Discovery and biological profile of inpyrfluxam: A new broad-spectrum succinate dehydrogenase inhibitor fungicide

In vitro and in planta investigation of succinate dehydrogenase inhibitor resistance conferred by target‐site amino acid substitutions in Puccinia horiana, chrysanthemum white rust

“…horiana. 23 The most potent SDHI fungicide was inpyrfluxam in both in vitro and in planta assays against SdhC-I88F-harboring Pu. horiana (Figs 2 and 4).…”

Recent developments in fluorine‐containing pesticides

“…The (R)-enantiomer (optical purity >99%) is more than twice as active as the corresponding racemic mixture and as broad spectrum and systemic fungicide, especially highly effective against basidiomycetes and ascomycetes, such as brown patch (Rhizoctonia solani) and apple scab (Venturia inaequalis). 46 It demonstrates favorable systemic biological properties against Asian soybean rust (ASR) (Phakopsora pachyrhizi), important for soybean farmers in Brazil. Inpyrfluxam is suitable for the control of ASR, even in the presence of SDHI-resistant populations, making this fungicide an innovative protection of many key crops, including soybean culture.…”

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

“…48,49 Also, furametpyr (24) and inpyrfluxam (25) are both SDHIs, and the exchange of dihydrobenzofuran of furametpyr by an identical substutituted indane delivered inpyrfluxam (25), a fungicide with a higher potency and broader spectrum. 50,51 The application of resmethrin (26), an insecticide from the first generation of synthetic pyrethroids, was always limited to household mosquito control because of its insufficient photostability. The replacement of its furan by a phenyl ring delivered permethrin (27), which is perfectly stable in ultraviolet (UV) light and, therefore, could be used in agriculture (Scheme 4).…”

“…Oxathiine carboxamide carboxin ( 22 ) was launched in 1966 as the very first succinate dehydrogenase inhibitor (SDHI) to the market but never reached significant sales because of its limited spectrum as a seed treatment agent. Replacement of this non-aromatic heterocycle by a phenyl ring delivered mepronil ( 23 ), which still had a seed care focus, but its first foliar applications were the initial milestones in the evolution of the SDHIs from an unimportant niche mode of action to the currently fastest growing broad-spectrum fungicide class. , Also, furametpyr ( 24 ) and inpyrfluxam ( 25 ) are both SDHIs, and the exchange of dihydrobenzofuran of furametpyr by an identical substutituted indane delivered inpyrfluxam ( 25 ), a fungicide with a higher potency and broader spectrum. , The application of resmethrin ( 26 ), an insecticide from the first generation of synthetic pyrethroids, was always limited to household mosquito control because of its insufficient photostability. The replacement of its furan by a phenyl ring delivered permethrin ( 27 ), which is perfectly stable in ultraviolet (UV) light and, therefore, could be used in agriculture (Scheme ).…”