Semisynthesis and Antifungal Activity of Novel Oxime Ester Derivatives of Carabrone Modified at C(4) against Botrytis cinerea

Abstract

To continuously improve the potential utility of the natural lead compound of carabrone in agrochemistry, carabrone oxime and 36 novel oxime ester derivatives of carabrone modified at C(4) were synthesized, and evaluated for their antifungal activities against Botrytis cinerea in vitro and in vivo. Of these 36 oxime ester derivatives, some compounds exhibited antifungal activities in vitro or in vivo. It was found that compounds with a pyridinyl residue can either efficiently inhibit spore germination or efficiently inhibit hyphal growth of B. cinerea, and compound 9 exhibited the highest activity in vitro and in vivo with IC50 and EC50 values of 1.17 and 12.9 μg/ml, respectively. Further, the structure-activity relationships are also discussed.

A functional analysis of mitochondrial respiratory chain cytochrome bc1 complex in Gaeumannomyces tritici by RNA silencing as a possible target of carabrone

“…The extraction of carabrone has been described previously by Minato et al (1964). Carabrone displays antibacterial and antitumour activities, and is associated with low toxicity and few negative effects on environmental health (Feng et al, 2010;Wang et al, 2014).…”

“…(1964). Carabrone displays antibacterial and antitumour activities, and is associated with low toxicity and few negative effects on environmental health (Feng et al ., 2010; Wang et al ., 2014). In our previous study, we reported that carabrone exerts significant antifungal activity against G. tritici (Wang et al ., 2017b, 2017c).…”

Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters

“…Based on its bioactive properties and chemical reactivity, verbenone deserves further study for pharmaceutical or agrochemical use. On the other hand, oxime ester derivatives were reported to possess diverse biological activities, such as anticancer [ 9 , 10 ], antiviral [ 11 , 12 ], antioxidant [ 13 , 14 ], insecticidal [ 15 , 16 ], antifungal [ 17 , 18 ], and herbicidal [ 19 , 20 ] properties. Although asymmetric oxime esters have ( E )- and ( Z )-isomers, the differences between their biological activities rarely receives attention.…”

The effect of carabrone on mitochondrial respiratory chain complexes inGaeumannomyces graminis

“…; Wang et al . , ). Moreover, carabrone has low toxicity and no threat to environmental health (Feng et al .…”

“…; Wang et al . , ). Therefore, carabrone is a promising botanical fungicidal component with significant effects against G. graminis .…”