Synthesis and biological activity of 4-Fluorobenzalaniline and its N-phenyl derivatives

4-Fluorobenzalaniline, 4-fluorobenzal-4-toluidine, 4-fluorobenzal-4-anisidine, 4-fluorobenzal-4-phenetidine, 4-fluorobenzal-4-fluoroaniline, 4-fluorobenzal-4-chloroaniline and 4-fluorobenzal-4-bromoaniline were prepared by condensing 4-fluorobenzaldehyde with aniline and substituted anilines in equimolar ratio. All the products were characterized on the basis of elemental analysis, UV, IR, PMR and mass spectra and were screened in vitro for their antifungal activity against Alternaria alternata, Fusarium oxysporum, Myrothecium roridum, Colletotrichum capsici and Ustilago tritici by spore germination inhibition method. The compounds were also tested for their nematicidal activity against Ditylenchus myceliophagus, using poison food technique and aqueous in vitro screening. 4-Fluorobenzal-4-phenetidine has shown moderate fungitoxicity against F. oxysporum and M. roridum. Three compounds namely 4-fluorobenzal-4-toluidine, 4-fluorobenzal-4-fluoroaniline and 4-fluorobenzal-4-bromoaniline have indicated almost complete control of nematode population build-up at 1000 ppm concentration against D. myceliophagus. 4-Fluorobenzal-4-anisidine has shown promising nematicidal activity against the test nematode.