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Chemical Compound Review

Humextra     2-chloro-N-(2-ethyl-6-methyl- phenyl)-N-(1...

Synonyms: Pimagral, Jindual, Metoken, Pennant, Bicel, ...
 
 
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Disease relevance of Humextra

 

High impact information on Humextra

 

Chemical compound and disease context of Humextra

 

Biological context of Humextra

 

Anatomical context of Humextra

  • A wild-type poplar hybrid and two transgenic clones overexpressing a bacterial gamma-glutamylcysteine synthetase in the cytosol or in the chloroplasts were exposed to the chloroacetanilide herbicides acetochlor and metolachlor dispersed in the soil [15].
  • "A most certaine and true relation of a strange monster or serpent found in the left ventricle of the heart of John Pennant, gentleman, of the age of 21 years" [16].
  • 4. Bile was the major route for 14C elimination when MAP metabolites of alachlor, butachlor and metolachlor were perfused into a renal artery [17].
  • The herbicide metolachlor induces liver cytochrome P450s 2B1/2 and 3A1/2, but not thyroxine-uridine dinucleotide phosphate glucuronosyltransferase and associated thyroid gland activity [18].
  • Identity of the metabolite was confirmed by TLC and positive ion thermospray LC/MS to be 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-1-methylethyl)acetamide . Hence, the reaction catalyzed by the sorghum microsomes involved O-demethylation of the methoxypropyl side chain of metolachlor [19].
 

Associations of Humextra with other chemical compounds

  • This paper compares two extraction techniques and two analytical techniques for 10 chemicals (metolachlor, seven triazines and two degradation products of atrazine-cyanazine-propazine and simazine) in the dissolved phase in large volumes of surface water, using a fibre glass filter with 0.7 micron porosity [20].
  • Although conditions favoring formation of sulfate green rust (GR(II); Fe6(OH)12SO4) facilitated Fe0-mediated dechlorination of metolachlor, only adsorption was observed when GR(II) was synthesized (without Fe0) in the presence of metolachlor and Eh/pH changed to favor Fe(III)oxyhydroxide or magnetite formation [21].
  • In anaerobic soil, the half-life was 38 d for atrazine and 62 d for metolachlor [22].
  • Degradation and leaching of the herbicides metolachlor and diuron: a case study in an area of Northern Italy [23].
  • Atrazine (1.1 kg a.i. ha-1), metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazine-5(4H)-one] (0.5 kg a.i. ha-1), and metolachlor (1.68 kg a.i. ha-1) were applied preemergence in a band over seeded corn (Zea mays L.) rows [24].
 

Gene context of Humextra

  • Phytoremediation of the herbicides atrazine and metolachlor by transgenic rice plants expressing human CYP1A1, CYP2B6, and CYP2C19 [25].
  • The GUS index, computed on data from microbiologically active soil, shows monuron as a leacher compound, EMA and DCA as non-leachers, metolachlor and diuron as transient ones [23].
  • The mobility of imazaquin through soil columns was in the order Rion > or = Norfolk > Cape Fear > or = Webster, whereas for metolachlor it was Rion > or = Norfolk >> Webster > or = Cape Fear [26].
  • Atrazine chlorohydrolase or ADP had no effect on the degradation of metolachlor [27].
  • In this study, the pulse-amplitude-modulation (PAM)-fluorometric method was used to evaluate the difference in the sensitivity to mercury (Hg) and metolachlor of six algal species: Ankistrodesmus falcatus, Selenastrum capricornutum, Chlorella vulgaris, Nannoplankton (PLS), Microcystis aeruginosa and Pediastrum biwae [28].
 

Analytical, diagnostic and therapeutic context of Humextra

  • Metolachlor is one of the most widely used herbicides in the United States. We evaluated the incidence of cancer among pesticide applicators exposed to metolachlor in the Agricultural Health Study, a prospective cohort study of licensed pesticide applicators in Iowa and North Carolina. A total of 50,193 pesticide applicators were included [1].
  • Although we used various inocula and enrichment culture techniques, we were not able to isolate microorganisms that could mineralize metolachlor [2].
  • When ELISA analyses were duplicated, cyanazine and metolachlor detection was found to have highly reproducible results; adjusted R2s were 0.97 and 0.94, respectively [29].
  • The two isomers were then thermally equilibrated to 1:1 mixtures of the aSS/aRS and aRR/aSR diastereomers, respectively, so that analytical data of all four metolachlor isomers became available; they were then used to identify these isomers in technical products by chiral high-resolution gas chromatography (HRGC) [30].
  • An evaluation of three pesticides: piritione, supercypermethrin and metolachlor in transformation bioassays of BHK21 and hamster embryo cells [31].

