Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers

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• 作者：Aiping Liu ; Wanqi Yu ; Minhua Liu ; Jianjun Bai ; Weidong Liu ; Xingping Liu ; Hui Pei ; Li Hu ; Mingzhi Huang ; Xiaoguang Wang
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2015
• 出版时间：September 2, 2015
• 年：2015
• 卷：63
• 期：34
• 页码：7469-7475
• 全文大小：389K
• ISSN：1520-5118

文摘

Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.