Flufenoxuron

Last updated
Flufenoxuron
Flufenoxuron.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 417-680-3
KEGG
PubChem CID
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 chitin synthesis inhibitor group, which also includes diflubenzuron, triflumuron, and lufenuron. [1] [2]

Contents

Application

caterpillar of agrotis ipsilon Agrotis ipsilon, aardrups.jpg
caterpillar of agrotis ipsilon

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

The multi-step synthesis of flufenoxuron is described in the following reaction sequence: [3]

synthesis of flufenoxuron Flufenoxuron Synthesis.svg
synthesis of flufenoxuron

Trade name

A plant protection product containing the active ingredient flufenoxuron is marketed under the trade name Cascade [3] .

Authorization

No plant protection products containing this active ingredient are authorized in Germany or in the EU. [2]

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. [5]

References

  1. 1 2 3 "Flufenoxuron". NIH - National Center for Biotechnology Information.
  2. 1 2 Entry on Flufenoxuron . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  3. 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
  4. ↑ 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)
  5. ↑ 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.
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