2-Octyl-2H-isothiazol-3-on

2-n-Octyl-4-isothiazolin-3-one

HCID 33528CAS 26530-20-1

Grundinformationen

Standard-SMILES
CCCCCCCCn1sccc1=O
InChIKey
JPMIIZHYYWMHDT-UHFFFAOYSA-N
Summenformel
C11H19NOS
Durchschnittliche Molmasse
213,34 g/mol
Monoisotopische Masse
213,11873523

Überblick

2-octyl-3-isothiazolone is a clear dark amber liquid. Used as a fungicide.

Namen und Bezeichner

Bevorzugter Name
2-n-Octyl-4-isothiazolin-3-one
IUPAC
2-octyl-1,2-thiazol-3-one
Lokaler Name
2-Octyl-2H-isothiazol-3-on
Englischer Name
2-Octyl-2H-isothiazol-3-one
Summenformel
C11H19NOS
Molmasse
213.34

Namen und Synonyme

Octhilinone26530-20-12-n-Octyl-4-isothiazolin-3-one2-Octyl-4-isothiazolin-3-onePancil2-Octyl-2H-isothiazol-3-one2-Octyl-3-isothiazolone2-Octyl-3(2H)-isothiazoloneSkane 8Micro-chek skane3(2H)-Isothiazolone, 2-octyl-Pancil-T
Weitere Namen anzeigen
OITOCTYLISOTHIAZOLINONEOIT-982-octyl-3(2h)-isothiazolonOIT-45kathon 893
Kathon LMMicrobicide M-8Micro-chek 11Micro-chek 11DKathon SP 70Kathon LP preservativeKathon 4200RH 893

Datenbank-Bezeichner

CAS
26530-20-1
PubChem CID
33528
DTXSID
DTXSID1025805
ChEMBL
CHEMBL1562104、CHEMBL1922512
ChEBI
CHEBI:81936
UNII
4LFS24GD0V
EC Number
247-761-7
Nikkaji
J10.439F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,5
Polarare Oberfläche (TPSA)
45,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
7
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Uses -> Biocides/Disinfectants
pHpH = 3.4
Pesticides · 4 Einträge

Fungicides

Active substance -> EU Pesticides database: Not approved

Biocide

Pesticide (Octhilinone) -> USDA PDB

LogP · 2 Einträge

log Kow = 2.45 at 24 °C

2.45

OdorVery weak, sharp smell
Density · 3 Einträge

1.04 at 60.3 °F (NTP, 1992) - Denser than water; will sink

1.03

Relative density: 1.04 at 15 °C; log Pow: 2.61 at 25 °C, pH 7

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · <25 °C
Siedepunkt
120 °C · 120°C
Dichte
1.04 · 1.04
Dampfdruck
4.9 hPa · 4.9hPa at 25℃
Brechungsindex
1.55 · 1.5500 (estimate)
Flammpunkt
23 ℃ · 23℃

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1404) of reports.

Danger

H301 (21.7%): Toxic if swallowed [Danger Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 3(2H)-Isothiazolone, 2-octyl-

3(2H)-Isothiazolone, 2-octyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3(2H)-Isothiazolone, 2-octyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2002/2076

Status: Active Update: 13-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24777

Octhilinone: HSNO Approval: HSR002932 Approved with controls

Other Safety InformationIMAP assessments - Isothiazolinones: Human health tier III assessment
DOT LabelCorrosive Poison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include irritation of the skin and severe irritation of the eyes. Corrosion also occurs.
Hazards SummaryAllergic contact dermatitis reported in workers using products containing this preservative; [Kanerva, p. 1821] Corrosive to skin and eyes; [CAMEO] See ISOTHIAZOLINONES.

