Isothiazolinone derivative

Pazzaglia M, Vincenzi G, Gasparri F, Tosti A (1996) Occupational hypersensitivity to isothiazolinone derivatives in a radiology technician. Contact Dermatitis 34 143-144 Rietschel RL, Fowler JF Jr (1995) Fisher s contact dermatitis, 4th edn. Williams and Wilkins, Baltimore Rothe A, Zschunke E (1981) Uber Dermatosen durch Fotochemik-alien. Dermatol Monatsschr 167 729-742 Rustemeyer T, Frosch PJ (1995) Allergic contact dermatitis from colour developers. Contact Dermatitis 32 59-60 Scheman AJ, Katta R (1997) Photographic allergens an update. Contact Dermatitis 37 130... 

Microbicides belonging to this substance class are used on a large scale they include certain N-haloalkylthio compounds (Lucken, 1966) and isothiazolinone derivatives (Crow and Leonard, 1965 Lewis et al., 1971) [Figure 12.]. In principle there is no difference in the first step in the mechanism of action of N-haloalkylthio compounds and isothiazolone derivatives with activated N-S bonds both may react with SH groups found in cell components, with the N-S bond being split off and the formation of disulfides. 

Benzisothiazolinones and substituted isothiazolinone derivatives have been used for several years as components of preservatives. 

The validity of the model was demonstrated by reacting 35 under the same reaction conditions as expected, only one diastereoisomer 41 was formed, the structure of which was confirmed by X-ray analysis. When the vinylation was carried out on the isothiazolinone 42 followed by oxidation to 40, the dimeric compound 43 was obtained, showing that the endo-anti transition state is the preferred one. To confirm the result, the vinyl derivative 42 was oxidized and the intermediate 40 trapped in situ with N-phenylmaleimide. The reaction appeared to be completely diastereoselective and a single diastereomer endo-anti 44 was obtained. In addition, calculations modelling the reactivity of the dienes indicated that the stereochemistry of the cycloaddition may be altered by variation of the reaction solvent. 

Other compounds under consideration include ammoniacal copper-fatty acids, isothiazolinones, benzothiazoles, sulfonamides, tetrachloroisophthalonitrile, salicylanilide derivatives, and 3-iodo-2-propynyl butylcarbamate (8-J3). 

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