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Benzisothiazolinone

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Benzisothiazolinone
Names
Preferred IUPAC name
1,2-Benzothiazol-3(2H)-one
Other names
Benzisothiazolinone, Benzisothiazolin-3-one, Benzisothiazolone
Identifiers
3D model (JSmol)
Abbreviations BIT
119510
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.292 Edit this at Wikidata
EC Number
  • 220-120-9
MeSH 1,2-benzisothiazoline-3-one
RTECS number
  • DE4620000
UNII
  • InChI=1S/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9) checkY
    Key: DMSMPAJRVJJAGA-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NOS/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)
    Key: DMSMPAJRVJJAGA-UHFFFAOYAC
  • O=C1c2ccccc2SN1
Properties
C7H5NOS
Molar mass 151.18 g·mol−1
Appearance white powder
Melting point 158 °C (316 °F; 431 K)[1]
1 g/L
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H315, H317, H318, H400
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P333+P313, P362, P363, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Benzisothiazolinone (BIT) is an organic compound with the formula C6H4SN(H)CO. A white solid, it is structurally related to isothiazole, and is part of a class of molecules called isothiazolinones.[2] BIT is widely used as a preservative and antimicrobial.[3]

Usage

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Benzisothiazolinone has a microbicide and a fungicide mode of action. It is widely used as a preservative, for example in:

  • emulsion paints, caulks, varnishes, adhesives, inks, and photographic processing solutions
  • home cleaning and car care products; laundry detergents, stain removers and fabric softeners;
  • industrial settings, for example in textile spin-finish solutions, leather processing solutions, preservation of fresh animal hides and skins
  • agriculture in pesticide formulations
  • gas and oil drilling in muds and packer fluids preservation.[4]: iv 

In paints, it is commonly used alone or as a mixture with methylisothiazolinone. Typical concentrations in products are 200–400 ppm depending on the application area and the combination with other biocides. According to a study in Switzerland, 19% of the paints, varnishes and coatings contained BIT in 2000. The fraction in adhesives, sealants, plasters and fillers was shown at that time as 25%.[5] A later study in 2014 shows a dramatic rise in usage, to 95.8% of house paints.[6]

Home cleaning and other care products that are high in water are easily contaminated by microorganisms, so isothiazolinones are often used as a preservative in these products because they are good at combatting a broad array of bacteria, fungi, and yeasts.[2]

A Swiss investigation found that BIT is used in concentrations between 50 and 500 ppm in tattooing ink.[7] According to regulations in the EU and Switzerland, BIT cannot be used in cosmetics. However, it is allowed in the United States and Canada.[2]

Health hazards

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Given sufficient dose and duration, dermal exposure can produce skin sensitization and allergic contact dermatitis,[8] and is classified as an irritant for skin and eyes.[1] BIT's low molar mass allows for it to penetrate the epidermis and then react with the skin macromolecules, which causes the irritation.[2] Benzisothiazolinone has also been linked with Systemic Contact Dermatitis via airborne contact.[9]

In 2012, the Scientific Committee on Consumer Safety in Europe found BIT's "sensitising potential is of concern...Sensitisation from related isothiazolinones is an important problem in consumers. This has occurred because there has been consumer exposure before safe levels of exposure relevant to sensitisation have been established. Benzisothiazolinone is a skin sensitiser in animal models with potency similar to methylisothiazolinone. Methylisothiazolinone, at 100 ppm (0.01%) in cosmetic products is causing contact allergy and allergic contact dermatitis in the consumer. Benzisothiazolinone is known to be a sensitiser in man and has induced sensitisation at circa 20 ppm in gloves."[10]

The opinion further states: "There is no information on what may be safe levels of exposure to benzisothiazolinone in cosmetic products from the point of view of sensitisation. Until safe levels of exposure have been established, the use of benzisothiazolinone in cosmetic products as a preservative or for other functions cannot be considered safe in relation to sensitisation."

