Reducing copper use in the environment: the use of larixol and larixyl acetate to treat downy mildew caused by Plasmopara viticola in viticulture.

BACKGROUND: Plant extracts might provide sustainable alternatives to copper fungicides, which are still widely used despite their unfavourable ecotoxicological profile. Larch bark extract and its constituents, larixyl acetate and larixol, have been shown to be effective against grapevine downy mildew (Plasmopara viticola) under semi-controlled conditions. The aim of this study was to reduce the gap between innovation and the registration of a marketable product, namely to develop scalable extraction processes and to evaluate and optimise the performance of larch extracts under different conditions. RESULTS: Toxicologically and technically acceptable solvents like ethanol were used to extract the active compounds larixyl acetate and larixol from bark in sufficient amounts and their combined concentration could be increased by up to 39% by purification steps. The combined concentration of larixyl acetate and larixol from larch turpentine could be increased by up to 66%. The Minimal Inhibitory Concentration (MIC100 ) against P. viticola in vitro (6-23 µg mL-1 ) and the Effective Concentration (EC50 ) in planta under semi-controlled conditions (0.2-0.4 mg mL-1 ) were promising compared with other plant extracts. In vineyards, efficacies of larch extracts reached up to 68% in a stand-alone strategy and 84% in low-copper strategies. CONCLUSION: Larch extracts represent valid candidates for copper reduction in organic vineyards, and their development into a sustainable plant protection product might be feasible. © 2017 Society of Chemical Industry.

Cobalt catalysis at the crossroads: cobalt-catalyzed Alder-ene reaction versus [2 + 2] cycloaddition.

The application of bidentate phosphine ligands in cobalt-catalyzed transformations of cyclic alkenes such as cyclopentene and cycloheptene with internal alkynes led to a chemoselective Alder-ene or a [2 + 2] cycloaddition reaction depending on the electronic nature of the alkyne and the bite angle of the ligand used.

Cobalt-catalyzed 1,4-hydrovinylation of styrenes and 1-aryl-1,3-butadienes.

The application of aryl-substituted starting materials such as styrene and 1-aryl-substituted 1,3-butadiene derivatives in the cobalt-catalyzed 1,4-hydrovinylation reaction has been investigated. The use of unsymmetrical alpha,omega-dienes in the hydrovinylation with 1-aryl-1,3-butadiene led chemoselectively to the 1:1 or the 1:2 adducts depending on the stoichiometry of the starting materials.

Cobalt-catalysed hydrovinylation as the key step in a short synthesis of moenocinol.

A regio- and chemoselective cobalt(I)-catalysed 1,4-hydrovinylation reaction is the key step in the straightforward and convergent synthesis of moenocinol, the aglycone of moenomycin A.