Zineb

Zineb is the chemical compound with the formula {Zn[S2CN(H)CH2CH2N(H)CS2]}n. Structurally, it is classified as a coordination polymer. This pale yellow solid is used as fungicide.[1]

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)
ChEBI
ChemSpider
ECHA InfoCard 100.031.970
EC Number
  • 235-180-1
KEGG
RTECS number
  • ZH3325000
UNII
Properties
C4H6N2S4Zn
Molar mass 275.8 g/mol (monomer)
Appearance pale yellow powder
Hazards
Irritants (Xi)
Sensitizers
R-phrases (outdated) R37 R43
S-phrases (outdated) (S2) S8 S24/25 S46
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references


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.[2] Its uses include control of downy mildews, rusts, and redfire disease.[1] In the US it was once registered as a "General Use Pesticide", however all registrations were voluntarily cancelled following an EPA special review.[2] It continues to be used in many other countries.

Structure

Zineb is a polymeric complex of zinc with a dithiocarbamate.[1] The polymer is composed of Zn(dithiocarbamate)2 subunits linked by an ethylene (-CH2CH2-) backbone.[3] A reference compound is [Zn(S2CNEt2)2]2, which features a pair of tetrahedral Zn centers bridged by one sulfur center.[4]

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See also

References
  1. 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.CS1 maint: uses authors parameter (link)
  2. Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2
  3. R. Engst, W. Schnaak (1974). Gunther F.A. (ed.). "Residues of dithiocarbamate fungicides and their metabolites on plant foods". Residue Reviews. New York, NY: Springer. 52: 45–6. doi:10.1007/978-1-4615-8504-6_3.CS1 maint: uses authors parameter (link)
  4. Bonamico, M.; Mazzone, G.; Vaciago, A.; Zambonelli, L., "Structural studies of metal dithiocarbamates. III. The Crystal and Molecular Structure of Zinc Diethyldithiocarbamate", Acta Crystallogr. 1965, volume 19, pp. 898-909. doi:10.1107/S0365110X65004620
  • Zineb in the Pesticide Properties DataBase (PPDB)
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