Wang Yanyan, Xu Fangzhou, Yu Gang, Shi Jun, Li Chuanhui, Dai A'li, Liu Zhiqian, Xu Jiahong, Wang Fenghua, Wu Jian
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang, 550025, China.
Chem Cent J. 2017 Jun 5;11(1):50. doi: 10.1186/s13065-017-0279-z.
The diacylhydrazine derivatives have attracted considerable attention in recently years due to their simple structure, low toxicity, and high insecticidal selectivity. As well as 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole is an important scaffold in many insecticidal molecules. In an effort to discover new molecules with good insecticidal activity, a series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed.
Bioassays demonstrated that some of the title compounds exhibited favorable insecticidal activities against Helicoverpa armigera and Plutella xylostella. The insecticidal activity of compounds 10g, 10h, and 10w against H. armigera were 70.8, 87.5, and 79.2%, respectively. Compounds 10c, 10e, 10g, 10h, 10i, 10j and 10w showed good larvicidal activity against P. xylostella. In particular, the LC values of compounds 10g, 10h, and 10w were 27.49, 23.67, and 28.90 mg L, respectively.
A series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed. The results of insecticidal tests revealed that the synthesized diacylhydrazine derivatives possessed weak to good insecticidal activities against H. armigera and P. xylostella. Compounds 10g, 10h, and 10x showed much higher insecticidal activity than tebufenozide, and exhibited considerable prospects for further optimization. Primary structure-activity relationship revealed that phenyl, 4-fluoro phenyl and four fluorophenyl showed positive influence on their insecticidal activities, and introduction of a heterocyclic ring (pyridine and pyrazole) showed negative impacts on their insecticidal effects.
近年来，二酰肼衍生物因其结构简单、毒性低和杀虫选择性高而备受关注。此外，3-溴-1-(3-氯吡啶-2-基)-1H-吡唑是许多杀虫分子中的重要骨架。为了发现具有良好杀虫活性的新分子，合成并生物测定了一系列含有3-溴-1-(3-氯吡啶-2-基)-1H-吡唑骨架的二酰肼衍生物。
生物测定表明，一些目标化合物对棉铃虫和小菜蛾表现出良好的杀虫活性。化合物10g、10h和10w对棉铃虫的杀虫活性分别为70.8%、87.5%和79.2%。化合物10c、10e、10g、10h、10i、10j和10w对小菜蛾表现出良好的杀幼虫活性。特别是，化合物10g、10h和10w的LC值分别为27.49、23.67和28.90mg/L。
合成并生物测定了一系列含有3-溴-1-(3-氯吡啶-2-基)-1H-吡唑骨架的二酰肼衍生物。杀虫试验结果表明，合成的二酰肼衍生物对棉铃虫和小菜蛾具有弱至良好的杀虫活性。化合物10g、10h和10x表现出比虫酰肼更高的杀虫活性，并展现出进一步优化的可观前景。初步的构效关系表明，苯基、4-氟苯基和四氟苯基对其杀虫活性有积极影响，而引入杂环（吡啶和吡唑）对其杀虫效果有负面影响。
