Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives.
A series of 1,2,3-triazole phenylhydrazone derivatives were designed and synthesized as antifungal agents. Their structures were determined based on (1)H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifungal activities were evaluated against four phytopathogenic fungi including Rhizoctonia solani, Sclerotinia sclerotiorum, Fusarium graminearum and Phytophthora capsici, by the mycelium growth inhibition method in vitro. Compound 5p exhibited significant anti-phytopathogenic activity, with the EC50 values of 0.18, 2.28, 1.01, and 1.85 μg mL(-1), respectively. In vivo testing demonstrated that 5p was effective in the control of rice sheath blight, rape sclerotinia rot and fusarium head blight. A 3D-QSAR model was built for a systematic SAR profile to explore more potent 1,2,3-triazole phenylhydrazone analogs as novel fungicides.
College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing Agricultural University, Nanjing 210095, P. R. China. yeyh@njau.edu.cn.
Zhi-Cheng
ZC
Dai
Yong-Fei
YF
Chen
Mao
M
Zhang
Sheng-Kun
SK
Li
Ting-Ting
TT
Yang
Li
L
Shen
Jian-Xin
JX
Wang
Shao-Song
SS
Qian
Hai-Liang
HL
Zhu
Yong-Hao
YH
Ye
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D066244:Proton Magnetic Resonance Spectroscopy; D021281:Quantitative Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*
D000935:Antifungal Agents; D006835:Hydrazones; D014230:Triazoles; C012483:phenylhydrazone