Synthesis of Semiochemicals via Olefin Metathesis

Turczel, Gábor and Kovács, Ervin and Merza, Gabriella and Coish, Philip and Anastas, Paul T. and Tuba, Róbert (2019) Synthesis of Semiochemicals via Olefin Metathesis. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 7 (1). pp. 33-48. ISSN 2168-0485

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Abstract

Semiochemicals are substances or mixtures that carry messages and are used for communication between individuals of the same or different species. Semiochemicals that are used in pest control are called biopesticides. Conventional pesticides, which are generally synthetically derived and unnatural, inactivate or kill the pests, whereas biopesticides are naturally occurring compounds that attract insects to a trap or interfere with their reproduction. There are several advantages to biopesticides. Compared with conventional pesticides, biochemical-based pesticides are often less toxic and therefore have a significantly lower impact on human health and the environment. Moreover, biopesticides are pest-selective and as such do not negatively impact other organisms such as insects, mammals, or birds. Other advantages of biopesticides include high potency, meaning that smaller amounts of biopesticide are required, less resistance by target organisms, and the ability to biodegrade more quickly than conventional pesticides. Although biochemical-based pesticides are very promising materials, their production is often cumbersome, and their application is often limited. To date, most biopesticides have been synthesized by multistep, classical organic reactions that are not economical and have high environmental impact. However, in recent decades many efforts have been made to implement cost-effective and safer chemical procedures for the widespread application of biochemical-based pesticides. The purpose of this Perspective is to draw the attention of the green chemistry community to the applicability of olefin metathesis reactions in environmentally benign and cost-effective biopesticide synthesis. We review seminal work on the total synthesis of biopesticides using olefin metathesis as a key reaction step, and in doing so, we hope to inspire new ideas for forthcoming olefin-metathesis-based biopesticide development.

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