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Photodegradation of the Isoxazolidine Fungicide SYP-Z048 in Aqueous Solution: Kinetics and Photoproducts

Author:
Liu, Pengfei, Xu, Yanjun, Li, Jianqiang, Liu, Junli, Cao, Yongsong, Liu, Xili
Source:
Journal of agricultural and food chemistry 2012 v.60 no.47 pp. 11657-11663
ISSN:
1520-5118
Subject:
Ascomycota, Basidiomycota, Deuteromycotina, benzene, dechlorination, fruits, fungicides, high performance liquid chromatography, irradiation, mass spectrometry, mercury, nitrogen, nuclear magnetic resonance spectroscopy, photolysis, solid phase extraction, vegetables
Abstract:
Previous research has demonstrated that 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine (SYP-Z048), a newly developed nitrogen heterocycle substituted isoxazolidine compound, has good protective and curative activities against a wide range of fungal diseases of fruits and vegetables caused by Ascomycetes, Basidiomycetes, and Deuteromycetes. In this study, the photochemical behavior of SYP-Z048 was investigated in aqueous solution and in response to solar and low-pressure mercury ultraviolet (UV) lamp irradiation. SYP-Z048 photolysis was pH- and temperature-dependent and was described by a first-order degradation reaction. A total of 11 photoproducts were separated by high-performance liquid chromatography (HPLC) and solid-phase extraction (SPE) and were identified on the basis of ¹H and ¹³C nuclear magnetic resonance (NMR) and high-performance liquid chromatography–mass spectrometry (HPLC–MS) spectra. The photoproduct structures and kinetics suggested that the phototransformation of SYP-Z048 occurred via multiple reaction pathways that included the cleavage of the N–O bond in the isoxazolidine ring and the dechlorination of the benzene ring.
Agid:
315732