Sedaxane

Inhibition of succinate dehydrogenase, the complex II in the mitochondrial respiration chain, has been known as a fungicidal mechanism of action since the first examples were marketed in the 1960s.

[3][4] By 2016, at least 17 further examples of this mechanism of action were developed by crop protection companies, with the market leader being boscalid, owing to its broader spectrum of fungal species controlled.

A base-catalysed aldol condensation between the aldehyde and cyclopropyl methyl ketone forms an α,β-unsaturated carbonyl compound which, when combined with hydrazine gives a dihydropyrazole derivative.

Further treatment with potassium hydroxide forms the second cyclopropyl ring and this material is converted to the aniline required for sedaxane formation by Buchwald–Hartwig amination using benzophenone imine in the presence of a palladium catalyst, followed by hydroxylamine.

[12] The risks of resistance developing can be reduced by using a mixture of two or more fungicides which each have activity on relevant pests but with unrelated mechanisms of action.

Pyrazole intermediate