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Chemistry and Industry of Forest Products ›› 2022, Vol. 42 ›› Issue (1): 43-50.doi: 10.3969/j.issn.0253-2417.2022.01.006

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Synthesis and Herbicidal Activity Investigation of p-Menth-3-en-1-sulfonamide Compounds

Hongmei ZHANG1,2,3, Yuxiang CHEN1,3, Shichao XU1,3, Jing WANG1,2,3, Jianxin JIANG2, Zhendong ZHAO1,3,*()   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
    2. College of Materials Science and Technology, Bejing Forestry University, Beijing 100083, China
    3. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
  • Received:2020-12-04 Online:2022-02-28 Published:2022-03-11
  • Contact: Zhendong ZHAO E-mail:zdzhao@189.cn

Abstract:

Ten p-menth-3-en-1-sulfamide compounds (2a-2j) were synthesized by using turpentine as start material, sulfonyl chlorideas sulfonylation reagent, triethylamine as acid binding agent.Their structures were characterized by FT-IR, 1H NMR, 13C NMR and LC-MS.The post-emergence herbicidal activities of them against Echinochloa crusgalli were evaluated.The results showed that the yields of p-menth-3-en-1-sulfamide compounds were 60%-87%.The structural characterization spectra were consistent with the compounds, indicating that the target compounds had been successfully synthesized.Some compounds showed obvious inhibition activities to the growth of E.crusgalli.Among them, p-menth-3-en-1-propyl-sulfamide (2f) showed the best herbicidal activity against E.crusgalli.And the IC50 values of it against the stem and root growth of E.crusgalli were 0.36 and 0.17 mmol/L, respectively.Cytotoxicity assays results showed that p-menth-3-en-1-sulfamide compounds had no significant inhibition against cell proliferation of normal human HUVEC-C cells and mouse fibroblasts BALB/C 3T3 cells in vitro.Structure-activity relationship analysis showed that the herbicidal activity of alkyl sulfonamide derivatives was significantly higher than that of aryl groups and reached the best when the alkyl group containing three carbon atoms.However, the herbicidal activity was weakened when the alkyl group was connected with electron-absorbing groups.The herbicidal activities of benzene or naphthalene rings with electron-donating groups (methyl, methoxyl) were better than those of electron-absorbing groups (F, Cl, Br).

Key words: turpentine, p-menth-3-en-1-amine, botanical herbicides, sulfamide compounds, herbicidal activity

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