Citation: 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 shu

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

Corresponding author: Li Ying, ly8049@sdau.edu.cn
Received Date: 1 March 2020
Revised Date: 20 April 2020
Available Online: 7 May 2020
Fund Project: the National Natural Science Foundation of China 21702127Project supported by the National Natural Science Foundation of China (No. 21702127) and the Incubation Program of Youth Innovation in Shandong Province

Figures(4)

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.
- chitin,
- benzoyl (thio) urea,
- triazolopyrimidine,
- fungicidal activity,
- insect growth regulation activity
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