TY - JOUR
T1 - Metabolic O-dealkylation of 1-(4′-ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene, potent juvenoids
AU - Hammock, Bruce D.
AU - Gill, Sarjeet S.
AU - Hammock, Lassie
AU - Casida, John E.
PY - 1975
Y1 - 1975
N2 - 1-(4′-Ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene (the ethyl-methoxide and ethyl-ethoxide) are more stable in some biological systems and less stable in others than 1-(4′-ethylphenoxy)-3,7-dimethyl-6,7-epoxy-trans-2-octene (the ethyl-epoxide). In housefly adults and mealworm pupae the persistence increases in the order of the ethyl-epoxide, -methoxide and -ethoxide but with adult stable flies the epoxide is of intermediate stability. The alkoxides are metabolized in living insects and microsomal oxidase systems of houseflies and mouse liver mainly by O-dealkylation, at a higher rate for the methoxide than the ethoxide, but benzylic oxidation of the ethyl group also occurs and is more important in the degradation of the ethyl-epoxide than the ethyl-alkoxides. The photostability on silica gel is slightly better for the ethyl-ethoxide than the -methoxide or -epoxide.
AB - 1-(4′-Ethylphenoxy)-3,7-dimethyl-7-methoxy or ethoxy-trans-2-octene (the ethyl-methoxide and ethyl-ethoxide) are more stable in some biological systems and less stable in others than 1-(4′-ethylphenoxy)-3,7-dimethyl-6,7-epoxy-trans-2-octene (the ethyl-epoxide). In housefly adults and mealworm pupae the persistence increases in the order of the ethyl-epoxide, -methoxide and -ethoxide but with adult stable flies the epoxide is of intermediate stability. The alkoxides are metabolized in living insects and microsomal oxidase systems of houseflies and mouse liver mainly by O-dealkylation, at a higher rate for the methoxide than the ethoxide, but benzylic oxidation of the ethyl group also occurs and is more important in the degradation of the ethyl-epoxide than the ethyl-alkoxides. The photostability on silica gel is slightly better for the ethyl-ethoxide than the -methoxide or -epoxide.
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U2 - 10.1016/0048-3575(75)90038-3
DO - 10.1016/0048-3575(75)90038-3
M3 - Article
AN - SCOPUS:0016662857
VL - 5
SP - 12
EP - 18
JO - Pesticide Biochemistry and Physiology
JF - Pesticide Biochemistry and Physiology
SN - 0048-3575
IS - 1
ER -