Flubendiamide

Last updated
Flubendiamide
Flubendiamide.svg
Names
Preferred IUPAC name
N1-[4-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2-methylphenyl]-3-iodo-N2-[1-(methanesulfonyl)-2-methylpropan-2-yl]benzene-1,2-dicarboxamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.130.778 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 608-064-7
KEGG
PubChem CID
UNII
  • InChI=1S/C23H22F7IN2O4S/c1-12-10-13(21(24,22(25,26)27)23(28,29)30)8-9-16(12)32-18(34)14-6-5-7-15(31)17(14)19(35)33-20(2,3)11-38(4,36)37/h5-10H,11H2,1-4H3,(H,32,34)(H,33,35)
    Key: ZGNITFSDLCMLGI-UHFFFAOYSA-N
  • CC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)F)NC(=O)C2=C(C(=CC=C2)I)C(=O)NC(C)(C)CS(=O)(=O)C
Properties
C23H22F7IN2O4S
Molar mass 682.39 g·mol−1
AppearanceWhite crystalline powder
Density 1.659 g·cm−3
Melting point 217.5–220.7 °C (423.5–429.3 °F; 490.6–493.8 K)
0.0003 g·L−1
Solubility in acetone 102 g·L−1
Hazards
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H400
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flubendiamide is the first insecticide of the diamide class. [1] [2] It acts on the ryanodine receptor. [2]

Legality

A environmentally persistent metabolite of flubendiamide is quite toxic to aquatic invertebrates, causing flubendiamide to be banned by the United States EPA. [3] The product is still available in other jurisdictions such as Europe [4] and India. [5]

References

  1. ↑ Jeanguenat, Andre (28 August 2012). "The story of a new insecticidal chemistry class: the diamides" . Pest Management Science. 69 (1): 7−14. doi:10.1002/ps.3406. PMID   23034936.
  2. 1 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. Bibcode:2023JAFC...71.3620D. doi:10.1021/acs.jafc.2c08414. PMID   36791236.
  3. ↑ "Flubendiamide – Notice of Intent to Cancel and Other Supporting Documents". United States Environmental Protection Agency. February 14, 2024. Retrieved 12 November 2023.
  4. ↑ "Flubendiamide". Nichino Europe. Retrieved 20 December 2021.
  5. ↑ "Fame". Bayer CropScience India. Archived from the original on 20 December 2021. Retrieved 20 December 2021.
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