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Details

Stereochemistry ACHIRAL
Molecular Formula C9H9N3O2
Molecular Weight 191.187
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENDAZIM

SMILES

COC(=Nc1[nH]c2ccccc2n1)O

InChI

InChIKey=TWFZGCMQGLPBSX-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C9H9N3O2
Molecular Weight 191.187
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Carbendazim is a broad-spectrum benzimidazole antifungal with potential antimitotic and antineoplastic activities widely used as a fungicide in agriculture and home gardening, and as an antihelminthic in veterinary medicine. As a fungicide, carbendazim used for controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables. Carbendazim is a chemically stable and relatively persistent fungicide which only metabolizes to a limited extent in plants and in soil. The only detected metabolite is 2-aminobenzimidazole, which constitutes less than 5% of the total residues in leaves. Carbendazim may be anticipated to metabolize in the animal into hydroxylated analogues which may appear in meat and milk products. Carbendazim acts as a mitotic poison by altering tubulin binding and microtubule formation. This has been proposed as a possible mechanism of action for the developmental abnormalities seen in animal studies with high concentrations.

Approval Year

PubMed

PubMed

TitleDatePubMed
A transient dysfunction of the neuromuscular junction due to carbendazim intoxication.
2001 Apr
Direct action of the biocide carbendazim on phenolic metabolism in tobacco plants.
2001 Jan
The in vivo gut micronucleus test detects clastogens and aneugens given by gavage.
2001 Jan
The role of GTP Binding and microtubule-associated proteins in the inhibition of microtubule assembly by carbendazim.
2001 Jan
Pesticide residues in oranges from Valencia (Spain).
2001 Jul
Analysis of post-harvest fungicides by micellar electrokinetic chromatography.
2001 Jul 27
Mixed-mode solid-phase extraction and cleanup procedures for the liquid chromatographic determination of thiabendazole and carbendazim in fruit juices.
2001 Mar-Apr
Exploring the mechanisms of action of FB642 at the cellular level.
2001 May
[In vitro study of the antimutagenic activity of alphahederin].
2001 May-Jun
Stage-specific effects of the fungicide carbendazim on Sertoli cell microtubules in rat testis.
2002 Apr
Validating the enchytraeid reproduction test: organisation and results of an international ringtest.
2002 Feb
Induction of aneuploidy in male mouse germ cells detected by the sperm-FISH assay: a review of the present data base.
2002 Jul 25
Differential sensitivity of two green algae, Scenedesmus obliqnus and Chlorella pyrenoidosa, to 12 pesticides.
2002 May
Statistical results and implications of the enchytraeid reproduction ringtest.
2002 May 15
Determination of pesticide residues in coconut water by liquid-liquid extraction and gas chromatography with electron-capture plus thermionic specific detection and solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
2002 May 31
On-line automated sample preparation for liquid chromatography using parallel supported liquid membrane extraction and microporous membrane liquid-liquid extraction.
2002 Oct 25
Cytokinetic actomyosin ring formation and septation in fission yeast are dependent on the full recruitment of the polo-like kinase Plo1 to the spindle pole body and a functional spindle assembly checkpoint.
2002 Sep 15
Cynodontin: a fungal metabolite with antifungal properties.
2003 Aug 13
The alga Chlamydomonas reinhardtii UVS11 gene is responsible for cell division delay and temporal decrease in histone H1 kinase activity caused by UV irradiation.
2003 Jun 11
Determination of seventeen polar/thermolabile pesticides in apples and apricots by liquid chromatography/mass spectrometry.
2003 May-Jun
A benzimidazole fungicide, benomyl, and its metabolite, carbendazim, induce aromatase activity in a human ovarian granulose-like tumor cell line (KGN).
2004 Apr
Assessing structural and functional plankton responses to carbendazim toxicity.
2004 Feb
Biology and integrated control of Pestalotiopsis on container-grown ericaceous crops.
2004 Feb
Ring-testing and field-validation of a terrestrial model ecosystem (TME)--an instrument for testing potentially harmful substances: effects of carbendazim on nutrient cycling.
2004 Feb-Mar
Ring-testing and field-validation of a terrestrial model ecosystem (TME)--an instrument for testing potentially harmful substances: effects of carbendazim on earthworms.
2004 Feb-Mar
Ring-testing and field-validation of a terrestrial model ecosystem (TME)--an instrument for testing potentially harmful substances: effects of carbendazim on nematodes.
2004 Feb-Mar
Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes.
2004 Jan 9
Modeling the dietary pesticide exposures of young children.
2004 Jul-Sep
Quantification of the particle method for chemotactic bioassay using Peronosporomycete zoospores.
2004 Nov-Dec
Simultaneous separation and on-line concentration of amitrole and benzimidazole pesticides by capillary electrophoresis with a volatile migration buffer applicable to mass spectrometric detection.
2004 Oct 8
Pesticide residues on the external surfaces of field crop sprayers: occupational exposure.
2005 Jun
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:48:54 UTC 2021
Edited
by admin
on Sat Jun 26 02:48:54 UTC 2021
Record UNII
H75J14AA89
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBENDAZIM
HSDB   ISO   MI  
Common Name English
1H-BENZIMIDAZOLE-2-CARBAMIC ACID, METHYL ESTER
Common Name English
EK-578
Code English
FB-642
Code English
CARBENDAZIM [HSDB]
Common Name English
BAS-67054F
Code English
NSC-109874
Code English
A 118
Code English
THICOPER
Common Name English
FENBENDAZOLE RELATED COMPOUND A [USP-RS]
Common Name English
2-(METHOXYCARBONYLAMINO)BENZIMIDAZOLE
Systematic Name English
ALBENDAZOLE IMPURITY E [EP]
Common Name English
CARBENDAZIM [WHO-DD]
Common Name English
METHYL N-1H-BENZIMIDAZOL-2-YLCARBAMATE
Systematic Name English
FENBENDAZOLE RELATED COMPOUND A
USP-RS  
Common Name English
METHYL BENZIMIDAZOL-2-YLCARBAMATE
Systematic Name English
BAVISTIN
Brand Name English
CARBENDAZIM [ISO]
Common Name English
LIGNASAN
Common Name English
METHYL N-(1H-BENZIMIDAZOL-2-YL)CARBAMATE
Systematic Name English
CARBENDAZIM [MI]
Common Name English
DERROPRENE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128872
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
NCI_THESAURUS C67421
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
Code System Code Type Description
EPA CompTox
10605-21-7
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
NCI_THESAURUS
C1154
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
HSDB
6581
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
234-232-0
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
MERCK INDEX
M3062
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY Merck Index
FDA UNII
H75J14AA89
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
DRUG BANK
DB13009
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
PUBCHEM
25429
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
CAS
10605-21-7
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY
USP_CATALOG
1269414
Created by admin on Sat Jun 26 02:48:55 UTC 2021 , Edited by admin on Sat Jun 26 02:48:55 UTC 2021
PRIMARY USP-RS
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METABOLIC ENZYME -> INHIBITOR
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE
PARENT -> METABOLITE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY