title: Synthesis, antifungal activity and structure-activity relationships of vanillin oxime-N-O-alkanoates.
abstract: Vanillin oxime-N-O-alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1H, 13C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but significantly increased after conversion of the oxime to oxime-N-O-alkanoates. While vanillin oxime-N-O-dodecanoate with an EC50 value 73.1 microg/mL was most active against M. phaseolina, vanillin oxime-N-O-nonanoate with EC50 of value 66.7 microg/mL was most active against R. solani. The activity increased with increases in the acyl chain length and was maximal with an acyl chain length of nine carbons.
authors: Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi 110 012, India.
authors: Vivek
authors: V
authors: Ahluwalia
authors: Nandini
authors: N
authors: Garg
authors: Birendra
authors: B
authors: Kumar
authors: Suresh
authors: S
authors: Walia
authors: Om P
authors: OP
authors: Sati
mesh_terms: D000473:Alkanes / Q000737:chemistry; D000935:Antifungal Agents; D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002855:Chromatography, Thin Layer; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010091:Oximes / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
chemical_list: D000473:Alkanes; D000935:Antifungal Agents; D001547:Benzaldehydes; D010091:Oximes; C100058:vanillin