Phorate
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Basic Info
| Common Name | Phorate(F03440) |
| 2D Structure | |
| Description | Phorate is an organophosphate insecticide and acaricide that controls pests by systemic, contact, and fumigant action. It is used against sucking and chewing insects, leafhoppers, leafminers, mites, some nematodes and rootworms. Phorate is used in pine forests and on root and field crops, including corn, cotton, coffee, some ornamental and herbaceous plants and bulbs. Phorate is extremely toxic; it is a Restricted Use Pesticide (RUP) and is among the most poisonous chemicals commonly used for pest control. (L1186) |
| FRCD ID | F03440 |
| CAS Number | 298-02-2 |
| PubChem CID | 4790 |
| Formula | C7H17O2PS3 |
| IUPAC Name | diethoxy-(ethylsulfanylmethylsulfanyl)-sulfanylidene-$l^{5}-phosphane |
| InChI Key | BULVZWIRKLYCBC-UHFFFAOYSA-N |
| InChI | InChI=1S/C7H17O2PS3/c1-4-8-10(11,9-5-2)13-7-12-6-3/h4-7H2,1-3H3 |
| Canonical SMILES | CCOP(=S)(OCC)SCSCC |
| Isomeric SMILES | CCOP(=S)(OCC)SCSCC |
| Synonyms |
phorate
Thimet
Granutox
Agrimet
Timet
298-02-2
Thimenox
Geomet
Vegfru
Thimet 10G
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic dithiophosphoric acids and derivatives |
| Subclass | Dithiophosphate O-esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dithiophosphate O-esters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dithiophosphate o-ester - Dithiophosphate s-ester - Dialkylthioether - Sulfenyl compound - Thioether - Organothiophosphorus compound - Organic oxygen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 260.365 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 8 |
| Complexity | 156 |
| Monoisotopic Mass | 260.013 |
| Exact Mass | 260.013 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.9608 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5204 |
| P-glycoprotein Substrate | Non-substrate | 0.7840 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6862 |
| Non-inhibitor | 0.9283 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9174 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4891 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8192 |
| CYP450 2D6 Substrate | Non-substrate | 0.8349 |
| CYP450 3A4 Substrate | Non-substrate | 0.6364 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7947 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6968 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9094 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7289 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8352 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8040 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7816 |
| Non-inhibitor | 0.8899 | |
| AMES Toxicity | Non AMES toxic | 0.9288 |
| Carcinogens | Carcinogens | 0.7734 |
| Fish Toxicity | High FHMT | 0.8043 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6144 |
| Honey Bee Toxicity | High HBT | 0.9437 |
| Biodegradation | Not ready biodegradable | 0.8782 |
| Acute Oral Toxicity | I | 0.9705 |
| Carcinogenicity (Three-class) | Non-required | 0.6465 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0470 | LogS |
| Caco-2 Permeability | 1.0659 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 5.5297 | LD50, mol/kg |
| Fish Toxicity | 2.4547 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5196 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Hop | Britain | 0.1mg/kg | |||
| Tea | Britain | 0.1mg/kg | |||
| 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 | 0.02* | 26/04/2013 | |
| Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,) | 0153020 | European Union | 0.01* | 26/04/2013 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 0.01* | 26/04/2013 | |
| (b) tropical root and tuber vegetables | 0212000 | European Union | 0.01* | 26/04/2013 | |
| Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,) | 0212010 | European Union | 0.01* | 26/04/2013 | |
| (c) leafy brassica | 0243000 | European Union | 0.01* | 26/04/2013 | |
| Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,) | 0243010 | European Union | 0.01* | 26/04/2013 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.01* | 26/04/2013 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 26/04/2013 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 26/04/2013 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 26/04/2013 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 26/04/2013 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 26/04/2013 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 26/04/2013 | |
