Fenamiphos
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Basic Info
| Common Name | Fenamiphos(F05066) |
| 2D Structure | |
| Description | Fenamiphos is an organophosphate acetylcholinesterase inhibitor insecticide (nematicide) used to control a wide variety of nematode (round worm) pests. Nematodes can live as parasites on or within a plant. They may be free living or associated with cyst and root-knot formations in plants. Fenamiphos is used on a variety of plants including tobacco, cocoa, turf, bananas, pineapples, citrus and other fruit vines, and on some vegetables and grains. The compound is absorbed by the roots and is then transported throughout the plant. Fenamiphos, similar to other organophosphates, blocks the enzyme acetyl cholinesterase in the target pest. The enzyme regulates inter-cellular activity. The pesticide is also active against non-target invertebrates such as sucking insects and spider mites. |
| FRCD ID | F05066 |
| CAS Number | 22224-92-6 |
| PubChem CID | 31070 |
| Formula | C13H22NO3PS |
| IUPAC Name | N-[ethoxy-(3-methyl-4-methylsulfanylphenoxy)phosphoryl]propan-2-amine |
| InChI Key | ZCJPOPBZHLUFHF-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15) |
| Canonical SMILES | CCOP(=O)(NC(C)C)OC1=CC(=C(C=C1)SC)C |
| Isomeric SMILES | CCOP(=O)(NC(C)C)OC1=CC(=C(C=C1)SC)C |
| Wikipedia | Fenamiphos |
| Synonyms |
FENAMIPHOS
Phenamiphos
Nemacur
22224-92-6
Nemacur P
Methaphenamiphos
BAY sra 3886
Fenamiphos [BSI:ISO]
BAY 68138
Caswell No. 453A
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenoxy compounds |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenoxy compounds |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenoxy compound - Aryl thioether - Thiophenol ether - Phosphoric diester monoamide - Toluene - Alkylarylthioether - Organic phosphoric acid derivative - Phosphoric acid ester - Organic phosphoric acid amide - Sulfenyl compound - Thioether - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Organooxygen compound - Organic oxide - Organonitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 303.357 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Complexity | 314 |
| Monoisotopic Mass | 303.106 |
| Exact Mass | 303.106 |
| XLogP | 3.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9121 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5216 |
| P-glycoprotein Substrate | Non-substrate | 0.8404 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6326 |
| Non-inhibitor | 0.9587 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8877 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7909 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8215 |
| CYP450 2D6 Substrate | Non-substrate | 0.6801 |
| CYP450 3A4 Substrate | Substrate | 0.5597 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6919 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6127 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8647 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6161 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8022 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6644 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9301 |
| Non-inhibitor | 0.8129 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.6741 |
| Fish Toxicity | High FHMT | 0.9057 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8274 |
| Honey Bee Toxicity | High HBT | 0.8934 |
| Biodegradation | Not ready biodegradable | 0.9786 |
| Acute Oral Toxicity | I | 0.7933 |
| Carcinogenicity (Three-class) | Non-required | 0.5742 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4157 | LogS |
| Caco-2 Permeability | 1.0754 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.5478 | LD50, mol/kg |
| Fish Toxicity | 1.3693 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1183 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Ware Potatoes | Britain | 0.02mg/kg | |||
| Wild Mushrooms | Britain | 0.02mg/kg | |||
| Chervil | Britain | 0.02mg/kg | |||
| Brussels Sprouts | Britain | 0.05mg/kg | |||
| Aubergines | Britain | 0.05mg/kg | |||
| Chili Peppers | Britain | 0.1mg/kg | |||
| Peppers | Britain | 0.1mg/kg | |||
| Tomatoes | Britain | 0.05mg/kg | |||
| Other Miscellaneous Fruit | Britain | 0.02mg/kg | |||
| Other Cane Fruit (Other Than Wild) | Britain | 0.02mg/kg | |||
| Other Citrus Fruit | Britain | 0.02mg/kg | |||
| Other Poultry Animals,Edible Offal | Japan | 0.01ppm | |||
