Editing Strobilurin

'''Strobilurins''' are a group of natural products and their synthetic analogs. A number of strobilurins are used in [[agriculture]] as [[fungicide]]s. They are part of the larger group of [[QoI|Q{{sub|o}}Is]] (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]]''.<ref>{{cite journal |doi=10.1002/cber.19781110806 |title=Antibiotika aus Basidiomyceten, III. Strobilurin a und B, antifungische Stoffwechselprodukte aus Strobilurus tenacellus |year=1978 |last1=Schramm |first1=Georg |last2=Steglich |first2=Wolfgang |last3=Anke |first3=Timm |last4=Oberwinkler |first4=Franz |journal=Chemische Berichte |volume=111 |issue=8 |pages=2779–2784 }}</ref>
Commercial strobilurin fungicides<ref>Peter Jeschke, Matthias Witschel, Wolfgang Krämer, Ulrich Schirmer (eds.): ''Modern Crop Protection Compounds'', 3rd edition, Wiley-VCH, 2019, {{ISBN|978-3-527-34089-7}}.</ref> were developed through optimization of photostability and activity.<ref>{{cite journal |doi=10.1002/(SICI)1521-3773(19990517)38:10<1328::AID-ANIE1328>3.0.CO;2-1 |title=Strobilurins: Evolution of a New Class of Active Substances |year=1999 |last1=Sauter |first1=Hubert |last2=Steglich |first2=Wolfgang |last3=Anke |first3=Timm |journal=Angewandte Chemie International Edition |volume=38 |issue=10 |pages=1328–1349 |pmid=29711574 }}</ref>
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.<ref>
{{Cite journal
 | title = Activity of Two Strobilurin Fungicides Against Three Species of Decay Fungi in Agar Plate Tests
 | pages = IRG/WP 17-30704
 | author = Juliet D. Tang, Tina Ciaramitaro, Maria Tomaso-Peterson, Susan V. Diehl
  | journal = Proc. IRG Annual Meeting
 | year = 2017}}
([https://www.fpl.fs.fed.us/documnts/pdf2017/fpl_2017_tang001.pdf pdf link])
</ref>
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 [[nutrient]]s; they inhibit [[electron transfer]] in [[mitochondria]], disrupting [[metabolism]] and preventing growth of the target fungi.<ref name=Schaefer>{{cite book |doi=10.1007/978-3-642-54461-3_8 |chapter=Agrochemicals: 8.2 Strobilurins |title=Natural Products in the Chemical Industry |year=2014 |last1=Schaefer |first1=Bernd |pages=688–704 |isbn=978-3-642-54460-6 }}</ref>

