Quintozene
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Basic Info
| Common Name | Quintozene(F05439) |
| 2D Structure | |
| Description | Quintozene, also known as pentachloronitrobenzene, is a registered fungicide formally derived from nitrobenzene used as soil fungicide on lawns and ornamental crops, as a seed treatment of field crops and vegetables (e.g., barley, corn, cotton, oats, rice, and wheat), and as a slime inhibitor in industrial waters. It is also used to prevent the formation of slime in industrial waters. It is either an off-white or yellow solid, depending on its purity, with a musty odor. Residual amounts of the compound and its metabolites can be found in crops. The degradation products, PCA and PCTA have been found in farming soils and in river sediments. Its mode of action is through contact and interferes with mitotic division. |
| FRCD ID | F05439 |
| CAS Number | 82-68-8 |
| PubChem CID | 6720 |
| Formula | C6Cl5NO2 |
| IUPAC Name | 1,2,3,4,5-pentachloro-6-nitrobenzene |
| InChI Key | LKPLKUMXSAEKID-UHFFFAOYSA-N |
| InChI | InChI=1S/C6Cl5NO2/c7-1-2(8)4(10)6(12(13)14)5(11)3(1)9 |
| Canonical SMILES | C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)[N+](=O)[O-] |
| Isomeric SMILES | C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)[N+](=O)[O-] |
| Synonyms |
PENTACHLORONITROBENZENE
Quintozene
82-68-8
PCNB
Brassicol
Terrachlor
Batrilex
Botrilex
Earthcide
Fungiclor
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Nitrobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Nitrobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Nitrobenzene - Nitroaromatic compound - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - C-nitro compound - Organic nitro compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Organic nitrogen compound - Organochloride - Organohalogen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 295.321 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 219 |
| Monoisotopic Mass | 292.837 |
| Exact Mass | 294.834 |
| XLogP | 4.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Apples | Britain | 0.02mg/kg | |||
| Ginger | Japan | 0.02ppm | |||
| Okra | Japan | 0.02ppm | |||
| Table Grapes | Britain | 0.02mg/kg | |||
| Other Stone Fruit | Britain | 0.02mg/kg | |||
| Plums | Britain | 0.02mg/kg | |||
| Peaches (Incl Nectarines & Similar Hybrids | Britain | 0.02mg/kg | |||
| Cherries | Britain | 0.02mg/kg | |||
| Apricots | Britain | 0.02mg/kg | |||
| Other Pome Fruit | Britain | 0.02mg/kg | |||
| Quinces | Britain | 0.02mg/kg | |||
| Pears | Britain | 0.02mg/kg | |||
| Other Tree Nuts (Shelled Or Unshelled) | Britain | 0.02mg/kg | |||
| Walnuts | Britain | 0.02mg/kg | |||
| Pistachios | Britain | 0.02mg/kg | |||
| Pine Nuts | Britain | 0.02mg/kg | |||
| Pecans | Britain | 0.02mg/kg | |||
| Macadamia Nuts | Britain | 0.02mg/kg | |||
| Hazelnuts | Britain | 0.02mg/kg | |||
| Coconuts | Britain | 0.02mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Background biomonitoring of residue levels of 137 pesticides in the blood plasma of the general population in Beijing. | Environ Monit Assess | 2018 Apr 29 | 29705822 |
| Pesticide residues in nut-planted soils of China and their relationship betweennut/soil. | Chemosphere | 2017 Aug | 28391151 |
| Current-use pesticides in seawater and their bioaccumulation in polar bear-ringedseal food chains of the Canadian Arctic. | Environ Toxicol Chem | 2016 Jul | 27027986 |
| Pesticides in persimmons, jujubes and soil from China: Residue levels, riskassessment and relationship between fruits and soils. | Sci Total Environ | 2016 Jan 15 | 26544891 |
| Residue levels and risk assessment of pesticides in nuts of China. | Chemosphere | 2016 Feb | 26408971 |
| Trophodynamics of current use pesticides and ecological relationships in theBathurst region vegetation-caribou-wolf food chain of the Canadian Arctic. | Environ Toxicol Chem | 2014 Sep | 24975230 |
| Community air monitoring for pesticides-part 2: multiresidue determination ofpesticides in air by gas chromatography, gas chromatography-mass spectrometry,and liquid chromatography-mass spectrometry. | Environ Monit Assess | 2014 Mar | 24370860 |
| Analytical approaches for the determination of pesticide residues innutraceutical products and related matrices by chromatographic techniques coupledto mass spectrometry. | Talanta | 2014 Jan | 24274299 |
| Organochlorine pesticide residues in bamboo shoot. | J Sci Food Agric | 2011 Feb | 21218497 |
| Multiresidue pesticide analysis of ginseng powders using acetonitrile- oracetone-based extraction, solid-phase extraction cleanup, and gaschromatography-mass spectrometry/selective ion monitoring (GC-MS/SIM) or -tandem mass spectrometry (GC-MS/MS). | J Agric Food Chem | 2010 May 26 | 20225896 |
| Application of gamma irradiation in ginseng for both photodegradation ofpesticide pentachloronitrobenzene and microbial decontamination. | J Hazard Mater | 2010 Apr 15 | 19959285 |
| Organohalogen and organophosphorous pesticide method for ginseng root--acomparison of gas chromatography-single quadrupole mass spectrometry with highresolution time-of-flight mass spectrometry. | Anal Chem | 2009 Jul 15 | 19548696 |
| Effect of land use change from paddy to vegetable field on the residues oforganochlorine pesticides in soils. | Environ Pollut | 2008 Dec | 18554761 |
| Multiresidue pesticide analysis of the medicinal plant Origanum syriacum. | Food Addit Contam | 2007 Mar | 17364929 |
| Reliable enzyme immunoassay detection for chlorothalonil: fundamental evaluation for residue analysis and validation with gas chromatography. | J Chromatogr A | 2006 Oct 6 | 16870194 |
| Mycotoxin producing Fusarium species associated with plant disease on potato, wheat, corn and animal diseases in northwest Iran. | Commun Agric Appl Biol Sci | 2006 | 17390876 |
| Quality and safety assessment of ginseng extracts by determination of the contents of pesticides and metals. | Food Addit Contam | 2005 Dec | 16356886 |
| Genetic and functional characterization of a Bacillus sp. strain excretingsurfactin and antifungal metabolites partially identified as iturin-likecompounds. | J Appl Microbiol | 2004 | 15546416 |
| Determination of pesticide residues in nonfatty foods by supercritical fluidextraction and gas chromatography/mass spectrometry: collaborative study. | J AOAC Int | 2002 Sep-Oct | 12374416 |
| Analysis of pesticide residues in mixed fruit and vegetable extracts by directsample introduction/gas chromatography/tandem mass spectrometry. | J AOAC Int | 2000 May-Jun | 10868593 |
Targets
- General Function:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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 ]
- 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:
- 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:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 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:
- 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:
- 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:
- 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:
- 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 ]