Enantioseparation of the fungicide imazalil in orange juice by chiral HPLC. Study on degradation rates and extractive/enrichment techniques

Abstract

Imazalil ([1-(β-allyloxy-2,4-dichlorophenethyl)imidazole]) is a systemic chiral fungicide used in postharvest protection of citruses against fungi development for during storage and transportation. The chemical structure of imazalil shows an asymmetric carbon in the C7 position. These enantiomers may have different toxicity. A method for both chiral enantiomers extraction and determination in orange juice is developed in order to provide their concentration and to study the degradation rates in orange juice. Spiked imazalil was extracted from orange juice by dispersive liquid-liquid micro extraction and solid phase extraction. Recovery assays of imazalil enantiomers from spiked orange juice samples showed that solid phase extraction is a better choice in order to obtain higher recovery values. Obtained chromatographic data show that within 24h the (-)-imazalil enantiomer decreases from 0.548 to 0.471 (expressed as enantiomer fraction).

Keywords: Degradation kinetics; Dispersive liquid–liquid microextraction; HPLC enantioseparation; Imazalil; Orange juice; Solid phase extraction.