Folpet
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Basic Info
| Common Name | Folpet(F05080) |
| 2D Structure | |
| Description | Folpet is a protective leaf-fungicide. Its mode of action inhibits normal cell division of a broad spectrum of microorganisms. It is used to control cherry leaf spot, rose mildew, rose black spot, and apple scab. Used on berries, flowers, ornamentals, fruits and vegetables, and for seed- and plant-bed treatment. Also used as a fungicide in paints and plastics, and for treatment of internal and external structural surfaces of buildings. Folpet has low acute toxicity to mammals. It is slighly toxic to birds and bees, and is moderately toxic to fish, aquatic invertebrates, algae and earthworms. Folpet is very irritating to the eyes and repeated or prolonged contact leads to skin sensitization. Chronic exposure tests showed folpet to be carcinogenic in mice (but not rats). On this basis, folpet is considered possibly carcinogenic to humans. |
| FRCD ID | F05080 |
| CAS Number | 133-07-3 |
| PubChem CID | 8607 |
| Formula | C9H4Cl3NO2S |
| IUPAC Name | 2-(trichloromethylsulfanyl)isoindole-1,3-dione |
| InChI Key | HKIOYBQGHSTUDB-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H |
| Canonical SMILES | C1=CC=C2C(=C1)C(=O)N(C2=O)SC(Cl)(Cl)Cl |
| Isomeric SMILES | C1=CC=C2C(=C1)C(=O)N(C2=O)SC(Cl)(Cl)Cl |
| Synonyms |
Folpel
Folpet
133-07-3
Orthophaltan
Phthaltan
Faltan
Acryptan
Spolacid
Folnit
Folpan
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Isoindoles and derivatives |
| Subclass | Isoindolines |
| Intermediate Tree Nodes | Isoindolones |
| Direct Parent | Phthalimides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Phthalimide - Isoindole - Benzenoid - Trihalomethane - Carboxylic acid derivative - Sulfenyl compound - Azacycle - Hydrocarbon derivative - Organic oxygen compound - Alkyl halide - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Alkyl chloride - Halomethane - Organopnictogen compound - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 296.546 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 307 |
| Monoisotopic Mass | 294.903 |
| Exact Mass | 294.903 |
| XLogP | 2.8 |
| 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+ | 0.9940 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5238 |
| P-glycoprotein Substrate | Non-substrate | 0.8856 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9240 |
| Non-inhibitor | 0.9517 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8397 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5286 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7132 |
| CYP450 2D6 Substrate | Non-substrate | 0.8149 |
| CYP450 3A4 Substrate | Non-substrate | 0.5228 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5098 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6316 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8555 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6092 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5656 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7323 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9851 |
| Non-inhibitor | 0.9368 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.8932 |
| Fish Toxicity | High FHMT | 0.9769 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9773 |
| Honey Bee Toxicity | Low HBT | 0.5407 |
| Biodegradation | Not ready biodegradable | 0.9314 |
| Acute Oral Toxicity | III | 0.8095 |
| Carcinogenicity (Three-class) | Non-required | 0.7004 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.9044 | LogS |
| Caco-2 Permeability | 1.5659 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0198 | LD50, mol/kg |
| Fish Toxicity | 1.4772 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7665 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Currants (Red, Black & White) | New Zealand | 15mg/kg | |||
| Kale | Britain | 0.02mg/kg | |||
| Blueberry | Japan | 20ppm | |||
| Blackberry | Japan | 20ppm | |||
| Raspberry | Japan | 20ppm | |||
| Cherry | Japan | 30ppm | |||
| Currants | CAC | 40 mg/kg | |||
| Hop | Britain | 150mg/kg | |||
| Tea | Britain | 0.05mg/kg | |||
| Ware Potatoes | Britain | 0.1mg/kg | |||
| Early Potatoes | Britain | 0.1mg/kg | |||
| Other Oilseeds | Britain | 0.05mg/kg | |||
| Hemp Seed | Britain | 0.05mg/kg | |||
| Cotton Seed | Britain | 0.05mg/kg | |||
| Mustard Seed | Britain | 0.05mg/kg | |||
| Soya Bean | Britain | 0.05mg/kg | |||
| Rape Seed | Britain | 0.05mg/kg | |||
| Sunflower Seed | Britain | 0.05mg/kg | |||
| Sesame Seed | Britain | 0.05mg/kg | |||
| Poppy Seed | Britain | 0.05mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Analysis of thermally labile pesticides by on-column injection gas chromatographyin fruit and vegetables. | Anal Bioanal Chem | 2018 Aug 13 | 30105623 |
| Pesticide residues in propolis from Spain and Chile. An approach using nearinfrared spectroscopy. | Talanta | 2017 Apr 1 | 28153295 |
| Development and validation of a method for the determination of 159 pesticideresidues in tobacco by gas chromatography-tandem mass spectrometry. | J Agric Food Chem | 2013 Jun 19 | 23701289 |
| Pesticide residues in berries harvested from South-Eastern Poland (2009-2011). | Rocz Panstw Zakl Hig | 2013 | 23789309 |
| Effects of temperature and purity of magnesium sulfate during extraction ofpesticide residues using the QuEChERS method. | J AOAC Int | 2012 Sep-Oct | 23175960 |
| Analysis of six fungicides and one acaricide in still and fortified wines usingsolid-phase microextraction-gas chromatography/tandem mass spectrometry. | Food Chem | 2012 May 1 | 26434342 |
| A multi-residue method for pesticides analysis in green coffee beans using gaschromatography-negative chemical ionization mass spectrometry in selective ionmonitoring mode. | J Chromatogr A | 2012 Aug 17 | 22771261 |
