Icafolin-methyl

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Icafolin-methyl
Skeletal formulae of icafolin-methyl stereoisomers Icafolin-methyl.svg
Skeletal formulae of icafolin-methyl stereoisomers
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
3D model (JSmol)
ChEMBL
PubChem CID
  • 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
  • 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
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).

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]

References

  1. ↑ Young, Cyndi. "Bayer Unveils Icafolin and Conventro: New Herbicide Technologies Target Resistant Weeds and Support Sustainable Farming". Brownfield Ag News. Retrieved January 6, 2026.
  2. 1 2 "Icafolin-methyl". PubChem . National Center for Biotechnology Information . Retrieved January 6, 2026.
  3. ↑ "Icafolin-methyl". Pesticide Properties DataBase. University of Hertfordshire. November 9, 2025. Retrieved January 6, 2026.
  4. ↑ Marston, Jennifer (September 30, 2025). "Icafolin-methyl 'a completion of glyphosate,' not a replacement: in conversation with Bayer". AgFunderNews. Retrieved January 6, 2026.
  5. ↑ "Bayer should launch two herbicides in the coming years: icafolin and Convintro Duo". Revista Cultivar. January 2, 2024. Archived from the original on June 14, 2025. Retrieved January 6, 2026.
  6. ↑ Haaf, Klaus-Bernhard; Peters, Olaf; Laber, Bernd; Lange, Gudrun; Gatzweiler, Elmar; Geibel, Sven; Passon, Daniel; Endler, Anne; Lange, Sylvia; Kahlau, Sabine; Eroschenko, Tatjana; Waldraff, Petra; Lümmen, Peter (2025). "The novel herbicide icafolin-methyl is a plant-specific inhibitor of tubulin polymerization". Pest Management Science. 81 (5): 2652–2661. doi:10.1002/ps.8415. ISSN   1526-4998. PMID   39297346.


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