Design, Synthesis and Fungicidal Activities of Some Novel Pyrazole Derivatives

Molecules

Xue-Ru Liu¹  Hua Wu¹  Ze-Yu He²  Zhi-Qing Ma²  Jun-Tao Feng¹ 

[1] Research & Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A&F University, Xinong Road 22, Yangling 712100, Shaanxi, China;

关键词: pyrazole derivatives;    chemical modification;    antifungal activity;    structure–activity relationships;   

DOI  :  10.3390/molecules190914036

来源: mdpi

【 摘 要 】

In order to discover new compounds with good fungicidal activities, 32 pyrazole derivatives were designed and synthesized. The structures of the target compounds were confirmed by ¹H-NMR, ¹³C-NMR, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and their fungicidal activities against Botrytis cinerea, Rhizoctonia solani Kuhn, Valsa mali Miyabe et Yamada, Thanatephorus cucumeris (Frank) Donk, Fusarium oxysporum (S-chl) f.sp. cucumerinum Owen, and Fusarium graminearum Schw were tested. The bioassay results indicated that most of the derivatives exhibited considerable antifungal activities, especially compound 26 containing a p-trifluoromethyl- phenyl moiety showed the highest activity, with EC₅₀ values of 2.432, 2.182, 1.787, 1.638, 6.986, and 6.043 μg/mL against B. cinerea, R. solani, V. mali, T. cucumeris, F. oxysporum, and F. graminearum, respectively. Moreover, the activities of compounds such as compounds 27–32 were enhanced by introducing isothiocyanate and carboxamide moieties to the 5-position of the pyrazole ring.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.