Propoxur
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Basic Info
| Common Name | Propoxur(F04025) |
| 2D Structure | |
| Description | Propoxur 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 | F04025 |
| CAS Number | 114-26-1 |
| PubChem CID | 4944 |
| Formula | C11H15NO3 |
| IUPAC Name | (2-propan-2-yloxyphenyl) N-methylcarbamate |
| InChI Key | ISRUGXGCCGIOQO-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H15NO3/c1-8(2)14-9-6-4-5-7-10(9)15-11(13)12-3/h4-8H,1-3H3,(H,12,13) |
| Canonical SMILES | CC(C)OC1=CC=CC=C1OC(=O)NC |
| Isomeric SMILES | CC(C)OC1=CC=CC=C1OC(=O)NC |
| Synonyms |
2-Isopropoxyphenyl methylcarbamate
propoxur
Baygon
114-26-1
Aprocarb
Propoxure
Sendran
Propoxylor
Blattanex
Blattosep
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenol ethers |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenol ethers |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenoxy compound - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Carboximidic acid derivative - Ether - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organooxygen compound - Organonitrogen compound - Imine - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 209.245 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 206 |
| Monoisotopic Mass | 209.105 |
| Exact Mass | 209.105 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.8898 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7233 |
| P-glycoprotein Substrate | Non-substrate | 0.8042 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8782 |
| Non-inhibitor | 0.9417 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9282 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8144 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7649 |
| CYP450 2D6 Substrate | Substrate | 0.6328 |
| CYP450 3A4 Substrate | Substrate | 0.5980 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5300 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9308 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9322 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8179 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9169 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7127 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9845 |
| Non-inhibitor | 0.9460 | |
| AMES Toxicity | AMES toxic | 0.9078 |
| Carcinogens | Non-carcinogens | 0.8620 |
| Fish Toxicity | High FHMT | 0.9039 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8033 |
| Honey Bee Toxicity | High HBT | 0.8046 |
| Biodegradation | Not ready biodegradable | 0.8638 |
| Acute Oral Toxicity | I | 0.7808 |
| Carcinogenicity (Three-class) | Non-required | 0.6156 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.1209 | LogS |
| Caco-2 Permeability | 1.5274 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.4639 | LD50, mol/kg |
| Fish Toxicity | 1.0695 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0522 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Mandarins (Inc Clementines & Similar Hybrids) | Britain | 0. 3mg/kg | |||
| Lettuce(Including Cos Lettuce And Leaf Lettuce) | Japan | 2ppm | |||
| Egg Plant | Japan | 2ppm | |||
| Leaves & Stems Of Brassica | Britain | 0.05mg/kg | |||
| Other Small Fruit & Berries (Other Than Wild) | Britain | 0.05mg/kg | |||
| Almonds | Britain | 0.05mg/kg | |||
| Pumpkin(Including Squash) | Japan | 2ppm | |||
| Other Liliaceous Vegetables | Japan | 2ppm | |||
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 01/09/2008 | |
| 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* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.3 | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.3 | 01/09/2008 | |
| 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 | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.05* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.05* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.05* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Preparation of a magnetic porous carbon with hierarchical structures from wastebiomass for the extraction of some carbamates. | J Sep Sci | 2017 Jun | 28383818 |
| Mechanisms of acaricide resistance in the cattle tick Rhipicephalus (Boophilus)microplus in Sri Lanka. | Pestic Biochem Physiol | 2017 Jun | 28595924 |
| Simultaneous determination of pesticide residues and antioxidants in blended oil using a liquid-liquid extraction combined with dispersive solid phase extraction method. | Food Chem | 2017 Aug 15 | 28372183 |
| Kinetic studies of the reaction between pesticides and hydroxyl radical generatedby laser flash photolysis. | J Sci Food Agric | 2016 Mar 30 | 25974279 |
| Multiresidue pesticide analysis in nutraceuticals from green tea extracts bycomprehensive two-dimensional gas chromatography with time-of-flight massspectrometry. | J Chromatogr A | 2015 May 22 | 25865796 |
| Determination of five pesticides in juice, fruit and vegetable samples by meansof liquid chromatography combined with multivariate curve resolution. | Anal Chim Acta | 2014 Mar 3 | 24528840 |
| Sensitive bi-enzymatic biosensor based on polyphenoloxidases-goldnanoparticles-chitosan hybrid film-graphene doped carbon paste electrode forcarbamates detection. | Bioelectrochemistry | 2014 Aug | 24642204 |
| Ensuring selectivity and sensitivity by timed- and ultra-selective reactionmonitoring during gas chromatography-tandem mass spectrometric determination ofpesticides. | J Chromatogr A | 2013 Nov 29 | 24161146 |
| A pilot survey of 39 Victorian WWTP effluents using a high speed luminescent umu test in conjunction with a novel GC-MS-database technique for automaticidentification of micropollutants. | Water Sci Technol | 2012 | 22766865 |
| Effect of cooking process on the residues of three carbamate pesticides in rice. | Iran J Pharm Res | 2011 Winter | 24363690 |
| A pilot study of pesticides and PCBs in the breast milk of women residing inurban and agricultural communities of California. | J Environ Monit | 2011 Nov | 22009134 |
| Sequential injection-bead injection-lab-on-valve coupled to high-performanceliquid chromatography for online renewable micro-solid-phase extraction ofcarbamate residues in food and environmental samples. | J Sep Sci | 2011 Jul | 21557471 |
| Efficacy of imidacloprid and fipronil gels over synthetic pyrethroid and propoxuraerosols in control of German cockroaches (Dictyoptera: Blatellidae). | J Vector Borne Dis | 2010 Mar | 20231772 |
| Effects of aldicarb and propoxur on cytotoxicity and lipid peroxidation in CHO-K1cells. | Food Chem Toxicol | 2010 Jun | 20346998 |
| Cloud-point extraction and reversed-phase high-performance liquid chromatography for the determination of carbamate insecticide residues in fruits. | Anal Bioanal Chem | 2009 Jul | 19242683 |
| Sequential injection kinetic spectrophotometric determination of quaternarymixtures of carbamate pesticides in water and fruit samples using artificialneural networks for multivariate calibration. | Spectrochim Acta A Mol Biomol Spectrosc | 2009 Dec | 19864181 |
| Atmospheric pressure glow discharge desorption mass spectrometry for rapidscreening of pesticides in food. | Rapid Commun Mass Spectrom | 2008 Sep | 18697232 |
| Analysis of phenoxyl-type N-methylcarbamate pesticide residues in vegetables bycapillary zone electrophoresis with pre-column hydrolysis and amperometricdetection. | J Chromatogr Sci | 2008 Aug | 18718137 |
| Toxicity of Myristica fagrans seed compounds against Blattella germanica (Dictyoptera: Blattellidae). | J Med Entomol | 2007 May | 17547241 |
| Penetration studies of propoxur and phoxim from eggshell into whole egg afterexperimental exposure and application in henhouses. | J Agric Food Chem | 2007 Jul 25 | 17602660 |
Targets
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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 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:
- Protease binding
- Specific Function:
- Complexes with metalloproteinases (such as collagenases) and irreversibly inactivates them by binding to their catalytic zinc cofactor. Known to act on MMP-1, MMP-2, MMP-3, MMP-7, MMP-8, MMP-9, MMP-10, MMP-13, MMP-14, MMP-15, MMP-16 and MMP-19.
- Gene Name:
- TIMP2
- Uniprot ID:
- P16035
- Molecular Weight:
- 24398.995 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 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:
- Cytokine activity
- Specific Function:
- Cytokine that affects the growth, movement, or activation state of cells that participate in immune and inflammatory response. Chemotactic for activated T-cells. Binds to CXCR3.
- Gene Name:
- CXCL9
- Uniprot ID:
- Q07325
- Molecular Weight:
- 14018.72 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:
- ICAM proteins are ligands for the leukocyte adhesion protein LFA-1 (integrin alpha-L/beta-2). During leukocyte trans-endothelial migration, ICAM1 engagement promotes the assembly of endothelial apical cups through ARHGEF26/SGEF and RHOG activation.(Microbial infection) Acts as a receptor for major receptor group rhinovirus A-B capsid proteins (PubMed:1968231, PubMed:2538243). Acts as a receptor for Coxsackievirus A21 capsid proteins (PubMed:11160747, PubMed:16004874, PubMed:9539703). Upon Kaposi's sarcoma-associated herpesvirus/HHV-8 infection, is degraded by viral E3 ubiquitin ligase MIR2, presumably to prevent lysis of infected cells by cytotoxic T-lymphocytes and NK cell (PubMed:11413168).
- Gene Name:
- ICAM1
- Uniprot ID:
- P05362
- Molecular Weight:
- 57824.785 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:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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:
- Protein homodimerization activity
- Specific Function:
- Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
- Gene Name:
- CSF1
- Uniprot ID:
- P09603
- Molecular Weight:
- 60178.885 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 ]