Azoxystrobin

{{chembox | verifiedrevid = 401811205 |ImageFile=Azoxystrobine.png |ImageSize=220px |ImageFile1=Azoxystrobin-from-xtal-3D-balls.png |ImageSize1=220px |IUPACName=Methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyacrylate |OtherNames=Azoxystrobine
Heritage
Amistar
Quadris
Bankit |Section1= ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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CAS Number

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• 131860-33-8 ^Y

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3D model (JSmol)

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• Interactive image

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| ChemSpider

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• 2298772 ^Y

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| ECHA InfoCard | 100.127.964 |-

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PubChem CID

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• 3034285

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CompTox Dashboard (EPA)

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• DTXSID0032520

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InChI

• 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+ ^Y

  Key: WFDXOXNFNRHQEC-GHRIWEEISA-N ^Y
• InChI=1/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+

  Key: WFDXOXNFNRHQEC-GHRIWEEIBD

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SMILES

• O=C(OC)\C(=C\OC)c3ccccc3Oc2ncnc(Oc1c(C#N)cccc1)c2

|- |Section2= ! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

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Chemical formula

| C₂₂H₁₇N₃O₅

|- | Molar mass

| 403.388

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Azoxystrobin is a fungicide commonly used in agriculture. The substance is used as an active agent protecting plants and fruit/vegetables from fungal diseases.

Origin

Azoxystrobin was discovered during research on Oudemansiella mucida and Strobilurus tenacellus, which are small white or brown coloured mushrooms commonly found in the Czech forests. Not bigger than a few centimeters, these mushrooms attracted attention of scientists because of their remarkable ability to defend themselves. Their defense mechanism is based on the secretion of two substances, strobilurin A and oudemansin A. These substances allow them to keep their competitors at a distance and even destroy them when in range. Observations of this mechanism led directly to research that resulted in azoxystrobin.

Activity

After synthesizing experimental analogs of both substances (over 1400 were tested), azoxystrobin was found to be the most active and stable combination. The pharmacophore of azoxystrobine is the β-methoxyacrylate portion, which is present in the active compounds from both Oudemansiella mucida and Strobilurus tenacellus. Azoxystrobin binds very tightly to the Qo site of Complex III of the mitochondrial electron transport chain, thereby ultimately preventing the generation of ATP.

Efficiency

Azoxystrobin possesses the broadest spectrum of activity of all presently known antifungals. It is presently the only counteragent that has the ability to protect against the 4 big groups of fungal diseases:

• Ascomycota: Septoria
• Deuteromycota: Pyricularia (rice harvesting)
• Basidiomycota: Stripe rust
• Oomycota: Water mould (grape harvesting)

Examples

Azoxystrobin is widely used in farming, particularly in wheat farming. Applying agents containing azoxystrobin provides protection against many types of diseases, including:

• Wheat septoria
• Septoria leaf spot
• Wheat leaf rust (Puccinia recondita)
• Rye leafrust (Puccinia triticina)
• Powdery mildew
• Downy mildew
• Stripe rust
• Haustorium
• Pyrenophora teres

Practical use

• Grain farming
• Banana transport
• grapes, both table & wine

Ecotoxicology

Azoxystrobin has a favorable ecotoxicological profile, meeting the expectations of agricultural demand.

Its toxicity is low for mammals, birds, bees, insects, and earthworms. It is highly toxic for freshwater fish and invertebraes and very highly toxic for marine invertebraes. (this is disputed. Please read discussion page for details)

Azoxystrobin is broken down into the soil. The agent is not very mobile and therefore is unlikely to penetrate further in the soil and come into contact with groundwater.

External links

• National Pesticide Information Center
• Pesticide fact sheet
• Crop Protection Database: Learn more about azoxystrobin