Barban (4-Chloro-2-butynyl N-(3-chlorophenyl) carbamate) 
After treatment with barban, plants formed a water-soluble 3-chloro- 
aniline compound. Related carbamates were found to form similar products. 
Another metabolite detected, also in a bound state, was 2-chloro-4-amino- 
phenol (Riden and Hopkins, 1962). 
oH NH 
<_— ‘CHg-CSC-CH,CI " 
2-Chloro-4- 
3-Chloro- " Ct Barban Aminophenol 
Aniline 
Bayer 73 (Ethanolamine salt of N-(2-chloro-4-nitrophenyl) -5-chlorosalicyl- 
amide) 
Following oral adminis tration of labeled Bayer 73 to rats, there was 
still 55% of activity present after one hour and 10% after five hours. 
About 33% of the applied activity appeared in the urine and 67% in the 
feces. Within 24 hours after administration, storage in tissue of rats 
was less than 1 ppm. Only 12% was detected in the urine of humans that 
injested the material. 
Unchanged active ingredient was excreted in the urine of rats in 
very small amounts as a conjugate. The main metabolite, N-(2-chloro- 
4-aminobenzene) -5-chloro-salicylamide, was also excreted in the urine 
in a conjugated form (Duhm et al., 1963). 
MH mp Rat 
Osan O AN q 
2 NH, 
+ 
Cl H CI 
d Cl 
Bayer 73 (As a Conjugate) 
30 
