Fenpicoxamid

Last updated
Fenpicoxamid
Fenpicoxamid v2.svg
Names
IUPAC name
[2-[[(3S,7R,8R,9S)-7-Benzyl-9-methyl-8-(2-methylpropanoyloxy)-2,6-dioxo-1,5-dioxonan-3-yl]carbamoyl]-4-methoxypyridin-3-yl]oxymethyl 2-methylpropanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 815-084-1
PubChem CID
UNII
  • InChI=1S/C31H38N2O11/c1-17(2)28(35)42-16-41-26-23(39-6)12-13-32-24(26)27(34)33-22-15-40-30(37)21(14-20-10-8-7-9-11-20)25(19(5)43-31(22)38)44-29(36)18(3)4/h7-13,17-19,21-22,25H,14-16H2,1-6H3,(H,33,34)/t19-,21+,22-,25-/m0/s1
    Key: QGTOTYJSCYHYFK-RBODFLQRSA-N
  • C[C@H]1[C@@H]([C@H](C(=O)OC[C@@H](C(=O)O1)NC(=O)C2=NC=CC(=C2OCOC(=O)C(C)C)OC)CC3=CC=CC=C3)OC(=O)C(C)C
Properties
C31H38N2O11
Molar mass 614.648 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H373, H410
P260, P273, P319, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fenpicoxamid is a picolinamide fungicide used to control fungal pathogens in cereal crops, particularly Zymoseptoria tritici in wheat. [1] [2] It is derived from a naturally occurring substance called UK-2A produced by a Streptomyces bacteria and is structurally related to the piscicide antimycin A. When absorbed by fungi or plants it is converted to UK-2A. [3] It was authorised for use in the United Kingdom in 2021 and by 2022 was used on 670,000 hectares. [4] [5]

References

  1. ↑ Owen, W John; Yao, Chenglin; Myung, Kyung; Kemmitt, Greg; Leader, Andrew; Meyer, Kevin G; Bowling, Andrew J; Slanec, Thomas; Kramer, Vincent J (October 2017). "Biological characterization of fenpicoxamid, a new fungicide with utility in cereals and other crops". Pest Management Science. 73 (10): 2005–2016. Bibcode:2017PMSci..73.2005O. doi:10.1002/ps.4588. PMC   5599960 . PMID   28471527.
  2. ↑ Leader, A. "Fenpicoxamid, a new natural product derived fungicide for control of Zymoseptoria tritici (Septoria tritici blotch) and other diseases in cereals". Proceedings Crop Production in Northern Britain 2018. Retrieved 23 February 2025.
  3. ↑ Young, David H; Wang, Nick X; Meyer, Stacy T; Avila-Adame, Cruz (February 2018). "Characterization of the mechanism of action of the fungicide fenpicoxamid and its metabolite UK-2A". Pest Management Science. 74 (2): 489–498. Bibcode:2018PMSci..74..489Y. doi:10.1002/ps.4743. PMC   5813142 . PMID   28960782.
  4. ↑ Curtis, Marianne (31 March 2021). "Fungicide with Inatreq active gains UK approval | Farm News | Farmers Guardian". www.farmersguardian.com. Retrieved 23 February 2025.
  5. ↑ "PESTICIDE USAGE SURVEY REPORT 309". Pusstats. FERA. Retrieved 23 February 2025.
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