Synthesis and Biological Activity of O-Methyl Methyl 1-(Substituted Phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates

被引：3
作者：
Wang, Tao
Peng, Hao
He, Hongwu [1 ]
机构：
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan, Peoples R China
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2015年 / 52卷 / 04期
基金：
国家科技攻关计划; 中国国家自然科学基金;
关键词：
HERBICIDAL ACTIVITY; PYRUVATE-DEHYDROGENASE; DESIGN; BIOSYNTHESIS; DERIVATIVES; INHIBITORS; PYRIDINE; ANALOGS;
D O I：
10.1002/jhet.2143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of novel O-methyl methyl 1-(substituted phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates 5a-h were synthesized. Their structures were confirmed by IR, H-1 NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 5c, 5d, and 5g possess 90-100% inhibition against the tested plants at the concentration of 10 mg/L and 100 mg/L, whereas the title compounds 5a, 5b, 5c, and 5h possess 70-94% inhibition against Phyricularia grisea and Sclerotinia sclerotiorum at the concentration of 50 mg/L.
引用
收藏
页码：1260 / 1263
页数：4
相关论文
共 17 条
[1]   Studies with S-alkylpyrimidine:: New route for the synthesis derivatives of isoxazol, pyrazolo[1,5-a]pyrimidine, pyridazine, pyridine, thieno[2,3-b]pyridine and thiophene of potential anti-HIV [J].
Al-Omran, Fatima A. ;
El-Khair, Adel A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) :1057-1063
[2]  
Burger A., 1991, Progress in Drug Research, V37, P288
[3]   Synthesis and herbicidal activity of O,O-dialkyl phenoxyacetoxyalkylphosphonates containing fluorine [J].
Chen, T ;
Shen, P ;
Li, YJ ;
He, HW .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (02) :291-295
[4]   Rational herbicide design by inhibition of tryptophan biosynthesis [J].
Finn, J ;
Langevine, C ;
Birk, I ;
Birk, J ;
Nickerson, K ;
Rodaway, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2297-2302
[5]   Synthesis and Herbicidal Activities of 2-Methylpropan-2-Aminium Methyl 1-(Substituted Phenoxyacetoxy) Alkylphosphonates [J].
Gao, Ling ;
Deng, Xiaoyan ;
Tan, Xiaosong ;
Long, Qingwu ;
Peng, Hao ;
He, Hongwu .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (08) :989-994
[6]   Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall [J].
Gobec, Stanislav ;
Plantan, Ivan ;
Mravljak, Janez ;
Svajger, Urban ;
Wilson, Rosalind A. ;
Besra, Gurdyal S. ;
Soares, Sousana L. ;
Appelberg, Rui ;
Kikelj, Danijel .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (01) :54-63
[7]   Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a New Herbicide. 1. Synthesis and Herbicidal Activity of HW02 and Analogues as Novel Inhibitors of Pyruvate Dehydrogenase Complex [J].
He, Hong-Wu ;
Yuan, Jun-Lin ;
Peng, Hao ;
Chen, Ting ;
Shen, Ping ;
Wan, Shu-Qing ;
Li, Yanjun ;
Tan, Hong-Liang ;
He, Ya-Hui ;
He, Jun-Bo ;
Li, Yan .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (09) :4801-4813
[8]   Synthesis and herbicidal activity of alkyl 1-(3-trifluoromethylphenoxyacetoxy)-1-substituted methylphosphonates [J].
He, Hongwu ;
Chen, Ting ;
Li, Yanjun .
JOURNAL OF PESTICIDE SCIENCE, 2007, 32 (01) :42-44
[9]   Design, synthesis, and antiviral activity of adenosine 5′-phosphonate analogues as chain terminators against hepatitis C virus [J].
Koh, YH ;
Shim, JH ;
Wu, JZ ;
Zhong, WD ;
Hong, Z ;
Girardet, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (08) :2867-2875
[10]   Synthesis and herbicidal activity of novel 3-aminocarbonyl-2-oxazolidinethione derivatives containing a substituted pyridine ring [J].
Li, GY ;
Qian, XH ;
Cui, JN ;
Huang, QC ;
Zhang, R ;
Guan, H .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (01) :125-129
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