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Record Information
Version2.0
Creation Date2009-06-17 23:53:01 UTC
Update Date2014-12-24 20:22:58 UTC
Accession NumberT3D0942
Identification
Common NameCarbendazim
ClassSmall Molecule
DescriptionCarbendazim is a widely used, broad-spectrum benzimidazole fungicide. It is also a metabolite of benomyl (another widely used fungicide). It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. Carbendazim is used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes. It is also used in Queensland, Australia on macadamia plantations. Carbendazim is absorbed through the roots and green tissues. It acts by inhibiting beta-tubulin synthesis, inhibiting development of germ tubes and the growth of mycelia. It is compatible with most of the insecticides. It is used for the control of blast, sheath blight, brown spot, powdery mildew, scab, anthracnose and leaf spot diseases in various crops. The primary source of carbendazim exposure for the public at large is dietary intake.
Compound Type
  • Carbamate
  • Ether
  • Food Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1H-Benzimidazol-2-yl-carbamic acid, methyl ester
1H-Benzimidazol-2-ylcarbamic acid methyl ester
1H-Benzimidazol-2-ylcarbamic acid, methyl ester
1H-Benzimidazole-2-carbamic acid, methyl ester
2-(Carbomethoxyamino)benzimidazole
2-(Methoxy-carbonylamino)-benzimidazol
2-(Methoxycarbamoyl)benzimidazole
2-(Methoxycarbonylamino)-benzimidazole
2-(Methoxycarbonylamino)benzimidazole
2-(Methoxycarboxamido)benzimidazole
2-Benzimidazolecarbamic acid, methyl ester
2-Bezimidazolecarbamic acid methyl ester
2-MBC
2-Methyl benzimidazolecarbamate
2-[(Methoxycarbonyl)amino]benzimidazole
A 118 (Pesticide)
Agrizim
Antibac MF
Battal
Bavistan
Bavistin
Bavistin 25SD
Bavistin 3460
Bavistin 50SD
Bavistin FL
Bavistine
BCM
BCM (fungicide)
Bengard
Benzimidazole carbamate de methyle
Benzimidazole-2-carbamic acid, methyl ester
Benzimidazolecarbamate methyl ester
Benzimidazolecarbamic
Bercema-bitosen
Bitosen
BMC
BMC?
BMK
BMK (fungicide)
Carbamic acid, 1H-benzimidazol-2-yl-, methyl ester
Carbamic acid, 1H-benzimidazolyl-, methyl ester
Carbamic acid, N-1H-benzimidazol-2-yl-, methyl ester
Carben VL
Carbendazime
Carbendazin
Carbendazine
Carbendazol
Carbendazol, JMAF
Carbendazole
Carbendazym
Carbendazyme
Custos
Delsene
Delsene 10
Derosal
Derosal 60PM
Equitdazin
Falicarben
Funaben
Funaben 3
Funaben 50
Fungisol
Fungoxan
Garbenda
Ipo y
Jkatein
Jkstein
Karben
Karben flo stefes
Karben stefes flo
Kemdazin
Kid pest project (carbendazim) (see also carbendazim)
Kolfugo
Kolfugo 25 FW
Kolfugo 25FW
Kolfugo extra
MBC
Mecarzole
Medamine
Mekarzole
Methoxybenzimidazole-2-carbamic acid
Methyl 1H-benzimidazol-2-ylcarbamate
Methyl 1H-benzimidazol-2-ylcarbamate (9CI)
Methyl 1H-benzimidazol-2-ylcarbamate, 9CI
Methyl 1H-benzimidazole-2-carbamate
Methyl 1H-benzimidazolylcarbamate
Methyl 2-benzimidazil carbamate
Methyl 2-benzimidazolecarbamate
Methyl 2-benzimidazolylcarbamate
Methyl benzimidazol-2-ylcarbamate
Methyl benzimidazolecarbamate
Methyl benzimidazolylcarbamate
Methyl N-2-benzimidazolecarbamate
Methyl-2-benzimidazole carbamate
Methyl-N-(2-benzimidazolyl)carbamate
Methylbenzimidazole-2-ylcarbamate
MYCO
Olgin
Olgin (fungicide)
Pillarstin
Preparation G 665
Preventol BCM
Protek
Sarfun
SPIN
Spin (pesticide)
Stein
Stempor
Subeej
Supercarb
Thicoper
Triticol
Zhiweiling
Chemical FormulaC9H9N3O2
Average Molecular Mass191.187 g/mol
Monoisotopic Mass191.069 g/mol
CAS Registry Number10605-21-7
IUPAC Namemethyl N-(1H-1,3-benzodiazol-2-yl)carbamate
Traditional Namecarbendazim
SMILESCOC(O)=NC1=NC2=CC=CC=C2N1
InChI IdentifierInChI=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)
InChI KeyInChIKey=TWFZGCMQGLPBSX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub Class2-benzimidazolylcarbamic acid esters
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Benzenoid
  • Azole
  • Imidazole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point302 - 307°C
Boiling PointNot Available
Solubility0.029 mg/mL at 24°C [TOMLIN,C (1994); pH4]
LogP1.52
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP1.46ALOGPS
logP1.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.7ChemAxon
pKa (Strongest Basic)4.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.01 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.93 m³·mol⁻¹ChemAxon
