Zineb
 | |
| Names | |
|---|---|
| IUPAC name
zinc ethane-1,2-diylbis(dithiocarbamate) | |
| Other names
[[1,2 ethanediylbis[dithiocarbamodithioato](2−)]] zinc, Dithane Z-78, Aphytora, Amitan | |
| Identifiers | |
12122-67-7  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:52498  |
| ChemSpider | 2297309 |
| ECHA InfoCard | 100.031.970 |
| EC Number | 235-180-1 |
| KEGG | C15232 |
| PubChem | 3032296 |
| RTECS number | ZH3325000 |
| |
| |
| Properties | |
| 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). | |
| verify (what is ?) | |
| 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 2 Michael A. Kamrin, (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate, CRC Press, ISBN 1-56670-190-2
- 1 2 Ullmann's Agrochemicals, Wiley-VCH Staff , Wiley-Vch (COR), 2007 ISBN 3-527-31604-3
- ↑ Genchev, M.; Davarski, K. "Structure of some metal complexes of ethylenediaminebis(dithiocarbamate) used as active fungicides" Burgas 1978, 13, Pt. 1, 39-44.
- ↑ 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)