Diuron
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Basic Info
| Common Name | Diuron(F05411) |
| 2D Structure | |
| Description | Diuron, also known as DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea), is an herbicide in the urea chemical family that inhibits photosynthesis. It was introduced by Bayer in 1954 under the trade name of Diuron. DCMU is a very specific and sensitive inhibitor of photosynthesis, the process by which plants use light, water, and carbon di-oxide from the atmosphere to form plant sugars and cellulose. Diuron blocks electron transport at a critical point in this process. It blocks the plastoquinone binding site of photosystem II, disallowing the electron flow from where it is generated, in photosystem II, to plastoquinone. This interrupts the photosynthetic electron transport chain in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (ATP and reductant potential). |
| FRCD ID | F05411 |
| CAS Number | 330-54-1 |
| PubChem CID | 3120 |
| Formula | C9H10Cl2N2O |
| IUPAC Name | 3-(3,4-dichlorophenyl)-1,1-dimethylurea |
| InChI Key | XMTQQYYKAHVGBJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) |
| Canonical SMILES | CN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl |
| Isomeric SMILES | CN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl |
| Synonyms |
3-(3,4-Dichlorophenyl)-1,1-dimethylurea
diuron
330-54-1
DCMU
Duran
Dynex
Dichlorfenidim
Herbatox
Vonduron
Dailon
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | N-phenylureas |
| Intermediate Tree Nodes | Not available |
| Direct Parent | N-phenylureas |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | N-phenylurea - 1,2-dichlorobenzene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Urea - Carbonic acid derivative - Organochloride - Organohalogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 233.092 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Complexity | 211 |
| Monoisotopic Mass | 232.017 |
| Exact Mass | 232.017 |
| XLogP | 2.7 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9755 |
| Human Intestinal Absorption | HIA+ | 0.9846 |
| Caco-2 Permeability | Caco2+ | 0.6600 |
| P-glycoprotein Substrate | Non-substrate | 0.7632 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9563 |
| Non-inhibitor | 0.9724 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8631 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6618 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7124 |
| CYP450 2D6 Substrate | Non-substrate | 0.7577 |
| CYP450 3A4 Substrate | Substrate | 0.5402 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7859 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7162 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8380 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5459 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8308 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7868 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8661 |
| Non-inhibitor | 0.7997 | |
| AMES Toxicity | Non AMES toxic | 0.8074 |
| Carcinogens | Non-carcinogens | 0.5804 |
| Fish Toxicity | High FHMT | 0.7423 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9608 |
| Honey Bee Toxicity | Low HBT | 0.9119 |
| Biodegradation | Not ready biodegradable | 0.9902 |
| Acute Oral Toxicity | III | 0.8112 |
| Carcinogenicity (Three-class) | Non-required | 0.5084 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.7377 | LogS |
| Caco-2 Permeability | 1.7781 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3285 | LD50, mol/kg |
| Fish Toxicity | 1.2774 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8612 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Grape | India | 1mg/kg | |||
| Yam | Japan | 0.05ppm | |||
| Cashew nuts | 0120030 | European Union | 0.02* | 06/03/2014 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 06/03/2014 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 06/03/2014 | |
| 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* | 06/03/2014 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 06/03/2014 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 06/03/2014 | |
| 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* | 06/03/2014 | |
| Others (2) | 0110990 | European Union | 0.01* | 06/03/2014 | |
| Tree nuts | 0120000 | European Union | 0.02* | 06/03/2014 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 06/03/2014 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 06/03/2014 | |
| Chestnuts | 0120040 | European Union | 0.02* | 06/03/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 06/03/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 06/03/2014 | |
| Macadamias | 0120070 | European Union | 0.02* | 06/03/2014 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 06/03/2014 | |
| 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* | 06/03/2014 | |
| Pistachios | 0120100 | European Union | 0.02* | 06/03/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The influence of natural dissolved organic matter on herbicide toxicity to marine microalgae is species-dependent. | Aquat Toxicol | 2018 May | 29529466 |
| Pesticide load dynamics during stormwater flow events in Mediterranean coastalstreams: Alexander stream case study. | Sci Total Environ | 2018 Jun 1 | 29289002 |
| Fast pesticide detection inside microfluidic device with integrated optical pH, oxygen sensors and algal fluorescence. | Biosens Bioelectron | 2017 Feb 15 | 27523821 |
| An assessment of direct and indirect effects of two herbicides on aquatic communities. | Environ Toxicol Chem | 2017 Aug | 28106287 |
| Leaching of Diuron, Hexazinone, and Sulfometuron-methyl Applied Alone and inMixture in Soils with Contrasting Textures. | J Agric Food Chem | 2017 Apr 5 | 28326783 |
| Effect of Soil Water Content on the Distribution of Diuron into OrganomineralAggregates of Highly Weathered Tropical Soils. | J Agric Food Chem | 2016 May 25 | 26697719 |
| How benthic diatoms within natural communities respond to eight common herbicides with different modes of action. | Sci Total Environ | 2016 Jul 1 | 27037885 |
| Fructose as a novel photosensitizer: Characterization of reactive oxygen species and an application in degradation of diuron and chlorpyrifos. | Chemosphere | 2016 Feb | 26519800 |
| Evaluation of Diuron Tolerance and Biotransformation by Fungi from a Sugar CanePlantation Sandy-Loam Soil. | J Agric Food Chem | 2016 Dec 14 | 27960295 |
| Does a voltage-sensitive outer envelope transport mechanism contributes to thechloroplast iron uptake? | Planta | 2016 Dec | 27541495 |
| Pesticides in the Ebro River basin: Occurrence and risk assessment. | Environ Pollut | 2016 Apr | 26802514 |
| Evaluation of polar organic micropollutants as indicators for wastewater-related coastal water quality impairment. | Environ Pollut | 2016 Apr | 26774775 |
| Using non-targeted direct analysis in real time-mass spectrometry (DART-MS) todiscriminate seeds based on endogenous or exogenous chemicals. | Anal Bioanal Chem | 2015 Oct | 26307112 |
| Sorption interactions of organic compounds with soils affected by agriculturalolive mill wastewater. | Chemosphere | 2015 Nov | 26183941 |
| Pesticide monitoring in the basin of Llobregat River (Catalonia, Spain) andcomparison with historical data. | Sci Total Environ | 2015 Jan 15 | 25034205 |
| Emerging contaminants (pharmaceuticals, personal care products, a food additiveand pesticides) in waters of Sydney estuary, Australia. | Mar Pollut Bull | 2015 Aug 15 | 26130525 |
| Ammonium chloride salting out extraction/cleanup for trace-level quantitativeanalysis in food and biological matrices by flow injection tandem massspectrometry. | Anal Chim Acta | 2013 Mar 20 | 23473245 |
| Current and emerging environmentally-friendly systems for fouling control in the marine environment. | Biotechnol Adv | 2013 Dec | 24051087 |
| Physiological and biochemical responses of Synechococcus sp. PCC7942 to Irgarol 1051 and diuron. | Aquat Toxicol | 2012 Oct 15 | 22789406 |
| Enhanced mineralization of diuron using a cyclodextrin-based bioremediation technology. | J Agric Food Chem | 2012 Oct 10 | 22985203 |
Targets
- 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:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 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:
- 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:
- 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:
- 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:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Noguerol TN, Boronat S, Casado M, Raldua D, Barcelo D, Pina B: Evaluating the interactions of vertebrate receptors with persistent pollutants and antifouling pesticides using recombinant yeast assays. Anal Bioanal Chem. 2006 Jul;385(6):1012-9. Epub 2006 May 17. [16705413 ]
- 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 ]