| Other Fruits | Japan | 0.02ppm | |||
| Japanese Plum(Including Prune) | Japan | 0.02ppm | |||
| Kidney Beans,Immature(With Pods) | Japan | 0.02ppm | |||
| Other Umbelliferous Vegetables | Japan | 0.1ppm | |||
| Mitsuba | Japan | 0.02ppm | |||
| Celery | Japan | 0.04ppm | |||
| Parsley | Japan | 0.02ppm | |||
| Parsnip | Japan | 0.1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effects of biochar amendment on sorption, dissipation, and uptake of fenamiphosand cadusafos nematicides in sandy soil. | Pest Manag Sci | 2018 May 15 | 29761623 |
| Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim. | Anal Chem | 2017 Mar 7 | 28264568 |
| Children's diets, pesticide uptake, and implications for risk assessment: AnIsraeli case study. | Food Chem Toxicol | 2016 Jan | 26585921 |
| Organophosphate pesticide method development and presence of chlorpyrifos in the feet of nearctic-neotropical migratory songbirds from Canada that over-winter in Central America agricultural areas. | Chemosphere | 2016 Feb | 26421621 |
| Novel restricted access materials combined to molecularly imprinted polymers for selective solid-phase extraction of organophosphorus pesticides from honey. | Food Chem | 2015 Nov 15 | 25977034 |
| Behavior of Multiclass Pesticide Residue Concentrations during the Transformationfrom Rose Petals to Rose Absolute. | J Agric Food Chem | 2015 May 27 | 25942486 |
| Pesticide and trace metal occurrence and aquatic benchmark exceedances in surfacewaters and sediments of urban wetlands and retention ponds in Melbourne,Australia. | Environ Sci Pollut Res Int | 2015 Jul | 25697552 |
| Enantiomeric discrimination and quantification of the chiral organophosphoruspesticide fenamiphos in aqueous samples by a novel and selective ³¹P nuclearmagnetic resonance spectroscopic method using cyclodextrins as chiral selector. | J Agric Food Chem | 2011 Feb 9 | 21192704 |
| Separation of organophosphorus pesticides by using nano-liquid chromatography. | J Chromatogr A | 2009 May 1 | 19321170 |
| Multiwalled carbon nanotubes as solid-phase extraction materials for the gaschromatographic determination of organophosphorus pesticides in waters. | J Sep Sci | 2008 Oct | 18837477 |
| Multi-walled carbon nanotubes as efficient solid-phase extraction materials oforganophosphorus pesticides from apple, grape, orange and pineapple fruit juices. | J Chromatogr A | 2008 Nov 21 | 18849040 |
| Toxicity and transformation of fenamiphos and its metabolites by two micro algae Pseudokirchneriella subcapitata and Chlorococcum sp. | Sci Total Environ | 2008 Jul 15 | 18452972 |
| Evaluation of pesticide residue in grape juices and the effect of naturalantioxidants on their degradation rate. | Anal Bioanal Chem | 2007 Nov | 17641884 |
| Survey of carbamate and organophosphorous pesticide export from a south Florida(U.S.A.) agricultural watershed: implications of sampling frequency on ecologicalrisk estimation. | Environ Toxicol Chem | 2006 Nov | 17089706 |
| Determination of pesticides by solid phase extraction followed by gaschromatography with nitrogen-phosphorous detection in natural water andcomparison with solvent drop microextraction. | Anal Bioanal Chem | 2006 Feb | 16402179 |
| Management of root knot nematodes in turfgrass using mustard formulations andbiostimulants. | Commun Agric Appl Biol Sci | 2006 | 17390806 |
| Investigation of alternatives to methyl bromide for management of Meloidogynejavanica on greenhouse grown tomato. | Pest Manag Sci | 2003 Dec | 14667053 |
| Evaluation of pesticide uptake by Lupinus seeds. | Water Res | 2003 Aug | 12834741 |
| Gas chromatography with pulsed flame photometric detection multiresidue methodfor organophosphate pesticide and metabolite residues at the parts-per-billionlevel in representatives commodities of fruits and vegetable crop groups. | J AOAC Int | 2001 May-Jun | 11417651 |
| Microwave-assisted extraction method for the determination of atrazine and fourorganophosphorus pesticides in oranges by gas chromatography (GC). | Fresenius J Anal Chem | 2000 Jun | 11227461 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [21115097 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d 24-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
- Specific Function:
- Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
- Gene Name:
- NFE2L2
- Uniprot ID:
- Q16236
- Molecular Weight:
- 67825.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]