Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Key Laboratory of Integrated Management of Crop Diseases and Pests (Ministry of Education), College of Plant Protection, Nanjing Agricultural University, Nanjing, Jiangsu 210095, China.
J Agric Food Chem. 2021 Mar 17;69(10):3005-3014. doi: 10.1021/acs.jafc.0c04786. Epub 2021 Mar 2.
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 . Notably, compound at 0.75 mg/L lowered the LC value of imidacloprid against by 6.54-fold, while a 3.50-fold reduction of the LC value was observed for IPPA08. The results of bee toxicity test showed that compound display selectivity in its effects on imidacloprid toxicity against the honey bee ( 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.
杀虫剂增效剂因其具有降低有效成分剂量即可提高农药防治效果的潜力而备受关注。我们之前曾报道过，顺式构型新烟碱类化合物（IPPA08）对新烟碱类杀虫剂表现出特定的增效活性。在这项研究中，我们通过硝基亚甲基化合物和戊二醛之间的简便双曼尼希缩合反应，将 IPPA08 的吡啶部分转化为苯基，合成了一系列 IPPA08 的结构类似物。所有的氧桥型新烟碱类化合物都被发现增加了吡虫啉对 的毒性。值得注意的是，化合物 在 0.75 mg/L 时将吡虫啉对 的 LC 值降低了 6.54 倍，而 IPPA08 则降低了 3.50 倍。蜜蜂毒性试验结果表明，化合物 对吡虫啉对蜜蜂（ L.）的毒性表现出选择性。总之，用苯基取代吡啶环是获得具有氧桥部分的新型新烟碱类杀虫剂增效剂的可行方法。
