Lufenuron

Lufenuron
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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
CAS Number	103055-07-8 N;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39384 Y;
ChEMBL	ChEMBL1364906 N;
ChemSpider	64813 Y;
ECHA InfoCard	100.101.025
KEGG	D08150 N;
PubChem CID	71777;
UNII	1R754M4918 Y;
CompTox Dashboard (EPA)	DTXSID5034357 ;
	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; 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;
	SMILES Clc1cc(c(Cl)cc1OC(F)(F)C(F)C(F)(F)F)NC(=O)NC(=O)c2c(F)cccc2F;
Properties
Chemical formula	C17H8Cl2F8N2O3
Molar mass	511.15 g·mol−1
Melting point	174 °C (345 °F; 447 K)
Pharmacology
ATCvet code	QP53BC01 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.

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).

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

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.
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.

External links

Lufenuron in the Pesticide Properties DataBase (PPDB)

[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.

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