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'''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]]. This pale yellow solid is used as [[fungicide]].
'''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]]. This pale yellow solid is used as [[fungicide]].<ref name=Ullmann>{{cite encyclopedia|authors=Franz Müller, Peter Ackermann, 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}}</ref>


==Production and applications==
==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>
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 [[mildew]]s, [[rust (botany)|rusts]] and redfire disease.<ref name = "Ullmans"/> In the US it was once registered as a "General Use Pesticide", however all registrations were voluntarily cancelled following an [[United States Environmental Protection Agency|EPA]] special review.<ref name = "Kamrin"/> It continues to be used in many other countries.
Its uses include control of downy [[mildew]]s, [[rust (botany)|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 [[United States Environmental Protection Agency|EPA]] special review.<ref name = "Kamrin"/> It continues to be used in many other countries.


==Structure==
==Structure==
Zineb is a polymeric [[complex (chemistry)|complex]] of [[zinc]] with the [[dithiocarbamate|bis(dithiocarbamate)]] derived from the reaction.<ref name = "Ullmans">Ullmann's Agrochemicals, Wiley-VCH Staff, Wiley-Vch (COR), 2007 {{ISBN|3-527-31604-3}}{{page needed|date=March 2015}}</ref> The polymer is composed of Zn(dithiocarbamate)<sub>2</sub> subunits linked by ethylene backbone.<ref>Genchev, M.; Davarski, K. "Structure of some metal complexes of ethylenediaminebis(dithiocarbamate) used as active fungicides" Burgas 1978, 13, Pt. 1, 39-44.</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 [[bridging ligand|bridged]] by one sulfur center.<ref>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}}</ref>
Zineb is a polymeric [[complex (chemistry)|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|book=Residue Reviews|pages=45-6|title=Residues of dithiocarbamate fungicides and their metabolites on plant foods
|authors=R. Engst, W. Schnaak|year=1974|editor=Gunther F.A.|volume=52|publisher=Springer|place=New York, NY|doi=10.1007/978-1-4615-8504-6_3}}</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 [[bridging ligand|bridged]] by one sulfur center.<ref>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}}</ref>


==See also==
==See also==

Revision as of 18:11, 3 March 2018

Zineb
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 (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.031.970 Edit this at Wikidata
EC Number
  • 235-180-1
KEGG
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[1]

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

References

  1. ^ a b c "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2012. doi:10.1002/14356007.o12_o06. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)
  2. ^ a b Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2[page needed]
  3. ^ Gunther F.A., ed. (1974). Residues of dithiocarbamate fungicides and their metabolites on plant foods. Vol. 52. New York, NY: Springer. pp. 45–6. doi:10.1007/978-1-4615-8504-6_3. {{cite book}}: Cite uses deprecated parameter |authors= (help); Unknown parameter |book= ignored (help)
  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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