Open AccessBioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection
Author(s) -
Kun Zhou,
Dongdong Chen,
Bin Li,
Bingyu Zhang,
Fei Miao,
Le Zhou
Publication year - 2017
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0176189
Subject(s) - cinnamic acid , fungicide , moiety , carbendazim , ec50 , mycelium , chemistry , structure–activity relationship , stereochemistry , alcohol , antifungal , organic chemistry , biology , biochemistry , in vitro , botany , microbiology and biotechnology
A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure−activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC 50 values of 17.4–28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P . grisea or kresoxim-methyl against both P . grisea and Valsa mali . Compounds C1 and C2 showed the higher activity with average EC 50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure−activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.