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Imazaquin acid

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Imazaquin acid Basic information

Product Name:
Imazaquin acid
Synonyms:
  • IMAZAQUIN
  • imazaquin acid
  • 2-(4-ISOPROPYL-4-METHYL-5-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-QUINOLINE-3-CARBOXYLIC ACID
  • 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid
  • (+/-)-2-[4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL]-3-QUINOLINECARBOXYLIC ACID
  • SCEPTER
  • SCEPTER(R)
  • imazaquin (bsi,ansi,draft e-iso)
CAS:
81335-37-7
MF:
C17H17N3O3
MW:
311.34
Product Categories:
  • Alphabetic
  • Analytical Standards
  • Herbicides
  • Imidazolinone
  • IPesticides&Metabolites
  • Alpha sort
  • H-MAnalytical Standards
  • Pesticides&Metabolites
Mol File:
81335-37-7.mol
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Imazaquin acid Chemical Properties

Melting point:
219-224°C
Boiling point:
451.38°C (rough estimate)
Density 
1.1420 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
0-6°C
pka
3.10±0.30(Predicted)
form 
neat
BRN 
5450078
CAS DataBase Reference
81335-37-7(CAS DataBase Reference)
EPA Substance Registry System
Imazaquin (81335-37-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
21
Safety Statements 
36
WGK Germany 
2
RTECS 
VB2009800
Hazardous Substances Data
81335-37-7(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 5000 mg/kg; LC50 (96 hr) in rainbow trout: 100 mg/l (Congleton)
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Imazaquin acid Usage And Synthesis

Uses

Agricultural chemical.

Hazard

Moderately toxic by ingestion and skin contact. Low toxicity by inhalation.

Pharmacology

Plant Metabolism. The selectivity of imazaquin is due to differential rates and routes of metabolism in tolerant crops versus susceptible weeds (3). The primary metabolite in soybeans is a pyrroloquinoline acetamide (41, Fig. 18), which is immobile in the plant and is not an inhibitor of acetolactate synthase. This metabolite is further broken down to eventually yield a dicarboxylic acid.
Animal Metabolism. Metabolism studies in the rat showed that they rapidly excreted unchanged imazaquin in the urine (5). There was no accumulation of imazaquin or any of its derivatives in the liver, kidney, muscle, fat, or blood. There was no detectable residue in the liver, kidney, muscle, or fat of lactating goats and laying hens, which were fed imazaquin for 7 consecutive days (5).

Metabolism

Imazaquin kills plants by inhibiting acetolactate synthase (ALS) (I50 = 1 μM), which is the first common enzyme in the biosynthesis of the branched chain amino acids, valine, leucine, and isoleucine. Imazaquin is rapidly absorbed through the roots of plants. Once it enters the plant, imazaquin rapidly translocates to the growing points and growth ceases within 1 day after herbicide application followed by chlorosis and then necrosis of the growing points. Total plant death will occur within 2 to 3 weeks after treatment.

Toxicity evaluation

Imazaquin has shown no mutagenic or genotoxic activity in the Ames assay, mammalian cell gene mutation assay, in vitro chromosome aberration assay, in vitro unscheduled DNA synthesis (URS) assay, or the in vivo dominant lethal assay in male rats. This herbicide also has a low potential for bioaccumulation in fish.

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