Synthesis, crystal structure, bioactivity and DFT calculation of new oxime ester derivatives containing cyclopropane moiety

被引：102

作者：

Liu, Xing-Hai ^{[1
]}

Pan, Li ^{[2
]}

Tan, Cheng-Xia ^{[1
]}

Weng, Jian-Quan ^{[1
]}

Wang, Bao-Lei ^{[2
]}

Li, Zheng-Ming ^{[2
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China

[2] Nankai Univ, Natl Pesticidal Engn Ctr Tianjin, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY | 2011年 / 101卷 / 03期

关键词：

Cyclopropane; Oxime ester; Transit structure; KARI activity; Herbicidal activity; KETOL-ACID REDUCTOISOMERASE; INHIBITOR;

D O I：

10.1016/j.pestbp.2011.08.006

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new series of oxime esters containing cyclopropane moiety were designed and synthesized. Their structures were confirmed by H-1 NMR, MS and elemental analysis. The single crystal structure of compound 7b was determined to further elucidate the structure. The KARI activity indicated that compound 7k exhibits favorable inhibition rate: the herbicidal assay showed that most of them have moderate activity against Echinochloa frumentacea, some of which have moderate activity against Brassica campestris. (C) 2011 Elsevier Inc. All rights reserved.

引用

页码：143 / 147

页数：5

共 21 条

[1] OXALYL HYDROXAMATES AS REACTION-INTERMEDIATE ANALOGS FOR KETOL-ACID REDUCTOISOMERASE [J].

AULABAUGH, A ;

SCHLOSS, JV .

BIOCHEMISTRY, 1990, 29 (11) :2824-2830

[2] ACETOLACTATE SYNTHASE IS THE SITE OF ACTION OF 2 SULFONYLUREA HERBICIDES IN HIGHER-PLANTS [J].

CHALEFF, RS ;

MAUVAIS, CJ .

SCIENCE, 1984, 224 (4656) :1443-1445

[3] MECHANISM OF KETOL ACID REDUCTOISOMERASE - STEADY-STATE ANALYSIS AND METAL-ION REQUIREMENT [J].

CHUNDURU, SK ;

MRACHKO, GT ;

CALVO, KC .

BIOCHEMISTRY, 1989, 28 (02) :486-493

[4]

Duggleby RG, 2000, J BIOCHEM MOL BIOL, V33, P1

[5]

Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[6] RAPID DIAGNOSIS OF ALS AHAS-RESISTANT WEEDS [J].

GERWICK, BC ;

MIRELES, LC ;

EILERS, RJ .

WEED TECHNOLOGY, 1993, 7 (02) :519-524

[7] Kinetic and mass spectrometric analyses of the interactions between plant acetohydroxy acid isomeroreductase and thiadiazole derivatives [J].

Halgand, F ;

Vives, F ;

Dumas, R ;

Biou, V ;

Andersen, J ;

Andrieu, JP ;

Cantegril, R ;

Gagnon, J ;

Douce, R ;

Forest, E ;

Job, D .

BIOCHEMISTRY, 1998, 37 (14) :4773-4781

[8]

HUNG S, 1983, IND CHEM, V11, P291

[9] CHEMISTRY OF AMINE-BORANES .5. REDUCTION OF OXIMES, O-ACYL-OXIMES, AND O-ALKYL-OXIMES WITH PYRIDINE-BORANE IN ACID [J].

KAWASE, M ;

KIKUGAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03) :643-645

[10]

Koo SJ, 1997, PESTIC SCI, V51, P109, DOI 10.1002/(SICI)1096-9063(199710)51:2<109::AID-PS585>3.0.CO

← 1 2 3 →