Imidazolone

4-Imidazolones are advanced glycation endproducts (AGEs), a class of modified proteins that are biomarkers for diabetes. In this drawing the imidazolone is the C3N2 ring in red and black.[1]

Imidazolinones or imidazolones are a family of heterocyclic compounds, the parents of which have the formula C3H4N2O, where the two nitrogen atoms are nonadjacent. Two isomers are possible, depending on the location of the carbonyl (CO) group. A common route to imidazol-2-ones involves condensation of ureas and acyloins.[2] Some are of interest in the pharmaceuticals.[3] 4-Imidazolones arise from the condensation of amidines with 1,2-dicarbonyls such as glyoxal.[1]

Imidazolinone herbicides work by inhitibing acetolactate synthase and belong to the HRAC class of Group B (Australian, Global), Group 2 (numeric). These herbicides include imazapic, imazamethabenz-methyl, imazamox, imazapyr, imazaquin and imazethapyr.[4]

References

  1. 1 2 Bellier, Justine; Nokin, Marie-Julie; Lardé, Eva; Karoyan, Philippe; Peulen, Olivier; Castronovo, Vincent; Bellahcène, Akeila (2019). "Methylglyoxal, a Potent Inducer of AGEs, Connects between Diabetes and Cancer". Diabetes Research and Clinical Practice. 148: 200–211. doi:10.1016/j.diabres.2019.01.002. PMID 30664892.
  2. ↑ Corson, B. B.; Freeborn, Emeline (1932). "4,5-Diphenylglyoxalone". Org. Synth. 12: 34. doi:10.15227/orgsyn.012.0034.
  3. ↑ Antonova, Maria M.; Baranov, Vladimir V.; Kravchenko, Angelina N. (2015). "Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones". Chemistry of Heterocyclic Compounds. 51 (5): 395–420. doi:10.1007/s10593-015-1716-3.
  4. ↑ "Classification of Herbicides According to Site of Action". WSSA. Retrieved 16 August 2025.
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