Oxathiapiprolin

Oxathiapiprolin
Names
Preferred IUPAC name
12,16-Difluoro-75-methyl-73-(trifluoromethyl)-24,25-dihydro-4(4,1)-piperidina-2(5,3)-[1,2]oxazola-3(4,2)-[1,3]thiazola-7(1)-pyrazola-1(1)-benzenaheptaphan-5-one
Identifiers
3D model (JSmol)
20731698
ChEBI
ChemSpider
ECHA InfoCard 100.227.885 Edit this at Wikidata
EC Number
  • 801-263-1
UNII
  • InChI=1S/C24H22F5N5O2S/c1-13-9-20(24(27,28)29)31-34(13)11-21(35)33-7-5-14(6-8-33)23-30-18(12-37-23)17-10-19(36-32-17)22-15(25)3-2-4-16(22)26/h2-4,9,12,14,19H,5-8,10-11H2,1H3
    Key: IAQLCKZJGNTRDO-UHFFFAOYSA-N
  • CC1=CC(=NN1CC(=O)N2CCC(CC2)C3=NC(=CS3)C4=NOC(C4)C5=C(C=CC=C5F)F)C(F)(F)F
Properties
C24H22F5N5O2S
Molar mass 539.53 g·mol−1
Density 1.4645 g/cm3
Melting point 146 to 148 °C (295 to 298 °F; 419 to 421 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oxathiapiprolin (trade names Orondis, Zorvec, and Segovis) is a fungicide. In the United States, the Environmental Protection Agency has approved it for use against several plant diseases including downy mildew and various Phytophthora species including late blight on crops including vegetables, ornamentals, and turf.

Its mechanism of action involves binding to the oxysterol-binding protein in Oomycetes.

References

  1. 1 2 "Orondis - Fungicide Product & Label Information". Syngenta US. Retrieved 2021-03-24.
  2. ↑ "Oxathiapiprolin" (PDF). New Active Ingredient Review. Minnesota Department of Agriculture. October 2015. Archived from the original (PDF) on 2017-11-07. Retrieved 2017-11-03.
  3. ↑ Cohen, Yigal (2015). "The Novel Oomycide Oxathiapiprolin Inhibits All Stages in the Asexual Life Cycle of Pseudoperonospora cubensis - Causal Agent of Cucurbit Downy Mildew". PLOS ONE. 10 (10) e0140015. Bibcode:2015PLoSO..1040015C. doi:10.1371/journal.pone.0140015. PMC 4599937. PMID 26452052.
  4. ↑ Pasteris, Robert J; Hanagan, Mary Ann; Bisaha, John J; Finkelstein, Bruce L; Hoffman, Lisa E; Gregory, Vann; Shepherd, Christopher P; Andreassi, John L; Sweigard, James A; Klyashchitsky, Boris A; Henry, Yewande T; Berger, Richard A (2015). "The Discovery of Oxathiapiprolin: A New, Highly-Active Oomycete Fungicide with a Novel Site of Action". Discovery and Synthesis of Crop Protection Products. ACS Symposium Series. Vol. 1204. p. 149. doi:10.1021/bk-2015-1204.ch011. ISBN 978-0-8412-3102-3.