Chemistry and Biology of Oxyacetamides, Tetrazolinones, and Triazolinones

This chapter describes the development processes of herbicidal compounds that are thought to inhibit the biosynthesis of very-long-chain fatty acids (VLCFAs), which are classified as Group 15 herbicides. This class includes several key substance types, such as chloroacetamides, thiophosphates, oxyacetamides, and carbamoyl heterocycles. Following the introduction of the first chloroacetamide (alachlor) in 1969 by the Monsanto Company, a variety of these VLCFA-inhibiting compounds have been commercialized. Specifically, this chapter describes the development of selected representatives of these products, including two heteroaryloxyacetamides (mefenacet and flufenacet) and a carbamoyl tetrazolinone (fentrazamide), marketed by Bayer CropScience AG, as well as a carbamoyl triazolinone (ipfencarbazone), developed by Hokko Chemical Industry.