Maneb

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

Maneb

Names
IUPAC name [[2-[(Dithiocarboxy)amino]ethyl]carbamodithioato]](2-)-kS,kS']manganese
Other names Manganese ethylene-1,2-bisdithiocarbamate, polymer
Identifiers
CAS Number	12427-38-2 Y
3D model (JSmol)	Interactive image
ChemSpider	2297517 N
ECHA InfoCard	100.032.400
MeSH	Maneb
PubChem CID	3032581
UNII	K221E12G7T Y
CompTox Dashboard (EPA)	DTXSID9020794
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
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-]
Properties
Chemical formula	(C4H6MnN2S4)n
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)
Solubility in water	160 mg/L
Hazards
GHS labelling:
Pictograms
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]

Environmental effects

Environmental Impacts

Dithiocarbamates, commonly used as fungicides, can have significant environmental effects, particularly impacting aquatic life and potentially leading to neurotoxicity. They are known to be teratogenic in some species, and can cause oxidative stress and mitochondrial dysfunction. ^[7]

Aquatic Toxicity

Dithiocarbamates are toxic to aquatic organisms, with some studies showing them to be several orders of magnitude more toxic than their degradation product, ethylenethiourea (ETU).^[8]

Teratogenicity

They can cause developmental abnormalities, particularly in fish, such as spinal curvature, notochord distortion, and shortened anterior-posterior axis. ^[9]

Mitochondrial Dysfunction and Oxidative Stress

Dithiocarbamates can induce mitochondrial dysfunction and oxidative stress in various cell types, including dopaminergic cells and potentially contributing to neurodegenerative diseases like Parkinson's. ^[10]

Neurotoxicity

Studies have shown that dithiocarbamates can be neurotoxic, and combined exposure with other pesticides like glyphosate can exacerbate these effects. ^[11]

Mental Accumulation

Exposure to dithiocarbamates can lead to increased levels of metals like copper, manganese, and zinc in cells and tissues. ^[12]

Environmental Persistence

While they are known to degrade relatively quickly in the environment through hydrolysis and photolysis, they can still be frequently detected in environmental and food samples. ^[13]

Regulation

Maneb was included in a pesticide ban proposed by the Swedish Chemicals Agency^[14] and approved by the European Parliament on January 13, 2009.^[15]

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.