Flufenoxuron

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. It acts by inhibiting chitin synthase,

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.

Synthesis

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

synthesis of flufenoxuron
synthesis of flufenoxuron

Trade name

flufenoxuron is marketed under the trade name Cascade (BASF) and Floxate (Mobedco).

Authorization

Flufenoxuron was banned in the EU due to bioaccumulation. 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.

Toxicology and safety

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

References

  1. 1 2 3 "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. 1 2 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. 1 2 3 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.