Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2127-2134.DOI: 10.6023/cjoc202003001 Previous Articles     Next Articles


魏凯伦a, 石瑞静a, 姜林a,b, 苗成霞a,b, 李映a,b   

  1. a 山东农业大学化学与材料科学学院 山东泰安 271018;
    b 山东省食品安全分析与检测工程技术研究中心 山东泰安 271018
  • 收稿日期:2020-03-01 修回日期:2020-04-20 发布日期:2020-05-08
  • 通讯作者: 李映
  • 基金资助:

Design, Synthesis and Biological Activities Evaluation of N-(Substitutedbenzoyl)-N'-4,7-dimethoxy-[1,2,4]-triazolo[1,5-c]pyrimidine (Thio)ureas

Wei Kailuna, Shi Ruijinga, Jiang Lina,b, Miao Chengxiaa,b, Li Yinga,b   

  1. a College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018;
    b Food Safety Analysis and Test Engineering Technology Research Center of Shandong Province, Tai'an, Shandong 271018
  • Received:2020-03-01 Revised:2020-04-20 Published:2020-05-08
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21702127) and the Incubation Program of Youth Innovation in Shandong Province.

A series of novel N-(substitutedbenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidine (thio)ureas (11a~11q) were synthesized from α-methoxyl methyl acetate, ethyl formate and substituted benzoic acids by cyclization, Dimroth rearrangement and nucleophilic addition reactions. The structures of products were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassay showed that most of the compounds displayed positive fungicidal activity at 50 mg·L-1. Among them, N-(2-chlorobenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidinethiourea (11m) exhibited an inhibition rate of 67.25% against B. cinerea. All compounds showed certain insect growth regulation activities against 2~3 instar culex larvae, in which seven compounds exhibited revised uneclosion rate higher than 70%. N-(4-methylbenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidinethiourea (11l) showed excellent insecticidal activity, which was equivalent to the control 5% (mass fraction) pyriproxyfen. The preliminary structure-activity relationship analysis showed that compounds with electron-withdrawing group on the phenyl ring showed higher fungicidal activities, while compounds with electron-donating group exhibited higher insect growth regulation activities. Benzoylureas displayed higher fungicidal activities and benzoylthioureas exhibited good insect growth regulation activities.

Key words: chitin, benzoyl (thio) urea, triazolopyrimidine, fungicidal activity, insect growth regulation activity