The reaction of ethylenethiourea with nitrite and transnitrosation by N-nitrosoethylenethiourea.
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Ethylenethiourea (ETU), a degradation and metabolic product of ethylenebisdithiocarbamate fungicides, was nitrosated by NaNO<SUB>2</SUB> to form N-nitrosoethylenethiourea (NETU). ETU was nitrosated much more rapidly than morpholine and methylurea, which are easily nitrosatable compounds, and NETU formation increased with lowering of the pH. NETU was most unstable around pH 10 and was rather stable in strongly alkaline media above pH 12. The main decomposition reaction of NETU in acidic media was denitrosation. Transnitrosation by NETU to secondary amines gave high yields of nitrosamines at pH 3 and even at pH 5.
- Chemical and Pharmaceutical Bulletin
Chemical and Pharmaceutical Bulletin 31(10), 3678-3683, 1983
The Pharmaceutical Society of Japan