Zineb

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]

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:52498
ChemSpider	2297309
ECHA InfoCard	100.031.970
EC Number	235-180-1
KEGG	C15232
PubChem CID	3032296
RTECS number	ZH3325000
UNII	X1FSB1OZPT
CompTox Dashboard (EPA)	DTXSID5021465
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EU classification (DSD) (outdated)	Irritants (Xi) Sensitizers
R-phrases (outdated)	R37 R43
S-phrases (outdated)	(S2) S8 S24/25 S46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).
verify (what is  ?)
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]

See also

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

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. ISBN 978-3527306732.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. 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

• Zineb in the Pesticide Properties DataBase (PPDB)