Clopyralid
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Basic Info
| Common Name | Clopyralid(F05399) |
| 2D Structure | |
| Description | Clopyralid is a selective herbicide used for control of broadleaf weeds, especially thistles and clovers. Clopyralid is in the picolinic acid family of herbicides, which also includes aminopyralid, picloram, triclopyr, and several less common herbicides. For control of Creeping Thistle, Cirsium arvense, a noxious, perennial weed, clopyralid is one of the few effective herbicides available. It is particularly damaging to peas, tomatoes and sunflowers and can render potatoes, lettuce and spinach inedible. It does not affect members of the family Poaceae (grasses). |
| FRCD ID | F05399 |
| CAS Number | 1702-17-6 |
| PubChem CID | 15553 |
| Formula | C6H3Cl2NO2 |
| IUPAC Name | 3,6-dichloropyridine-2-carboxylic acid |
| InChI Key | HUBANNPOLNYSAD-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H3Cl2NO2/c7-3-1-2-4(8)9-5(3)6(10)11/h1-2H,(H,10,11) |
| Canonical SMILES | C1=CC(=NC(=C1Cl)C(=O)O)Cl |
| Isomeric SMILES | C1=CC(=NC(=C1Cl)C(=O)O)Cl |
| Synonyms |
2-Pyridinecarboxylic acid, 3,6-dichloro-
1702-17-6
CLOPYRALID
3,6-Dichloropyridine-2-carboxylic acid
3,6-Dichloropicolinic acid
3,6-Dichloro-2-pyridinecarboxylic acid
Lontrel
Clopyralide
Benzalox
Cirtoxin
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridinecarboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridinecarboxylic acids |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyridine carboxylic acid - Polyhalopyridine - 2-halopyridine - Aryl chloride - Aryl halide - Vinylogous halide - Heteroaromatic compound - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 191.995 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 165 |
| Monoisotopic Mass | 190.954 |
| Exact Mass | 190.954 |
| XLogP | 2.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.9720 |
| Human Intestinal Absorption | HIA+ | 0.9859 |
| Caco-2 Permeability | Caco2+ | 0.8129 |
| P-glycoprotein Substrate | Non-substrate | 0.8567 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9899 |
| Non-inhibitor | 0.9972 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9099 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8329 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7952 |
| CYP450 2D6 Substrate | Non-substrate | 0.8791 |
| CYP450 3A4 Substrate | Non-substrate | 0.7356 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8620 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8968 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9595 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9257 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9618 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9784 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9752 |
| Non-inhibitor | 0.9792 | |
| AMES Toxicity | Non AMES toxic | 0.9767 |
| Carcinogens | Non-carcinogens | 0.8900 |
| Fish Toxicity | Low FHMT | 0.5234 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6702 |
| Honey Bee Toxicity | Low HBT | 0.6693 |
| Biodegradation | Not ready biodegradable | 0.8312 |
| Acute Oral Toxicity | III | 0.7866 |
| Carcinogenicity (Three-class) | Non-required | 0.7863 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1077 | LogS |
| Caco-2 Permeability | 1.5737 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6815 | LD50, mol/kg |
| Fish Toxicity | 1.8211 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1633 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Oats | Canada | 2mg/kg | |||
| Muscle | 1014010 | European Union | 0.08 | 07/05/2012 | |
| Fat | 1014020 | European Union | 0.05* | 07/05/2012 | |
| Liver | 1014030 | European Union | 0.06 | 07/05/2012 | |
| Kidney | 1014040 | European Union | 0.4 | 07/05/2012 | |
| Others (2) | 1014990 | European Union | 0.05* | 07/05/2012 | |
| (e) equine (Ass, Hinny, Horse, Mule,) | 1015000 | European Union | 0.05* | 07/05/2012 | |
| Muscle | 1015010 | European Union | 0.05* | 07/05/2012 | |
| Fat | 1015020 | European Union | 0.05* | 07/05/2012 | |
| Liver | 1015030 | European Union | 0.05* | 07/05/2012 | |
| Kidney | 1015040 | European Union | 0.05* | 07/05/2012 | |
| Edible offals (other than liver and kidney) | 1015050 | European Union | 0.05* | 07/05/2012 | |
| Others (2) | 1015990 | European Union | 0.05* | 07/05/2012 | |
| Muscle | 1016010 | European Union | 0.05* | 07/05/2012 | |
| Fat | 1016020 | European Union | 0.05* | 07/05/2012 | |
| Liver | 1016030 | European Union | 0.05* | 07/05/2012 | |
| Kidney | 1016040 | European Union | 0.05* | 07/05/2012 | |
