Synthesis and Herbicidal Activity of Diphenyl Ether Derivatives Containing Unsaturated Carboxylates

被引:27
作者
Yu, Haibo [1 ]
Yang, Huibin [1 ]
Gui, Dongliang [1 ]
Lv, Liang [1 ]
Li, Bin [1 ]
机构
[1] Shenyang Res Inst Chem Ind Co Ltd, State Key Lab Discovery & Dev Novel Pesticide, Shenyang 110021, Peoples R China
关键词
Protoporphyrinogen oxidase; diphenyl ether; unsaturated carboxylate; synthesis; herbicide; PROTOPORPHYRINOGEN OXIDASE-INHIBITORS; OXIDIZING ACTIVITIES; ETHYL; MECHANISM; DESIGN; MODE;
D O I
10.1021/jf2039444
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
A series of novel diphenyl ether derivatives containing unsaturated carboxylates were designed and synthesized Their structures were identified by H-1 nuclear magnetic resonance and elemental analyses The bioassays indicated that the compounds 5b and 5c exhibited good herbicidal activities against velvetleaf at a concentration of 30-40 g/hm(2) The relationship between structure and herbicidal activity was also discussed Among unsaturated carboxylates group; butenoate is the most promising one Amonst them, 4-ethoxy-4-oxobutenyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate 5b was identified as the most promising candidate due to its high protoporphyrinogen IX oxidase inhibition effect (pI(50) = 6 64) and good herbicidal activity against broadleaf weeds with selectivity to soybean and low toxicity to mammals
引用
收藏
页码:11718 / 11726
页数:9
相关论文
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[31]   Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors [J].
Zhang, Li ;
Tan, Yin ;
Wang, Neng-Xue ;
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Yang, Guang-Fu .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (22) :7948-7956