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Exposure Control and Personal Protection0.05 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting Procedures · 2 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage Conditions · 1 Eintrag

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

Cleanup Methods · 1 Eintrag

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50; Species: Anas platyrhynchos (Mallard Duck) juvenile; diet >5620 ppm for 8 days /88.7% purity/

LC50; Species: Anas platyrhynchos (Mallard Duck) age 5 days; diet 1215 ppm for 8 days (95% confidence interval: 767-1914 ppm) /98.5% purity/

LD50; Species: Anas platyrhynchos (Mallard Duck) adult; oral via capsule >1000 mg/kg /100% purity/

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 10 day; diet 2542 ppm for 12 days (95% confidence interval: 1653-4083 ppm) /96% purity/

For more Ecotoxicity Values (Complete) data for Octhilinone (27 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 840(SRC), determined from a structure estimation method(2), indicates that octhilinone is expected to have very low mobility in soil(SRC). Volatilization of octhilinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 3.68X10-5 mm Hg(3), and water solubility, 500 mg/L(3). Octhilinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Octhilinone was confirmed to be biodegradable using activated sludge in the Japanese MITI test(4) suggesting that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 840(SRC), determined from a structure estimation method(2), indicates that octhilinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 3.68X10-5 mm Hg(4), and water solubility, 500 mg/L(4). According to a classification scheme(5), an estimated BCF of 19(SRC), from its log Kow of 2.45(4)] and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Octhilinone was 40-100% biodegraded in 4 weeks using the river die-away test(4) indictating that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octhilinone, which has a vapor pressure of 2.68X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase octhilinone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hrs(SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase octhilinone may be removed from the air by wet and dry deposition(SRC). Octhilinone absorbs UV light at wavelength 280 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight since sunlight consists of wavelengths above 290 nm(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: Octhilinone is used as fungicide, and biocide in cooling-tower water, paints, cutting oils, cosmetics and shampoo, as well as for leather preservation. HUMAN STUDIES: Severe allergic contact dermatitis from a paint mildewcide, octhilinone, developed in a worker formulating latex paints within a paint manufacturing company. An outbreak of severe itching, erythematous and edematous dermatitis over the extremities and upper back developed in 8 of 17 workers in the raw-materials department of a paint manufacturing factory. ANIMAL STUDIES: Guinea pig maximization testing demonstrated this to be a moderate sensitizer. No teratogenic response reported in developmental studies in rats. Octhilinone induced chromosomal aberrations in Chinese hamster ovary cells with and without metabolic activation.

Ongoing Test Status · 2 Einträge

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for octhilinone is available.[Available from, as of August 9, 2018: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]

Effluent Concentrations · 1 Eintrag

The emission sources of biocidal active substances in households have been under discussion since these substances have been detected frequently in municipal wastewater and receiving surface water bodies. Therefore, the goal of this study was to investigate the products responsible for the emission of these substances to wastewater. We analysed the wastewater of two streets for a set of biocidal active substances. Time-proportional sampling was conducted for one week of each season during one year in each street. The 14 substances analysed with liquid chromatography coupled with tandem mass spectrometry were 1,2-benzisothiazol-3(2H)-one (BIT), C12-benzalkonium chloride, carbendazim, 5-chloro-2-methyl-2H-isothiazol-3-one (CMIT), dichlorooctylisothiazolinone (DCOIT), N,N-diethyl-meta-toluamide (DEET), diuron, icaridine, 2-octyl-2H-isothiazol-3-one (OIT), piperonyl butoxide (PBO), triclosan, tebuconazole, terbutryn and tetramethrin. Using data available from household product inventories of the two streets, we searched the lists of ingredients for the products possibly being responsible for the emissions. Except for four substances, all substances have been detected in at least 10% of the samples. Highest concentrations were measured for C12-benzalkonium chloride with an average concentration in the daily samples of 7.7 ug/L in one of the streets. Next to C12-benzalkonium chloride, BIT, DEET and icaridine were detected in all samples in average concentrations above 1 ug/L in at least one street. The results show that washing and cleaning agents were important sources for preservatives such as BIT and OIT, while triclosan was apparently mainly emitted through personal care products. The mosquito repelling substances DEET and icaridine were found throughout the year, with highest emissions in summer and autumn. In conclusion, the results demonstrate that the sources of biocidal active substances in municipal wastewater are complex and that measures for the prevention of the emission of biocidal active substances into the aquatic environment have to be carried out under different legislations. This has to be taken into account discussing emission reduction at the source.

