Imazapyr
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Basic Info
| Common Name | Imazapyr(F05424) |
| 2D Structure | |
| Description | Imazapyr is a non-selective herbicide for non-crop land applications which is particularly effective on hard-to-control perennial grasses. Its mode of action is non-selective and absorbed by foliage and rapidly translocated. Imazapyr is absorbed by the leaves and roots, and moves rapidly through the plant. It accumulates in the meristem region (active growth region) of the plant. In plants, imazapyr disrupts protein synthesis and interferes with cell growth and DNA synthesis. It controls vegetation by interfering with an enzyme pathway. It inhibits acetolactate synthase. It is used for the control of a broad range of weeds including terrestrial annual and perennial grasses and broadleaved herbs, woody species, and riparian and emergent aquatic species. It is used to eliminate Lithocarpus densiflorus (Tan Oak) and Arbutus menziesii (Pacific Madrone). Additionally, imazapyr is used to control annual and perennial grass and broadleaved weeds, brush, vines and many deciduous trees. |
| FRCD ID | F05424 |
| CAS Number | 81334-34-1 |
| PubChem CID | 54738 |
| Formula | C13H15N3O3 |
| IUPAC Name | 2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid |
| InChI Key | CLQMBPJKHLGMQK-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H15N3O3/c1-7(2)13(3)12(19)15-10(16-13)9-8(11(17)18)5-4-6-14-9/h4-7H,1-3H3,(H,17,18)(H,15,16,19) |
| Canonical SMILES | CC(C)C1(C(=O)NC(=N1)C2=C(C=CC=N2)C(=O)O)C |
| Isomeric SMILES | CC(C)C1(C(=O)NC(=N1)C2=C(C=CC=N2)C(=O)O)C |
| Synonyms |
Imazapyr acid
Chopper
Imazapyr [ANSI:BSI:ISO]
Imazapyr
81334-34-1
Charper
Arsenal
Arsenal 250A
(+-)-Imazapyr
Caswell No. 003F
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Alpha amino acids and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Alpha-amino acid or derivatives - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Imidazolyl carboxylic acid derivative - Imidazolinone - Pyridine - 2-imidazoline - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Carboxylic acid amidine - Carboxylic acid - Monocarboxylic acid or derivatives - Amidine - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 261.281 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 433 |
| Monoisotopic Mass | 261.111 |
| Exact Mass | 261.111 |
| XLogP | 1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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- | 0.6229 |
| Human Intestinal Absorption | HIA+ | 0.9582 |
| Caco-2 Permeability | Caco2- | 0.6279 |
| P-glycoprotein Substrate | Non-substrate | 0.5558 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8591 |
| Non-inhibitor | 0.8893 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9339 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8260 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7218 |
| CYP450 2D6 Substrate | Non-substrate | 0.8034 |
| CYP450 3A4 Substrate | Non-substrate | 0.5992 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7158 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8385 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8960 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6392 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8637 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9072 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9990 |
| Non-inhibitor | 0.9453 | |
| AMES Toxicity | Non AMES toxic | 0.7821 |
| Carcinogens | Non-carcinogens | 0.7960 |
| Fish Toxicity | Low FHMT | 0.7042 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6573 |
| Honey Bee Toxicity | Low HBT | 0.8915 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7742 |
| Carcinogenicity (Three-class) | Non-required | 0.6417 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1688 | LogS |
| Caco-2 Permeability | 0.7048 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7100 | LD50, mol/kg |
| Fish Toxicity | 1.9793 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3928 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis optimization of oil palm empty fruit bunch and rice husk biochars forremoval of imazapic and imazapyr herbicides. | J Environ Manage | 2017 May 15 | 28226259 |
| Effects of herbicides on Behr's metalmark butterfly, a surrogate species for the endangered butterfly, Lange's metalmark. | Environ Pollut | 2012 May | 22310058 |
| Comparability of imazapyr-resistant Arabidopsis created by transgenesis andmutagenesis. | Transgenic Res | 2012 Dec | 22430369 |
| Faster degradation of herbicidally-active enantiomer of imidazolinones in soils. | Chemosphere | 2010 May | 20416927 |
| Crops with target-site herbicide resistance for Orobanche and Striga control. | Pest Manag Sci | 2009 May | 19280593 |
| Improved extraction and clean-up of imidazolinone herbicides from soil solutions using different solid-phase sorbents. | J Chromatogr A | 2009 Jun 26 | 19447395 |
| CSR1, the sole target of imidazolinone herbicide in Arabidopsis thaliana. | Plant Cell Physiol | 2007 Sep | 17693453 |
| Photochemical degradation of imazamox in aqueous solution: influence of metalions and anionic species on the ultraviolet photolysis. | J Agric Food Chem | 2006 May 17 | 19127738 |
| Imidazolinone-tolerant crops: history, current status and future. | Pest Manag Sci | 2005 Mar | 15627242 |
| Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides. | J Agric Food Chem | 2002 Jun 5 | 12033799 |
| Transformation of carrots with mutant acetolactate synthase for Orobanche(broomrape) control. | Pest Manag Sci | 2002 Dec | 12476991 |
| Role of ferrihydrite in adsorption of three imidazolinone herbicides. | J Agric Food Chem | 2001 Mar | 11312857 |
| Synthesis of dimethyl derivatives of imidazolinone herbicides: their use inefficient gas chromatographic methods for the determination of these herbicides. | J Agric Food Chem | 2000 Dec | 11141261 |
Targets
- 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:
- 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Knudsen TB, Houck KA, Sipes NS, Singh AV, Judson RS, Martin MT, Weissman A, Kleinstreuer NC, Mortensen HM, Reif DM, Rabinowitz JR, Setzer RW, Richard AM, Dix DJ, Kavlock RJ: Activity profiles of 309 ToxCast chemicals evaluated across 292 biochemical targets. Toxicology. 2011 Mar 28;282(1-2):1-15. doi: 10.1016/j.tox.2010.12.010. Epub 2011 Jan 18. [21251949 ]