Abstract
The importance of isothiazole and of compounds containing the isothiazole nucleus has been growing over the last few years. Isothiazolinones are used in cosmetic and as chemical additives for occupational and industrial usage due to their bacteriostatic and fungiostatic activity. Despite their effectiveness as biocides, isothiazolinones are strong sensitizers, producing skin irritations and allergies and may pose ecotoxicological hazards. Therefore, their use is restricted by EU legislation. Considering the relevance and importance of isothiazolinone biocides, the present review describes the state-of-the-art knowledge regarding their synthesis, antibacterial components, toxicity (including structure–activity–toxicity relationships) outlines, and (photo)chemical stability. Due to the increasing prevalence and impact of isothiazolinones in consumer’s health, analytical methods for the identification and determination of this type of biocides were also discussed.
Highlights
Organic compounds containing five-membered heterocyclic rings play an important role in many industrial sectors
The most extensively used for industrial applications and reactive intermediates, for the synthesis of various organic substances including pharmaceuticals and agrochemicals, are those based on isothiazolin-3-one
In-depth information on the synthesis of the most frequently isothiazolinone biocides used in consumer scaffold, this review provides an overview of the most used isothiazolinone ring-containing products and on biological/toxicity profile is presented
Summary
Organic compounds containing five-membered heterocyclic rings play an important role in many industrial sectors. Since obtaining the first derivatives at the end of the number of reports concerning the synthesis of the isothiazolinone derivatives MI, MCI, BIT, OIT, describing synthesis emerged in patents the literature. Synthesis of the Isothiazolinone Derivatives MI, MCI, OIT, 0and DCOIT biocides from the cyclization of either thioacrylamides or 3,3 -dithiopropionamides (Scheme 1) [11,12,13,14]. A number of protocols can be found in the literature describing the synthesis of MI, MCI, and OIT biocides from the cyclization of either thioacrylamides or 3,3′-dithiopropionamides (Scheme 1). In the same paper, the authors described obtaining MCI as a side product of the conditions in order to increase the yield of this compound.
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