One-pot synthesis and insecticidal activity of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles

PLEM, S.C.; MACHUCA, L.M.; GUTIÉRREZ, C.G.; COLL-ARÁOZ, M.V.; VAN NIEUWENHOVE, G.A.; VIRLA, E.G. AND MURGUÍA, M.C.; MURGUÍA, M.C.

RESEARCH JOURNAL OF CHEMISTRY AND ENVIRONMENT

WRI World Researches Associations

Lugar: Indore; Año: 2020 vol. 24 p. 102 - 108

0972-0626

Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles was performed by direct condensation of (ethoxymethylene)malononitrile and aryl hydrazines. The resulting N,N-containing heterocycles possess insecticidal properties relative to microlepidoptera species, plant phatogens. The insecticidal activity of four novel synthetic N-aryl pyrazoles to Tuta absoluta larvae was assessed. Fipronil, a well-known aryl pyrazole insecticide, was also tested as the positive control. A generalized linear model reported significant differences in efficacy and tomato leaf consumption among the different treatments. Fipronil treatment was the most effective one (100% mortality after 48 h), followed by 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile treatment (3c) (75% mortality after 48 h) and 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)-phenyl-1H-pyrazole-4-carbonitrile treatment (3b) (60% mortality after 48 h). These compounds, with simpler structures than Fipronil, could be used as novel insecticides.