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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:59340 ;
ChEMBL	ChEMBL1812200 ;
ChemSpider	184727 ;
ECHA InfoCard	100.114.714
PubChem CID	213032;
UNII	V1C07OR6II ;
CompTox Dashboard (EPA)	DTXSID8034588 ;
	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 Key: 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 Key: PCCSBWNGDMYFCW-UHFFFAOYAG;
	SMILES 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). verify (what is ?) Infobox references

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 Q_oI, albeit with a chemistry different from most Q_oIs. (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[edit]

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

Resistance management[edit]

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 Q_oIs 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]

References[edit]

^ ^a ^b Famoxadone Pesticide Fact Sheet, United States Environmental Protection Agency
^ Phillip Brannen. "Fungicide resistance management for powdery and downy mildews" (PDF).
^ ^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.
^ ^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.
^ ^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.
^ 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.

External links[edit]

Famoxadone in the Pesticide Properties DataBase (PPDB)

[EPA-1] Famoxadone Pesticide Fact Sheet, United States Environmental Protection Agency

[UGA-ext-2] Phillip Brannen. "Fungicide resistance management for powdery and downy mildews" (PDF).

[Knight-et-al-1997-3] 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.

[Schepers-Cooke-2015-4] ^ ^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.

[FRAC-MoAs-5] 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.

[Cramer-et-al-2006-6] 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.

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