Synthesis, insecticidal and fungicidal activities of methyl 2-(methoxyimino)-2-(2-((1-(N′-nitrocarbamimidoyl)-2-hydrocarbylidenehydrazinyl)methyl)phenyl)acetates

Abstract

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 LC₅₀ 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.