Grundinformationen
- Standard-SMILES
CN=C=S- InChIKey
LGDSHSYDSCRFAB-UHFFFAOYSA-N- Summenformel
- C2H3NS
- Durchschnittliche Molmasse
- 73,12 g/mol
- Monoisotopische Masse
- 72,9986201
Überblick
Methyl isothiocyanate appears as a colorless liquid with a sharp odor. Lethal by inhalation of even small quantities of vapor. Does not have odor warning characteristics at low concentrations. Do not rely on the sense of smell to warn about the presence of vapors. Denser than water. May cause tearing and irritate the eyes, skin, nose and throat.
Namen und Bezeichner
- Bevorzugter Name
- Methyl isothiocyanate
- IUPAC
- methylimino(sulfanylidene)methane
- Lokaler Name
- Methylisothiocyanat
- Englischer Name
- Methyl isothiocyanate
- Summenformel
- C2H3NS
- Molmasse
- 73.12
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
556-61-6- PubChem CID
- 11167
- DTXSID
DTXSID2027204- ChEMBL
CHEMBL396000- ChEBI
CHEBI:78337- UNII
- RWE2M5YDW1
- EC Number
- 209-132-5
- Nikkaji
- J3.295F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 44,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 4
- Formalladung
- 0
- Komplexität
- 44
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Nitrogen Compounds -> Isothiocyanates
Flammable agents - 3rd degree
Pesticides
Fungicides, Herbicides, Insecticides, Nematicides
Active substance -> EU Pesticides database: Not approved
Environmental transformation -> Pesticide transformation products (metabolite, successor)
LogP
log Kow = 0.94
0.94
0.94
Density
1.069 at 98.6 °F (EPA, 1998) - Denser than water; will sink
1.0691 at 37 °C/4 °C
0.938-0.942
1.069 @ 37°C
Color/Form
Colorless crystals
Solid at room temperature but sublimes directly to a gas.
Solubility
Readily soluble in common organic solvents, such as ethanol, methanol, acetone, cyclohexanone, dichloromethane, chloroform, carbon tetrachloride, benzene, xylene, petroleum ether, and mineral oils.
Very soluble in ethyl ether
In water, 7.6X10+3 mg/L at 25 °C
7.6 mg/mL at 20 °C
Very slightly soluble in water; freely soluble in ether
Soluble (in ethanol)
Flash Point
20 °F
95 °F (35 °C) (closed cup). /MITC-Fume/
Boiling Point
246 °F at 760 mmHg (EPA, 1998)
119 °C
117.00 to 118.00 °C. @ 760.00 mm Hg
117-118 °C
119 °C @760 [mm Hg]
Physikochemische Eigenschaften
- Schmelzpunkt
- 30 · 30-34 °C(lit.)
- Siedepunkt
- 117 · 117-118 °C(lit.)
- Dichte
- 1.069 g/mL · 1.069 g/mL at 25 °C(lit.)
- Dampfdruck
- 21 mm · 21 mm Hg ( 20 °C)
- Brechungsindex
- 37 · nD37 1.5258
- FEMA
- 4426 · 4426 | METHYL ISOTHIOCYANATE
- Flammpunkt
- 90 °F · 90 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 O: · H2O: slightly soluble
- Aggregatzustand
- Low Melting Solid
- Farbe
- White to pale yellow
- Geruch (Odor)
- 0.01 % · at 0.01 % in propylene glycol. pungent mustard horseradish
- Geruchsart
- pungent
- Biologische Quelle
- rabbit
- Wasserlöslichkeit
- 7.6 g/L · 7.6 g/L
- Merck
- 14 · 14,6092
- JECFA Number
- 1884 · 1884
- Specific Activity
- 19 · 19-25nmol/min·mg
- BRN
- 605319 · 605319
- Henry's Law Constant
- 1.7 · 1.7×10-1 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
- Stabilität
- Stable. Incompatible with strong oxidizing agents, alcohols, strong bases, amines.
