Zineb
Names
IUPAC name
zinc ethane-1,2-diylbis(dithiocarbamate)
Other names
1,2 ethanediylbis[dithiocarbamodithioato](2−) zinc,
Dithane Z-78, Aphytora, Amitan
Identifiers
3D model (JSmol)
4165797
ChEBI
ChemSpider
ECHA InfoCard 100.031.970
EC Number
  • 235-180-1
KEGG
RTECS number
  • ZH3325000
UNII
UN number 2771
  • 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-2 ☒N
    Key: AMHNZOICSMBGDH-UHFFFAOYSA-L ☒N
  • 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-2
    Key: AMHNZOICSMBGDH-NUQVWONBAD
  • [Zn+2].[S-]C(=S)NCCNC(=S)[S-]
Properties
C4H6N2S4Zn
Molar mass 275.8 g/mol (monomer)
Appearance pale yellow powder
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
 skin sensitizer
GHS labelling:
GHS07: Exclamation mark
Warning
H317, H335
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 [77 °F], 100 kPa).
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Infobox references

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.[2]

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.[3] Its uses include control of downy mildews, rusts, and redfire disease.[2] In the US it was once registered as a "General Use Pesticide", however all registrations were voluntarily cancelled following an EPA special review.[3] It continues to be used in many other countries.

Structure

Zineb is a polymeric complex of zinc with a dithiocarbamate.[2] The polymer is composed of Zn(dithiocarbamate)2 subunits linked by an ethylene (-CH2CH2-) backbone.[4] A reference compound is [Zn(S2CNEt2)2]2, which features a pair of tetrahedral Zn centers bridged by one sulfur center.[5]

See also

References

  1. ↑ "Zinc, [[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-kappaS,kappaS']-". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 3 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. 1 2 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.
  • Zineb in the Pesticide Properties DataBase (PPDB)
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