Flufenoxuron

Flufenoxuron is an insecticide that belongs to the benzoylurea chitin synthesis inhibitor group, which also includes diflubenzuron, triflumuron, and lufenuron.^[1][2]

Flufenoxuron

Names
Preferred IUPAC name N-({4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}carbamoyl)-2,6-difluorobenzamide
Identifiers
CAS Number	101463-69-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:39382
ChEMBL	ChEMBL2287680
ChemSpider	82863
DrugBank	DB15006
ECHA InfoCard	100.101.654
EC Number	417-680-3
KEGG	C18430
PubChem CID	91766
UNII	OD068OSS0N
CompTox Dashboard (EPA)	DTXSID1041978
InChI 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
SMILES 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
Chemical formula	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). Infobox references

Application

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

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]