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Concept
Strobilurin
Summary
Strobilurins are a group of natural products and their synthetic analogs. A number of strobilurins are used in agriculture as fungicides. They are part of the larger group of Q_oIs (Quinone outside Inhibitors), which act to inhibit the respiratory chain at the level of Complex III.
The first parent natural products, strobilurins A and B, were extracted from the fungus Strobilurus tenacellus.
Commercial strobilurin fungicides were developed through optimization of photostability and activity.
Strobilurins represented a major development in fungus-based fungicides. First released in 1996, there are now ten major strobilurin fungicides on the market, which account for 23-25 % of the global fungicide sales.
Examples of commercialized strobilurin derivatives are azoxystrobin, kresoxim-methyl, picoxystrobin, fluoxastrobin, oryzastrobin, dimoxystrobin, pyraclostrobin and trifloxystrobin.
Strobilurins are mostly contact fungicides with a long half time as they are absorbed into the cuticle and not transported any further. They have a suppressive effect on other fungi, reducing competition for nutrients; they inhibit electron transfer in mitochondria, disrupting metabolism and preventing growth of the target fungi.
Strobilurin A (also known as mucidin) is produced by Oudemansiella mucida, Strobilurus tenacellus, Bolinea lutea, and others. When first isolated it was incorrectly assigned as the E E E geometric isomer but was later identified by total synthesis as being the E Z E isomer, as shown.
9-Methoxystrobilurin A is produced by Favolaschia spp.
Strobilurin B is produced by S. tenacellus.
Strobilurin C is produced by X. longipes and X. melanotricha.
Strobilurin D is produced by Cyphellopsis anomala. Its structure was originally incorrectly assigned and is now considered to be identical to that of strobilurin G, produced by B. lutea. A related material, hydroxystrobilurin D, with an additional hydroxyl group attached to the methyl of the main chain is produced by Mycena sanguinolenta.
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