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Home > Encyclopedia > 2-n-Octyl-4-isothiazolin-3-one

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

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

2-n-Octyl-4-isothiazolin-3-one 

structure
  • CAS No:

    26530-20-1

  • Formula:

    C11H19NOS

  • Chemical Name:

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

  • Synonyms:

    3(2H)-Isothiazolone,2-octyl-;4-Isothiazolin-3-one,2-octyl-;2-Octyl-3(2H)-isothiazolone;2-n-Octyl-4-isothiozolin-3-one;2-n-Octyl-3-isothiazolone;2-Octyl-3-isothiazolinone;Kathon LP Preservative;2-Octyl-3-isothiazolone;2-n-Octyl-4-isothiazolin-3-one;2-Octyl-4-isothiazolin-3-one;Skane M 8;RH 893;2-Octyl-4-isothiazoline-3-one;Octhilinone;Pancil;Micro-Chek 11;Micro-Chek 11D;Kathon SP 70;Kathon 893;Kathon LM;Skane 8;Pancil T;2-Octyl-4-isothiazolinone;Kathon 4200;2-n-Octylisothiazolin-3-one;Vinyzene IT 3000DIDP;Kathon 893F;Kathon 893T;A-DW;Ecoplast PA 20;Ultra-Fresh DM 25;Zonen 0/100;SD 888;4-Octylisothiazolin-3-one;Acticide 45;Acticide OTW;Microban LB 6;Zonen O 100;Rosima 243;Levanax BS 50;Biocut TR 120;OIT;Acticide WB 909;Acticide OTW 16;OTA 20;n-Octylisothiazolinone;M 8;Biotin T;OIT 99;Acticide OTA 20;OTW;Octylisothiazolinone;Acticide CSP;Skane M 8-2000;2-Octyl-2H-isothiazol-3-one;12673-72-2;53028-82-3;122667-23-6;245125-70-6;249757-59-3;1135442-68-0;1617530-25-2

  • Categories:

    Cosmetic Ingredient  >  Antimicrobials

Description

Yellow solid or clear dark amber liquid. Light Yellow Oil


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


2-octyl-3-isothiazolone is a clear dark amber liquid. Used as a fungicide.|Octhilinone is 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 is no longer approved for use within the European Union. It has a role as an environmental contaminant, a xenobiotic, an antifungal agrochemical and an antibacterial agent.

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

21334

213.34

247-761-7

4LFS24GD0V

2922

DTXSID1025805

Liquid|Light, golden yellow, clear liquid

29341000

Characteristics

45.6

3.5

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

104

<25 °C

120 °C

23℃

1.513

H2O: <01 g/100 mL at 19 ºC

Refrigerator

2.98 mm Hg at 77° F (NTP, 1992)

LD50 orl-rat: 550 mg/kg MosJN# 15AUG79

Very weak, sharp smell

pH = 3.4

Henry's Law constant = 2.07X10-8 atm-cu m/mol at 25 °C (est)

log Kow = 3.42|Stable to light|Hydroxyl radical reaction rate constant = 2.94X10-11 cu cm/molec-sec at 25 °C (est)|Ozone reaction rate constant = 1.75X10-18 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Amides and Imides

2-OCTYL-3-ISOTHIAZOLONE reacts as an isothiocyanate. Isothiocyanates are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat.

Safety Information

III

8

2922

3

22-23/24-34-43-50/53

1/2-26-36/37/39-45-60-61

NX8156900

T;N,N,T

Stable. Incompatible with strong oxidizing agents.

P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501

H302

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - 2-Octyl-3 (2H)-isothiazolone (OIT), EPA 739-R-07-008 (September 2007). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of June 15, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]

This chemical is probably combustible. (NTP, 1992)

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|H301 (12.73%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 1344 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P333+P313, P361, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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.

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.

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.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A skin and severe eye irritant.

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.

In a study of leaching of octhilinone used in facade coatings under laboratory test conditions, the compound was detected in eluants at a range of 2.5-15.1 mg/L(1).|BACKGROUND: In recent years, the frequency of contact allergy to isothiazolinones has increased alarmingly in Europe, but only limited data are available on concentrations of isothiazolinones in consumer products. OBJECTIVES: To examine the current frequency of isothiazolinones [methylisothiazolinone (MI), methylchloroisothiazolinone (MCI), benzisothiazolinone (BIT), and octylisothiazolinone (OIT)] in a wide array of detergents and cosmetics relevant for the Swiss population. METHODS: By means of a market survey, the occurrence of isothiazolinones was investigated in 1948 consumer products. Of these, 88 products were analysed by liquid chromatography-high-resolution mass spectrometry after ultrasonic extraction. RESULTS: Only 7.6% of all cosmetics contained isothiazolinones, but the prevalence in detergents was much higher (42.9%). The measured concentration ranges in detergents were 4.3-10, 3.5-279, 3.8-186 and 7.9 ppm (one product only) for MCI, MI, BIT, and OIT, respectively [corrected]. For cosmetics, these were 1.3-133 and 4.8 ppm (one product only) for MI and MCI, respectively. CONCLUSIONS: Our study has shown that high concentrations of isothiazolinones (including MI) can be found in a large variety of products, in particular in detergents. Therefore, the safe use of these preservatives should be re-evaluated by including detergents in the exposure assessment.|Recently, cases of contact dermatitis that were related to the use of polyvinyl alcohol (PVA) cooling towels containing isothiazolinone preservatives were reported in Japan. The aim of this investigation was to analyze the concentrations of five different isothiazolinone compounds present in PVA towels and to assess the effectiveness of washing in removing the preservatives from new towels prior to being used for the first time. Twenty-seven PVA towels were used in this study. Two groups (i.e., laboratory-simulation and volunteer) of washing experiments were conducted to evaluate the effect of washing procedures. Qualitative and quantitative analyses were performed by LC/MS/MS, which detected 2-methyl-4-isothiazolin-3-one (MI) and 5-chloro-2-methyl-4-isothaizolin-3-one (CMI) in 23 samples (MI: 0.29-154 ug g-wet(-1), CMI: 2.2-467 ug g-wet(-1)), 2-n-octyl-4-isothiazolin-3-one (OIT) in one sample (478 ug g-wet(-1)). The compounds 4,5-Dichloro-2-n-octyl-4-isothiazolin-3-one (2Cl-OIT) and 1,2-benzisothiazolin-3-one (BIT) were not detected in all samples. We confirmed the presence of residual MI, CMI, and OIT in the washed towels, and the residual-to-original content ratio of OIT was higher than that of MI and CMI in PVA towels, due to the higher hydrophobicity of OIT than MI and CMI. A concern has been raised about the occurrence of contact dermatitis being caused by the use of PVA towels. It is suggested that a detailed description of isothiazolinone preservatives in PVA towels and an effective washing procedure for the removal of these preservatives should be provided by the manufacturer. Further, alternative non-sensitizing preservatives might be considered for the manufacture of PVA cooling towels in the future.

Toxicity

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.

LD50 Rabbit dermal 690 mg/kg|LD50 Rat oral 550 mg/kg

Ochilinone's production may result in its release to the environment through various waste streams; its use as a plant wound protectant, fungicide/bactericide(1) and cooling-tower biocide(2,3) will result in its direct release to the environment(SRC). Octhilinone's production and use as a biocide in paints, cutting oils and for leather preservation(1) may result in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of octhilinone with photochemically-produced hydroxyl radicals has been estimated as 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A half-life in air of 3.3 hours has also been reported(2). The rate constant for the vapor-phase reaction of octhilinone with ozone has been estimated as 1.8X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). Octhilinone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Octhilinone absorbs UV light at wavelength 280 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight since sunlight consists of wavelengths above 290 nm(SRC).

An estimated BCF of 19 was calculated in fish for octhilinone(SRC), using a log Kow of 2.45(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of octhilinone can be estimated to be 850(SRC). According to a classification scheme(2), this estimated Koc value suggests that octhilinone is expected to have low mobility in soil(SRC). A Koc of 179.8 at 20 °C has also been reported(3). Octhilinone, at a concentration of 10 ug/L, was <90% absorbed over 6 hours using a German municipal waste water treatment plant activated sludge in a bench-scale test(4).

