N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N＇-取代基硫脲衍生物的合成及杀虫活性的研究(英文)

Synthesis and Insecticidal Activities of N-( 5-Dehydroabietyl-1,3,4-thiadiazol-2-yl)-N'-substituted Thioureas

为了寻求无公害的杀虫剂,设计合成了系列新型的含有去氢枞酸骨架的1,3,4-噻二唑衍生物。利用1H NMR、IR、MS和元素分析等手段对所合成新化合物进行了分析和表征。探讨了化合物对棉铃虫(Helicoverpa armigera)、玉米螟(Ostrinia nubilalis)和小菜蛾(Plutella xylostella)的杀虫活性。研究表明在200 mg/L质量浓度下,化合物N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-苯基硫脲(3a)和N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-间甲基苯基硫脲(3c)对棉铃虫具有良好的杀虫活性,防效率分别达到93.3%和83.3%,而化合物N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-邻甲基苯基硫脲(3b)、N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-间甲基苯基硫脲(3c)、N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-对甲基苯基硫脲(3d)和N-(5-去氢枞基-1,3,4-噻二唑-2-基-)-N'-对氯苯基硫脲(3i)对玉米螟具有一定的杀虫活性,防效率分别为66.7%、66.7%、73.3%和60%;此外,对化合物构效关系也进行了讨论,发现苯环上4位取代基对棉铃虫和玉米螟的防效率贡献分别为H>CH3>Cl>CF3>OCH3>Br=F和CH3>Cl>Br>F>H=CF3>OCH3。

In order to search for biorational pesticides, a series of novel 1,3,4-thiadiazole thiourea derivatives （3a-3k） containing dehydroabietic acid （ DHA） structure were designed and synthesized. Their structures were characterized by IR, MS, NMR, and elemental analysis. The insecticidal activities were investigated against cotton bollworm （ Helicoverpa armigera） , corn borer （ Ostrinia nubilalis ） , and diamondback moth （ Plutella xylostella ） . The preliminary bioassay showed that, at the concentration of 200 mg/L, compounds 3a and 3c exhibited excellent insecticidal activities against H. armigera, with mortality rates of 93. 3% and 83. 3%, respectively, and compounds 3b, 3c, 3d, and 3i displayed moderate insecticidal activities against O. nubilalis with mortality rates of 66. 7%, 66. 7%, 73. 3%, and 60%, respectively. In addition, the structure-insecticidal activity relationship of these compounds was discussed,too.