References

  1. Cancer incidence among pesticide applicators exposed to metolachlor in the Agricultural Health Study. Rusiecki, J.A., Hou, L., Lee, W.J., Blair, A., Dosemeci, M., Lubin, J.H., Bonner, M., Samanic, C., Hoppin, J.A., Sandler, D.P., Alavanja, M.C. Int. J. Cancer (2006) [Pubmed]
  2. Microorganisms capable of metabolizing the herbicide metolachlor. Saxena, A., Zhang, R.W., Bollag, J.M. Appl. Environ. Microbiol. (1987) [Pubmed]
  3. Effect of river and wetland sediments on toxicity of metolachlor. Karuppiah, M., Liggans, G., Gupta, G. Ecotoxicol. Environ. Saf. (1997) [Pubmed]
  4. Eye injuries among pennant squash players and their attitudes towards protective eyewear. Genovese, M.T., Lenzo, N.P., Lim, R.K., Morkel, D.R., Jamrozik, K.D. Med. J. Aust. (1990) [Pubmed]
  5. Metobromuron/metolachlor ingestion with late onset methemoglobinemia in a pregnant woman successfully treated with methylene blue. Yang, C.C., Hwang, S.F., Chou, M.M., Deng, J.F. J. Toxicol. Clin. Toxicol. (1995) [Pubmed]
  6. Isolation and characterization of glutathione S-transferase isozymes from sorghum. Gronwald, J.W., Plaisance, K.L. Plant Physiol. (1998) [Pubmed]
  7. Chiral iridium [corrected] xyliphos complexes for the catalytic imine hydrogenation leading to the metolachlor herbicide: isolation of catalyst-substrate adducts. Dorta, R., Broggini, D., Stoop, R., Rüegger, H., Spindler, F., Togni, A. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  8. 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]
  9. Effect of simulated sunlight on atrazine and metolachlor toxicity of surface waters. Lin, Y.J., Karuppiah, M., Shaw, A., Gupta, G. Ecotoxicol. Environ. Saf. (1999) [Pubmed]
  10. Developmental disorders in embryos of the frog Xenopus laevis induced by chloroacetanilide herbicides and their degradation products. Osano, O., Admiraal, W., Otieno, D. Environ. Toxicol. Chem. (2002) [Pubmed]
  11. Cytogenetic effects of cyanazine and metolachlor on human lymphocytes exposed in vitro. Roloff, B., Belluck, D., Meisner, L. Mutat. Res. (1992) [Pubmed]
  12. Postpartum haemorrhoids--evaluation of a cooling device (Anurex) for relief of symptoms. Thomas, I.L., Erian, M., Sarson, D., Yan, L., White, S., Battistutta, D. Med. J. Aust. (1993) [Pubmed]
  13. Enantiomeric separation of metolachlor and its metabolites using LC-MS and CZE. Klein, C., Schneider, R.J., Meyer, M.T., Aga, D.S. Chemosphere (2006) [Pubmed]
  14. Effects of the antimicrobial agent sulfamethazine on metolachlor persistence and sorption in soil. Accinelli, C., Hashim, M., Epifani, R., Schneider, R.J., Vicari, A. Chemosphere (2006) [Pubmed]
  15. Enhanced tolerance of transgenic poplar plants overexpressing gamma-glutamylcysteine synthetase towards chloroacetanilide herbicides. Gullner, G., Kömives, T., Rennenberg, H. J. Exp. Bot. (2001) [Pubmed]
  16. "A most certaine and true relation of a strange monster or serpent found in the left ventricle of the heart of John Pennant, gentleman, of the age of 21 years". Denham, D.A. Trans. R. Soc. Trop. Med. Hyg. (1977) [Pubmed]
  17. Comparative metabolism and elimination of acetanilide compounds by rat. Davison, K.L., Larsen, G.L., Feil, V.J. Xenobiotica (1994) [Pubmed]
