Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 69, Issue 10, Pages 3005-3014Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c04786
Keywords
neonicotinoid; insecticide synergist; imidacloprid; selectivity
Funding
- National Key Research and Development Program of China [2017YFD0200500]
- Innovation Program of Shanghai Municipal Education Commission [2017-01-07-00-02-E00037]
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This study demonstrated that converting the pyridyl moiety of IPPA08 into phenyl groups can lead to a new synergist with oxabridged moiety for neonicotinoid insecticides, increasing its toxicity against Aphis craccivora while showing selectivity in its effects on honey bees.
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.
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