- InChIKey
- LGDSHSYDSCRFAB-UHFFFAOYSA-N
- LogP
- 1.3 at · 1.3 at 20℃
- CAS Datenbank
- 556 · 556-61-6(CAS DataBase Reference)
- NIST chemische Informationen
- Methane, isothiocyanato-(556-61-6)
- EPA chemische Informationen
- Methyl isothiocyanate (556-61-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H301 (100%): 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, P319, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Chemical: Methane, isothiocyanato-
Commission Regulation (EC) No 1490/2002
2002/2076
Status: Active Update: 23-07-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/11490
Methane, isothiocyanato-: HSNO Approval: HSR001541 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
(Non-Specific -- Pesticide, Solid, n.o.s.) This material may burn, but does not ignite readily. Fire may produce irritating or poisonous gases. When heated it emits very dangerous cyanides and sulfur compounds. Do not store below -4F or at elevated temperatures. Keep away from sparks. (EPA, 1998)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Very toxic; probable human oral lethal dose is 50-500 mg/kg, or between 1 teaspoonful and 1 oz. for a 70 kg (150 lb.) person. Highly irritating to skin, mucous membrances, and eyes. Human oral minimum lethal dose: approximately 1 g/kg. (EPA, 1998)
· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.
Hazards Summary
A strong irritant, vesicant, and lacrimator; Inhalation of high concentrations can cause bronchoconstriction, lung injury, seizures, and coma; [HSDB] May cause second or third degree burns after brief skin contact. [CHRIS] Reacts with water producing carbon dioxide and methylamine; [CAMEO] A strong skin sensitizer in animal studies; [Reference #2] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; May cause skin sensitization and lachrymation; Toxic by ingestion and inhalation; [Alfa Aesar MSDS]
Special Reports
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Amended Reregistration Eligibility Decision (RED) for the Methyldithiocarbamate Salts (Metam-sodium, Metam-potassium) and Methyl Isothiocyanate (MITC), EPA 738-R-09-310 (May 2009). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 24, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]
USEPA; Chemical Profile: Methyl Isothiocyanate (1985). Chemical safety information sheet.
FIFRA Requirements
Section 4(g)(2)(A) of the Federal Insecticide, Fungicide and Rodenticide Act (FIFRA) calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether pesticides containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient specific) data to support reregistration of products containing ... MITC /methyl isothiocyanate/. ... Based on a review of the ... MITC databases and public comments on the Agency's assessments for these active ingredients, the Agency has sufficient information on the human health and ecological effects of ... MITC to make decisions as part of the reregistration process under FIFRA. Further, based on the volatility of ... MITC and metabolism studies in plants, EPA has concluded that there is a reasonable expectation that no residue on food or feed items will occur with the use of these fumigants. Therefore, no tolerances have been established. ... As a result of this review, the Agency has determined that certain uses of ... MITC (for use as an antimicrobial agent to treat wood poles and pilings) are eligible for reregistration, provided that the risk mitigation measures outlined in this document are adopted, label amendments are made to reflect these measures (as outlines in Section V), and data are developed to assess intermediate- and long-term risk to bystanders.
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 saftey 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. Methyl isothiocyanate is found on List B. Case No: 2405; Pesticide type: Insecticide, fungicide, herbicide; 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 Reregistration Eligibility Decision (RED) document; Active ingredient (AI): methylisothiocyanate; Data Call-in (DCI) Date(s): 07/26/91; 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.
Sicherheit und Schutzausrüstung
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Warning: Methyl isothiocyanate is very toxic and highly irritating to skin, mucous membranes, and eyes. Caution is advised.
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Fire Fighting Procedures
Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of waiter may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. use "alcohol" foam, dry chemical or carbon dioxide.
