4906. Imazaquin

Nomenclature

CAS number: 81335-37-7
2-[4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid; 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid; AC-252214.
C17H17N3O3; mol wt 311.34.
C 65.58%, H 5.50%, N 13.50%, O 15.42%.

Description and references

Pre- and post-emergence imidazolinone herbicide especially for use in soybean crops. Prepn: M. Los, EP 41623 (1981 to Am. Cyanamid), C.A. 96, 199687q (1982). Alternate prepn: D. R. Maulding, R. F. Doehner, Jr., US 4459408 (1984 to Am. Cyanamid). Inhibition of branched-chain amino acid biosynthesis: D. L. Shaner et al., Plant Physiol. 76, 545 (1984). Metabolism by plants: D. L. Shaner, P. A. Robson, Weed Sci. 33, 469 (1985). Persistence in soil: G. Basham et al., ibid. 35, 576 (1987). Herbicidal activity: M. W. Beale et al., Proc. Annu. Meet. Northeast. Weed Sci. Soc. 38, 36 (1984); W. F. Congleton et al., Weed Technol. 1, 186 (1987).

Chemical structure

Properties

Crystals from hexane + ethyl acetate, mp 219-222° (dec). Slightly sol in some organic solvents. Soly in water at 25°: 60-120 ppm. LD50 orally in rats: 5000 mg/kg; LC50 (96 hr) in rainbow trout: 100 mg/l (Congleton).

Derivative

Ammonium salt.

Nomenclature

Scepter (BASF).
C17H20N4O3; mol wt 328.37.
C 62.18%, H 6.14%, N 17.06%, O 14.62%.

Properties

Sol in water.

Use

Herbicide.