title: Efficient synthesis of fused bicyclic ethers and their application in herbicide chemistry.
abstract: A series of triketones 2 and 3 featuring novel fused bicyclic aryl ethers have been prepared. The syntheses utilized ring-closing olefin metathesis (compounds 2), or oxidative cyclization of allylphenols as the key steps. The herbicidal activity of the targeted triketones 2 and 3 on various grasses and broad-leaved weeds was determined and compared with compound 1. The strength of the novel compounds 2 and 3 is their good herbicidal activity on broad-leaved weeds in post-emergent applications, whereas activity on grasses was inferior compared to 1. In addition, computational methods have been applied to provide a deeper understanding of the SAR found for compounds 2 and 3.
authors.affiliation: Syngenta Crop Protection Muenchwilen AG, Schaffhauseserstrasse, CH-4322 Stein, Switzerland.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Schaetzer
authors.affiliation: Syngenta Crop Protection Muenchwilen AG, Schaffhauseserstrasse, CH-4322 Stein, Switzerland.
authors.forename: Andrew J F
authors.initials: AJF
authors.lastname: Edmunds
authors.affiliation: Syngenta Crop Protection Muenchwilen AG, Schaffhauseserstrasse, CH-4322 Stein, Switzerland.
authors.forename: Katharina
authors.initials: K
authors.lastname: Gaus
authors.affiliation: Syngenta Crop Protection Muenchwilen AG, Schaffhauseserstrasse, CH-4322 Stein, Switzerland.
authors.forename: Stefano
authors.initials: S
authors.lastname: Rendine
authors.affiliation: Syngenta Crop Protection Muenchwilen AG, Schaffhauseserstrasse, CH-4322 Stein, Switzerland.
authors.forename: Alain
authors.initials: A
authors.lastname: De Mesmaeker
authors.affiliation: Syngenta Crop Protection AG, Werk Rosental, Schwarzwaldallee 215, CH-4058 Basel, Switzerland.
authors.forename: Willy
authors.initials: W
authors.lastname: Rueegg
mesh_terms: D000818:Animals; D020134:Catalytic Domain / Q000187:drug effects; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D018515:Plant Leaves / Q000187:drug effects*; D057685:Plant Weeds / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D004988:Ethers, Cyclic; D006540:Herbicides
keywords: 4-Hydroxyphenylpyruvate dioxygenase (HPPD); Benzoylcyclohexanedione; Structure–activity relationship (SAR); Triketone herbicide