title: Degradation of the novel herbicide ZJ0273 by Amycolatopsis sp. M3-1 isolated from soil.
abstract: ZJ0273, propyl 4-(2-(4,6-dimethoxypyrimidin-2-yloxy) benzylamino) benzoate, is a novel and broad-spectrum herbicide. In this study, 15 bacteria capable of utilizing ZJ0273 as the sole carbon source were isolated from soil. One of the isolates belonged to the family Amycolatopsis and was designated to Amycolatopsis sp. M3-1; at 30°C and pH 7.0, degradation rate of ZJ0273 could reach at 59.3% and 68.5% in 25 days and 60 days, respectively. Furthermore, six metabolites (M1-M6) during the degradation of ZJ0273 by Amycolatopsis sp. M3-1 were identified by a combination with multi-position (14)C-labeled compounds (B-ZJ0273 and C-ZJ0273), chromatography, liquid scintillation spectrometer, and LC-MS, a novel pathway of ZJ0273 degradation by Amycolatopsis sp. M3-1 was proposed based on the identified metabolites and their biodegradation courses. ZJ0273 was initially hydrolyzed into M1 (4-(2-(4,6-dimethoxypyrimidin-2-yloxy) benzylamino) benzoic acid), then further oxidized into M3 (2-(4,6-dimethoxypyrimidin-2-yloxy) benzoic acid). M1 also could undergo a carbonylation into M2 (4-(2-(4,6-dimethoxypyrimidin-2-yloxy) benzamido) benzoic acid), and then its C-N and C-O bonds were cleaved to yield M3 (2-(4,6-dimethoxypyrimidin-2-yloxy) benzoic acid) and M4 (4,6-dimethoxypyrimidin-2-ol), respectively. Moreover, another two new metabolites, M5 (2-(4-hydroxy, 6-methoxypyrimidin-2-yloxy) benzoic acid) and M6 (2, 4-dihydroxy-pyrimidine) were found. M5 was formed through de-methyl of M3 and then hydrolyzed into M6.
authors.affiliation: Institute of Nuclear Agricultural Sciences, Key Laboratory of Nuclear Agricultural Sciences of the Ministry of Agriculture, Zhejiang University, Hangzhou, 310029, China. zhqcai@yahoo.com
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Cai
authors.forename: Qiaoli
authors.initials: Q
authors.lastname: Chen
authors.forename: Haiyan
authors.initials: H
authors.lastname: Wang
authors.forename: Yucai
authors.initials: Y
authors.lastname: He
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Xiyue
authors.initials: X
authors.lastname: Zhao
authors.forename: Qingfu
authors.initials: Q
authors.lastname: Ye
mesh_terms: D000192:Actinomycetales / Q000145:classification / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism*; D001565:Benzoates / Q000378:metabolism*; D002250:Carbon Radioisotopes / Q000378:metabolism; D002845:Chromatography; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D006540:Herbicides / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D007553:Isotope Labeling; D053858:Metabolic Networks and Pathways; D008969:Molecular Sequence Data; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D017422:Sequence Analysis, DNA; D012988:Soil Microbiology; D013057:Spectrum Analysis; D013696:Temperature
chemical_list: D001565:Benzoates; D002250:Carbon Radioisotopes; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D006540:Herbicides; D012336:RNA, Ribosomal, 16S; C543844:propyl 4-(2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino)benzoate