Fomesafen

Fomesafen
Names
	IUPAC name 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-methylsulfonyl-2-nitrobenzamide
Identifiers
CAS Number	72178-02-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81925;
ChEMBL	ChEMBL1898629;
ChemSpider	46694;
ECHA InfoCard	100.069.470
EC Number	276-439-9;
KEGG	C18736;
PubChem CID	51556;
UNII	M0A3U4CDTF;
CompTox Dashboard (EPA)	DTXSID7024112 ;
	InChI InChI=1S/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22) Key: BGZZWXTVIYUUEY-UHFFFAOYSA-N;
	SMILES CS(=O)(=O)NC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-];
Properties
Chemical formula	C15H10ClF3N2O6S
Molar mass	438.76 g·mol−1
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302
GHS precautionary statements	P264, P270, P301+312, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Fomesafen is an herbicide which acts by inhibiting the enzyme protoporphyrinogen oxidase[1] which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen,[1][2] via metabolic disposal by glutathione S-transferase.[1][2] As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types.[3] It is not safe for maize/corn[4] or other Poaceae.[2]

Resistance

Resistance to fomesafen has developed including in Amaranthus retroflexus in Northeast China,[5] Palmer amaranth in Arkansas,[6] and Euphorbia heterophylla in Brazil.[7]

References

"fomesafen". Weed Ecology and Management Laboratory at Cornell University. Retrieved 2020-11-22.
Andrews, Christopher J.; Skipsey, Mark; Townson, Jane K.; Morris, Carol; Jepson, Ian; Edwards, Robert (1997). "Glutathione transferase activities toward herbicides used selectively in soybean". Pesticide Science. Wiley. 51 (2): 213–222. doi:10.1002/(sici)1096-9063(199710)51:2<213::aid-ps622>3.0.co;2-l. ISSN 0031-613X.
"Registration Review Label Mitigation for Fomesafen" (PDF). United States Environmental Protection Agency.
"Fomesafen Carryover Injury to Corn". Iowa State University. 2014-06-03. Retrieved 2020-11-22.
Huang, Zhaofeng; Cui, Hailan; Wang, Chunyu; Wu, Tong; Zhang, Chaoxian; Huang, Hongjuan; Wei, Shouhui (2020). "Investigation of resistance mechanism to fomesafen in Amaranthus retroflexus L.". Pesticide Biochemistry and Physiology. Elsevier. 165: 104560. doi:10.1016/j.pestbp.2020.104560. ISSN 0048-3575. PMID 32359536.
Salas, Reiofeli A; Burgos, Nilda R; Tranel, Patrick J; Singh, Shilpa; Glasgow, Les; Scott, Robert C; Nichols, Robert L (2016). "Resistance to PPO‐inhibiting herbicide in Palmer amaranth from Arkansas". Pest Management Science. Wiley-Blackwell. 72 (5): 864–869. doi:10.1002/ps.4241. ISSN 1526-498X. PMC 5069602. PMID 26817647.
Brusamarello, Antonio P.; Oliveira, Paulo H.; Trezzi, Michelangelo M.; Finatto, Taciane; Pagnoncelli, Fortunato D. B.; Vidal, Ribas A. (2020). "Inheritance of fomesafen and imazethapyr resistance in a multiple herbicide‐resistant Euphorbia heterophylla population". Weed Research. Wiley. 60 (4): 278–286. doi:10.1111/wre.12425. ISSN 0043-1737.

External links

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[Weed-Ecology-Cornell-1] "fomesafen". Weed Ecology and Management Laboratory at Cornell University. Retrieved 2020-11-22.

[Andrews-et-al-1997-2] Andrews, Christopher J.; Skipsey, Mark; Townson, Jane K.; Morris, Carol; Jepson, Ian; Edwards, Robert (1997). "Glutathione transferase activities toward herbicides used selectively in soybean". Pesticide Science. Wiley. 51 (2): 213–222. doi:10.1002/(sici)1096-9063(199710)51:2<213::aid-ps622>3.0.co;2-l. ISSN 0031-613X.

[EPA-approval-1.88-3] "Registration Review Label Mitigation for Fomesafen" (PDF). United States Environmental Protection Agency.

[Iowa-State-IPM-4] "Fomesafen Carryover Injury to Corn". Iowa State University. 2014-06-03. Retrieved 2020-11-22.

[Huang-et-al-2020-5] Huang, Zhaofeng; Cui, Hailan; Wang, Chunyu; Wu, Tong; Zhang, Chaoxian; Huang, Hongjuan; Wei, Shouhui (2020). "Investigation of resistance mechanism to fomesafen in Amaranthus retroflexus L.". Pesticide Biochemistry and Physiology. Elsevier. 165: 104560. doi:10.1016/j.pestbp.2020.104560. ISSN 0048-3575. PMID 32359536.

[Salas-et-al-2016-6] Salas, Reiofeli A; Burgos, Nilda R; Tranel, Patrick J; Singh, Shilpa; Glasgow, Les; Scott, Robert C; Nichols, Robert L (2016). "Resistance to PPO‐inhibiting herbicide in Palmer amaranth from Arkansas". Pest Management Science. Wiley-Blackwell. 72 (5): 864–869. doi:10.1002/ps.4241. ISSN 1526-498X. PMC 5069602. PMID 26817647.

[Brusamarello-et-al-2020-7] Brusamarello, Antonio P.; Oliveira, Paulo H.; Trezzi, Michelangelo M.; Finatto, Taciane; Pagnoncelli, Fortunato D. B.; Vidal, Ribas A. (2020). "Inheritance of fomesafen and imazethapyr resistance in a multiple herbicide‐resistant Euphorbia heterophylla population". Weed Research. Wiley. 60 (4): 278–286. doi:10.1111/wre.12425. ISSN 0043-1737.