Flufenoxuron
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| Names | |
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| Preferred IUPAC name
N-({4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}carbamoyl)-2,6-difluorobenzamide | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
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| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.101.654 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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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
[edit]
Flufenoxuron is used against mites and insect pests on pome fruit, vines, citrus, tea, cotton, maize, soya, vegetables and ornamentals.[4][5]
Synthesis
[edit]The multi-step synthesis of flufenoxuron is described in the following reaction sequence:[5]
Trade name
[edit]flufenoxuron is marketed under the trade name Cascade (BASF) and Floxate (Mobedco).[4][5]
Authorization
[edit]Flufenoxuron was banned in the EU due to bioaccumulation.[6] It was never registered in the US.
Properties
[edit]Flufenoxuron is a white crystalline powder. It has low solubility in water, is not flammable, and is not an oxidizer.[1]
Toxicology and safety
[edit]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
[edit]- 1 2 3 "Flufenoxuron". NIH - National Center for Biotechnology Information.
- ↑ Entry on Flufenoxuron. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
- ↑ 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.
- 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 9781901396140.
{{cite book}}: Check|isbn=value: invalid character (help) - 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
- ↑ "Factsheet - 32011R0942". European Free Trade Association. Retrieved 22 September 2026.
- ↑ 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.