林产化学与工业2020，Vol.40Issue(3)：76-84,9.DOI:10.3969/j.issn.0253-2417.2020.03.010
柠檬醛基缩氨基硫脲化合物的合成及除草活性
Synthesis and Herbicidal Activity of Citral-based Thiosemicarbazone Compounds
摘要
Abstract
Twenty-six novel citral-based thiosemicarbazone compounds 2a-2m (thirteen pairs of (2Z, 1E)/(2E, 1E)-isomers) were designed and synthesized in an attempt to develop potent herbicidal agents. The structures of the target compounds were characterized by FT-IR, NMR, and ESI-MS. The herbicidal activities of the target compounds were preliminarily evaluated in vitro against Brassica campestris and Echinochloa crusgalli. The bioassay results indicated that compounds (2Z, 1E)-2a (R=Me), (2E, 1E)-2a (R=Me), (2Z, 1E)-2b (R=Et), (2E, 1E)-2b (R=Et), and (2E, 1E)-2c (R=i-Pr) displayed inhibition rates of 82. 6％, 88. 7％, 80. 2％, 80. 5％ and 82. 0％, respectively, against the root-growth of rape (Brassica campestris) at the concentration of 100 mg/L. They were much better herbicidal activity than the commercial herbicide flumioxazin. It was found that the herbicidal activity of the compounds with aliphatic groups (R) was much better than that of the compounds with aromatic groups (R), and the (2E, 1E)-isomers bearing aliphatic groups (R) exhibited better inhibition activity than corresponding (2Z, 1E)-isomers, whereas the (2Z, 1E)-isomers bearing aromatic groups (R) showed better inhibition activity than their (2E, 1E)-isomers. The electrostatic potential and the frontier molecular orbitals of the best activity compound (2E, 1E)-2a were calculated and analyzed. This implied that the thiourea moiety was critical for the bioactive performance and the small R group was favorable for bioactivity.关键词
柠檬醛/缩氨基硫脲/立体异构体/除草活性Key words
Key word:citral/thiosemicarbazone/stereoisomer/herbicidal activity分类
化学化工引用本文复制引用
何云,段文贵,林桂汕,岑波,卜俊文,雷福厚..柠檬醛基缩氨基硫脲化合物的合成及除草活性[J].林产化学与工业,2020,40(3):76-84,9.基金项目
国家自然科学基金资助项目(31870556) （31870556）
广西林产化学与工程重点实验室开放基金资助项目(GXFC17-18-01) （GXFC17-18-01）