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3(2H)-Isothiazolone, 2-octyl- is included on this list. Effective date: 6/1/87; Sunset date: 12/29/88.

FIFRA Requirements · 2 Einträge

The Agency has completed its assessment of the dietary, occupational, drinking water, and ecological risks associated with the use of pesticide products containing the active ingredient OIT /2-Octyl-3(2H)-isothiazolone/. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient OIT, the Agency has sufficient information on the human health and ecological effects of OIT to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that OIT-containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measure outlined in this document is adopted; and (iii) label amendments are made to reflect this measure. Label changes are described in Section V. ... Based on its evaluation of OIT, the Agency has determined that OIT products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of OIT. If all changes outlined in this document are incorporated into the product labels, then all current risks for OIT will be substantially mitigated for the purposes of this determination. Once an Endangered Species assessment is completed, further changes to these registrations may be necessary as explained in Section III of this document.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Octhilinone is found on List B. Case No: 2475; Pesticide type: fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): 2-n-octyl-4-isothiazolin-3-one; Data Call-in (DCI) Date(s): 06/05/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
2922
hs_code
29341000
RTECS-Nr.
NX8156900
risk_code
22-23/24-34-43-50/53

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used as a preservative in polishes, paints, cleaners, adhesives, and metalworking fluids; Also used in wood and leather preservatives; [Kanerva, p. 1821]

Metal Machining [Category: Heat or Machine]

For octhilinone (USEPA/OPP Pesticide Code: 099901) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Control of apple and pear canker and other fungal and bacterial diseases of top fruit and citrus fruit. Also promotes rapid wound callousing of treated wounds and pruning cuts.

Mildewcide, microbiocide, fungicide and bacteriocide.

OIT is used to control sapstain and mold on wood via high pressure spray to logs that are processed to formulate plywood.

U.S. Production2023: <50,000 lb
Methods of Manufacturing · 2 Einträge

Octhilinone can be prepared by reaction of dithio-N-n-dioctylpropionamide and sulfuryl chloride.

Preparation: S.N. Lewis et al., France patent 1555416 corresp to United States of America patent 3761488 (1969, 1973 to Rohm & Haas).

Formulations/Preparations · 5 Einträge

The National Pesticide Information Retrieval System (NPIRS) identifies 15 companies with active labels for products containing the chemical octhilinone. To view the complete list of companies, product names and percent octhilinone in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.

Arch OIT 45 (Arch Chemicals, Inc.): Active ingredient: octhilinone 46.5%.

Densil ND Antimicrobial (Arch Chemicals, Inc.): Active ingredient: diuron 15.0%; zinc pyrithione 10.0%; and octhilinone 3.0%.

Busan 116 (Buckman Laboratories Inc.): Active ingredient: 2-(thiocyanomethylthio)benzothiazole 10.4% and octhilinone 2.2%.

For more Formulations/Preparations (Complete) data for Octhilinone (28 total), please visit the HSDB record page.

Household ProductsInformation on 61 consumer products that contain 2-N-octyl-4-isothiazolin-3-one in the following categories is provided:
Use Classification · 2 Einträge

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues

Anwendungen

BeschreibungThis isothiazolione, octylisothiazolinone, is contained in relatively fewer products than other isothiazolinones.

VerwendenFungicide. Antimicrobial agent

Anbieter50 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A member of the class of 1,2-thiazole that is 1,2-thiazol-3-one substituted on the nitrogen (position 2) by an octyl group. A fungicide and antibacterial agent, it is used for treatment of canker and other fungal and bacterial diseases in fruit trees. It i no longer approved for use within the European Union.

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