A carbamate fungicide and an active metabolite of benomyl and thiophanate-methyl
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Parent Compound(s)
34634Benomyl 35402Thiophanate-methyl
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Carbendazim

Item No. 23852

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-1H-benzimidazol-2-yl-carbamic acid, methyl ester
CAS Number
10605-21-7
Synonyms
  • A-118
  • methyl Benzimidazol-2-yl-carbamate
  • methyl 2-Benzimidazolecarbamate
  • MBC
  • NSC 109874
  • U-32104
Molecular Formula
C9H9N3O2
Formula Weight
191.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 25 mg/mlEthanol: 5 mg/ml
λmax
244, 281, 287 nm
SMILES
O=C(OC)NC1=NC2=CC=CC=C2N1
InChi Code
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)
InChi Key
TWFZGCMQGLPBSX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $36

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    Product Description

    Carbendazim is a carbamate fungicide and an active metabolite of benomyl (Item No. 34634) and thiophanate-methyl (Item No. 35402).1,2 It is also a degradation product of benomyl.3 Carbendazim is active against the plant pathogenic fungi N. parvum, B. dothidea, D. seriata, and L. theobromae in vitro (EC50s = 0.01-0.07 mg/L) and protects grapevines from pruning wounds caused by D. seriata or D. mutila in vivo.4 Carbendazim (100 µM) inhibits the growth of, and microtubule polymerization in, S. cerevisiae.5 It impairs meiosis and steroidogenesis in rat seminiferous tubules ex vivo and increases prostate weight in rats when administered at a dose of 100 mg/kg but does not affect other testosterone-dependent or estrogen-dependent tissues.6,7 It has been found as a contaminant in various jellies and jams and in wastewater influent and effluent.8,9 Formulations containing carbendazim have been used as preservatives for wood and other materials, as well as fungicides in agricultural and residential areas.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rouchaud, J.P., Lhoest, G.J., Mercier, M.J., et al. Metabolism of benomyl in carrot, strawberry and apple. Pestic. Sci. 8(1), 23-30 (1977).

    2. Lee, H.S., Rahman, M.M., Chung, H.S., et al. An effective methodology for simultaneous quantification of thiophanate-methyl, and its metabolite carbendazim in pear, using LC-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 1095, 1-7 (2018).

    3. Chiba, M., and Veres, D.F. Fate of benomyl and its degradation compound methyl 2-benzimidazolecarbamate on apple foliage. J. Agric. Food Chem. 29(3), 588-590 (1981).

    4. Amponsah, N.T., Jones, E., Ridgway, H.J., et al. Evaluation of fungicides for the management of Botryosphaeria dieback diseases of grapevines. Pest Manag. Sci. 68(5), 676-683 (2012).

    5. Quinlan, R.A., Pogson, C.I., and Gull, K. The influence of the microtubule inhibitor, methyl benzimidazol-2-yl-carbamate (MBC) on nuclear division and the cell cycle in Saccharomyces cerevisiae. J. Cell. Sci. 46, 341-352 (1980).

    6. Pisani, C., Voisin, S., Arafah, K., et al. Ex vivo assessment of testicular toxicity induced by carbendazim and iprodione, alone or in a mixture. ALTEX 33(4), 393-413 (2016).

    7. Rama, E.M., Bortolan, S., Vieira, M.L., et al. Reproductive and possible hormonal effects of carbendazim. Regul. Toxicol. Pharmacol. 69(3), 476-486 (2014).

    8. Makni, Y., Diallo, T., Areskoug, F., et al. Optimisation and implementation of QuEChERS-based sample preparation for identification and semi-quantification of 694 targeted contaminants in honey, jam, jelly, and syrup by UHPLC-Q/ToF high-resolution mass spectrometry. Food Chem. 425, 136448 (2023).

    9. Hermes, N., Jewell, K.S., Wick, A., et al. Quantification of more than 150 micropollutants including transformation products in aqueous samples by liquid chromatography-tandem mass spectrometry using scheduled multiple reaction monitoring. J. Chromatogr. A. 1531, 64-73 (2018).