Cyantraniliprole

Cyantraniliprole
Names
Preferred IUPAC name
4-Bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(N-methylcarbamoyl)phenyl]-1H-pyrazole-5-carboxamide
Other names
Cyazypyr; Exirel
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.205.162 Edit this at Wikidata
UNII
  • InChI=1S/C19H14BrClN6O2/c1-10-6-11(9-22)7-12(18(28)23-2)16(10)25-19(29)14-8-15(20)26-27(14)17-13(21)4-3-5-24-17/h3-8H,1-2H3,(H,23,28)(H,25,29)
    Key: DVBUIBGJRQBEDP-UHFFFAOYSA-N
  • InChI=1/C19H14BrClN6O2/c1-10-6-11(9-22)7-12(18(28)23-2)16(10)25-19(29)14-8-15(20)26-27(14)17-13(21)4-3-5-24-17/h3-8H,1-2H3,(H,23,28)(H,25,29)
    Key: DVBUIBGJRQBEDP-UHFFFAOYAE
  • CC1=CC(=CC(=C1NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br)C(=O)NC)C#N
Properties
C19H14BrClN6O2
Molar mass 473.72 g·mol−1
Melting point 217-219 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyantraniliprole is an insecticide of the diamide class (IRAC MoA group 28).[1] It shows strong activity and lepidoptera (caterpillars), and since it shows systemic activity it is also active against sucking pests such as aphids and whitefly.[2]

As part of an ongoing court dispute by the Center for Biological Diversity, in November 2022, the U.S. Court of Appeals for the D.C. Circuit ordered the United States Environmental Protection Agency to consider harms to plants and animals under the Endangered Species Act, and to put in place appropriate protections.[3] The draft report by the EPA showed that cyantraniliprole is likely to adversely affect about 41% of endangered or threatened species.[4]

References

  1. ^ IRAC International MoA Working Group (March 2020). "IRAC Mode of Action Classification Scheme Version 9.4". Insecticide Resistance Action Committee.
  2. ^ Du, Shaoqing; Hu, Xueping (February 15, 2023). "Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators". Journal of Agricultural and Food Chemistry. 71 (8): 3620–3638.{{cite journal}}: CS1 maint: date and year (link)
  3. ^ Legal Victory: Court Orders EPA to Protect Endangered Wildlife From Toxic Pesticide
  4. ^ Erickson, Britt E. (February 3, 2023). "Cyantraniliprole likely harms endangered species, EPA finds". Chemical and Engineering News. 101 (5).