.56.2/15.920.2/46.522.8/54.9
    II-103.3/12.810.8/22.280.6/83.997.0/97.5
    III-0110.8/32.187.2/91.4100/100100/100
    III-0272.7/85.590.3/96.9100/100100/100
    III-0320.6/42.916.0/41.2100/100100/100
    III-0459.8/74.676.5/87.9100/100100/100
    三氟羧草醚
    acifluorfen
    52.5/64.747.7/65.8100/100100/100
    注:*表中数据为 3 次重复平均值。Note: * The data in the table is the average of the three repeats.
    下载: 导出CSV

    表  3  部分化合物对四种供试杂草的EC50

    Table  3.   EC50 value of selected compounds against four tested weeds

    化合物
    Compound
    EC50 值 (95% 置信区间)
    EC50 value (95% confidence interval)/(μg/mL)
    稗草 E. crusgalli马唐 D. sanguinalis马齿苋 P. oleracea野油菜 B. juncea
    II-01 茎 Stem 7.48(5.67~9.88) 1.14(0.99~1.31) 0.14(0.11~0.18) 0.50(0.40~0.63)
    根 Root 12.56(11.51~13.72) 1.67(1.45~1.92) 0.23(0.18~0.30) 0.54(0.42~0.71)
    III-01 茎 Stem 8.60(6.65~11.12) 1.46(1.28~1.66) 0.12(0.10~0.15) 0.38(0.29~0.50)
    根 Root 13.13(12.03~14.34) 1.53(1.33~1.77) 0.20(0.16~0.24) 0.43(0.35~0.54)
    III-02 茎 Stem 0.93(0.74~1.17) 0.52(0.43~0.63) 0.07(0.06~0.09) 0.26(0.20~0.35)
    根 Root 2.03(1.71~2.42) 1.49(1.30~1.70) 0.14(0.11~0.18) 0.32(0.25~0.41)
    III-03 茎 Stem 5.88(4.78~7.23) 6.38(4.85~8.40) 0.21(0.16~0.26) 0.61(0.49~0.75)
    根 Root 10.72(9.68~11.87) 15.90(13.88~18.25) 0.21(0.17~0.27) 0.62(0.49~0.79)
    III-04 茎 Stem 1.97(1.59~2.43) 2.03(1.79~2.31) 0.10(0.08~0.12) 0.34(0.27~0.42)
    根 Root 3.61(3.10~4.19) 3.77(3.41~4.17) 0.18(0.15~0.23) 0.42(0.32~0.54)
    三氟羧草醚
    acifluorfen
    茎 Stem 3.29(2.88~3.77) 3.92(3.45~4.44) 0.09(0.07~0.11) 0.31(0.24~0.39)
    根 Root 4.33(3.67~5.11) 5.77(4.94~6.75) 0.17(0.14~0.20) 0.35(0.28~0.44)
    下载: 导出CSV

    表  4  部分化合物苗后处理的除草活性

    Table  4.   Post-emergence herbicidal activity of selected compounds

    化合物
    Compound
    剂量
    Dose, a.i./
    (g/hm2)
    防治效果 Control efficacy/%
    稗草
    E. crusgalli
    马唐
    D. sanguinalis
    狗尾草
    S. viridis
    马齿苋
    P. oleracea
    反枝苋
    A. retroflexus
    苘麻
    A. theophrasti
    II-01 100 41.2 ± 2.1 f 87.4 ± 1.2 bc 58.1 ± 2.2 d 85.2 ± 2.0 b 75.2 ± 2.5 c 80.8 ± 2.4 d
    50 23.3 ± 1.8 g 73.3 ± 1.9 d 41.3 ± 3.8 f 73.6 ± 3.2 c 66.3 ± 1.8 d 71.2 ± 2.3 e
    III-01 100 43.0 ± 2.1 f 82.7 ± 2.0 c 44.4 ± 3.4 f 100 ± 0.0 a 100 ± 0.0 a 91.2 ± 1.5 c
    50 20.5 ± 1.3 g 72.1 ± 1.6 d 33.4 ± 2.2 g 100 ± 0.0 a 100 ± 0.0 a 79.5 ± 2.3 d
    III-02 100 88.7 ± 1.2 a 92.8 ± 2.5 a 87.5 ± 2.4 a 100 ± 0.0 a 100 ± 0.0 a 100 ± 0.0 a
    50 74.0 ± 3.1 b 89.6 ± 1.6 ab 73.2 ± 2.8 b 100 ± 0.0 a 100 ± 0.0 a 100 ± 0.0 a
    III-03 100 51.9 ± 1.7 e 52.1 ± 3.6 f 50.2 ± 2.3 e 100 ± 0.0 a 87.9 ± 1.4 b 91.1 ± 3.1 c
    50 43.1 ± 2.4 f 45.5 ± 2.5 g 42.1 ± 1.4 f 100 ± 0.0 a 72.0 ± 2.1 c 81.2 ± 1.7 d
    III-04 100 76.1 ± 1.5 b 75.5 ± 2.7 d 65.1 ± 3.7 c 100 ± 0.0 a 96.9 ± 3.3 a 93.7 ± 2.7 bc
    50 60.6 ± 2.3 d 62.6 ± 2.1 e 53.5 ± 1.9 de 100 ± 0.0 a 87.8 ± 3.0 b 83.0 ± 2.4 d
    三氟羧草醚
    acifluorfen
    100 64.9 ± 1.6 c 86.3 ± 2.5 bc 69.4 ± 1.1 bc 100 ± 0.0 a 100 ± 0.0 a 100 ± 0.0 a
    50 53.7 ± 1.2 e 70.8 ± 1.6 d 53.9 ± 2.0 de 100 ± 0.0 a 100 ± 0.0 a 96.6 ± 2.6 ab
    注: 表中数据为 3 次重复平均值 ± 标准偏差。不同字母表示经Duncan’s新复极差测验, 在 P0.05 水平差异显著。
    Note: Data in the table are mean ± SD, and repeated for three times. Different letters indicate that there are significant differences at the level of P0.05 after Duncan’s multiple range test.
    下载: 导出CSV
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  • 收稿日期:  2021-11-03
  • 录用日期:  2022-01-21
  • 网络出版日期:  2022-03-01

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