| Edible offals (other than liver and kidney) | 1016050 | European Union | 0.05* | 07/05/2012 | |
| Others (2) | 1016990 | European Union | 0.05* | 07/05/2012 | |
| (g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh... | 1017000 | European Union | 0.05* | 07/05/2012 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Zinc delivery from non-woven fibres within a therapeutic nipple shield. | Int J Pharm | 2018 Feb 15 | 29288810 |
| Occurrence of a stonefish toxin-like toxin in the venom of the rabbitfish Siganusfuscescens. | Toxicon | 2017 Dec 15 | 29055787 |
| Are pesticide residues in honey related to oilseed rape treatments? | Chemosphere | 2017 Dec | 28898772 |
| The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides. | Bioorg Med Chem | 2016 Feb 1 | 26321602 |
| Field degradation of aminopyralid and clopyralid and microbial community responseto application in Alaskan soils. | Environ Toxicol Chem | 2016 Feb | 26313564 |
| Restoration of rare earth mine areas: organic amendments and phytoremediation. | Environ Sci Pollut Res Int | 2015 Nov | 26139395 |
| Effects of a herbicide mixture on primary and bacterial productivity in fourprairie wetlands with varying salinities: an enclosure approach. | Sci Total Environ | 2015 Apr 15 | 25644848 |
| Wasp voodoo rituals, venom-cocktails, and the zombification of cockroach hosts. | Integr Comp Biol | 2014 Jul | 24706086 |
| Sensory arsenal on the stinger of the parasitoid jewel wasp and its possible rolein identifying cockroach brains. | PLoS One | 2014 Feb 26 | 24586962 |
| Implications for food safety of the uptake by tomato of 25 trace-elements from a phosphogypsum amended soil from SW Spain. | J Hazard Mater | 2014 Feb 15 | 24389006 |
| Multiresidue analysis of pesticides in urine of healthy adult companion dogs. | Environ Sci Technol | 2014 Dec 16 | 25365583 |
| [Using kenaf (Hibiscus cannabinus) to reclaim multi-metal contaminated acidicsoil]. | Ying Yong Sheng Tai Xue Bao | 2013 Mar | 23755502 |
| Development and validation of an ultra high performance liquid chromatographytandem mass spectrometry method for determination of 10 cephalosporins anddesacetylcefapirin in milk. | J Chromatogr B Analyt Technol Biomed Life Sci | 2013 Jul 15 | 23747425 |
| Influence of usage and chemical-physical properties on the atmospheric transport and deposition of pesticides to agricultural regions of Manitoba, Canada. | Chemosphere | 2013 Feb | 23260250 |
| Proteinaceous toxins from three species of scorpaeniform fish (lionfish Pteroislunulata, devil stinger Inimicus japonicus and waspfish Hypodytes rubripinnis):close similarity in properties and primary structures to stonefish toxins. | Toxicon | 2013 Aug | 23665450 |
| Effects of herbicide mixture on microbial communities in prairie wetlandecosystems: a whole wetland approach. | Sci Total Environ | 2012 Oct 1 | 22846761 |
| Effects of glyphosate and two herbicide mixtures on microbial communities inprairie wetland ecosystems: a mesocosm approach. | J Environ Qual | 2012 May-Jun | 22565255 |
| Simultaneous determination of aminopyralid, clopyralid, and picloram residues in vegetables and fruits using ultra-performance liquid chromatography/tandem massspectrometry. | J AOAC Int | 2012 Mar-Apr | 22649944 |
| Hemprich's long-eared bat (Otonycteris hemprichii) as a predator of scorpions:whispering echolocation, passive gleaning and prey selection. | J Comp Physiol A Neuroethol Sens Neural Behav Physiol | 2011 May | 21086132 |
| Decontamination of aquatic vegetable leaves by removing trace toxic metals during pickling process with acetic acid solution. | Ecol Food Nutr | 2011 Jul-Aug | 21888602 |
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:
- Interleukin-8 receptor binding
- Specific Function:
- IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively.
- Gene Name:
- CXCL8
- Uniprot ID:
- P10145
- Molecular Weight:
- 11097.98 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:
- 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:
- 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:
- Cytokine activity
- Specific Function:
- Cytokine that affects the growth, movement, or activation state of cells that participate in immune and inflammatory response. Chemotactic for activated T-cells. Binds to CXCR3.
- Gene Name:
- CXCL9
- Uniprot ID:
- Q07325
- Molecular Weight:
- 14018.72 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:
- 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:
- 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 ]