Wu Jian, Wang Jian, Hu Deyu, He Ming, Jin Linhong, Song Baoan
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China.
Chem Cent J. 2012 May 30;6(1):51. doi: 10.1186/1752-153X-6-51.
The plant pathogenic fungus (such as Gibberella zeae, Fusarium oxysporum and Cytospora mandshurica) causes devastating disease in agriculture. The pathogenic fungus is responsible for billions of dollars in economic losses worldwide each year. In order to discover new fungicidal molecule with good fungicidal activity against G. zeae, F. oxysporum, and C. mandshurica, we sought to combine the active sub-structure of hydrazone and pyrazole amide derivatives together to design and synthesize novel pyrazole amide derivatives containing a hydrazone moiety.
A series of novel pyrazole amide derivatives bearing hydrazone moiety were synthesized. Their structures were characterized by 1 H-NMR, 13 C-NMR, IR, and elemental analysis. The preliminary biological assays revealed that most of the synthesized compounds exhibit favorable antifungal activities against G. zeae. The activity of compounds 7a, 7f, 7g, 7h, 7i, 7j, 7l and 7q were 40.82%, 47.78%, 50.32%, 40.82%, 49.05%, 48.73%, 40.19% and 45.89%, respectively, and the synthesized compounds showed certain antifungal activities against F. oxysporum and C.mandshurica.
A practical synthetic route to pyrazole amide derivatives containing a hydrazone moiety were synthesized by the condensation of intermediates 5-chloro-N-(4-subsititued-2-(hydrazinecarbonyl)-6-methylphenyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide with different aldehydes or ketones in ethanol at room temperature is presented, the results of the study suggested that the pyrazole amide derivatives containing hydrazone moieties could inhibit the growth of G. zeae, F. oxysporium and C. mandshurica to a certain extent.
植物病原真菌（如玉米赤霉、尖孢镰刀菌和落叶松壳囊孢）在农业中引发毁灭性病害。这种病原真菌每年在全球造成数十亿美元的经济损失。为了发现对玉米赤霉、尖孢镰刀菌和落叶松壳囊孢具有良好杀菌活性的新型杀真菌分子，我们试图将腙和吡唑酰胺衍生物的活性亚结构结合在一起，设计并合成含腙部分的新型吡唑酰胺衍生物。
合成了一系列含腙部分的新型吡唑酰胺衍生物。通过¹H-NMR、¹³C-NMR、IR和元素分析对其结构进行了表征。初步生物学试验表明，大多数合成化合物对玉米赤霉表现出良好的抗真菌活性。化合物7a、7f、7g、7h、7i、7j、7l和7q的活性分别为40.82%、47.78%、50.32%、40.82%、49.05%、48.73%、40.19%和45.89%，且合成化合物对尖孢镰刀菌和落叶松壳囊孢也表现出一定的抗真菌活性。
提出了一种通过中间体5-氯-N-(4-取代-2-(肼基羰基)-6-甲基苯基)-1,3-二甲基-1H-吡唑-4-甲酰胺与不同醛或酮在乙醇中于室温下缩合来合成含腙部分的吡唑酰胺衍生物的实用合成路线，研究结果表明含腙部分的吡唑酰胺衍生物能在一定程度上抑制玉米赤霉、尖孢镰刀菌和落叶松壳囊孢的生长。
