Isoproturon
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Basic Info
| Common Name | Isoproturon(F05649) |
| 2D Structure | |
| FRCD ID | F05649 |
| CAS Number | 34123-59-6 |
| PubChem CID | 36679 |
| Formula | C12H18N2O |
| IUPAC Name | 1,1-dimethyl-3-(4-propan-2-ylphenyl)urea |
| InChI Key | PUIYMUZLKQOUOZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H18N2O/c1-9(2)10-5-7-11(8-6-10)13-12(15)14(3)4/h5-9H,1-4H3,(H,13,15) |
| Canonical SMILES | CC(C)C1=CC=C(C=C1)NC(=O)N(C)C |
| Isomeric SMILES | CC(C)C1=CC=C(C=C1)NC(=O)N(C)C |
| Synonyms |
3-(4-Isopropylphenyl)-1,1-dimethylurea
ISOPROTURON
34123-59-6
Graminon
Tolkan
Arelon
Belgran
Arelon R
Nocilon
IPU Stefes
|
| 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 - Phenylpropane - Cumene - Urea - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - 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 | 206.289 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 206 |
| Monoisotopic Mass | 206.142 |
| Exact Mass | 206.142 |
| XLogP | 2.9 |
| 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+ | 0.9667 |
| Human Intestinal Absorption | HIA+ | 0.9822 |
| Caco-2 Permeability | Caco2+ | 0.6780 |
| P-glycoprotein Substrate | Non-substrate | 0.7650 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9715 |
| Non-inhibitor | 0.9548 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8983 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6026 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7050 |
| CYP450 2D6 Substrate | Non-substrate | 0.6982 |
| CYP450 3A4 Substrate | Non-substrate | 0.5402 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5160 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7930 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9472 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8045 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9479 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6074 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8907 |
| Non-inhibitor | 0.9110 | |
| AMES Toxicity | Non AMES toxic | 0.8890 |
| Carcinogens | Non-carcinogens | 0.5366 |
| Fish Toxicity | Low FHMT | 0.6222 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8878 |
| Honey Bee Toxicity | Low HBT | 0.8026 |
| Biodegradation | Not ready biodegradable | 0.9353 |
| Acute Oral Toxicity | III | 0.8659 |
| Carcinogenicity (Three-class) | Non-required | 0.5183 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.1827 | LogS |
| Caco-2 Permeability | 1.8572 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0216 | LD50, mol/kg |
| Fish Toxicity | 1.6235 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5061 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Lentils | Britain | 0.05mg/kg | |||
| Other Miscellaneous Fruit | Britain | 0.05mg/kg | |||
| Other Cane Fruit (Other Than Wild) | Britain | 0.05mg/kg | |||
| Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves... | 0256030 | European Union | 0.02* | 25/08/2014 | |
| 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 | 0.02* | 25/08/2014 | |
| SUGAR PLANTS | 0900000 | European Union | 0.01* | 25/08/2014 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | 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 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 25/08/2014 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 25/08/2014 | |
| Chestnuts | 0120040 | European Union | 0.01* | 25/08/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 25/08/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 25/08/2014 | |
| Macadamias | 0120070 | European Union | 0.01* | 25/08/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Lab to Field Assessment of the Ecotoxicological Impact of Chlorpyrifos,Isoproturon, or Tebuconazole on the Diversity and Composition of the SoilBacterial Community. | Front Microbiol | 2018 Jun 29 | 30008705 |
| Use of a hypercrosslinked triphenylamine polymer as an efficient adsorbent forthe enrichment of phenylurea herbicides. | J Chromatogr A | 2018 Feb 23 | 29397984 |
| Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim. | Anal Chem | 2017 Mar 7 | 28264568 |
| Adaptive response under multiple stress exposure in fish: From the molecular toindividual level. | Chemosphere | 2017 Dec | 28869847 |
| Conditions Optimizing and Application of Laccase-mediator System (LMS) for theLaccase-catalyzed Pesticide Degradation. | Sci Rep | 2016 Oct 24 | 27775052 |
| Use of two artificial sweeteners, cyclamate and acesulfame, to identify andquantify wastewater contributions in a karst spring. | Sci Total Environ | 2016 Mar 15 | 26795541 |
| Assessment of two extraction methods to determine pesticides in soils, sediments and sludges. Application to the Túria River Basin. | J Chromatogr A | 2015 Jan 23 | 25573188 |
| Comprehensive two-dimensional liquid chromatography coupled to high resolutiontime of flight mass spectrometry for chemical characterization of sewagetreatment plant effluents. | J Chromatogr A | 2015 Feb 6 | 25578044 |
| Identification of photosynthesis inhibitors of pelagic marine algae using 96-wellplate microfractionation for enhanced throughput in effect-directed analysis. | Environ Sci Technol | 2014 Jul 15 | 24926900 |
| Pesticide pressure and fish farming in barrage pond in Northeastern France. Part II: residues of 13 pesticides in water, sediments, edible fish and theirrelationships. | Environ Sci Pollut Res Int | 2013 Jan | 22961490 |
| Accumulation and half-lives of 13 pesticides in muscle tissue of freshwaterfishes through food exposure. | Chemosphere | 2013 Apr | 23374295 |
| Toxicology of isoproturon to the food crop wheat as affected by salicylic acid. | Environ Sci Pollut Res Int | 2012 Jul | 22231370 |
| Extraction of eight triazine and phenylurea herbicides in yogurt by ionic liquid foaming-based solvent floatation. | J Chromatogr A | 2012 Jan 27 | 22218326 |
| Determination of phenylureas herbicides in food stuffs based on matrixsolid-phase dispersion extraction and capillary electrophoresis withelectrochemiluminescence detection. | J Chromatogr A | 2011 Dec 16 | 22078235 |
| Before the curtain falls: endocrine-active pesticides--a German contaminationlegacy. | Rev Environ Contam Toxicol | 2011 | 21541850 |
| Determination of phenylurea and triazine herbicides in milk by microwave assistedionic liquid microextraction high-performance liquid chromatography. | Talanta | 2010 Sep 15 | 20801343 |
| Screening of agrochemicals in foodstuffs using low-temperature plasma (LTP)ambient ionization mass spectrometry. | Analyst | 2010 May | 20419245 |
| Rate of loss of simazine, terbuthylazine, isoproturon, and methabenzthiazuronduring soil solarization. | J Agric Food Chem | 2009 Jul 22 | 19537795 |
| Control of Alopecurus myosuroides (black-grass) resistant tomesosulfuron+iodosulfuron. | Commun Agric Appl Biol Sci | 2009 | 20222608 |
| Influence of long-term used herbicides on resistance development in Aperaspica-venti L. to sulfonylureas. | Commun Agric Appl Biol Sci | 2009 | 20222609 |