Imazaquin

HCID 54739CAS 81335-37-7
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)C1(C)N=C(c2nc3ccccc3cc2C(=O)O)NC1=O
InChIKey
CABMTIJINOIHOD-UHFFFAOYSA-N
Molecular formula
C17H17N3O3
Average molar mass
311.33 g/mol
Monoisotopic mass
311.1269914

Overview

2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid is a quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2. It is an imidazolone, a monocarboxylic acid and a quinolinemonocarboxylic acid.

Names & identifiers

Preferred name
Imazaquin
IUPAC
2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)quinoline-3-carboxylic acid
English name
Imazaquin acid
Molecular formula
C17H17N3O3
Molecular weight
311.34

Names & synonyms

IMAZAQUIN81335-37-7Scepter HerbicideImazaquineScepterDTXSID3024152AC 2522148LZY7C31XA2-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid3-Quinolinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-2-(4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-3-quinolinecarboxylic acidIMAGE (PESTICIDE)
Show more names
Imageac252214CL 252214ac252,214SCEPTER(R)Brn 5450078imazaquin acid
2-(4-isopropyl-4-methyl-5-oxo-1H-imidazol-2-yl)quinoline-3-carboxylic acidCHEBI:5869DTXCID9041522-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)quinoline-3-carboxylic acid2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl]-3-quinolinecarboxylic acid3-Quinolinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-RefChem:923327617-220-3

Database identifiers

CAS
81335-37-7
PubChem CID
54739
DTXSID
DTXSID3024152
ChEMBL
CHEMBL1447880
ChEBI
CHEBI:147361
UNII
8LZY7C31XA
EC Number
617-220-3
Nikkaji
J364.773K

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
91.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
23

Experimental & physicochemical properties

Pesticides · 6 items

Pesticide -> EPA IRIS

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Imidazolinone

Herbicides, Plant growth regulators

Pesticide (Imazaquin) -> USDA PDB

OdorSlightly pungent
Color/Form · 3 items

Colorless solid

Tan solid

Crystals from hexane + ethyl acetate

Solubility · 3 items

Sol in water /Imazaquin ammonium salt/

Slightly soluble in some organic solvents.

Sol in water @ 25 °C: 60-120 ppm

Melting Point219-222 °C (decomposition)
Vapor Pressure<0.013 mPa @ 60 °C

Physicochemical properties

Melting point
219 · 219-224°C
Boiling point
451.38 °C · 451.38°C (rough estimate)
Density
1.142 · 1.1420 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
0 · 0-6°C
pka
3.1 · 3.10±0.30(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H312 (22.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]

P273, P280, P302+P352, P317, P321, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 190 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Commission Regulation (EC) No 1490/2002

2008/69, 2008/69, Reg. (EU) 2022/801, Reg. (EU) No 1100/2011, Reg. (EU) No 1100/2011, Reg. (EU) No 540/2011, Reg. (EU) No 540/2011

Hazards Summary · 1 item

Weight loss, mild anemia, and skeletal muscle myopathy observed in chronic study of dogs; No developmental toxicity observed in rats or rabbits; No adverse effects in reproduction during multi-generational study of rats; No evidence of carcinogenicity, mutagenicity, or neurotoxicity; [Reference #1] Not irritating to rabbit skin or eyes; Not sensitizing to guinea pig skin; In 1-year feeding study of dogs at the highest tested dose (5,000 ppm), caused mild anemia, significantly elevated liver enzymes, and striated muscle myopathy with corresponding increase in blood CPK levels; Decreased body weight was the only treatment related effect in two year feeding studies of rats and mice; Increase in frequency and severity of pelvic calcification of the kidneys observed in high-dose multi-generational rat study; No evidence of mutagenicity, carcinogenicity, reproductive toxicity, or developmental toxicity; [EFSA]

Hazard Classes and CategoriesAcute Tox. 4 (22.1%)

Safety & protection

Preventive MeasuresAvoid contact with skin, eyes, and clothing. Wash thoroughly with soap and water after handling.

Toxicology

Target OrgansHematologic
Ecotoxicity Values · 4 items

LC50 Ictaluras punctatus (Channel catfish) 320 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Lepomis macrochirus (Bluegill) 410 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Salmo gairdneri (Rainbow trout) 280 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Daphnia 280 mg/l/48 hr /Conditions of bioassay not specified/

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
EPA IRIS Information · 3 items

Imazaquin

Hematologic

2.5 x 10 ^-1 mg/kg-day

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity ExcerptsIn 2 yr feeding trials, no effect level for rats was 5000 mg/kg.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
rtecs
VB2009800
Toxicity
LD50 orally in rats: 5000 mg/kg; LC50 (96 hr) in rainbow trout: 100 mg/l (Congleton)
risk_code
21
Signal word
Warning

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and ExcretionFollowing oral administration, almost all was excreted in the urine as the unchanged compound within 2 days. No accumulation in blood or tissues.

Uses & manufacturing

Uses · 6 items

Used as pre and post-emergence herbicide for soybeans, ornamentals, and turf; [Reference #1] Used in the EU in combination with chlormequat chloride (CAS# 999-81-5) as plant growth regulator for winter wheat and winter barley; [EFSA]

Farming (Pesticides) [Category: Industry]

/Controls/ dicotyledonous and graminaceous weeds and sedges, controlling weeds in soyabeans at 70-250 g ai/hectare, and shows promise in cowpeas and tobacco.

Control of many broad leaved weeds in soya beans. Also controls or reduces competition from grasses and sedges. Applied either pre- or post-emergence.

Herbicide

This is a man-made compound that is used as a pesticide.

Formulations/PreparationsLiquid concentrate
Use ClassificationHerbicides, Plant growth regulators
General Manufacturing InformationPre- and post-emergence imidazolinone herbicide.

Applications

UsesAgricultural chemical.

Upstream & downstream products

Suppliers36 total

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
上海毕楷科技有限公司18516304666
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid is a quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2. It is a quinolinemonocarboxylic acid, an imidazolone and a monocarboxylic acid.

Related reactions

4 records
New reaction record

Linked notes

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Imazaquin (HCID 54739)｜Huagongshe