The Henry's Law constant for octhilinone is estimated as 2.1X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 3.68X10-5 mm Hg(1), and water solubility, 500 mg/L(1). This Henry's Law constant indicates that octhilinone is expected to be essentially nonvolatile from water and moist soil surfaces(2). Octhilinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SEAWATER: SeaNine 211, with 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) being the biocidal ingredient, is a widely-used antifouling agent to deter the undesirable biofouling phenomenon. It is commercially promoted as an environmentally acceptable antifoulant mainly due to its claimed rapid degradation in marine environment. However, increasing researches document varying degradative kinetics in different environments, proving that SeaNine 211 is actually not degraded equally fast around the world (half-life between <1day and 13.1days). Large-scale application of SeaNine 211 in antifouling coatings has also caused global contamination of marine environment in various compartments. For example, accumulation of SeaNine 211 is detected as high as 3700 ng/L in Spanish seawater and 281ng/g dry weight in Korean sediment. Considering that SeaNine 211 is highly toxic against non-target marine organisms, environmental risk assessment finds that most marine organisms are endangered by SeaNine 211 in worst-case scenario. Its endocrine disrupting and reproductive impairing effects at environmentally worst-case concentrations further constitute a long-term threat to the maintenance of population stability. Therefore, in the light of the varying degradability, environmental pollution and high toxicity, especially the endocrine disruption, SeaNine 211 as an antifouling agent is likely to cause non-negligible damages to the marine ecosystem. There is an urgency to perform a systematic ecological risk assessment of SeaNine 211 to prevent the potential impacts on the health of marine environment. A regular monitoring also becomes necessary to place the usage of antifouling biocides under control. /4,5-Dichloro-2-n-octyl-4-isothiazolin-3-one /

Occupational exposure to octhilinone may occur through inhalation and dermal contact with this compound at workplaces where octhilinone is produced or used. Use data indicate that the general population may be exposed to octhilinone via dermal contact with consumer products containing octhilinone. (SRC)

Drug Information

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin and severe irritation of the eyes. Corrosion also occurs. ACUTE/CHRONIC HAZARDS: This compound is corrosive to tissues. It is moderately toxic by skin contact and ingestion. When heated to decomposition it emits toxic fumes IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Preparations of 2-n-octyl-4-isothiazolin-3-one (Skane M-8) at 1000 p.p.m. a.i. and 500 p.p.m. a.i. in petrolatum induced allergy in a cumulative insult human patch test. Challenge patch testing using 250 p.p.m. a.i. Skane M-8 elicited allergy in 6 out of 6 sensitized individuals. Sensitized individuals did not cross react with Kathon biocide, (Kathon CG), a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one. All petrolatum preparations to which Tween 85 was added at 2.5% produced mild irritation in cumulative insult patch tests, but no irritation was observed with Tween 85 at 0.625%. We conclude that Skane M-8, 250 p.p.m. a.i. with Tween 85 0.625% in petrolatum is appropriate for patch testing for Skane M-8 allergy.|/CASE REPORTS/ Severe allergic contact dermatitis from a paint mildewcide, 2-n-octyl-4-isothiazolin-3-one, developed in a worker formulating latex paints within a paint manufacturing company, Guinea pig maximization testing demonstrated this to be a moderate sensitizer. Further cases of allergic contact dermatitis may be encountered as the use of this biocide increases in the market place.|/CASE REPORTS/ 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. The outbreak occurred during a 2-month period when Acticide EP paste was used in place of Metatin as a microbiocide. To evaluate the frequency and the etiologic agent of this outbreak, a plant walk-through, examination and review of photographs of skin lesions followed by statistical analysis for association between the development of dermatitis and exposure to Acticide paste were performed. Three guinea pigs were subjected to patch tests comparing the dermatotoxicity of Acticide EP and Metatin. The results showed that 8 out of 17 workers (47%) suffered from contact dermatitis during the 2-month period. Stratification by occupational exposure further confirmed the association between the development of dermatitis and exposure to the Acticide paste. The dermatotoxicity test on guinea pigs revealed the marked corrosive effect of the paste and the absence of dermatotoxicity of Metatin. After the removal of the paste from the raw material, there were no new cases of contact dermatitis at the 6 month follow-up. We conclude that Acticide EP paste was the responsible offending agent. Because isothiazolinone derivatives are well-known antigens and 2-n-octyl-4-isothiazolin-3-one is the active ingredient in Acticide EP paste, 2-n-octyl-4-isothiazolin-3-one is the likely cause of the dermatitis.|/EPIDEMIOLOGY STUDIES/ 2-N-octyl-4-isothiazolin-3-one (OIT) is an antimicrobial agent that is mainly used in industrial settings. The objective of the study was to find the significance of OIT contact allergy at our clinic of occupational dermatology. We looked through our patient material from 1991 for allergic reactions to OIT and analyzed the clinical records. We found 8 patients with ordinary allergic reactions to OIT and 1 late reaction. 2 workers in the manufacture of paints had occupational allergic contact dermatitis from OIT in biocides. 2 patients were machinists and 3 were female farmers: in these cases, however, we could not find any exposure. A sewing machine operator had patch test reactions to 2 of her mattress textiles, and chemical analysis of them showed 40-50 parts per million OIT. In conclusion, OIT is a rare sensitizer, and its contact allergies occur mainly in paint manufacturing. It is infrequently used in metal-working fluids and possibly sensitizes machinists. Although it is also used in some biocides recommended for use in the textile industry, there are no previous reports of contact allergy in this field. Our sewing machine operator with OIT contact allergy had probably been sensitized from mattress textiles.

