Prometryn
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Prometryn(F05124) |
| 2D Structure | |
| Description | Prometryn is a selective herbicide which controls annual grasses and broadleaf weeds in a variety of crops including cotton and celery. It inhibits photosynthesis in susceptible species. Prometryn is available in wettable powder and liquid formulations. Prometryn is a slightly to moderately toxic compound which is classified as a member of toxicity class II or III, depending on the formulation. |
| FRCD ID | F05124 |
| CAS Number | 7287-19-6 |
| PubChem CID | 4929 |
| Formula | C10H19N5S |
| IUPAC Name | 6-methylsulfanyl-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| InChI Key | AAEVYOVXGOFMJO-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H19N5S/c1-6(2)11-8-13-9(12-7(3)4)15-10(14-8)16-5/h6-7H,1-5H3,(H2,11,12,13,14,15) |
| Canonical SMILES | CC(C)NC1=NC(=NC(=N1)SC)NC(C)C |
| Isomeric SMILES | CC(C)NC1=NC(=NC(=N1)SC)NC(C)C |
| Synonyms |
Prometryne
prometryn
7287-19-6
Gesagard
Prometrex
Selectin
Caparol
Uvon
Primatol Q
Mercasin
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | 1,3,5-triazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Methylthio-s-triazines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Methylthio-s-triazine - 2,4-diamine-s-triazine - Alkyl-2-thio-s-triazine - Aryl thioether - Amino-1,3,5-triazine - Aminotriazine - Secondary aliphatic/aromatic amine - Alkylarylthioether - N-aliphatic s-triazine - Heteroaromatic compound - Azacycle - Sulfenyl compound - Thioether - Secondary amine - Amine - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as methylthio-s-triazines. These are aromatic compounds containing a 1,3,5-triazine ring that is substituted at the 2-position with a methylthio group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 241.357 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Complexity | 182 |
| Monoisotopic Mass | 241.136 |
| Exact Mass | 241.136 |
| XLogP | 3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.7712 |
| Human Intestinal Absorption | HIA+ | 0.6888 |
| Caco-2 Permeability | Caco2+ | 0.5520 |
| P-glycoprotein Substrate | Non-substrate | 0.7710 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8580 |
| Non-inhibitor | 0.9218 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8528 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5851 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8359 |
| CYP450 2D6 Substrate | Non-substrate | 0.7368 |
| CYP450 3A4 Substrate | Non-substrate | 0.6819 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7863 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5466 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9217 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6915 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9263 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5163 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9783 |
| Non-inhibitor | 0.8501 | |
| AMES Toxicity | Non AMES toxic | 0.9070 |
| Carcinogens | Non-carcinogens | 0.9356 |
| Fish Toxicity | Low FHMT | 0.5866 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7074 |
| Honey Bee Toxicity | Low HBT | 0.5911 |
| Biodegradation | Not ready biodegradable | 0.9947 |
| Acute Oral Toxicity | III | 0.8560 |
| Carcinogenicity (Three-class) | Non-required | 0.3560 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0374 | LogS |
| Caco-2 Permeability | 1.6519 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0910 | LD50, mol/kg |
| Fish Toxicity | 2.1513 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4096 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Milk | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.05ppm | |||
| Pig,Edible Offal | Japan | 0.05ppm | |||
| Cattle,Edible Offal | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.05ppm | |||
| Pig,Kidney | Japan | 0.05ppm | |||
| Pig,Liver | Japan | 0.05ppm | |||
| Cattle,Liver | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 0.05ppm | |||
| Pig,Fat | Japan | 0.05ppm | |||
| Cattle,Fat | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.05ppm | |||
| Pig,Muscle | Japan | 0.05ppm | |||
| Cattle,Muscle | Japan | 0.05ppm | |||
| Other Herbs | Japan | 0.05ppm | |||
| Other Spices | Japan | 0.1ppm | |||
| Cotton Seeds | Japan | 0.2ppm | |||
| Sunflower Seeds | Japan | 0.1ppm | |||
| Other Fruits | Japan | 0.1ppm | |||
| Other Vegetables | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enhanced degradation of prometryn and other s-triazine herbicides in purecultures and wastewater by polyvinyl alcohol-sodium alginate immobilizedLeucobacter sp. JW-1. | Sci Total Environ | 2018 Feb 15 | 28963898 |
