Imazamox
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Basic Info
| Common Name | Imazamox(F05086) |
| 2D Structure | |
| Description | Imazamox is a member of the imidazolinone class of herbicides. It is registered for post-emergence control of broadleaf weeds and grass in alfalfa, edible legumes and soybeans. It is a systemic herbicide that moves throughout the plant tissue and prevents plants from producing an essential enzyme, acetolactate synthase (ALS), which is not found in animals. This enzyme is key for the biosynthesis of branched chain amino acids. Susceptible plants will stop growing soon after treatment, but plant death and decomposition will occur over several weeks. |
| FRCD ID | F05086 |
| CAS Number | 114311-32-9 |
| PubChem CID | 86137 |
| Formula | C15H19N3O4 |
| IUPAC Name | 5-(methoxymethyl)-2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid |
| InChI Key | NUPJIGQFXCQJBK-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H19N3O4/c1-8(2)15(3)14(21)17-12(18-15)11-10(13(19)20)5-9(6-16-11)7-22-4/h5-6,8H,7H2,1-4H3,(H,19,20)(H,17,18,21) |
| Canonical SMILES | CC(C)C1(C(=O)NC(=N1)C2=NC=C(C=C2C(=O)O)COC)C |
| Isomeric SMILES | CC(C)C1(C(=O)NC(=N1)C2=NC=C(C=C2C(=O)O)COC)C |
| Synonyms |
(+-)-Imazamox
Imazamox
114311-32-9
Pulsar
Raptor
Imazamox [ISO]
Raptor (herbicide)
HSDB 7013
AC 299263
CL 299263
|
| 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 - N-acylimine - Amidine - Carboxylic acid amidine - Carboxylic acid - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - 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 | 305.334 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Complexity | 491 |
| Monoisotopic Mass | 305.138 |
| Exact Mass | 305.138 |
| XLogP | 0.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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- | 0.8519 |
| Human Intestinal Absorption | HIA+ | 0.8407 |
| Caco-2 Permeability | Caco2- | 0.6431 |
| P-glycoprotein Substrate | Substrate | 0.6141 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8303 |
| Non-inhibitor | 0.6633 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9026 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6701 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7580 |
| CYP450 2D6 Substrate | Non-substrate | 0.8306 |
| CYP450 3A4 Substrate | Non-substrate | 0.5061 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6199 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7902 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8771 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7156 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8553 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9140 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9982 |
| Non-inhibitor | 0.9154 | |
| AMES Toxicity | Non AMES toxic | 0.6599 |
| Carcinogens | Non-carcinogens | 0.8641 |
| Fish Toxicity | Low FHMT | 0.7339 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8302 |
| Honey Bee Toxicity | Low HBT | 0.8537 |
| Biodegradation | Not ready biodegradable | 0.9962 |
| Acute Oral Toxicity | III | 0.7684 |
| Carcinogenicity (Three-class) | Non-required | 0.6387 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.9510 | LogS |
| Caco-2 Permeability | 0.4403 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8168 | LD50, mol/kg |
| Fish Toxicity | 1.4931 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5118 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.05* | 05/05/2016 | |
| Raspberries (red and yellow) (Arctic brambles/arctic raspberries/nectar berries, Black raspberries, Korean black raspberries, Korean raspberries, Nectar raspberries, Wineberries/Japanese wineberries,) | 0153030 | European Union | 0.05* | 05/05/2016 | |
| 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 | 0.05* | 05/05/2016 | |
| Yams (Amazonian yam beans/potato beans, American groundnuts tubers, Andean yam beans, Mexican yam beans,) | 0212030 | European Union | 0.05* | 05/05/2016 | |
| Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater... | 0213040 | European Union | 0.05* | 05/05/2016 | |
| Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba... | 0243020 | European Union | 0.05* | 05/05/2016 | |
| 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 | 0.05* | 05/05/2016 | |
| Beans (without 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 bean... | 0260020 | European Union | 0.05* | 05/05/2016 | |
| Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,) | 0500040 | European Union | 0.05* | 05/05/2016 | |
| 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 | 0.1* | 05/05/2016 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.1* | 05/05/2016 | |
| Cardamom (Marjoram, Star anise,) | 0820040 | European Union | 0.1* | 05/05/2016 | |
| 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 | 0.1* | 05/05/2016 | |
| Sweet potatoes | 0212020 | European Union | 0.05* | 05/05/2016 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 05/05/2016 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 05/05/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 05/05/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 05/05/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 05/05/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 05/05/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of imidazolinone herbicide tolerant borage (Borago officinalis L.). | Plant Sci | 2017 Sep | 28716422 |
| Occurrence of Different Resistance Mechanisms to Acetolactate Synthase Inhibitorsin European Sorghum halepense. | J Agric Food Chem | 2017 Aug 30 | 28767243 |
| Effect of two commercial herbicides on life history traits of a human diseasevector, Aedes aegypti, in the laboratory setting. | Ecotoxicology | 2016 Jul | 26965703 |
| 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 |
| Physiological and molecular basis of acetolactate synthase-inhibiting herbicideresistance in barnyardgrass (Echinochloa crus-galli). | J Agric Food Chem | 2013 Jan 16 | 23237199 |
| Pleiotropic effects of herbicide-resistance genes on crop yield: a review. | Pest Manag Sci | 2013 Aug | 23457026 |
| Leaching of three imidazolinone herbicides during sprinkler irrigation. | J Environ Qual | 2012 May-Jun | 22565269 |
| Identification of a hybridization window that facilitates sizeable reductions of pollen-mediated gene flow in spring wheat. | Transgenic Res | 2010 Jun | 19763864 |
| 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 |
| A comparative risk assessment of genetically engineered, mutagenic, andconventional wheat production systems. | Transgenic Res | 2005 Dec | 16315092 |
| Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides. | J Agric Food Chem | 2002 Jun 5 | 12033799 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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 ]
- 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 ]