69840-63-7Relevant academic research and scientific papers
Design, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues
Zhang, Xiao,Wang, Yiping,Xu, Zhiping,Shao, Xusheng,Liu, Zewen,Xu, Xiaoyong,Maienfisch, Peter,Li, Zhong
, p. 3005 - 3014 (2021/04/09)
Insecticide synergists are sought-after due to their potential in improving the pesticide control efficacy with a reduced dose of an active ingredient. We previously reported that a cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogues of IPPA08 by converting the pyridyl moiety of IPPA08 into phenyl groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found to increase the toxicity of imidacloprid against Aphis craccivora. Notably, compound 25 at 0.75 mg/L lowered the LC50 value of imidacloprid against A. craccivora by 6.54-fold, while a 3.50-fold reduction of the LC50 value was observed for IPPA08. The results of bee toxicity test showed that compound 25 display selectivity in its effects on imidacloprid toxicity against the honey bee (Apis mellifera L.). In summary, replacing the pyridyl ring with a phenyl ring was a viable approach to obtain a novel synergist with oxabridged moiety for neonicotinoid insecticides.
Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the housefly Musca domestica
Nishiwaki, Hisashi,Nakagawa, Yoshiaki,Takeda, David Y.,Okazawa, Atsushi,Akamatsu, Miki,Miyagawa, Hisashi,Ueno, Tamio,Nishimura, Keiichiro
, p. 875 - 881 (2007/10/03)
Variously substituted benzyl derivatives of chloronlcotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF3 and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the α-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.
