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| | Mercaptodimethur Basic information |
| | Mercaptodimethur Chemical Properties |
| 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 | | form | Crystalline Solid | | Boiling point | 310.7±42.0 °C(Predicted) | | pKa | 12.16±0.46(Predicted) | | color | White | | Water Solubility | Insoluble | | BRN | 1881431 | | Stability: | Light Sensitive | | 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 | Methiocarb (2032-65-7) |
| | Mercaptodimethur Usage And Synthesis |
| 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. | | Uses | Insecticide; molluscicide; bird repellent. | | Uses | Methiocarb is an insecticide, molluscicide and acaricide with contact
and stomach action. It is used to control slugs, snails and insects in a
wide range of crops. Soil insects are controlled. Methiocarb is also used as
a seed-treatment and bird repellent. | | Uses | Insecticide, acaricide and bird repellent. | | 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. | | 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, Mercaptodimethur 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. | | Health Hazard | Highly toxic cholinesterase inhibitor; exhibitsacute, delayed and chronic effects; routesof entry — ingestion, skin absorption andinhalation of vapors; reversible action ofshort duration; toxic symptoms includesalivation, lacrimation, bradycardia, blurredvision, labored breathing, headache, muscle twitching, tremor, and slight paralysis;gastrointestinal effects include nausea, vomiting, abdominal pain, and diarrhea; severepoisoning may lead to convulsions and coma;oral intake of probably 5–10 g may be fatalto adult humans.
LD50 oral (rat): 15–20 mg/kg
LD50 oral (guinea pig): 40 mg/kg
LD50 skin (rat): 350 mg/kg
LD50 skin (wild bird): 100 mg/kg. | | Fire Hazard | When heated to decomposition, Mercaptodimethur emits very toxic fumes of nitrogen and sulfur oxides. | | 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] | | Contact allergens | Methiocarb is an insecticide or molluscicide with a cholinesterase inhibiting effect. A case of contact dermatitis was reported in a carnation grower. | | 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. | | 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. | | Potential Exposure | A potential danger to those involved
in the manufacture, formulation, and application of this
nonsystemic acaricide and insecticide. | | 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. | | 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 | | 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). | | 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).
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| | Mercaptodimethur Preparation Products And Raw materials |
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