Design, synthesis and herbicidal evaluation of novel 4-(1H-pyrazol-1-yl)pyrimidine derivatives
Design, synthesis and herbicidal evaluation of novel 4-(1H-pyrazol-1-yl)pyrimidine derivatives
复制标题
新型4-(1H-吡唑-1-基)嘧啶衍生物的设计、合成及除草评价
DOI：
10.1002/ps.3918
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发表时间：
2015-08-01
影响因子：
4.1
通讯作者：
Li, Jian-Hong
中科院分区：
文献类型：
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作者：
Ma, Hong-Ju;Zhang, Jian-Hua;Li, Jian-Hong
背景技术设计、合成了一系列新型吡唑基嘧啶衍生物，并通过IR、H-1 NMR、C-13 NMR、质谱和元素分析进行表征。对30种吡唑基嘧啶衍生物的除草活性进行了评价。结果9个化合物对狼尾草具有良好的除草活性，其中N-乙基-6-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-嘧啶-4-胺对根部的抑制活性最强。 苦豆子的生长，IC50为1.90mgL(-1)。 2-甲基-4-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-6-(丙-2-炔-1-基氧基)嘧啶对苦豆子幼苗叶绿素水平的抑制作用最强(IC50=3.14mgL(-1))。结论构效关系表明, 嘧啶环上的6位对于漂白活性起着非常重要的作用。当炔氧基被烷氧基、氨基、烷硫基和烷基磺酰基取代时，化合物的漂白活性减弱。然而，嘧啶环6位被氨基取代的化合物对杂草根生长表现出优异的抑制活性。 (c) 2014年化学工业学会
BACKGROUNDA series of novel pyrazolylpyrimidine derivatives were designed, synthesised and characterised by IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analysis. The herbicidal activities of 30 pyrazolylpyrimidine derivatives were assessed.RESULTSNine compounds caused good herbicidal activity for Pennisetum alopecuroides L. Among them, N-ethyl-6-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-pyrimidin-4-amine exhibited the strongest inhibitory activity against the root growth of P. alopecuroides, with an IC50 of 1.90mgL(-1). 2-Methyl-4-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-6-(prop-2-yn-1-yloxy)pyrimidine produced the highest inhibition of chlorophyll level in seedlings of P. alopecuroides (IC50=3.14mgL(-1)).CONCLUSIONThe structure-activity relationship indicated that the alkynyloxy group at the 6-position on the pyrimidine ring played a very important role for bleaching activities. When the alkynyloxy group was replaced by alkoxy, amino, alkylthio and alkylsulfonyl groups, the bleaching activities of the compounds were diminished. However, the compounds substituted by an amino at the 6-position of the pyrimidine ring exhibited excellent inhibition activities against weed root growth. (c) 2014 Society of Chemical Industry