Zineb

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Zineb
ZinebWNormalBonding.png
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 Edit this at Wikidata
EC Number
  • 235-180-1
KEGG
RTECS number
  • ZH3325000
UNII
  • 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
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R-phrases (outdated) R37 R43
S-phrases (outdated) (S2) S8 S24/25 S46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).
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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.[1]


Production and applications[edit]

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[edit]

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]

See also[edit]

References[edit]

  1. ^ a b c 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.CS1 maint: uses authors parameter (link)
  2. ^ a b Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2[page needed]
  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. ISBN 978-1-4615-8506-0.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

External links[edit]

  • Zineb in the Pesticide Properties DataBase (PPDB)