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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
Carbendazim-induced haematological, biochemical and histopathological changes to the liver and kidney of male rats.
2001 Dec
[Elimination of carbendazim from fruit conditioning waters by adsorption on different materials].
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
Spermatotoxic effect of carbendazim.
2001 Sep
Application of a mixed-mode solid-phase extraction and cleanup procedure for LC/MS determination of thiabendazole and carbendazim in apple juice.
2001 Sep-Oct
Effects of carbendazim on rat thyroid, parathyroid, pituitary and adrenal glands and their hormones.
2002 Apr
Electrochemical detection of carbamate pesticides at conductive diamond electrodes.
2002 Apr 1
Validating the enchytraeid reproduction test: organisation and results of an international ringtest.
2002 Feb
Is the application of carbendazim harmful to healthy plants? Evidence of weak phytotoxicity in tobacco.
2002 Jan 16
Complexation of several benzimidazole-type fungicides with alpha- and beta-cyclodextrins.
2002 Jan 2
Induction of aneuploidy in male mouse germ cells detected by the sperm-FISH assay: a review of the present data base.
2002 Jul 25
Multiresidue determination of pesticides in drinking and related waters by solid-phase extraction and liquid chromatography with ultraviolet detection: interlaboratory study.
2002 Mar-Apr
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
Validation of a method for the determination of multiclass pesticide residues in fruit juices by liquid chromatography/tandem mass spectrometry after extraction by matrix solid-phase dispersion.
2002 May-Jun
On-line automated sample preparation for liquid chromatography using parallel supported liquid membrane extraction and microporous membrane liquid-liquid extraction.
2002 Oct 25
Microtubules of the mouse testis exhibit differential sensitivity to the microtubule disruptors Carbendazim and colchicine.
2002 Sep
Comparison of microextraction procedures to determine pesticides in oranges by liquid chromatography-mass spectrometry.
2002 Sep 13
Solubilization and preformulation of carbendazim.
2002 Sep 5
Application of GRAM and TLD to the resolution and quantitation of real complex multicomponent mixtures by fluorescence spectroscopy.
2003 Apr
Indirect mechanisms of genotoxicity.
2003 Apr 11
Occurrence of pesticide residues in mushrooms in Northern Ireland, July 1997-January 1999.
2003 Aug
Cynodontin: a fungal metabolite with antifungal properties.
2003 Aug 13
Photochemical behaviour of carbendazim in aqueous solution.
2003 Feb
Mode of action and pesticidal activity of the natural product dunnione and of some analogues.
2003 Feb
[Presearch on preventing the medicinal plant diseases with Trichoderma harzianum preparation].
2003 Jan
[Genetics of resistance to carbendazim in Gibberella zeae].
2003 May
Fungicidal impact on chickpea--Mesorhizobium symbiosis.
2004
Assessing structural and functional plankton responses to carbendazim toxicity.
2004 Feb
Biology and integrated control of Pestalotiopsis on container-grown ericaceous crops.
2004 Feb
Use of terrestrial model ecosystem data in environmental risk assessment for industrial chemicals, biocides and plant protection products in the EU.
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 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 soil microarthropod communities.
2004 Feb-Mar
Ring-testing and field-validation of a terrestrial model ecosystem (TME)--an instrument for testing potentially harmful substances: fate of the model chemical carbendazim.
2004 Feb-Mar
Re-identification and characterization of pathogens causing ugurassa (Flacourtia inermis) fruit anthracnose.
2004 Jan
Microwave-assisted extraction for the simultaneous determination of thiamethoxam, imidacloprid, and carbendazim residues in fresh and cooked vegetable samples.
2004 Jan 14
Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes.
2004 Jan 9
2,5-hexanedione and carbendazim coexposure synergistically disrupts rat spermatogenesis despite opposing molecular effects on microtubules.
2004 Jul
Pesticide levels in surface waters in an agricultural-forestry basin in Southern Chile.
2004 Nov
Pesticide residues on the external surfaces of field crop sprayers: occupational exposure.
2005 Jun
Dose-dependent effects of carbendazim on rat thymus.
2005 Nov-Dec
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