4,5,5-三氟-N-(杂芳基甲基)戊-4-烯酰胺的合成及杀线虫活性

Synthesis and nematicidal activity of 4,5,5-trifluoro-N-(heteroaryl methyl)pent-4-enamide

植物寄生线虫可能对全球农作物造成严重的危害。本研究设计合成了15个未见文献报道的4,5,5-三氟戊-4-烯酰胺衍生物,并测定了它们的离体活性和在沙土中的活体杀线虫活性,且进一步研究了沙土活体活性较好的化合物在基质中的活体杀线虫活性。离体测试结果表明:部分目标化合物表现出较好的杀线虫活性,其中含呋喃环的化合物B 8对南方根结线虫Meloidogyne incognita和松材线虫Bursaphelenchus xylophilus均表现出优异的杀线虫活性,LC50/72 h值分别为1.22 mg/L和0.53 mg/L。此外,在沙土活体活性测试中,大部分化合物在40 mg/L时对南方根结线虫具有100%的抑制作用,其中含苯并噻唑环的化合物B10的活性最好,在2.5 mg/L时抑制率为66.0%。在基质中的活体活性测试结果表明,含噻吩环的化合物B6活性最好,在5 mg/L时对南方根结线虫的抑制率为31.0%。初步的构效关系分析显示,含无取代五元环如噻吩、呋喃和噻唑的化合物的活性优于含大体积的六元环或稠环的化合物。

Plant parasitic nematodes may cause severe damages to crops globally.In this study,fifteen novel 4,5,5-trifluoropent-4-enamide derivatives were designed and synthesized,and their nematicidal activities both in vitro and in vivo(in sand)were determined.Compounds with high activity in sand were further investigated for their in vivo activities in matrix.Results of the in vitro test showed that some of compounds exhibited better nematicidal activity.Among the synthesized molecules,compounds B8 containing a furan ring exhibited excellent nematicidal activity against Meloidogyne incognita and Bursaphelenchus xylophilus,with LC50/72 h values of 1.22 mg/L and 0.53 mg/L,respectively.Furthermore,most of the compounds showed 100%inhibition rate against M.incognita at 40 mg/L in sand in the in vivo test.Among which compound B10 containing a benzothiazole ring showed the best nematicidal activity.It exhibited 66.0%inhibition rate at 2.5 mg/L.Results of the in vivo test in matrix showed that compound B6 containing a thiophene ring was the most active compound.It showed 31.0%inhibition rate at 5 mg/L.Preliminary analysis on structure-activity relationship showed that the compounds containing non-substituted five-membered ring such as thiophene,furan and thiazole demonstrated better bioactivity than those compounds containing bulky six-membered ring or fused ring in the molecule.