Zineb
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| IUPACName = zinc ethane-1,2-diylbis(dithiocarbamate)
| OtherNames = [[1,2 ethanediylbis[dithiocarbamodithioato](2−)]] zinc,
Dithane Z-78, Aphytora, Amitan
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|- | ECHA InfoCard | 100.031.970 |- | EC Number | 235-180-1 |- | KEGG
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|- | RTECS number | ZH3325000 |-
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- 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-2Key: AMHNZOICSMBGDH-NUQVWONBAD
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- [Zn+2].[S-]C(=S)NCCNC(=S)[S-]
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| C4H6N2S4Zn |- | Molar mass | 275.8 g/mol (monomer) |- | Appearance | pale yellow powder |- |Section3=!Hazards |-
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| R-phrases (outdated)
| R37 R43
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| (S2) S8 S24/25 S46
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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
- Metam sodium - A related dithiocarbamate salt which is also used as a fungicide
- Maneb - ethylene bis(dithiocarbamate) with manganese instead of zinc
References
- 1 2 3 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.
- 1 2 Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2
- ↑ 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.
- ↑ 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)