Efficient synthesis of fused bicyclic ethers and their application in herbicide chemistry

被引：22

作者：

Schaetzer, Juergen ^{[1
]}

Edmunds, Andrew J. F. ^{[1
]}

Gaus, Katharina ^{[1
]}

Rendine, Stefano ^{[1
]}

De Mesmaeker, Alain ^{[1
]}

Rueegg, Willy ^{[2
]}

机构：

[1] Syngenta Crop Protect Muenchwilen AG, CH-4322 Stein, Switzerland

[2] Syngenta Crop Protect AG, CH-4058 Basel, Switzerland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 19期

关键词：

Benzoylcyclohexanedione; Triketone herbicide; 4-Hydroxyphenylpyruvate dioxygenase (HPPD); Structure-activity relationship (SAR); P-HYDROXYPHENYLPYRUVATE DIOXYGENASE; RING-CLOSING METATHESIS; 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; CLAISEN REARRANGEMENT; SELECTIVE HERBICIDE; OLEFIN METATHESIS; ISOXAFLUTOLE; INHIBITORS; DISCOVERY; LACTONE;

D O I：

10.1016/j.bmcl.2014.08.043

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of triketones 2 and 3 featuring novel fused bicyclic aryl ethers have been prepared. The syntheses utilized ring-closing olefin metathesis (compounds 2), or oxidative cyclization of allylphenols as the key steps. The herbicidal activity of the targeted triketones 2 and 3 on various grasses and broad-leaved weeds was determined and compared with compound 1. The strength of the novel compounds 2 and 3 is their good herbicidal activity on broad-leaved weeds in post-emergent applications, whereas activity on grasses was inferior compared to 1. In addition, computational methods have been applied to provide a deeper understanding of the SAR found for compounds 2 and 3. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4643 / 4649

页数：7

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