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 |
---|---|---|---|
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 |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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 GMT 2023
by
admin
on
Sat Dec 16 09:04:21 GMT 2023
|
Record UNII |
787MX0M5A6
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |