Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1344-1353.DOI: 10.6023/cjoc201811041 Previous Articles     Next Articles



赵宇, 关爱莹, 李婉祯, 王卫伟, 刘鑫磊, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2018-11-30 修回日期:2019-01-28 发布日期:2019-02-22
  • 通讯作者: 王明安
  • 基金资助:


Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Zhao Yu, Guan Aiying, Li Wanzhen, Wang Weiwei, Liu Xinlei, Wang Ming'an   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2018-11-30 Revised:2019-01-28 Published:2019-02-22
  • Contact: 10.6023/cjoc201811041
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21772229, 21172254).

A series of novel 3-acetyl-4-hydrazinyl-5,5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5,5-disubstitutedfuran-2,4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), 1H NMR, 13C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 μg/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 μg/mL. The 5,5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2,4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.

Key words: hydrazine derivatives, spirocyclohexyl tetronic acid, fungicidal activity, insecticidal activity