title: Metabolism of fungicide 2-allylphenol in Rhizoctonia cerealis.
abstract: 2-Allylphenol is a biomimetic synthetic fungicide that mimics the compound ginkgol found in gingko fruit (Gingko biloba L.). This systemic fungicide can effectively suppress a wide range of plant diseases, including wheat sharp eyespot (Rhizoctonia cerealis). However, its degradation in environment after application is still unknown. To understand this fungicide degradation, major metabolites of 2-allylphenol in R. cerealis were examined. The parent and metabolites of 2-allylphenol were detected and quantified in the mycelia and liquid medium. Results showed that 2-allylphenol was metabolized and bio-transformed by R. cerealis, and four metabolites were found, including 2-(2-hydroxyphenyl) acetic acid (M1), 2-(2, 3-dihydroxypropyl) phenol (M2), 2-(2-hydroxypropyl)-phenol (M3) and 2-(3-hydroxypropyl)-phenol (M4). Based on the results, we propose that the biodegradation pathway is that 2-allylphenol is rapidly oxidized into metabolite M2 and hydrolyzed into M3 and M4, which formed M2, and carboxylation of M2 to 2-hydroxy-3-(2׳-hydroxyphenyl) propionic acid which undergo hydrolyzation and decarboxylation to form M1. 2-Allylphenol can be bio-transformed to new compounds by R. cerealis, suggesting the existence of microbe metabolic pathways for 2-allylphenol.
authors: Chemistry and Pharmacy College, Qingdao Agricultural University, Shandong 266109, China.
authors: Tianli
authors: T
authors: Qu
authors: Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors: Jinlan
authors: J
authors: Zhang
authors: Chemistry and Pharmacy College, Qingdao Agricultural University, Shandong 266109, China.
authors: Zhaoli
authors: Z
authors: Meng
authors: Department of Plant Pathology, China Agricultural University, Beijing 100193, China.
authors: Xili
authors: X
authors: Liu
authors: Department of Plant Pathology, China Agricultural University, Beijing 100193, China.
authors: Yongsong
authors: Y
authors: Cao
authors: Department of Plant Pathology, China Agricultural University, Beijing 100193, China. Electronic address: lijq231@cau.edu.cn.
authors: Jianqiang
authors: J
authors: Li
authors: Department of Plant, Soil, and Microbial Sciences, Michigan State University, East Lansing, MI 48824, USA.
authors: Jianjun J
authors: JJ
authors: Hao
mesh_terms: D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D004785:Environmental Pollutants / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D005659:Fungicides, Industrial / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D012232:Rhizoctonia / Q000378:metabolism*; D053719:Tandem Mass Spectrometry
chemical_list: D004785:Environmental Pollutants; D005659:Fungicides, Industrial; D010636:Phenols; C099328:2-allylphenol
keywords: 2-Allylphenol; Metabolites; Rhizoctonia cerealis