Later, in 2013, researchers published a study that set out to derive the highest concentration of BIT in certain consumer products that would result in exposures below the No Expected Sensitization Induction Level (NESIL); that is, where normal use would yield a dose below the level at which skin sensitization might occur. The products under consideration were sunscreen, laundry detergent, dish soap, and spray cleaner; by way of calculation they derived BIT NESILs of 0.0075%, 0.035%, 0.035%, and 0.021%, respectively. They then performed a pilot examination via bulk sample analysis of one representative product from each category labelled as containing BIT. Their findings showed all BIT concentrations well below the derived NESIL, with 0.0009% and 0.0027% for sunscreen and dish soap, respectively, and no detection in the laundry detergent and spray cleaner products, meaning the concentration was at or below the limit of detection of 0.0006%.[11]

References

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  1. ^ a b Record of 1,2-Benzisothiazol-3(2H)-one in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 22 October 2007.
  2. ^ a b c d Garcia-Hidalgo, Elena; Schneider, Dovilé; von Goetz, Natalie; Delmaar, Christiaan; Siegrist, Michael; Hungerbühler, Konrad (2018). "Aggregate consumer exposure to isothiazolinones via household care and personal care products: Probabilistic modelling and benzisothiazolinone risk assessment". Environment International. 118: 245–256. Bibcode:2018EnInt.118..245G. doi:10.1016/j.envint.2018.05.047. PMID 29894934. S2CID 48364636.
  3. ^ Silva, Vânia; Silva, Cátia; Soares, Pedro; Garrido, E. Manuela; Borges, Fernanda; Garrido, Jorge (2020). "Isothiazolinone Biocides: Chemistry, Biological, and Toxicity Profiles". Molecules. 25 (4): 991. doi:10.3390/molecules25040991. PMC 7070760. PMID 32102175.
  4. ^ U.S. Environmental Protection Agency. September 29, 2005 EPA Reregistration Decision
  5. ^ Reinhard; et al. (2001). "Preservation of products with MCI/MI in Switzerland". Contact Dermatitis. 45 (5): 257–64. doi:10.1034/j.1600-0536.2001.450501.x. PMID 11722483. S2CID 21296570.
  6. ^ Schwensen, J.F.; Lundov, M. D.; Bossi, R.; Banerjee, P.; Giménez-Arnau, E.; Lepoittevin, J. P.; Lidén, C.; Uter, W.; Yazar, K.; White, I. R.; Johansen, J.D. (2015). "Methylisothiazolinone and benzisothiazolinone are widely used in paint: a multicentre study of paints from five European countries". Contact Dermatitis. 72 (3): 127–38. doi:10.1111/cod.12322. PMID 25510184. S2CID 9651179.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Garcia-Hidalgo, Elena; Sottas, Virginie; von Goetz, Natalie; Hauri, Urs; Bogdal, Christian; Hungerbühler, Konrad (2017). "Occurrence and concentrations of isothiazolinones in detergents and cosmetics in Switzerland". Contact Dermatitis. 76 (2): 96–106. doi:10.1111/cod.12700. PMID 27862003. S2CID 3918533.
  8. ^ ToxNet 1,2-Benzisothiazoline-3-one
  9. ^ Diljit Kaur-Knudsen, Torkil Menné, Berit Christina Carlsen (2012). "Systemic Allergic Dermatitis Following Airborne Exposure to 1,2-Benzisothiazolin-3-one". Contact Dermatitis. 67 (5): 310–312. doi:10.1111/j.1600-0536.2012.02117.x. PMID 23039006. S2CID 35041455.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ Scientific Committee on Consumer Safety (SCCS) Opinion on Benzisothiazolinone
  11. ^ Novick, R.M.; Nelson, M.L.; Unice, K. M.; Keenan, J. J.; Paustenbach; D. J. (2013). "Estimation of the Safe Use Concentrations of the Preservative 1,2-Benzisothiazolin-3-one (BIT) in Consumer Cleaning Products and Sunscreens". Food Chem. Toxicol. 56: 60–6. doi:10.1016/j.fct.2013.02.006. PMID 23429043.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Literature

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  • Wilfried Paulus: Directory of Microbicides for the Protection of Materials and Processes. Springer Netherland, Berlin 2006, ISBN 1-4020-4861-0.
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