Dibromo-3-nitrilopropionamide DBNPA

General information. DBNPA is a halogenated amide and is considered a fast kill biocide. It has seen widespread use in water treatment and pulp and paper applications but in the oilfield is used primarily to treat the water used to prepare fracturing fluids. Its main attribute seems to be that its biocidal action is very fast, but the active then hydrolyzes to less toxic by-products. This may be advantageous in applications where water is stored prior to discharge so deactivation may not be necessary. 

Mechanism of action. The presence of two bromine atoms at C-2 of DBNPA means that this carbon atom is extremely electrophillic and will be the site of nucleophilic attack by cellular or extracellular nucleophiles. 

The most likely cellular nucleophiles to attack the carbon backbone of DBNPA are the nucleophilic sulfur containing amino acids methionine and cysteine. The reaction is irreversible and the result is inactivation of the protein that contains these amino acids. It is also possible that the amine containing amino acids (lysine, arginine) may also react with DBNPA, but the rate of that reaction is probably slower than the reaction with the sulfur nucleophiles. This is due to the fact that at the pH range that DBNPA is most commonly used (less than pH 7.5) the amine groups of the lysine and arginine residues are protonated and will react slower than free amines. 

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The concept of dispensing biocides or biostats in tablet form has recently been extended to the supply of certain nonoxidizers, such as 2,2-dibromo-3-nitrilopropionamide (DBNPA) (which has been widely available for many years as a liquid product and to a lesser extent as a powdered product). 

Dibromonitrilopropionamide. See 2,2-Dibromo-3-nitrilopropionamide 2,2-Dibromo-3-nitrilopropionamide CAS 10222-01-2 EINECS/ELINCS 233-539-7 Synonyms Acetamide, 2,2-dibromo-2-cyano- DBNPA Dibromocyanoacetamide a,a-Dibromo-a-cyanoacetamide Dibromonitrilopropionamide Classification Halogenated cyanoacetamide Empirical C3H2Br2N20... 

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