| Novel hydrolytic de-methylthiolation of the s-triazine herbicide prometryn byLeucobacter sp. JW-1. | Sci Total Environ | 2017 Feb 1 | 27866738 |
| Self-assembled magnetic nanoparticle supported zeolitic imidazolate framework-8: An efficient adsorbent for the enrichment of triazine herbicides from fruit,vegetables, and water. | J Sep Sci | 2017 Feb | 27987275 |
| Distribution of pesticide residues in soil and uncertainty of sampling. | J Environ Sci Health B | 2017 Aug 3 | 28489977 |
| Determination triazine pesticides in cereal samples based on single-hole hollowmolecularly imprinted microspheres. | J Chromatogr A | 2015 Jan 9 | 25537174 |
| Interaction of prometryn to human serum albumin: insights from spectroscopic and molecular docking studies. | Pestic Biochem Physiol | 2014 Jan | 24485317 |
| Mechanized and natural soil-to-air transfer of trifluralin and prometryn from acotton field in Las Cruces, New Mexico. | J Agric Food Chem | 2013 Oct 16 | 24040758 |
| Application of RP-HPLC-diode array detector after SPE to the determination ofpesticides in pepper samples. | J AOAC Int | 2012 Sep-Oct | 23175966 |
| Extraction of eight triazine and phenylurea herbicides in yogurt by ionic liquid foaming-based solvent floatation. | J Chromatogr A | 2012 Jan 27 | 22218326 |
| Selective extraction of triazine herbicides based on a combination of membraneassisted solvent extraction and molecularly imprinted solid phase extraction. | J Chromatogr A | 2011 Feb 4 | 21190688 |
| Brain toxicokinetics of prometryne in mice. | Arh Hig Rada Toksikol | 2010 Mar | 20338864 |
| Multiwalled carbon nanotubes as matrix solid-phase dispersion extractionabsorbents to determine 31 pesticides in agriculture samples by gaschromatography-mass spectrometry. | J Agric Food Chem | 2009 Apr 22 | 19326860 |
| Direct and indirect effects of pollutants on algae and algivorous ciliates in an aquatic indoor microcosm. | Aquat Toxicol | 2008 Jun 23 | 18462817 |
| Mobility of prometryne in soil as affected by dissolved organic matter. | J Agric Food Chem | 2008 Dec 24 | 19053378 |
| Direct aqueous injection LC-ESI/MS/MS analysis of water for 11 chloro- andthiomethyltriazines and metolachlor and its ethanesulfonic and oxanilic aciddegradates. | J Agric Food Chem | 2008 Apr 23 | 18373350 |
| Determination of triazine herbicides in fruits and vegetables using dispersivesolid-phase extraction coupled with LC-MS. | J Sep Sci | 2008 Apr | 18338404 |
| Multi-residue determination of pesticides in water using multi-walled carbonnanotubes solid-phase extraction and gas chromatography-mass spectrometry. | J Chromatogr A | 2007 Sep 21 | 17697685 |
| Assessment of olive cake as soil amendment for the controlled release of triazineherbicides. | Sci Total Environ | 2007 May 25 | 17289120 |
| Biodegradation of methylthio-s-triazines by Rhodococcus sp. strain FJ1117YT, and production of the corresponding methylsulfinyl, methylsulfonyl and hydroxyanalogues. | Pest Manag Sci | 2007 Mar | 17245693 |
| Evaluation of the pesticide contamination of groundwater sampled over two yearsfrom a vulnerable zone in Portugal. | J Agric Food Chem | 2007 Jul 25 | 17608425 |
Targets
- General Function:
- Metal ion binding
- Specific Function:
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name:
- PDE4A
- Uniprot ID:
- P27815
- Molecular Weight:
- 98142.155 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 ]
- 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:
- Interleukin-8 receptor binding
- Specific Function:
- IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively.
- Gene Name:
- CXCL8
- Uniprot ID:
- P10145
- Molecular Weight:
- 11097.98 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 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:
- Identical protein binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- ADORA2A
- Uniprot ID:
- P29274
- Molecular Weight:
- 44706.925 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:
- Metal ion binding
- Specific Function:
- Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
- Gene Name:
- PDE5A
- Uniprot ID:
- O76074
- Molecular Weight:
- 99984.14 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:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 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:
- 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:
- Tumor necrosis factor receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Upregulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:22517918).The TNF intracellular domain (ICD) form induces IL12 production in dendritic cells.
- Gene Name:
- TNF
- Uniprot ID:
- P01375
- Molecular Weight:
- 25644.15 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 ]