Chlorotoluron
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Basic Info
| Common Name | Chlorotoluron(F05862) |
| 2D Structure | |
| FRCD ID | F05862 |
| CAS Number | 15545-48-9 |
| PubChem CID | 27375 |
| Formula | C10H13ClN2O |
| IUPAC Name | 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea |
| InChI Key | JXCGFZXSOMJFOA-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H13ClN2O/c1-7-4-5-8(6-9(7)11)12-10(14)13(2)3/h4-6H,1-3H3,(H,12,14) |
| Canonical SMILES | CC1=C(C=C(C=C1)NC(=O)N(C)C)Cl |
| Isomeric SMILES | CC1=C(C=C(C=C1)NC(=O)N(C)C)Cl |
| Synonyms |
3-(3-Chloro-4-methylphenyl)-1,1-dimethylurea
Chlorotoluron
CHLORTOLURON
15545-48-9
Dicuran
Tolurex
Clortokem
Dikurin
Highuron
Chlortoluron [BSI]
|
| 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 - Chlorobenzene - Halobenzene - Toluene - Aryl chloride - Aryl halide - Carbonic acid derivative - Urea - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organooxygen compound - Organic nitrogen 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 | 212.677 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Complexity | 208 |
| Monoisotopic Mass | 212.072 |
| Exact Mass | 212.072 |
| XLogP | 2.4 |
| 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+ | 0.9689 |
| Human Intestinal Absorption | HIA+ | 0.9832 |
| Caco-2 Permeability | Caco2+ | 0.6775 |
| P-glycoprotein Substrate | Non-substrate | 0.7680 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9487 |
| Non-inhibitor | 0.9600 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8789 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6910 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6985 |
| CYP450 2D6 Substrate | Non-substrate | 0.7308 |
| CYP450 3A4 Substrate | Substrate | 0.5807 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7715 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7283 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8673 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6113 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8496 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8012 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8568 |
| Non-inhibitor | 0.7684 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.5194 |
| Fish Toxicity | High FHMT | 0.7483 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9554 |
| Honey Bee Toxicity | Low HBT | 0.8909 |
| Biodegradation | Not ready biodegradable | 0.9937 |
| Acute Oral Toxicity | III | 0.5660 |
| Carcinogenicity (Three-class) | Non-required | 0.4889 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5224 | LogS |
| Caco-2 Permeability | 1.8415 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0642 | LD50, mol/kg |
| Fish Toxicity | 1.1724 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9792 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Red mustards | 0251070 | European Union | 0.01* | 25/08/2014 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 25/08/2014 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 25/08/2014 | |
| 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* | 25/08/2014 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 25/08/2014 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 25/08/2014 | |
| 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* | 25/08/2014 | |
| Others (2) | 0110990 | European Union | 0.01* | 25/08/2014 | |
| Tree nuts | 0120000 | European Union | 0.02* | 25/08/2014 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 25/08/2014 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 25/08/2014 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 25/08/2014 | |
| Chestnuts | 0120040 | European Union | 0.02* | 25/08/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 25/08/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 25/08/2014 | |
| Macadamias | 0120070 | European Union | 0.02* | 25/08/2014 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 25/08/2014 | |
| 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* | 25/08/2014 | |
| Pistachios | 0120100 | European Union | 0.02* | 25/08/2014 | |
| Walnuts | 0120110 | European Union | 0.02* | 25/08/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Preparation of a magnetic porous organic polymer for the efficient extraction of phenylurea herbicides. | J Chromatogr A | 2017 Oct 13 | 28888678 |
| Fatty Acid Methyl Ester (FAME) Succession in Different Substrates as Affected by the Co-Application of Three Pesticides. | PLoS One | 2015 Dec 22 | 26694029 |
| Assessment of the leaching potential of 12 substituted phenylurea herbicides intwo agricultural soils under laboratory conditions. | J Agric Food Chem | 2012 May 30 | 22578198 |
| One step carbon nanotubes-based solid-phase extraction for the gaschromatographic-mass spectrometric multiclass pesticide control in virgin oliveoils. | J Chromatogr A | 2009 Oct 23 | 19298965 |
| The kinetics of sorption by retarded diffusion into soil aggregate pores. | Environ Sci Technol | 2009 Nov 1 | 19924948 |
| Lysimeter experiment to investigate the potential influence of diffusion-limited sorption on pesticide availability for leaching. | J Agric Food Chem | 2006 Nov 29 | 17117804 |
| Effect of dissolved organic matter on the toxicity of chlorotoluron to Triticumaestivum. | J Environ Sci (China) | 2006 | 20050556 |
| Pesticide sorption and diffusion in natural clay loam aggregates. | J Agric Food Chem | 2005 Nov 16 | 16277415 |
| Transgenic rice containing human CYP2B6 detoxifies various classes of herbicides. | J Agric Food Chem | 2005 May 4 | 15853388 |
| Lolium rigidum, a pool of resistance mechanisms to ACCase inhibitor herbicides. | J Agric Food Chem | 2005 Mar 23 | 15769155 |
| Clean up of phenylurea herbicides in plant sample extracts using molecularlyimprinted polymers. | Anal Bioanal Chem | 2005 Mar | 15756601 |
| Analysis of substrate specificity of pig CYP2B22 and CYP2C49 towards herbicidesby transgenic rice plants. | Transgenic Res | 2005 Dec | 16315095 |
| Water purification from organic pollutants by optimized micelle-clay systems. | Environ Sci Technol | 2005 Apr 1 | 15871274 |
| Sorption-desorption behavior of triazine and phenylurea herbicides in Kishonriver sediments. | Water Res | 2004 Dec | 15556213 |
| Effects of addition of straw, chitin and manure to new or recycled biofilters on their pesticides retention and degradation properties. | Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet | 2002 | 12701413 |
| Soil dissipation of diuron, chlorotoluron, simazine, propyzamide, anddiflufenican herbicides after repeated applications in fruit tree orchards. | Arch Environ Contam Toxicol | 2000 Jul | 10790503 |
| Expression of a soybean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. | Proc Natl Acad Sci U S A | 1999 Feb 16 | 9990096 |
| [The determination of diuron and chlortoluron residues in beef and beef products by high performance liquid chromatography]. | Se Pu | 1998 Jul | 11367770 |