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Chemistry and Industry of Forest Products ›› 2014, Vol. 34 ›› Issue (1): 62-72.doi: 10.3969/j.issn.0253-2417.2014.01.011

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Synthesis and Fungicidal Activity of Maleated Rosin-based Disulfamide Compounds

SHI Xian-chun, XU Xue-tang, DUAN Wen-gui, MIN Fang-qian, HUANG Duo-yun   

  1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
  • Received:2013-03-11 Online:2014-02-25 Published:2014-03-05

Abstract: Maleated rosin acyl chloride was prepared via acyl chlorination using maleated rosin as starting material. It was followed by the N-acylation reaction of maleated rosin acyl chloride with N-aryl sulfonyl ethylenediamines to obtain fourteen novel maleated rosin-based disulfonamide compounds (4a-4n). The target compounds were characterized by means of FT-IR, 1H NMR,13C NMR, ESI-MS, UV-Vis, and elemental analysis. Compounds 4a-4n were identified to be maleated rosin-based diphenylsulfamide, maleated rosin-based di(p-methyl)phenylsulfamide, maleated rosin-based di(m-methyl)phenylsulfamide, maleated rosin-based di(p-methoxy)phenylsulfamide, maleated rosin-based di(m-methoxy)phenylsulfamide, maleated rosin-based di(p-bromo)phenylsulfamide, maleated rosin-based di(m-bromo)phenylsulfamide, maleated rosin-based di(p-chloro)phenylsulfamide, maleated rosin-based di(m-chloro)phenylsulfamide, maleated rosin-based di(p-fluoro)phenylsulfamide, maleated rosin-based di(o-fluoro)phenylsulfamide, maleated rosin-based di(p-nitro)phenylsulfamide, maleated rosin-based di(m-nitro)phenylsulfamide, maleated rosin-based di(o-nitro)phenylsulfamide, respectively. The preliminary bioassay showed that compounds 4a-4n exhibited a certain fungicidal activity against five tested fungi. Among them compound 4k, maleated rosin-based di(o-fluoro)phenylsulfamide, had inhibition rate of 66.8 % against Physalospora piricola at the concentration of 50 mg/L.

Key words: maleated rosin, disulfamide, synthesis, fungicidal activity

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