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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

dicamba     3,6-dichloro-2-methoxy-benzoic acid

Synonyms: Mediben, Banlen, Banvel, Dianat, Mdba, ...
 
 
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Disease relevance of dicamba

  • A three-component dicamba O-demethylase from Pseudomonas maltophilia, strain DI-6: gene isolation, characterization, and heterologous expression [1].
  • Mixtures of the three highly purified recombinant dicamba O-demethylase components overexpressed in Escherichia coli converted dicamba to DCSA with an efficiency similar to that of the native enzyme, suggesting that all of the components required for optimal enzymatic activity have been identified [1].
  • We investigated the developmental toxicity in mice of a common commercial formulation of herbicide containing a mixture of 2,4-dichlorophenoxyacetic acid (2,4-D), mecoprop, dicamba, and inactive ingredients [2].
  • There was no apparent risk for non-Hodgkin lymphoma.ConclusionsAlthough associations between exposure and lung and colon cancer were observed, we did not find clear evidence for an association between dicamba exposure and cancer risk [3].
  • The 16S rRNA analysis results showed that the isolate belongs to the genus of Sphingomonas, close to dioxin and dicamba degraders, and is named Sphingomonas sp. SB5 [4].
 

High impact information on dicamba

 

Chemical compound and disease context of dicamba

 

Biological context of dicamba

  • With this method it was possible to conduct preliminary studies examining the kinetics of dicamba metabolism in P. maltophilia [10].
  • While dicamba did not show clastogenic effects in rodents, DNOC gave significant dose-related increases of structural chromosome aberrations in rat bone marrow cells [11].
  • The genotoxic effects of the herbicide dicamba have been studied by measuring 1) the unwinding rate of liver DNA from intraperitoneally (i.p.) treated rats (fluorimetric assay); 2) DNA repair as unscheduled DNA synthesis (UDS) induced in cultured human peripheral blood lymphocytes (HPBL); and 3) sister chromatid exchanges (SCE) in HPBL [12].
  • Comparative effects of herbicide dicamba and related compound on plant mitochondrial bioenergetics [9].
  • Differences were not observed among the four hormone treatments that contained dicamba, nevertheless, these treatments significantly increased the production of caryopses, embryos and haploid plants [13].
 

Anatomical context of dicamba

  • Our results in this study suggest that the herbicide and peroxisome proliferator Dicamba has the ability to activate nuclear factor-kappaB [14].
  • Lauric acid hydroxylase activity and CYP4A-reactive protein were increased in microsomes from male rats fed the highest level of dicamba [15].
 

Associations of dicamba with other chemical compounds

  • In conclusion, dicamba is a stronger mitochondrial respiratory chain inhibitor and uncoupler as compared to 2-chlorobenzoic acid [9].
  • Female and male Sprague Dawley rats (n = 4) were fed diets containing either 0, 1, or 3% Dicamba or 0.01% ciprofibrate for 7 days [14].
  • Extracts of this Fe0 treatment contained the same HPLC degradation peak observed with the Fe0 + Al or Fe(III) salt treatment of dicamba [16].
  • METHODS: We conducted a case (NHL n = 513)/control (n = 1506) study among men using age; province of residence; exposure to insect repellents containing DEET, phenoxy-herbicides, or dicamba; and gloves when handling pesticides [17].
  • Juglone, an inhibitor of PPIase, interfered with the normal ability of R seeds to germinate in the presence of dicamba, whereas S seeds did not germinate in the presence of dicamba or dicamba plus juglone [18].
 

Gene context of dicamba

  • GH3 was highly induced by dicamba within 3 days after treatment (DAT) and remained high at 7 DAT, but induction was much lower at 17 DAT [19].
  • The EDL (estimated detection limit) for this method is 0.1 microgram dicamba/L water (ppb) [20].
  • The cytogenetic effects exerted by the phenoxy herbicide dicamba and one of its commercial formulations banvel((R)) (57.71% dicamba) were studied in in vitro whole blood human lymphocyte cultures [21].
  • Selectivity of BAS 662H is additionally favoured by a higher crop tolerance to dicamba because of reduced foliar uptake of this herbicide in corn under the influence of diflufenzopyr [22].
 

