Imazaquin
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Systematic IUPAC name
3-Quinolinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.120.551 |
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PubChem CID
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| Properties | |
| C17H17N3O3 | |
| Molar mass | 311.34 g·mol−1 |
| Appearance | Multiple appearances: colorless solid, tan solid, crystals from hexane and ethyl acetate, slightly pungent odor |
| Density | 1.35 g/cm3 |
| Melting point | 219 to 222 °C (426 to 432 °F; 492 to 495 K) |
| Soluble in water at 25 °C: 60-120 ppm | |
| log P | 1.474±0.662 |
| Vapor pressure | 0.013 mPa @ 60 °C |
| Acidity (pKa) | 3.10±0.30 |
| Hazards | |
| Main hazards | May be harmful if swallowed. Harmful in contact with skin. |
| GHS pictograms |  |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Imazaquin is an imidazolinone herbicide that effectively controls a broad spectrum of weed species. It has the formula C17H17N3O3.
Imazaquin along with imazamethabenz-methyl, imazapyr, imazapic, imazethapyr, and imazamox all comprise the unique class of synthetic compounds termed the imidazolinone herbicides. The chemical structures of these chemicals all closely resemble one another, with the compounds containing an identical imidazolinone ring structure with a carboxylic acid group attached to the backbone. They vary only in the attached ring structure. These six herbicides kill plants by inhibiting acetohydroxy acid synthase (AHAS). AHAS is the first enzyme in the branched-chain amino acid pathway that eventually ends in the synthesis of amino acids leucine, isoleucine, and valine.
The imidazolinone herbicides were first discovered in the 1970s. The first U.S. patent was awarded in 1980 for imazamethabenz-methyl. Imazaquin, imazapyr, imazapic, and imazethpyr followed suit and received patents in 1989. Imazamox, the last of the six, received its U.S. patent in 1994.
The discovery of the imidazolinone herbicides began with the synthesis of the initial lead molecule by an American Cyanamid Medical Division chemist during the 1950s. This initial lead molecule was that of phthalimide. Years later during a random screening, the molecule exhibited herbicidal activity. Although it was not known to researchers at the time, the original phthalimide was actually inhibiting the enzyme AHAS. A derivative of phthalimide showed promise when it exhibited some plant growth-regulant activity. Optimization ensued and the attempt to enable the production of field trial samples led to the formation of a tricyclic compound. The same reaction was performed on the original phthalimide, resulting in a compound that exhibited broad-spectrum herbicidal activity. Further exploration resulted in the formation of the first imidazolinone herbicide.
Imazaquin has a water solubility of 60 mg/L and its half-life in soil is 60 days. It is therefore categorized as a moderately persistent pesticide.
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