Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H17N3O5 |
| Molecular Weight | 403.3875 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO\C=C(\C(=O)OC)C1=C(OC2=NC=NC(OC3=C(C=CC=C3)C#N)=C2)C=CC=C1
InChI
InChIKey=WFDXOXNFNRHQEC-GHRIWEEISA-N
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+
Azoxystrobin is the first of a new class of pesticidal
compounds called ß-methoxyacrylates, which are derived from the
naturally-occurring strobilurins. Azoxystrobin is a broad spectrum fungicide with activity against several diseases on many edible crops and ornamental plants. Some diseases controlled or prevented are rice blast, rusts, downy mildew, powdery mildew, late blight, apple scab, and Septoria. Azoxystrobin is marketed by Syngenta as single AS products under several trade names, the major ones for crop protection being: Amistar, Abound, Priori, Quadris, Dynasty for seed treatments, and Heritage for turf. Azoxystrobin (AZOX), a Qo inhibitor of mitochondrial respiratory complex III, exerts whole-body beneficial effects on the regulation of glucose and lipid homeostasis in high-fat diet-fed mice. Chronic treatment with AZOX reduced body weight and significantly improved glucose tolerance and insulin sensitivity in high-fat diet-fed mice. AZOX treatment resulted in decreased triacylglycerol accumulation and down-regulated the expression of genes involved in liver lipogenesis. AZOX increased glucose uptake in L6 myotubes and 3T3-L1 adipocytes and inhibited de novo lipogenesis in HepG2 cells.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2366425 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19928849 |
297.6 nM [Ki] | ||
Target ID: GO:0008121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726979 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of the fungicide azoxystrobin on Atlantic salmon (Salmo salar L.) smolt. | 2010-11 |
|
| Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010-03-15 |
|
| The inducibility of human cytochrome P450 1A by environmental-relevant xenobiotics in the human hepatoma derived cell line HepG2. | 2009-11 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726979
Curator's Comment: Azoxystrobin is non-oncogenic in the rat. Based on a study which administered azoxystrobin in the diets of rats the following values were recorded: male rat 3.6 mg/kg/day, female rat 3.6 mg/kg/day at 60 ppm diet; male rat 18.2 mg/kg/day, female rat 22.3 mg/kg/day at 300 ppm diet; male rat 82.4 mg/kg/day, female rat 117.6 mg/kg/day at 1500/750 ppm diet, respectively. http://pmep.cce.cornell.edu/profiles/extoxnet/24d-captan/azoxystrobin-ext.html
High-fat diet-fed mice were orally administered either vehicle (100% corn oil) or Azoxystrobin (25 mg/kg/day) for 35 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27763520
Azoxystrobin inhibited Botrytis cinerea fungi in vitro with EC50 value of 0.0884 uM.
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EPA PESTICIDE CODE |
128810
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DTXSID0032520
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azoxystrobin
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AZOXYSTROBIN
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ANNEX I INDEX 607-256-00-X
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m2187
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PRIMARY | Merck Index |
SUBSTANCE RECORD