Pyriproxyfen
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Basic Info
| Common Name | Pyriproxyfen(F05132) |
| 2D Structure | |
| Description | Pyriproxyfen is a pyridine-based pesticide which is found to be effective against a variety of arthropoda. It was introduced to the US in 1996, to protect cotton crops against whitefly. It has also been found useful for protecting other crops. It is also used as a prevention for fleas on household pets. |
| FRCD ID | F05132 |
| CAS Number | 95737-68-1 |
| PubChem CID | 91753 |
| Formula | C20H19NO3 |
| IUPAC Name | 2-[1-(4-phenoxyphenoxy)propan-2-yloxy]pyridine |
| InChI Key | NHDHVHZZCFYRSB-UHFFFAOYSA-N |
| InChI | InChI=1S/C20H19NO3/c1-16(23-20-9-5-6-14-21-20)15-22-17-10-12-19(13-11-17)24-18-7-3-2-4-8-18/h2-14,16H,15H2,1H3 |
| Canonical SMILES | CC(COC1=CC=C(C=C1)OC2=CC=CC=C2)OC3=CC=CC=N3 |
| Isomeric SMILES | CC(COC1=CC=C(C=C1)OC2=CC=CC=C2)OC3=CC=CC=N3 |
| Synonyms |
4-Phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether
Pyriproxyfen
95737-68-1
2-[1-Methyl-2-(4-phenoxyphenoxy)ethoxy]pyridine
Pyriproxifen
2-((1-(4-Phenoxyphenoxy)propan-2-yl)oxy)pyridine
Pyriproxyfen [ISO:BSI]
HSDB 7053
OMS 3019
2-(1-Methyl-2-(4-phenoxyphenoxy)ethoxy)pyridine
|
| 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 heteromonocyclic compounds |
| Substituents | Diphenylether - Diaryl ether - Phenoxy compound - Phenol ether - Alkyl aryl ether - Pyridine - Heteroaromatic compound - Ether - Organoheterocyclic compound - Azacycle - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic heteromonocyclic 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 | 321.376 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Complexity | 338 |
| Monoisotopic Mass | 321.136 |
| Exact Mass | 321.136 |
| XLogP | 4.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| 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+ | 0.9933 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6574 |
| P-glycoprotein Substrate | Non-substrate | 0.7298 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7942 |
| Non-inhibitor | 0.9536 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7765 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8262 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7913 |
| CYP450 2D6 Substrate | Non-substrate | 0.6665 |
| CYP450 3A4 Substrate | Substrate | 0.5525 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7328 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6109 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8974 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5351 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8889 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6506 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9850 |
| Non-inhibitor | 0.9033 | |
| AMES Toxicity | AMES toxic | 0.5104 |
| Carcinogens | Non-carcinogens | 0.9257 |
| Fish Toxicity | Low FHMT | 0.9309 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.5327 |
| Honey Bee Toxicity | Low HBT | 0.6064 |
| Biodegradation | Not ready biodegradable | 0.6345 |
| Acute Oral Toxicity | III | 0.8236 |
| Carcinogenicity (Three-class) | Non-required | 0.4862 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2383 | LogS |
| Caco-2 Permeability | 1.3991 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8390 | LD50, mol/kg |
| Fish Toxicity | 1.4555 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1497 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Walnut | Japan | 0.1ppm | |||
| Almond | Japan | 0.02ppm | |||
| Pecan | Japan | 0.02ppm | |||
| Chestnut | Japan | 0.02ppm | |||
| Ginkgo Nut | Japan | 0.1ppm | |||
| Lemon | Japan | 0.5ppm | |||
| Other Vegetables | Japan | 1ppm | |||
| Kidney Beans,Immature(With Pods) | Japan | 0.2ppm | |||
| Tomatoes | Canada | 0. 25mg/kg | |||
| Cottonseed Oil | Japan | 0.01ppm | |||
| Mineral Waters | Japan | 0.3ppm | |||
| Milk | Japan | 0.02ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.01ppm | |||
| Pig,Edible Offal | Japan | 0.02ppm | |||
| Cattle,Edible Offal | Japan | 0.01ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.01ppm | |||
| Pig,Kidney | Japan | 0.02ppm | |||
| Cattle,Kidney | Japan | 0.01ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.01ppm | |||
