:Maneb
{{Update|reason={{PMID|36029574}}|date=February 2024}}
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| ImageFile = Maneb.svg
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| IUPACName = 2-[(Dithiocarboxy)amino]ethyl]carbamodithioato(2-)-kS,kS']manganese
| OtherNames = Manganese ethylene-1,2-bisdithiocarbamate, polymer
|Section1={{Chembox Identifiers
| CASNo = 12427-38-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K221E12G7T
| 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
| InChIKey = YKSNLCVSTHTHJA-UHFFFAOYSA-L
| PubChem = 3032581
| MeSHName = Maneb
| 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-]
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2297517 }}
|Section2={{Chembox Properties
| Formula = (C4H6MnN2S4)n
| Appearance = Yellow to brown colored crystalline solid
| Density = 1.92 g/cm3
| MeltingPtC = 192 to 204
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = 160 mg/L }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
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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.{{cite book | vauthors = Reidies AH | chapter = Manganese compounds. | title = Ullmann's Encyclopedia of Industrial Chemistry | date = June 2000 | doi = 10.1002/14356007.a16_123 | isbn = 978-3-527-30385-4 }}
Health effects
{{See also|Manganism|Parkinsonism|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.{{Cite journal |last=Liu |first=Chaoyang |last2=Liu |first2=Zehua |last3=Fang |first3=Yanyan |last4=Du |first4=Zhen |last5=Yan |first5=Zhi |last6=Yuan |first6=Xin |last7=Dai |first7=Lijun |last8=Yu |first8=Ting |last9=Xiong |first9=Min |last10=Tian |first10=Ye |last11=Li |first11=Honghu |last12=Li |first12=Fei |last13=Zhang |first13=Jingdong |last14=Meng |first14=Lanxia |last15=Wang |first15=Zhihao |date=2022-12-01 |title=Exposure to the environmentally toxic pesticide maneb induces Parkinson's disease-like neurotoxicity in mice: A combined proteomic and metabolomic analysis |url=https://www.sciencedirect.com/science/article/abs/pii/S0045653522028375#:~:text=The%20predominant%20degradation%20product%20of,et%20al.,%202018). |journal=Chemosphere |volume=308 |pages=136344 |doi=10.1016/j.chemosphere.2022.136344 |issn=0045-6535|url-access=subscription }} It is still challenged whether maneb, along with Paraquat, is an environmental risk factor for Parkinson's disease.{{Cite web |title=MANEB | work = Hazardous Substance Fact Sheet | publisher = New Jersey Department of Health and Senior Services |url=https://nj.gov/health/eoh/rtkweb/documents/fs/1154.pdf }}{{cite journal | vauthors = Costello S, Cockburn M, Bronstein J, Zhang X, Ritz B | title = Parkinson's disease and residential exposure to maneb and paraquat from agricultural applications in the central valley of California | journal = American Journal of Epidemiology | volume = 169 | issue = 8 | pages = 919–926 | date = April 2009 | pmid = 19270050 | pmc = 2727231 | doi = 10.1093/aje/kwp006 }}
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.{{cite journal | vauthors = Garcinuño RM, Fernández-Hernando P, Cámara C | title = Simultaneous determination of maneb and its main metabolites in tomatoes by liquid chromatography using diode array ultraviolet absorbance detection | journal = Journal of Chromatography A | volume = 1043 | issue = 2 | pages = 225–229 | date = July 2004 | pmid = 15330096 | doi = 10.1016/j.chroma.2004.05.059 }}{{cite journal | vauthors = Cicchetti F, Drouin-Ouellet J, Gross RE | title = Environmental toxins and Parkinson's disease: what have we learned from pesticide-induced animal models? | journal = Trends in Pharmacological Sciences | volume = 30 | issue = 9 | pages = 475–483 | date = September 2009 | pmid = 19729209 | doi = 10.1016/j.tips.2009.06.005 }}
Environmental effects
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Regulation
Maneb was included in a pesticide ban proposed by the Swedish Chemicals Agency{{cite web|url=http://www.kemi.se/templates/News____5415.aspx |title=Interpretation of criteria for approval of active substances in the proposed EU plant protection regulation |date=2008-09-23 |publisher=Swedish Chemicals Agency (KemI) |access-date=2009-01-14 |url-status=dead |archive-url=https://web.archive.org/web/20090101024604/http://www.kemi.se/templates/News____5415.aspx |archive-date=2009-01-01 }} and approved by the European Parliament on January 13, 2009.{{cite web|url=http://www.europarl.europa.eu/news/expert/infopress_page/066-45937-012-01-03-911-20090112IPR45936-12-01-2009-2009-false/default_en.htm |title=MEPs approve pesticides legislation |date=2009-01-13 |access-date=2009-01-14 |url-status=dead |archive-url=https://web.archive.org/web/20090125031216/http://www.europarl.europa.eu/news/expert/infopress_page/066-45937-012-01-03-911-20090112IPR45936-12-01-2009-2009-false/default_en.htm |archive-date=2009-01-25 }}
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
{{reflist}}
External links
- {{PPDB|426}}
- {{Cite patent|country=US|number=4217293A|title=Stabilized maneb and preparation thereof|pubdate=1980-08-12|gdate=1980-08-12|invent1=Adams|inventor1-first=John B|assign2=EIDP Inc|url=https://worldwide.espacenet.com/patent/search/family/026700900/publication/US4217293A?q=pn%3DUS4217293A}}
{{Monoamine neurotoxins}}
Category:Aldehyde dehydrogenase inhibitors
Category:Manganese(II) compounds