Fluometuron
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Basic Info
| Common Name | Fluometuron(F05419) |
| 2D Structure | |
| Description | Fluometuron is a soil applied herbicide used to control annual grasses and broad-leaved weeds. In the United States it was approved for use on cotton and sugarcane crops in 1974, but since 1986 is only approved for use on cotton. Its mode of action is selective and inhibits photosynthesis. |
| FRCD ID | F05419 |
| CAS Number | 2164-17-2 |
| PubChem CID | 16562 |
| Formula | C10H11F3N2O |
| IUPAC Name | 1,1-dimethyl-3-[3-(trifluoromethyl)phenyl]urea |
| InChI Key | RZILCCPWPBTYDO-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H11F3N2O/c1-15(2)9(16)14-8-5-3-4-7(6-8)10(11,12)13/h3-6H,1-2H3,(H,14,16) |
| Canonical SMILES | CN(C)C(=O)NC1=CC=CC(=C1)C(F)(F)F |
| Isomeric SMILES | CN(C)C(=O)NC1=CC=CC(=C1)C(F)(F)F |
| Synonyms |
1,1-Dimethyl-3-[3-(trifluoromethyl)phenyl]urea
FLUOMETURON
2164-17-2
Higalcoton
Pakhtaran
Cotoran
Lanex
Cottonex
Ciba 2059
Cotoran multi 50WP
|
| 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 - Trifluoromethylbenzene - Carbonic acid derivative - Urea - Alkyl fluoride - Organic oxide - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Alkyl halide - 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 | 232.206 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 253 |
| Monoisotopic Mass | 232.082 |
| Exact Mass | 232.082 |
| XLogP | 2.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9820 |
| Human Intestinal Absorption | HIA+ | 0.9871 |
| Caco-2 Permeability | Caco2+ | 0.6156 |
| P-glycoprotein Substrate | Non-substrate | 0.7593 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9597 |
| Non-inhibitor | 0.9357 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8971 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6489 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7318 |
| CYP450 2D6 Substrate | Non-substrate | 0.7765 |
| CYP450 3A4 Substrate | Non-substrate | 0.5198 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5821 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6574 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9340 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6700 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8822 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5346 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9805 |
| Non-inhibitor | 0.7428 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.5245 |
| Fish Toxicity | Low FHMT | 0.5174 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9772 |
| Honey Bee Toxicity | Low HBT | 0.8602 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7915 |
| Carcinogenicity (Three-class) | Non-required | 0.6946 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3673 | LogS |
| Caco-2 Permeability | 1.5700 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2354 | LD50, mol/kg |
| Fish Toxicity | 1.2800 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5216 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Durians | 0163100 | European Union | 0.01* | 01/09/2008 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 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 | 0.01* | 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 | 0.01* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 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 | 0.01* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.01* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.01* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.01* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.01* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 01/09/2008 | |
| Pistachios | 0120100 | European Union | 0.01* | 01/09/2008 | |
| Walnuts | 0120110 | European Union | 0.01* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Pesticide residue concentration in soil following conventional and Low-Input CropManagement in a Mediterranean agro-ecosystem, in Central Greece. | Sci Total Environ | 2016 Jan 15 | 26406107 |
| Effect of olive-mill waste addition to soil on sorption, persistence, andmobility of herbicides used in Mediterranean olive groves. | Sci Total Environ | 2012 Jul 1 | 22591988 |
| Comparative sorption and leaching study of the herbicides fluometuron and4-chloro-2-methylphenoxyacetic acid (MCPA) in a soil amended with biochars andother sorbents. | J Agric Food Chem | 2011 Dec 14 | 22023336 |
| Organoclays as soil amendments to increase the efficacy and reduce theenvironmental impact of the herbicide fluometuron in agricultural soils. | J Agric Food Chem | 2010 Jul 14 | 20545302 |
| Microbial degradation of fluometuron is influenced by roundup weatherMAX. | J Agric Food Chem | 2008 Sep 24 | 18729373 |
| Soil microbial activity is affected by Roundup WeatherMax and pesticides applied to cotton (Gossypium hirsutum). | J Agric Food Chem | 2006 Sep 20 | 16968086 |
| Pesticide removal from cotton farm tailwater by a pilot-scale ponded wetland. | Chemosphere | 2006 Jun | 16330067 |
| Controlled release of the herbicide, fluometuron, from matrix granules based onfractionated organosolv lignins. | J Agric Food Chem | 2003 Jul 2 | 12822941 |
| Electrospray liquid chromatography quadrupole ion trap mass spectrometrydetermination of phenyl urea herbicides in water. | J Agric Food Chem | 2001 Jun | 11409961 |
| Multiresidue HPLC methods for phenyl urea herbicides in water. | J Agric Food Chem | 2000 Sep | 10995323 |
| 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 |
Targets
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- 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:
- 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 ]
- 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 ]