Smejkal Tomas, Hachisu Shuji, Scutt James N, Willetts Nigel J, Sayer Danielle, Wildsmith Laura, Oliver Sophie, Thompson Caroline, Muehlebach Michel
Syngenta Crop Protection AG, Schaffhauserstrasse, CH-4332 Stein, Switzerland.
Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK.
Bioorg Med Chem Lett. 2018 Feb 1;28(3):339-343. doi: 10.1016/j.bmcl.2017.12.042. Epub 2017 Dec 20.
Novel 2-aryl-cyclic-1,3-diones containing a 5-methoxy-[1,2,5]triazepane unit were explored towards an effective and wheat safe control of grass weeds. Their preparation builds on the ease of synthetic access to 7-membered heterocyclic [1,2,5]triazepane building blocks. Substitution and pattern hopping in the phenyl moiety revealed structure-activity relationships in good agreement with previously disclosed observations amongst the pinoxaden family of acetyl-CoA carboxylase inhibitors. In light of basic physicochemical, enzyme inhibitory and binding site properties, the N-methoxy functionality effectively acts as a bioisostere of the ether group in the seven-membered hydrazine ring.
