Linuron
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Basic Info
| Common Name | Linuron(F05426) |
| 2D Structure | |
| Description | Linuron is an herbicide for the pre- and post-emergence control of annual grass and broad-leaved weeds using selective and systemic action with contact and residual action. It is known to inhibit photosynthesis (photosystem II). |
| FRCD ID | F05426 |
| CAS Number | 330-55-2 |
| PubChem CID | 9502 |
| Formula | C9H10Cl2N2O2 |
| IUPAC Name | 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea |
| InChI Key | XKJMBINCVNINCA-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) |
| Canonical SMILES | CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC |
| Isomeric SMILES | CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC |
| Synonyms |
3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea
LINURON
330-55-2
Methoxydiuron
Afalon
Cephalon
Aphalon
Linurex
Lorox
Afalon inuron
|
| Classifies |
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 - Carbonic acid derivative - Organic nitrogen compound - Organochloride - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen 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 | 249.091 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 228 |
| Monoisotopic Mass | 248.012 |
| Exact Mass | 248.012 |
| XLogP | 3.2 |
| 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+ | 0.9583 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6112 |
| P-glycoprotein Substrate | Non-substrate | 0.8450 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9041 |
| Non-inhibitor | 0.9177 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9392 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7946 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7098 |
| CYP450 2D6 Substrate | Non-substrate | 0.8276 |
| CYP450 3A4 Substrate | Substrate | 0.5306 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7242 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5646 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8541 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7155 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8829 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7561 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9445 |
| Non-inhibitor | 0.8916 | |
| AMES Toxicity | AMES toxic | 0.7833 |
| Carcinogens | Non-carcinogens | 0.6090 |
| Fish Toxicity | High FHMT | 0.8539 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9893 |
| Honey Bee Toxicity | Low HBT | 0.8734 |
| Biodegradation | Not ready biodegradable | 0.9909 |
| Acute Oral Toxicity | III | 0.7981 |
| Carcinogenicity (Three-class) | Non-required | 0.5067 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4577 | LogS |
| Caco-2 Permeability | 1.9573 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3054 | LD50, mol/kg |
| Fish Toxicity | 1.2273 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6661 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| (e) other fruiting vegetables | 0239000 | European Union | 0.05* | 01/09/2008 | |
| Brassica vegetables (excluding brassica roots and brassica baby leaf crops) | 0240000 | European Union | 0.05* | 01/09/2008 | |
| Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba... | 0243020 | European Union | 0.05* | 01/09/2008 | |
| Olives for oil production | 0402010 | European Union | 0.05* | 01/09/2008 | |
| Oil palms kernels (Argan nuts, Babassu palm nuts, Jojoba nuts, Shea nuts,) | 0402020 | European Union | 0.1* | 01/09/2008 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.1* | 01/09/2008 | |
| Chicory | Japan | 0.2ppm | |||
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 1 | 01/09/2008 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 01/09/2008 | |
| (c) cucurbits with inedible peel | 0233000 | European Union | 0.05* | 01/09/2008 | |
| Oilseeds | 0401000 | European Union | 0.1* | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 01/09/2008 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.05* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.05* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Ozone treatment for pesticide removal from carrots: Optimization by responsesurface methodology. | Food Chem | 2018 Mar 15 | 29146362 |
| Weed interference with peppermint (Mentha x piperita L.) and spearmint (Menthaspicata L.) crops under different herbicide treatments: effects on biomass andessential oil yield. | J Sci Food Agric | 2018 Jan | 28503740 |
| The inhibition of myometrial contractions by chlorinated herbicides (atrazine andlinuron), and their disruptive effect on the secretory functions of uterine andovarian cells in cow, in vitro. | Pestic Biochem Physiol | 2017 Oct | 29107246 |
| Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim. | Anal Chem | 2017 Mar 7 | 28264568 |
| Simultaneous removal of structurally different pesticides in a biomixture:Detoxification and effect of oxytetracycline. | Chemosphere | 2017 Feb | 27898329 |
| Adaptive response under multiple stress exposure in fish: From the molecular toindividual level. | Chemosphere | 2017 Dec | 28869847 |
| Evidence of in vitro metabolic interaction effects of a chlorfenvinphos, ethionand linuron mixture on human hepatic detoxification rates. | Chemosphere | 2017 Aug | 28476006 |
| Exploring the complex response to linuron of bacterial communities frombiopurification systems by means of cultivation-independent methods. | FEMS Microbiol Ecol | 2016 Feb | 26705572 |
| Functional Redundancy of Linuron Degradation in Microbial Communities inAgricultural Soil and Biopurification Systems. | Appl Environ Microbiol | 2016 Apr 18 | 26944844 |
| The herbicide linuron inhibits cholesterol biosynthesis and induces cellularstress responses in brown trout. | Environ Sci Technol | 2015 Mar 3 | 25633873 |
| Ionic liquid coated magnetic core/shell Fe3O4@SiO2 nanoparticles for theseparation/analysis of linuron in food samples. | Spectrochim Acta A Mol Biomol Spectrosc | 2015 Feb 25 | 25238184 |
| Comparative evaluation of the efficiency of low-cost adsorbents and ligninolytic fungi to remove a combination of xenoestrogens and pesticides from a landfillleachate and abate its phytotoxicity. | J Environ Sci Health A Tox Hazard Subst Environ Eng | 2015 | 26061209 |
| Effect of different organic amendments on the dissipation of linuron, diazinonand myclobutanil in an agricultural soil incubated for different time periods. | Sci Total Environ | 2014 Apr 1 | 24496034 |
| Environmental dissolved organic matter governs biofilm formation and subsequentlinuron degradation activity of a linuron-degrading bacterial consortium. | Appl Environ Microbiol | 2013 Aug | 23666338 |
| Application of RP-HPLC-diode array detector after SPE to the determination ofpesticides in pepper samples. | J AOAC Int | 2012 Sep-Oct | 23175966 |
| Multiresidue pesticide analysis of tuber and root commodities by QuEchERSextraction and ultra-performance liquid chromatography coupled to tandem massspectrometry. | J AOAC Int | 2012 Sep-Oct | 23175961 |
| Enhanced mineralization of diuron using a cyclodextrin-based bioremediation technology. | J Agric Food Chem | 2012 Oct 10 | 22985203 |
| Pesticide application and detection in variable agricultural intensity watershedsand their river systems in the maritime region of Canada. | Arch Environ Contam Toxicol | 2012 Nov | 22903630 |
| Assessment of the leaching potential of 12 substituted phenylurea herbicides intwo agricultural soils under laboratory conditions. | J Agric Food Chem | 2012 May 30 | 22578198 |
| Functional redundancy and food web functioning in linuron-exposed ecosystems. | Environ Pollut | 2011 Oct | 21640453 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Lambright C, Ostby J, Bobseine K, Wilson V, Hotchkiss AK, Mann PC, Gray LE Jr: Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats. Toxicol Sci. 2000 Aug;56(2):389-99. [10910998 ]
- 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:
- 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:
- 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:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 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:
- 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:
- 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 ]