Synthesis and fungicidal activities of novel bis(trifluoromethyl)phenyl-based strobilurins.
Strobilurins have become one of the most important classes of agricultural fungicides. To search for novel strobilurin compounds with unique biological activities, novel bis(trifluoromethyl)phenyl-based strobilurin analogues were synthesized by the reaction of 1-bis(trifluoromethyl)phenyl based methanone oxime with corresponding strobilurin pharmacophores in the presence of bases such as potassium hydroxide, potassium carbonate, or sodium hydride. ( E)-Methyl 2-(2-(((( Z)(1-(3,5-bis(trifluoromethyl) phenyl)-1-methoxymethylidene)amino)oxy)methyl)phenyl)-3-methoxyacrylate and ( Z)-methyl- N-( E)-2-(( E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(methoxyimino)methyl)benzyloxy-3,5-bis(trifluoromethyl)benzimidate were more effective against Erysiphe graminis and sphaerotheca fuligine than commercial strobilurin fungicides metominostrobin, azoxystrobin, and trifloxystrobin.
Liu
Aiping
A
National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, China. lapliu@yahoo.com
Wang
Xiaoguang
X
Ou
Xiaoming
X
Huang
Mingzhi
M
Chen
Can
C
Liu
Shudong
S
Huang
Lu
L
Liu
Xinping
X
Zhang
Chenglai
C
Zheng
Yongquan
Y
Ren
Yeguo
Y
He
Lian
L
Yao
Jianren
J
D001203:Ascomycota / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D008689:Methacrylates / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D005659:Fungicides, Industrial; D008689:Methacrylates