Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 309-315.DOI: 10.6023/cjoc202307014 Previous Articles     Next Articles


黄志友a, 杨平a, 何波b,*(), 欧文霞a, 袁思雨a   

  1. a 邵阳学院农林生态学院 湖南邵阳 422000
    b 南京农业大学植物保护学院 农作物生物灾害综合治理教育部重点实验室 南京 210095
  • 收稿日期:2023-07-15 修回日期:2023-08-19 发布日期:2023-09-28
  • 基金资助:
    湖南省自然科学基金青年(2021JJ40515); 湖南省教育厅优秀青年(21B0677)

Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

Zhiyou Huanga, Ping Yanga, Bo Heb(), Wenxia Oua, Siyu Yuana   

  1. a College of Agriculture Forestry Ecology, Shaoyang University, Shaoyang 422000
    b Key Laboratory of Integrated Management of Crop Disease and Pests, Ministry of Education, College of Plant Protection, Nanjing Agricultural University, Nanjing 210095
  • Received:2023-07-15 Revised:2023-08-19 Published:2023-09-28
  • Contact: *E-mail:
  • Supported by:
    Natural Science Foundation of Hunan Province Youth Project(2021JJ40515); Scientific Research Fund of Hunan Provincial Education Department(21B0677)

In order to obtain novel abscisic acid analogues, morpholine-sulfonamide compound was designed under the principle of active substructure combination. 14 target compounds were obtained through aromatic nucleophilic substitution (SNAr) when fluoride nitrobenzene and morpholine-4-sulfonamide were used as starting materials. The approach represents simple operation and broad substrate scope. Additionally, the soybean seed germination was inhibited overwhelmingly when treated with compounds 4a~4d, 4k, 4m and 4n at 50 μmol/L. Furthermore, the inhibition activity of compounds 4a~4d, 4k, 4m and 4n was higher than 95% at 25 μmol/L. Finally, the activity of 4m and 4n was much higher than that of ABA and lead compound (PM4) at 15 μmol/L. Moreover, the molecular docking study revealed that 4m and 4n could bind abscisic acid receptor strongly than ABA and PM4. These results are benefit to discovering novel ABA analogues.

Key words: ABA functional analogue, morpholine sulfonamide, inhibition germination, aromatic nucleophilic substitution