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Zineb

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Zineb
Names
IUPAC name zinc ethane-1,2-diylbis(dithiocarbamate)
Other names 1,2 ethanediylbis(2−) zinc,
Dithane Z-78, Aphytora, Amitan
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 4165797
ChEBI
ChemSpider
ECHA InfoCard 100.031.970 Edit this at Wikidata
EC Number
  • 235-180-1
KEGG
PubChem CID
RTECS number
  • ZH3325000
UNII
UN number 2771
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8N2S4.Zn/c7-3(8)5-1-2-6-4(9)10;/h1-2H2,(H2,5,7,8)(H2,6,9,10);/q;+2/p-2Key: AMHNZOICSMBGDH-UHFFFAOYSA-L
  • InChI=1/C4H8N2S4.Zn/c7-3(8)5-1-2-6-4(9)10;/h1-2H2,(H2,5,7,8)(H2,6,9,10);/q;+2/p-2Key: AMHNZOICSMBGDH-NUQVWONBAD
SMILES
  • .C(=S)NCCNC(=S)
Properties
Chemical formula C4H6N2S4Zn
Molar mass 275.8 g/mol (monomer)
Appearance pale yellow powder
Hazards
Occupational safety and health (OHS/OSH):
Main hazards skin sensitizer
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H317, H335
Precautionary statements P261, P271, P280, P302+P352, P304+P340, P312, P333+P313, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Zineb is the chemical compound with the formula {Zn}n. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide.

Production and applications

It is produced by treating ethylene bis(dithiocarbamate) sodium salt, "nabam", with zinc sulfate. This procedure can be carried out by mixing nabam and zinc sulfate in a spray tank. Its uses include control of downy mildews, rusts, and redfire disease. In the US it was once registered as a "General Use Pesticide", however all registrations were voluntarily cancelled following an EPA special review. It continues to be used in many other countries.

Structure

Zineb is a polymeric complex of zinc with a dithiocarbamate. The polymer is composed of Zn(dithiocarbamate)2 subunits linked by an ethylene (-CH2CH2-) backbone. A reference compound is 2, which features a pair of tetrahedral Zn centers bridged by one sulfur center.

See also

References

  1. "Zinc, [[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-kappaS,kappaS']-". pubchem.ncbi.nlm.nih.gov.
  2. ^ Franz Müller; Peter Ackermann; Paul Margot (2012). "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o12_o06. ISBN 978-3527306732.
  3. ^ Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2
  4. R. Engst; W. Schnaak (1974). "Residues of dithiocarbamate fungicides and their metabolites on plant foods". In Gunther F.A. (ed.). Residue Reviews. Vol. 52. New York, NY: Springer. pp. 45–46. doi:10.1007/978-1-4615-8504-6_3. ISBN 978-1-4615-8506-0.
  5. Bonamico, M.; Mazzone, G.; Vaciago, A.; Zambonelli, L. (1965). "Structural studies of metal dithiocarbamates. III. The Crystal and Molecular Structure of Zinc Diethyldithiocarbamate". Acta Crystallogr. 19 (6): 898–909. doi:10.1107/S0365110X65004620.

External links

  • Zineb in the Pesticide Properties DataBase (PPDB)
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