Zineb

Zineb

Names
IUPAC name zinc ethane-1,2-diylbis(dithiocarbamate)
Other names [[1,2 ethanediylbis[dithiocarbamodithioato](2−)]] zinc, Dithane Z-78, Aphytora, Amitan
Identifiers
CAS Number	12122-67-7
ChEBI	CHEBI:52498
ChemSpider	2297309
EC Number	235-180-1
Jmol 3D model	Interactive image
KEGG	C15232
PubChem	3032296
RTECS number	ZH3325000
InChI 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 Key: AMHNZOICSMBGDH-UHFFFAOYSA-L 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
SMILES [Zn+2].[S-]C(=S)NCCNC(=S)[S-]
Properties
Chemical formula	C4H6N2S4Zn
Molar mass	275.8 g/mol (monomer)
Appearance	pale yellow powder
Hazards
EU classification (DSD)	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

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

• Metam sodium - A related dithiocarbamate salt which is also used as a fungicide
• Maneb - ethylene bis(dithiocarbamate) with manganese instead of zinc

References

1. Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2
2. Ullmann's Agrochemicals, Wiley-VCH Staff , Wiley-Vch (COR), 2007 ISBN 3-527-31604-3
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)