Hexaflumuron

Basic Info

Common NameHexaflumuron(F06218)
2D Structure
FRCD IDF06218
CAS Number86479-06-3
PubChem CID91741
FormulaC16H8Cl2F6N2O3
IUPAC Name

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

InChI Key

RGNPBRKPHBKNKX-UHFFFAOYSA-N

InChI

InChI=1S/C16H8Cl2F6N2O3/c17-7-4-6(5-8(18)12(7)29-16(23,24)14(21)22)25-15(28)26-13(27)11-9(19)2-1-3-10(11)20/h1-5,14H,(H2,25,26,27,28)

Canonical SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C(=C2)Cl)OC(C(F)F)(F)F)Cl)F

Isomeric SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C(=C2)Cl)OC(C(F)F)(F)F)Cl)F

Synonyms
        
            N-((3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)carbamoyl)-2,6-difluorobenzamide
        
            Hexaflumuron
        
            86479-06-3
        
            Hexafluoron
        
            Hexafluron
        
            Recruit
        
            Sentricon
        
            Hexaflumuron [ISO]
        
            XRD 473
        
            UNII-4GW50R449T
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassN-phenylureas
Intermediate Tree NodesN-acyl-phenylureas
Direct ParentN-benzoyl-N'-phenylureas
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsN-benzoyl-n'-phenylurea - 2-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Benzoic acid or derivatives - Benzoyl - Phenol ether - 1,3-dichlorobenzene - Phenoxy compound - Halobenzene - Chlorobenzene - Fluorobenzene - Aryl halide - Aryl chloride - Aryl fluoride - Vinylogous halide - Carbonic acid derivative - Urea - Carboxylic acid derivative - Alkyl fluoride - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - 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-benzoyl-n'-phenylureas. These are n-acyl-phenylureas that have the acyl group substituted by a phenyl group.

Properties

Property NameProperty Value
Molecular Weight461.141
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Complexity581
Monoisotopic Mass459.982
Exact Mass459.982
XLogP5.7
Formal Charge0
Heavy Atom Count29
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
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
Sugar BeetJapan0.02ppm
DateJapan0.02ppm
Passion FruitJapan0.5ppm
MangoJapan0.5ppm
GuavaJapan0.5ppm
PineappleJapan0.5ppm
AvocadoJapan0.5ppm
PapayaJapan0.5ppm
Other HerbsJapan0.02ppm
Other SpicesJapan0.02ppm
HopJapan0.02ppm
Cacao BeansJapan0.02ppm
Coffee BeansJapan0.02ppm
Other NutsJapan0.02ppm
WalnutJapan0.02ppm
AlmondJapan0.02ppm
PecanJapan0.02ppm
ChestnutJapan0.02ppm
Ginkgo NutJapan0.02ppm
Other Oil SeedsJapan0.02ppm

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
Dispersive micro-solid-phase extraction of benzoylurea insecticides in honeysamples with a β-cyclodextrin-modified attapulgite composite as sorbent.J Sep Sci2016 Jan26573895
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
Study on the simultaneous determination of seven benzoylurea pesticides in Oolongtea and their leaching characteristics during infusing process by HPLC-MS/MS.Food Chem2014 Jan 1524054259
Evaluation of etoxazole against insects and acari in vegetables in China.J Insect Sci201425199415
Synthesis and insecticidal activity of heptafluoroisopropyl-containingbenzoylphenylurea structures.J Agric Food Chem2010 Mar 1020014763
Dissipation and evaluation of hexaflumuron residues in chinese cabbage grown inopen fields.J Agric Food Chem2010 Apr 2820345168
[Determination of benzoylurea and bishydrazide pesticide residues in vegetablesby ultra performance liquid chromatography-tandem mass spectrometry with matrixsolid phase dispersion].Se Pu2010 Apr20712114
Phagostimulatory sugars enhance uptake and horizontal transfer of hexaflumuron inthe western subterranean termite (Isoptera: Rhinotermitidae).J Econ Entomol2008 Jun18613589
Capabilities of different liquid chromatography tandem mass spectrometry systems in determining pesticide residues in food. Application to estimate their dailyintake.J Chromatogr A2007 Jul 2017466998
Hermetically sealed baits for subterranean termites (Isoptera: Rhinotermitidae).J Econ Entomol2007 Apr17461073
Routine application using single quadrupole liquid chromatography-massspectrometry to pesticides analysis in citrus fruits.J Chromatogr A2005 Sep 2316130755
Effect of hexaflumuron on mortality of the Western subterranean termite(Isoptera: Rhinotermitidae) during and following exposure and movement ofhexaflumuron in termite groups.Pest Manag Sci2005 Jun15657953
Determination of five pesticide residues in oranges by matrix solid-phasedispersion and liquid chromatography to estimate daily intake of consumers.J AOAC Int2001 May-Jun11417653
Control of Coptotermes havilandi (Isoptera: Rhinotermitidae) with hexaflumuronbaits and a sensor incorporated into a monitoring and baiting program.J Econ Entomol2000 Apr10826194
Liquid chromatographic determination of five benzoylurea insecticides in fruitand vegetables.J AOAC Int1998 Sep-Oct9772746