The importance of trifluoromethyl pyridines in crop protection

• Published in: Pest management science Vol. 74; no. 6; pp. 1228 - 1238
• Main Authors: Burriss, Adam, Edmunds, Andrew JF, Emery, Daniel, Hall, Roger G, Jacob, Olivier, Schaetzer, Jürgen
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01-06-2018; Wiley Subscription Services, Inc
• Subjects: Agricultural economics; agronomic; Agronomy; Biological properties; Chemists; Commercialization; Crops; Fluorination; Fungicides; Herbicides; Ingredients; Insecticides; Intermediates; Molecular chains; molecular matched pair analysis; Nematicides; physico‐chemical properties; Plant protection; Pyridines; Substitutes; trifluoromethyl pyridine; agronomic; trifluoromethyl pyridine; physico-chemical properties; molecular matched pair analysis
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.4806

The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporated into molecules with useful biological properties. During the period 1990 to September 2017, 14 crop protection products bearing a trifluoromethyl pyridine have been commercialized or proposed for an ISO common name, covering fungicides, herbicides, insecticides and nematicides. Chemical processes have been developed to provide trifluoromethyl pyridine intermediates, from non‐fluorinated pyridine starting materials, at scale and with affordable costs of goods. These attractive starting materials were readily adopted by research chemists, and elaborated through simple chemical modifications into new active ingredients. In a second approach, substituted trifluoromethyl pyridine rings have been constructed from acyclic, trifluoromethyl starting materials, which again has served to identify new active ingredients. Molecular matched pair analysis reveals subtle, yet important differences in physicochemical and agronomic properties of trifluoromethyl pyridines compared with the phenyl analogues. This review focuses on the past 27 years, seeking to identify reasons behind the success of such research programmes, and inspire the search for new crop protection chemicals containing the trifluoromethyl pyridine ring. © 2017 Society of Chemical Industry
Incorporating a trifluoromethyl pyridine ring into research programs has successfully identified useful agrochemicals. We describe approaches used, with selected examples to illustrate the impact on physico‐chemical properties and biological activity.