Polarizability19.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2900000000-c38742ca2595eba7bf98JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ox-0900000000-d0dcee8e90dd2a9993f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dl-0900000000-66f156e60b1311d8b254JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-b90e9baa17181b672c3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-6ab35560f7e1a5a65449JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-73665298def00103c4ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-1900000000-c2671f61f53982f0cc4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0apl-6900000000-e681bc1cde4f51afdafdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9400000000-1bb84be4e51073c98b31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9100000000-676d7e392680b811a06cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-082f61a661f5a52de8cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-9d9c815da13027c56035JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-11745a93c352387eea88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-1900000000-d6a2d8c38ca15c4d2b9bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-06rx-5900000000-05ffdb42cffce5ceb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-051728e55a00c7dde9f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-44ac13539ddcb90a7a2bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-007ce1c2131b034a4182JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-007ce1c2131b034a4182JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-8f8ad13c0f401efa32e1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-8f94ad998218e7c8abefJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-d0300c3c3948b07bf1a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-64023674830421466f70JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-2900000000-efc6d5d10e75b8d52207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-30793d33e9633e88a744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-4900000000-e86721cd79188af2103fJSpectraViewer
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4); dermal (4)
Mechanism of ToxicityCarbendazim targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (2).
MetabolismThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (4)
Toxicity ValuesAcute oral LD50 for rats is >15000 mg/kg and >2500 mg/kg for dogs
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is a systemic fungicide that is selectively toxic to microorganisms and invertebrates. It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. It is also used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes.
Minimum Risk LevelThe MRLs for fresh produce in the European Union are now between 0.1 and 0.7 mg/kg
Health EffectsCarbendazim is a suspected endocrine disruptor. It is also a developmental toxin. Animals exposed to carbendazim in the womb to have serious deformities such as lack of eyes and hydrocephalus (water on the brain). Carbendazim can disrupt the development of sperm and damage testicular development in adult rats.
SymptomsSkin redness and skin irritation. Fetuses exposed to high levels may exhibit microphthalmia (small eyes) or anaphthalmia (no eyes).
TreatmentFor acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31769
PubChem Compound ID25429
ChEMBL IDCHEMBL70971
ChemSpider ID23741
KEGG IDC10897
UniProt IDNot Available
OMIM ID
ChEBI ID3392
BioCyc IDNot Available
CTD IDC006698
Stitch IDCarbendazim
PDB IDNot Available
ACToR ID5785
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Narayana KJ, Prabhakar P, Vijayalakshmi M, Venkateswarlu Y, Krishna PS: Biological activity of phenylpropionic acid isolated from a terrestrial Streptomycetes. Pol J Microbiol. 2007;56(3):191-7. [18062653 ]
  2. Clement MJ, Rathinasamy K, Adjadj E, Toma F, Curmi PA, Panda D: Benomyl and colchicine synergistically inhibit cell proliferation and mitosis: evidence of distinct binding sites for these agents in tubulin. Biochemistry. 2008 Dec 9;47(49):13016-25. doi: 10.1021/bi801136q. [19049291 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  4. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  5. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Ubiquitin protein ligase binding
Specific Function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name:
TUBB
Uniprot ID:
P07437
Molecular Weight:
49670.515 Da
References
  1. Fujimura M, Oeda K, Inoue H, Kato T. "A single amino-acid substitution in the beta-tubulin gene of Neurospora confers both carbendazim resistance and diethofencarb sensitivity.". Curr Genet. 1992 Apr;21(4-5):399-404. [1388107 ]
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC507.36 uMAPR_p53Act_72h_upApredica
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]