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

  • Wei Kailun ,
  • Shi Ruijing ,
  • Jiang Lin ,
  • Miao Chengxia ,
  • Li Ying
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  • 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 date: 2020-03-01

  Revised date: 2020-04-20

  Online 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.

Abstract

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.

Cite this article

Wei Kailun , Shi Ruijing , Jiang Lin , Miao Chengxia , Li Ying . Design, Synthesis and Biological Activities Evaluation of N-(Substitutedbenzoyl)-N'-4,7-dimethoxy-[1,2,4]-triazolo[1,5-c]pyrimidine (Thio)ureas[J]. Chinese Journal of Organic Chemistry, 2020 , 40(7) : 2127 -2134 . DOI: 10.6023/cjoc202003001

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