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Chemical Compound Review

Alochlor     2-chloro-N-(2,6- diethylphenyl)-N...

Synonyms: Lasagrin, Pillarzo, alachlor, Alachlore, Chimiclor, ...
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Disease relevance of Methachlor

  • Moreover, expression of one of these clones in E. coli resulted in a GST activity as measured with both CDNB and alachlor, proving that at least one of the clones encodes an active GST III species [1].
  • The risks of leukemia (rate ratio = 2.83, 95% confidence interval: 0.74, 10.9) and multiple myeloma (rate ratio = 5.66, 95% confidence interval: 0.70, 45.7) were increased among applicators in the highest alachlor exposure category [2].
  • When pre-incubated with an olfactory mucosal S9 activation system, alachlor induced a weak, dose-dependent mutagenic response at 500-1250 micrograms/plate, with toxicity at higher doses [3].
  • Morphological and phylogenetic analysis enabled the assignment of the alachlor-degrading strains to the genus Streptomyces [4].
  • Isolation and characterization of alachlor-degrading actinomycetes from soil [4].

High impact information on Methachlor


Chemical compound and disease context of Methachlor


Biological context of Methachlor

  • Dietary exposure to alachlor depletes olfactory mucosa antioxidants, which may contribute to DNA damage and tissue-specific tumor formation [13].
  • Subsequent studies have shown that specific metabolic activation of alachlor is required for nasal tumor formation, and that non-genotoxic, threshold-sensitive processes produce all three tumors [14].
  • The effect of vehicle dilution on the percutaneous absorption of alachlor, 2-chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide, through excised human skin was determined using flowthrough design glass penetration cells and 14C radiotracer methodology [15].
  • Influence of surface composition on the kinetics of alachlor reduction by iron pyrite [16].
  • Cytogenetic effects of alachlor and mancozeb [17].

Anatomical context of Methachlor

  • These herbicides are carcinogenic in rats: acetochlor and alachlor cause tumors in the nasal turbinates, butachlor causes stomach tumors, and metolachlor causes liver tumors [18].
  • We show here that alachlor rapidly accumulates as GS-conjugates in the plant vacuole and that the first step of its degradation, the formation of the respective gamma-glutamylcysteinyl-S-conjugate, is catalyzed by a vacuolar carboxypeptidase [19].
  • Missing Link?: Alachlor and Semen Quality [20].
  • In addition, ESA did not elicit the characteristic preneoplastic changes observed in the development of alachlor-induced nasal, stomach, and thyroid tumors [14].
  • Both isolated and whole blood human lymphocytes were exposed to alachlor using several protocols [21].

