2,4-Dichlorophenoxyacetic acid metabolism

Because the metabolism of DEHP was relatively slow, the more readily hydrolyzed 2,4-dichlorophenoxyacetic acid-n-butyl ester was sometimes used for comparison. The hydrolysis of this compound, both by liver preparations and by serum also was inhibited by piperonyl butoxide. Liver homogenates from trout, which had been exposed to piperonyl butoxide in vivo, showed decreased capacity to metabolize DEHP (Table VIII). 

In additional in vitro studies with a number of methylene-dioxyphenyl compounds, only tropital, in addition to piperonyl butoxide, had similar inhibitory effects on the metabolism of DEHP by trout liver homogenates and serum (16). Of the methyl-enedioxyphenyl compounds studied, only tropital had a long side chain like that of piperonyl butoxide. This suggests that similarities in the side chains of these two compounds and the side chains of DEHP and 2,4-dichlorophenoxyacetic acid-n-butyl ester may be responsible for this inhibition. 

James, M. 0. and Bend, J. R. Taurine conjugation of 2,4-dichlorophenoxyacetic acid and phenylacetic acid as a major metabolic pathway in two marine species. Xenobiotica (1976)... 

Faulkner, J.K. and Woodstock, D. Metabolism of 2,4-dichlorophenoxyacetic acid (2,4-D) by AspergUlus nlger. Nature (London), 203 865, 1964. 

Feung, C. S., Hanrilton, R.H., and Mumma, R.O. Metabolism of 2,4-dichlorophenoxyacetic acid. V. Identification of metabolites in soybean callus tissue cultures. J. Agric. Food Chem., 21(4) 637-640, 1973. 

However, like TOL, TOM encodes the meta-fission of the resulting catechol (Figure 11.4). Consequently, it is unproductive in the assimilation of chloroaromatics like chlorobenzene and 2-chlorophenol, which are also metabolized to 3-chlorocatechol because of catechol 2,3-dioxygenase inactivation. To avoid a build-up of this product an ortho-cleavage enzyme and downstream enzymes for the complete catabolism of the product were recruited through the introduction of the 2,4-dichlorophenoxyacetic-acid-degradativeplasmid pROlOl (Kaphammer, Kukor Olsen, 1990). 

Verma, D.C., Tarvares, I, and Loewus, F.A., 1976, Effect of benzyladenine, 2,4-dichlorophenoxyacetic acid, and D-glucose in myo-inositol metabolism in Acer pseudoplatanus L. cells grown in suspension culture. Plant Physiol. 37 241-244. 

The metabolism of the herbicide 2,4-dichlorophenoxyacetic acid by A. niger has been examined. The major metabolite was 2,4-dichloro-5-hydroxyphenoxy-acetic add. This was accompanied by a minor product, 2,5-dichloro-4-hydroxy-phenoxyacetic add, in which a chlorine migration had taken place. 

OTHER COMMENTS used as an herbicide poisonous by ingestion substance is metabolized in the body into 2,4-D (Dichlorophenoxyacetic acid) physical and toxicological properties may change due to carrier solvents used in commercial formulations. 

Leguay JJ, Guern J (1977) Quantitative effects of 2,4-dichlorophenoxyacetic acid on growth of suspension-cultured Acer pseudoplatanus cells. II. Influence of 2,4-D metabolism and intracellular pH on the control of cell division by intracellular 2,4-D concentration. Plant Physiol 60 265-270... 

Differences of 2,4-D (2,4-dichlorophenoxyacetic acid) conjugation in wheat (tolerant) versus some broadleaf weeds (susceptible) exemplifies how Phase II metabolism imparts herbicide selectivity. Many susceptible broadleaf weeds produce glucose ester metabolites, which are readily susceptible to hydrolysis, yielding phytotoxic 2,4-D. Conversely, 2,4-D-tolerant wheat rapidly produces amino acid conjugates and 0-glucosides, which are stable, nonphytotoxic metabolites that are not easily hydrolyzed 11,12),... 

Faulkner JK, D Woodcock (1965) Fungal detoxication. Part VII. Metabolism of 2,4-dichlorophenoxyacetic and 4-chloro-2-methylphenoxyacetic acids by Aspergillus niger. J Chem Soc 1187-1191. 

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