Azoxystrobin
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| Azoxystrobin | |
|---|---|
| File:Azoxystrobine.png | |
| File:Azoxystrobin-from-xtal-3D-balls.png | |
| Methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyacrylate | |
| Other names Azoxystrobine Heritage Amistar Quadris Bankit | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 131860-33-8 
|
| PubChem | 3034285 |
| ChemSpider | 2298772 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | WFDXOXNFNRHQEC-GHRIWEEIBD |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C22H17N3O5 |
| Molar mass | 403.39 g mol−1 |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Azoxystrobin is a fungicide commonly used in agriculture. The substance is used as an active agent protecting plants and fruit/vegetables from fungal diseases.
Contents
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.
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.
