Bifenthrin
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Basic Info
| Common Name | Bifenthrin(F06186) |
| 2D Structure | |
| FRCD ID | F06186 |
| CAS Number | 82657-04-3 |
| PubChem CID | 6442842 |
| Formula | C23H22ClF3O2 |
| IUPAC Name | (2-methyl-3-phenylphenyl)methyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate |
| InChI Key | OMFRMAHOUUJSGP-IRHGGOMRSA-N |
| InChI | InChI=1S/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12-/t18-,20-/m0/s1 |
| Canonical SMILES | CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)C3=CC=CC=C3 |
| Isomeric SMILES | CC1=C(C=CC=C1COC(=O)[C@@H]2[C@@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)C3=CC=CC=C3 |
| Synonyms |
BIFENTHRIN
Discipline
Empower
Fanfare
Biphenthrin
Kappa-bifenthrin
Kappa-bifenthrine
(R)-Bifenthrin
(1R)-cis-Bifenthrin
82657-04-3
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biphenyls and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Biphenyl - Benzyloxycarbonyl - Toluene - Cyclopropanecarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Chloroalkene - Haloalkene - Vinyl halide - Vinyl chloride - Monocarboxylic acid or derivatives - Alkyl fluoride - Organohalogen compound - Organochloride - Organofluoride - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Alkyl halide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 422.872 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Complexity | 622 |
| Monoisotopic Mass | 422.126 |
| Exact Mass | 422.126 |
| XLogP | 6 |
| Formal Charge | 0 |
| Heavy Atom Count | 29 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9804 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6579 |
| P-glycoprotein Substrate | Non-substrate | 0.5690 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5179 |
| Inhibitor | 0.5053 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8556 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9377 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7168 |
| CYP450 2D6 Substrate | Non-substrate | 0.8653 |
| CYP450 3A4 Substrate | Substrate | 0.6349 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8028 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7015 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8850 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8250 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9510 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8516 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9866 |
| Non-inhibitor | 0.8051 | |
| AMES Toxicity | Non AMES toxic | 0.5228 |
| Carcinogens | Carcinogens | 0.5351 |
| Fish Toxicity | High FHMT | 0.9995 |
| Tetrahymena Pyriformis Toxicity | High TPT | 1.0000 |
| Honey Bee Toxicity | High HBT | 0.8483 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | II | 0.7369 |
| Carcinogenicity (Three-class) | Non-required | 0.6192 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -6.8317 | LogS |
| Caco-2 Permeability | 1.6705 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.8588 | LD50, mol/kg |
| Fish Toxicity | -1.0555 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.9734 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Citrus fruits | 0110000 | European Union | 0.05 | 05/06/2018 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05 | 05/06/2018 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05 | 05/06/2018 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05 | 05/06/2018 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05 | 05/06/2018 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05 | 05/06/2018 | |
| Others (2) | 0110990 | European Union | 0.05 | 05/06/2018 | |
| Tree nuts | 0120000 | European Union | 0.05 | 05/06/2018 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05 | 05/06/2018 | |
| Brazil nuts | 0120020 | European Union | 0.05 | 05/06/2018 | |
| Cashew nuts | 0120030 | European Union | 0.05 | 05/06/2018 | |
| Chestnuts | 0120040 | European Union | 0.05 | 05/06/2018 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05 | 05/06/2018 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05 | 05/06/2018 | |
| Macadamias | 0120070 | European Union | 0.05 | 05/06/2018 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05 | 05/06/2018 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.05 | 05/06/2018 | |
| Pistachios | 0120100 | European Union | 0.05 | 05/06/2018 | |
| Walnuts | 0120110 | European Union | 0.05 | 05/06/2018 | |
| Others (2) | 0120990 | European Union | 0.05 | 05/06/2018 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The impacts of modern-use pesticides on shrimp aquaculture: An assessment for north eastern Australia. | Ecotoxicol Environ Saf | 2018 Feb | 29190596 |
| Comparison of subacute effects of two types of pyrethroid insecticides using metabolomics methods. | Pestic Biochem Physiol | 2017 Nov | 29183587 |
| Evaluation of various soaking agents as a novel tool for pesticide residues mitigation from cauliflower (<i>Brassica oleracea</i> var. <i>botrytis</i>). | J Food Sci Technol | 2016 Aug | 27784925 |
| Characteristics of suspended solids affect bifenthrin toxicity to the calanoid copepods Eurytemora affinis and Pseudodiaptomus forbesi. | Environ Toxicol Chem | 2015 Oct | 25939857 |
| Effect of Chinese traditional cooking on eight pesticides residue during cowpea processing. | Food Chem | 2015 Mar 1 | 25306325 |
| A comparison of the sublethal and lethal toxicity of four pesticides in Hyalella azteca and Chironomus dilutus. | Environ Sci Pollut Res Int | 2015 Aug | 25804662 |
| Relative toxicity of bifenthrin to Hyalella azteca in 10 day versus 28 day exposures. | Integr Environ Assess Manag | 2015 Apr | 25564769 |
| Fenpropathrin biodegradation pathway in Bacillus sp. DG-02 and its potential for bioremediation of pyrethroid-contaminated soils. | J Agric Food Chem | 2014 Mar 12 | 24576059 |
| Monitoring of some pesticides residue in consumed tea in Tehran market. | Iranian J Environ Health Sci Eng | 2013 Jan 12 | 23369650 |
| Pyrethroids in human breast milk: occurrence and nursing daily intake estimation. | Environ Int | 2012 Oct 15 | 22717642 |
| A sensitive and selective method for the determination of selected pesticides in fruit by gas chromatography/mass spectrometry with negative chemical ionization. | J Chromatogr A | 2012 Nov 16 | 23058941 |
| Pyrethroid insecticides in urban salmon streams of the Pacific Northwest. | Environ Pollut | 2011 Oct | 21592636 |
| Toxicity of synthetic pyrethroid insecticides to the grass shrimp, Palaemonetes pugio, parasitized with the bopyrid isopod, Probopyrus pandalicola. | J Environ Sci Health B | 2009 Nov | 20183094 |
| PolicosanolPlus and Neuroprevin ameliorate pesticide-mediated inhibition of neurite outgrowth and neurite degeneration. | Med Sci Monit | 2006 Dec | 17136002 |