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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
Structure of IMAZAPYR

SMILES

CC(C)C1(C)NC(=NC1=O)C2=C(C=CC=N2)C(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)

HIDE SMILES / InChI

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

Curator's Comment: Imazapyr and imazapic (Kifix®) is CNS active in silver catfish Rhamdia quelen. No human data available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011-03-28
Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN)nicotinato-κN]manganese(II).
2010-11-27
Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinato]cobalt(II).
2010-11-13
AHAS herbicide resistance endowing mutations: effect on AHAS functionality and plant growth.
2010-09
Faster degradation of herbicidally-active enantiomer of imidazolinones in soils.
2010-05
A composite transcriptional signature differentiates responses towards closely related herbicides in Arabidopsis thaliana and Brassica napus.
2010-03
Potato (Solanum tuberosum) greenhouse tuber production as an assay for asexual reproduction effects from herbicides.
2010-01
Genetic load and transgenic mitigating genes in transgenic Brassica rapa (field mustard) x Brassica napus (oilseed rape) hybrid populations.
2009-10-31
Isolation, characterization of a strain capable of degrading imazethapyr and its use in degradation of the herbicide in soil.
2009-10
Soil-less bioassays for early screening for resistance to imazapyr in sunflower (Helianthus annuus L.).
2009-09
Improved extraction and clean-up of imidazolinone herbicides from soil solutions using different solid-phase sorbents.
2009-06-26
Crops with target-site herbicide resistance for Orobanche and Striga control.
2009-05
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
Molecular and biochemical characterization of an induced mutation conferring imidazolinone resistance in sunflower.
2008-12
Mutations of the ALS gene endowing resistance to ALS-inhibiting herbicides in Lolium rigidum populations.
2008-12
Effects of low concentrations of herbicides on full-season, field-grown potatoes.
2008-10-25
Dissipation of four forest-use herbicides at high latitudes.
2008-10
Biolistic-mediated genetic transformation of cowpea (Vigna unguiculata) and stable Mendelian inheritance of transgenes.
2008-09
Mineralization of herbicides imazapyr and imazaquin in aqueous medium by, fenton, photo-fenton and electro-fenton processes.
2008-05
Characterizing and designing polycation-clay nanocomposites as a basis for imazapyr controlled release formulations.
2008-03-01
Application of saturation transfer double difference NMR to elucidate the mechanistic interactions of pesticides with humic acid.
2008-02-15
Abiotic degradation (photodegradation and hydrolysis) of imidazolinone herbicides.
2008-02
Comparative genotoxicity evaluation of imidazolinone herbicides in somatic cells of Drosophila melanogaster.
2008-01
High-efficiency transformation by biolistics of soybean, common bean and cotton transgenic plants.
2008
CSR1, the sole target of imidazolinone herbicide in Arabidopsis thaliana.
2007-09
Test of APEX for nine forested watersheds in East Texas.
2007-05-29
Utilization and degradation of imazaquin by a naturally occurring isolate of Arthrobacter crystallopoietes.
2007-05
Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography.
2007-03
Responses of enantioselective characteristics of imidazolinone herbicides and Chiralcel OJ column to temperature variations.
2006-10-27
Modelling the leaching of imazapyr in a railway embankment.
2006-10
High-performance liquid chromatographic separation of imidazolinone herbicide enantiomers and their methyl derivatives on polysaccharide-coated chiral stationary phases.
2006-06-09
Photochemical degradation of imazamox in aqueous solution: influence of metal ions and anionic species on the ultraviolet photolysis.
2006-05-17
Influence of metal salts on the photodegradation of imazapyr, an imidazolinone pesticide.
2006-05
Effectiveness of management interventions to control invasion by Rhododendron ponticum.
2006-04
Molecular characterization of true and ectopic gene targeting events at the acetolactate synthase gene in Arabidopsis.
2006-03
Poor competitive fitness of transgenically mitigated tobacco in competition with the wild type in a replacement series.
2005-10
Off-target herbicide deposition associated with treating individual trees.
2005-08
Saltcedar control and water salvage on the Pecos river, Texas, 1999-2003.
2005-06
Imidazolinone-tolerant crops: history, current status and future.
2005-03
Biodegradation of imazapyr by free cells of Pseudomonas fluorescene biotype II and Bacillus cereus isolated from soil.
2005-02
Biodegradation of imazapyr in typical soils in Zhejiang Province, China.
2005
Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop.
2005
[Human health and pesticides used in the spraying of illicit crops: an issue of science or politics?].
2004-09-24
A comparative toxicologic and genotoxic study of the herbicide arsenal, its active ingredient imazapyr, and the surfactant nonylphenol ethoxylate.
2004-09
Use of imazapyr against Equisetum arvense on Swedish railway tracks.
2004-06
The fate of imazapyr in a Swedish railway embankment.
2004-06
Cross-resistance pattern and alternative herbicides for Cyperus difformis resistant to sulfonylurea herbicides in Korea.
2004-01
Herbicide resistance in Aster squamatus conferred by a less sensitive form of acetolactate synthase.
2003-11
Sulfonylurea herbicide-resistant Monochoria vaginalis in Korean rice culture.
2003-09
Evaluation of resistance in Amaranthus quitensis Kunth populations to imazethapyr and other imidazolinones.
2003
Patents

Sample Use Guides

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
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
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on Mon Mar 31 22:28:11 GMT 2025
Edited
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Record UNII
787MX0M5A6
Record Status Validated (UNII)
Record Version
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Name Type Language
IMAZAPYR
HSDB   ISO   MI  
Common Name English
ARSENAL 250A
Preferred Name English
IMAZAPYR, (RS)-
Common Name English
3-PYRIDINECARBOXYLIC ACID, 2-(4,5-DIHYDRO-4-METHYL-4-(1- METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL)-
Systematic Name English
IMAZAPYR [HSDB]
Common Name English
CHARPER
Brand Name English
2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)NICOTINIC ACID
Systematic Name English
2-(4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL- 2-YL)-3-PYRIDINECARBOXYLIC ACID
Systematic Name English
IMAZAPYR [ISO]
Common Name English
IMAZAPYR [MI]
Common Name English
IMAZAPYR, (±)-
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128821
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
Code System Code Type Description
CAS
81334-34-1
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
MERCK INDEX
m6216
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID8034665
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
ALANWOOD
imazapyr
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
HSDB
6676
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
FDA UNII
787MX0M5A6
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
WIKIPEDIA
Imazapyr
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY
PUBCHEM
54738
Created by admin on Mon Mar 31 22:28:11 GMT 2025 , Edited by admin on Mon Mar 31 22:28:11 GMT 2025
PRIMARY