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 |
| EC Number |
|
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| 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 chitin synthesis inhibitor group, which also includes diflubenzuron, triflumuron, and lufenuron.[1][2]
Application
[edit]
Flufenoxuron is used as an insecticide primarily on citrus plants, cotton, grape, tea and soybean.[3]
Due to the development of resistance in some cases, the effects of chlorfluazuron and flufenoxuron on selected developmental and reproductive parameters of the agrotis ipsilon were examined in a study. It was found that chlorfluazuron and flufenoxuron can accelerate vitellogenesis (yolk formation during oocyte development) in the ypsilon owl.[4]
Synthesis
[edit]The multi-step synthesis of flufenoxuron is described in the following reaction sequence:[3]
Trade name
[edit]A plant protection product containing the active ingredient flufenoxuron is marketed under the trade name Cascade.[3]
Authorization
[edit]No plant protection products containing this active ingredient are authorized in Germany or in the EU.[2]
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.[5]
References
[edit]- 1 2 3 "Flufenoxuron". NIH - National Center for Biotechnology Information.
- 1 2 Entry on Flufenoxuron. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
- 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
- ↑ El-Sayed H. Shaurub, Nawal Z. Zohdy, Aziza E. Abdel-Aal, Said A. Emara (2018-01-02), "Effect of chlorfluazuron and flufenoxuron on development and reproductive performance of the black cutworm, Agrotis ipsilon (Hufnagel) (Lepidoptera: Noctuidae)", Invertebrate Reproduction & Development, vol. 62, no. 1, pp. 27–34, doi:10.1080/07924259.2017.1384407
{{citation}}: CS1 maint: multiple names: authors list (link) - ↑ 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.