Carbendazim - Misplaced Pages

Carbendazim
Names

Preferred IUPAC name Methyl (1H-1,3-benzimidazol-2-yl)carbamate
Other names Mercarzole Carbendazole
Identifiers
CAS Number	10605-21-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3392
ChEMBL	ChEMBL70971
ChemSpider	23741
ECHA InfoCard	100.031.108
KEGG	C10897
PubChem CID	25429
RTECS number	DD6500000
UNII	H75J14AA89
CompTox Dashboard (EPA)	DTXSID4024729
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 COC(=O)Nc2nc1ccccc12
Properties
Chemical formula	C₉H₉N₃O₂
Molar mass	191.187 g/mol
Appearance	White to light gray powder
Density	1.45 g/cm
Melting point	302 to 307 °C (576 to 585 °F; 575 to 580 K) (decomposes)
Solubility in water	8 mg/L Disintegration = 302 -305 degree Temperature of disintegration = 1.5 - 2 hrs
Acidity (pK_a)	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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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

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

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.

Safety, regulation, controversy

High doses of carbendazim destroy the testicles of laboratory animals.

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 fruits, which is set at 2 mg/kg. The limits for more commonly consumed citrus and pome fruits are between 0.1 and 0.2 mg/kg.

Use of this fungicide on macadamia plantations has proven controversial in Queensland.

References

Merck Index, 11th Edition, 1794.
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.
Wight, Andrew (14 January 2009). "Two-headed fish mystery deepens". Stock & Land. Archived from the original on 19 October 2009.
^ Marissa Calligeros (2009-02-02). "Fungicide maker in birth defect storm". Sydney Morning Herald. Retrieved 2010-03-21.
"Getting the best worm control".
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.
"Carbendazim use banned on fruit crops". ABC. 5 February 2010.
"EU Pesticides Database". Retrieved 24 February 2012.