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Broflanilide

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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

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Upon its discovery by Mitsui Chemicals, Insecticide Resistance Action Committee (IRAC) created the new MoA Group 30 for Broflanilide.[1][2][3][4] Broflanilide is a meta-diamide GABA-gated Cl− channel allosteric modulator.[1][2][3][4] This - along with isoxazolines providing the same MoA, so far only fluxametamide - constitute the new MoA Group 30 in the IRAC classification scheme.[3]

Advantages

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Environmental Hazards

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The EPA has stated that Broflanilide is "Likely to be Carcinogenic to Humans".[5]

Broflanilide meets the EPA Working Definition of PFAS. Note that "EPA considers any level of PFAS to be potentially toxicologically significant".[6]

Products

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Products were registered in the United States in January, 2021,[7] and in Canada.[1] It is being sold under the brand names Cimegra (BASF)[8] and Teraxxa (BASF, the seed treatment form).[9]

References

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  1. ^ a b c d BASF AgSolutions CA (Feb 16, 2021). Wireworm Manamgent Strategies. Youtube. Canada.
  2. ^ a b IRAC Mode of Action Classification, Annex 6, 2018
  3. ^ a b c "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
  4. ^ a b 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. 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.
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