Acifluorfen
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Basic Info
| Common Name | Acifluorfen(F05025) |
| 2D Structure | |
| Description | Acifluorfen is an herbicide. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice. Also registered as a spot treatment for residential use along driveways, sidewalks, and patios. acifluorfen has low acute toxicity via the oral, dermal, and inhalation routes of exposure, but causes severe eye irritation and moderate skin irritation. acifluorfen is currently classified as a B2 chemical carcinogen (probable human carcinogen). |
| FRCD ID | F05025 |
| CAS Number | 50594-66-6 |
| PubChem CID | 44073 |
| Formula | C14H7ClF3NO5 |
| IUPAC Name | None |
| InChI Key | NUFNQYOELLVIPL-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21) |
| Canonical SMILES | C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)O |
| Isomeric SMILES | C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)O |
| Synonyms |
5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid
Acifluorfen
50594-66-6
Acifluorfene
Tackle
Acifluorofen
Blazer
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
Acifluorfen [BSI:ISO]
Scifluorfen
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Diphenylethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diphenylethers |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Diphenylether - Nitrobenzoate - Diaryl ether - Trifluoromethylbenzene - Nitrobenzene - Benzoic acid or derivatives - Benzoic acid - Phenoxy compound - Phenol ether - Nitroaromatic compound - Benzoyl - Halobenzene - Chlorobenzene - Aryl chloride - Aryl halide - C-nitro compound - Organic nitro compound - Carboxylic acid derivative - Carboxylic acid - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Ether - Allyl-type 1,3-dipolar organic compound - Monocarboxylic acid or derivatives - Organic oxoazanium - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Alkyl fluoride - Organopnictogen compound - Organic oxide - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organochloride - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 361.657 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 3 |
| Complexity | 484 |
| Monoisotopic Mass | 360.996 |
| Exact Mass | 360.996 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| 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 |
|---|---|---|---|---|---|
| Other Poultry,Eggs | Japan | 0.02ppm | |||
| Chicken,Eggs | Japan | 0.02ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.06ppm | |||
| Chicken,Edible Offal | Japan | 0.06ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.06ppm | |||
| Chicken,Kidney | Japan | 0.06ppm | |||
| Other Poultry Animals,Liver | Japan | 0.06ppm | |||
| Chicken,Liver | Japan | 0.06ppm | |||
| Other Poultry Animals,Fat | Japan | 0.02ppm | |||
| Chicken,Fat | Japan | 0.02ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.02ppm | |||
| Chicken,Muscle | Japan | 0.02ppm | |||
| Milk | Japan | 0.02ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
| Pig,Edible Offal | Japan | 0.1ppm | |||
| Cattle,Edible Offal | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.06ppm | |||
| Pig,Kidney | Japan | 0.06ppm | |||
| Cattle,Kidney | Japan | 0.06ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.06ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enantioselective degradation in sediment and aquatic toxicity to Daphnia magna ofthe herbicide lactofen enantiomers. | J Agric Food Chem | 2010 Feb 24 | 20088506 |
| Ecotoxicological effects of combined UVB and organic contaminants in coastal waters: A review. | Photochem Photobiol | 2006 Jul-Aug | 16602830 |
| Soil photolysis of herbicides in a moisture- and temperature-controlledenvironment. | J Agric Food Chem | 2003 Jul 16 | 12848506 |
| Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds ofglyphosate-treated, glyphosate-resistant soybean. | J Agric Food Chem | 2003 Jan 1 | 12502430 |
| Off-line solid-phase microextraction and capillary electrophoresis massspectrometry to determine acidic pesticides in fruits. | Anal Chem | 2003 Feb 1 | 12585470 |
| Synthesis of haptens and protein conjugates for the development of immunoassaysfor the insect growth regulator fenoxycarb. | J Agric Food Chem | 2002 Jan 2 | 11754538 |
| Photochemical degradation of acifluorfen in aqueous solution. | J Agric Food Chem | 2001 Oct | 11600024 |
Targets
- General Function:
- Oxygen-dependent protoporphyrinogen oxidase activity
- Specific Function:
- Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
- Gene Name:
- PPOX
- Uniprot ID:
- P50336
- Molecular Weight:
- 50764.8 Da
References
- Zuo Y, Yang SG, Jiang LL, Hao GF, Wang ZF, Wu QY, Xi Z, Yang GF: Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors. Bioorg Med Chem. 2012 Jan 1;20(1):296-304. doi: 10.1016/j.bmc.2011.10.079. Epub 2011 Nov 10. [22130420 ]
- 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:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 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:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 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:
- Identical protein binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- ADORA2A
- Uniprot ID:
- P29274
- Molecular Weight:
- 44706.925 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:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
- Gene Name:
- CSF1
- Uniprot ID:
- P09603
- Molecular Weight:
- 60178.885 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 ]