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

doi:10.6023/cjoc202003001

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

N-取代苯甲酰基-N'-4,7-二甲氧基-[1,2,4]三唑并[1,5-c]嘧啶(硫)脲的设计、合成及生物活性研究

魏凯伦^a, 石瑞静^a, 姜林^a,b, 苗成霞^a,b, 李映^a,b

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 E-mail:ly8049@sdau.edu.cn
基金资助:
国家自然科学基金（No.21702127）及山东省高等学校青创人才引育计划资助项目.

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^a, Shi Ruijing^a, Jiang Lin^a,b, Miao Chengxia^a,b, Li Ying^a,b

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.

1. 202127S.pdf(3876KB)

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.

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

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.

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N-取代苯甲酰基-N'-4,7-二甲氧基-[1,2,4]三唑并[1,5-c]嘧啶(硫)脲的设计、合成及生物活性研究

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

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