Associations of Methachlor with other chemical compounds


Gene context of Methachlor


Analytical, diagnostic and therapeutic context of Methachlor


  1. Cloning and expression of a cDNA encoding a maize glutathione-S-transferase in E. coli. Moore, R.E., Davies, M.S., O'Connell, K.M., Harding, E.I., Wiegand, R.C., Tiemeier, D.C. Nucleic Acids Res. (1986) [Pubmed]
  2. Cancer incidence among pesticide applicators exposed to alachlor in the Agricultural Health Study. Lee, W.J., Hoppin, J.A., Blair, A., Lubin, J.H., Dosemeci, M., Sandler, D.P., Alavanja, M.C. Am. J. Epidemiol. (2004) [Pubmed]
  3. Evidence for site-specific bioactivation of alachlor in the olfactory mucosa of the Long-Evans rat. Wetmore, B.A., Mitchell, A.D., Meyer, S.A., Genter, M.B. Toxicol. Sci. (1999) [Pubmed]
  4. Isolation and characterization of alachlor-degrading actinomycetes from soil. Sette, L.D., de Oliveira, V.M., Manfio, G.P. Antonie Van Leeuwenhoek (2005) [Pubmed]
  5. Herbicide safener-binding protein of maize. Purification, cloning, and expression of an encoding cDNA. Scott-Craig, J.S., Casida, J.E., Poduje, L., Walton, J.D. Plant Physiol. (1998) [Pubmed]
  6. Simultaneous quantification of acetanilide herbicides and their oxanilic and sulfonic acid metabolites in natural waters. Heberle, S.A., Aga, D.S., Hany, R., Müller, S.R. Anal. Chem. (2000) [Pubmed]
  7. Characterization of covalent protein conjugates using solid-state 13C NMR spectroscopy. Garbow, J.R., Fujiwara, H., Sharp, C.R., Logusch, E.W. Biochemistry (1991) [Pubmed]
  8. Kinetic analysis of maize glutathione S-transferase I catalysing the detoxification from chloroacetanilide herbicides. Labrou, N.E., Karavangeli, M., Tsaftaris, A., Clonis, Y.D. Planta (2005) [Pubmed]
  9. Acetochlor-induced rat nasal tumors: further studies on the mode of action and relevance to humans. Green, T., Lee, R., Moore, R.B., Ashby, J., Willis, G.A., Lund, V.J., Clapp, M.J. Regulatory toxicology and pharmacology : RTP. (2000) [Pubmed]
  10. 4-Hydroxybenzoate uptake in Klebsiella planticola strain DSZ1 is driven by DeltapH. Allende, J.L., Gibello, A., Fortún, A., Sánchez, M., Martín, M. Curr. Microbiol. (2002) [Pubmed]
  11. Cytotoxicity of chloroacetanilide herbicide alachlor in HepG2 cells independent of CYP3A4 and CYP3A7. Miranda, S.R., Meyer, S.A. Food Chem. Toxicol. (2007) [Pubmed]
  12. Toxicity assessment of atrazine, alachlor, and carbofuran and their respective environmental metabolites using Microtox. Kross, B.C., Vergara, A., Raue, L.E. Journal of toxicology and environmental health. (1992) [Pubmed]
  13. Antioxidant perturbations in the olfactory mucosa of alachlor-treated rats. Burman, D.M., Shertzer, H.G., Senft, A.P., Dalton, T.P., Genter, M.B. Biochem. Pharmacol. (2003) [Pubmed]
  14. Ethane sulfonate metabolite of alachlor: assessment of oncogenic potential based on metabolic and mechanistic considerations. Heydens, W.F., Wilson, A.G., Kraus, L.J., Hopkins, W.E., Hotz, K.J. Toxicol. Sci. (2000) [Pubmed]
  15. In vitro percutaneous absorption and stratum corneum binding of alachlor: effect of formulation dilution with water. Bucks, D.A., Wester, R.C., Mobayen, M.M., Yang, D., Maibach, H.I., Coleman, D.L. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  16. Influence of surface composition on the kinetics of alachlor reduction by iron pyrite. Carlson, D.L., McGuire, M.M., Roberts, A.L., Fairbrother, D.H. Environ. Sci. Technol. (2003) [Pubmed]
  17. Cytogenetic effects of alachlor and mancozeb. Georgian, L., Moraru, I., Draghicescu, T., Dinu, I., Ghizelea, G. Mutat. Res. (1983) [Pubmed]
  18. Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes. Coleman, S., Linderman, R., Hodgson, E., Rose, R.L. Environ. Health Perspect. (2000) [Pubmed]
  19. Degradation of glutathione S-conjugates by a carboxypeptidase in the plant vacuole. Wolf, A.E., Dietz, K.J., Schröder, P. FEBS Lett. (1996) [Pubmed]
  20. Missing Link?: Alachlor and Semen Quality. Gustafson, D. Environ. Health Perspect. (2005) [Pubmed]
  21. An evaluation of the feasibility of using cytogenetic damage as a biomarker for alachlor exposure. Kligerman, A.D., Erexson, G.L. Mutat. Res. (1999) [Pubmed]
  22. Semen quality in relation to biomarkers of pesticide exposure. Swan, S.H., Kruse, R.L., Liu, F., Barr, D.B., Drobnis, E.Z., Redmon, J.B., Wang, C., Brazil, C., Overstreet, J.W. Environ. Health Perspect. (2003) [Pubmed]
  23. Biodegradation of the acetanilide herbicides alachlor, metolachlor, and propachlor. Stamper, D.M., Tuovinen, O.H. Crit. Rev. Microbiol. (1998) [Pubmed]
  24. Genotoxicity of humic acid in cultured human lymphocytes and its interaction with the herbicides alachlor and maleic hydrazide. Ribas, G., Carbonell, E., Creus, A., Xamena, N., Marcos, R. Environ. Mol. Mutagen. (1997) [Pubmed]
  25. Effect of alachlor on hepatic cytochrome P450 enzymes in rats. Hanioka, N., Watanabe, K., Yoda, R., Ando, M. Drug and chemical toxicology. (2002) [Pubmed]
  26. Effect of endocrine disrupting chemicals on lipopolysaccharide-induced tumor necrosis factor-alpha and nitric oxide production by mouse macrophages. Hong, C.C., Shimomura-Shimizu, M., Muroi, M., Tanamoto, K. Biol. Pharm. Bull. (2004) [Pubmed]
  27. Chemopreventive properties of trans-resveratrol against the cytotoxicity of chloroacetanilide herbicides in vitro. Kocsis, Z., Marcsek, Z.L., Jakab, M.G., Szende, B., Tompa, A. International journal of hygiene and environmental health. (2005) [Pubmed]
  28. Characterization of photodegradation products of alachlor in water by on-line solid-phase extraction liquid chromatography combined with tandem mass spectrometry and orthogonal-acceleration time-of-flight mass spectrometry. Hogenboom, A.C., Niessen, W.M., Brinkman, U.A. Rapid Commun. Mass Spectrom. (2000) [Pubmed]
  29. Rapid trace analysis of alachlor in water and vegetable samples. Gabaldón, J.A., Cascales, J.M., Maquieira, A., Puchades, R. Journal of chromatography. A. (2002) [Pubmed]
  30. Induction of micronuclei in Vicia faba root tips treated in different soils with the herbicide alachlor. De Marco, A., Boccardi, P., De Simone, C., Piccolo, A., Raglione, M., Testa, A., Trinca, S. Mutat. Res. (1990) [Pubmed]
  31. Metabolism of alachlor by rat and mouse liver and nasal turbinate tissues. Feng, P.C., Wilson, A.G., McClanahan, R.H., Patanella, J.E., Wratten, S.J. Drug Metab. Dispos. (1990) [Pubmed]
  32. Herbicide-induced DNA damage in human lymphocytes evaluated by the single-cell gel electrophoresis (SCGE) assay. Ribas, G., Frenzilli, G., Barale, R., Marcos, R. Mutat. Res. (1995) [Pubmed]
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