Synthesis, crystal structure and fungicidal activities of 3-(Trifluoromethyl)-Pyrazole-4-carboxylic oxime ester derivatives

Fifteen new pyrazole-4-carboxylic oxime ester derivatives were synthesized from benzaldehyde oxime and 3-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride conveniently. These pyrazole-4carboxylic oxime ester structures were confirmed by( 1)H NMR and HRMS. The compound 5f was further confirmed by X-ray diffraction. They crystallized in the monoclinic system, space group C2/c, Z = 8. The fungicidal activity results indicated that some of these compounds possessed good activity against S. sclerotiorum, B. cinerea, R. solani, P. oryae and P. piricola at 50 ppm. Furthermore, the structure-activity relationship was studied by molecular docking simulation. (C) 2022 Published by Elsevier B.V.

Automated summary

Fifteen new pyrazole-4-carboxylic oxime ester derivatives were synthesized conveniently from benzaldehyde oxime and 3-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride. The structures of these pyrazole-4-carboxylic oxime esters were confirmed by various analytical techniques. Some of these compounds exhibited good fungicidal activity against several fungi at 50 ppm. Furthermore, the structure-activity relationship was investigated through molecular docking simulation.