Fenoxycarb
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Basic Info
| Common Name | Fenoxycarb(F03996) |
| 2D Structure | |
| Description | Fenoxycarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795) |
| FRCD ID | F03996 |
| CAS Number | 72490-01-8 |
| PubChem CID | 51605 |
| Formula | C17H19NO4 |
| IUPAC Name | ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate |
| InChI Key | HJUFTIJOISQSKQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H19NO4/c1-2-20-17(19)18-12-13-21-14-8-10-16(11-9-14)22-15-6-4-3-5-7-15/h3-11H,2,12-13H2,1H3,(H,18,19) |
| Canonical SMILES | CCOC(=O)NCCOC1=CC=C(C=C1)OC2=CC=CC=C2 |
| Isomeric SMILES | CCOC(=O)NCCOC1=CC=C(C=C1)OC2=CC=CC=C2 |
| Synonyms |
Ethyl (2-(4-phenoxyphenoxy)ethyl)carbamate
FENOXYCARB
72490-01-8
Insegar
Varikill
Logic
Pictyl
Pyctyl
Torus
Fenoxycarb [ANSI]
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Diphenylethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diphenylethers |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Diphenylether - Diaryl ether - Phenoxy compound - Phenol ether - Alkyl aryl ether - Carbamic acid ester - Carbonic acid derivative - Ether - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 301.342 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 8 |
| Complexity | 310 |
| Monoisotopic Mass | 301.131 |
| Exact Mass | 301.131 |
| XLogP | 4.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.8556 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5873 |
| P-glycoprotein Substrate | Non-substrate | 0.5266 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5444 |
| Non-inhibitor | 0.7074 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7243 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7327 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7564 |
| CYP450 2D6 Substrate | Non-substrate | 0.6852 |
| CYP450 3A4 Substrate | Non-substrate | 0.5000 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5970 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7752 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.6650 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5084 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5875 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8337 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7207 |
| Non-inhibitor | 0.6694 | |
| AMES Toxicity | Non AMES toxic | 0.7180 |
| Carcinogens | Non-carcinogens | 0.9041 |
| Fish Toxicity | High FHMT | 0.9161 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9844 |
| Honey Bee Toxicity | High HBT | 0.5620 |
| Biodegradation | Not ready biodegradable | 0.7350 |
| Acute Oral Toxicity | IV | 0.6293 |
| Carcinogenicity (Three-class) | Non-required | 0.6130 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.6373 | LogS |
| Caco-2 Permeability | 0.9719 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.2852 | LD50, mol/kg |
| Fish Toxicity | 1.1731 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2220 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Tree nuts | 0120000 | European Union | 0.05* | 26/04/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 26/04/2016 | |
| 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* | 26/04/2016 | |
| 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* | 26/04/2016 | |
| Beans (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, Ervils/lenti... | 0300010 | European Union | 0.05* | 26/04/2016 | |
| Potato | Japan | 0.05ppm | |||
| Hop | Japan | 0.05ppm | |||
| Sugar Beet | Japan | 0.05ppm | |||
| Citrus fruits | 0110000 | European Union | 2 | 26/04/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 2 | 26/04/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 2 | 26/04/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 2 | 26/04/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 2 | 26/04/2016 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 2 | 26/04/2016 | |
| Others (2) | 0110990 | European Union | 2 | 26/04/2016 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 26/04/2016 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 26/04/2016 | |
| Chestnuts | 0120040 | European Union | 0.05* | 26/04/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 26/04/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 26/04/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of neonicotinoid insecticides and insect growthregulators residues in honey using LC-MS/MS with anion exchanger-disposablepipette extraction. | J Chromatogr A | 2018 Jul 6 | 29735281 |
| Secondary biomarkers of insecticide-induced stress of honey bee colonies andtheir relevance for overwintering strength. | Ecotoxicol Environ Saf | 2016 Oct | 27376353 |
| Kinetic studies of the reaction between pesticides and hydroxyl radical generatedby laser flash photolysis. | J Sci Food Agric | 2016 Mar 30 | 25974279 |
| Evaluating exposure and potential effects on honeybee brood (Apis mellifera) development using glyphosate as an example. | Integr Environ Assess Manag | 2014 Jul | 24616275 |
| Influence of the matrix in bioavailability of flufenoxuron, lufenuron,pyriproxyfen and fenoxycarb residues in grapes and wine. | Food Chem Toxicol | 2013 Oct | 23941774 |
| Efficacy of insect growth regulators as grain protectants against twostored-product pests in wheat and maize. | J Food Prot | 2012 May | 22564945 |
| Bioavailability of insect growth regulator residues in citrus. | Ecotoxicology | 2009 Nov | 19636704 |
| Effects of sublethal doses of crop protection agents on honey bee (Apismellifera) global colony vitality and its potential link with aberrant foragingactivity. | Commun Agric Appl Biol Sci | 2009 | 20218533 |
| Solid-phase microextraction-liquid chromatography-mass spectrometry applied tothe analysis of insecticides in honey. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2008Jan | 17852391 |
| Sublethal effects of crop protection on honey bee pollination: foraging behaviour and flower visits. | Commun Agric Appl Biol Sci | 2008 | 19226779 |
| Dissipation of fenoxycarb and pyriproxyfen in fresh and canned peach. | J Environ Sci Health B | 2007 Sep-Oct | 17763032 |
| Safe apples for baby-food production: survey of pesticide treatment regimesleaving minimum residues. | Food Addit Contam | 2007 Jun | 17487602 |
| Ovicidal and larvicidal effectiveness of insecticides applied by dipping appleson the small fruit tortrix Grapholita lobarzewskii. | Pest Manag Sci | 2007 Jul | 17503401 |
| Bioavailability of insect growth regulators in citrus and stone fruits. | Commun Agric Appl Biol Sci | 2007 | 18399436 |
| Dissipation of insect growth regulators in fresh orange and orange juice. | Commun Agric Appl Biol Sci | 2007 | 18399437 |
| The screening of chemicals for juvenoid-related endocrine activity using thewater flea Daphnia magna. | Aquat Toxicol | 2005 Sep 10 | 16046008 |
| Long-term effects of fenoxycarb on two mayfly species in artificial indoorstreams. | Ecotoxicol Environ Saf | 2004 Jun | 15157579 |
| Evaluation of an enzyme immunoassay for the detection of the insect growthregulator fenoxycarb in environmental and biological samples. | Pest Manag Sci | 2003 Apr | 12701701 |
| Synthesis of haptens and protein conjugates for the development of immunoassaysfor the insect growth regulator fenoxycarb. | J Agric Food Chem | 2002 Jan 2 | 11754538 |
| Food concentration affects the life history response of Ceriodaphnia cf. dubia tochemicals with different mechanisms of action. | Ecotoxicol Environ Saf | 2002 Feb | 11886184 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
- Mechanism of Action:
- Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- 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:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 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:
- This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
- Gene Name:
- CYP2J2
- Uniprot ID:
- P51589
- Molecular Weight:
- 57610.165 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:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 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:
- Virus receptor activity
- Specific Function:
- Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a receptor for vesicular stomatitis virus (PubMed:23589850). In case of HIV-1 infection, may function as a receptor for extracellular Tat in neurons, mediating its internalization in uninfected cells (PubMed:11100124).
- Gene Name:
- LDLR
- Uniprot ID:
- P01130
- Molecular Weight:
- 95375.105 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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 binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 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 ]