famoxadone
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459444593
| ImageFile = Famoxadone.svg
| ImageSize = 200px
| IUPACName = (RS)-5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione
| OtherNames = Famoxate; FMX
| Section1 = {{Chembox Identifiers
| CASNo = 131807-57-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V1C07OR6II
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 59340
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1812200
| PubChem = 213032
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 184727
| SMILES = O=C2OC(C(=O)N2Nc1ccccc1)(c4ccc(Oc3ccccc3)cc4)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PCCSBWNGDMYFCW-UHFFFAOYSA-N
| InChI = 1/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3
| InChIKey = PCCSBWNGDMYFCW-UHFFFAOYAG
}}
| Section2 = {{Chembox Properties
| C=22|H=18|N=2|O=4
| Appearance =
| Density =
| MeltingPt = 140.3-141.8 °C
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Famoxadone is a fungicide to protect agricultural products against various fungal diseases on fruiting vegetables, tomatoes, potatoes, curcurbits, lettuce and grapes.[http://www.epa.gov/opprd001/factsheets/famoxadone.pdf Famoxadone Pesticide Fact Sheet], United States Environmental Protection Agency It is used in combination with cymoxanil.{{cite web | url=http://site.extension.uga.edu/viticulture/files/2021/02/Pathology-Downy-Powdery-Mildew-Presentation-2021.pdf | title=Fungicide resistance management for powdery and downy mildews | author=Phillip Brannen}} Famoxadone is a QoI, albeit with a chemistry different from most Q{{sub|o}}Is. (It is an oxazolidine-dione while most are strobilurins.){{cite web | url=http://www.frac.info/docs/default-source/publications/frac-code-list/frac-code-list-2021--final.pdf | title=FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels) | date=March 2021 | author=FRAC (Fungicide Resistance Action Committee) | pages=1–17 | access-date=2021-07-12 | archive-date=2021-11-05 | archive-url=https://web.archive.org/web/20211105005300/https://www.frac.info/docs/default-source/publications/frac-code-list/frac-code-list-2021--final.pdf | url-status=dead }} It is commonly used against Plasmopara viticola, Alternaria solani,{{cite book | editor=Ishii H., Hollomon D. | last=Schepers | first=Huub T. A. M. | last2=Cooke | first2=Louise R. | title=Fungicide Resistance in Plant Pathogens | chapter=Potato Pathogens in Northern and Western Europe | publisher=Springer Japan | publication-place=Tokyo | year=2015 | isbn=978-4-431-55641-1 | pages=355–378}} Phytophthora infestans, and Septoria nodorum.{{cite journal | last=Knight | first=S. C. | last2=Anthony | first2=V. M. | last3=Brady | first3=A. M. | last4=Greenland | first4=A. J. | last5=Heaney | first5=S. P. | last6=Murray | first6=D. C. | last7=Powell | first7=K. A. | last8=Schulz | first8=M. A. | last9=Spinks | first9=C. A. | last10=Worthington | first10=P. A. | last11=Youle | first11=D. | title=Rationale and Perspectives on the Development of Fungicides | journal=Annual Review of Phytopathology | publisher=Annual Reviews | volume=35 | issue=1 | year=1997 | issn=0066-4286 | doi=10.1146/annurev.phyto.35.1.349 | pages=349–372}}
Molecular interaction
Famoxadone is of lesser interaction strength at the Qp pocket than some other Q{{sub|o}}Is, for example, azoxystrobin. This is because azoxystrobin and such interact more centrally in the Q{{sub|p}} pocket than does famoxadone.{{cite journal | last=Cramer | first=William A. | last2=Zhang | first2=Huamin | last3=Yan | first3=Jiusheng | last4=Kurisu | first4=Genji | last5=Smith | first5=Janet L. | title=Transmembrane Traffic in the Cytochrome b{{sub|6}}f Complex | journal=Annual Review of Biochemistry | publisher=Annual Reviews | volume=75 | issue=1 | year=2006 | issn=0066-4154 | doi=10.1146/annurev.biochem.75.103004.142756 | pages=769–790}}
Resistance management
Although it has a different chemistry, famoxadone shows full cross-resistance with the rest of the main FRAC group 11 that it belongs to, which is almost entirely strobs. It has not shown cross-resistance with the 11A subgroup however. As with all Q{{sub|o}}Is there is a high risk of resistance development and so pesticide stewardship is important.
Populations of P. infestans and A. solani in northern and western Europe are not known to be resistant to famoxadone.
Great Britain approval withdrawn
On June 30 2024, approval for famoxadone's use in Great Britain was withdrawn by the Health and Safety Executive due to the risk it presents to birds.{{cite web | url = https://content.govdelivery.com/accounts/UKHSE/bulletins/3abe862 | title = Expiry of the approval of the active substance famoxadone | date = August 7, 2024 | work = Pesticides: expiry of the approval of active substances | publisher = Health and Safety Executive }} Its use was already banned in the European Union, and there was in 2024 concern about the levels of allowed residue particularly on table grapes being too high.{{cite web | url = https://www.efsa.europa.eu/en/efsajournal/pub/7932 | title = Targeted risk assessment for famoxadone | date = March 9, 2023 | publisher = European Food Safety Authority }}
References
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