Carbendazim (original) (raw)

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Carbendazim[1]
Names
Preferred IUPAC name Methyl (1_H_-1,3-benzimidazol-2-yl)carbamate
Other namesMercarzoleCarbendazole
Identifiers
CAS Number 10605-21-7 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:3392 ☒N
ChEMBL ChEMBL70971 checkY
ChemSpider 23741 checkY
ECHA InfoCard 100.031.108 Edit this at Wikidata
KEGG C10897 checkY
PubChem CID 25429
RTECS number DD6500000
UNII H75J14AA89 checkY
CompTox Dashboard (EPA) DTXSID4024729 Edit this at Wikidata
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) checkYKey: TWFZGCMQGLPBSX-UHFFFAOYSA-N checkYInChI=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)Nc2nc1ccccc1[nH]2
Properties
Chemical formula 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)
Solubility in water 8 mg/LDisintegration = 302 -305 degree Temperature of disintegration = 1.5 - 2 hrs
Acidity (p_K_a) 4.48
Hazards
NIOSH (US health exposure limits):
PEL (Permissible) Disintegration temp = 302 - 305 degreeDisintegration 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 ?) Infobox references

Chemical compound

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]

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]

  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.