Maneb

Maneb
Names
IUPAC name
[[2-[(Dithiocarboxy)amino]ethyl]carbamodithioato]](2-)-kS,kS']manganese
Other names
Manganese ethylene-1,2-bisdithiocarbamate, polymer
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.400 Edit this at Wikidata
MeSH Maneb
UNII
  • 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
  • [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
(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)
160 mg/L
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Health effects

Exposure to maneb can occur when breathed in; it can irritate the eyes, nose, and throat as well as cause headaches, fatigue, nervousness, dizziness, seizures and 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. The link between maneb and Parkinson's disease had been suspected since the early 2000s; but however, a 2022 review concluded that maneb, alongside other pesticides like MPTP, paraquat, and rotenone, play a prominent role in the development of the disease. More investigation is needed to investigate its underlying mechanism of action.

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.

Environmental effects

Maneb will decompose into Ethylene thiourea, Mn2+, CS2, CO2, and NH3 upon exposure with air or moisture. Maneb's decomposition products are largely influenced by environmental factors.

Regulation

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

See also

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 (Pt 2) 136344. Bibcode:2022Chmsp.30836344L. doi:10.1016/j.chemosphere.2022.136344. ISSN 0045-6535. PMID 36087732.
  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. ↑ Vellingiri B, Chandrasekhar M, Sri Sabari S, Gopalakrishnan AV, Narayanasamy A, Venkatesan D, et al. (September 2022). "Neurotoxicity of pesticides - A link to neurodegeneration". Ecotoxicol Environ Saf. 243 113972. Bibcode:2022EcoES.24313972V. doi:10.1016/j.ecoenv.2022.113972. PMID 36029574.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ Xi Y, Zhang Z, Lin Z, Peng K, Chen S, Zhu Q, et al. (2026). "Advances in the neurotoxicity of ecological pesticide maneb: mechanisms and implications for human health". Frontiers in Public Health. 14 1745443. Bibcode:2026FrPH...1445443X. doi:10.3389/fpubh.2026.1745443. ISSN 2296-2565. PMC 12907399. PMID 41705050.
  9. ↑ "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.
  10. ↑ "MEPs approve pesticides legislation". 2009-01-13. Archived from the original on 2009-01-25. Retrieved 2009-01-14.