Zectran [4-dimethylamino-3,5-xylyl methylcarbamate | 
The metabolism of zectran was studied by feeding labeled material 
to a male beagle dog. Urine was collected and fractionated and metabolites 
isolated and identified by chromatography. Sulfates and glucuronides were 
present in the urine as water soluble conjugates of 4-dimethylamino-3,5- 
xylenol and 2,6-dimethylhydroquinone. Three other materials were not 
identified (1503, 1504). 
After incubation of zectran with rat liver microsomes and NADPH), 
4-dimethylamino-3,5-xylyl N-hydroxymethylcarbamate and the 4-methylamino- 
4-amino, and 4-methylformamido-3,5-xylyl methylcarbamates were observed 
(1110, 1111, 1112). Similar results were obtained with fly homogenates. 
In addition to the four metabolites indicated, N-hydroxy zectran was also 
observed (3). 
When applied to broccoli, in addition to 4-dimethylamino-3,5-xylenol 
and 2,6-dimethylhydroquinone, 2,6-dimethyl-p-benzoquinone and 4-dimethyl- 
amino-3,5-dimethyl-o-benzoquinone were also found. Examination of methanol 
insoluble material indicated incorporation of zectran into the lignin where 
it probably is permanently stored (1503, 1504). 
After treatment of bean plants with zectran, at least eight compounds 
were found. Of these, 4-formamido-3,5-xylyl methylcarbamate, 4-methyl- 
formamido-3,5-xylyl methylcarbamate, 4-methylamino-3,5-xylyl methyl- 
carbamate, 4-amino-3,5-xylyl methylcarbamate were identified (3, 845). 
UV irradiation of zectran solutions affects zectran; however, 
no products have been identified (316, 391). Zectran on TLC plates was 
exposed to ultraviolet light (2537A) for 20 nours. After developing the 
chromatogram in one direction, the plate was again exposed to ultraviolet 
light for 20 hours, followed by development in the second direction and 
subsequent radioautography. From zectran, at least 12 degradation products 
were observed. Of these, only four were identified: the methylamino, 
amino, methylformamido, and formamido derivatives. These same major 
products were obtained from zectran when it was exposed to sunlight on 
bean foliage. The minor degradation products were the same in number 
and chromatographic position when formed on plant foliage or on TLC 
plates (€1, 2): 
After exposure to zectran, the larvae of spruce budworm and tobacco 
budworm converted zectran to nine metabolites; housefly larvae producted ten 
metabolites. Four of these found in all three insects, were identified: 
4-methylamino-, 4-amino-, 4-methylformamido-, and 4-formamido- 3,5-xylyl- 
methylcarbamates. One other compound was believed to be N-hydroxymethyl 
zectran (1780). 
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