Flufenoxuron
Names
Preferred IUPAC name
N-({4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}carbamoyl)-2,6-difluorobenzamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.101.654 Edit this at Wikidata
EC Number
  • 417-680-3
KEGG
UNII
  • InChI=1S/C21H11ClF6N2O3/c22-12-8-10(21(26,27)28)4-7-17(12)33-11-5-6-16(15(25)9-11)29-20(32)30-19(31)18-13(23)2-1-3-14(18)24/h1-9H,(H2,29,30,31,32)
    Key: RYLHNOVXKPXDIP-UHFFFAOYSA-N
  • C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=C(C=C(C=C2)OC3=C(C=C(C=C3)C(F)(F)F)Cl)F)F
Properties
C21H11ClF6N2O3
Molar mass 488.77 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flufenoxuron is an insecticide that belongs to the benzoylurea class, which also includes diflubenzuron, triflumuron, and lufenuron.[1][2] It acts by inhibiting chitin synthase,[3]

Application

caterpillar of agrotis ipsilon

Flufenoxuron is used against mites and insect pests on pome fruit, vines, citrus, tea, cotton, maize, soya, vegetables and ornamentals.[4][5]

Synthesis

The multi-step synthesis of flufenoxuron is described in the following reaction sequence:[5]

synthesis of flufenoxuron
synthesis of flufenoxuron

Trade name

flufenoxuron is marketed under the trade name Cascade (BASF) and Floxate (Mobedco).[4][5]

Authorization

Flufenoxuron was banned in the EU due to bioaccumulation.[6] It was never registered in the US.

Properties

Flufenoxuron is a white crystalline powder. It has low solubility in water, is not flammable, and is not an oxidizer.[1]

Toxicology and safety

Flufenoxuron toxicity to humans and other mammals is low,[1] but it has a potentially high bioaccumulation in fish despite its low water solubility.[7]

References

  1. ^ a b c "Flufenoxuron". NIH - National Center for Biotechnology Information.
  2. ^ Entry on Flufenoxuron. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
  3. ^ Douris, Vassilis; Steinbach, Denise; Panteleri, Rafaela; Livadaras, Ioannis; Pickett, John Anthony; Van Leeuwen, Thomas; Nauen, Ralf; Vontas, John (2016). "2016". Proceedings of the National Academy of Sciences. 113 (51): 14692–14697. doi:10.1073/pnas.1618258113. PMC 5187681. PMID 27930336.
  4. ^ a b Tomlin, Clive D. S. (2006). Pesticide Manual, A World Compendium (14th ed.). Alton, Hampshire, England: British Crop Protection Council (published 1 November 2006). pp. 486–487. ISBN 978-1-901396-14-0.
  5. ^ a b c Thomas A. Unger (1996), "Flufenoxuron", Pesticide Synthesis Handbook, Park Ridge, N.J.: Noyes Publications, p. 235, ISBN 978-0-8155-1401-5
  6. ^ "Factsheet - 32011R0942". European Free Trade Association. Retrieved 22 September 2026.
  7. ^ Tang, Caiming; Zhu, Yizhe; Liang, Yiyang; Xia, Dan; Xu, Jiale; Zheng, Ruifen; Liu, Ling; Ma, Shirong; Lin, Hui; Luo, Xiao-Jun; Huang, Qingguo; Mai, Bi-Xian (2025-01-29). "Nontarget Analysis and Characterization of a Group of Abundant Polyfluoroalkyl Substances─Fluorinated Benzoylurea Pesticides and Their Analogues and Transformation Products in Fish by LC-HRMS and Chemical Species-Specific Algorithms". Journal of Agricultural and Food Chemistry. 73 (4): 2322–2331. Bibcode:2025JAFC...73.2322T. doi:10.1021/acs.jafc.4c09728. ISSN 0021-8561. PMID 39806269.