Synthesis of Novel Benzoylphenylurea Chitin Inhibitors from Chlorothalonil

Twenty-six novel benzoylphenylurea chitin inhibitor derivatives have been synthesized in over 30~50% yield from chlorothalonil 1 via sequential fluorine exchange, aminolysis, hydrolysis, decarboxylation and acylation reactions.

Synthesis of Novel Benzoylphenylurea Chitin Inhibitors From Chlorothalonil(Ⅱ)

Six novel benzoylphenylurea chitin inhibitor derivatives were synthesized in the yields of 30%_50% from the readily available starting material chlorothalonil 1 viasequential fluorine exchange, aminolysis, hydrolysis and acylation reactions.

Chitin synthesis inhibitors： old molecules and new developments

Chitin is the most abundant natural aminopolysaccharide and serves as a structural component of extracellular matrices. It is found in fungal septa, spores, and cell walls, and in arthropod cuticles and peritrophic matrices, squid pens, mollusk shells, nematode egg shells, and some protozoan cyst walls. As prokaryotes, plants and vertebrates including humans do not produce chitin, its synthesis is considered as an attractive target site for fungicides, insecticides, and acaricides. Although no chitin synthesis inhibitor has been developed into a therapeutic drug to treat fungal infections in humans, a larger number of compounds have been successfully launched worldwide to combat arthropod pests in agriculture and forestry. This review summarizes the latest advances on the mode of action of chitin synthesis inhibitors with a special focus on those molecules that act on a postcatalytic step of chitin synthesis.

Design and synthesis of chitin synthase inhibitors as potent fungicides

Chitin is a structural component of fungal cell walls but is absent in vertebrates,mammals,and humans.Chitin synthase is thus an attractive molecular target for developing fungicides.Based on the structure of its donor substrate,UDP-N-acetyl-glucosamine,as well as the modelled structure of the bacterial chitin synthase NodC,we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors.The most potent inhibitor,compound 13,exhibited high chitin synthase inhibitory activity with an IC（50） value of 64.5 μmol/L All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi,Fusarium graminearum,Botrytis cinerea.and Colletotrichum lagenarium.This work presents a new scaffold which can be used for the development of novel fungicides.