2-n-octyl-4-isothiazolin-3-one

2-n-Octyl-4-isothiazolin-3-one Use and Manufacturing

Methods of Manufacturing

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).

Uses

Fungicide. Antimicrobial agent Fungicide. Biocide in cooling-tower water, paints, cutting oils, cosmetics and shampoo; for leather preservation. 2-n-Octyl-4-isothiazolin-3-one is a mildeweide; bactericide; fungicide; biocide in cooling-tower water; in paints, cutting oils, cosmetics, and shampoos; leather preservation; wound protectant for pruning cuts.

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.

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

This paper describes the development of a multi-residue method for the determination of 36 emerging organic pollutants (26 biocides, 5 UV-filters and 5 benzothiazoles) in raw and treated wastewater, activated sludge and surface water using liquid chromatography-tandem mass spectrometry (LC-MS/MS). The target analytes were enriched from water samples adjusted to pH 6 by solid-phase extraction (SPE) on Oasis HLB 200 mg cartridges and eluted with a mixture of methanol and acetone (60/40, v/v). Extraction of freeze-dried sludge samples was accomplished by pressurized liquid extraction (PLE) using a mixture of methanol and water (50/50, v/v) as extraction solvent followed by SPE. LC-tandem MS detection was compared using electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) in positive and negative ionization mode. ESI exhibited strong ion suppression for most target analytes, while APCI was generally less susceptible to ion suppression but partially leading to ion enhancement of up to a factor of 10. In general, matrix effects could be compensated using stable isotope-labeled surrogate standards, indicated by relative recoveries ranging from 70% to 130%. In wastewater, activated sludge and surface water up to 33 analytes were detected. Maximum concentrations up to 5.1 and 3.9 ug/L were found in raw wastewater for the water-soluble UV-filters benzophenone-4 (BZP-4) and phenylbenz-imidazole sulfonic acid (PBSA), respectively. For the first time, the anti-dandruff climbazole was detected in raw wastewater and in activated sludge with concentrations as high as 1.4 ug/L and 1.2 ug/gTSS, respectively. Activated sludge is obviously a sink for four benzothiazoles and two isothiazolones, as concentrations were detected in activated sludge between 120 ng/gTSS (2-n-octyl-4-isothiazolin-3-one, OIT) to 330 ng/gTSS (benzothiazole-2-sulfonic acid, BTSA).

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|Agrochemicals -> Fungicides

Computed Properties

Molecular Weight:213.34
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:213.11873540
Monoisotopic Mass:213.11873540
Topological Polar Surface Area:45.6
Heavy Atom Count:14
Complexity:204
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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