| Multipesticide residue analysis in maize combining acetonitrile-based extraction with dispersive liquid-liquid microextraction followed by gas chromatography-massspectrometry. | J Chromatogr A | 2011 Oct 28 | 21945620 |
| Qualitative aspects in the analysis of pesticide residues in fruits andvegetables using fast, low-pressure gas chromatography-time-of-flight massspectrometry. | J Agric Food Chem | 2011 Jul 27 | 21452898 |
| The effects of fungicides on non-target mites can be mediated by plant pathogens. | Chemosphere | 2010 Mar | 20172588 |
| Multiresidue analysis of 50 pesticides in grape, pomegranate, and mango by gaschromatography-ion trap mass spectrometry. | J Agric Food Chem | 2010 Feb 10 | 20020699 |
| Suitability of two laboratory testing methods to evaluate the side effects of pesticides on Typhlodromus pyri Scheuten (Acari: Phytoseiidae). | Pest Manag Sci | 2008 Feb | 18069656 |
| Multiresidue pesticide analysis of the medicinal plant Origanum syriacum. | Food Addit Contam | 2007 Mar | 17364929 |
| Large volume cold on-column injection for gas chromatography-negative chemicalionization-mass spectrometry analysis of selected pesticides in air samples. | J Agric Food Chem | 2007 Feb 21 | 17256963 |
| Quality and safety assessment of ginseng extracts by determination of the contents of pesticides and metals. | Food Addit Contam | 2005 Dec | 16356886 |
| Multiresidue method for the determination of pesticides in Korean domestic crops by gas chromatography/mass selective detection. | J AOAC Int | 2003 Jul-Aug | 14509443 |
| Rapid determination of fungicides in fruit juices by micellar electrokineticchromatography: use of organic modifiers to enhance selectivity and on-columnhigh-salt stacking to improve sensitivity. | Electrophoresis | 2000 Nov | 11271480 |
| Distribution of folpet on the grape surface after treatment. | J Agric Food Chem | 2000 Mar | 10725173 |
| Making best use of available residue data for acute intake assessment. | Food Addit Contam | 2000 Jul | 10983579 |
| Solid phase microextraction of pesticide residues from strawberries. | Food Addit Contam | 1999 Mar | 10492703 |
Targets
- 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:
- 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:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 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:
- Voltage-gated calcium channel activity
- Specific Function:
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociation of the G-protein complex with the free GTP-bound G-protein alpha and the G-protein beta-gamma dimer activating downstream cellular effectors. The agonist- and cell type-specific activity is predominantly coupled to pertussis toxin-sensitive G(i) and G(o) G alpha proteins, GNAI1, GNAI2, GNAI3 and GNAO1 isoforms Alpha-1 and Alpha-2, and to a lesser extend to pertussis toxin-insensitive G alpha proteins GNAZ and GNA15. They mediate an array of downstream cellular responses, including inhibition of adenylate cyclase activity and both N-type and L-type calcium channels, activation of inward rectifying potassium channels, mitogen-activated protein kinase (MAPK), phospholipase C (PLC), phosphoinositide/protein kinase (PKC), phosphoinositide 3-kinase (PI3K) and regulation of NF-kappa-B. Also couples to adenylate cyclase stimulatory G alpha proteins. The selective temporal coupling to G-proteins and subsequent signaling can be regulated by RGSZ proteins, such as RGS9, RGS17 and RGS4. Phosphorylation by members of the GPRK subfamily of Ser/Thr protein kinases and association with beta-arrestins is involved in short-term receptor desensitization. Beta-arrestins associate with the GPRK-phosphorylated receptor and uncouple it from the G-protein thus terminating signal transduction. The phosphorylated receptor is internalized through endocytosis via clathrin-coated pits which involves beta-arrestins. The activation of the ERK pathway occurs either in a G-protein-dependent or a beta-arrestin-dependent manner and is regulated by agonist-specific receptor phosphorylation. Acts as a class A G-protein coupled receptor (GPCR) which dissociates from beta-arrestin at or near the plasma membrane and undergoes rapid recycling. Receptor down-regulation pathways are varying with the agonist and occur dependent or independent of G-protein coupling. Endogenous ligands induce rapid desensitization, endocytosis and recycling whereas morphine induces only low desensitization and endocytosis. Heterooligomerization with other GPCRs can modulate agonist binding, signaling and trafficking properties. Involved in neurogenesis. Isoform 12 couples to GNAS and is proposed to be involved in excitatory effects. Isoform 16 and isoform 17 do not bind agonists but may act through oligomerization with binding-competent OPRM1 isoforms and reduce their ligand binding activity.
- Gene Name:
- OPRM1
- Uniprot ID:
- P35372
- Molecular Weight:
- 44778.855 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:
- 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
- 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:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Nociceptin receptor activity
- Specific Function:
- G-protein coupled opioid receptor that functions as receptor for the endogenous neuropeptide nociceptin. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling via G proteins mediates inhibition of adenylate cyclase activity and calcium channel activity. Arrestins modulate signaling via G proteins and mediate the activation of alternative signaling pathways that lead to the activation of MAP kinases. Plays a role in modulating nociception and the perception of pain. Plays a role in the regulation of locomotor activity by the neuropeptide nociceptin.
- Gene Name:
- OPRL1
- Uniprot ID:
- P41146
- Molecular Weight:
- 40692.775 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 ]