Icafolin-methyl

Icafolin-methyl is a post-emergent chemical herbicide developed by Bayer.^[1] It is a methyl ester derivative of icafolin and has the formula C₁₈H₁₈F₂N₂O₅.^[2] The herbicide was patented in 2022,^[3] registered in 2025, and is anticipated to be introduced in 2028 for use in Brazil.^[4] It is a tubulin inhibitor that may be applied to cereals, oilseeds and soybeans, and is described as being effective against monocotyledonous and dicotyledonous weeds, with examples being sourgrass and barnyardgrass.^[5] The herbicide is synthesized as a mixture of (2R,4R) and (2S,4S) stereoisomers through a multi-step process.^[2] Icafolin-methyl is hydrolyzed to icafolin in plants.^[6]

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Icafolin-methyl

Names
Preferred IUPAC name methyl (2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl-4H-1,2-oxazole-5-carbonyl]amino]oxolane-2-carboxylate
Identifiers
CAS Number	2254752-21-9
3D model (JSmol)	Interactive image
ChemSpider	133326948
PubChem CID	146479070
InChI InChI=1S/C18H18F2N2O5/c1-3-18(17(24)21-13-7-15(26-9-13)16(23)25-2)8-14(22-27-18)10-4-11(19)6-12(20)5-10/h3-6,13,15H,1,7-9H2,2H3,(H,21,24)/t13?,15?,18-/m1/s1 Key: TVMYHMXZYVGODK-LEHRNKBSSA-N
SMILES FC=1C=C(C=C(C1)F)C1=NO[C@@](C1)(C=C)C(=O)N[C@@H]1C[C@@H](OC1)C(=O)OC
Properties
Chemical formula	C18H18F2N2O5
Molar mass	380.348 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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