Recent Developments in Fluorine-Containing Agrochemicals

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

“…Currently, a new agrochemical cannot be approved unless its effects on air, water, soil, and human health are known (Vaz, 2019;Delorenzo et al, 2001;Ames and Gold, 1997;Bhattacharyya et al, 2009). Inspired by the potential efficiency of fluoro-DDT as an insecticide, the first fluoro-herbicide, trifluralin (Epp et al, 2018) introduced by Eli Lilly & Co. in 1963 (Figure 1C, also one of the most globally used herbicides), as well as our ongoing research into biologically active organofluorine compounds (Shibata, 2016), we were interested in the contributions of fluorine-containing agrochemicals (fluoro-agrochemicals) to the wider field of agrochemicals (Cartwright, 1994;Theodoridis, 2006;Fujiwara and O' Hagan, 2014;Jeschke, 2004;Haufe and Leroux, 2019;Pazenok and Leroux, 2020). Organofluorine compounds have emerged as attractive synthetic building blocks in the pharmaceutical industry (Wang et al, 2014;Ojima, 2009) following the use of the first successful fluoro-pharmaceutical, Florinef acetate, in 1954 (Figure 1D).…”

“…These aspects reveal a unique relationship between fluoroorganic compounds and agrochemicals. Although there are several articles that review fluorine-containing organic molecules in agrochemicals (Cartwright, 1994;Theodoridis, 2006;Fujiwara and O' Hagan, 2014;Jeschke, 2004;Haufe and Leroux, 2019;Pazenok and Leroux, 2020), to the best of our knowledge, our collection of 424 fluoro-agrochemicals with accompanying entries (5 inorganics) is the most comprehensive. The analysis of fluoro-agrochemical chemotypes is also a unique way to estimate the potential for success of a compound on the agrochemical market.…”

Advances in the Development of Trifluoromethoxylation Reagents

“…Fluorine chemistry is currently one of the most exciting areas of research, contributing to the modernization of materials [1], agriculture [2][3][4][5][6] and healthcare [7][8][9][10][11][12][13][14] industries. Particularly, the development of original synthetic methodology, allowing access to new fluorinated compounds with unique physicochemical and biological properties, is in very high demand in nearly every area of chemical industry [15][16][17][18][19][20][21].…”

“…In contrast, preparation of molecules bearing CF 3 -O-group is a noticeably less developed area of fluorine chemistry [25][26][27][28][29][30][31][32][33][34]. As a reflection of this apparent methodological deficit, pharmaceutical drugs and agrochemicals featuring trifluoromethoxy substituent, constitute less than 1.5% and 2.5% of the respective fluorine-containing marketed compounds [2][3][4][5][6][7][8][9][10][11][12][13][14][35][36][37][38]. Examples of the corresponding pharmaceutical drugs are presented in Figure 1, and agrochemicals are shown in Figure 2.…”

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

“…The incorporation of fluorine or fluorinated moieties into organic compounds plays a key role in life science-oriented research, as it can often result in profound changes to the physico-chemical and biological properties of the resulting compounds [ 1 ]. Therefore, organofluorine chemistry has become a new challenge in the context of small-molecule research in agro- [ 2 , 3 , 4 , 5 , 6 , 7 , 8 ] and medicinal chemistry [ 9 , 10 , 11 , 12 , 13 ]. Consequently, extensive and increasing attention has been devoted in the last decades to the development of new and more efficient methods for the introduction of fluorinated motifs.…”