Carbendazim

Carbendazim^[1]

Names
IUPAC name Methyl 1H-benzimidazol-2-ylcarbamate
Other names Mercarzole Carbendazole
Identifiers
CAS Number	10605-21-7
ChEBI	CHEBI:3392
ChEMBL	ChEMBL70971
ChemSpider	23741
Jmol interactive 3D	Image
KEGG	C10897
PubChem	25429
RTECS number	DD6500000
UNII	H75J14AA89
InChI 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) Key: TWFZGCMQGLPBSX-UHFFFAOYSA-N 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
SMILES O=C(OC)Nc2nc1ccccc1n2
Properties
Chemical formula	C9H9N3O2
Molar mass	191.187 g/mol
Appearance	Light gray powder
Density	1.45 g/cm^3
Melting point	302 to 307 °C (576 to 585 °F; 575 to 580 K) (decomposes)
Solubility in water	8 mg/L
Acidity (pKa)	4.48
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 widely used, broad-spectrum benzimidazole fungicide and a metabolite of benomyl. 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.^[2]

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

Studies have found high doses of carbendazim cause infertility and destroy the testicles of laboratory animals.^[5][6]

Maximum pesticide residue limits (MRLs) have reduced since discovering its harmful effects. The MRLs for fresh produce in the EU are now between 0.1 and 0.7 mg/kg with the exception of loquat, which is 2 mg/kg.^[7] The limits for more commonly consumed citrus and pomme fruits are between 0.1 and 0.2 mg/kg.

References

1. Merck Index, 11th Edition, 1794.
2. "Getting the best worm control".
3. Wight, Andrew (14 January 2009). "Two-headed fish mystery deepens". Stock & Land. Archived from the original on 11 January 2012.
4. Marissa Calligeros (2009-02-02). "Fungicide maker in birth defect storm". Sydney Morning Herald. Retrieved 2010-03-21.
5. 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.
6. "Carbendazim use banned on fruit crops". ABC. 5 February 2010.
7. "EU Pesticides Database". Retrieved 24 February 2012.

External links

• International Chemical Safety Card
• Carbendazim in the Pesticide Properties DataBase (PPDB)