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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.101.025 Edit this at Wikidata
KEGG
UNII
  • 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) checkY
    Key: PWPJGUXAGUPAHP-UHFFFAOYSA-N checkY
  • InChI=1/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)
    Key: PWPJGUXAGUPAHP-UHFFFAOYAQ
  • Clc1cc(c(Cl)cc1OC(F)(F)C(F)C(F)(F)F)NC(=O)NC(=O)c2c(F)cccc2F
Properties
C17H8Cl2F8N2O3
Molar mass 511.15 g·mol−1
Melting point 174 °C (345 °F; 447 K)
Pharmacology
QP53BC01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lufenuron is a chemical with insecticidal properties, belonging to the class of insecticides called insect growth regulators. It is a chitin synthesis inhibitor belonging to the benzoylurea class (IRAC group 15).

Applications

Veterinary

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

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 their excrement. It does not kill adult fleas.[citation needed]

Lufenuron 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).[citation needed]

Lufenuron is also used to fight fungal infections, since fungus cell walls are about one third chitin.[1]

Agriculture

Lufenuron is also sold as an agricultural pesticide for use against lepidopterans, eriophyid mites, and western flower thrips. It is an effective antifungal in plants.[2]

References

  1. ^ Ben-Ziony, Yair; Arzi, Boaz (2000). "Use of lufenuron for treating fungal infections of dogs and cats: 297 cases (1997-1999)". Journal of the American Veterinary Medical Association. 217 (10): 1510–3. doi:10.2460/javma.2000.217.1510. PMID 11128542.
  2. ^ Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V N (2014). The Pesticide Encyclopedia. Wallingford, Oxfordshire UK Boston, MA: CABI. p. 283. ISBN 978-1-78064-014-3. Retrieved Nov 22, 2018. Lufenuron, a chitin synthesis inhibitor, is an effective agent against lepidopteran members in crops, eriophid mites and western flower thrips. In non-crop situations too, lufenuron is effective against fleas on animals and on cockroaches in households. This chemical also acts as an anti-fungal agent in plants. ... According to the WHO, lufenuron is a Class III toxin (slightly hazardous). It is safe on mammals, since it is not broken down by the liver or kidneys.
  • Lufenuron in the Pesticide Properties DataBase (PPDB)

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