Transformation, characterization and bioassay of some compounds from Anethum graveolens L. seed oil: Structure activity relationship

Carvone and camphor were isolated from A. graveolens seed essential oil by column chromatography. Chemical transformations of carvone and camphor with semicarbazide hydrochloride, 2, 4-dinitrophenylhydrazine and hydroxylamine hydrochloride yielded the products semicarbazone, 2, 4-dinitrophenyl hydrazone and oxime.All these compounds were characterized using FT-IR, 1H NMR and13C NMR spectroscopy and screened for fungicidal activity against three phytopathogenic fungi infesting wheat i.e.Alternaria triticina, Bipolaris sorokiniana and Ustilago segetum var. tritici. Camphor showed the highest inhibitory effects against A. triticina, B. sorokiniana and Ustilago segetum var. tritici with ED90 values of 0.72, 0.68 and 0.95 mg mL-1, respectively, than other tested compounds. Imine derivatives of carvone and camphor showed less activity than carvone and camphor except carvone 2,4dinitrophenylhydrazone, which showed higher activity than carvone against B. sorokiniana and Ustilago segetum var. tritici.