Chen Yao, Lei Zhi Wei, Zhang Ying, Yang Wen, Liu Hui Fang, Zhou Yu Feng, Yang Mao Fa
Institute of Entomology, Guizhou University, Guiyang 550025, Guizhou, China.
Guizhou Provincial Key Laboratory for Agricultural Pest Management of the Mountainous Region, Guizhou University, Guiyang 550025, Guizhou, China.
Molecules. 2017 Jun 25;22(7):1058. doi: 10.3390/molecules22071058.
Six new conjugates were designed and synthesized by introducing glucose, methyl glucuronate or glucuronic acid moieties on tralopyril. Phytotoxicity and phloem mobility results demonstrated that the introduction of glucose, methyl glucuronate or glucuronic acid moieties can simultaneously solve the tough phytotoxicity problem and phloem mobility transformation of tralopyril. Conjugates and containing the glucuronic acid moiety exhibited higher phloem mobility than conjugates , , and . Conjugates , and with methoxymethyl groups on the tralopyril pyrrole nitrogen atom showed activity against , while conjugates , and with a methene group on the pyrrole N showed no activity. Cabbage roots were incubated in a buffered solution containing conjugates , and at 4 mM for 72 h. Only showed systemic insecticidal activity with 100% mortalityagainst while and showed lower activity andchlorfenapyr showed no activity. The glucuronic acid promoiety imparted more phloem mobility to tralopyril than glucose and methyl glucuronate. The methoxymethyl group bond on the tralopyril skeleton was the key factor in determining the insecticidal activity of the conjugates. A promising systemic proinsecticide containing glucuronic acid and tralopyril moieties was proposed.
通过在三氯吡螨酯上引入葡萄糖、甲基葡糖醛酸或葡糖醛酸部分，设计并合成了六种新的共轭物。植物毒性和韧皮部流动性结果表明，引入葡萄糖、甲基葡糖醛酸或葡糖醛酸部分可以同时解决三氯吡螨酯严重的植物毒性问题和韧皮部流动性转化问题。含有葡糖醛酸部分的共轭物 和 表现出比共轭物 、 、 和 更高的韧皮部流动性。在三氯吡螨酯吡咯氮原子上带有甲氧基甲基的共轭物 、 和 对 表现出活性，而在吡咯N上带有亚甲基的共轭物 、 和 没有活性。将白菜根在含有4 mM共轭物 、 和 的缓冲溶液中孵育72小时。只有 表现出全身杀虫活性，对 死亡率达100%，而 和 活性较低，氯虫腈没有活性。葡糖醛酸部分赋予三氯吡螨酯的韧皮部流动性比葡萄糖和甲基葡糖醛酸更多。三氯吡螨酯骨架上的甲氧基甲基键是决定共轭物杀虫活性的关键因素。提出了一种含有葡糖醛酸和三氯吡螨酯部分的有前景的全身前体杀虫剂。
