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Carbendazim

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Carbendazim[1]
Names
Preferred IUPAC name
Methyl (1H-1,3-benzimidazol-2-yl)carbamate
Other names
Mercarzole
Carbendazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.031.108 Edit this at Wikidata
KEGG
RTECS number
  • DD6500000
UNII
  • InChI=1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13) checkY
    Key: TWFZGCMQGLPBSX-UHFFFAOYSA-N checkY
  • InChI=1/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)
    Key: TWFZGCMQGLPBSX-UHFFFAOYAS
  • COC(=O)Nc2nc1ccccc1[nH]2
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).
☒N verify (what is checkY☒N ?)

Carbendazim is a fungicide, a member benzimidazole fungicides. It is a metabolite of benomyl.[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

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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

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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

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  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. Archived from the original on 19 October 2009.
  4. ^ a b Marissa Calligeros (2009-02-02). "Fungicide maker in birth defect storm". Sydney Morning Herald. Retrieved 2010-03-21.
  5. ^ "Getting the best worm control".
  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. S2CID 8526462.
  7. ^ "Carbendazim use banned on fruit crops". ABC. 5 February 2010.
  8. ^ "EU Pesticides Database". Retrieved 24 February 2012.
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