Analytical, diagnostic and therapeutic context of dicamba

References

  1. A three-component dicamba O-demethylase from Pseudomonas maltophilia, strain DI-6: gene isolation, characterization, and heterologous expression. Herman, P.L., Behrens, M., Chakraborty, S., Chrastil, B.M., Barycki, J., Weeks, D.P. J. Biol. Chem. (2005) [Pubmed]
  2. Developmental toxicity of a commercial herbicide mixture in mice: I. Effects on embryo implantation and litter size. Cavieres, M.F., Jaeger, J., Porter, W. Environ. Health Perspect. (2002) [Pubmed]
  3. Cancer Incidence among Pesticide Applicators Exposed to Dicamba in the Agricultural Health Study. Samanic, C., Rusiecki, J., Dosemeci, M., Hou, L., Hoppin, J.A., Sandler, D.P., Lubin, J., Blair, A., Alavanja, M.C. Environ. Health Perspect. (2006) [Pubmed]
  4. Sphingomonas sp. strain SB5 degrades carbofuran to a new metabolite by hydrolysis at the furanyl ring. Kim, I.S., Ryu, J.Y., Hur, H.G., Gu, M.B., Kim, S.D., Shim, J.H. J. Agric. Food Chem. (2004) [Pubmed]
  5. Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health. McDuffie, H.H., Pahwa, P., McLaughlin, J.R., Spinelli, J.J., Fincham, S., Dosman, J.A., Robson, D., Skinnider, L.F., Choi, N.W. Cancer Epidemiol. Biomarkers Prev. (2001) [Pubmed]
  6. Modulation of the genotoxicity of pesticides reacted with redox-modified smectite clay. Sorensen, K.C., Stucki, J.W., Warner, R.E., Wagner, E.D., Plewa, M.J. Environ. Mol. Mutagen. (2005) [Pubmed]
  7. Genotoxicity of 2,4-D and dicamba revealed by transgenic Arabidopsis thaliana plants harboring recombination and point mutation markers. Filkowski, J., Besplug, J., Burke, P., Kovalchuk, I., Kovalchuk, O. Mutat. Res. (2003) [Pubmed]
  8. Promoting activity of the herbicide dicamba (2-methoxy-3, 6-dichlorobenzoic acid) in two stage hepatocarcinogenesis. Espandiari, P., Glauert, H.P., Lee, E.Y., Robertson, L.W. Int. J. Oncol. (1999) [Pubmed]
  9. Comparative effects of herbicide dicamba and related compound on plant mitochondrial bioenergetics. Peixoto, F., Vicente, J.A., Madeira, V.M. J. Biochem. Mol. Toxicol. (2003) [Pubmed]
  10. Analysis of dicamba degradation by Pseudomonas maltophilia using high-performance capillary electrophoresis. Yang, J., Wang, X.Z., Hage, D.S., Herman, P.L., Weeks, D.P. Anal. Biochem. (1994) [Pubmed]
  11. Genetic safety evaluation of pesticides in different short-term tests. Hrelia, P., Vigagni, F., Maffei, F., Morotti, M., Colacci, A., Perocco, P., Grilli, S., Cantelli-Forti, G. Mutat. Res. (1994) [Pubmed]
  12. Evaluation of genotoxic effects of the herbicide dicamba using in vivo and in vitro test systems. Perocco, P., Ancora, G., Rani, P., Valenti, A.M., Mazzullo, M., Colacci, A., Grilli, S. Environ. Mol. Mutagen. (1990) [Pubmed]
  13. Differences among auxin treatments on haploid production in durum wheat x maize crosses. García-Llamas, C., Martín, A., Ballesteros, J. Plant Cell Rep. (2004) [Pubmed]
  14. Activation of hepatic NF-kappaB by the herbicide Dicamba (2-methoxy-3,6-dichlorobenzoic acid) in female and male rats. Espandiari, P., Ludewig, G., Glauert, H.P., Robertson, L.W. J. Biochem. Mol. Toxicol. (1998) [Pubmed]
  15. The herbicide dicamba (2-methoxy-3,6-dichlorobenzoic acid) is a peroxisome proliferator in rats. Espandiari, P., Thomas, V.A., Glauert, H.P., O'Brien, M., Noonan, D., Robertson, L.W. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1995) [Pubmed]
  16. Remediating dicamba-contaminated water with zerovalent iron. Gibb, C., Satapanajaru, T., Comfort, S.D., Shea, P.J. Chemosphere (2004) [Pubmed]
  17. Insect repellents, phenoxyherbicide exposure, and non-Hodgkin's lymphoma. McDuffie, H.H., Pahwa, P., Robson, D., Dosman, J.A., Fincham, S., Spinelli, J.J., McLaughlin, J.R. J. Occup. Environ. Med. (2005) [Pubmed]
  18. Proteome-level differences between auxinic-herbicide-susceptible and -resistant wild mustard (Sinapis arvensis L.). Yajima, W., Hall, J.C., Kav, N.N. J. Agric. Food Chem. (2004) [Pubmed]
  19. Quantitative expression analysis of GH3, a gene induced by plant growth regulator herbicides in soybean. Kelley, K.B., Lambert, K.N., Hager, A.G., Riechers, D.E. J. Agric. Food Chem. (2004) [Pubmed]
  20. Capillary column gas chromatographic determination of dicamba in water, including mass spectrometric confirmation. Jimenez, N.C., Atallah, Y.H., Bade, T.R. Journal - Association of Official Analytical Chemists. (1989) [Pubmed]
  21. Genotoxicity analysis of the phenoxy herbicide dicamba in mammalian cells in vitro. Gonz??lez, N.V., Soloneski, S., Larramendy, M.L. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  22. On the mechanism of selectivity of the corn herbicide BAS 662H: a combination of the novel auxin transport inhibitor diflufenzopyr and the auxin herbicide dicamba. Grossmann, K., Caspar, G., Kwiatkowski, J., Bowe, S.J. Pest Manag. Sci. (2002) [Pubmed]
  23. Development of an enzyme-linked immunosorbent assay for the detection of dicamba. Clegg, B.S., Stephenson, G.R., Hall, J.C. J. Agric. Food Chem. (2001) [Pubmed]
 
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