Metam sodium

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Metam sodium [1]
Metham sodium.png
Metham sodium 3D ball.png
Names
Preferred IUPAC name
Sodium methylcarbamodithioate
Other names
Metham sodium
Carbathion
Carbathione
Carbothion
Metamsodium
Metam-sodium
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.812 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C2H5NS2.Na/c1-3-2(4)5;/h1H3,(H2,3,4,5);/q;+1/p-1 Yes check.svgY
    Key: AFCCDDWKHLHPDF-UHFFFAOYSA-M Yes check.svgY
  • [Na+].[S-]C(=S)NC
Properties
C2H4NNaS2
Molar mass 129.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Metam sodium is an organosulfur compound with the formula CH3NHCS2Na. The compound is a sodium salt of a dithiocarbamate. The compound exists as a colorless dihydrate, but most commonly it is encountered as an aqueous solution. [2] It is used as a soil fumigant, pesticide, herbicide, and fungicide. It is one of the most widely used pesticides in the United States, with approximately 60 million pounds used in 2001. [3]

Contents

Preparation and properties

Metam sodium is prepared by combining methylamine, carbon disulfide, and sodium hydroxide: [2]

CH3NH2 + CS2 + NaOH → CH3NHCS2Na + H2O

It also arises from the reaction of methyl isothiocyanate and sodium thiolate. [1]

Upon exposure to the environment, metam sodium decomposes to methyl isothiocyanate. [4]

Safety and environmental considerations

Metam sodium is nonpersistent in the environment since it is prone to hydrolysis. The degradation products, carbon disulfide and methyl amine are however toxic. In 1991 a tank car with 19,000 gallons of metam sodium spilled into Sacramento River above Lake Shasta. This killed all fish in a 41-mile stretch of the river. By 20 years later the rainbow trout population had recovered. [5]

See also

Related Research Articles

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s.

<span class="mw-page-title-main">Carbon disulfide</span> Neurotoxic compound with formula S=C=S

Carbon disulfide is a neurotoxic, colorless, volatile liquid with the formula CS2 and structure S=C=S. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent. It has an "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities. It is of comparable toxicity to carbon monoxide.

<span class="mw-page-title-main">Methanethiol</span> Chemical compound

Methanethiol is an organosulfur compound with the chemical formula CH
3
SH
. It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals, as well as in plant tissues. It also occurs naturally in certain foods, such as some nuts and cheese. It is one of the chemical compounds responsible for bad breath and the smell of flatus. Methanethiol is the simplest thiol and is sometimes abbreviated as MeSH. It is very flammable.

<span class="mw-page-title-main">Isothiocyanate</span> Chemical group (–N=C=S)

In organic chemistry, isothiocyanate is the functional group −N=C=S, formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also known as mustard oils. An artificial isothiocyanate, phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

Xanthate usually refers to a salt with the formula ROCS
2
M+
(R = alkyl; M+ = Na+, K+), thus they are the metal-thioate/O-esters of dithiocarbonate. The name xanthates is derived from Ancient Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and (in mining) for extraction of certain ores. They are also versatile intermediates in organic synthesis. Xanthate can also refer to the O,S-ester of xanthic acid. These esters have the structure ROC(=S)SR′.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

<span class="mw-page-title-main">Methyl isothiocyanate</span> Chemical compound

Methyl isothiocyanate is the organosulfur 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 isothiocyanate in industry.

<span class="mw-page-title-main">Sodium diethyldithiocarbamate</span> Chemical compound

Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2. It is a pale yellow, water soluble salt.

<span class="mw-page-title-main">Dithiocarbamate</span> Chemical group (>N–C(=S)–S–)

In organic chemistry, a dithiocarbamate is a functional group with the general formula R2NC(S)SR and structure >N−C(=S)−S−. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms.

<span class="mw-page-title-main">Thiuram disulfide</span>

Thiuram disulfides are a class of organosulfur compounds with the formula (R2NCSS)2. Many examples are known, but popular ones include R = Me and Et. They are disulfides obtained by oxidation of the dithiocarbamates. These compounds are used in sulfur vulcanization of rubber as well as pesticides and drugs. They are typically white or pale yellow solids that are soluble in organic solvents.

<span class="mw-page-title-main">Phenyl isothiocyanate</span> Chemical compound

Phenyl isothiocyanate (PITC) is a reagent used in reversed phase HPLC. PITC is less sensitive than o-phthaldehyde (OPA) and cannot be fully automated. PITC can be used for analysing secondary amines, unlike OPA. It is also known as Edman's reagent and is used in Edman degradation.

Zineb is the chemical compound with the formula {Zn[S2CN(H)CH2CH2N(H)CS2]}n. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide.

This is an index of articles relating to pesticides.

<span class="mw-page-title-main">Maneb</span> Chemical compound

Maneb is a fungicide and a polymeric complex of manganese with the ethylene bis(dithiocarbamate) anionic ligand.

<span class="mw-page-title-main">Ethylene thiourea</span> Chemical compound

Ethylene thiourea (ETU) is an organosulfur compound with the formula C3H6N2S. It is an example of an N,N-disubstituted thiourea. It is a white solid. It is synthesized by treating ethylenediamine with carbon disulfide.

In chemistry, a thioxanthate is an organosulfur compound with the formula RSCS2X. When X is an alkali metal, the thioxanthate is a salt. When X is a transition metal, the thioxanthate is a ligand, and when X is an organic group, the compounds are called thioxanthate esters. They are usually yellow colored compounds that often dissolve in organic solvents. They are used as precursors to some catalysts, froth flotation agents, and additives for lubricants.

<span class="mw-page-title-main">Methyl dimethyldithiocarbamate</span> Chemical compound

Methyl dimethyldithiocarbamate is the organosulfur compound with the formula (CH3)2NC(S)SCH3. It is the one of simplest dithiocarbamic esters. It is a white volatile solid that is poorly soluble in water but soluble in many organic solvents. It was once used as a pesticide.

<span class="mw-page-title-main">Transition metal dithiocarbamate complexes</span>

Transition metal dithiocarbamate complexes are coordination complexes containing one or more dithiocarbamate ligand, which are typically abbreviated R2dtc. Many complexes are known. Several homoleptic derivatives have the formula M(R2dtc)n where n = 2 and 3.

References

  1. 1 2 Merck Index , 11th Edition, 5860.
  2. 1 2 Hartwig, Jürgen; Sommer, Herbert; Müller, Franz (2008). "Nematicides". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_125.pub2. ISBN   978-3527306732.
  3. 2000-2001 Pesticide Market Estimates Archived 2009-02-07 at the Wayback Machine , U.S. Environmental Protection Agency
  4. Review of Metam Sodium, Dazomet, Methylisothiocyanate (MITC), Australian Pesticides and Veterinary Medicines Authority, June 1997
  5. "Largest chemical spill in California history". dtsc.ca.gov. Retrieved 2017-12-11.