Carbendazim

Title: Carbendazim
CAS Registry Number: 10605-21-7
CAS Name: 1H-Benzimidazol-2-ylcarbamic acid methyl ester
Additional Names: 2-benzimidazolecarbamic acid methyl ester; 2-(methoxycarbonylamino)benzimidazole; methyl 2-benzimidazolecarbamate; carbendazole; BMC; MBC; BCM
Manufacturers' Codes: BAS-3460; BAS-67054; CTR-6669; HOE-17411
Trademarks: Bavistin (BASF); Derosal (Hoechst); Delsene (DuPont)
Molecular Formula: C9H9N3O2
Molecular Weight: 191.19
Percent Composition: C 56.54%, H 4.74%, N 21.98%, O 16.74%
Literature References: Degradn product of benomyl, q.v. Prepn: H. M. Loux, US 3010968 (1961 to du Pont); H. A. Selling et al., Chem. Ind. (London) 1970, 1625. Activity: G. P. Clemons, H. D. Sisler, Pestic. Biochem. Physiol. 1, 32 (1971). Degradn in soil: A. Helweg, Pestic. Sci. 8, 71 (1977). Efficacy in controlling powdery mildew: G. R. Singh, T. B. Anilkumar, Indian J. Mycol. Plant Pathol. 16, 30 (1986). Review of environmental and toxicological effects: Carbendazim: Environ. Health Criteria 149, (World Health Organization, Geneva, 1993) 132 pp.
Properties: White powder, mp 302-307° (dec). pKa 4.48. Soly 20° (mg/ml): water, pH 7 8; pH 4 29. Soly 20° (mg/l): hexane 0.5; benzene 36; dichloromethane 68; ethanol 300; dimethylformamide 5000, chloroform 100, acetone 300. Slowly decomp in alkaline soln.
Melting point: mp 302-307° (dec)
pKa: pKa 4.48
Use: Fungicide.
Carbenicillin Carbenoxolone Carbetapentane Carbetocin Carbic Anhydride

Carbendazim[1]
Carbendazim Structural Formulae V.1.svg
Identifiers
CAS number 10605-21-7 YesY
PubChem 25429
ChemSpider 23741 YesY
UNII H75J14AA89 YesY
KEGG C10897 YesY
ChEMBL CHEMBL70971 YesY
RTECS number DD6500000
Jmol-3D images Image 1
Properties
Molecular formula C9H9N3O2
Molar mass 191.19 g mol−1
Appearance Light gray powder
Melting point 302-307 °C (decomposes)
Solubility in water 8 mg/L
Acidity (pKa) 4.48
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.