Spirodiclofen ether derivatives: semisynthesis, structural elucidation, and pesticidal activities against Tetranychus cinnabarinus Boisduval, Aphis citricola Van der Goot and Mythimna separata Walker.

Abstract

Spirodiclofen is a spirocyclic tetronic acid-type acaricidal agent. Nowadays, serious pests resistance to spirodiclofen and cross-resistance to other acaricides has appeared. To overcome pests resistance and discover new potential agrochemicals, a series of ether derivatives were prepared based on spirodiclofen as a lead compound. Their pesticidal activities were investigated against three typically agricultural pests, Mythimna separata Walker, Aphis citricola Van der Goot and Tetranychus cinnabarinus Boisduval. Four steric structures of compounds 5e, 5f, 5i and 5j were determined by single-crystal X-ray diffraction. Against T. cinnabarinus, compounds 5b, 5f and 5l exhibited potent acaricidal activity, and their good control effects in the glasshouse were observed when compared with spirodiclofen, especially the control efficiency of compound 5b was comparable to that of spirodiclofen; against M. separata, compound 5j showed > 1.8-fold potent insecticidal activity of spirodiclofen; against A. citricola, compounds 5d and 5j displayed > 2.0-fold potent aphicidal activity of spirodiclofen. The relationships between their structures and agricultural activities were also discussed. Compounds 5b and 5d could be further studied as acaricidal and aphicidal agents, respectively; compound 5j can be considered as a lead compound for the insecticidal and aphicidal activities. This will pave the way for future application of these derivatives as pesticide substitutes for spirodiclofen. © 2021 Society of Chemical Industry.