Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H15N3O3 |
Molecular Weight | 261.2765 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C1(C)NC(=NC1=O)C2=NC=CC=C2C(O)=O
InChI
InChIKey=CLQMBPJKHLGMQK-UHFFFAOYSA-N
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)
Molecular Formula | C13H15N3O3 |
Molecular Weight | 261.2765 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Imazapyr is the International Organization for Standardization–approved name of 2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]nicotinic acid (International Union of Pure and Applied Chemistry), with Chemical Abstracts Service No. 81334-34-1. Imazapyr is a herbicide used for the control of grasses and broadleaf weeds in a variety of crops, including major uses in soya bean, sunflower, rice, maize, sugar cane, rape, wheat and non-crop areas such as vegetation management and forestry and minor uses in tobacco and oil palm. Imazapyr is absorbed quickly through plant tissue and can be taken up by roots. It is translocated in the xylem and phloem to the meristematic tissues. Imazapyr kills weeds by inhibiting the activity of the plant-specific enzyme acetohydroxyacid synthase, which catalyses the production of three branched-chain amino acids (valine, leucine and isoleucine) required for protein synthesis and cell growth. The rate of plant death is usually slow (several weeks) and is likely related to the amount of stored amino acids available to the plant. Only plants have acetohydroxyacid synthase and therefore, imazapyr is of low toxicity to animals (including fish and insects).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26896896
Curator's Comment: Imazapyr and imazapic (Kifix®) is CNS active in silver catfish Rhamdia quelen. No human data available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2366574 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16665267 |
0.9 µM [Ki] | ||
Target ID: CHEMBL4263 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25035913 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Role of ferrihydrite in adsorption of three imidazolinone herbicides. | 2001 Mar |
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Transformation of carrots with mutant acetolactate synthase for Orobanche (broomrape) control. | 2002 Dec |
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Evolution of herbicide resistance in weeds: initial frequency of target site-based resistance to acetolactate synthase-inhibiting herbicides in Lolium rigidum. | 2002 Jan |
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Adsorption of imidazolinone herbicides on smectite-humic acid and smectite-ferrihydrite associations. | 2002 Jan 16 |
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Crystal structure of yeast acetohydroxyacid synthase: a target for herbicidal inhibitors. | 2002 Mar 22 |
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Rapid, noninvasive screening for perturbations of metabolism and plant growth using chlorophyll fluorescence imaging. | 2003 Jun |
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Acetohydroxyacid synthase from Mycobacterium avium and its inhibition by sulfonylureas and imidazolinones. | 2003 Jun 26 |
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Herbicide resistance in Aster squamatus conferred by a less sensitive form of acetolactate synthase. | 2003 Nov |
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Cross-resistance pattern and alternative herbicides for Cyperus difformis resistant to sulfonylurea herbicides in Korea. | 2004 Jan |
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Biodegradation of imazapyr in typical soils in Zhejiang Province, China. | 2005 |
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Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop. | 2005 |
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Off-target herbicide deposition associated with treating individual trees. | 2005 Aug |
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Saltcedar control and water salvage on the Pecos river, Texas, 1999-2003. | 2005 Jun |
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Imidazolinone-tolerant crops: history, current status and future. | 2005 Mar |
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High-performance liquid chromatographic separation of imidazolinone herbicide enantiomers and their methyl derivatives on polysaccharide-coated chiral stationary phases. | 2006 Jun 9 |
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Molecular characterization of true and ectopic gene targeting events at the acetolactate synthase gene in Arabidopsis. | 2006 Mar |
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Photochemical degradation of imazamox in aqueous solution: influence of metal ions and anionic species on the ultraviolet photolysis. | 2006 May 17 |
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Modelling the leaching of imazapyr in a railway embankment. | 2006 Oct |
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Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography. | 2007 Mar |
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High-efficiency transformation by biolistics of soybean, common bean and cotton transgenic plants. | 2008 |
|
Application of saturation transfer double difference NMR to elucidate the mechanistic interactions of pesticides with humic acid. | 2008 Feb 15 |
|
Biolistic-mediated genetic transformation of cowpea (Vigna unguiculata) and stable Mendelian inheritance of transgenes. | 2008 Sep |
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The ER luminal binding protein (BiP) mediates an increase in drought tolerance in soybean and delays drought-induced leaf senescence in soybean and tobacco. | 2009 |
|
Improved extraction and clean-up of imidazolinone herbicides from soil solutions using different solid-phase sorbents. | 2009 Jun 26 |
|
Crops with target-site herbicide resistance for Orobanche and Striga control. | 2009 May |
|
Isolation, characterization of a strain capable of degrading imazethapyr and its use in degradation of the herbicide in soil. | 2009 Oct |
|
Genetic load and transgenic mitigating genes in transgenic Brassica rapa (field mustard) x Brassica napus (oilseed rape) hybrid populations. | 2009 Oct 31 |
|
Soil-less bioassays for early screening for resistance to imazapyr in sunflower (Helianthus annuus L.). | 2009 Sep |
|
Potato (Solanum tuberosum) greenhouse tuber production as an assay for asexual reproduction effects from herbicides. | 2010 Jan |
|
A composite transcriptional signature differentiates responses towards closely related herbicides in Arabidopsis thaliana and Brassica napus. | 2010 Mar |
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Faster degradation of herbicidally-active enantiomer of imidazolinones in soils. | 2010 May |
|
Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN)nicotinato-κN]manganese(II). | 2010 Nov 27 |
|
AHAS herbicide resistance endowing mutations: effect on AHAS functionality and plant growth. | 2010 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10078164
The toxic syndrome that results from a large quantity (> 100 mL) of Arsenal herbicide (Imazapyr 23.1%, Cyanamid Taiwan Corporation, Taipei) ingestion consists of hypotension, pulmonary dysfunction, oral mucosal and gastrointestinal irritation, and transient liver and renal dysfunction.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16665267
Acetohydroxyacid synthase activities in crude extracts of excised maize leaves and suspension cultured cells were reduced 85 and 58%, respectively, by incubation of the tissue with 100 micromolar (excised leaves) and 5 micromolar (suspension cultures) of the imidazolinone imazapyr prior to enzyme extraction, suggesting that the inhibitor binds tightly to the enzyme in vivo.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:04:21 UTC 2023
by
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on
Sat Dec 16 09:04:21 UTC 2023
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Record UNII |
787MX0M5A6
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
128821
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81334-34-1
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m6216
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DTXSID8034665
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imazapyr
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6676
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787MX0M5A6
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Imazapyr
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54738
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