4473-25-0

Usage

Appearance

White to off-white solid

Solubility

Moderately soluble in water and organic solvents

Uses

Biocidal agent
Preservative in industrial and commercial applications
Water treatment
Pulp and paper processing
Wood preservation
Fungicide and bactericide in agricultural and horticultural products
Corrosion inhibitor in metalworking fluids
Antimicrobial agent in consumer products (paints, adhesives, and textiles)

Regulatory status

Regulated in many countries due to potential toxicity and environmental impact

Safety and handling precautions

Strict safety and handling precautions required due to potential toxicity and environmental impact

Upstream product

• 147-93-3 Thiosalicylic acid 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 95-51-2 o-chloroaniline 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 119-80-2 2,2'-dithiobenzoic acid 

Relevant academic research and scientific papers

Facile synthesis and in vitro activity of n-substituted 1,2-benzisothiazol-3(2H)-ones against dengue virus NS2BNS3 protease

Several new N-substituted 1,2-benzisothiazol-3(2H)-ones (BITs) were synthesised through a facile synthetic route for testing their anti-dengue protease inhibition. Contrary to the conventional multistep synthesis, we achieved structurally diverse BITs with excellent yields using a two-step, one-pot reaction strategy. All the synthesised compounds were prescreened for drug-like properties using the online Swiss Absorption, Distribution, Metabolism and Elimination (SwissADME) model, indicating their favourable pharmaceutical properties. Thus, the synthesised BITs were tested for inhibitory activity against the recombinant dengue virus serotype-2 (DENV-2) NS2BNS3 protease. Dose–response experiments and computational docking analyses revealed that several BITs bind to the protease in the vicinity of the catalytic triad with IC50 values in the micromolar range. The DENV2 infection assay showed that two BITs, 2-(2-chlorophenyl)benzo[d]isothiazol-3(2H)-one and 2-(2,6-dichlorophenyl)benzo[d]isothiazol-3(2H)-one, could suppress DENV replication and virus infectivity. These results indicate the potential of BITs for developing new anti-dengue therapeutics.

Broad spectrum anti-infective properties of benzisothiazolones and the parallels in their anti-bacterial and anti-fungal effects

Various mono- and bis-benzisothiazolone derivatives were synthesized and screened against different strains of bacteria and fungi in order to understand the effect of multiple electrophilic sulfur atoms and substitution pattern in the immediate vicinity of reactive sulfur. Staphyllococcus aureus-ATCC 7000699, MRSA and S. aureus-ATCC 29213 (Quality Control strain) were more susceptible to this class of compounds, and the most potent derivative 1.15 had MIC50 of 0.4?μg/mL (cf. Gentamicin?=?0.78?μg/mL). CLogP value, optimally in the range of 2.5–3.5, appeared to contribute more to the activity than the steric and electronic effects of groups attached at nitrogen. By and large, their anti-fungal activities also followed a similar trend with respect to the structure and CLogP values. The best potency of IC50?=?0.1?μg/mL was shown by N-benzyl derivative (1.7) against Aspergillus fumigatus; it was also potent against Candida albicans, Cryptococcus neoformans, Sporothrix schenckii, and Candida parapsilosis with IC50 values ranging from 0.4 to 1.3?μg/mL. Preliminary studies also showed that this class of compounds have the ability to target malaria parasite with IC50 values in low micromolar range, and improvement of selectivity is possible through structure optimization.

Treatment of rheumatism and arteriosclerosis with n-halogenophenyl-benzisothiazoles

The invention relates to the new use of certain benzisothiazoles corresponding to the following general formula: STR1 wherein R1 represents chlorine, fluorine or bromine, and R2 represents hydrogen, chlorine, fluorine or bromine, in the treatment of phlogistic and/or arteriosclerotic processes.