
structural change. The methyl derivative was less volatile than 2,4-D 
methyl ester, but more volatile than the 5-hydroxy-2,4-D methyl ester. 
It might be one of the other two hydroxy derivatives; however, 6-hydroxy- 
2,4-D was not detected (Holley, 1952; Jaworski and Butts, 1952: Jaworski 
et al., 1955; Evans and Smith, 1954; Bach, 1961). 
The free acid has been recovered from bean and corn plants after 
treatment with 2,4-D butoxyethanol and propylene glycol butyl esters 
(Hagen et al., 1949; Fang et al., 1951; Fang and Butts, 1954; Hay and 
Thimann, 1956; Szabo, 1963). On cotton, cucumbers, beans, and grain sorghum, 
labeled 2,4-D gave rise to ct 
“0, (Holley et al., 1950; Weintraub et al., 
1952a,b). Pea and tomato plants have also been studied (Fang, 1958). In 
young leaves and bolls of cotton, material chromatographically different 
from 2,4-D was formed. Sorghum converted 2,4-D to a complex different 
than that found in cotton (Morgan, 1963; Nencki and Giacosa, 1880; Weintraub 
et al, 1950, 1952a,b, 1953, 1954, 1956; Slife et al., 1962). 
Amino acids have been implicated in the formation of some compounds, 
as in the case of 2,4-dichlorophenoxyacetylaspartic acid (Andreae and 
Good, 1957; Bach and Fellig, 1961). Evidence indicates that 2,4-D moves 
through plants as a protein complex, which can be recovered after aqueous 
extraction and NaOH hydrolysis, into the roots where most of the degradation 
occurs (Canny and Markus, 1960). Glucose esters have also been suggested 
(Klambt, 1961; Crosby, 1964). Recent studies have shown that glucoside 
complexes are formed. From stem tissues of oats (Avena sativa), 1-0- 
(2,4-dichlorophenoxyacetyl)-8-D-glucose was isolated (Thomas et al., 1964b), 
and from stems of the kidney bean (Phaseolus vulgaris), the 2,5- and 2,3- 
62 