Extinguishing Media: Water fog, foam, CO2, dry chemical. /MITC-Fume/
Evacuate enclosed and surrounding areas. If smoke and fumes cannot be avoided, use proximity suit and self-contained breathing apparatus. Use water spray to cool containers and disperse vapors. Keep spills away from sources of ignition. /MITC-Fume/
Where there is a fire involving isocyanates, carbon dioxide or powder extinguishers must be employed. Firemen must be equipped with self-contained breathing apparatus. /Isocyanates/
Storage Conditions
Store only in closed original container to prevent leakage. Store only in cool, well-ventilated, locked areas, away form food and feedstuff, out of reach of children and irresponsible persons. Avoid exposure to heat and/or direct sunlight. Do not drop container onto or slide across sharp objects. /MLPC Methylisothiocyanate (MITC)/
Isocyanates are transported in railroad tank cars, tank trucks, tanks in ships, containers, and drums. They are stored in steel tanks and processed in steel equipment. For long-term storage stainless steel is recommended. To avoid contamination by atmospheric moisture, a dry air or inert gas blanket is essential. /Isocyanates/
Isocyanates are transported in railroad tank cars, tank trucks, tanks in ships, containers, and drums. They are stored in steel tanks and processed in steel equipment. For long-term storage stainless steel is recommended. To avoid contamination by atmospheric moisture, a dry air or inert gas blanket is essential. /Isocyanates/
Cleanup Methods
Decontamination of spilled isocyanates and disposal of isocyanate waste are best conducted by using aqueous ammonia (3-8% concentrated ammonia solution in 90-95% water with 0.2-5% liquid detergent) or aqueous sodium carbonate (5-10% sodium carbonate in 90-95% water and 0.2-5% liquid detergent). An alcoholic solution (50% ethanol, isopropyl alcohol, or butanol; 45% water; and 5% concentrated ammonia) may be preferred because of the low miscibility of isocyanates with water. /Isocyanates/
Steps to be taken in case material is released or spilled: Cover with cold water. Product will solidify. Recycle, if possible or add solid scale in small amounts to drum with 10% aqueous ammonia solution. Product will react with ammonia to form N-Methyl thiourea. /MITC-Fume/
Decontamination of spilled isocyanates and disposal of isocyanate waste are best conducted by using aqueous ammonia (3-8% concentrated ammonia solution in 90-95% water with 0.2-5% liquid detergent) or aqueous sodium carbonate (5-10% sodium carbonate in 90-95% water and 0.2-5% liquid detergent). An alcoholic solution (50% ethanol, isopropyl alcohol, or butanol; 45% water; and 5% concentrated ammonia) may be preferred because of the low miscibility of isocyanates with water. /Isocyanates/
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Preventive Measures
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
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.
For terrestrial uses: Do not apply directly to water or to areas where surface water is present or to intertidal areas below the mean high water mark. /MLPC Methylisothiocyanate (MITC)/
Users must wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Users must remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Users must remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon aSJlOssible, wash thoroughly. /MLPC Methylisothiocyanate (MITC)/
For more Preventive Measures (Complete) data for METHYL ISOTHIOCYANATE (12 total), please visit the HSDB record page.
Isolation and Evacuation
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Immediate precautionary measure
Small spill:
Small spill:
Protective Action Criteria (PAC)
0.27 [mg/m3]
17 [mg/m3]
50 [mg/m3]
Toxikologische Informationen
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Ecotoxicity Values
EC50; Species: Scenedesmus subspicatus (Green Algae); Conditions: freshwater, static; Concentration: 254 ug/L for 96 hr (95% confidence interval: 218-296 ug/L); Effect: population abundance /95.7% pure formulation/
EC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, flow through; Concentration: 55 ug/L for 48 hr; Effect: intoxication, immobilization /95% pure formulation/
LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/L; Concentration: 80 ug/L for 14 days (95% confidence interval: 32-100 ug/L) /formulation/
LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/L; Concentration: 280 ug/L for 48 hr (95% confidence interval: 180-560 ug/L) /formulation/
For more Ecotoxicity Values (Complete) data for METHYL ISOTHIOCYANATE (10 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 3-14.5(2-5(2) indicates that methyl isothiocyanate is expected to have very high mobility in soil(SRC). Volatilization of methyl isothiocyanate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 3.54 mm Hg(6), and water solubility, 7.6X10+3 mg/L(7). Methyl isothiocyanate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Using the first order kinetics, the biodegradation half-life in soil was estimated to range from 0.5 to 50 days(8) suggesting that biodegradation may be an important environmental fate process in soil, depending on conditions(SRC).
