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
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)
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
Title | Date | PubMed |
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A transient dysfunction of the neuromuscular junction due to carbendazim intoxication. | 2001 Apr |
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Direct action of the biocide carbendazim on phenolic metabolism in tobacco plants. | 2001 Jan |
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The in vivo gut micronucleus test detects clastogens and aneugens given by gavage. | 2001 Jan |
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The role of GTP Binding and microtubule-associated proteins in the inhibition of microtubule assembly by carbendazim. | 2001 Jan |
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Pesticide residues in oranges from Valencia (Spain). | 2001 Jul |
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Analysis of post-harvest fungicides by micellar electrokinetic chromatography. | 2001 Jul 27 |
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Mixed-mode solid-phase extraction and cleanup procedures for the liquid chromatographic determination of thiabendazole and carbendazim in fruit juices. | 2001 Mar-Apr |
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Exploring the mechanisms of action of FB642 at the cellular level. | 2001 May |
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[In vitro study of the antimutagenic activity of alphahederin]. | 2001 May-Jun |
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Stage-specific effects of the fungicide carbendazim on Sertoli cell microtubules in rat testis. | 2002 Apr |
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Validating the enchytraeid reproduction test: organisation and results of an international ringtest. | 2002 Feb |
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Induction of aneuploidy in male mouse germ cells detected by the sperm-FISH assay: a review of the present data base. | 2002 Jul 25 |
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Differential sensitivity of two green algae, Scenedesmus obliqnus and Chlorella pyrenoidosa, to 12 pesticides. | 2002 May |
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Statistical results and implications of the enchytraeid reproduction ringtest. | 2002 May 15 |
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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 |
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On-line automated sample preparation for liquid chromatography using parallel supported liquid membrane extraction and microporous membrane liquid-liquid extraction. | 2002 Oct 25 |
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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 |
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Cynodontin: a fungal metabolite with antifungal properties. | 2003 Aug 13 |
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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 |
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Determination of seventeen polar/thermolabile pesticides in apples and apricots by liquid chromatography/mass spectrometry. | 2003 May-Jun |
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A benzimidazole fungicide, benomyl, and its metabolite, carbendazim, induce aromatase activity in a human ovarian granulose-like tumor cell line (KGN). | 2004 Apr |
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Assessing structural and functional plankton responses to carbendazim toxicity. | 2004 Feb |
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Biology and integrated control of Pestalotiopsis on container-grown ericaceous crops. | 2004 Feb |
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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 |
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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 |
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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 |
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Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes. | 2004 Jan 9 |
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Modeling the dietary pesticide exposures of young children. | 2004 Jul-Sep |
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Quantification of the particle method for chemotactic bioassay using Peronosporomycete zoospores. | 2004 Nov-Dec |
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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 |
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Pesticide residues on the external surfaces of field crop sprayers: occupational exposure. | 2005 Jun |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 02:48:54 UTC 2021
by
admin
on
Sat Jun 26 02:48:54 UTC 2021
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Record UNII |
H75J14AA89
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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
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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
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Code System | Code | Type | Description | ||
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10605-21-7
Created by
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | Merck Index | ||
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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
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PRIMARY | |||
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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
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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
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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
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PRIMARY | |||
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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
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PRIMARY | USP-RS |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE | |||
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |