Lufenuron
| Lufenuron | |
|---|---|
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| 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 | |
| Identifiers | |
| CAS number | 103055-07-8  |
| PubChem | 71777 |
| ChemSpider | 64813  |
| KEGG | D08150 |
| ChEBI | CHEBI:39384 |
| ATCvet code | QP53 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C17H8Cl2F8N2O3 |
| Molar mass | 511.15 g/mol |
| Melting point | 174 °C; 345 °F; 447 K |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 bites. Adult fleas transfer it to their eggs by its presence in the female flea's blood, or by the larvae feeding on predigested 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[citation needed] (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 lepidopterans, 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 antifungal in plants. It is safe because it is biochemically inert to mammals. Lufenuron is not broken down by the liver or kidneys. Its antifungal property may be due to inhibition of chitin synthesis, 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 freshwater zooplankton [1] and approved by the European Parliament on January 13, 2009.[2]
References
- ↑ "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.
- ↑ "MEPs approve pesticides legislation". 2009-01-13. Retrieved 2009-01-14.