化合物详情
CAS26172-55-4
分子式C4H4ClNOS
分子量149.6 g/mol
非危品
Chloromethylisothiazolinone is a 1,2-thiazole that is 4-isothiazolin-3-one bearing a methyl group on the nitrogen atom and a chlorine at C-5. It is a powerful biocide and preservative and is the major active ingredient in the commercial product KathonTM. It has a role as an antimicrobial agent, a xenobiotic and an environmental contaminant. It is an organochlorine compound and a member of 1,2-thiazoles. It is functionally related to a methylisothiazolinone.
科学粮草官-词典编辑部,修订于:2026-07-06

Toxicity
ToxicityEPA Ecotoxicity
Pesticide Ecotoxicity Data from EPA: 42
Fate Summary
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-chloro-2-methyl-4-isothiazolin-3-one, which has a vapor pressure of 0.018 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 5-chloro-2-methyl-4-isothiazolin-3-one 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 18 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase 5-chloro-2-methyl-4-isothiazolin-3-one is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air i...
Soil Adsorption / Mobility
Ring-labeled [4,5-14C][5-chloro-2-methyl-4-isothiazolin-3-one] was very mobile in sandy loam, silt loam, clay loam, and sand soils under aerobic conditions; with Freundlich Kd values of 0.1-1.5, and in sandy loam sediment with a Freundlich Kd value of 4.9 being measured(1). Koc values were 30-144 for the soils and 310 for the sediment(1). According to a classification scheme(2), these Koc values suggest that 5-chloro-2-methyl-4-isothiazolin-3-one is expected to have very high to high mobility in soil and moderate mobility in sediment.
Environmental Biodegradation
ANAEROBIC: Microcosm studies found degradation of 5-chloro-2-methyl-4-isothiazolin-3-one to be primarily due to biodegradation based on tests using sterile controls. The half-life of 5-chloro-2-methyl-4-isothiazolin-3-one was 5 days in an anaerobic microcosm using river water and sediment(1).
Environmental Bioconcentration
A BCF of 5 was determined in bioaccumulation studies performed with bluegill sunfish(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water / Soil
The Henry's Law constant for 5-chloro-2-methyl-4-isothiazolin-3-one is estimated as 4.9X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 0.018 mm Hg(1), and water solubility, 7.3X10+5 mg/L(2). This Henry's Law constant indicates that 5-chloro-2-methyl-4-isothiazolin-3-one is expected to be essentially nonvolatile from water surfaces(3). 5-Chloro-2-methyl-4-isothiazolin-3-one's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 5-Chloro-2-methyl-4-isothiazolin-3-one is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 5-chloro-2-methyl-4-isothiazolin-3-one with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 5-chloro-2-methyl-4-isothiazolin-3-one with atmospheric ozone has been estimated as 2.5X10-19 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1); this corresponds to an atmospheric half-life of about 46 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Based upon a UV maximum of 277 nm in methanol with a log epsilon...
Artificial Pollution Sources
5-Chloro-2-methyl-4-isothiazolin-3-one's production and use as a preservative in cosmetics such as shampoos, conditioners, gels and surfactants(1) may result in its release to the environment through various waste streams(SRC). Its use as a biocide in industrial water treatment, wood treatment, oil drilling muds(2), hydraulic fracturing fluids(3) and in household products(1) will result in its direct release to the environment(SRC).
Probable Routes of Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 42,106 workers (17,003 of these were female) were potentially exposed to 5-chloro-2-methyl-4-isothiazolin-3-one in the US(1). Occupational exposure to 5-chloro-2-methyl-4-isothiazolin-3-one may occur through inhalation and dermal contact with this compound at workplaces where 5-chloro-2-methyl-4-isothiazolin-3-one is produced or used. Monitoring and use data indicate that the general population may be exposed to 5-chloro-2-methyl-4-isothiazolin-3-one via inhalation of air near consumer products and dermal contact with consumer products, such as cosmetics, containing 5-chloro-2-methyl-4-isothiazolin-3-one(SRC).
Other Environmental Concentrations
Microbiocide for oil recovery drilling muds and packer fluids - 0.34 to 34 ppm active ingredient(1).
Environmental Fate / Exposure Summary
5-Chloro-2-methyl-4-isothiazolin-3-one's production and use as a preservative in cosmetics such as shampoos, conditioners, gels and surfactants may result in its release to the environment through various waste streams. Its use as a biocide in industrial water treatment, wood treatment, oil drilling muds, hydraulic fracturing fluids and in household products will result in its direct release to the environment. If released to air, a vapor pressure of 0.018 mm Hg at 25 °C indicates 5-chloro-2-methyl-4-isothiazolin-3-one will exist solely as a vapor in the atmosphere. Vapor-phase 5-chloro-2-methyl-4-isothiazolin-3-one will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 18 hours. Vapor-pha...
Interactions
Previously we reported that brief exposure of HL60 cells to a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one (CMI) and 2-methyl-4-isothiazolin-3-one (MI) shifts the cells into a state of oxidative stress that induces apoptosis and necrosis. In this study, flow cytometric analysis showed that CMI/MI induces early perturbation of calcium homeostasis, increasing cytosolic and mitochondrial calcium and depleting the intracellular endoplasmic reticulum (ER) stores. The calcium chelator BAPTA-AM reduced necrosis and secondary necrosis, the loss of DeltaPsim and S-glutathionylation induced by necrotic doses of CMI/MI, but did not protect against CMI/MI-induced apoptosis, mitochondrial calcium uptake and mitochondrial hyperpolarization. This indicates that increased cytoplasmic calcium does...
Adverse Effects
Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Toxicity Summary
IDENTIFICATION AND USE: 5-chloro-2-methyl-4-isothiazolin-3-one (CMI) forms crystals. It is used as antimicrobial preservative in cosmetics, hygiene products, paints, emulsions, cutting oils, paper coatings, and water storage and cooling units. CMI is also used in hydraulic fracturing fluids. It is registered for pesticide 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. CMI is often used in a combination products with 2-methyl-4-isothiazolin-3-one (MI). HUMAN EXPOSURE AND TOXICITY: Kathon CG, a cosmetics preservative containing, as active ingredients, 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, appears to be a frequent cause of contact dermatitis in...
Antidote and Emergency Treatment
/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 or lorazepam...





