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Chemical Compound Review

Thiamethoxam     nitramide

Synonyms: AC1NUNYK, SureCN22916, KB-61579, AKOS015895937, FT-0643510, ...
 
 
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Disease relevance of nitramide

  • It is proposed that CGA265307, through its effects on nitric oxide synthase, exacerbates the toxicity of CGA330050 in thiamethoxam treated mice [1].
  • Thiamethoxam is a neonicotinoid insecticide that is not a mutagen, but it did cause a significant increase in liver cancer in mice, but not rats, in chronic dietary feeding studies [2].
 

High impact information on nitramide

  • The substrate specificity of AOX was characterized as follows: Neonicotinoids with a tertiary nitrogen (N-methylimidacloprid and thiamethoxam) are poor substrates; nitroguanidines are metabolized faster than nitromethylenes; and clothianidin is the most rapidly reduced [3].
  • Because of stability considerations, a pH partitioning method is used to separate thiamethoxam aminoguanidine and guanidine [4].
  • Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 2: species differences in response [2].
  • Over the duration of a 50-week thiamethoxam dietary feeding study in mice, the earliest change, within one week, is a marked reduction (by up to 40%) in plasma cholesterol [1].
  • Overall, the data suggested that the outstanding insecticidal properties of thiamethoxam may be due to either a different binding site on nicotinic receptors, or receptor isoforms, or specific pharmakokinetic behavior, rather than to exceptional affinity to one of the examined binding sites [5].
 

Chemical compound and disease context of nitramide

 

Biological context of nitramide

 

Anatomical context of nitramide

 

Associations of nitramide with other chemical compounds

 

Gene context of nitramide

 

Analytical, diagnostic and therapeutic context of nitramide

References

  1. Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 1: mode of action studies in the mouse. Green, T., Toghill, A., Lee, R., Waechter, F., Weber, E., Noakes, J. Toxicol. Sci. (2005) [Pubmed]
  2. Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 2: species differences in response. Green, T., Toghill, A., Lee, R., Waechter, F., Weber, E., Peffer, R., Noakes, J., Robinson, M. Toxicol. Sci. (2005) [Pubmed]
  3. Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. Dick, R.A., Kanne, D.B., Casida, J.E. Chem. Res. Toxicol. (2006) [Pubmed]
  4. Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives. Kanne, D.B., Dick, R.A., Tomizawa, M., Casida, J.E. Chem. Res. Toxicol. (2005) [Pubmed]
  5. Characterization of nicotinic acetylcholine receptors from the insects Aphis craccivora, Myzus persicae, and Locusta migratoria by radioligand binding assays: relation to thiamethoxam action. Wiesner, P., Kayser, H. J. Biochem. Mol. Toxicol. (2000) [Pubmed]
  6. Susceptibility of immature stages of Homalodisca coagulata (Hemiptera: Cicadellidae) to selected insecticides. Prabhaker, N., Castle, S.J., Toscano, N.C. J. Econ. Entomol. (2006) [Pubmed]
  7. Susceptibility of pest Nezara viridula (Heteroptera: Pentatomidae) and parasitoid Trichopoda pennipes (Diptera: Tachinidae) to selected insecticides. Tillman, P.G. J. Econ. Entomol. (2006) [Pubmed]
  8. Use of residue profile analysis to identify modes of insecticide activity contributing to control of plum curculio in apples. Wise, J.C., Coombs, A.B., Vandervoort, L.C., Gut, L.J., Hoffmann, E.J., Whalon, M.E. J. Econ. Entomol. (2006) [Pubmed]
  9. Toxicity, persistence, and efficacy of spinosad, chlorfenapyr, and thiamethoxam on eggplant when applied against the eggplant flea beetle (Coleoptera: Chrysomelidae). McLeod, P., Diaz, F.J., Johnson, D.T. J. Econ. Entomol. (2002) [Pubmed]
  10. Relative effects of the insecticide thiamethoxam on the predator Podisus nigrispinus and the tobacco whitefly Bemisia tabaci in nectaried and nectariless cotton. Torres, J.B., Silva-Torres, C.S., Barros, R. Pest Manag. Sci. (2003) [Pubmed]
  11. Hydrolysis of thiamethoxam. Liqing, Z., Guoguang, L., Dezhi, S., Kun, Y. Bulletin of environmental contamination and toxicology. (2006) [Pubmed]
  12. Comparative analysis of neonicotinoid binding to insect membranes: II. An unusual high affinity site for [3H]thiamethoxam in Myzus persicae and Aphis craccivora. Wellmann, H., Gomes, M., Lee, C., Kayser, H. Pest Manag. Sci. (2004) [Pubmed]
  13. Evaluation of thiamethoxam and imidacloprid as seed treatments to control European corn borer and Indianmeal moth (Lepidoptera: Pyralidae) larvae. Yue, B., Wilde, G.E., Arthur, F. J. Econ. Entomol. (2003) [Pubmed]
  14. Sensitive determination of thiamethoxam, imidacloprid and acetamiprid in environmental water samples with solid-phase extraction packed with multiwalled carbon nanotubes prior to high-performance liquid chromatography. Zhou, Q., Ding, Y., Xiao, J. Analytical and bioanalytical chemistry. (2006) [Pubmed]
  15. Simultaneous determination of imidacloprid, thiacloprid, and thiamethoxam in soil and water by high-performance liquid chromatography with diode-array detection. Ying, G.G., Kookana, R.S. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (2004) [Pubmed]
  16. Tunneling and mortality of eastern and Formosan subterranean termites (Isoptera: Rhinotermitidae) in sand treated with thiamethoxam or fipronil. Remmen, L.N., Su, N.Y. J. Econ. Entomol. (2005) [Pubmed]
  17. The discovery of thiamethoxam: a second-generation neonicotinoid. Maienfisch, P., Huerlimann, H., Rindlisbacher, A., Gsell, L., Dettwiler, H., Haettenschwiler, J., Sieger, E., Walti, M. Pest Manag. Sci. (2001) [Pubmed]
  18. Determination of Thiamethoxam residues in honeybees by high performance liquid chromatography with an electrochemical detector and post-column photochemical reactor. Rancan, M., Rossi, S., Sabatini, A.G. Journal of chromatography. A. (2006) [Pubmed]
  19. Development of an enzyme-linked immunosorbent assay for the insecticide thiamethoxam. Kim, H.J., Liu, S., Keum, Y.S., Li, Q.X. J. Agric. Food Chem. (2003) [Pubmed]
  20. Insecticide enhancement with feeding stimulants in corn for western corn rootworm larvae (Coleoptera: Chrysomelidae). Bernklau, E.J., Bjostad, L.B. J. Econ. Entomol. (2005) [Pubmed]
 
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