Maneb

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 434399765 | ImageFile = Maneb.svg | ImageAlt = | IUPACName = [[2-[(Dithiocarboxy)amino]ethyl]carbamodithioato]](2-)-kS,kS']manganese | OtherNames = Manganese ethylene-1,2-bisdithiocarbamate, polymer |Section1=!Identifiers

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CAS Number

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• 12427-38-2  ^Y

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3D model (JSmol)

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• Interactive image

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| ChemSpider

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• 2297517  ^N

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| ECHA InfoCard | 100.032.400 |-

| MeSH | Maneb |-

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PubChem CID

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• 3032581

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| UNII

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• K221E12G7T  ^Y

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CompTox Dashboard (EPA)

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• DTXSID9020794

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InChI

• InChI=1S/C4H8N2S4.Mn/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: YKSNLCVSTHTHJA-UHFFFAOYSA-L

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SMILES

• [Mn+]SC(=S)NCCNC(=S)S[Mn]SC(=S)NCCNC(=S)S[Mn]SC(=S)NCCNC(=S)S[Mn]SC(=S)NCCNC(=S)S[Mn]SC(=S)NCCNC(=S)[S-]

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Chemical formula

| (C₄H₆MnN₂S₄)_n

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| Appearance | Yellow to brown colored crystalline solid |-

| Density | 1.92 g/cm³ |- | Melting point | 192 to 204 °C (378 to 399 °F; 465 to 477 K) (decomposes)

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Solubility in water

| 160 mg/L |- |Section3=!Hazards

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| GHS labelling: |-

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Pictograms

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Maneb (manganese ethylene-bis-dithiocarbamate) is a fungicide and a polymeric complex of manganese with the ethylene bis (dithiocarbamate) anionic ligand. ^[1]

Health effects

See also: Manganism, Parkinsonism, and Parkinson's disease

Exposure to maneb can occur when breathed in; it can irritate the eyes, nose, and throat as well as cause headache, fatigue, nervousness, dizziness, seizures and even unconsciousness. Prolonged or long-term exposure may interfere with the function of the thyroid. Exposure to maneb is also shown to induce a Parkinson's disease like neurotoxicity in mice. ^[2] It is still challenged whether maneb, along with Paraquat, is an environmental risk factor for Parkinson's disease. ^{[3] [4]}

Production

Manganese(II) ethylenebis(dithiocarbamate) of low ethylenethiourea (ETU) content is prepared by mixing disodium ethylenebis (dithiocarbamate) with formaldehyde in aqueous medium then mixing a water-soluble manganese(II) salt to precipitate the maneb. The product can be further formulated with a metal salt and also with paraformaldehyde. (See External links for the patent citation)

Applications

Maneb, is a broad spectrum fungicide that is extensively applied against a wide range of fungal pathogens affecting ornamental plants, food and feed crops. It can also be used to create a toxin-based animal model of Parkinson's disease, usually in primates. ^{[5] [6]}

Regulation

Maneb was included in a pesticide ban proposed by the Swedish Chemicals Agency ^[7] and approved by the European Parliament on January 13, 2009. ^[8]

See also

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

References

1. Reidies AH (June 2000). "Manganese compounds.". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_123. ISBN   978-3-527-30385-4.
2. Liu C, Liu Z, Fang Y, Du Z, Yan Z, Yuan X, et al. (2022-12-01). "Exposure to the environmentally toxic pesticide maneb induces Parkinson's disease-like neurotoxicity in mice: A combined proteomic and metabolomic analysis". Chemosphere. 308: 136344. doi:10.1016/j.chemosphere.2022.136344. ISSN   0045-6535.
3. "MANEB" (PDF). Hazardous Substance Fact Sheet. New Jersey Department of Health and Senior Services.
4. Costello S, Cockburn M, Bronstein J, Zhang X, Ritz B (April 2009). "Parkinson's disease and residential exposure to maneb and paraquat from agricultural applications in the central valley of California". American Journal of Epidemiology. 169 (8): 919–926. doi:10.1093/aje/kwp006. PMC   2727231 . PMID   19270050.
5. Garcinuño RM, Fernández-Hernando P, Cámara C (July 2004). "Simultaneous determination of maneb and its main metabolites in tomatoes by liquid chromatography using diode array ultraviolet absorbance detection". Journal of Chromatography A. 1043 (2): 225–229. doi:10.1016/j.chroma.2004.05.059. PMID   15330096.
6. Cicchetti F, Drouin-Ouellet J, Gross RE (September 2009). "Environmental toxins and Parkinson's disease: what have we learned from pesticide-induced animal models?". Trends in Pharmacological Sciences. 30 (9): 475–483. doi:10.1016/j.tips.2009.06.005. PMID   19729209.
7. "Interpretation of criteria for approval of active substances in the proposed EU plant protection regulation". Swedish Chemicals Agency (KemI). 2008-09-23. Archived from the original on 2009-01-01. Retrieved 2009-01-14.
8. "MEPs approve pesticides legislation". 2009-01-13. Archived from the original on 2009-01-25. Retrieved 2009-01-14.

External links

• Maneb in the Pesticide Properties DataBase (PPDB)
• US 4217293A,Adams, John B,"Stabilized maneb and preparation thereof",published 1980-08-12,issued 1980-08-12and EIDP Inc