Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity

Abstract

A broad range of benzophenone hydrazone derivatives was prepared and tested against selected chewing insect pests, allowing the analysis of structure-activity relationships. Good activity was found only when the aromatic rings were substituted at the 4-positions with an halogen atom and a triflate or perhaloalkoxy group. In contrast, a number of substituents on the hydrazone part led to active compounds, the best results being achieved with acyl-type substituents. The excellent laboratory and greenhouse activity of the best representatives was confirmed in semi-field trials against Spodoptera littoralis.

Separation, interconversion, and insecticidal activity of the cis‐ and trans‐isomers of novel hydrazone derivatives

“…The first insecticide containing a hydrazone moiety is hydramethylnon , which was commercialized in 1980. In recent years, many acylhydrazone derivatives with broad‐spectrum activity were reported as insecticidal agents , including metaflumizone, which was discovered by BASF (Badische Anilin‐und Soda‐Fabriken) and then commercialized in 2007 . However, these compounds exhibit two different configurations ( cis and trans ) due to the existence of the C=N double bond.…”

Synthesis and larvicidal and adult topical activity of some hydrazidehydrazone derivatives against Aedes aegypti

“…Many hydrazone derivatives have been reported to possess broad spectrum insecticidal activity and are used as active ingredients for controlling agricultural and horticultural pests [16][17][18]. For example, the first hydrazone type insecticide, hydramethylnon, was registered for use in the United States by the Environmental Protection Agency in 1980 to control ants and cockroaches [18].…”

Design, synthesis and bioactivity evaluation of novel benzophenone hydrazone derivatives

“…; R 1 = R 2 = R 3 = CH 3 ) which showed significant insecticidal activity . In 2001, the systematic structure–activity relationship (SAR) of benzophenone hydrazones derivatives was discussed by Böger and coworkers, who demonstrated that the hydrazone part is the only molecular area that could undertake significant structural modifications. However, to the best of our knowledge, there have been no reports on the acaricidal activities of benzophenone hydrazone derivatives against T. cinnabarinus .…”