==Natural strobilurins==
===Strobilurin A===
:[[Image:Strobilurin A.svg|200px]]
Strobilurin A (also known as mucidin) is produced by ''[[Oudemansiella mucida]]'', ''[[Strobilurus tenacellus]]'', ''[[Bolinea lutea]]'', and others.<ref name=Lorenzen>{{cite journal |last1 =Lorenzen |first1= K.  |last2 =Anke | first2 =T. | year =1998  |title=Basidiomycetes as a Source for New Bioactive Natural Products |url=https://books.google.com/books?id=aI_3BDcYKXgC&pg=PA329  | pages=329–364 |editor-last1=Mori |editor-first1=Kenji |journal=Current Organic Chemistry |volume=2 |issue=4 |doi= 10.2174/1385272802666220128213627 |s2cid= 246934805 |issn=1385-2728 }}</ref><ref name=Anke>{{cite book |doi=10.1007/978-3-662-10378-4_5 |chapter=Non-β-Lactam Antibiotics |title=Industrial Applications |year=2002 |last1=Anke |first1=T. |last2=Erkel |first2=G. |pages=101–104 |isbn=978-3-642-07481-3 }}</ref><ref name="Zakharychev-Kovalenko-1998">{{cite journal | last1=Zakharychev | first1=Vladimir V | last2=Kovalenko | first2=Leonid V | title=Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors | journal=[[Russian Chemical Reviews]] | volume=67 | issue=6 | date=1998-06-30 | issn=0036-021X | doi=10.1070/rc1998v067n06abeh000426 | pages=535–544 | bibcode=1998RuCRv..67..535Z | s2cid=95676421}}</ref> 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.<ref name=Schaefer>{{cite book |doi=10.1007/978-3-642-54461-3_8 |chapter=Agrochemicals: 8.2 Strobilurins |title=Natural Products in the Chemical Industry |year=2014 |last1=Schaefer |first1=Bernd |pages=688–704 |isbn=978-3-642-54460-6 }}</ref>{{rp|694}}
====9-Methoxystrobilurin A====
9-Methoxystrobilurin A is produced by ''Favolaschia'' spp.<ref name=Anke/>
===Strobilurin B===
:[[Image:Strobilurin B.svg|200px]]
Strobilurin B is produced by ''S. tenacellus''.<ref name=Anke/>
===Strobilurin C===
:[[Image:Strobilurin C.svg|220px]]
Strobilurin C is produced by ''[[Xerula longipes|X. longipes]]'' and ''[[Xerula melanotricha|X. melanotricha]]''.<ref name=Anke/><ref name="Zakharychev-Kovalenko-1998" />
===Strobilurin D and G===
:[[Image:Strobilurin D.svg|240px]]
Strobilurin D is produced by ''[[Cyphellopsis anomala]]''.<ref name="Zakharychev-Kovalenko-1998" /> Its structure was originally incorrectly assigned and is now considered to be identical to that of strobilurin G, produced by ''B. lutea''.<ref name=Anke/><ref name="Zakharychev-Kovalenko-1998" /> A related material, hydroxystrobilurin D, with an additional [[hydroxyl]] group attached to the methyl of the main chain is produced by ''[[Mycena sanguinolenta]]''.<ref name=Anke/>
===Strobilurin E===
:[[Image:Strobilurin E.svg|240px]]
Strobilurin E is produced by ''[[Crepidotus fulvotomentosus]]''<ref name="Zakharychev-Kovalenko-1998" /> and ''[[Favolaschia]]'' spp.<ref name=Anke/>
===Strobilurin F2===
:[[Image:Strobilurin F2.svg|240px]]
Strobilurin F2 is produced by ''B. lutea''.<ref name=Lorenzen/>
===Strobilurin H===
:[[Image:Strobilurin H.svg|200px]]
Strobilurin H is produced by ''B. lutea''.<ref name=Anke/> The natural product with a [[phenol]]ic hydroxy group in place of the aromatic methoxy group of strobilurin H is called strobilurin F1 and is found in ''C. anomala''<ref name="Zakharychev-Kovalenko-1998" /> and ''[[Agaricus]] spp.<ref name=Lorenzen/>
===Strobilurin X===
:[[Image:Strobilurin X.svg|200px]]
Strobilurin X is produced by ''O. mucida''.<ref name=Anke/><ref name="Zakharychev-Kovalenko-1998" />
===Oudemansins===
The oudemansins are closely related to the strobilurins and are also quinone outside inhibitors.<ref name=Anke/>
:[[File: Oudemansins general.svg|200px]]
[[Oudemansin A]] with R<sub>1</sub> = R<sub>2</sub> = H was first described in 1979, after being isolated from mycelial fermentations of the [[basidiomycota|basidiomycete]] fungus ''Oudemansiella mucida''.<ref>{{cite journal |doi=10.7164/antibiotics.32.1112 |pmid=528381 |title=Antibiotics from basidiomycetes. IX. Oudemansin, an antifungal antibiotic from Oudemansiella mucida (Schrader ex Fr.) hoehnel (Agaricales) |journal=The Journal of Antibiotics |volume=32 |issue=11 |pages=1112–1117 |year=1979 |last1=Anke |first1=Timm |last2=Hecht |first2=Hans Jürgen |last3=Chramm |first3=Georgs |last4=Steglich |first4=Wolfgang |doi-access=free }}</ref>
Later it was found in cultures of the basidiomycete fungi ''[[Mycena polygramma]]'' and ''Xerula melanotricha''. The latter fungus also produces oudemansin B, with R<sub>1</sub> = MeO and R<sub>2</sub> = Cl. Oudemansin X, with R<sub>1</sub> = H and R<sub>2</sub> = MeO was isolated from ''[[Oudemansiella radicata]]''.<ref name=Lorenzen/>
==Synthetic strobilurins==
The discovery of the strobilurin class of fungicides led to the development of a group of commercial fungicides used in agriculture. Examples are shown below.<ref name=Schaefer/>
<gallery>
Image:Azoxystrobin.svg|{{center|[[Azoxystrobin]]}}
Image:Trifloxystrobin.svg|{{center|[[Trifloxystrobin]]}}
Image:Kresoxim-methyl-2D-skeletal.png|{{center|[[Kresoxim methyl]]}}
Image:Pyraclostrobin.png|{{center|[[Pyraclostrobin]]}}
</gallery>

== See also ==
* [[Plant pathology]]

==References==
{{Reflist}}

== External links ==
<!-- * {{deadlink|date=August 2017}}[http://www.pesticides.gov.uk/rags.asp?id=958 ''Septoria tritici'' resistance to strobilurins in the UK] -->
* {{citation |url=https://beaufort.ces.ncsu.edu/2013/10/frogeye-leaf-spot-resistance-to-strobilurin-fungicides-confirmed-in-beaufort-county/ |title=Resistance to strobilurins in the southern USA |archive-url=https://web.archive.org/web/20190908155341/https://beaufort.ces.ncsu.edu/2013/10/frogeye-leaf-spot-resistance-to-strobilurin-fungicides-confirmed-in-beaufort-county/ |archive-date=2019-09-08 |access-date=2019-09-08 |url-status=live }}
* {{citation |url=http://www.davidmoore.org.uk/21st_Century_Guidebook_to_Fungi_PLATINUM/Ch18_04.htm |title=Agricultural mycocides for the 21st century: strobilurins |archive-url=https://web.archive.org/web/20190908155044/http://www.davidmoore.org.uk/21st_Century_Guidebook_to_Fungi_PLATINUM/Ch18_04.htm |archive-date=2019-09-08 |access-date=2019-09-08 |url-status=live }}, from: David Moore, Geoffrey D. Robson, [[Anthony P. J. Trinci]], ''21st Century Guidebook to Fungi'', 2nd edition.

[[Category:Fungicides]]
[[Category:Respiratory toxins]]
[[Category:Complex III inhibitors]]
[[Category:Strobilurins]]