  18. The herbicide metolachlor induces liver cytochrome P450s 2B1/2 and 3A1/2, but not thyroxine-uridine dinucleotide phosphate glucuronosyltransferase and associated thyroid gland activity. Dalton, S.R., Miller, R.T., Meyer, S.A. International journal of toxicology. (2003) [Pubmed]
  19. Metabolism of metolachlor by a microsomal fraction isolated from grain sorghum (Sorghum bicolor) shoots. Moreland, D.E., Corbin, F.T., Novitzky, W.P., Parker, C.E., Tomer, K.B. Z. Naturforsch., C, J. Biosci. (1990) [Pubmed]
  20. Determination of organonitrogen pesticides in large volumes of surface water by liquid-liquid and solid-phase extraction using gas chromatography with nitrogen-phosphorus detection and liquid chromatography with atmospheric pressure chemical ionization mass spectrometry. Sabik, H., Jeannot, R. Journal of chromatography. A. (1998) [Pubmed]
  21. Green rust and iron oxide formation influences metolachlor dechlorination during zerovalent iron treatment. Satapanajaru, T., Shea, P.J., Comfort, S.D., Roh, Y. Environ. Sci. Technol. (2003) [Pubmed]
  22. Anaerobic degradation of atrazine and metolachlor and metabolite formation in wetland soil and water microcosms. Seybold, C.A., Mersie, W., McNamee, C. J. Environ. Qual. (2001) [Pubmed]
  23. Degradation and leaching of the herbicides metolachlor and diuron: a case study in an area of Northern Italy. Barra Caracciolo, A., Giuliano, G., Grenni, P., Guzzella, L., Pozzoni, F., Bottoni, P., Fava, L., Crobe, A., Orrù, M., Funari, E. Environ. Pollut. (2005) [Pubmed]
  24. Tillage, intercrop, and controlled drainage-subirrigation influence atrazine, metribuzin, and metolachlor loss. Gaynor, J.D., Tan, C.S., Drury, C.F., Ng, H.Y., Welacky, T.W., van Wesenbeeck, I.J. J. Environ. Qual. (2001) [Pubmed]
  25. Phytoremediation of the herbicides atrazine and metolachlor by transgenic rice plants expressing human CYP1A1, CYP2B6, and CYP2C19. Kawahigashi, H., Hirose, S., Ohkawa, H., Ohkawa, Y. J. Agric. Food Chem. (2006) [Pubmed]
  26. Sorption and mobility of 14C-labeled imazaquin and metolachlor in four soils as influenced by soil properties. Weber, J.B., McKinnon, E.J., Swain, L.R. J. Agric. Food Chem. (2003) [Pubmed]
  27. Influence of microbial inoculation (Pseudomonas sp. strain ADP), the enzyme atrazine chlorohydrolase, and vegetation on the degradation of atrazine and metolachlor in soil. Zhao, S., Arthur, E.L., Coats, J.R. J. Agric. Food Chem. (2003) [Pubmed]
  28. Evaluation of different algal species sensitivity to mercury and metolachlor by PAM-fluorometry. Juneau, P., Dewez, D., Matsui, S., Kim, S.G., Popovic, R. Chemosphere (2001) [Pubmed]
  29. Comparison of enzyme-linked immunosorbent assay and gas chromatography procedures for the detection of cyanazine and metolachlor in surface water samples. Schraer, S.M., Shaw, D.R., Boyette, M., Coupe, R.H., Thurman, E.M. J. Agric. Food Chem. (2000) [Pubmed]
  30. Isolation and identification of the metolachlor stereoisomers using high-performance liquid chromatography, polarimetric measurements, and enantioselective gas chromatography. Müller, M.D., Poiger, T., Buser, H. J. Agric. Food Chem. (2001) [Pubmed]
  31. An evaluation of three pesticides: piritione, supercypermethrin and metolachlor in transformation bioassays of BHK21 and hamster embryo cells. Slamenová, D., Dusinská, M., Gábelová, A., Bohusová, T., Oravec, C. Cell Biol. Toxicol. (1992) [Pubmed]
 
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