2.4- Dichlorophenoxyacetic acid synthesis

Circadian rhythm of total protein synthesis— cytoplasm and chloroplasts of Gonyaulax polyhedra Sulfate incorporation in Udotea petiolata thalli Photosynthetic activity of phytoplankton Thymidine incorporation into Nostoc Chloroplast nucleoids of Zea mays Localization of chloroplast binding protein in cells of wheat leaves Distributon of [14C]-dichlorophenoxyacetic acid Donner et al. (13) Mariani and Favoli (14) Bourdier and Bohatier (15) Favoli and Grilli (16) Lindbeck et al. (17) Bronsema et al. (18)... 

Charles JM, Cunny HC, Wilson RD, et al Ames assays and unscheduled DNA synthesis assays on 2,4-dichlorophenoxyacetic acid and its derivatives. Mutat Res 444 207-16, 1999... 

Dichlorophenol and 2,4,5-trichlorophenol have been used in the synthesis of phenoxy acid herbicides, including 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-tri-chlorophenoxyacetic acid (2,4,5-T). 2,4,5-Trichlorophenol has also been used as a fungicide and a bactericide. 2,4,6-Trichlorophenol has been used as a pesticide. 2,3,4,6-Tetra-chlorophenol has been used as a fungicide (Lewis, 1993 Verschueren, 1996). Chlorophenols have also been formulated and used as salts in some applications. 

Other important sources of CP contamination include the synthesis and use (Table 8.1) of 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trich-... 

Yasuda, T., Yajima, Y., and Yamada, Y., Induction of DNA synthesis and callus formation from tuber tissue of Jerusalem artichoke by 2,4-dichlorophenoxyacetic acid, Plant Cell Physiol., 15, 321-329, 1974. Yeoman, M.M., Tissue Culture and Plant Science, Street, H.E., Ed., Blackwell s, Oxford, 1974, pp. 1-17. Zubr, J. and Pedersen, H.S., Characteristics of growth and development of different Jerusalem artichoke cultivars, in Inulin and Inulin-containing Crops, Fuchs, A., Ed., Elsevier, Amsterdam, The Netherlands, 1993, pp. 11-19. 

We can apply these ideas to the synthesis of the herbicide 2,4-D (2,4-dichlorophenoxyacetic acid). The most reasonable disconnection of an ether is the C-O bond because we know that ethers can be made from alkyl halides by substitution with an alkoxide anion. We don t at this stage need to decide exactly which alkyl halide or alkoxide to use, so we just write the synthons. 

In addition to its use in making resins and adhesives, phenol is also the starting material for the synthesis of chlorinated phenols and the food preservatives BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole). Fenta-chlorophenol, a widely used wood preservative, is prepared by reaction of phenol with excess CI2. T he herbicide 2,4-D (2,4-dichlorophenoxyacetic acid) is prepared from 2,4-dichlorophenol, and the hospital antiseptic agent hexa-chlorophene is prepared from 2,4,5-trichlorophenol. 

A clean method for the rapid and solventless synthesis of herbicides based on 2,4-dichlorophenoxyacetic acid (2,4-D esters) has been described in which... 

ORIGIN/INDUSTRY SOURCES/USES manufacture of industrial and agricultural products intermediate in chemical industry feedstock to manufacture 2,4-dichlorophenoxyacetic acid and its derivatives (germicides, soil sterilants) moth proofing antiseptics seed disinfectants organic synthesis... 

Dichlorophenoxyacetic acid is the important weed-killer known as 2,4-D. Outline the synthesis of this compound starting from benzene or toluene and acetic acid. 

Andreae WA, Venis MA, Jursic E, Dumas T (1968) Does ethylene mediate root growth inhibition by indole-3-acetic acid Plant Physiol 43 1375-1379 Anker L (1973) The auxin production of the physiological tip of the Avena coleoptile and the repression of tip regeneration by indoleacetic acid (not by naphthylacetic acid and 2,4-dichlorophenoxyacetic acid). Acta Bot Neerl 22 221-227 Anker L (1975) Auxin-synthesis inhibition by abscisic acid, and its reversal by gibberellic acid. Acta Bot Neerl 24 339-347... 

---