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 (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.031.970
EC Number 235-180-1
KEGG
RTECS number ZH3325000
Properties
C4H6N2S4Zn
Molar mass 275.8 g/mol (monomer)
Appearance pale yellow powder
Hazards
Irritants (Xi)
Sensitizers
R-phrases R37 R43
S-phrases (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. This pale yellow solid is used as fungicide.

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.[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[edit]

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[edit]

References[edit]

  1. ^ a b Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2[page needed]
  2. ^ a b 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[edit]

  • Zineb in the Pesticide Properties DataBase (PPDB)