{{For|the French journalist|Zineb El Rhazoui}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 431571449 | ImageFile1 = ZinebWNormalBonding.png | ImageSize1 = 360px | IUPACName = zinc ethane-1,2-diylbis(dithiocarbamate) | OtherNames = 1,2 ethanediylbis[dithiocarbamodithioato](2−) zinc,<br />Dithane Z-78, Aphytora, Amitan |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 12122-67-7 | Beilstein = 4165797 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C15232 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 52498 | PubChem = 3032296 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2297309 | EINECS = 235-180-1 | RTECS = ZH3325000 | UNNumber = 2771 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = X1FSB1OZPT | 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 | InChIKey = AMHNZOICSMBGDH-NUQVWONBAD | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = AMHNZOICSMBGDH-UHFFFAOYSA-L | SMILES = [Zn+2].[S-]C(=S)NCCNC(=S)[S-] }} |Section2={{Chembox Properties | C=4 | H=6 | N=2 | S=4 | Zn=1 | MolarMass = 275.8 g/mol (monomer) | Appearance = pale yellow powder | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards =skin sensitizer | Hazards_ref=<ref>{{cite web |title=Zinc, [<nowiki/>[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-kappaS,kappaS']- |url=https://pubchem.ncbi.nlm.nih.gov/compound/3032296#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> | GHSPictograms = {{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|317|335}} | PPhrases = {{P-phrases|261|271|280|302+352|304+340|312|333+313|363|403+233|405|501}} | FlashPt = | AutoignitionPt = }} }} '''Zineb''' is the chemical compound with the formula {Zn[S<sub>2</sub>CN(H)CH<sub>2</sub>CH<sub>2</sub>N(H)CS<sub>2</sub>]}<sub>n</sub>. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide.<ref name=Ullmann>{{cite encyclopedia|author1=Franz Müller |author2=Peter Ackermann |author3=Paul Margot |title=Fungicides, Agricultural, 2. Individual Fungicides|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry |publisher=Wiley-VCH |place=Weinheim |year=2012|doi=10.1002/14356007.o12_o06|isbn=978-3527306732}}</ref>
==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.<ref name = "Kamrin">Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, {{ISBN|1-56670-190-2}}{{page needed|date=March 2015}}</ref> Its uses include control of downy mildews, rusts, and redfire disease.<ref name = "Ullmann"/> In the US it was once registered as a "General Use Pesticide", however all registrations were voluntarily cancelled following an EPA special review.<ref name = "Kamrin"/> It continues to be used in many countries, including the United States.
==Structure== Zineb is a polymeric complex of zinc with a dithiocarbamate.<ref name=Ullmann/> The polymer is composed of Zn(dithiocarbamate)<sub>2</sub> subunits linked by an ethylene (-CH<sub>2</sub>CH<sub>2</sub>-) backbone.<ref>{{cite book |pages=45–46 |author1=R. Engst |author2=W. Schnaak |title=Residue Reviews |chapter=Residues of dithiocarbamate fungicides and their metabolites on plant foods |year=1974 |editor=Gunther F.A. |volume=52 |publisher=Springer |place=New York, NY |doi=10.1007/978-1-4615-8504-6_3 |isbn=978-1-4615-8506-0}}</ref> A reference compound is [Zn(S<sub>2</sub>CNEt<sub>2</sub>)<sub>2</sub>]<sub>2</sub>, which features a pair of tetrahedral Zn centers bridged by one sulfur center.<ref>{{cite journal |author1=Bonamico, M. |author2=Mazzone, G. |author3=Vaciago, A. |author4=Zambonelli, L. |date=1965 |title=Structural studies of metal dithiocarbamates. III. The Crystal and Molecular Structure of Zinc Diethyldithiocarbamate |journal=Acta Crystallogr |volume=19 |issue=6 |pages=898–909 |doi=10.1107/S0365110X65004620 |bibcode=1965AcCry..19..898B }}</ref>
==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== {{reflist}}
==External links== *{{PPDB|683}}
Category:Fungicides Category:Endocrine disruptors Category:Zinc compounds Category:Dithiocarbamates Category:Polymers