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Chemical Compound Review

Cybutrin     N'-cyclopropyl-6- methylsulfanyl-N-tert...

Synonyms: Cybutryne, Irgarol, Irgarol(R), Irgarol 1051, Irgarol 1071, ...
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Disease relevance of C10927

  • The antifouling boosting agent Irgarol 1051 is a strong inhibitor of the photosystem II (PSII) with high efficiency/toxicity towards algae [1].

High impact information on C10927

  • The ability of Irgarol 1051 to compete for the antibody binding sites with 11 horseradish peroxidase enzyme tracers, differing in the chemical structures of the hapten, has been investigated [2].
  • Optimum analytical SPME performance was achieved using the PDMS-DVB 65 microm fiber coating in ECD and FTD systems for Sea Nine 211 and Irgarol 1051, respectively [3].
  • The development of an immunoaffinity chromatography (IAC) procedure for the selective extraction of the anti-fouling agent Irgarol 1051 [2-(tert.-butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine] from seawater is described [4].
  • Recent studies have shown that Irgarol 1051 inhibits coral photosynthesis at environmentally relevant concentrations, consistent with its mode of action as a photosystem II inhibitor [5].
  • Indeed, class-specific biomass for chlorophytes as determined by CHEMTAX and microscopy were correlated (R2=0.53) which demonstrated an increase in both abundance and carbon content following exposures to Irgarol 1051 [6].

Chemical compound and disease context of C10927


Biological context of C10927


Associations of C10927 with other chemical compounds


Gene context of C10927

  • Fv/Fm and growth were strongly affected by Irgarol 1051 exposure, but Hsp70 levels were unaltered following exposure to the herbicide [16].
  • The main pollutants found in the sampled points were diuron and Irgarol 1051 that were detected at concentrations up to 2.19 micrograms l-1 and 0.33 microgram l-1, respectively [17].

Analytical, diagnostic and therapeutic context of C10927


  1. Assessing the effects of Irgarol 1051 on marine phytoplankton populations in Key Largo Harbor, Florida. Zamora-Ley, I.M., Gardinali, P.R., Jochem, F.J. Mar. Pollut. Bull. (2006) [Pubmed]
  2. Influence of the hapten design on the development of a competitive ELISA for the determination of the antifouling agent Irgarol 1051 at trace levels. Ballesteros, B., Barceló, D., Sanchez-Baeza, F., Camps, F., Marco, M.P. Anal. Chem. (1998) [Pubmed]
  3. Analysis of antifouling biocides Irgarol 1051 and Sea Nine 211 in environmental water samples using solid-phase microextraction and gas chromatography. Lambropoulou, D.A., Sakkas, V.A., Albanis, T.A. Journal of chromatography. A. (2002) [Pubmed]
  4. Development and application of immunoaffinity chromatography for the determination of the triazinic biocides in seawater. Carrasco, P.B., Escolà, R., Marco, M.P., Bayona, J.M. Journal of chromatography. A. (2001) [Pubmed]
  5. Preliminary examination of short-term cellular toxicological responses of the coral Madracis mirabilis to acute Irgarol 1051 exposure. Downs, C., Downs, A. Arch. Environ. Contam. Toxicol. (2007) [Pubmed]
  6. The effects of a PSII inhibitor on phytoplankton community structure as assessed by HPLC pigment analyses, microscopy and flow cytometry. Devilla, R.A., Brown, M.T., Donkin, M., Readman, J.W. Aquat. Toxicol. (2005) [Pubmed]
  7. The interactive effects of binary mixtures of three antifouling biocides and three heavy metals against the marine algae Chaetoceros gracilis. Koutsaftis, A., Aoyama, I. Environ. Toxicol. (2006) [Pubmed]
  8. Effects of new antifouling compounds on the development of sea urchin. Kobayashi, N., Okamura, H. Mar. Pollut. Bull. (2002) [Pubmed]
  9. Toxicity of anti-fouling biocides to Parorchis acanthus (Digenea: Philophthalmidae) cercarial encystment. Morley, N.J., Leung, K.M., Morritt, D., Crane, M. Dis. Aquat. Org. (2003) [Pubmed]
  10. Identification and characterization of a new degradation product of Irgarol-1051 in mercuric chloride-catalyzed hydrolysis reaction and in coastal waters. Lam, K.H., Lam, M.H., Lam, P.K., Qian, T., Cai, Z., Yu, H., Cheung, R.Y. Mar. Pollut. Bull. (2004) [Pubmed]
  11. Environmental risk limits for antifouling substances. van Wezel, A.P., van Vlaardingen, P. Aquat. Toxicol. (2004) [Pubmed]
  12. Inhibition of coral photosynthesis by the antifouling herbicide Irgarol 1051. Owen, R., Knap, A., Toaspern, M., Carbery, K. Mar. Pollut. Bull. (2002) [Pubmed]
  13. Survey of four marine antifoulant constituents (copper, zinc, diuron and Irgarol 1051) in two UK estuaries. Comber, S.D., Gardner, M.J., Boxall, A.B. Journal of environmental monitoring : JEM. (2002) [Pubmed]
  14. Degradation of the antifouling compound Irgarol 1051 by manganese peroxidase from the white rot fungus Phanerochaete chrysosporium. Ogawa, N., Okamura, H., Hirai, H., Nishida, T. Chemosphere (2004) [Pubmed]
  15. Immunosensors for pollutants working in organic media. Study of performances of different tracers with luminescent detection. González-Martínez, M.A., Penalva, J., Rodríguez-Urbis, J.C., Brunet, E., Maquieira, A., Puchades, R. Analytical and bioanalytical chemistry. (2006) [Pubmed]
  16. Hsp70 expression in Enteromorpha intestinalis (Chlorophyta) exposed to environmental stressors. Lewis, S., Donkin, M.E., Depledge, M.H. Aquat. Toxicol. (2001) [Pubmed]
  17. Occurrence of antifouling biocides in the Spanish Mediterranean marine environment. Martínez, K., Ferrer, I., Hernando, M.D., Fernández-Alba, A.R., Marcé, R.M., Borrull, F., Barceló, D. Environmental technology. (2001) [Pubmed]
  18. Determination of Irgarol 1051 in Western Mediterranean sediments. Development and application of supercritical fluid extraction-immunoaffinity chromatography procedure. Carrasco, P.B., Díez, S., Jiménez, J., Marco, M.P., Bayona, J.M. Water Res. (2003) [Pubmed]
  19. Generation of antiserum to Irgarol 1051 and development of a sensitive enzyme immunoassay using a new heterologous hapten derivative. Abuknesha, R.A., Griffith, H.M. Analytical and bioanalytical chemistry. (2005) [Pubmed]
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