Lufenuron
[CAS# 103055-07-8]

Identification

• Classification: Chemical pesticide >> Insecticide >> Organochlorine insecticide
• Name: Lufenuron
• Synonyms: (RS)-1-[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxyl)phenyl]3-(2,6-difluorobenzoyl)urea; CGA-184,699
• Molecular Formula: C₁₇H₈Cl₂F₈N₂O₃
• Molecular Weight: 511.15
• CAS Registry Number: 103055-07-8
• EC Number: 410-690-9
• SMILES: C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C=C2Cl)OC(C(C(F)(F)F)F)(F)F)Cl)F

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Index of refraction: 1.523 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H317:-H400:-H410:
• Precautionary Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovory and Applicatios

Lufenuron is a benzoylurea-class insect growth regulator (IGR) used primarily in veterinary medicine and agriculture to control insect pests. It acts by inhibiting chitin synthesis, a critical component of the insect exoskeleton, thereby disrupting molting and development. The molecular formula of lufenuron is C₁₇H₈Cl₂F₈N₂O₃, and its structure features a substituted phenyl ring, a difluorophenoxy group, and a urea moiety.

Lufenuron was developed in the 1990s as part of a new generation of insecticides that offered selective action with reduced toxicity to mammals and beneficial insects. It functions by interfering with the synthesis and deposition of chitin in immature insect stages. As a result, larvae are unable to properly form new exoskeletons during molting, leading to death and interruption of the reproductive cycle.

In agriculture, lufenuron is used to manage pests such as leafminers, caterpillars, and thrips in crops including cotton, vegetables, and ornamentals. Its residual activity and stability on plant surfaces contribute to long-lasting protection. The compound is typically applied as a foliar spray and exhibits both contact and ingestion activity.

In veterinary applications, lufenuron is most widely known as an oral or injectable medication for flea control in cats and dogs. It works by preventing the development of flea eggs and larvae but does not kill adult fleas. When administered to a pet, lufenuron is distributed systemically and ingested by adult fleas during blood feeding, transferring the compound to their offspring.

Lufenuron is also used as part of integrated pest management programs due to its specificity and low environmental persistence. Its targeted mode of action minimizes harm to non-target organisms, making it compatible with ecological approaches to pest control.

Toxicological studies have shown that lufenuron has low acute toxicity in mammals and birds. It is poorly soluble in water and exhibits low bioaccumulation potential. It is metabolized slowly in treated animals and excreted mainly via feces.

In summary, lufenuron is a benzoylurea insect growth regulator used in agriculture and veterinary medicine to inhibit chitin synthesis in insects. Its effectiveness, safety profile, and specificity make it a valuable tool in managing insect populations while minimizing environmental impact.

References

1996. Impact of an orally administered insect growth regulator (lufenuron) on flea infestations of dogs in a controlled simulated home environment. American Journal of Veterinary Research, 57(4).
DOI: 10.2460/ajvr.1996.57.04.502

1996. Evaluation of flea control programmes for cats using fenthion and lufenuron. The Veterinary Record, 138(4).
DOI: 10.1136/vr.138.4.79

2024. Experimental study on photodegradation and leaching of typical pesticides in greenhouse soil from Shouguang, Shandong Province, East China. Ecological Processes, 13(1).
DOI: 10.1186/s13717-024-00503-x