Picloram
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Basic Info
| Common Name | Picloram(F05430) |
| 2D Structure | |
| Description | Picloram is a persistent systemic herbicide used for general woody plant control and a broad-leaved weeds on non-crop and utility areas. It also controls a wide range of broad-leaved weeds, but most grasses are resistant. A chlorinated derivative of picolinic acid, picloram is in the pyridine family of herbicides. It is systemically absorbed by roots and leaves and translocated. |
| FRCD ID | F05430 |
| CAS Number | 1918-02-1 |
| PubChem CID | 15965 |
| Formula | C6H3Cl3N2O2 |
| IUPAC Name | 4-amino-3,5,6-trichloropyridine-2-carboxylic acid |
| InChI Key | NQQVFXUMIDALNH-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13) |
| Canonical SMILES | C1(=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl)N |
| Isomeric SMILES | C1(=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl)N |
| Synonyms |
4-Amino-3,5,6-trichloropyridine-2-carboxylic acid
PICLORAM
1918-02-1
4-Amino-3,5,6-trichloropicolinic acid
Tordon
Borolin
Grazon
Amdon
2-Pyridinecarboxylic acid, 4-amino-3,5,6-trichloro-
K-Pin
|
| 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 - Aminopyridine - 2-halopyridine - Aryl chloride - Aryl halide - Heteroaromatic compound - Vinylogous halide - Amino acid or derivatives - Amino acid - Carboxylic acid derivative - Azacycle - Carboxylic acid - Monocarboxylic acid or derivatives - Amine - Organonitrogen compound - Organochloride - Organohalogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - 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 | 241.452 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 216 |
| Monoisotopic Mass | 239.926 |
| Exact Mass | 239.926 |
| XLogP | 2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.8157 |
| Human Intestinal Absorption | HIA+ | 0.9179 |
| Caco-2 Permeability | Caco2+ | 0.6613 |
| P-glycoprotein Substrate | Non-substrate | 0.8324 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9880 |
| Non-inhibitor | 0.9827 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9293 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5648 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8512 |
| CYP450 2D6 Substrate | Non-substrate | 0.9018 |
| CYP450 3A4 Substrate | Non-substrate | 0.7613 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6256 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8916 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9196 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9515 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8329 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9173 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9885 |
| Non-inhibitor | 0.9582 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.7854 |
| Fish Toxicity | Low FHMT | 0.6068 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6205 |
| Honey Bee Toxicity | Low HBT | 0.9051 |
| Biodegradation | Not ready biodegradable | 0.9932 |
| Acute Oral Toxicity | IV | 0.6154 |
| Carcinogenicity (Three-class) | Non-required | 0.7237 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8128 | LogS |
| Caco-2 Permeability | 1.2693 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5001 | LD50, mol/kg |
| Fish Toxicity | 1.8758 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2302 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry,Eggs | Japan | 0.05ppm | |||
| Chicken,Eggs | Japan | 0.05ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.1ppm | |||
| Chicken,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.1ppm | |||
| Chicken,Kidney | Japan | 0.1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.1ppm | |||
| Chicken,Liver | Japan | 0.1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.05ppm | |||
| Chicken,Fat | Japan | 0.05ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.05ppm | |||
| Chicken,Muscle | Japan | 0.05ppm | |||
| Milk | Japan | 0.05ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 2ppm | |||
| Pig,Edible Offal | Japan | 2ppm | |||
| Cattle,Edible Offal | Japan | 2ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 3ppm | |||
| Pig,Kidney | Japan | 3ppm | |||
| Cattle,Kidney | Japan | 3ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 2ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Persistence of auxinic herbicides applied on pasture and toxicity for succeeding crops. | An Acad Bras Cienc | 2018 Apr-Jun | 29694496 |
| Somatic embryogenesis and direct as well as indirect organogenesis in Liliumpumilum DC. Fisch., an endangered ornamental and medicinal plant. | Biosci Biotechnol Biochem | 2016 Oct | 27285948 |
| The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides. | Bioorg Med Chem | 2016 Feb 1 | 26321602 |
| Induction of somatic embryogenesis in explants of shoot cultures established fromadult Eucalyptus globulus and E. saligna × E. maidenii trees. | Tree Physiol | 2015 Jun | 25877768 |
| 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 |
| Compositional changes in cell wall polysaccharides from apple fruit calluscultures modulated by different plant growth regulators. | Plant Sci | 2012 Apr | 22325878 |
| Simultaneous determination of pesticides, biopesticides and mycotoxins in organic products applying a quick, easy, cheap, effective, rugged and safe extraction procedure and ultra-high performance liquid chromatography-tandem mass spectrometry. | J Chromatogr A | 2011 Mar 18 | 21292276 |
| Residue dynamics of clopyralid and picloram in rape plant rapeseed and fieldsoil. | Bull Environ Contam Toxicol | 2011 Jan | 21184051 |
| Rapid and complete degradation of the herbicide picloram by Lipomyceskononenkoae. | J Agric Food Chem | 2009 Jun 10 | 19489626 |
| Picloram resistance in transgenic tobacco expressing an anti-picloram scFvantibody is due to reduced translocation. | J Agric Food Chem | 2007 Jan 10 | 17199320 |
| Layered double hydroxides as supports for the slow release of acid herbicides. | J Agric Food Chem | 2006 Aug 9 | 16881703 |
| Physiological and biochemical characterization of quinclorac resistance in afalse cleavers (Galium spurium L.) biotype. | J Agric Food Chem | 2005 Feb 23 | 15713032 |
| Hemoglobin promotes somatic embryogenesis in peanut cultures. | Artif Cells Blood Substit Immobil Biotechnol | 2004 Feb | 15027807 |
| Off-line solid-phase microextraction and capillary electrophoresis massspectrometry to determine acidic pesticides in fruits. | Anal Chem | 2003 Feb 1 | 12585470 |
| The effect of titanium dioxide alumina beads on the photocatalytic degradation ofpicloram in water. | J Agric Food Chem | 2003 Apr 23 | 12696954 |
| Synthesis of ligand-specific phage-display ScFv against the herbicide picloram bydirect cloning from hyperimmunized mouse. | J Agric Food Chem | 2001 Aug | 11513639 |
| Gas chromatographic determination of N-nitrosodialkanolamines in herbicide Di- ortrialkanolamine formulations. | J Assoc Off Anal Chem | 1988 Mar-Apr | 3384780 |
Targets
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 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 ]