In order to study and develop the indole quinazoline alkaloid of the traditional Chinese medicine evodia, the thiorutaecarpine and five N-substituted derivatives were synthesized from rutaecarpine by thionation. The structures of the products were confirmed by HPLC-HRMS, IR, 1HNMR and 13CNMR. The antifungal activity on nine plant pathogens of the compounds (Ⅱ and Ⅳa~e, 10μg/mL) was analyzed, and it was found that there was almost no inhibitory effect on the plant pathogenic fungi, and N-substituted thiorutaecarpine (Ⅳa, Ⅳb and Ⅳd) had obvious antifungal activity against bacteria [Xanthomonas oryzae pv.oryzae (Ishiyama)]. The inhibitory rates of N-benzyl sulfo-rutaecarpine (Ⅳb) and N-(4-methyl benzyl) sulfo-rutaecarpine (Ⅳd) were 81.84% and 59.95%, respectively. The rutaecarpine derivatives were found to be almost non-toxic (IC50 > 80 μmol/L) to human normal cells (HFL1) by cytotoxicity assay.