TERRESTRIAL FATE: In damp soil, degradation and evaporation of the bulk of the substance occurs within 3 weeks at 18-20 °C soil temperature, 4 weeks at 6-12 °C, and 8 weeks at 0-6 °C. At the lower temperatures, leaching is more significant and is dependent on soil moisture(1).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 3-14.5(2-5) indicate that methyl isothiocyanate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(6) based upon an estimated Henry's Law constant of 4.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 3.54 mm Hg(7), and water solubility, 7.6X10+3 mg/L(8). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 19 hrs and 9 days, respectively(SRC). According to a classification scheme(9), an estimated BCF of 3(SRC), from its log Kow of 0.94(10) and a regression-derived equation(11), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis half-lives in a buffered system were determined to be 65 and 178 days at 25 and 0 °C, respectively, and a pH of 7.0(12). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(13) indicating that biodegradation is not an important environmental fate process in water(SRC).
AQUATIC FATE: As a result of a spill on July 14, 1991 into the Sacramento River near Mount Shasta, CA of metam-sodium from seven derailed train cars, methyl isothiocyanate was detected in water and sediment samples along the 68 km river stretch, from spill site to the entrance of Lake Shasta(1). Concentrations ranged from 25 ppm to 15 ppm over the course of 4 days, formed as a result of oxidation of metam-sodium(1).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl isothiocyanate, which has a vapor pressure of 3.54 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl isothiocyanate 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 78 days(SRC), calculated from its rate constant of 1.36X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Methyl isothiocyanate is sensitive to light(4), and therefore may be susceptible to direct photolysis by sunlight(SRC). The half-life for gas-phase photolysis of methyl isothiocyanate was 10 hrs in quartz containers(5).
Toxicity Summary
Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Ecotoxicity Excerpts
/PLANTS/ Phytotoxic to all green plants.
/FIELD STUDIES/ On July 14, 1991, 72,000 L of the pesticide Metam (active ingredient, methyl isothiocyanate) was accidentally released into the Upper Sacramento River. /It was/ hypothesized that the spill affected streamside microbial communities and that the effects were persistent. To address this hypothesis, ...river soils /were sampled/ a year later from sites above and below the spill as well as from an agricultural area and determined soil carbon dioxide efflux (as a measure of soil respiration) in response to methyl isothiocyanate in controlled-environment microcosms, resulting in estimates of the EC50 and soil degradation rates of methyl isothiocyanate. The soil respiration EC50s for the river soils ranged from 13.2 to 51.4 ug/g methyl isothiocyanate, whereas that of the agricultural soil was 72.2 ug/g. Thus, the soils from the Upper Sacramento River were more sensitive to the toxicologic effects of methyl isothiocyanate than was the agricultural soil. Soils from below the spill site also showed higher (factor two or more) EC50s than soils from reference locations above the spill site. The half-life of methyl isothiocyanate in soils ranged from 2.7 to 6.9 days and was longer by a factor of two in the river soils. These degradation rates are controlled by both biotic (microbial) and abiotic processes. The presence of a microbial community accelerated the degradation rate by a factor of two. The pattern of EC50 data demonstrates that changes in the microbial community in the river soils were persistent a full year after the spill and that the stress elicited responses that were indicative of physiologic accommodation or selection for resistance at the population, species, and/or community level.
Soil Adsorption/Mobility
The Koc of methyl isothiocyanate ranges from 3 to 14.5(1-4). According to a classification scheme(5), this Koc range suggests that methyl isothiocyanate is expected to have very high mobility in soil(SRC). Methyl isothiocyanate was shown to leach readily using repacked soil columns; nearly all the applied solution was recovered in the leachate(6). Using a soil column study that simulated environmental Moroccan conditions (0.84% organic matter, pH 7.6, 12.5% moisture, 4.28% clay, 12.32% loam, 83.41% sand), methyl isothiocyanate was shown to concentrate at the 0-40 cm soil layer within 24 hours(7).
