Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3717-3725.DOI: 10.6023/cjoc202105009 Previous Articles     Next Articles



王卫伟, 李益豪, 刘鑫磊, 赵宇, 王明安*()   

  1. 中国农业大学应用化学系 农药创新研究中心 北京 100193
  • 收稿日期:2021-05-07 修回日期:2021-05-31 发布日期:2021-06-22
  • 通讯作者: 王明安
  • 基金资助:

Synthesis and Fungicidal Activity of Novel 3,7-Dimethylocta-2,6-dienamides and 3,7-Dimethyl-6,7-dihydroxyoct-2-enamides

Weiwei Wang, Yihao Li, Xinlei Liu, Yu Zhao, Mingan Wang()   

  1. Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2021-05-07 Revised:2021-05-31 Published:2021-06-22
  • Contact: Mingan Wang
  • Supported by:
    National Natural Science Foundation of China(21772229)

A series of novel (Z)- and (E)-3,7-dimethylocta-2,6-dienamides and optical (6R or 6S)-3,7-dimethyl-6,7-dihydroxyoct-2-enamides were designed and synthesized using (Z)- and (E)-geraniols as raw materials, respectively. Their structures were characterized by IR, 1H NMR, 13C NMR and HR-ESI-MS spectra. The preliminary bioassay results indicated that some compounds exhibit certain in vitro fungicidal activities against Rhizoctonia solani and Sclerotinia sclerotiorum at the concentration of 50 µg/mL. For example, (Z)-N-(2-(4-chlorophenyl)phenyl)-3,7-dimethylocta-2,6-dienamide (5d), (6S,2Z)-N-(2- (4-chlorophenyl)phenyl)-3,7-dimethyl-6,7-dihydroxyoct-2-enamide (7g) and (6S,2Z)-N-(2-(4-chlorophenyl)phenyl)-3,7-dimethyl-6,7-dihydroxyoct-2-enamide (7h) have EC50 values of 46.3, 38.1 and 40.6 µg/mL against S. sclerotiorum, and (Z)-N-(4-tert-butyl-benzyl)-3,7-dimethylocta-2,6-dienamide (5b) has an EC50 value of 20.5 µg/mL against R. solani, respectively. The in vivo efficacy of (Z)-N-(2-chloro-4-trifluromethylphenyl)-3,7-dimethylocta-2,6-dienamide (5c), (E)-N-(2-chloro- 4-trifluromethylphenyl)-3,7-dimethylocta-2,6-dienamide (5g) and (6S,2E)-N-(2-chloro-4-trifluromethylphenyl)-3,7-dimethyl- 6,7-dihydroxyoct-2-enamide (7m) at the concentration of 400 µg/mL were in the range of 50%~100% against Pseudoperonospora cubensis and Erysiphe graminis. They have a potential to be optimized for improving the fungicidal activity.

Key words: 3,7-dimethylocta-2,6-dienamide, 3,7-dimethyl-6,7-dihydroxyoct-2-enamide, Sharpless asymmetric dihydroxylation, fungicidal activity