Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation was written by Cheng, Xiang;Wang, Wei;Wang, Yunxiao;Xia, Dongguo;Yin, Fang;Liu, Qiaoyun;Luo, Huisheng;Li, Meng;Zhang, Chengqi;Cao, Haiqun;Lv, Xianhai. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid This article mentions the following:
Plant pathogenic fungi seriously threaten agricultural production There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound (I) exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of com. fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to pos. control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound I may impede the growth and reproduction of S. sclerotiorum by affecting the morphol. of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound I did not injure the growth or reproduction of Italian bees. This study revealed that compound I is expected to be developed for efficient and safe agricultural fungicides. In the experiment, the researchers used many compounds, for example, 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid).
5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics