Metam sodium
Names | |
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Preferred IUPAC name Sodium methylcarbamodithioate | |
Other names Metham sodium Carbathion Carbathione Carbothion Metamsodium Metam-sodium | |
Identifiers | |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.004.812 |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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). Y verify (what is YN ?) Infobox references |
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]
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
- Zineb - A related dithiocarbamate salt which is also used as a fungicide
References
- ^ a b Merck Index, 11th Edition, 5860.
- ^ a b Hartwig, Jürgen; Sommer, Herbert; Müller, Franz (2008). "Nematicides". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_125.pub2. ISBN 978-3527306732.
- ^ 2000-2001 Pesticide Market Estimates Archived 2009-02-07 at the Wayback Machine, U.S. Environmental Protection Agency
- ^ Review of Metam Sodium, Dazomet, Methylisothiocyanate (MITC) Archived 2009-07-13 at the Wayback Machine, Australian Pesticides and Veterinary Medicines Authority, June 1997
- ^ "Largest chemical spill in California history". dtsc.ca.gov. Retrieved 2017-12-11.
External links
- Metam sodium in the Pesticide Properties DataBase (PPDB)
- v
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Triazolinones |
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- dithiopyr
- fluroxypyr
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Photosystem II inhibitors |
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Photosystem II inhibitors |
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ALS inhibitors |
- 3-AT
- aclonifen
- aminocyclopyrachlor
- Bentazon
- bromoxynil
- clomazone
- DCBN
- dinoseb
- indaziflam
- juglone
- methazole
- metam sodium
- metamitron
- metribuzin
- pyribenzoxim
- Ziram