Zinc bis(dimethyldithiocarbamate)

Source: Wikipedia, the free encyclopedia.
Ziram
Chemical structure of Ziram
Names
IUPAC name
(μ-Dimethylcarbamodithioato-1κS,2κS′)(μ-dimethylcarbamodithioato-1κS′,2κS)bis[(dimethylcarbamodithioato-κ2S,S′)zinc]
Other names
zinc dimethyldithiocarbamate, Ziram
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.004.808 Edit this at Wikidata
UNII
  • InChI=1S/2C3H7NS2.Zn/c2*1-4(2)3(5)6;/h2*1-2H3,(H,5,6);/q;;+2/p-2
    Key: DUBNHZYBDBBJHD-UHFFFAOYSA-L
  • CN(C)C(=S)[S-].CN(C)C(=S)[S-].[Zn+2]
Properties
C6H12N2S4Zn
Molar mass 305.80 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zinc dimethyldithiocarbamate is a coordination complex of zinc with dimethyldithiocarbamate. It is a pale yellow solid that is used as a fungicide, the sulfur vulcanization of rubber, and other industrial applications.[1]

Applications

Known as ziram in agriculture, it was introduced in the United States in 1960 as a broad-spectrum fungicide. It was used to address

nectarines, pears, and table and raisin grapes.[3]

Alternatively, ziram is used as an additive ingredient in industrial

caulking, and paint. It also serves as a bird and mammal repellent
on outdoor ornamental items.

Chemistry

The compound is a prototypical zinc dithiocarbamate, a broad class of coordination complexes with the formulae Zn(R2NCS2)2, where R can be varied. Such compounds are produced by treating zinc and dithiocarbamate (R2NCS2−), as illustrated with dimethyldithiocarbamate:[4]

2 (CH3)2NCS2− + Zn2+ → Zn((CH3)2NCS2)2

Annually, approximately 1.9 million pounds of the active ziram ingredient are used. Ziram is often sold in powder or granule form.[2]

Zinc bis(diethyldithiocarbamate) complexes degrade thermally to give zinc sulfide.[5]

Structure

Compounds of the type Zn(S2CNR2)2 are dimeric, i.e. their proper formula is [Zn(S2CNR2)2]2.[6] Each Zn center is in a distorted pentacoordinate site, with four Zn-S bonds of 2.3 Å length and one Zn---S interaction >2.8 Å in length. Mono-zinc derivatives are obtained by adding strong ligands (L) such as amines, which give adducts Zn(S2CNR2)2L.[7]

Ecological effects

The U.S.

amphibians
places it in the "highly toxic" category.

See also

Structure of the ethyl-methyl carbamate derivative [Zn(S2CNEtMe)2]2.[6]

References

  1. ISBN 978-3527306732
    .
  2. ^ a b "Ziram" (PDF). EPA R.E.D Facts. United States Environmental Protection Agency. Retrieved April 26, 2015.
  3. ^ "Ziram". Extension Toxicology Network Pesticide Information Profiles. Cornell University, Oregon State University, the University of Idaho, and the University of California at Davis and the Institute for Environmental Toxicology, Michigan State University. Retrieved April 26, 2015.
  4. ISBN 3527306730
    .
  5. ISSN 1466-8033
    .
  6. ^
    doi:10.1016/0277-5387(95)00559-5
    .
  7. doi:10.1021/ic00345a020
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Zinc_bis(dimethyldithiocarbamate)&oldid=1157382072"