Imazaquin
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Basic Info
| Common Name | Imazaquin(F05088) |
| 2D Structure | |
| Description | Imazaquin is primarily used as a herbicide to control weed growth on lawns and turf fields. Due to the fact that it is highly effective and selective, it is one of the most commonly used herbicides.It is classified as an imidazolinone herbicide Imazaquin inhibits the acetohydroxy acid synthase (AHAS) enzyme which is responsible for the synthesis of the branched chain amino acids valine, leucine, and isoleucine. When applied, imazaquin halts weed growth which eventually kills the weed or causes the weed to die due to its incapability to compete with surrounding vegetation. |
| FRCD ID | F05088 |
| CAS Number | 81335-37-7 |
| PubChem CID | 54739 |
| Formula | C17H17N3O3 |
| IUPAC Name | 2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)quinoline-3-carboxylic acid |
| InChI Key | CABMTIJINOIHOD-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H17N3O3/c1-9(2)17(3)16(23)19-14(20-17)13-11(15(21)22)8-10-6-4-5-7-12(10)18-13/h4-9H,1-3H3,(H,21,22)(H,19,20,23) |
| Canonical SMILES | CC(C)C1(C(=O)NC(=N1)C2=NC3=CC=CC=C3C=C2C(=O)O)C |
| Isomeric SMILES | CC(C)C1(C(=O)NC(=N1)C2=NC3=CC=CC=C3C=C2C(=O)O)C |
| Synonyms |
IMAZAQUIN
81335-37-7
Imazaquin acid
Scepter Herbicide
Caswell No. 003C
Imazaquin [BSI:ISO]
Imazaquine [ISO-French]
HSDB 6677
2-(4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-3-quinolinecarboxylic acid
EPA Pesticide Chemical Code 128840
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Quinoline carboxylic acids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Quinoline carboxylic acids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Quinoline-3-carboxylic acid - Alpha-amino acid or derivatives - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Imidazolyl carboxylic acid derivative - Imidazolinone - Pyridine - Benzenoid - 2-imidazoline - Heteroaromatic compound - Carboximidamide - Azacycle - Amidine - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Carboxylic acid amidine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 311.341 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 545 |
| Monoisotopic Mass | 311.127 |
| Exact Mass | 311.127 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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- | 0.6016 |
| Human Intestinal Absorption | HIA+ | 0.9852 |
| Caco-2 Permeability | Caco2- | 0.6644 |
| P-glycoprotein Substrate | Substrate | 0.5743 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7119 |
| Non-inhibitor | 0.6449 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9145 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7618 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6873 |
| CYP450 2D6 Substrate | Non-substrate | 0.8009 |
| CYP450 3A4 Substrate | Non-substrate | 0.5000 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6060 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8694 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8287 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7318 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9989 |
| Non-inhibitor | 0.8674 | |
| AMES Toxicity | Non AMES toxic | 0.7210 |
| Carcinogens | Non-carcinogens | 0.7899 |
| Fish Toxicity | High FHMT | 0.6871 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8382 |
| Honey Bee Toxicity | Low HBT | 0.8490 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7715 |
| Carcinogenicity (Three-class) | Non-required | 0.5952 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9585 | LogS |
| Caco-2 Permeability | 0.6756 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9143 | LD50, mol/kg |
| Fish Toxicity | 1.5305 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6270 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Apricot | Japan | 0.05ppm | |||
| Nectarine | Japan | 0.05ppm | |||
| Peach | Japan | 0.05ppm | |||
| Loquat | Japan | 0.05ppm | |||
| Quince | Japan | 0.05ppm | |||
| Pear | Japan | 0.05ppm | |||
| Japanese Pear | Japan | 0.05ppm | |||
| Apple | Japan | 0.05ppm | |||
| Other Citrus Fruits | Japan | 0.05ppm | |||
| Lime | Japan | 0.05ppm | |||
| Grapefruit | Japan | 0.05ppm | |||
| Orange(Including Navel Orange) | Japan | 0.05ppm | |||
| Lemon | Japan | 0.05ppm | |||
| Citrus Natsudaidai,Whole | Japan | 0.05ppm | |||
| Unshu Orange,Pulp | Japan | 0.05ppm | |||
| Other Vegetables | Japan | 0.05ppm | |||
| Other Mushrooms | Japan | 0.05ppm | |||
| Shiitake Mushroom | Japan | 0.05ppm | |||
| Button Mushroom | Japan | 0.05ppm | |||
| Green Soybeans | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Analysis of the Photodegradation of the Imidazolinone Herbicides Imazamox,Imazapic, Imazaquin, and Imazamethabenz-methyl in Aqueous Solution. | J Agric Food Chem | 2015 Dec 23 | 26616105 |
| Faster degradation of herbicidally-active enantiomer of imidazolinones in soils. | Chemosphere | 2010 May | 20416927 |
| Analytical method for simultaneous determination of pesticide and veterinary drugresidues in milk by CE-MS. | Electrophoresis | 2009 May | 19384986 |
| Improved extraction and clean-up of imidazolinone herbicides from soil solutions using different solid-phase sorbents. | J Chromatogr A | 2009 Jun 26 | 19447395 |
| [Simultaneous determination of residues of six imidazolinone herbicides in adzukibeans by high performance liquid chromatography-electrospray ion trap tandem massspectrometry]. | Se Pu | 2008 Nov | 19253552 |
| Soil pH on mobility of imazaquin in oxisols with positive balance of charges. | J Agric Food Chem | 2005 May 18 | 15884845 |
| Imidazolinone-tolerant crops: history, current status and future. | Pest Manag Sci | 2005 Mar | 15627242 |
| Application of capillary electrophoresis to study the enantioselectivetransformation of five chiral pesticides in aerobic soil slurries. | J Agric Food Chem | 2005 Aug 10 | 16076090 |
| Water purification from organic pollutants by optimized micelle-clay systems. | Environ Sci Technol | 2005 Apr 1 | 15871274 |
| Effect of organic amendments on the retention and mobility of imazaquin in soils. | J Agric Food Chem | 2004 Jul 14 | 15237957 |
| Assessment of the ability of Imazaquin herbicide to induce chromosomal aberrations in vitro in cultured Chinese hamster ovary cells and micronuclei in vivo in mice. | Food Chem Toxicol | 2004 Aug | 15207374 |
| Sorption and mobility of 14C-labeled imazaquin and metolachlor in four soils asinfluenced by soil properties. | J Agric Food Chem | 2003 Sep 10 | 12952429 |
| 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in capillary morphogenesis.
- Gene Name:
- SELE
- Uniprot ID:
- P16581
- Molecular Weight:
- 66654.575 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for TNFSF5/CD40LG. Transduces TRAF6- and MAP3K8-mediated signals that activate ERK in macrophages and B cells, leading to induction of immunoglobulin secretion.
- Gene Name:
- CD40
- Uniprot ID:
- P25942
- Molecular Weight:
- 30618.76 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 ]
- 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:
- 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:
- 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]