| Identification | More | [Name]
Mercaptodimethur | [CAS]
2032-65-7 | [Synonyms]
3,5-Dimethyl-4-(methylthio)phenol methylcarbamate
3,5-DIMETHYL-4-[METHYLTHIO]PHENYL METHYLCARBAMATE
4-METHYLTHIO-3,5-XYLYL METHYLCARBAMATE
4-[METHYLTHIO]-3,5-XYLYL-N-METHYL-CARBAMATE
BAYER 37344
ENT25726
H 321
MERCAPTODIMETHUR
Mesurol
MESUROL(R)
METHIOCARB
Methylcarbamic acid 4-(methylthio)-3,5-xylyl ester
OMS93
3,5-Dimethyl-4-(methylsulfanyl)phenyl methylcarbamate
3,5-dimethyl-4-(methylthio)-phenomethylcarbamate
3,5-dimethyl-4-methylmercaptophenyl-n-methyl-carbamate
3,5-Dimethyl-4-methylthiophenyl N-methylcarbamate
3,5-Dimethyl-4-methyl-thiophenyl-N-carbamat
3,5-dimethyl-4-methylthiophenyln-methylcarbamate
3,5-Xylenol, 4-(methylthio)-, methylcarbamate | [EINECS(EC#)]
217-991-2 | [Molecular Formula]
C11H15NO2S | [MDL Number]
MFCD00055450 | [Molecular Weight]
225.31 | [MOL File]
2032-65-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Methiocarb is a colorless crystalline powder. | [Melting point ]
119°C | [density ]
1.1838 (rough estimate) | [vapor pressure ]
1.5 x 10-5 Pa (20 °C) | [refractive index ]
1.4790 (estimate) | [storage temp. ]
0-6°C | [solubility ]
DMF: 20 mg/ml,DMSO: 20 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml,Ethanol: 10 mg/ml | [Boiling point ]
310.7±42.0 °C(Predicted) | [form ]
Crystalline Solid | [pka]
12.16±0.46(Predicted) | [color ]
White | [Water Solubility ]
Insoluble | [BRN ]
1881431 | [Stability:]
Light Sensitive | [Contact allergens]
Methiocarb is an insecticide or molluscicide with a cholinesterase inhibiting effect. A case of contact dermatitis was reported in a carnation grower. | [CAS DataBase Reference]
2032-65-7(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Methylthio-3,5-xylyl methylcarbamate(2032-65-7) | [EPA Substance Registry System]
2032-65-7(EPA Substance) |
| Hazard Information | Back Directory | [Definition]
ChEBI: A carbamate ester obtained by the formal condensation of the phenolic group of 3,5-dimethyl-4-(methylsulfanyl)phenol with the carboxy group of methylcarbamic acid. | [Uses]
Insecticide; molluscicide; bird repellent. | [General Description]
White crystalline powder with a mild odor. Used as an insecticide and immobilizing agent for birds, acaricide and molluscicide. | [Reactivity Profile]
MERCAPTODIMETHUR is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates. | [Health Hazard]
As a carbamate insecticide, this compound is a reversible cholinesterase inhibitor and acts on the nervous system. It is classified as very toxic, and the probable oral lethal dose for humans is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 150 lb. adult. | [Potential Exposure]
A potential danger to those involved
in the manufacture, formulation, and application of this
nonsystemic acaricide and insecticide. | [Fire Hazard]
When heated to decomposition, MERCAPTODIMETHUR emits very toxic fumes of nitrogen and sulfur oxides. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Speed in removing material from skin
is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this
chemical has been inhaled, remove from exposure, begin
rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit. Keep
victim quiet and maintain normal body temperature. Effects
may be delayed; keep victim under observation.
| [Shipping]
UN2757 Carbamate pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required | [Description]
Methiocarb was originally developed by Bayer as an
insecticide. The bird-repellent properties of the compound
were quickly recognized, however, and a number of
applications for bird damage management followed (42).
Methiocarb is a secondary repellent, and repellency
occurs through aversive conditioning, by which birds
that feed on treated food become sick and associate
either the food or characteristics of the food with the
discomfort (21). As a result, affected birds learn to avoid
that food item. Often the avoidance response is locationdependent.
