Famoxadone

Famoxadone
Names
IUPAC name
(RS)-5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione
Other names
Famoxate; FMX
Identifiers
CAS Number
  • 131807-57-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:59340 checkY
ChEMBL
  • ChEMBL1812200 ☒N
ChemSpider
  • 184727 checkY
ECHA InfoCard 100.114.714 Edit this at Wikidata
PubChem CID
  • 213032
UNII
  • V1C07OR6II checkY
CompTox Dashboard (EPA)
  • DTXSID8034588 Edit this at Wikidata
InChI
  • InChI=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 checkY
    Key: PCCSBWNGDMYFCW-UHFFFAOYSA-N checkY
  • 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
    Key: PCCSBWNGDMYFCW-UHFFFAOYAG
  • O=C2OC(C(=O)N2Nc1ccccc1)(c4ccc(Oc3ccccc3)cc4)C
Properties
Chemical formula
 C22H18N2O4
Molar mass 374.396 g·mol−1
Melting point 140.3-141.8 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Famoxadone is a fungicide to protect agricultural products against various fungal diseases on fruiting vegetables, tomatoes, potatoes, curcurbits, lettuce and grapes.[1] It is used in combination with cymoxanil.[1][2] Famoxadone is a QoI, albeit with a chemistry different from most QoIs. (It is an oxazolidine-dione while most are strobilurins.)[3][4][5] It is commonly used against Plasmopara viticola,[3] Alternaria solani,[3][4] Phytophthora infestans,[3][4] and Septoria nodorum.[3][4]

Molecular interaction

Famoxadone is of lesser interaction strength at the Qp pocket than some other QoIs, for example, azoxystrobin. This is because azoxystrobin and such interact more centrally in the Qp pocket than does famoxadone.[6]

Resistance management

Although it has a different chemistry, famoxadone shows full cross-resistance with the rest of the main FRAC group 11[4] that it belongs to, which is almost entirely strobs. It has not shown cross-resistance with the 11A subgroup however. As with all QoIs there is a high risk of resistance development and so pesticide stewardship is important.[5][4]

Populations of P. infestans and A. solani in northern and western Europe are not known to be resistant to famoxadone.[4]

Great Britain approval withdrawn

On June 30 2024, approval for famoxadone's use in Great Britain was withdrawn by the Health and Safety Executive due to the risk it presents to birds.[7] Its use was already banned in the European Union, and there was in 2024 concern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.[8]

References

  1. ^ a b Famoxadone Pesticide Fact Sheet, United States Environmental Protection Agency
  2. ^ Phillip Brannen. "Fungicide resistance management for powdery and downy mildews" (PDF).
  3. ^ a b c d e Knight, S. C.; Anthony, V. M.; Brady, A. M.; Greenland, A. J.; Heaney, S. P.; Murray, D. C.; Powell, K. A.; Schulz, M. A.; Spinks, C. A.; Worthington, P. A.; Youle, D. (1997). "Rationale and Perspectives on the Development of Fungicides". Annual Review of Phytopathology. 35 (1). Annual Reviews: 349–372. doi:10.1146/annurev.phyto.35.1.349. ISSN 0066-4286.
  4. ^ a b c d e f g Schepers, Huub T. A. M.; Cooke, Louise R. (2015). "Potato Pathogens in Northern and Western Europe". In Ishii H., Hollomon D. (ed.). Fungicide Resistance in Plant Pathogens. Tokyo: Springer Japan. pp. 355–378. ISBN 978-4-431-55641-1.
  5. ^ a b FRAC (Fungicide Resistance Action Committee) (March 2021). "FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels)" (PDF). pp. 1–17. Archived from the original (PDF) on 2021-11-05. Retrieved 2021-07-12.
  6. ^ Cramer, William A.; Zhang, Huamin; Yan, Jiusheng; Kurisu, Genji; Smith, Janet L. (2006). "Transmembrane Traffic in the Cytochrome b6f Complex". Annual Review of Biochemistry. 75 (1). Annual Reviews: 769–790. doi:10.1146/annurev.biochem.75.103004.142756. ISSN 0066-4154.
  7. ^ "Expiry of the approval of the active substance famoxadone". Pesticides: expiry of the approval of active substances. Health and Safety Executive. August 7, 2024.
  8. ^ "Targeted risk assessment for famoxadone". European Food Safety Authority. March 9, 2023.
  • Famoxadone in the Pesticide Properties DataBase (PPDB)