Proinsecticide candidates N-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl derivatives of imidacloprid and 1-chlorothiazolylmethyl-2-nitroimino-imidazolidine.
Proinsecticide candidates N-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl derivatives of imidacloprid and 1-chlorothiazolylmethyl-2-nitroimino-imidazolidine.
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DOI：
10.1016/j.bmcl.2007.06.004
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发表时间：
2007-08
影响因子：
2.7
通讯作者：
Ikuya Ohno;Koichi Hirata;Chiharu Ishida;M. Ihara;K. Matsuda;S. Kagabu
中科院分区：
文献类型：
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作者：
Ikuya Ohno;Koichi Hirata;Chiharu Ishida;M. Ihara;K. Matsuda;S. Kagabu
制备了吡虫啉的前体药和在N3位点被氧二氧基掩盖的噻唑基甲基类似物。前药在pH 8.3的缓冲溶液和半衰期为10-15h的生理盐溶液中分解，释放出母体杀虫剂。与此相一致的是，通过膜片钳电生理学测量，在制备后24小时内，用掩蔽化合物溶液处理的解离蟑螂神经元会产生向内电流，而在制备后立即挑战这些溶液时，神经元没有观察到任何反应。对美洲蜚蠊的杀虫试验表明，各化合物在注射后24h的最小致死量为6.4×10−8mol，与吡虫啉及其噻唑衍生物的致死量相似。这一结果强烈暗示了活性成分在体内的再生。
Prodrugs of imidacloprid and the thiazolylmethyl analog masked with oxodioxolylmethyl group on the N3 site were prepared. The prodrugs decomposed in a buffer solution of pH 8.3 and in a physiological salt solution with half-lives of 10–15h, releasing the parent insecticides. Being consistent with this, an inward current was evoked in dissociated cockroach neurons treated with the masked compound solutions, which were maintained for 24h after preparation, as measured using patch–clamp electrophysiology, whereas no response was observed in neurons when the solutions were challenged immediately after preparation. The insecticidal test on the American cockroach showed that the minimum lethal dose for each compound at 24h after injection was 6.4×10−8mol, which was similar to that for imidacloprid and the thiazolyl derivative. This result strongly suggested a regeneration of the active ingredients in vivo.