Broflanilide

Broflanilide
Names
IUPAC name
3-[benzoyl(methyl)amino]-N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.214.739 Edit this at Wikidata
EC Number
  • 688-148-8
KEGG
UNII
  • InChI=1S/C25H14BrF11N2O2/c1-39(21(41)12-6-3-2-4-7-12)17-9-5-8-14(18(17)27)20(40)38-19-15(23(29,30)31)10-13(11-16(19)26)22(28,24(32,33)34)25(35,36)37/h2-11H,1H3,(H,38,40)
    Key: QSLZKWPYTWEWHC-UHFFFAOYSA-N
  • CN(C1=CC=CC(=C1F)C(=O)NC2=C(C=C(C=C2Br)C(C(F)(F)F)(C(F)(F)F)F)C(F)(F)F)C(=O)C3=CC=CC=C3
Properties
C25H14BrF11N2O2
Molar mass 663.285 g·mol−1
Hazards
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Broflanilide is a complex, polycyclic, organohalogen insecticide which provides a novel mode of action (MoA).

Mode of action

Upon its discovery by Mitsui Chemicals, Insecticide Resistance Action Committee (IRAC) created the new MoA Group 30 for Broflanilide. Broflanilide is a meta-diamide GABA-gated Cl− channel allosteric modulator. This - along with isoxazolines providing the same MoA, so far only fluxametamide - constitute the new MoA Group 30 in the IRAC classification scheme.

Advantages

Environmental Hazards

The EPA has stated that Broflanilide is "Likely to be Carcinogenic to Humans".

Broflanilide meets the EPA Working Definition of PFAS. Note that "EPA considers any level of PFAS to be potentially toxicologically significant".

Products

Products were registered in the United States in January, 2021, and in Canada. It is being sold under the brand names Cimegra (BASF) and Teraxxa (BASF, the seed treatment form).

References

  1. 1 2 3 4 BASF AgSolutions CA (Feb 16, 2021). Wireworm Manamgent Strategies. Youtube. Canada.
  2. 1 2 IRAC Mode of Action Classification, Annex 6, 2018
  3. 1 2 3 "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
  4. 1 2 Katsuta, Hiroyuki; Nomura, Michikazu; Wakita, Takeo; Daido, Hidenori; Kobayashi, Yumi; Kawahara, Atsuko; Banba, Shinichi (2019-05-20). "Discovery of broflanilide, a novel insecticide". Journal of Pesticide Science. 44 (2). Pesticide Science Society of Japan: 120–128. doi:10.1584/jpestics.d18-088. ISSN 1348-589X. PMC 6529746. PMID 31148938. S2CID 133133494.
  5. ↑ "Broflanilide; Pesticide Tolerances". EPA. 17 December 2020. Retrieved 16 November 2021.
  6. ↑ "Per- and Polyfluoroalkyl Substances (PFAS) in Pesticide Packaging". EPA. 13 January 2021. Retrieved 15 November 2021.
  7. ↑ "New Active Ingredient Broflanilide". EPA. Retrieved 16 November 2021.
  8. ↑ "Cimegra® - Product Profile". BASF Agriculture Western Canada. BASF Canada. 2021-03-10. Retrieved 2021-03-10.
  9. ↑ "Teraxxa™ and Teraxxa™ F4 Seed Treatments". BASF Agriculture US. BASF US. Retrieved 2021-03-10.