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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=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)

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
Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling.
2001 Mar
Evolution of herbicide resistance in weeds: initial frequency of target site-based resistance to acetolactate synthase-inhibiting herbicides in Lolium rigidum.
2002 Jan
Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides.
2002 Jun 5
Effects of the herbicide imazapyr on benthic macroinvertebrates in a logged pond cypress dome.
2003 Apr
Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop.
2005
Poor competitive fitness of transgenically mitigated tobacco in competition with the wild type in a replacement series.
2005 Oct
Test of APEX for nine forested watersheds in East Texas.
2007 Jul-Aug
Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography.
2007 Mar
Utilization and degradation of imazaquin by a naturally occurring isolate of Arthrobacter crystallopoietes.
2007 May
CSR1, the sole target of imidazolinone herbicide in Arabidopsis thaliana.
2007 Sep
Application of saturation transfer double difference NMR to elucidate the mechanistic interactions of pesticides with humic acid.
2008 Feb 15
Characterizing and designing polycation-clay nanocomposites as a basis for imazapyr controlled release formulations.
2008 Mar 1
Dissipation of four forest-use herbicides at high latitudes.
2008 Oct
Isolation, characterization of a strain capable of degrading imazethapyr and its use in degradation of the herbicide in soil.
2009 Oct
Potato (Solanum tuberosum) greenhouse tuber production as an assay for asexual reproduction effects from herbicides.
2010 Jan
Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinato]cobalt(II).
2010 Nov 13
Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN)nicotinato-κN]manganese(II).
2010 Nov 27
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011 Mar 28
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
by admin
on Sat Dec 16 09:04:21 GMT 2023
Edited
by admin
on Sat Dec 16 09:04:21 GMT 2023
Record UNII
787MX0M5A6
Record Status Validated (UNII)
Record Version
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Name Type Language
IMAZAPYR
HSDB   ISO   MI  
Common 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
ARSENAL 250A
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128821
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
Code System Code Type Description
CAS
81334-34-1
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
MERCK INDEX
m6216
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID8034665
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
ALANWOOD
imazapyr
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
HSDB
6676
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
FDA UNII
787MX0M5A6
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
WIKIPEDIA
Imazapyr
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY
PUBCHEM
54738
Created by admin on Sat Dec 16 09:04:21 GMT 2023 , Edited by admin on Sat Dec 16 09:04:21 GMT 2023
PRIMARY