Lufenuron

Lufenuron

Lufenuron
Names
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
 N
ATCvet code QP53
ChEBI  Y
ChEMBL  N
ChemSpider  Y
Jmol-3D images Image
KEGG  N
PubChem
UNII  Y
Properties
C17H8Cl2F8N2O3
Molar mass 511.15 g·mol−1
Melting point 174 °C (345 °F; 447 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Lufenuron is the active ingredient in the veterinary flea control medication Program, and one of the two active ingredients in the flea, heartworm, and anthelmintic medicine milbemycin oxime/lufenuron (Sentinel).

Lufenuron is stored in the animal's body fat and transferred to adult fleas through the host's blood when they feed. Adult fleas transfer it to their growing eggs through their blood, and to hatched larvae feeding on her excrement. It does not kill adult fleas.

Lufenuron, a benzoylurea pesticide, inhibits the production of chitin in insects. Without chitin, a larval flea will never develop a hard outer shell (exoskeleton). With its inner organs exposed to air, the insect dies from dehydration soon after hatching or molting (shedding its old, smaller shell).

Lufenuron is also used to fight fungal infections, since fungus cell walls are about one third chitin.

Lufenuron is also sold as an agricultural pesticide for use against lepidopterans, eriophid mites, and western flower thrips. It is an effective antifungal in plants.

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

References

  1. ^ "Interpretation of criteria for approval of active substances in the proposed EU plant protection regulation". Swedish Chemicals Agency (KemI). 2008-09-23. Retrieved 2009-01-14. 
  2. ^ "MEPs approve pesticides legislation". 2009-01-13. Retrieved 2009-01-14. 

External Links

  • Lufenuron in the Pesticide Properties DataBase (PPDB)