Current Contributions of Organofluorine Compounds to the Agrochemical Industry

Abstract

Summary Currently, more than 1,200 agrochemicals are listed and many of these are regularly used by farmers to generate the food supply to support the expanding global population. However, resistance to pesticides is an ever more frequently occurring phenomenon, and thus, a continuous supply of novel agrochemicals with high efficiency, selectivity, and low toxicity is required. Moreover, the demand for a more sustainable society, by reducing the risk chemicals pose to human health and by minimizing their environmental footprint, renders the development of novel agrochemicals an ever more challenging undertaking. In the last two decades, fluoro-chemicals have been associated with significant advances in the agrochemical development process. We herein analyze the contribution that organofluorine compounds make to the agrochemical industry. Our database covers 424 fluoro-agrochemicals and is subdivided into several categories including chemotypes, mode of action, heterocycles, and chirality. This in-depth analysis reveals the unique relationship between fluorine and agrochemicals.

Transition‐Metal Free Catalytic Synthesis of Trifluoromethyl Indolines by [4+1] Cycloaddition of Trifluoromethyl Benzoxazinones with Sulfur Ylides

“…Organofluorine compounds are promising candidates for pharmaceuticals and agrochemicals due to the unique effects of fluorine on chemical and physicochemical properties [1–4] . Nearly half of the FDA‐approved small‐molecule drugs in 2018 and 2019 are fluoro‐organic compounds [2,5–7] .…”

Environmentally Compatible Access to α‐Trifluoromethylseleno‐Enones

“…Nowadays, fluorinated molecules find more and more uses in a wide panel of applications, mainly due to their peculiar properties [1–13] . In the race of the development of molecules dedicated to targeted applications, fine tuning of physico‐chemical properties is highly investigated.…”

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions

“…Due to an impressively wide effect of fluorine on the biological activity, the insertion of fluorine atoms or fluorine-containing functional groups into organic molecules has become a common strategy in pharmaceutical and agrochemical industries [1][2][3][4][5]. Among various fluorine-containing functional groups, the trifluoromethyl (CF 3 ) group has received countless attention in the design of novel drugs [6,7].…”

“…One utility of the CF 3 group is the replacement of a methyl group in biologically active molecules to avoid the metabolic oxidation of a reactive methyl group in the parent molecules [8]. It should be noted that 19% out of 340 marketed fluoro-pharmaceuticals [4] and 42% out of 424 registered fluoro-agrochemicals [5] contain a CF 3 moiety in their structures (Figure 1), but this motif has never been found in nature [9]. Several notable examples of CF 3 -containing pharmaceuticals and agrochemicals include cinacalcet, efavirenz, travoprost, pexidartinib, fluoxetine, and upadacitinib ( Figure 2) [4,5].…”

“…Several notable examples of CF 3 -containing pharmaceuticals and agrochemicals include cinacalcet, efavirenz, travoprost, pexidartinib, fluoxetine, and upadacitinib ( Fig. 2 ) [ 4 – 5 ].…”