For example, common ravens (Corvus corax)
that learn not to eat eggs at one site will still feed on
eggs at a different location (43).
| [Chemical Properties]
Methiocarb is a colorless crystalline powder. | [Waste Disposal]
In accordance with 40CFR
165 recommendations for the disposal of pesticides and
pesticide containers. Must be disposed properly by following package label directions or by contacting your local or
federal environmental control agency, or by contacting
your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform to EPA regulations governing
storage, transportation, treatment, and waste disposal.
Remove material with contaminated soil and place in
impervious containers. May be incinerated in a pesticide
incinerator at the specified temperature/dwell-time combination. Any liquids, sludges, or solid residues generated
should be disposed of in accordance with all applicable
federal, state, and local pollution control requirements. If
appropriate incineration facilities are not available, material
may be buried in a chemical waste landfill. May be amenable to biological treatment at a municipal sewage treatment
plant. (Sax/DPIMR).
| [Agricultural Uses]
Acaricide, Molluscicide, Insecticide: Used to control slugs and snails, soil insects and
spider mites in pome fruit, stone fruit, hops, strawberries,
potatoes, beets, maize, vegetables and ornamentals. Also
used as seed treatment to control fruit flies on maize and
bird repellant on berries and cherries. Methiocarb producers deleted all food uses from their product labels between
1989-92. It is A U.S. EPA restricted Use Pesticide (RUP)
except for residential application. | [Trade name]
AI3-25726®; ALCO SLUB”M[C]; B 37344®;
BAY 5024®; BAY 9026®; BAY 37344®; BAYER 37344®;
DCR 736®; DRAZA®; DRAZA G MICROPELLETS®;
H 321®; MESUROL®; METHIOCARBE®; OMS-
93®; PBI SLUG GARD®; PROVADA®; SD 9228®;
SLUG-GETA®[C] | [Pharmacology]
Methiocarb is a carbamate, and its mode of action is via
the inhibition of acetylcholinesterase at synapses in the
nervous system. Unlike many cholinesterase-inhibiting
compounds, however, the effects of methiocarb are rapidly
reversible, and the animal experiences only transitory
disruption. | [Environmental Fate]
Soil. Methiocarb was oxidized, probably by singlet oxygen, to the corresponding
sulfoxide and trace amounts (<5% yield) of sulfone when sorbed on soil and exposed to
sunlight. The photosensitized oxidation was faster in soils containing the lowest organic
carbon content (Gohre and Miller, 1986).
Plant. On and/or in bean plants, the methylthio group is rapidly oxidized to the
sulfoxide and sulfone (Abdel-Wahab et al., 1966) followed by hydrolysis yielding the
corresponding thiophenol, methylsulfoxide phenol and methylsulphonyl phenol (Har
Photolytic. When methiocarb in ethanol was irradiated by UV light, only a few
unidentified cholinesterase inhibitors were formed (Crosby et al., 1965).
Chemical/Physical. Emits toxic fumes of nitrogen and sulfur oxides when heated to
decomposition (Sax and Lewis, 1987). | [Metabolic pathway]
Methiocarb is oxidised to a sulfoxide and a sulfone in biological media.
The resulting two carbamate esters and the parent compound are hydrolysed
in soils and plants to the corresponding phenols. Hydroxylation of
the N-methyl group on the carbamate function occurs in mammalian preparations in vitro. | [storage]
Store at -20°C | [Degradation]
Methiocarb is unstable in alkaline solution. Its DT50 values at pH 4,7 and 9
(22 °C) are >1 year, 35 days and 6 hours, respectively. Photodegradation
(DT50 6-16 days) contributes to the loss of methiocarb from the environment
(PM).
River water containing methiocarb was stored in sunlight or artificial
light. Samples were taken and analysed by TLC. Methiocarb was rapidly
hydrolysed (half-life 3 days) to the phenol (2) which itself degraded
(Eichelberger and Lichtenberg, 1971). |
| Safety Data | Back Directory | [Hazard Codes ]
T;N,N,T | [Risk Statements ]
R25:Toxic if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S22:Do not breathe dust .
S37:Wear suitable gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2811/2757 | [WGK Germany ]
3 | [RTECS ]
FC5775000 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [Safety Profile]
Poison by ingestion,
skin contact, and intraperitoneal routes.
Used as an insecticide, molluscicide, and
bird repellent. When heated to
decomposition it emits very toxic fumes of
NOx and SOx. See also ESTERS and
CARBAMATES. | [Hazardous Substances Data]
2032-65-7(Hazardous Substances Data) | [Toxicity]
LD50 in male, female rats (mg/kg): 70, 60 orally (Gaines) |
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