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imazaquin (Ref: BAS 725H)
** AC 252214 ** CL 252214 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for imazaquin

Description: Used as pre- and post-emergence particularly for the control of grasses and broad-leaved weeds

Example pests controlled: Annual grasses and broad-leaved weeds

Example applications: Soybeans; Ornamentals; Turf

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1986, USA

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium/Ireland
Date inclusion expires 31/12/2018
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule, imazaquin is an isomeric mixture of the R- and S-forms
Chemical formula C17H17N3O3
Canonical SMILES CC(C)C1(C(=O)NC(=N1)C2=NC3=CC=CC=C3C=C2C(=O)O)C
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) CABMTIJINOIHOD-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C17H17N3O3/c1-9(2)17(3)16(23)19-14(20-17)13-11(15(21)22)8-10-6-4-5-7-12(10)18-13/h4-9H,1-3H3,(H,21,22)(H,19,20,23)
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide, Plant growth regulator
Substance group Imidazolinone
Minimum active substance purity 960 g/kg racemic mixture
Known relevant impurities EU dossier - Hydrogen cyanide, Toluene
Substance origin Synthetic
Mode of action Selective, systemic absorbed by roots and foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.
CAS RN 81335-37-7
EC number -
CIPAC number 699
US EPA chemical code 128840
PubChem CID 54739
Molecular mass (g mol-1) 311.33
PIN (Preferred Identification Name) -
IUPAC name 2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]quinoline-3-carboxylic acid
CAS name 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-3-quinolinecarboxylic acid
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) B
Herbicide Resistance Classification (WSSA) 2
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Many recorded cases
Amaranthus hybridus
Amaranthus palmeri
Amaranthus powellii
Physical state Grey fine crystalline solid
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • BASF
  • Standon
  • AgroCare
Example products using this active
  • Meteor
  • Upright
  • Scepter
UK LERAP status None
Formulation and application details Usually supplied as a soluble concentrate that is mixed with water and applied as a spray but also available as dispersible granules.


ENVIRONMENTAL FATE

for imazaquin

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 102000 A5 High
Solubility - In organic solvents at 20oC (mg l-1) 240 A5 - Toluene -
14500 A5 - Dichloromethane -
3690 A5 - Acetone -
1490 A5 - Ethyl acetate -
Melting point (oC) 224 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 250 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 8.13 X 10-02 Calculated -
Log P -1.09 A5 Low
Bulk density (g ml-1)/Specific gravity 0.41 B5 -
Dissociation constant (pKa) at 25oC 3.45 A5 -
Note: Weak acid, Pka(2) 11.03
Vapour pressure at 20oC (mPa) 7.0 X 10-10 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 3.74 X 10-12 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 5.42 Calculated High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 7.08 X 10+00 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) 49.9 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 60 B5 Moderately persistent
DT50 (lab at 20oC) 94.3 A5 Moderately persistent
DT50 (field) 11.0 A5 Non-persistent
DT90 (lab at 20oC) 313.2 A5 -
DT90 (field) 45.3 A5 -
DT50 modelling endpoint - - -
Note EU dossier aerobic lab studies DT50 range 43-223 days, DT90 range 142.7-741.9 days; field studies DT50 range 1.7-31.1 days, DT90 range 5-103 days; Other sources: Lab studies showed slow degradation (B5)
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 13.1 R4 -
Note Published literature RL50 range 4.4-39.8 days, 6 field crops, various matrices, n=8
Aqueous photolysis DT50 (days) at pH 7 Value 0.75 A5 Fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 4 to pH 7, DT50 169 days at pH 9 and 25 degC, 20.6 days at pH 9 and 50 degC
Water-sediment DT50 (days) 475 A5 Stable
Water phase only DT50 (days) 194 A5 Stable

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 0.31 A5 Mobile
Kfoc 17.96
1/n 1.03
Notes and range EU dossier kf range 0.114-0.316, Kfoc range 8.9-37 mL/g, 1/n range 0.993-1.11, Soils=5
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
2-(1-carbamoyl-1,2-dimethyl-propylcarbamoyl)-quinoline-3-carboxylic acid (Ref: CL-266066) Soil   0.054   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
2,3-quinoline di-carboxylic acid-2-methylester - Plant - -
2,3-quinoline di-carboxylic acid-3-methylester - Plant - -
2,3-quinoline di-carboxylic acid
(Ref: CL 263875)
- Plant; Soil; Groundwater - -
3-quinoline carboxylic acid
(Ref: CL 75947)
- Soil - -


ECOTOXICOLOGY

for imazaquin

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 0.39 Q2 Estimated Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 474 B5 Rat Moderate
(ppm diet) > 10000 -
Birds - Acute LD50 (mg kg-1) > 2150 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) > 1166 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) > 100 A5 Oncorhynchus mykiss Low
Fish - Chronic 21 day NOEC (mg l-1) 51.2 A5 Oncorhynchus mykiss Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 100 A5 Daphnia magna Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 100 A5 Daphnia magna Low
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 228 A5 Chironomus riparius, emergence Low
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.031 A5 Lemna gibba Moderate
Non-target plants > 1.7 A5 Allium cepa
Seedling emergence, ER50
as L product/ha (Meteor)
-
> 1.8 A5 Beta vulgaris
Vegetative vigour, ER50
as L product/ha (Meteor)
-
Algae - Acute 72 hour EC50, growth (mg l-1) 21.5 A5 Pseudokirchneriella subcaptitata Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 6.5 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 23.5 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) > 0.028 A5 Eisenia foetida High
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 4.0 >
A5 Aphidius rhopalosiphi
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 4.0 >
A5 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.0133 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for imazaquin

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rabbit -
Mammals - Inhalation LC50 (mg l-1) > 5.7 A5 Rat, 4 hr (whole body) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.25 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) Not allocated A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.25 A5 Dog, SF=100 -
Dermal penetration studies (%) 100 A3 default -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Negligible risks to bystanders
Occupational No unacceptable risks identified for operators or other farm workers
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Harmful if ingested

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Health: H302, H317, H319
Environment: H401
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22
N - Dangerous for the environment: R53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for imazaquin

Language Name
English imazaquin
French imazaquine
German Imazaquin
Danish imazaquin
Italian imazaquin
Spanish imazaquin
Greek -
Slovenian imazakvin
Polish imazachin
Swedish -
Hungarian imazaquin
Dutch -

Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk