A broad-spectrum fungicide
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Azoxystrobin

Item No. 24056

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-αE-(methoxymethylene)-benzeneacetic acid, methyl ester
CAS Number
131860-33-8
Synonyms
  • ICI-A 5504
Molecular Formula
C22H17N3O5
Formula Weight
403.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly Soluble
SMILES
CO/C=C(C(OC)=O)\C(C=CC=C1)=C1OC2=NC=NC(OC3=C(C#N)C=CC=C3)=C2
InChi Code
InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+
InChi Key
WFDXOXNFNRHQEC-GHRIWEEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $37

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    50 mg

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    100 mg

    $120

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    Cayman Chemical
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    Product Description

    Azoxystrobin is a broad-spectrum β-methoxyacrylate fungicide (LC95s = <1 mg/L for ascomycete, basidiomycete, deuteromycete, and oomycete plant pathogens).1 It inhibits mitochondrial respiration by binding to the Qo site of mitochondrial complex III, also known as cytochrome bc1 complex, and inhibiting electron transfer.2 Azoxystrobin is cytotoxic to MDA-kb2 cells with an EC20 value of 2.9 µM but has no antiandrogenic activity.3 It disrupts mRNA expression of antioxidant-, stress response-, and innate immune-related genes and induces the production of reactive oxygen species (ROS) in zebrafish larva when used at doses ranging from 0.1 to 100 µg/L.4 Azoxystrobin inhibits proliferation of KYSE-150 human esophageal squamous cell carcinoma cells (IC50 = 2.42 µg/ml after 48 hours) and induces apoptosis in a time- and dose-dependent manner.5 In a KYSE-150 nude mouse xenograft model, azoxystrobin reduces tumor growth when administered at a dose of 40 mg/kg per day. Formulations containing azoxystrobin have been used as fungicides in agricultural, aquatic, commercial, industrial, and residential areas.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Godwin, J.R., Anthony, V.M., Clough, J.M., et al. ICI A5504: A novel, broad spectrum, systemic β-methoxyacrylate fungicide. Brit. Crop Prot. Conf. - Pests and Dis., Proc. 1, 435-442 (1992).

    2. Wiggins, T.E., and Jager, B.J. Mode of action of the new methoxyacrylate antifungal agent ICIA5504. Biochem. Soc. Trans. 22(1), 68S (1994).

    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. Jiang, J., Shi, Y., Yu, R., et al. Biological response of zebrafish after short-term exposure to azoxystrobin. Chemosphere 202, 56-64 (2018).

    5. Shi, X.K., Bian, X.B., Huang, T., et al. Azoxystrobin induces apoptosis of human esophageal squamous cell carcinoma KYSE-150 cells through triggering of the mitochondrial pathway. Front. Pharmacol. 8, 277 (2017).