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Chemical Compound Review

SureCN9031     1,3-dihydroimidazol-2-one

Synonyms: PubChem18114, SureCN127795, AG-B-76810, ACN-S001187, CHEBI:51022, ...
 
 
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Disease relevance of Shell SD-8591

  • Acetohydroxyacid synthase (EC 4.1.3.18, also known as acetolactate synthase) isoenzyme II from Escherichia coli is inhibited by sulphonylurea and imidazolinone herbicides, although it is much less sensitive than the plant enzyme [1].
 

High impact information on Shell SD-8591

 

Biological context of Shell SD-8591

  • Since the imidazolinone-resistance gene (Imi1) is located on the D genome, it is possible for resistance to be transferred to jointed goatgrass via hybridization and backcrossing [6].
  • Expression of the AHAS gene under the control of the CaMV 35S promoter in transgenic tobacco resulted in selective imidazolinone resistance, confirming that the single base-pair change found near the 3' end of the coding region of this gene is responsible for imidazolinone resistance [7].
  • We report the successful engineering of a mutant acetolactate synthase (ALS) gene into carrot, allowing control of broomrape already in heterozygotes of the first back-crossed generation, by imazapyr, an imidazolinone ALS inhibitor [8].
 

Associations of Shell SD-8591 with other chemical compounds

 

Gene context of Shell SD-8591

  • Risk for mutated AHAS protein in imidazolinone-tolerant wheat most likely would be low, but there are not sufficient effect and exposure data to adequately characterize risk [14].
 

Analytical, diagnostic and therapeutic context of Shell SD-8591

References

  1. Mutagenesis studies on the sensitivity of Escherichia coli acetohydroxyacid synthase II to herbicides and valine. Lee, Y.T., Duggleby, R.G. Biochem. J. (2000) [Pubmed]
  2. A naturally occurring point mutation confers broad range tolerance to herbicides that target acetolactate synthase. Bernasconi, P., Woodworth, A.R., Rosen, B.A., Subramanian, M.V., Siehl, D.L. J. Biol. Chem. (1995) [Pubmed]
  3. Nucleotide sequence of a mutant acetolactate synthase gene from an imidazolinone-resistant Arabidopsis thaliana var. Columbia. Sathasivan, K., Haughn, G.W., Murai, N. Nucleic Acids Res. (1990) [Pubmed]
  4. Rational molecular design and genetic engineering of herbicide resistant crops by structure modeling and site-directed mutagenesis of acetohydroxyacid synthase. Ott, K.H., Kwagh, J.G., Stockton, G.W., Sidorov, V., Kakefuda, G. J. Mol. Biol. (1996) [Pubmed]
  5. Mutagenesis of Escherichia coli acetohydroxyacid synthase isoenzyme II and characterization of three herbicide-insensitive forms. Hill, C.M., Duggleby, R.G. Biochem. J. (1998) [Pubmed]
  6. Introgression of an imidazolinone-resistance gene from winter wheat (Triticum aestivum L.) into jointed goatgrass (Aegilops cylindrica Host). Perez-Jones, A., Mallory-Smith, C.A., Hansen, J.L., Zemetra, R.S. Theor. Appl. Genet. (2006) [Pubmed]
  7. Multiple resistance to sulfonylureas and imidazolinones conferred by an acetohydroxyacid synthase gene with separate mutations for selective resistance. Hattori, J., Rutledge, R., Labbé, H., Brown, D., Sunohara, G., Miki, B. Mol. Gen. Genet. (1992) [Pubmed]
  8. Transformation of carrots with mutant acetolactate synthase for Orobanche (broomrape) control. Aviv, D., Amsellem, Z., Gressel, J. Pest Manag. Sci. (2002) [Pubmed]
  9. Systematic characterization of mutations in yeast acetohydroxyacid synthase. Interpretation of herbicide-resistance data. Duggleby, R.G., Pang, S.S., Yu, H., Guddat, L.W. Eur. J. Biochem. (2003) [Pubmed]
  10. High-performance liquid chromatographic separation of imidazolinone herbicide enantiomers and their methyl derivatives on polysaccharide-coated chiral stationary phases. Lao, W., Gan, J. Journal of chromatography. A. (2006) [Pubmed]
  11. Genomic damage and circulating AGE levels in patients undergoing daily versus standard haemodialysis. Fragedaki, E., Nebel, M., Schupp, N., Sebekova, K., Völkel, W., Klassen, A., Pischetsrieder, M., Frischmann, M., Niwa, T., Vienken, J., Heidland, A., Stopper, H. Nephrol. Dial. Transplant. (2005) [Pubmed]
  12. Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography. Lin, K., Xu, C., Zhou, S., Liu, W., Gan, J. Chirality (2007) [Pubmed]
  13. Occurrence of sulfonylurea, sulfonamide, imidazolinone, and other herbicides in rivers, reservoirs and ground water in the Midwestern United States, 1998. Battaglin, W.A., Furlong, E.T., Burkhardt, M.R., Peter, C.J. Sci. Total Environ. (2000) [Pubmed]
  14. A comparative risk assessment of genetically engineered, mutagenic, and conventional wheat production systems. Peterson, R.K., Shama, L.M. Transgenic Res. (2005) [Pubmed]
  15. Simultaneous determination of imidazolinone herbicides from soil and natural waters using soil column extraction and off-line solid-phase extraction followed by liquid chromatography with UV detection or liquid chromatography/electrospray mass spectroscopy. Laganà, A., Fago, G., Marino, A. Anal. Chem. (1998) [Pubmed]
  16. Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides. Chin, T.E., Wong, R.B., Pont, J.L., Karu, A.E. J. Agric. Food Chem. (2002) [Pubmed]
  17. Capillary electrophoresis determinative and LC-MS confirmatory method for screening selected imidazolinone herbicides from soil. Nejad, H., Safarpour, M.M., Cavalier, T., Picard, G., Souza, M., Krynitsky, A.J., Chiu, S., Miller, P., Stout, S.J. Journal of capillary electrophoresis. (1998) [Pubmed]
 
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