Lufenuron

Basic Info

Common NameLufenuron(F06131)
2D Structure
FRCD IDF06131
CAS Number103055-07-8
PubChem CID71777
FormulaC17H8Cl2F8N2O3
IUPAC Name

N-[[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]carbamoyl]-2,6-difluorobenzamide

InChI Key

PWPJGUXAGUPAHP-UHFFFAOYSA-N

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)

Canonical 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

Isomeric 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

Synonyms
        
            N-((2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)carbamoyl)-2,6-difluorobenzamide
        
            Lufenuron
        
            103055-07-8
        
            Fluphenacur
        
            UNII-9CR45YMS74
        
            9CR45YMS74
        
            CHEBI:39384
        
            PWPJGUXAGUPAHP-UHFFFAOYSA-N
        
            UNII-4629851K7Q
        
            1-(2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)-3-(2,6-difluorobenzoyl)urea
Classifies
                

                  
                    Veterinary Drug
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesNot available
Direct ParentN-phenylureas
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsN-phenylurea - Phenoxy compound - 1,4-dichlorobenzene - Phenol ether - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Carbonic acid derivative - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Alkyl fluoride - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Properties

Property NameProperty Value
Molecular Weight511.149
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count5
Complexity677
Monoisotopic Mass509.978
Exact Mass509.978
XLogP6.4
Formal Charge0
Heavy Atom Count32
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9765
Human Intestinal AbsorptionHIA+0.9836
Caco-2 PermeabilityCaco2+0.5105
P-glycoprotein SubstrateNon-substrate0.7380
P-glycoprotein InhibitorNon-inhibitor0.7419
Non-inhibitor0.9490
Renal Organic Cation TransporterNon-inhibitor0.8994
Distribution
Subcellular localizationMitochondria0.8691
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6794
CYP450 2D6 SubstrateNon-substrate0.8106
CYP450 3A4 SubstrateNon-substrate0.6137
CYP450 1A2 InhibitorInhibitor0.5301
CYP450 2C9 InhibitorInhibitor0.5268
CYP450 2D6 InhibitorNon-inhibitor0.8146
CYP450 2C19 InhibitorInhibitor0.7326
CYP450 3A4 InhibitorNon-inhibitor0.9079
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6599
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9647
Non-inhibitor0.8333
AMES ToxicityNon AMES toxic0.8681
CarcinogensNon-carcinogens0.6679
Fish ToxicityHigh FHMT0.9849
Tetrahymena Pyriformis ToxicityHigh TPT0.9984
Honey Bee ToxicityLow HBT0.8372
BiodegradationNot ready biodegradable0.9891
Acute Oral ToxicityIII0.8046
Carcinogenicity (Three-class)Non-required0.5470
Model Value Unit
Absorption
Aqueous solubility-5.6707LogS
Caco-2 Permeability1.2280LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0058LD50, mol/kg
Fish Toxicity0.5381pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.2621pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.02*01/09/2008
Walnuts0120110European Union0.0301/09/2008
Others (2)0120990European Union0.02*01/09/2008
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union0.501/09/2008
Melons (Kiwanos/horned melons,)0233010European Union0.301/09/2008
Citrus fruits0110000European Union101/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union101/09/2008
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union101/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union101/09/2008
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union101/09/2008
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union101/09/2008
Others (2)0110990European Union101/09/2008
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*01/09/2008
Brazil nuts0120020European Union0.02*01/09/2008
Cashew nuts0120030European Union0.02*01/09/2008
Chestnuts0120040European Union0.02*01/09/2008
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*01/09/2008
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*01/09/2008
Macadamias0120070European Union0.02*01/09/2008
Pecans (Hickory nuts,)0120080European Union0.02*01/09/2008

References

TitleJournalDatePubmed ID
Ultrasound-assisted, hybrid ionic liquid, dispersive liquid-liquidmicroextraction for the determination of insecticides in fruit juices based onpartition coefficients.J Sep Sci2017 Sep28675591
Examination of the "susceptibility gap" in the treatment of canine heartworminfection.Parasit Vectors2017 Nov 929143689
Ionic liquid-assisted liquid-phase microextraction based on the solidification offloating organic droplets combined with high performance liquid chromatographyfor the determination of benzoylurea insecticide in fruit juice.J Chromatogr A2014 Sep 1925124227
The impact of insecticides applied in apple orchards on the predatory miteKampimodromus aberrans (Acari: Phytoseiidae).Exp Appl Acarol2014 Mar24114337
Influence of the matrix in bioavailability of flufenoxuron, lufenuron,pyriproxyfen and fenoxycarb residues in grapes and wine.Food Chem Toxicol2013 Oct23941774
Residue and dissipation dynamics of lufenuron in tomato fruit using QuEChERSmethodology.Bull Environ Contam Toxicol2012 Nov22965335
Efficacy of insect growth regulators as grain protectants against twostored-product pests in wheat and maize.J Food Prot2012 May22564945
Fate of three insect growth regulators (IGR) insecticides (flufenoxuron,lufenuron and tebufenozide) in grapes following field application and through thewine-making process.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Feb21318916
Effectiveness of insecticides in controlling the first and second generations of the Lobesia botrana (Lepidoptera: Tortricidae) in table grapes.J Econ Entomol2011 Apr21510208
Determination of sixteen pesticides in peppers using high-performance liquidchromatography/mass spectrometry.J Environ Sci Health B201121726151
Mediterranean fruit fly suppression using chemosterilants for area-wideintegrated pest management.Pest Manag Sci2010 May20101608
Minor crops for export: a case study of boscalid, pyraclostrobin, lufenuron andlambda-cyhalothrin residue levels on green beans and spring onions in Egypt.J Environ Sci Health B2010 Aug20574869
Bioavailability of insect growth regulator residues in citrus.Ecotoxicology2009 Nov19636704
Responses of zooplankton in lufenuron-stressed experimental ditches in thepresence or absence of uncontaminated refuges.Environ Toxicol Chem2008 Jun18466038
Development and application of a method for analysis of lufenuron in wheat flour by gas chromatography-mass spectrometry and confirmation of bio-efficacy against Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae).J Chromatogr B Analyt Technol Biomed Life Sci2008 Jan 118078793
Agrichemical impact on growth and survival of non-target apple phyllospheremicroorganisms.Can J Microbiol2007 Jan17496949
Bioavailability of insect growth regulators in citrus and stone fruits.Commun Agric Appl Biol Sci200718399436
Determination of seven benzoylphenylurea insecticides in processed fruit andvegetables using high-performance liquid chromatography/tandem mass spectrometry.Rapid Commun Mass Spectrom200516136517
Efficacy of lufenuron as chemosterilant against Ceratitis capitata in fieldtrials.Pest Manag Sci2004 Sep15384180
Pre- and postharvest effects of lufenuron on Epiphyas postvittana (Lepidoptera:Tortricidae).J Econ Entomol2000 Jun10902315