Fluorine-containing agrochemicals in the last decade and approaches for fluorine incorporation

In this review, the methodologies for fluorine incorporation of 40 fluorine-containing agrochemicals that received an international standardization organization (ISO) name during the last decade are described. The predominant approach for fluorine introduction of these agrochemicals is to use a fluorine-containing building block. Here we present how the fluorine-containing building blocks are introduced into these agrochemicals. The synthetic methods of fluorine-containing building blocks that are not easily available are also specifically discussed. Fluoroarenes, difluomethylarenes and trifluomethylarenes are the main building blocks that have been used in this review. Fluorine-containing small molecules, such as alcohol, amine, ketoester, olefin are also widely used. The only example of late-stage fluorination is the synthesis of fungicide quinofumelin. We believe the fluorine introduction methods described here can provide ideas for the development of new and economical pesticide synthetic routes, and stimulate researchers to develop new fluorine incorporation methods and create new pesticides. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

This review describes the methodologies for fluorine incorporation of 40 fluorine-containing agrochemicals that have received an ISO name in the past decade. The predominant approach for fluorine introduction is through the use of fluorine-containing building blocks. The synthetic methods for hard-to-obtain fluorine-containing building blocks are specifically discussed. The main building blocks used include fluoroarenes, difluoromethylarenes, and trifluoromethylarenes, as well as fluorine-containing small molecules such as alcohols, amines, ketoesters, and olefins. The review also mentions the application of late-stage fluorination in the synthesis of the fungicide quinofumelin, and emphasizes the potential of these fluorine introduction methods in the development of new and economical pesticide synthetic routes.