Atmospheric Concentrations
SOURCE DOMINATED: Following injection of metam-sodium into soil in 2 fields in the Netherlands, concentrations of methyl isothiocyanate in downwind air around these fumigated fields were greater than 3 ug/cu m 1 day after fumigation; 7 to 9 days later the concentrations ranged from less than 1.6 to 2.9 ug/cu m(1). Residential expansion into traditionally agricultural areas in South Franklin County, Washington has resulted in increased non-occupational exposure to methyl isothiocyanate following center-pivot chemigation field application of metam-sodium. Air samples were collected between Sept 26, 2005 and Oct 25, 2005; a maximum concentration of 67 ug/cu m within 12 hours of a fall fumigation on October 21, 2005(2). Following application of metam-sodium at 480 L/ha, maximum concentration of methyl isothiocyanate were 11.2 and 7.4 ug/cu m at 10 cm above ground 6-8 hours following application and minimum concentrations were 0.7 and 0.2 ug/cu m observed at 200 ug/cu m 30-35 hrs after chemigated and injected fields, respectively(3).
Regulatorische Informationen
FIFRA Requirements
Section 4(g)(2)(A) of the Federal Insecticide, Fungicide and Rodenticide Act (FIFRA) calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether pesticides containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient specific) data to support reregistration of products containing ... MITC /methyl isothiocyanate/. ... Based on a review of the ... MITC databases and public comments on the Agency's assessments for these active ingredients, the Agency has sufficient information on the human health and ecological effects of ... MITC to make decisions as part of the reregistration process under FIFRA. Further, based on the volatility of ... MITC and metabolism studies in plants, EPA has concluded that there is a reasonable expectation that no residue on food or feed items will occur with the use of these fumigants. Therefore, no tolerances have been established. ... As a result of this review, the Agency has determined that certain uses of ... MITC (for use as an antimicrobial agent to treat wood poles and pilings) are eligible for reregistration, provided that the risk mitigation measures outlined in this document are adopted, label amendments are made to reflect these measures (as outlines in Section V), and data are developed to assess intermediate- and long-term risk to bystanders.
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 saftey 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. Methyl isothiocyanate is found on List B. Case No: 2405; Pesticide type: Insecticide, fungicide, herbicide; 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 Reregistration Eligibility Decision (RED) document; Active ingredient (AI): methylisothiocyanate; Data Call-in (DCI) Date(s): 07/26/91; 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.
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methyl isothiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Sicherheitsdaten
- F
- 21
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2477
- hs_code
- 29309090
- RTECS-Nr.
- PA9625000
- risk_code
- 23/25-34-43-50/53
- Toxizität
- LD50 in rats, mice (mg/kg): 220, 110 orally; in rabbits (mg/kg): 33 dermally (Vernot); LD50 s.c. in mice: 0.05 g/kg (Klesse, Lukoschek)
- hazard_code
- T,N
- safety_code
- 36/37-38-45-60-61
- hazard_class
- 6.1
- packing_group
- I
- Speicherklasse
- 10 - Combustible liquids
- Giftige Stoffe Daten
- 556-61-6(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
The metabolism of /several compounds, including/ ... methyl isocyanate ... in rats and mice using various carbon-14 (C-14) and carbon-13 (C-13) labeled preparations was studied ... . Male albino-Swiss-Webster-mice were treated intraperitoneally with C-14 labeled compounds at 0.05 millimolar/kilogram body weight. Urine, feces, and carbon-dioxide were collected and the mice were sacrificed at 6, 24, or 48 hours for tissue analysis. Male Sprague-Dawley-rats were treated intraperitoneally with C-14 labeled compounds as for mice, and with C-13 labeled compounds orally, intraperitoneally, and intraperitoneally with cannulation with ... 33mg/kg MITC... in mice, most of the C-14 labeled compounds were in the urine, with a small portion in the body. S-(N-methyl-thiocarbonyl)glutathione was a major metabolite in the urine. In rats, the major metabolites were S-(N-methyl-thiocarbonyl)glutathione in bile and S-(N-methyl-thiocarbonyl)mercapturic-acid in the urine ... . Glutathione detoxification involved direct reaction for MITC, glutathione-S-transferase catalyzed reaction for metham... .
Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
MeSH Pharmacological Classification
Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed)
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and Excretion
A study from the open literature determined the fate of radiolabeled metam and MITC following intraperitoneal injection of mice (Swiss-Webster, male). ... A mean value of 58% of the metam and 80% of the MITC was excreted in mouse urine by 48 hours. Feces, expired CO2 and carcass accounted for 6, 5 and 7.5% of the total metam dose, respectively, and 5, 4 and 6% of the total MITC dose in mice. Radioactive label was widely distributed among tissues. Liver, kidney and, interestingly, hair, accounted for the largest proportions of the tissue fraction for both metam and MITC....
