C-!*-1abeled bidrin or azodrin. No N,N-dimethylacetoacetamide, N-methyl- 
acetoacetamide, or 3-hydroxy-N,N-dimethylbutyramide was present in the 
milk and the nature of the C!* materials remained unknown. The major 
organoextractable P22 material in the milk following both bidrin and 
azodrin treatment was azodrin. Traces of the N-methyl-N-hydroxymethyl- 
amide and the unsubstituted amide were also present (984). 
Adult boll weevils and fifth-instar bollworm larvae were treated 
with labeled bidrin. Metabolites recovered were similar to those re- 
covered from rats (199). Houseflies and American cockroaches rapidly 
metabolized bidrin and azodrin to form the N-hydroxymethyl and N-de- 
methylated derivatives. Comparatively large amounts of the N-hydroxy- 
methylamide compounds were detected in flies treated with bidrin or 
azodrin alone but they were absent from extracts of flies treated with 
the toxicant plus sesamex; and only minute amounts of azodrin were 
detected in flies treated with bidrin plus sesamex (601, 984). 
In other studies absorbed azodrin was metabolized more rapidly in 
houseflies than in weevils. Hydroxymethyl azodrin was detected after 
4-8 hours in houseflies but not until after 24 hours in weevils. 
Dimethyl phosphate was the major hydrolysis product in houseflies; 
O-demethyl azodrin predominated in weevils (200). 
When cotton plants and leaves were treated with bidrin, initial 
detoxification included hydrolysis of the vinyl-phosphate bond to form 
dimethylphosphate and N,N-dimethylacetoacetamide; cleavage of a methyl- 
phosphate bond to form desmethyl bidrin and methanol; and hydrolysis of 
the amide bond to form bidrin acid and dimethylamine. One plant metab- 
olite was not identified, leaving a gap in the metabolic path of bidrin 
in plants (199). 
After injection into the stems, bidrin-P>” and azodrin p>? were 
rapidly translocated in bean plants and persisted for several weeks under 
greenhouse conditions. Half-life values for bidrin and azodrin were 9 
and 14 days respectively. Administration of bidrin yielded azodrin and 
traces of the N-methyl-N-hydroxymethylamide. Azodrin was identified by 
I.R. Following azodrin administration, traces of the mono-N-hydroxy- 
methylamide and the unsubstituted amide were present at eight days but 
only azodrin was present after twenty days (984). 
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