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Degradation of 3,5‐dimethyl‐tetrahydro‐2H‐1,3,5‐thiadiazine‐2‐thione in aqueous aerobic media
Author(s) -
Subramanian Periyasamy,
Teesch Lynn,
Thorne Peter S.
Publication year - 1996
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620150415
Subject(s) - chemistry , hydrolysis , decomposition , thiourea , mass spectrometry , high performance liquid chromatography , aqueous solution , formaldehyde , reaction rate constant , chemical decomposition , gas chromatography , fast atom bombardment , degradation (telecommunications) , organic chemistry , chromatography , medicinal chemistry , kinetics , physics , quantum mechanics , telecommunications , computer science
Decomposition of 3,5‐dimethyl‐tetrahydro‐2H‐1,3,5‐thiadiazine‐2‐thione (DTTT) has been studied by UV‐visible spectroscopy (UV‐VIS), high‐performance liquid chromatography (HPLC), gas chromatography‐mass spectrometry (GC‐MS), and fast atom bombardment‐mass spectrometry (FAB‐MS). Hydrolysis rate constants for DTTT and rate constants for product formation were measured. The partially hydrolyzed and aged DTTT solutions have been separated and analyzed by GC‐MS. Formaldehyde, 1,3‐dimethyl‐2‐thiourea, N ‐methyl dithiocarbamic methyl ester, N ‐methyldithiocarbamic perthiomethyl ester, 2‐methyl‐5‐dihydro‐3H‐4‐thia‐1,2‐isooxazolidine‐3‐thione, 1,3,5‐trimethyl‐hexahydro‐2H‐1,3,5‐triazine‐2‐thione, 4‐methyl‐5‐methylimino‐1,2,4‐dithiazolidine‐3‐thi‐one, and 2,4‐dimethyl‐1,2,4‐thiadiazolidine‐3,5‐dithione were identified from the hydrolyzed DTTT solution. Methyl isothiocyanate, which is one of the intermediates formed during the decomposition of DTTT, was also monitored by UV‐VIS and HPLC for the formation of common products and characterized by GC‐MS. The decomposition pathways for DTTT are presented and are in accord with the limited literature data. Environmental impact assessment of the DTTT and its metabolites is summarized.