Pyrimethanil
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Basic Info
| Common Name | Pyrimethanil(F05437) |
| 2D Structure | |
| Description | Pyrimethanil is a fungicide used on grape vines. |
| FRCD ID | F05437 |
| CAS Number | 53112-28-0 |
| PubChem CID | 91650 |
| Formula | C12H13N3 |
| IUPAC Name | 4,6-dimethyl-N-phenylpyrimidin-2-amine |
| InChI Key | ZLIBICFPKPWGIZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15) |
| Canonical SMILES | CC1=CC(=NC(=N1)NC2=CC=CC=C2)C |
| Isomeric SMILES | CC1=CC(=NC(=N1)NC2=CC=CC=C2)C |
| Synonyms |
Pyrimethanil
53112-28-0
4,6-dimethyl-N-phenyl-2-pyrimidinamine
4,6-dimethyl-N-phenylpyrimidin-2-amine
Pyrimethanil [ISO]
2-Anilino-4,6-dimethylpyrimidine
2-Pyrimidinamine, 4,6-dimethyl-N-phenyl-
UNII-6IA5HP6C8Z
HSDB 6916
6IA5HP6C8Z
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Aniline and substituted anilines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aniline and substituted anilines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aniline or substituted anilines - Aminopyrimidine - Pyrimidine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Secondary amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 199.257 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 179 |
| Monoisotopic Mass | 199.111 |
| Exact Mass | 199.111 |
| XLogP | 2.9 |
| 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+ | 0.9336 |
| Human Intestinal Absorption | HIA+ | 0.9914 |
| Caco-2 Permeability | Caco2+ | 0.7529 |
| P-glycoprotein Substrate | Non-substrate | 0.7553 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9028 |
| Non-inhibitor | 0.9566 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7691 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7262 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8201 |
| CYP450 2D6 Substrate | Non-substrate | 0.7961 |
| CYP450 3A4 Substrate | Non-substrate | 0.7127 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6909 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9628 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8341 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6402 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8943 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5310 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9058 |
| Non-inhibitor | 0.8865 | |
| AMES Toxicity | Non AMES toxic | 0.7894 |
| Carcinogens | Non-carcinogens | 0.9234 |
| Fish Toxicity | Low FHMT | 0.6669 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9688 |
| Honey Bee Toxicity | Low HBT | 0.8174 |
| Biodegradation | Not ready biodegradable | 0.9769 |
| Acute Oral Toxicity | III | 0.8623 |
| Carcinogenicity (Three-class) | Non-required | 0.5288 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4995 | LogS |
| Caco-2 Permeability | 1.8275 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8887 | LD50, mol/kg |
| Fish Toxicity | 2.1216 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6046 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Beans | Britain | 0.1mg/kg | |||
| Lettuce | Italy | 2mg/kg | |||
| Peas | Britain | 0.1mg/kg | |||
| Beans (With Pods) | Britain | 0.1mg/kg | |||
| Other Pome Fruit | Britain | 5mg/kg | |||
| Quinces | Britain | 5mg/kg | |||
| Pears | Britain | 5mg/kg | |||
| Apples | Britain | 5mg/kg | |||
| Other Citrus Fruit | Britain | 5mg/kg | |||
| Pomelos | Britain | 5mg/kg | |||
| Oranges | Britain | 5mg/kg | |||
| Mandarins (Inc Clementines & Similar Hybrids) | Britain | 5mg/kg | |||
| Limes | Britain | 5mg/kg | |||
| Lemons | Britain | 5mg/kg | |||
| Grapefruit | Britain | 5mg/kg | |||
| Milk | Japan | 0.02ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.03ppm | |||
| Pig,Edible Offal | Japan | 0.05ppm | |||
| Cattle,Edible Offal | Japan | 0.03ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.04ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Transfer of the Active Ingredients of Some Plant Protection Products fromRaspberry Plants to Beehives. | Arch Environ Contam Toxicol | 2018 Jul | 29247388 |
| Comparison of the Impact of Two Molecules on Plant Defense and on Efficacyagainst Botrytis cinerea in the Vineyard: A Plant Defense Inducer(Benzothiadiazole) and a Fungicide (Pyrimethanil). | J Agric Food Chem | 2018 Apr 4 | 29557656 |
| Rapid and sensitive detection of pyrimethanil residues on pome fruits by Surface Enhanced Raman Scattering. | Food Chem | 2018 Apr 1 | 29120765 |
| Characterization of Postharvest Fungicide-Resistant Botrytis cinerea IsolatesFrom Commercially Stored Apple Fruit. | Phytopathology | 2017 Mar | 27841961 |
| Cultivating Chlorella vulgaris and Scenedesmus quadricauda microalgae to degrade inorganic compounds and pesticides in water. | Environ Sci Pollut Res Int | 2016 Sep | 27259964 |
| Conditions Optimizing and Application of Laccase-mediator System (LMS) for theLaccase-catalyzed Pesticide Degradation. | Sci Rep | 2016 Oct 24 | 27775052 |
| Degradation of imazalil, orthophenylphenol and pyrimethanil in Clementinemandarins under conventional postharvest industrial conditions at 4°C. | Food Chem | 2016 Mar 1 | 26471663 |
| Volatilisation of pesticides under field conditions: inverse modelling andpesticide fate models. | Pest Manag Sci | 2016 Jul | 26374459 |
| Fungicide multiresidue monitoring in international wines by immunoassays. | Food Chem | 2016 Apr 1 | 26593617 |
| Simultaneous Determination of Seven Kinds of Fungicides in Citrus Fruits by GasChromatograghy/Mass Spectrometry. | Shokuhin Eiseigaku Zasshi | 2016 | 27558228 |
| Synthesis of Novel Pyrimethanil Grafted Chitosan Derivatives with EnhancedAntifungal Activity. | Biomed Res Int | 2016 | 27529072 |
| Studies of pesticide residues in tomatoes and cucumbers from Kazakhstan and theassociated health risks. | Environ Monit Assess | 2015 Oct | 26337756 |
| An electrochemical fungicide pyrimethanil sensor based on carbonnanotubes/ionic-liquid construction modified electrode. | Food Chem | 2015 Nov 15 | 25976990 |
| Application of zirconium dioxide nanoparticle sorbent for the clean-up step inpost-harvest pesticide residue analysis. | Talanta | 2015 Nov 1 | 26452791 |
| Influence of adjuvants on the dissipation of fenpropimorph, pyrimethanil,chlorpyrifos and lindane on the solid/gas interface. | Chemosphere | 2015 Nov | 26133697 |
| Off-line coupling of multidimensional immunoaffinity chromatography and ionmobility spectrometry: A promising partnership. | J Chromatogr A | 2015 Dec 24 | 26654255 |
| A case study on toxicological aspects of the pest and disease control in theproduction of the high-quality raspberry (Rubus idaeus L.). | J Environ Sci Health B | 2015 | 25421623 |
| Effervescence-assisted dispersive liquid-liquid microextraction using a solideffervescent agent as a novel dispersion technique for the analysis of fungicidesin apple juice. | J Sep Sci | 2014 Nov | 25136817 |
| Potential mechanisms underlying response to effects of the fungicide pyrimethanilfrom gene expression profiling in Saccharomyces cerevisiae. | J Agric Food Chem | 2014 Jun 11 | 24835131 |
| Determination of 28 pesticides applied on two tomato cultivars with a differentsurface/weight ratio of the berries, using a multiresidue GC-MS/MS method. | J Environ Sci Health B | 2014 | 25035916 |
Targets
- 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:
- 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. 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 ]
- 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:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 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:
- 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:
- 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:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]