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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Carbendazim-induced haematological, biochemical and histopathological changes to the liver and kidney of male rats. | 2001 Dec |
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[Elimination of carbendazim from fruit conditioning waters by adsorption on different materials]. | 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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Spermatotoxic effect of carbendazim. | 2001 Sep |
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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 |
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Effects of carbendazim on rat thyroid, parathyroid, pituitary and adrenal glands and their hormones. | 2002 Apr |
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Electrochemical detection of carbamate pesticides at conductive diamond electrodes. | 2002 Apr 1 |
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Validating the enchytraeid reproduction test: organisation and results of an international ringtest. | 2002 Feb |
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Is the application of carbendazim harmful to healthy plants? Evidence of weak phytotoxicity in tobacco. | 2002 Jan 16 |
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Complexation of several benzimidazole-type fungicides with alpha- and beta-cyclodextrins. | 2002 Jan 2 |
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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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Multiresidue determination of pesticides in drinking and related waters by solid-phase extraction and liquid chromatography with ultraviolet detection: interlaboratory study. | 2002 Mar-Apr |
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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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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 |
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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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Microtubules of the mouse testis exhibit differential sensitivity to the microtubule disruptors Carbendazim and colchicine. | 2002 Sep |
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Comparison of microextraction procedures to determine pesticides in oranges by liquid chromatography-mass spectrometry. | 2002 Sep 13 |
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Solubilization and preformulation of carbendazim. | 2002 Sep 5 |
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Application of GRAM and TLD to the resolution and quantitation of real complex multicomponent mixtures by fluorescence spectroscopy. | 2003 Apr |
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Indirect mechanisms of genotoxicity. | 2003 Apr 11 |
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Occurrence of pesticide residues in mushrooms in Northern Ireland, July 1997-January 1999. | 2003 Aug |
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Cynodontin: a fungal metabolite with antifungal properties. | 2003 Aug 13 |
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Photochemical behaviour of carbendazim in aqueous solution. | 2003 Feb |
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Mode of action and pesticidal activity of the natural product dunnione and of some analogues. | 2003 Feb |
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[Presearch on preventing the medicinal plant diseases with Trichoderma harzianum preparation]. | 2003 Jan |
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[Genetics of resistance to carbendazim in Gibberella zeae]. | 2003 May |
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Fungicidal impact on chickpea--Mesorhizobium symbiosis. | 2004 |
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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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Use of terrestrial model ecosystem data in environmental risk assessment for industrial chemicals, biocides and plant protection products in the EU. | 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 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 soil microarthropod communities. | 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: fate of the model chemical carbendazim. | 2004 Feb-Mar |
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Re-identification and characterization of pathogens causing ugurassa (Flacourtia inermis) fruit anthracnose. | 2004 Jan |
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Microwave-assisted extraction for the simultaneous determination of thiamethoxam, imidacloprid, and carbendazim residues in fresh and cooked vegetable samples. | 2004 Jan 14 |
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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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2,5-hexanedione and carbendazim coexposure synergistically disrupts rat spermatogenesis despite opposing molecular effects on microtubules. | 2004 Jul |
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Pesticide levels in surface waters in an agricultural-forestry basin in Southern Chile. | 2004 Nov |
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Pesticide residues on the external surfaces of field crop sprayers: occupational exposure. | 2005 Jun |
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Dose-dependent effects of carbendazim on rat thymus. | 2005 Nov-Dec |
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
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10605-21-7
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C1154
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6581
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234-232-0
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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
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DB13009
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25429
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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
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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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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 |
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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 -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |