Organophosphorous derivatives containing isatin-3-hydrazones as chemotherapeutants against fungal pathogens of sugarcane

A total of 20 novel organophosphorus derivatives have been synthesized by the reactions of O,O-diethylchlorophosphate/thiophosphate with isatin-3-(substituted benzoic acid/phenoxy acetic acid hydrazones). The derivatives have been characterized on the basis of analysis and spectral (IR and ¹H and ¹³C NMR) data. Fungicidal activities of the derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescence have been evaluated. The screening results have been correlated with the structural features of the tested compounds. The greater potency has been observed with thiophosphates compared to phosphates, with substituted phenoxy acetic acid hydrazones compared to substituted benzoic acid hydrazones, and with substitutent Cl^- attached to the aromatic ring compared to other substitutents. O,O-Diethylchlorophosphate compounds containing isatin-3-(4-chlorophenoxy acetic acid hydrazone) (IIe) and the compound containing two molecules of O,O-diethylchlorophosphate attached to isatin-3-(4-hydroxy phenoxy acetic acid) hydrazone (IIh) were proven to be more active than some prevalent commercial synthetic fungicides.