15945-64-9Relevant articles and documents
Biological Activity of Pyrethroid Analogs in Pyrethroid-Susceptible and -Resistant Tobacco Budworms, Heliothis virescens (F.)
Shan, Guomin,Hammer, Robert P.,Ottea, James A.
, p. 4466 - 4473 (2007/10/03)
The phenoxybenzyl moiety of conventional pyrethroids is a major site of oxidative metabolism in resistant tobacco budworms, Heliothis virescens (F.). In this study, this group was replaced with known P450 monooxygenase-inhibiting or oxidatively blocked groups. A variety of isomers (1R/1S, cis/trans) of the resulting chrysanthemates were tested as insecticides or synergists against tobacco budworms that were insecticide-susceptible (LSU) or that expressed metabolic resistance to cypermethrin (Pyr-R). A number of compounds with pentafluorophenyl, methylenedioxyphenyl, and propargyloxyphenyl groups were insecticidal, and activity was dependent on both geometric and stereochemical configuration of the acid moiety. Both trans and cis isomers of 1(R)-fenfluthrin, which contains a pentafluorophenyl group, suppressed resistance to cypermethrin in Pyr-R insects, confirming that oxidative metabolism of the phenoxybenzyl moiety is a major mechanism of resistance in this strain. Of the methylenedioxyphenyl compounds, 1R, trans, and cis isomers were toxic and partially suppressed resistance in Pyr-R larvae. Similarly, both trans and cis isomers of α(S),1(R)-propargyloxyphenyl-containing compounds were insecticidal. Finally, α(R),1(R)-cis-methylenedioxyphenyl- and -propargyloxyphenyl- containing compounds were nontoxic but significantly enhanced toxicity of cypermethrin.
