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Lufenuron

From Wikipedia, the free encyclopedia
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 InfoCard100.101.025Edit 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 mass511.15 g·mol−1
Melting point174 °C (345 °F; 447 K)
Pharmacology
QP53BC01 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Lufenuron is theactive ingredient in theveterinaryflea control medication program, and one of the two active ingredients in the flea,heartworm, andanthelmintic medicinemilbemycin oxime/lufenuron (Sentinel).

Lufenuron is stored in the animal's bodyfat 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, abenzoylurea pesticide, inhibits the production ofchitin 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 fightfungal infections, since fungus cell walls are about one third chitin.[1]

Lufenuron is also sold as an agricultural pesticide for use againstlepidopterans, eriophyidmites, andwestern flower thrips. It is an effective antifungal in plants.[2]

References

[edit]
  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. RetrievedNov 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.

External links

[edit]
  • Lufenuron in the Pesticide Properties DataBase (PPDB)
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