Lufenuron CAS 103055-07-8

Introduction：Basic information about Lufenuron CAS 103055-07-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Lufenuron Basic information

• Product Name: Lufenuron
• Synonyms: fluphenacur;(rs)-1-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxyl)phenyl]3-(2,6-difluorobenzoyl)urea;cga-184,699;LUFENURON;Benzamide, N-2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenylaminocarbonyl-2,6-difluoro-;lufenuron (bsi,iso,inn);(RS)-1-[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea;N-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl-aminocarbonyl]-2,6-difluorobenzamide
• CAS: 103055-07-8
• MF: C17H8Cl2F8N2O3
• MW: 511.15
• EINECS: 410-690-9
• Product Categories: PROGRAM;103055-07-8
• Mol File: 103055-07-8.mol

Lufenuron Chemical Properties

• Melting point: 174.1°
• density: 1.631±0.06 g/cm3(Predicted)
• vapor pressure: <0.4 x10 -3 Pa (25 °C)
• Fp: 170 °C
• storage temp.: 0-6°C
• solubility: 100mg/L in organic solvents at 20 ℃
• form: Solid
• Water Solubility: <0.06 mg l^-1(25 °C)
• pka: 8.49±0.46(Predicted)
• color: Off-white to light yellow
• JECFA Number: 85
• BRN: 8398291
• 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)
• InChIKey: PWPJGUXAGUPAHP-UHFFFAOYSA-N
• SMILES: FC(C(F)(F)F)C(F)(F)Oc1cc(Cl)c(NC(=O)NC(=O)c2c(F)cccc2F)cc1Cl
• LogP: 5.12 at 25℃
• CAS DataBase Reference: 103055-07-8(CAS DataBase Reference)
• EPA Substance Registry System: Benzamide, N-[[[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino]carbonyl]-2,6-difluoro- (103055-07-8)

Safety Information

• Hazard Codes: Xi;N,N,Xi
• Risk Statements: 43-50/53
• Safety Statements: 2-24-37-60-61
• RIDADR: 3077
• WGK Germany: 2
• HazardClass: 9
• PackingGroup: III
• HS Code: 29242990
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Aquatic Acute 1 Aquatic Chronic 1 Skin Sens. 1
• Toxicity: LD50 in rats (mg/kg): >2000 orally; LC50 in rats (mg/m3): >2350 (Buholzer)

Lufenuron Usage And Synthesis

Description

Lufenuron is an insect development inhibitor of thebenzoylphenyl urea class. It demonstrates activity againstfleas that have fed on treated cats and dogs and becomeexposed to lufenuron in the host’s blood. Lufenuron alsohas activity by virtue of its presence in adult flea feces,leading to its ingestion by flea larvae. Both activities resultin the production of eggs that are unable to hatch, causingsignificant reductions in flea larvae populations. Thelipophilicity of lufenuron leads to its deposition in adipose tissues of animals from where it is slowly released into thebloodstream. This permits effective blood concentrationsto be maintained throughout the recommended oral dosinginterval of 1 month.

Uses

Lufenuron is used for the control of Lepidoptera and Coleopteralarvae on cotton, maize and vegetables, and of citrus whitefly and rustmites on citrus fruit. It is also used to control fleas on pets and cockroachesin houses.

Definition

ChEBI: Lufenuron is a benzoylurea insecticide, a dichlorobenzene, a N-acylurea, an aromatic ether and an organofluorine compound.

Flammability and Explosibility

Not classified

Pharmacology

Antiparasitic. Lufenuron is a benzoylurea insecticide. This class of insecticides was previously used on fruits to decrease damage by insects. Lufenuron (Program) has been used for prevention of flea infections in dogs and cats because it inhibits chitin synthesis. For this use, it has been given to dogs at a dose of 10 mg/kg every 30 days and to cats at a dose of 30 mg/kg every 30 days. It may also have some inhibition on fungal cell membranes because it inhibits the cell wall of fungi, which contain chitin, and other complex polysaccharides. Because of this property on fungal cell membranes, there has been interest in using lufenuron to treat dermatophytes in small animals. However, proven efficacy has been controversial. Well-controlled studies have not confirmed consistent efficacy for treating dermatophytes in animals.

Synthesis

A method for preparing Lufenuron comprises an addition reaction, a nitration reaction, a reduction reaction, an esterification reaction, and a four-step construction reaction, primarily involving the following steps:
Step 1,2,5-chlorophenesic acid are dissolved in effect and the reaction of gas perfluoro propylene of passing through potassium hydroxide solution among the DMF and generate the IMA crude product, and crude product is through after washing, and rectifying obtains the IMA elaboration in rectifying tower;
Step 2, IMA carries out nitration reaction in the vitriol oil and nitrosonitric acid;
Step 3 in etoh solvent, take gac as carrier, under the catalysis of catalyzer and salt of wormwood, is reduced IMB with reductive agent;
Step 4, in ethylene dichloride 2,6-difluorobenzamide and oxalyl chloride carry out esterification and obtain intermediate compound I MD;
Step 5, IMC and IMD building-up reactions in tetracol phenixin obtains the lufenuron finished product.

Veterinary Drugs and Treatments

Lufenuron is approved for use in dogs and cats 6 weeks of age andolder for the control of flea populations. The combination productof lufenuron and milbemycin (Sentinel?) is indicatedfor usein puppies and dogs 4 weeks and older for prevention and controlflea populations, preventionof heartworm disease, control of adulthookworms, and the removal and control of adult roundwormsand whipworms.
Lufeneron showed initial promise as a treatment for fungal infections,but the early enthusiasm has dampened considerably asefficacy appears doubtful.

Metabolic pathway

Only limited information is available in the open literature on themetabolism of lufenuron.

Degradation

Lufenuron is less stable at alkaline pH than under acidic conditions. TheDT₅₀ at 25 °C is 160 days at pH 5,70 days at pH 7 and 32 days at pH 9(PM).

Mode of action

Lufenuron has no systemic or translaminar effect. It is persistent with a transovarial effect. It may reduce the egg-Iaying rate or hinder the hatching process of embryos.