Biology Reference
In-Depth Information
Chloroacetamide Herbicides—Alachlor and Butachlor
Alachlor and butachlor are representative of the chloroacetamide class of herbicides, their
chemical names and CAS numbers being as follows: alachlor, N -methoxymethyl-2 ,6 -
diethyl-2-chloroacetanilide and 15972-60-8; butachlor, N -(butoxyethyl)-2-chloro-2 ,6 -
diethylacetanilide and 23184-66-99. Alachlor, but not butachlor, is widely used in the
United States, primarily on corn. The metabolism of these herbicides has been studied in
surrogate animals and humans ( Figure 9.8 ) and their toxicology summarized ( Coleman
et al., 2000; Heydens et al., 2010 ).
O
O
O
O
N
N
Cl
Cl
Butachlor
Alachlor
RLM 0.045
HLM <0.001
RLM 0.035
HLM 0.003
P450
P450
O
O
NH
NH
CDEPA
Cl
Cl
RLM 0.350
HLM 0.841
RLM 0.350
HLM 0.841
Arylamidase
Arylamidase
NH 2
NH 2
DEA
RLM 0.041
HLM 0.040
RLM 0.041
HLM 0.040
P450
P450
NH 2
NH 2
HO
DEAOH
HO
Figure 9.8 In vitro metabolism of chloroacetamide herbicides—alachlor and butachlor.
Abbreviations: HLM, human liver microsomes; RLM, rat liver microsomes; CDEPA, 2-chloro- N -(2,6-
diethylphenylacetamide); DEA, 2,6-diethylaniline; DEAOH, 4-hydroxy-2,6-diethylaniline.
 
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