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Antifungal mechanism of dichloro-N-octylisothiazolone
1998 - IRG/WP 98-30183
4,5-dichloro-N-octylisothiazolin-3-one (DCOI) is a member of the isothiazolone class of preservatives, whose antimicrobial mechanism of action has been intensively studied over the last decade. DCOI has also been intensively studied for use in wood preservation. The isothiazolones are electrophilic molecules that rapidly react with thiol groups to form covalently bonded isothiazolone-thiol adducts. This ability to bond with thiol groups is crucial to their ability to act as preservatives. Thiol groups are present in proteins as part of the amino acid cysteine, where they play an important role in maintaining protein structure and function. A number of enzymes have thiol groups at the site where the enzyme function is performed, and these thiol groups may participate in the enzyme reaction. If the isothiazolone reacts with this thiol group, the activity of the enzyme is inhibited. Our studies have shown that there are several enzymes in the Krebs cycle that are inhibited by isothiazolones and these enzymes are required to generate energy and perform many biosynthetic functions. Reflective of this, DCOI has been shown to be a rapid inhibitor of cellular respiration, causing the cell to cease consuming oxygen almost immediately upon contact with DCOI. The multiplicity of targets and their central importance to the metabolism of the cell, as well as the fact that all microbes use at least parts of the Krebs cycle, can be related to the low use levels and broad spectrum of activity of DCOI. The antimicrobial mechanism of DCOI results in a potent rapid-acting preservative with a broad spectrum of antifungal and antibacterial activity that is effective at low levels.
J S Chapman, M A Diehl, K B Fearnside, L E Leightley