Synthesis, insecticidal and fungicidal activities of methyl 2-(methoxyimino)-2-(2-((1-(N′-nitrocarbamimidoyl)-2-hydrocarbylidenehydrazinyl)methyl)phenyl)acetatesElectronic supplementary information (ESI) available: The synthetic procedures and NMR spectra of the intermediates, and the NMR and HRMS spectra of the title compounds are freely available. See DOI: 10.1039/c5ra27359e

• Main Authors: Yuan, Xiaoyong, Jia, Changqing, Ma, Yongqiang, Yang, Dongyan, Rui, Changhui, Qin, Zhaohai
• Format: Journal Article
• Published: 17.02.2016
• ISSN: 2046-2069
• DOI: 10.1039/c5ra27359e

N ′-Nitro-2-hydrocarbylidenehydrazinecarboximidamides and methoxyacrylates are two types of important agrochemicals. By combining their key fragments into one framework, a series of the title compounds was designed and synthesized. Some of these compounds have shown excellent insecticidal activities for aphides, for example, the LC 50 values of compounds 6-06 , 6-11 and 6-19 against M. perslcae and H. amygdale were found to be 1.9/14.4, 13.4/1.5 and 0.3/38.4 mg L −1 respectively. They were also effective against the mycelium growth of B. cinerea in vitro . Compound 6-04 could control (∼100%) cucumber anthrax and rice blast at 100 mg L −1 in vivo , and inhibit the spore germination (∼100%) of vegetable gray mold at 6.25 mg L −1 . These compounds could be considered as potential insecticidal or fungicidal candidates for crop protection. The results of structure-activity relationship (SAR) studies are discussed. By combining the sub-structures of strobilurin and guadipyr analogues in one molecule, a series of compounds was designed and synthesized. Some compounds showed excellent insecticidal activity or fungicidal activity.