Synthesis and fungicidal activities of novel benzothiophene-substituted oxime ether strobilurins.
Twenty-one novel benzothiophene-substituted oxime ether strobilurins, which employed a benzothiophene group to stabilise the E-styryl group in Enoxastrobin (an unsaturated oxime strobilurin fungicide developed by Shenyang Research Institute of Chemical Industry, China) were designed and synthesised. The biological assay indicated that most compounds exhibited good or excellent fungicidal activities, especially against Colletotrichum lagenarium and Puccinia sorghi Schw. In addition, methyl 3-methoxypropenoate oxime ethers and N-methoxy-carbamic acid methyl esters exhibited good in vivo fungicidal activities against Erysiphe graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. under the tested concentrations. Notably, (E,E)-methyl 3-methoxy-2-(2-((((6-chloro-1-(1H-benzo[b]thien-2-yl)ethylidene)amino)oxy)methyl)phenyl)propenoate (5E) exhibited more potent in vivo fungicidal activities against nearly all of the tested fungi at a concentration of 0.39 mg/L compared to Enoxastrobin.
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China. Electronic address: tusong@xmu.edu.cn.
Song
S
Tu
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Ya-Qiang
YQ
Xie
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Si-Zhe
SZ
Gui
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Li-Yi
LY
Ye
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Zi-Long
ZL
Huang
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Yi-Bing
YB
Huang
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
Li-Ming
LM
Che
D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D008689:Methacrylates / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D000073739:Strobilurins; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*
D005231:Fatty Acids, Unsaturated; D005659:Fungicides, Industrial; D008689:Methacrylates; D010091:Oximes; D000073739:Strobilurins; D013876:Thiophenes; C088015:benzothiophene; C008556:mucidin
Benzothiophene; Fungicidal activities; Fungicide; Oxime ether; Strobilurins