Biotransformation (Metabolism) of Pesticides - Pesticide Biotransformation and Disposition - page 75

Table 5.1 Metabolism of Pesticides Catalyzed by Microsomal Enzymes
Reaction Example Reference

OXIDATION
CYP-DEPENDENT OXIDATIONS
N-dealkylation

Nicotine→nornicotine Papadopoulos (1964)

4-Nitrophenyl N,N -dimethyl
carbamate→4-nitrophenyl N -methyl
carbamate

Hodgson and Casida (1961); Strother
(1972)

Dimethoate→des N -methyl
derivatives

Lucier and Menzer (1970)

Dicrotophos→des N -methyl
derivatives

Tseng and Menzer (1974)

Atrazine, simazine, terbutryn,
propazine→ N -dealkylated derivatives

Adams et al. (1990); Rodriguez and
Harkin (1995); Hanioka et al. (1998,
1999)

Diuron→desmethyldiuron Abass et al. (2007a,b,c)

Neonicotinoids Schultz-Jander and Casida (2002); Shi

et al. (2009)

O-dealkylation
Ether cleavage Methoxychlor→mono- and

dihydroxy derivatives

Bikadi and Hazai (2008); Kapoor
et al. (1970); Kishimoto et al. (1995);
Kurihari and Oka (1991)

Propoxur→2-hydroxyphenyl
N -methyl carbamate

Oonithan and Casida (1968, 1966)

Alachlor→RCH 2 OH→HCHO Jacobsen et al. (1991)

Alachlor, butachlor→O - dealkylated
derivatives

Kimmel et al. (1986); Hodgson et al.
(1998); Coleman et al. (1999, 2000)

Ester cleavage Chlorfenvinphos→desethyl

derivatives

Donninger et al. (1967, 1972) ; Hutson
(1981)

EPN oxon→desmethyl EPN oxon Nomeir and Dauterman (1979)

Amide cleavage Chlordimeform, amitraz Kimmel et al. (1986)

Aldrin→dieldrin Kulkarni and Hodgson (1984a)

Ring
hydroxylation via
arene oxide

Carbaryl→4- and 5-hydroxycarbaryl Dorough and Casida (1964); Hutson

(1981)

Naphthalene→naphthalene epoxide Cho et al. (2006); Jerina et al. (1968,

1970)

Dieldrin→12-hydroxydieldrin Hutson (1976); Baldwin et al. (1972)

Methoxychlor Dehal and Kupfer (1994)

Terbutol Suzuki et al. (2001)

Side-chain
hydroxylation

Carbaryl→ N -hydroxymethyl
carbaryl

Dorough and Casida (1964); Hutson
(1981); Tang et al. (2002)

Butacarb→hydroxybutyl derivatives Douch and Smith (1971a,b)

TOCP→hydroxmethyl TOCP cyclic
phosphate

Eto et al. (1962)

Pyrethrins→hydroxymethyl
derivatives

Casida et al. (1975-1976); Class et al.
(1991)

( Continued )