Synthesis of pyripyropene derivatives and their pest-control efficacy
Synthesis of pyripyropene derivatives and their pest-control efficacy
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DOI：
10.1584/jpestics.d19-032
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发表时间：
2019-01-01
影响因子：
2.4
通讯作者：
Omura, Satoshi
中科院分区：
文献类型：
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作者：
Guro, Kimihiko;Horikoshi, Ryo;Omura, Satoshi
Pyripyropene A (PP-A) 是丝状真菌产生的次生代谢产物，对农业害虫具有杀虫活性。合成的PP衍生物还表现出较窄的杀虫谱，但对此类刺吸式害虫具有较高的杀虫活性。 PP-A 的生态毒理学影响较低，满足下一代杀虫剂的先决条件。我们研究了 3-吡啶基和 a-吡喃酮环转化为其他环的影响，以及天然 PP 类似物中 C-13 位的酯化、脱水和氧化对杀虫活性和谱的影响。 3-吡啶基和α-吡喃酮环的转化显着降低了杀虫活性，同时对谱的影响最小，表明这些环在杀虫活性中的重要作用。一些在 C-13 位进行结构修饰的衍生物对犬心丝虫和蚊媒的运动表现出比 PP-A 更高的抑制作用，表明它们可用作丝虫控制药物。
Pyripyropene A (PP-A), a secondary metabolite produced by filamentous fungi, shows insecticidal activity against agricultural insect pests. Synthesized PP derivatives also show a narrow insecticidal spectrum but high insecticidal activities against such sucking pests. PP-A has a low eco-toxicological impact and satisfies a prerequisite for next-generation insecticides. We investigated the effects of conversion of the 3-pyridyl and a-pyrone rings to other rings, as well as the effects of esterification, dehydration, and oxidization at the C-13 position in natural PP analogues, on the insecticidal activity and spectrum. The conversions of the 3-pyridyl and alpha-pyrone rings markedly reduced the insecticidal activity with a minimal impact on the spectrum, indicative of an important role for these rings in insecticidal activity. Some derivatives with modified structures at the C-13 position showed a higher inhibitory effect on the motility of canine heartworms and mosquito vectors than did PP-A, suggesting their utility as filaria control drugs.