Zineb

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Zineb
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Names
IUPAC name
zinc ethane-1,2-diylbis(dithiocarbamate)
Other names
[[1,2 ethanediylbis[dithiocarbamodithioato](2−)]] zinc,
Dithane Z-78, Aphytora, Amitan
Identifiers
12122-67-7 YesY
ChEBI CHEBI:52498 N
ChemSpider 2297309 N
EC Number 235-180-1
Jmol 3D model Interactive image
KEGG C15232 YesY
PubChem 3032296
RTECS number ZH3325000
  • 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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. 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.[1] 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.[1] It continues to be used in many other countries.

Structure

Zineb is a polymeric complex of zinc with the bis(dithiocarbamate) derived from the reaction.[2] The polymer is composed of Zn(dithiocarbamate)2 subunits linked by ethylene 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

References

  1. ↑ 1.0 1.1 Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2[page needed]
  2. ↑ 2.0 2.1 Ullmann's Agrochemicals, Wiley-VCH Staff , Wiley-Vch (COR), 2007 ISBN 3-527-31604-3[page needed]
  3. ↑ Genchev, M.; Davarski, K. "Structure of some metal complexes of ethylenediaminebis(dithiocarbamate) used as active fungicides" Burgas 1978, 13, Pt. 1, 39-44.
  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

  • Zineb in the Pesticide Properties DataBase (PPDB)
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