Tissue content following MITC administration was highest in the thyroid at 168 hours, with liver, kidneys, whole blood and adrenals comprising relatively high secondary sites of accumulation. Female lungs at the high dose were also important sites. Total tissue levels at 168 hours did not exceed 2.3% of the administered dose of ... MITC at either the low or high doses.
The oral-exposure metabolism study compared the absorption, tissue distribution, and excretion of metam sodium and MITC. Rats were given radiolabeled metam sodium at 10 or 100 mg/kg, or MITC at 4.4 or 33 mg/kg by gastric gavage. Feces were collected at 24-hr intervals for up to 7 days. Expired air was collected at 24-hr intervals for up to 3 days, passing through a series of 3 traps capable of selectively capturing MITC, CO2 and carbonyl sulfide - CS2, respectively. ... MITC appeared to be even more readily taken up; by 24 hr 88-96% of the dose was absorbed, increasing to 94-100% by 168 hours.
The metabolism of methyl, ethyl, butyl and allyl isothiocyanate, which occur as glucosinolates in a number of plants, was studied. Oral administration of the substances to the rat was followed by their renal excretion as mercapturic acids, which were isolated as dicyclohexylamine salts. ... The mercapturic acids were very labile dithiocarbamidic acid esters, formed by the addition of the isothiocyanate group to the SH group of the cysteine component.
Verwendung und Herstellung
Uses
Used as an insecticide and soil fumigant; Possibly used as a chemical weapon; [HSDB] A breakdown product of the soil fumigant metam sodium; [Murray, p. 1830] The primary degradate of metam sodium and metam potassium that is responsible for their soil fumigant properties; Used as an antimicrobial on wood poles and pilings; [Reference #2]
Applying Wood Preservatives [Category: Other]
For methyl isothiocyanate (USEPA/OPP Pesticide Code: 068103) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Antimicrobial agent to treat wood poles and pilings
Pesticide; soil fumigant
A possible military poison
U.S. Production
(1988) No data published
Methane, isothiocyanato- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5958]
Methods of Manufacturing
Methyl isothiocyanate may be made by reacting sodium methyldithiocarbamate with ethyl chlorocarbonate.
Obtained by the action of CS2 on methylamine.
Metam-sodium (dethiolation)
Formulations/Preparations
USEPA/OPP Pesticide Code 068103; Trade Names: Trapex, Vorlex, component of (with 029001 and 029002), Biomet 33.
MITC is formulated as a solidified-melt, where it is a solid at ambient conditions and melts and vaporizes at elevated temperatures found within the pole being treated.
Methylisothiocyanate (MITC) (MLPC International): Methyl isothiocyanate 97%.
Technical grade is greater than 94.5% pure
For more Formulations/Preparations (Complete) data for METHYL ISOTHIOCYANATE (7 total), please visit the HSDB record page.
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Environmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information
Methane, isothiocyanato-: ACTIVE
The WHO Recommended Classification of Pesticides by Hazard identifies methyl isothiocyanate (technical grade) as Class II: moderately hazardous; Main Use: fungicide-applied to soil: not used with herbicides or plant growth regulators.
Introduced by Schering AG (now Bayer AG).
Decomposition product of dazomet.
It was registered in 1987 for treatment of laminated wood products and large structural timbers such as utility poles, pilings, and bridge timbers.
For more General Manufacturing Information (Complete) data for METHYL ISOTHIOCYANATE (6 total), please visit the HSDB record page.
Anwendungen
BeschreibungMethyl iso thio cyanate is the organo sulfur compound with the formula CH3N = C = S . This low melting colorless solid is a powerful lachrymator. As a precursor to a variety of valuable bioactive compounds, it is the most important organic iso thio cyanate in industry.
OccurrenceReported found in horseradish.
VerwendenUsually used to study the effect of pesticide Metam (methyl isothiocyanate is its active ingredient) in the streamside microbial communities of the upper Sacramento river
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: An isothiocyanate having a methyl group attached to the nitrogen.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…