Synthesis and antifungal activity of 2-allylphenol derivatives against fungal plant pathogens. 2017

Tianli Qu, and Shumei Gao, and Jianqiang Li, and Jianjun J Hao, and Pingsheng Ji
Chemistry and Pharmacy College, Qingdao Agricultural University, Shandong 266109, China; Department of Plant Pathology, Coastal Plain Experiment Station, University of Georgia, Tifton, GA 31794, USA.

2-Allylphenol (2-AP) is an effective fungicide against a number of plant pathogens, which can be metabolized and bio-transformed to four chemical compounds by Rhizoctonia cerealis. To determine if its degradation affects antifungal activity, two major metabolites derived from 2-AP including 2-(2-hydroxypropyl) phenol and 2-(3-hydroxypropyl) phenol were synthesized. Inhibition of mycelial growth of several plant pathogens by the metabolites was evaluated, and structures of two metabolites were determined by hydrogen nuclear magnetic resonance (1H NMR). Among these metabolites, only 2-(2-hydroxypropyl) phenol inhibited test pathogens effectively. EC50 values of 2-(2-hydroxypropyl) phenol for inhibition of mycelial growth of R. cerealis, Pythium aphanidermatum, Valsa mali and Botrytis cinerea ranged from 1.0 to 23.5μg/ml, which were lower than the parental fungicide 2-AP that ranged from 8.2 to 48.8μg/ml. Hyphae of R. cerealis and P. aphanidermatum treated with 2-(2-hydroxypropyl) phenol were twisted. Newly developed hyphae were slender, twisted and swollen on the tip, while old hyphae were hollow and ruptured. This is the first report indicating the formation of 2-(2-hydroxypropyl) phenol may have contributed to toxicity of 2-allylphenol in control of plant pathogens.

UI MeSH Term Description Entries
D010636 Phenols Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D010935 Plant Diseases Diseases of plants. Disease, Plant,Diseases, Plant,Plant Disease
D011775 Pythium A genus of destructive root-parasitic OOMYCETES in the family Pythiaceae, order Peronosporales, commonly found in cultivated soils all over the world. Differentiation of zoospores takes place in a vesicle. Pythiums
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D001203 Ascomycota A phylum of fungi which have cross-walls or septa in the mycelium. The perfect state is characterized by the formation of a saclike cell (ascus) containing ascospores. Most pathogenic fungi with a known perfect state belong to this phylum. Ascomycetes,Cochliobolus,Sclerotinia,Ascomycete,Ascomycotas,Sclerotinias
D012232 Rhizoctonia A mitosporic Ceratobasidiaceae fungal genus that is an important plant pathogen affecting potatoes and other plants. There are numerous teleomorphs. Rhizoctonias
D020171 Botrytis A mitosporic Leotiales fungal genus of plant pathogens. It has teleomorphs in the genus Botryotina. Botryti
D025282 Mycelium The body of a fungus which is made up of HYPHAE. Myceliums
D025301 Hyphae Microscopic threadlike filaments in FUNGI that are filled with a layer of protoplasm. Collectively, the hyphae make up the MYCELIUM. Hypha,Hyphas

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