Abstract
The gas phase pyrolysis of trichlorfon was investigated by the on-line gas chromatography – mass spectrometry (GC-MS) pyrolysis and theoretical calculations. Two reaction channels were proposed in the pyrolytic reaction, by analyzing the detected pyrolytic products in the total ion chromatography, including 2,2,2-trichloroacetaldehyde, dimethyl phosphite, and dichlorvos. Theoretical calculations showed that there is an intramolecular hydrogen bond between the hydroxyl group and the phosphate O atom in trichlorfon, through which the hydroxyl H atom can be easily transferred to phosphate O atom to trigger two pyrolytic channels. In path-a, migration of H atom results in direct decomposition of trichlorfon to give 2,2,2-trichloroacetaldehyde and dimethyl phosphite in one step. In path-b, migration of H atom in trichlorfon is combined with formation of the O-P bond to give an intermediate, followed by HCl elimination to afford dichlorvos. Path-a is kinetically more favorable than path-b, which is consistent with the GC-MS results.
Highlights
Trichlorfon (TCF, Fig. 1) is an organophosphorus pesticide (OP) that is widely used to control agricultural pests because of its high insecticidal activity, acute toxicity, and relatively low environmental persistence [1,2,3,4,5]
Total ion current chromatograms (TIC), obtained using the gas chromatography – mass spectrometry (GC-mass spectrometry (MS)) system, for DCV and TCF standards are shown in Fig. 2-a and Fig. 2-b, respectively
The gas phase pyrolysis of TCF was investigated in on-line gas chromatography (GC)-MS pyrolysis experiments and using theoretical calculations
Summary
Trichlorfon (TCF, Fig. 1) is an organophosphorus pesticide (OP) that is widely used to control agricultural pests because of its high insecticidal activity, acute toxicity, and relatively low environmental persistence [1,2,3,4,5]. It is difficult to remove OP from organic material using water, as it is for many other types of pesticide, and OP residues are often found on vegetable and fruit skins and even in groundwater. Methods have been developed to quantify TCF residues in fruits and vegetables [6] to allow food safety to be ensured
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