An internal standard for the quantification of tebuconazole
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Unlabeled Version(s)
24052Tebuconazole
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Tebuconazole-d9

Item No. 33287

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-[2-(4-chlorophenyl)ethyl]-α-(1,1-dimethylethyl-d9)-1H-1,2,4-triazole-1-ethanol
CAS Number
1246818-83-6
Molecular Formula
C16H13ClD9N3O
Formula Weight
316.9
Purity
≥99% deuterated forms (d1-d9)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: solubleDMSO: solubleMethanol: soluble
SMILES
ClC(C=C1)=CC=C1CCC(C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])(O)CN2C=NC=N2
InChi Code
InChI=1S/C16H22ClN3O/c1-15(2,3)16(21,10-20-12-18-11-19-20)9-8-13-4-6-14(17)7-5-13/h4-7,11-12,21H,8-10H2,1-3H3/i1D3,2D3,3D3
InChi Key
PXMNMQRDXWABCY-GQALSZNTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tebuconazole-d9 is intended for use as an internal standard for the quantification of tebuconazole (Item No. 24052) by GC- or LC-MS. Tebuconazole is a triazole fungicide that is active against both seed and foliar fungi.1 It inhibits 14α-demethylase isolated from U. maydis and S. bicolor with IC50 values of 0.05 and 0.16 nM, respectively.2 It inhibits the androgenic effect of the androgen receptor agonist DHT (IC20 = 2.89 µM) and is cytotoxic (EC20 = 38.9 µM) in an MDA-kb2 assay.3 Tebuconazole (50 and 100 mg/kg per day) administered during gestation reduces testosterone levels and increases testicular levels of progesterone and 17α-hydroxyprogesterone in male rat fetuses.4 It has a feminizing effect on male pups and a virilizing effect on female pups. When administered to rats gestationally through postnatal day 42, tebuconazole (20 and 60 mg/kg per day) leads to cell death of pyramidal cells in the CA3-4 region of the hippocampus and layer V of the cortex concomitant with impairment in learning the platform location in the Morris water maze.5 Formulations containing tebuconazole have been used as preservatives for wood and other materials, as well as fungicides in agricultural, commercial, industrial, and residential areas.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reinecke, P., Kaspers, H., Scheinpflug, H., et al. BAY HWG 1608, a new fungicide for foliar spray and seed-treatment use against a wide spectrum of fungal pathogens. Br. Crop Prot. Conf.--Pests Dis., Proc. 1, 41-46 (1986).

    2. Zarn, J.A., Brüschweiler, B.J., and Schlatter, J.R. Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 α-demethylase and aromatase. Environ. Health Perspect. 111(3), 255-261 (2003).

    3. Orton, F., Rosivatz, E., Scholze, M., et al. Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens. Environ. Health Perspect. 119(6), 794-800 (2011).

    4. Taxvig, C., Hass, U., Axelstad, M., et al. Endocrine-disrupting activities in vivo of the fungicides tebuconazole and epoxiconazole. Toxicol. Sci. 100(2), 464-473 (2007).

    5. Moser, V.C., Barone, S., Jr., Smialowicz, R.J., et al. The effects of perinatal tebuconazole exposure on adult neurological, immunological, and reproductive function in rats. Toxicol. Sci. 62(2), 339-352 (2001).