| Others (2) | 0110990 | European Union | 0.01* | 26/04/2013 | |
| Tree nuts | 0120000 | European Union | 0.02* | 26/04/2013 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 26/04/2013 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 26/04/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effects of pan cooking on micropollutants in meat. | Food Chem | 2017 Oct 1 | 28490090 |
| Metabonomic analysis of the protective effect of quercetin on the toxicity induced by mixture of organophosphate pesticides in rat urine. | Hum Exp Toxicol | 2017 May | 27251765 |
| Can herbicide safeners allow selective control of weedy rice infesting ricecrops? | Pest Manag Sci | 2017 Jan | 27484802 |
| Biodegradation of two organophosphorus pesticides in whole corn silage asaffected by the cultured Lactobacillus plantarum. | 3 Biotech | 2016 Jun | 28330143 |
| QuEChERS method for the simultaneous quantification of phorate and itsmetabolites in porcine and chicken muscle and table eggs using ultra-highperformance liquid chromatography with tandem mass spectrometry. | J Sep Sci | 2016 Jun | 27061785 |
| Quantum dot-DNA aptamer conjugates coupled with capillary electrophoresis: Auniversal strategy for ratiometric detection of organophosphorus pesticides. | Talanta | 2016 | 26695234 |
| Modified QuEChERS in combination with dispersive liquid-liquid microextractionbased on solidification of the floating organic droplet method for thedetermination of organophosphorus pesticides in milk samples. | J Chromatogr Sci | 2015 Nov-Dec | 26270080 |
| 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 |
| Synthesis of a New Bimetallic Re(I)-NCS-Pt(II) Complex as ChemodosimetricEnsemble for the Selective Detection of Mercapto-Containing Pesticides. | Anal Chem | 2015 Jun 16 | 26039794 |
| Susceptibility of nine organophosphorus pesticides in skimmed milk towardsinoculated lactic acid bacteria and yogurt starters. | J Sci Food Agric | 2015 Jan | 24777955 |
| Organophosphorus insecticides in honey, pollen and bees (Apis mellifera L.) and their potential hazard to bee colonies in Egypt. | Ecotoxicol Environ Saf | 2015 Apr | 25574845 |
| A disordered silver nanowires membrane for extraction and surface-enhanced Raman spectroscopy detection. | Analyst | 2014 May 21 | 24668444 |
| Organophosphorus pesticides detection using broad-specific single-stranded DNAbased fluorescence polarization aptamer assay. | Biosens Bioelectron | 2014 May 15 | 24384262 |
| Metabonomic analysis of the joint toxic action of long-term low-level exposure to a mixture of four organophosphate pesticides in rat plasma. | Mol Biosyst | 2014 May | 24626741 |
| Development of a single aptamer-based surface enhanced Raman scattering methodfor rapid detection of multiple pesticides. | Analyst | 2014 Apr 21 | 24551875 |
| Simultaneous determination of ten organophosphate pesticide residues in fruits bygas chromatography coupled with magnetic separation. | J Sep Sci | 2014 Apr | 24470377 |
| Pesticide residues in market foods in Shaanxi Province of China in 2010. | Food Chem | 2013 Jun 1 | 23411338 |
| Application of ultraperformance liquid chromatography/mass spectrometry-based metabonomic techniques to analyze the joint toxic action of long-term low-level exposure to a mixture of organophosphate pesticides on rat urine profile. | Toxicol Sci | 2013 Jul | 23580312 |
| A label-free silicon quantum dots-based photoluminescence sensor for ultrasensitive detection of pesticides. | Anal Chem | 2013 Dec 3 | 24160846 |
| Further studies on wireworm management in Canada: damage protection versuswireworm mortality in potatoes. | J Econ Entomol | 2013 Apr | 23786066 |
Targets
- 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
References
- Kashyap SK, Jani JP, Saiyed HN, Gupta SK: Clinical effects and cholinesterase activity changes in workers exposed to Phorate (Thimet). J Environ Sci Health B. 1984 Jun-Jul;19(4-5):479-89. [6470423 ]
- 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 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
- Henderson MC, Krueger SK, Siddens LK, Stevens JF, Williams DE: S-oxygenation of the thioether organophosphate insecticides phorate and disulfoton by human lung flavin-containing monooxygenase 2. Biochem Pharmacol. 2004 Sep 1;68(5):959-67. [15294458 ]
- 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:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 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 ]