Synthesis and Pesticide Activity of some New Arylic and Pyridylic Oxime Ether Derivatives of Ionone

Some oxime ether derivatives of α-ionone (۴-(۲,۶,۶-trimethyl-۲-cyclohexen-۱-yl)-۳-buten-۲-one) have been synthesized. Reaction of ۴-(۲,۶,۶-trimethyl-۲-cyclohexen-۱-yl)-۳-buten-۲-ketoxime with various chloro and fluoro aromatic and hetero aromatic compounds gave the corresponding oxime ether derivatives via aromatic nucleophilic substitution (SNAr). The structures of these compounds were elucidated by IR, ۱H NMR, ۱۹F NMR and ۱۳C NMR spectroscopic methods. All the compounds were screened in vitro against the common pistachio psylla, Agonoscena pistaciae, fifth instar nymphs. Results showed that compound ۳c (LC۵۰ value of ۲۲۷.۷۶ mg l-۱) was much more toxic to fifth instar nymphs ofcommon pistachio psylla than compound ۳a (LC۵۰ = ۱۵۳۹.۱۴ mg l-۱) and compound ۳f (LC۵۰ = ۵۶۹.۳۱۹ mg l-۱).

Keywords:

Oxime ether , pesticide , Synthesis , Ultrasonic irradiation , Agonoscena pistaciae