| Pig,Liver | Japan | 0.02ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Evaluation of Pyrethroid Insecticides and Insect Growth Regulators Applied toDifferent Surfaces for Control of Trogoderma granarium (Coleoptera: Dermestidae) the Khapra Beetle. | J Econ Entomol | 2018 Apr 2 | 29514245 |
| Bioconcentration and Metabolism of Pyriproxyfen in Tadpoles of African ClawedFrogs, Xenopus laevis. | J Agric Food Chem | 2017 Nov 22 | 29084385 |
| Compatibility of insecticides and fungicides with the zoophytophagous miridpredator Nesidiocoris tenuis. | PLoS One | 2017 Nov 2 | 29095873 |
| Enantioselective dissipation of pyriproxyfen in soils and sand. | Chirality | 2017 Jul | 28517365 |
| Occurrence of pesticide residues in Spanish beeswax. | Sci Total Environ | 2017 Dec 15 | 28679118 |
| Comparative susceptibility of two Neotropical predators, Eriopis connexa and Chrysoperla externa, to acetamiprid and pyriproxyfen: Short and long-term effects after egg exposure. | Environ Pollut | 2017 Dec | 28915542 |
| Evaluating the Effect of Environmental Chemicals on Honey Bee Development fromthe Individual to Colony Level. | J Vis Exp | 2017 Apr 1 | 28447982 |
| Enantiomeric Separations of Pyriproxyfen and its Six Chiral Metabolites byHigh-Performance Liquid Chromatography. | Chirality | 2016 Mar | 26773961 |
| Larval Exposure to the Juvenile Hormone Analog Pyriproxyfen Disrupts Acceptanceof and Social Behavior Performance in Adult Honeybees. | PLoS One | 2015 Jul 14 | 26171610 |
| Assessment of two extraction methods to determine pesticides in soils, sediments and sludges. Application to the Túria River Basin. | J Chromatogr A | 2015 Jan 23 | 25573188 |
| Multifamily determination of pesticide residues in soya-based nutraceuticalproducts by GC/MS-MS. | Food Chem | 2015 Apr 15 | 25466092 |
| Bemisia tabaci females from the Mediterranean (Q) species detect and avoid layingeggs in the presence of pyriproxyfen, a juvenile hormone analogue. | Pest Manag Sci | 2014 Oct | 24375924 |
| Patterns of presence and concentration of pesticides in fish and waters of theJúcar River (Eastern Spain). | J Hazard Mater | 2014 Jan 30 | 24315814 |
| In-package nonthermal plasma degradation of pesticides on fresh produce. | J Hazard Mater | 2014 Apr 30 | 24598029 |
| Residue behaviour of six pesticides in button crimini during home canning. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24761834 |
| Influence of the matrix in bioavailability of flufenoxuron, lufenuron,pyriproxyfen and fenoxycarb residues in grapes and wine. | Food Chem Toxicol | 2013 Oct | 23941774 |
| Triatomicidal effect of new spot-on formulations applied to poultry in semi-fieldconditions. | Parasitol Res | 2013 Jan | 23001549 |
| Variability of pesticide dissipation half-lives in plants. | Environ Sci Technol | 2013 Apr 16 | 23521068 |
| Evaluation of three feed-through insecticides using two rodent and two sand flyspecies as models. | J Am Mosq Control Assoc | 2012 Sep | 23833909 |
| Combined effects of temperature and pyriproxyfen stress in a full life-cycle testwith Chironomus riparius (Insecta). | Environ Toxicol Chem | 2012 Oct | 22865670 |
Targets
- General Function:
- Prostaglandin e receptor activity
- Specific Function:
- Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
- Gene Name:
- PTGER2
- Uniprot ID:
- P43116
- Molecular Weight:
- 39759.945 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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:
- Primary amine oxidase activity
- Specific Function:
- Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and signal transduction. The VCAM1/ITGA4/ITGB1 interaction may play a pathophysiologic role both in immune responses and in leukocyte emigration to sites of inflammation.
- Gene Name:
- VCAM1
- Uniprot ID:
- P19320
- Molecular Weight:
- 81275.43 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 ]
- General Function:
- Xenobiotic-transporting atpase activity
- Specific Function:
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. Implicated in the efflux of numerous drugs and xenobiotics: mitoxantrone, the photosensitizer pheophorbide, camptothecin, methotrexate, azidothymidine (AZT), and the anthracyclines daunorubicin and doxorubicin.
- Gene Name:
- ABCG2
- Uniprot ID:
- Q9UNQ0
- Molecular Weight:
- 72313.47 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:
- 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 ]