Flufenoxuron
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Basic Info
| Common Name | Flufenoxuron(F05776) |
| 2D Structure | |
| FRCD ID | F05776 |
| CAS Number | 101463-69-8 |
| PubChem CID | 91766 |
| Formula | C21H11ClF6N2O3 |
| IUPAC Name | N-[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]carbamoyl]-2,6-difluorobenzamide |
| InChI Key | RYLHNOVXKPXDIP-UHFFFAOYSA-N |
| InChI | InChI=1S/C21H11ClF6N2O3/c22-12-8-10(21(26,27)28)4-7-17(12)33-11-5-6-16(15(25)9-11)29-20(32)30-19(31)18-13(23)2-1-3-14(18)24/h1-9H,(H2,29,30,31,32) |
| Canonical SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=C(C=C(C=C2)OC3=C(C=C(C=C3)C(F)(F)F)Cl)F)F |
| Isomeric SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=C(C=C(C=C2)OC3=C(C=C(C=C3)C(F)(F)F)Cl)F)F |
| Synonyms |
Flufenoxuron
101463-69-8
Cascade
Flufenoxuron [ISO]
UNII-OD068OSS0N
OD068OSS0N
WL 115110
CHEBI:39382
RYLHNOVXKPXDIP-UHFFFAOYSA-N
N-(((4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluorophenyl)amino)carbonyl)-2,6-difluorobenzamide
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | N-phenylureas |
| Intermediate Tree Nodes | N-acyl-phenylureas |
| Direct Parent | N-benzoyl-N'-phenylureas |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | N-benzoyl-n'-phenylurea - Diphenylether - Diaryl ether - 2-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Trifluoromethylbenzene - Benzoic acid or derivatives - Phenoxy compound - Benzoyl - Phenol ether - Halobenzene - Chlorobenzene - Fluorobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Vinylogous halide - Carbonic acid derivative - Urea - Carboxylic acid derivative - Ether - 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 |
| Description | This 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 Name | Property Value |
|---|---|
| Molecular Weight | 488.77 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 4 |
| Complexity | 689 |
| Monoisotopic Mass | 488.036 |
| Exact Mass | 488.036 |
| XLogP | 6.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 33 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9765 |
| Human Intestinal Absorption | HIA+ | 0.9836 |
| Caco-2 Permeability | Caco2+ | 0.5105 |
| P-glycoprotein Substrate | Non-substrate | 0.7380 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7419 |
| Non-inhibitor | 0.9490 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8994 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8691 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6794 |
| CYP450 2D6 Substrate | Non-substrate | 0.8106 |
| CYP450 3A4 Substrate | Non-substrate | 0.6137 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5301 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5268 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8146 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7326 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9079 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6599 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9647 |
| Non-inhibitor | 0.8333 | |
| AMES Toxicity | Non AMES toxic | 0.8681 |
| Carcinogens | Non-carcinogens | 0.6679 |
| Fish Toxicity | High FHMT | 0.9849 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9984 |
| Honey Bee Toxicity | Low HBT | 0.8372 |
| Biodegradation | Not ready biodegradable | 0.9891 |
| Acute Oral Toxicity | III | 0.8046 |
| Carcinogenicity (Three-class) | Non-required | 0.5470 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.6707 | LogS |
| Caco-2 Permeability | 1.2280 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0058 | LD50, mol/kg |
| Fish Toxicity | 0.5381 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2621 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Guavas (Brazilian guavas, Cattley guavas, Costarican guavas, Guayabillos, Parà guavas,) | 0163070 | European Union | 0.05* | 07/11/2009 | |
| Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,) | 0212010 | European Union | 0.05* | 07/11/2009 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.05* | 07/11/2009 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 0.05* | 07/11/2009 | |
| Palm hearts | 0270090 | European Union | 0.05* | 07/11/2009 | |
| Cultivated fungi (Common mushrooms/button mushrooms/champignons mushrooms, Corn smuts/ Mexican truffles, Enokitake/winter mushrooms, Fusarium venenatum, Horse mushrooms, Jew's ears/hirneola, Nameko... | 0280010 | European Union | 0.05* | 07/11/2009 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 07/11/2009 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.05* | 07/11/2009 | |
| Bud spices | 0850000 | European Union | 0.05* | 07/11/2009 | |
| Cloves (Cassia buds, Cassia buds, Cassia buds,) | 0850010 | European Union | 0.05* | 07/11/2009 | |
| (b) bovine (American buffalo, Banteng, Buffalo, European buffalo/wisent, Gayal, Yak (domestic), Zebu, Hybrids of genera Bison, Bos, Bubalus and Poëphagus,) | 1012000 | European Union | 0.05* | 07/11/2009 | |
| (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... | 1016000 | European Union | 0.05* | 07/11/2009 | |
| Goat | 1020030 | European Union | 0.05* | 07/11/2009 | |
| Horse (Species listed with code numbers 1015000-xxx,) | 1020040 | European Union | 0.05* | 07/11/2009 | |
| Citrus fruits | 0110000 | European Union | 0.3 | 07/11/2009 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.3 | 07/11/2009 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.3 | 07/11/2009 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.3 | 07/11/2009 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.3 | 07/11/2009 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.3 | 07/11/2009 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Miniaturized QuEChERS based methodology for multiresidue determination ofpesticides in odonate nymphs as ecosystem biomonitors. | Talanta | 2018 Feb 1 | 29136841 |
| Ultrasound-assisted, hybrid ionic liquid, dispersive liquid-liquidmicroextraction for the determination of insecticides in fruit juices based onpartition coefficients. | J Sep Sci | 2017 Sep | 28675591 |
| Revealing Pesticide Residues Under High Pesticide Stress in Taiwan's AgriculturalEnvironment Probed by Fresh Honey Bee (Hymenoptera: Apidae) Pollen. | J Econ Entomol | 2017 Oct 1 | 28981672 |
| A Fundamental Step in IPM on Grapevine: Evaluating the Side Effects of Pesticideson Predatory Mites. | Insects | 2015 Oct 9 | 26466903 |
| 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 A | 2014 Sep 19 | 25124227 |
| Study on the simultaneous determination of seven benzoylurea pesticides in Oolongtea and their leaching characteristics during infusing process by HPLC-MS/MS. | Food Chem | 2014 Jan 15 | 24054259 |
| Influence of the matrix in bioavailability of flufenoxuron, lufenuron,pyriproxyfen and fenoxycarb residues in grapes and wine. | Food Chem Toxicol | 2013 Oct | 23941774 |
| The effect of insecticides on the non-target predatory mite Kampimodromusaberrans: laboratory studies. | Chemosphere | 2013 Oct | 23856464 |
| Compatibility of the entomopathogenic fungus Beauveria bassiana with flufenoxuronand azadirachtin against Tetranychus urticae. | Exp Appl Acarol | 2012 Dec | 22744196 |
| 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 Assess | 2011Feb | 21318916 |
| Effectiveness of pressurized liquid extraction and solvent extraction for thesimultaneous quantification of 14 pesticide residues in green tea using GC. | J Sep Sci | 2008 Jun | 18481329 |
| Compatibility of Verticillium lecani (Zimm.) with several pesticides. | Commun Agric Appl Biol Sci | 2007 | 18396843 |
| Determination of seven benzoylphenylurea insecticides in processed fruit andvegetables using high-performance liquid chromatography/tandem mass spectrometry. | Rapid Commun Mass Spectrom | 2005 | 16136517 |
| Development of a compound-specific ELISA for flufenoxuron and an improvedclass-specific assay for benzoylphenylurea insect growth regulators. | J Agric Food Chem | 1999 Aug | 10552666 |