137-42-8 Usage
Uses
Used in Agricultural Industry:
Metham sodium is used as a fungicide, nematicide, herbicide, and soil fumigant for controlling weeds, weed seeds, roots, tubers, rhizomes, insects, nematodes, and soil-inhabiting fungi on all food and non-food crops. It is also used as a pre-planting fumigant in seed beds, vine crops, fruit trees, row crops, flowers, and ornamentals. Metham sodium is considered environmentally friendly as it breaks down after two weeks into carbon dioxide, water, and small amounts of sodium and sulfur.
Used in Environmental Applications:
Metham sodium is used as an environmentally-friendly and sustainable electrocatalyst for oxygen reduction reactions, contributing to the development of clean energy technologies and reducing the environmental impact of industrial processes.
Air & Water Reactions
Slow reaction upon dilution produces toxic gases hydrogen sulfide and methylisothiocyanate. This reaction is accelerated by the addition of acid.
Reactivity Profile
METAM SODIUM is a dithiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Hazard
Irritant to tissue, toxic to plants and vege-
tation.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Flammability and Explosibility
Notclassified
Trade name
A7-VAPAM?; BASAMID-FLUID?;
BUSAN?; CHAP-FUME?; DISCOVERY?; HERBATIM
(dihydrate)?; KARBATION?; KARBATION (di-
hydrate)?; MAPOSOL?; MAPOSOL (dihydrate)?;
METACIDE?; METAM (dihydrate)?; METAM-FLUID
BASF?; METHAM DIHYDRATE (dihydrate)?;
MONAM (dihydrate)?; N-869?; N 869 (dihydrate)?;
NEMATIN?; SECTAGON?; SISTAN?; SMDC (di-
hydrate)?; SOLASAN 500?; SOLESAN 500?;
SOMETAM?; TRAPEX?; TRIMATON (dihydrate)?;
TRIMATRON?; UCETAM?; VAPAM?; VAPAM (di-
hydrate)?; VAPOROOTER (dihydrate)?; VDM?; VPM
(dihydrate)?; VPM? Fungicide; VPN?; WOODFUME
VAPAM?
Contact allergens
Metham-Na is a fungicide nematocide of the dithiocarbamate group. Sensitization occurs among agricultural workers.
Potential Exposure
A dithiocarbamate fungicide, nematicide, herbicide, soil fumigant, and algaecide A general soil
biocide that is used to control weeds, weed seeds, roots,
tubers, rhizomes, insects, nematodes and soil inhabiting
fungi on all food and nonfood crops. Also used as a preplanting fumigant in seed beds, vine crops, fruit trees, row
crops, flowers and ornamentals. Environmental friendly; it
breaks down after two weeks into carbon dioxide, water,
and sodium and sulfur in small amounts. A United States
Environmental Protection Agency Restricted Use Pesticide
(RUP).
Metabolic pathway
Metam-sodium is a water soluble propesticide that decomposes to generate
the highly volatile and fungitoxic methyl isothiocyanate. The pathways
of metabolism of methyl isothiocyanate are described under its own
entry.
Shipping
UN3267 Corrosive liquid, basic, organic, n.o.s.,
Hazard class: 8; Labels: 8-Corrosive material, Technical
Name Required. UN2771 Dithiocarbamate and
Thiocarbamate pesticides, solid, toxic, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials
Degradation
Metam-sodium can be stable in concentrated aqueous solution for several
weeks but is unstable when diluted. Decomposition is promoted by acids
and salts of heavy metals. DT50 values for hydrolysis of metam-sodium
were 23.8, 180 and 45.6 hours at pH 5, 7 and 9 (25 °C), respectively. It is
sensitive to light and solutions exposed to sunlight had a DT50 value of 1.6
hours (pH 7, 25 °C) (PM). In aqueous solution at high pH (9.5), metamsodium
was oxidatively degraded to form methyl isothiocyanate (2) and
elemental sulfur. At lower pH it was degraded non-oxidatively, affording
carbon disulfide, hydrogen sulfide, methy lamine, methyl isothiocyanate
(2) and N,N'-dimethylthiuram disulfide (3). It is noteworthy that methylamine
and carbon disulfide can react to yield methyl isothiocyanate (2)
that can in turn react with metam to produce N,N'-dimethylthiuram
disulfide (3). Methyl isothiocyanate (2) can react with methylamine
or hydrogen sulfide, giving dimethylthiourea (4) (Turner and Corden,
1963).
Incompatibilities
Slow reaction upon dilution in water
releasing toxic gases of hydrogen sulfide and methyl isothiocyanate. This reaction is accelerated by the addition of
acid. May liberate toxic gas when in contact with acids.
Combustible; vapors when heated or dust from dry material
may form explosive mixture in air. Dithiocarbamate esters
are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of Dithiocarbamate
compounds, including carbon disulfide, oxides of sulfur,
oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Thio and dithiocarbamates slowly decompose in
aqueous solution to form carbon disulfide and methylamine
or other amines. Such decompositions are accelerated by
acids. Flammable gases are generated by the combination
of dithiocarbamate with aldehydes, nitrides, and hydrides.
Dithiocarbamate are incompatible with acids, peroxides,
and acid halides. Corrosive to iron, copper brass and zinc
metals, especially in the presence of moisture. Heat alkalies
(lime), moisture can cause decomposition. Degradation produces ethylene thiourea.
Waste Disposal
Do not discharge into drains
or sewers. Dispose of waste material as hazardous waste
using a licensed disposal contractor to an approved landfill. 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. A potential candidate for liquid injection incineration at a temperature
range of 650 to 1600C and a residence time 0.1 to
2 seconds. Also, a potential candidate for rotary kiln
incineration at a temperature range of 820 to 1600C and
residence times of seconds for liquids and gases,
and hours for solids.
Check Digit Verification of cas no
The CAS Registry Mumber 137-42-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 7 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 137-42:
(5*1)+(4*3)+(3*7)+(2*4)+(1*2)=48
48 % 10 = 8
So 137-42-8 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO2S2.Na/c1-6-7-3-2(4)5;/h3H,1H3,(H,4,5);/q;+1/p-1
137-42-8Relevant articles and documents
4-Aryl-2-Imino-1,3-Dithiolanes from the Room Temperature Coupling of Sodium Dithiocarbamates with Sulfonium Salts
Bresciani, Giulio,Marchetti, Fabio,Ciancaleoni, Gianluca,Pampaloni, Guido
, p. 1615 - 1622 (2021)
A series of 4-aryl-2-imino-1,3-dithiolanes was synthesized by means of a straightforward strategy starting from readily available precursors: reactions of dithiocarbamates and arylsulfonium salts, at room temperature in water/CH2Cl2 as biphasic medium, afforded the five-membered cyclic products in good yields. The reaction mechanism was investigated by DFT calculations.
Method for synthesizing metham in one step
-
Paragraph 0018-0020; 0022; 0024, (2020/11/12)
The invention discloses a method for synthesizing a soil fumigant metham in one step. The method comprises the following steps: stirring and mixing water, a monomethylamine aqueous solution and a sodium hydroxide aqueous solution, dropwise adding carbon disulfide, continuously stirring and reacting to obtain a finished product of metham with the appearance of yellow to red brown, wherein the finished product is used for treating soil fumigation and disinfection and killing root-knot nematodes, harmful bacteria and soil insects and removing weeds. The whole synthesis method has the advantages of high production efficiency, high product content, high operation safety, good storage stability and environmental friendliness.
Dithiolane-Isocyanate Imminium Methylides: A Rapid Stereoselective Entry into γ-Lactams
Fishwick, Colin W. G.,Foster, Richard J.,Carr, Robin E.
, p. 9409 - 9412 (2007/10/02)
Methods have been developed for the generation and trapping of dithiolane-isocyanate imminium methylides which are a new type of azomethine methylide-derived 1,3-dipole.These species add efficiently and stereoselectively to electron deficient olefins yielding novel dithiolane-protected γ-lactams which can be efficiently deprotected to yield the corresponding lactam systems.
Characterization of protein adducts produced by N-methyldithiocarbamate and N-methyldithiocarbamate esters
Valentine,Amarnath,Amarnath,Graham
, p. 254 - 261 (2007/10/03)
The toxicity of N-methyldithiocarbamate may be mediated through decomposition to more biologically active compounds. Two principal products, CS2 and methyl isothiocyanate, have the potential to interact covalently with macromolecules in biological systems. In this investigation the ability of N-methyldithiocarbamate to generate methyl isothiocyanate and CS2 under physiological conditions resulting in acylation and covalent cross-linking of proteins was examined using 13C NMR and GC/MS. Two N-methyldithiocarbamate esters, S-methyl N-methyldithiocarbamate and (N-acetyl-S- methylthiocarbamoyl)cysteine, were also investigated to evaluate the acylating ability of sulfhydryl conjugates of N-methyldithiocarbamate. The predominant and most stable adduct produced by the free dithiocarbamate and its S-substituted esters was methylthiourea on ε-lysyl and N-terminal α- amino groups. Derivatization on N-terminal amino groups progressed more rapidly for the dithiocarbamate than for its mercapturate. Methylurea protein adducts were also produced by the dithiocarbamate and its esters, suggesting production of methyl isocyanate in the decomposition of N- methyldithiocarbamate. Covalent cross-linking of β-lactoglobulin by N- methyldithiocarbamate resulting from its decomposition to CS2 was observed using denaturing polyacrylamide gel electrophoresis. These results demonstrate the ability of a monoalkyldithiocarbamate to acylate protein amino groups and effect covalent cross-linking. These processes represent molecular mechanisms that may contribute to the toxicity of this class of compounds.
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