Lufenuron

Lufenuron
IUPAC name 1-[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea
Other names N-[ [ [2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino]carbonyl]-2,6-difluorobenzamide Fluphenacur U.S. EPA PC Code: 118205
Identifiers
CAS number	103055-07-8 N
PubChem	71777
ChemSpider	64813 Y
KEGG	D08150 N
ChEBI	CHEBI:39384 Y
ATCvet code	QP53BC01
Jmol-3D images	Image 1
SMILES Clc1cc(c(Cl)cc1OC(F)(F)C(F)C(F)(F)F)NC(=O)NC(=O)c2c(F)cccc2F
InChI InChI=1S/C17H8Cl2F8N2O3/c18-6-5-11(32-17(26,27)14(22)16(23,24)25)7(19)4-10(6)28-15(31)29-13(30)12-8(20)2-1-3-9(12)21/h1-5,14H,(H2,28,29,30,31) Y Key: PWPJGUXAGUPAHP-UHFFFAOYSA-N Y
Properties
Molecular formula	C17H8Cl2F8N2O3
Molar mass	511.15 g/mol
Melting point	174 °C, 447 K, 345 °F
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lufenuron is the active ingredient in the veterinary flea control medication Program, and one of the active ingredients in the veterinary flea control, heartworm prevention, and anthelmintic medicine milbemycin oxime/lufenuron (trade names Program plus, Sentinel Flavor Tabs).

Lufenuron is stored in the animal's body fat and transferred to adult fleas through their bite. Adult fleas transfer it to their eggs by its presence in the mother flea's blood, or by the larva feeding on pre-digested blood.

Lufenuron, a benzoylurea pesticide, inhibits the production of chitin in larval fleas. Without chitin, a larval flea will never develop an exoskeleton. Attacking the ability to create chitin may make lufenuron a remedy against fungal infections, such as ringworm (a dermatophyte infection and not a worm at all).

It has no known toxic effects at any dosage on humans or other animals in the environment that do not depend on chitin, though the orally-administered pills can sometimes cause an upset stomach with acid reflux.

Lufenuron is also sold as a crop protection product (pesticide) by Syngenta for use against lepidoptera, eriophid mites, and Western flower thrips; it has approval in a number of countries for use on a variety of crops, including soybeans and maize.

Lufenuron is thought to be an effective anti-fungal in plants. It is safe because Lufenuron is biochemically inert to mammals. Lufenuron is not broken down by the liver or kidneys. Lufenuron's antifungal property may be due to its inhibiting the synthesis of chitin, which makes up roughly 33% of the typical fungal cell wall.

Lufenuron was included in a biocide ban proposed by the Swedish Chemicals Agency because it is toxic to fresh water zooplankton ^[1] and approved by the European Parliament on January 13, 2009.^[2]

References