Chemistry:Carbendazim

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Carbendazim[1]
Carbendazim Structural Formulae V.1.svg
Names
Preferred IUPAC name
Methyl (1H-1,3-benzimidazol-2-yl)carbamate
Other names
Mercarzole
Carbendazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
RTECS number
  • DD6500000
UNII
Properties
C9H9N3O2
Molar mass 191.187 g/mol
Appearance Light gray powder
Density 1.45 g/cm3
Melting point 302 to 307 °C (576 to 585 °F; 575 to 580 K) (decomposes)
8 mg/L

Disintegration = 302 -305 degree Temperature of disintegration = 1.5 - 2 hrs

Acidity (pKa) 4.48
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
Disintegration temp = 302 - 305 degree

Disintegration temp = 1.5 - 2 hrs

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carbendazim is a fungicide, a member benzimidazole fungicides. It is metabolized to benomyl, which is bioactive.[2]

The fungicide is used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, macadamia nuts, pineapples, and pomes.[3] A 4.7% solution of carbendazim hydrochloride, sold as Eertavas, is marketed as a treatment for Dutch elm disease.[4]

Other uses

It is also employed as a casting worm control agent in amenity turf situations such as golf greens, tennis courts etc. and in some countries is licensed for that use only.[5]

Safety, regulation, controversy

High doses of carbendazim cause infertility and destroy the testicles of laboratory animals.[6][7]

Maximum pesticide residue limits (MRLs) for fresh produce in the EU are between 0.1 and 0.7 mg/kg with the exception of loquat, which is 2 mg/kg.[8] The limits for more commonly consumed citrus and pome fruits are between 0.1 and 0.2 mg/kg.

Its use on macadamia plantations has proven controversial in Queensland.[4]

References

  1. Merck Index, 11th Edition, 1794.
  2. Dreikorn, Barry A.; Owen, W. John (2000). "Fungicides, Agricultural". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0621140704180509.a01. ISBN 978-0-471-48494-3. 
  3. Wight, Andrew (14 January 2009). "Two-headed fish mystery deepens". Stock & Land. http://sl.farmonline.com.au/news/nationalrural/agribusiness-and-general/general/twoheaded-fish-mystery-deepens/1406893.aspx?storypage=0. 
  4. 4.0 4.1 Marissa Calligeros (2009-02-02). "Fungicide maker in birth defect storm". Sydney Morning Herald. http://www.smh.com.au/news/environment/fungicide-maker-in-birth-defect-storm/2009/02/02/1233423096718.html. 
  5. "Getting the best worm control". http://www.sherriffamenity.com/technicalupdates/Getting-The-Best-Worm-Control/90/. 
  6. Aire, TA (August 2005). "Short-term effects of carbendazim on the gross and microscopic features of the testes of Japanese quails (Coturnix coturnix japonica).". Anatomy and Embryology 210 (1): 43–9. doi:10.1007/s00429-005-0001-0. PMID 16034611. 
  7. "Carbendazim use banned on fruit crops". ABC. 5 February 2010. http://www.abc.net.au/rural/news/content/201002/s2811428.htm. 
  8. "EU Pesticides Database". http://ec.europa.eu/sanco_pesticides/public/index.cfm. 

External links