Trifluralin
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Basic Info
| Common Name | Trifluralin(F05450) |
| 2D Structure | |
| Description | Trifluralin is a commonly used pre-emergence soil-incorporated herbicide. With about 14 million pounds used in the United States in 2001, it is one of the most widely used herbicides. Trifluralin is generally applied to the soil to provide control of a variety of annual grass and broadleaf weed species. It inhibits root development by interrupting mitosis, and thus can control weeds as they germinate. Its mode of action is selective and inhibits mitosis and cell division. |
| FRCD ID | F05450 |
| CAS Number | 1582-09-8 |
| PubChem CID | 5569 |
| Formula | C13H16F3N3O4 |
| IUPAC Name | 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline |
| InChI Key | ZSDSQXJSNMTJDA-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 |
| Canonical SMILES | CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-] |
| Isomeric SMILES | CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-] |
| Synonyms |
trifluralin
1582-09-8
Treflan
Agreflan
Elancolan
Crisalin
Triflurex
Trifurex
Tristar
Nitran
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Aniline and substituted anilines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dinitroanilines |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Dinitroaniline - Trifluoromethylbenzene - Nitrobenzene - Nitroaromatic compound - Tertiary aliphatic/aromatic amine - Dialkylarylamine - C-nitro compound - Tertiary amine - Organic nitro compound - Organic oxoazanium - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Alkyl fluoride - Hydrocarbon derivative - Organic oxide - Organonitrogen compound - Organofluoride - Organopnictogen compound - Organohalogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Alkyl halide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 335.283 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Complexity | 392 |
| Monoisotopic Mass | 335.109 |
| Exact Mass | 335.109 |
| XLogP | 5.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 28/10/2015 | |
| 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* | 28/10/2015 | |
| Carambolas (Ambarellas, Aonlas/Indian gooseberries, Babacos, Bilimbis, Cashew apples, Indian jujubes/bers, Jaboticabas, Malay pommarosas/pomeracs, Malayan mombins, Maprangs/marian plums, Natal plum... | 0161050 | European Union | 0.01* | 28/10/2015 | |
| Garlic | Japan | 0.05ppm | |||
| Others (2) | 0500990 | European Union | 0.01* | 28/10/2015 | |
| Others (2) | 0212990 | European Union | 0.01* | 28/10/2015 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 28/10/2015 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 28/10/2015 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 28/10/2015 | |
| 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* | 28/10/2015 | |
| Others (2) | 0110990 | European Union | 0.01* | 28/10/2015 | |
| Tree nuts | 0120000 | European Union | 0.01* | 28/10/2015 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 28/10/2015 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 28/10/2015 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 28/10/2015 | |
| Chestnuts | 0120040 | European Union | 0.01* | 28/10/2015 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 28/10/2015 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 28/10/2015 | |
| Macadamias | 0120070 | European Union | 0.01* | 28/10/2015 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 28/10/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum. | J Agric Food Chem | 2018 Jul 25 | 29965748 |
| Voltammetric detection of trifluralin in tap water, fruit juice, and vegetableextracts in the presence of surfactants. | J Environ Sci Health B | 2017 Oct 3 | 29022832 |
| Determination of the priority substances regulated by 2000/60/EC and 2008/105/EC Directives in the surface waters supplying water treatment plants of Athens, Greece. | J Environ Sci Health A Tox Hazard Subst Environ Eng | 2017 Mar 21 | 27973987 |
| 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 |
| Multi-residue analysis of pesticides in traditional Chinese medicines using gaschromatography-negative chemical ionisation tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 26125677 |
| Community air monitoring for pesticides-part 2: multiresidue determination ofpesticides in air by gas chromatography, gas chromatography-mass spectrometry,and liquid chromatography-mass spectrometry. | Environ Monit Assess | 2014 Mar | 24370860 |
| Evaluation of low-pressure gas chromatography-tandem mass spectrometry method forthe analysis of >140 pesticides in fish. | J Agric Food Chem | 2014 Apr 30 | 24387765 |
| Mechanized and natural soil-to-air transfer of trifluralin and prometryn from acotton field in Las Cruces, New Mexico. | J Agric Food Chem | 2013 Oct 16 | 24040758 |
| Investigation of the fate of trifluralin in shrimp. | J Agric Food Chem | 2013 Mar 13 | 23339341 |
| Pleiotropic effects of herbicide-resistance genes on crop yield: a review. | Pest Manag Sci | 2013 Aug | 23457026 |
| Pollution level and human health risk assessment of some pesticides and polychlorinated biphenyls in Nantong of Southeast China. | J Environ Sci (China) | 2012 | 23520856 |
| On-farm bioremediation of dimethazone and trifluralin residues in runoff water from an agricultural field. | J Environ Sci Health B | 2012 | 22560023 |
| [Application of the quechers method coupled with gas chromatography with electroncapture detection (GC-ECD) in analysis of pesticide residues in food]. | Rocz Panstw Zakl Hig | 2011 | 21980859 |
| Levels and seasonal variability of pesticides in the rural atmosphere of SouthernOntario. | J Agric Food Chem | 2010 Jan 27 | 20039708 |
| Abiotic reduction of pendimethalin and trifluralin in controlled and naturalsystems containing Fe(II) and dissolved organic matter. | J Agric Food Chem | 2010 Dec 22 | 21087048 |
| Control of Alopecurus myosuroides (black-grass) resistant tomesosulfuron+iodosulfuron. | Commun Agric Appl Biol Sci | 2009 | 20222608 |
| Mechanism of trifluralin-induced thyroid tumors in rats. | Toxicol Lett | 2008 Jul 30 | 18582544 |
| Evaporation drift of pesticides active ingredients. | Commun Agric Appl Biol Sci | 2008 | 19226822 |
| Assessment of the stability of pesticides during the cryogenic processing offruits and vegetables. | Food Addit Contam | 2007 Nov | 17852403 |
| Linkage of the California Pesticide Use Reporting Database with spatial land use data for exposure assessment. | Environ Health Perspect | 2007 May | 17520053 |
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:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 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 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:
- 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:
- Primary amine oxidase activity
- Specific Function:
- Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and signal transduction. The VCAM1/ITGA4/ITGB1 interaction may play a pathophysiologic role both in immune responses and in leukocyte emigration to sites of inflammation.
- Gene Name:
- VCAM1
- Uniprot ID:
- P19320
- Molecular Weight:
- 81275.43 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:
- 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:
- 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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 ]