Premium
Synthesis and Biological Activity of Novel Furan/Thiophene and Piperazine‐Containing (Bis)1,2,4‐triazole Mannich Bases
Author(s) -
Wang Baolei,
Shi Yanxia,
Zhan Yizhou,
Zhang Liyuan,
Zhang Yan,
Wang Lizhong,
Zhang Xiao,
Li Yonghong,
Li Zhengming,
Li Baoju
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500436
Subject(s) - chemistry , piperazine , furan , thiophene , triazole , proton nmr , bioassay , carbon 13 nmr , mannich base , 1,2,4 triazole , organic chemistry , trifluoromethyl , combinatorial chemistry , stereochemistry , alkyl , genetics , biology
Series of novel furan/thiophene and piperazine‐containing 1,2,4‐triazole Mannich bases and bis(1,2,4‐triazole) Mannich bases have been conveniently synthesized via Mannich reaction with triazole Schiff bases, various piperazine derivatives, and formaldehyde as intermediates in good yields. Their structures were characterized by melting points, 1 H NMR, 13 C NMR, IR and elemental analysis. The preliminary bioassay showed that most compounds exhibited significant in vitro and in vivo fungicidal activity against several test plant fungi. Among 32 new compounds, the trifluoromethyl‐containing compounds showed superior activity than the methyl‐containing ones. Several compounds, such as F8 , F9 , F10 , G5 , H7 , H8 , I3 and I4 , were comparable with some commercial fungicides against different fungi during the present study and could be further structurally optimized. Meanwhile, several compounds showed good herbicidal activity against Brassica campestris at 100 µg/mL and KARI inhibitory activity at 200 µg/mL. However, compounds exhibited poor insecticidal activity against oriental armyworm at 200 µg/mL in the preliminary studies. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic structures.