46
INDOLE-3-ACETIC ACID
OAAJ
2,4-0
o
II
CIA
H
H 2 NJOCI
D
CH20~
CI
-
OH
_R-fi
HO
0 C_~
OH
CI
NH2
CHLORAMBEN
DICLOFOP -METHYL
Richard H. Shimabukuro et al.
Figure 2.19. Glucosyl esters of IAA, 2,4-D, chloramben, and diclofop-methyl.
jugated both as a l3-glucoside and a l3-gentiobioside (Fig. 2.20) (Hodgson et al.,
1973). A recent report indicated the acylation of the l3-glucoside to a malonyl
glucoside in resistant soybeans (Hoffer and Hodgson, 1978). The cleavage of
ftuorodifen by glutathione S-transferase gave free p-nitrophenol (Shimabukuro
et al., 1973a) that was conjugated as the l3-glucoside and a malonyl glucoside
(Shimabukuro et al., 1975). Flamprop-methyl was hydrolyzed in wheat and
conjugated as a glucose ester followed by acylation to a malonyl glucose ester
(Fig. 2.20) (Dutton et al., 1976). Complex acidic glucosides of insecticides have
not been detected in plants, but an acidic metabolite of tetrachlorvinphos that
readily hydrolyzed to the l3-glucoside has been reported (Beynon et al., 1973).
However, the acidic conjugate has not been characterized.