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
CAS Number	1003318-67-9  Y
3D model (JSmol)	Interactive image
Beilstein Reference	20731698
ChEBI	CHEBI:83271
ChemSpider	32697748
ECHA InfoCard	100.227.885
EC Number	801-263-1
PubChem CID	56945145
UNII	56498AIV8R  Y
InChI 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
SMILES CC1=CC(=NN1CC(=O)N2CCC(CC2)C3=NC(=CS3)C4=NOC(C4)C5=C(C=CC=C5F)F)C(F)(F)F
Properties
Chemical formula	C24H22F5N5O2S
Molar mass	539.53 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

Oxathiapiprolin (trade names Orondis, ^[1] 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 ^[1] including late blight on crops including vegetables, ornamentals, and turf. ^[2]

Its mechanism of action involves binding to the oxysterol-binding protein in Oomycetes. ^{[3] [4]}

References

1. "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.