Azoxystrobin

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Azoxystrobin
Azoxystrobin.svg
Azoxystrobin-from-xtal-3D-balls.png
Identifiers
CAS number 131860-33-8 YesY
PubChem 3034285
ChemSpider 2298772 YesY
DrugBank DB07401
KEGG C18558 YesY
ChEBI CHEBI:40909 N
ChEMBL CHEMBL230001 YesY
Jmol-3D images Image 1
Properties
Molecular formula C22H17N3O5
Molar mass 403.39 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Azoxystrobin (brand name Amistar, Syngenta) is a fungicide commonly used in agriculture. The substance is used as an active agent protecting plants and fruit/vegetables from fungal diseases.

Origin[edit]

Azoxystrobin was discovered during research on Oudemansiella mucida and Strobilurus tenacellus, which are small white or brown coloured mushrooms commonly found in European 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 kill them when in range. Observations of this mechanism led to research that resulted in the development of azoxystrobin.

Activity[edit]

After synthesizing experimental analogs of both substances (over 1400 were tested), azoxystrobin was found to be the most active and stable combination. The toxophore of azoxystrobin is the β-methoxyacrylate portion (shown in blue), which is present in the active compounds from both Oudemansiella mucida and Strobilurus tenacellus:[1]

Structures of the natural defense molecules strobilurin A and oudemansin A and the synthetic fungicide azoxystrobin. The common structural fragment responsible for the activity (toxophore) is highlighted in blue

Azoxystrobin binds very tightly to the Qo site of Complex III of the mitochondrial electron transport chain, thereby ultimately preventing the generation of ATP.

Efficacy[edit]

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

Examples[edit]

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

Practical use[edit]

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

Ecotoxicology[edit]

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

Azoxystrobin is broken down into the soil. Its toxicity is low for mammals, birds, bees, insects, and earthworms. "Azoxystrobin is classified as very toxic to aquatic organisms and [its main degradation product] R234886 as very harmful. [A recent] study shows that azoxystrobin and R234886 can leach through loamy soils for a long period of time following application of the pesticide and thereby pose a potential threat to vulnerable aquatic environments and drinking water resources." [2]

Food Residues[edit]

In recent surveillance by the New Zealand Ministry for Primary Industries, 6 out of 24 olive oil samples contained residues of azoxystrobin or the fungicide propiconazole in excess of the maximum residue limit (MRL) set for agricultural chemicals. "When the processing factor is taken into account, these results indicate that the raw olives would have likely breached the MRLs for those compounds." In the Ministry's judgement, this violation did not pose health or food safety concerns.[3]

External links[edit]

References[edit]

  1. ^ Armstrong, Sarah; Clough, John (March 2009). "Crop Protection Chemicals". Education in Chemistry 46 (2). Retrieved 12 December 2012. 
  2. ^ Jørgensen, Lisbeth Flindt; Jeanne Kjær; Preben Olsen; Annette Elisabeth Rosenbom (July 2012). "Leaching of azoxystrobin and its degradation product R234886 from Danish agricultural field sites". Chemosphere 88 (5): 554–562. doi:10.1016/j.chemosphere.2012.03.027. 
  3. ^ Meister, Miriam (20 August 2012). "More good news on agricultural chemical good practice". Ministry for Primary Industries. Retrieved 23 November 2012.