Fluroxypyr
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Basic Info
| Common Name | Fluroxypyr(F05077) |
| 2D Structure | |
| Description | Fluroxypyr is an herbicide in the class of synthetic auxins. It is used to control broadleaf weeds and woody brush. It is formulated as the 1-methylheptyl ester (fluroxypyr-MHE). |
| FRCD ID | F05077 |
| CAS Number | 69377-81-7 |
| PubChem CID | 50465 |
| Formula | C7H5Cl2FN2O3 |
| IUPAC Name | 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetic acid |
| InChI Key | MEFQWPUMEMWTJP-UHFFFAOYSA-N |
| InChI | InChI=1S/C7H5Cl2FN2O3/c8-3-5(11)4(9)7(12-6(3)10)15-1-2(13)14/h1H2,(H2,11,12)(H,13,14) |
| Canonical SMILES | C(C(=O)O)OC1=NC(=C(C(=C1Cl)N)Cl)F |
| Isomeric SMILES | C(C(=O)O)OC1=NC(=C(C(=C1Cl)N)Cl)F |
| Synonyms |
4-Amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid
Fluroxypyr
69377-81-7
Advance
Fluroxypyr [BSI:ISO]
EF 689
UNII-8O40SHO197
HSDB 6655
((4-Amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy)acetic acid
FF4014
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Halopyridines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Polyhalopyridines |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Polyhalopyridine - Alkyl aryl ether - Aminopyridine - 2-halopyridine - Aryl chloride - Aryl fluoride - Aryl halide - Heteroaromatic compound - Amino acid or derivatives - Amino acid - Azacycle - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Organooxygen compound - Carbonyl group - Primary amine - Organic oxide - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as polyhalopyridines. These are organic compounds containing a pyridine ring substituted at two or more positions by a halogen atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 255.026 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Complexity | 246 |
| Monoisotopic Mass | 253.966 |
| Exact Mass | 253.966 |
| XLogP | 1.8 |
| 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+ | 0.8820 |
| Human Intestinal Absorption | HIA+ | 0.8316 |
| Caco-2 Permeability | Caco2- | 0.6039 |
| P-glycoprotein Substrate | Non-substrate | 0.7910 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9381 |
| Non-inhibitor | 0.9826 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9349 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5780 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8646 |
| CYP450 2D6 Substrate | Non-substrate | 0.8203 |
| CYP450 3A4 Substrate | Non-substrate | 0.5975 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6149 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9218 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8505 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8284 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9359 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8217 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9977 |
| Non-inhibitor | 0.8747 | |
| AMES Toxicity | Non AMES toxic | 0.7657 |
| Carcinogens | Non-carcinogens | 0.8656 |
| Fish Toxicity | Low FHMT | 0.6179 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8406 |
| Honey Bee Toxicity | Low HBT | 0.9180 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7744 |
| Carcinogenicity (Three-class) | Non-required | 0.5313 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5081 | LogS |
| Caco-2 Permeability | 0.6187 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0565 | LD50, mol/kg |
| Fish Toxicity | 1.5526 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2817 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,) | 0130020 | European Union | 0.01* | 21/01/2016 | |
| Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl... | 0140040 | European Union | 0.01* | 21/01/2016 | |
| (a) grapes | 0151000 | European Union | 0.01* | 21/01/2016 | |
| Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,) | 0153020 | European Union | 0.01* | 21/01/2016 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 0.01* | 21/01/2016 | |
| Breadfruits (Jackfruits, Other species of genus Artocarpus, not elsewhere mentioned,) | 0163090 | European Union | 0.01* | 21/01/2016 | |
| Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,) | 0212010 | European Union | 0.01* | 21/01/2016 | |
| Others (2) | 0241990 | European Union | 0.01* | 21/01/2016 | |
| Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ... | 0260010 | European Union | 0.01* | 21/01/2016 | |
| Oil palms kernels (Argan nuts, Babassu palm nuts, Jojoba nuts, Shea nuts,) | 0402020 | European Union | 0.01* | 21/01/2016 | |
| Buckwheat and other pseudocereals (Amaranth/kiwicha, Amaranth/kiwicha, Amaranth/kiwicha, Kaniwa/canihua, Quinoa, Chia seeds,) | 0500020 | European Union | 0.01* | 21/01/2016 | |
| Fenugreek | 0810080 | European Union | 0.05* | 21/01/2016 | |
| Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,) | 0820060 | European Union | 0.05* | 21/01/2016 | |
| Muscle | 1017010 | European Union | 0.01* | 21/01/2016 | |
| Kidney | 1017040 | European Union | 0.3 | 21/01/2016 | |
| Others (2) (Bactrian camel, Dromedary, Elk/moose, Reindeer, Other milk producer animals,) | 1020990 | European Union | 0.06 | 21/01/2016 | |
| Pear | Japan | 0.05ppm | |||
| Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,) | 0243010 | European Union | 0.01* | 21/01/2016 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.01* | 21/01/2016 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 2 | 21/01/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Method validation and dissipation kinetics of four herbicides in maize and soilusing QuEChERS sample preparation and liquid chromatography tandem massspectrometry. | Food Chem | 2016 Jan 1 | 26213040 |
| The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides. | Bioorg Med Chem | 2016 Feb 1 | 26321602 |
| Differences in Germination, Growth, and Fecundity Characteristics ofDicamba-Fluroxypyr-Resistant and Susceptible Kochia scoparia. | PLoS One | 2016 Aug 18 | 27537419 |
| Glyceria maxima as new test species for the EU risk assessment for herbicides: a microcosm study. | Ecotoxicology | 2015 Mar | 25380672 |
| 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 |
| Determination of the herbicide fluroxypyr in oil matrices. | J Environ Sci Health B | 2008 Feb | 18246505 |
| Prediction of the adsorption of ionizable pesticides in soils. | J Agric Food Chem | 2007 Mar 21 | 17295514 |
| Physiological and biochemical characterization of quinclorac resistance in afalse cleavers (Galium spurium L.) biotype. | J Agric Food Chem | 2005 Feb 23 | 15713032 |
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
- 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:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 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:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 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:
- Serine-type endopeptidase inhibitor activity
- Specific Function:
- Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
- Gene Name:
- SERPINE1
- Uniprot ID:
- P05121
- Molecular Weight:
- 45059.695 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin generated.
- Gene Name:
- THBD
- Uniprot ID:
- P07204
- Molecular Weight:
- 60328.72 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:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 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 ]