A triazole fungicide
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Bitertanol

Item No. 24054

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
β-([1,1'-biphenyl]-4-yloxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol
CAS Number
55179-31-2
Synonyms
  • Biloxazol
Molecular Formula
C20H23N3O2
Formula Weight
337.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightl solubleDMSO: Slightly SolubleMethanol: Slightly Soluble
SMILES
OC(C(C)(C)C)C(N1N=CN=C1)OC(C=C2)=CC=C2C3=CC=CC=C3
InChi Code
InChI=1S/C20H23N3O2/c1-20(2,3)18(24)19(23-14-21-13-22-23)25-17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-14,18-19,24H,1-3H3
InChi Key
VGPIBGGRCVEHQZ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $107

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    500 mg

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    1 g

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    Cayman Chemical
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    Product Description

    Bitertanol is a broad-spectrum triazole fungicide that is active against a variety of fungi, including V. inaequalis and V. pirina, which are responsible for apple and pear scab, respectively, as well as S. mors-uvae and P. ribis, which are responsible for American gooseberry mildew and leaf spot in black currants, respectively.1 It is active against isolates of V. inaequalis (MICs = 0.6 and 1 µg/ml) but repeated use leads to resistance and cross-resistance (MICs = 9.8-13 µg/ml for bitertanol-resistant isolates).2 Bitertanol inhibits the cytochrome P450 (CYP450) isoform CYP3A4 (IC50 = 2.74 µM) and inhibits androgenic activity induced by the androgen receptor agonist DHT (Item No. 15874) in a yeast two-hybrid assay (IC50 = 79.85 µM).3 In rats, bitertanol (10-300 mg/kg, i.p.) increases operant responding on one- and five-minute fixed interval schedules with no effect on motor activity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Birch, P.A., Rose, P.W., and Wainwright, A. A broad spectrum fungicide of the triazole group for use in pome and bush fruit. Brit. Crop Prot. Conf. - Pests and Dis., Proc. 11(2), 545-554 (1981).

    2. Hildebrand, P.D., Lockhart, C.L., Newberry, R.J., et al. Resistance of Venturia inaequalis to bitertanol and other demethylation-inhibiting fungicides. Can. J. Plant Path. 10(4), 311-316 (1988).

    3. Lv, X., Pan, L., Wang, J., et al. Effects of triazole fungicides on androgenic disruption and CYP3A4 enzyme activity. Environ. Pollut. 222(2016), 504-512 (2017).

    4. Allen, A.R., and MacPhail, R.C. Bitertanol, a triazole fungicide, increases operant responding but not motor activity. Neurotoxicol. Teratol. 15(4), 237-242 (1993).