5-(4-羟苄基)-2-硫代亚氨代二氢-4(3H)-酮酯的合成与除草活性。
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
机构信息
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
出版信息
Molecules. 2011 Mar 30;16(4):2833-45. doi: 10.3390/molecules16042833.
Abstract
A series of novel 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters were synthesized under mild conditions by the reaction of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one and carboxylic acids with DCC and DMAP as the promoters. Their structures were confirmed by ¹H-NMR, IR, ESI-MS and elemental analysis. The preliminary bioassy results indicated that some of compounds exhibit good herbicidal activity against Zea mays, Triticum aestivum and Arabidopsis thaliana. The further greenhouse test showed that compounds 6-16 and 6-28 have 60%, 50% and 50% efficacy against Stellaria media, Echinochloa crus-galli and Setaria viridis at 1,000 g/ha, respectively.
摘要
一系列新型 5-(4-羟苄基)-2-硫代-咪唑烷-4-酮酯在温和条件下通过 5-(4-羟苄基)-2-硫代-咪唑烷-4-酮和羧酸与 DCC 和 DMAP 作为促进剂的反应合成。它们的结构通过 1H-NMR、IR、ESI-MS 和元素分析得到确认。初步的生物测定结果表明，一些化合物对玉米、小麦和拟南芥具有良好的除草活性。进一步的温室试验表明，化合物 6-16 和 6-28 在 1,000 g/ha 下对繁缕、稗草和马唐的防治效果分别为 60%、50%和 50%。
相似文献
1
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
Molecules. 2011 Mar 30;16(4):2833-45. doi: 10.3390/molecules16042833.
2
Synthesis and herbicidal activity of novel 1-(Diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl carboxylic esters.
Molecules. 2015 Jan 12;20(1):1088-103. doi: 10.3390/molecules20011088.
3
Synthesis and herbicidal activity of isoindoline-1,3-dione substituted benzoxazinone derivatives containing a carboxylic ester group.
J Agric Food Chem. 2009 Oct 28;57(20):9585-92. doi: 10.1021/jf901897f.
4
Design, synthesis, and herbicidal activities of novel 2-cyanoacrylates containing isoxazole moieties.
J Agric Food Chem. 2010 Mar 10;58(5):2685-9. doi: 10.1021/jf902541w.
5
Synthesis and herbicidal activity of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties.
Bioorg Med Chem Lett. 2007 Apr 15;17(8):2203-9. doi: 10.1016/j.bmcl.2007.01.083. Epub 2007 Feb 1.
6
Synthesis and herbicidal activity of novel N-(2,2,2)-trifluoroethylpyrazole derivatives.
J Agric Food Chem. 2010 Apr 14;58(7):4356-60. doi: 10.1021/jf9042166.
7
Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one.
J Agric Food Chem. 2012 Aug 8;60(31):7581-7. doi: 10.1021/jf301829m. Epub 2012 Jul 30.
8
Synthesis and herbicidal activity of novel alpha,alpha,alpha-trifluoro-m-tolyl pyridazinone derivatives.
Pest Manag Sci. 2006 Jun;62(6):522-30. doi: 10.1002/ps.1195.
9
A bleaching herbicidal activity of methoxyhygromycin (MHM) produced by an actinomycete strain Streptomyces sp. 8E-12.
Lett Appl Microbiol. 2003;36(6):387-91. doi: 10.1046/j.1472-765x.2003.01327.x.
10
Synthesis, structure and biological activity of novel 1,2,4-triazole mannich bases containing a substituted benzylpiperazine moiety.
Chem Biol Drug Des. 2011 Jul;78(1):42-9. doi: 10.1111/j.1747-0285.2011.01132.x. Epub 2011 May 31.
引用本文的文献
1
Exploration of newly synthesized azo-thiohydantoins as the potential alkaline phosphatase inhibitors via advanced biochemical characterization and molecular modeling approaches.
BMC Chem. 2024 Mar 6;18(1):47. doi: 10.1186/s13065-024-01149-8.
2
1-Benzyl-3-aryl-2-thiohydantoin Derivatives as New Anti- Agents: SAR and in Vivo Efficacy.
ACS Med Chem Lett. 2017 Jul 10;8(8):886-891. doi: 10.1021/acsmedchemlett.7b00230. eCollection 2017 Aug 10.
3
Synthesis and activity of novel acylthiourea with hydantoin.
Int J Mol Sci. 2013 Sep 26;14(10):19526-39. doi: 10.3390/ijms141019526.
4
Facile synthesis of 5-arylidene thiohydantoin by sequential sulfonylation/desulfination reaction.
Int J Mol Sci. 2013 Jun 13;14(6):12484-95. doi: 10.3390/ijms140612484.
5
A practical approach to new (5Z) 2-alkylthio-5-arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one derivatives.
Molecules. 2011 Aug 30;16(9):7377-90. doi: 10.3390/molecules16097377.
本文引用的文献
1
A simple synthesis of 2-thiohydantoins.
Molecules. 2006 Oct 2;11(10):739-50. doi: 10.3390/11100739.
2
Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3 + 2]-cycloadditions to 5-methylenehydantoins.
J Org Chem. 2005 Aug 5;70(16):6369-77. doi: 10.1021/jo050827h.
3
Tiplaxtinin, a novel, orally efficacious inhibitor of plasminogen activator inhibitor-1: design, synthesis, and preclinical characterization.
J Med Chem. 2004 Jul 1;47(14):3491-4. doi: 10.1021/jm049766q.
4
Synthesis and properties of spiro nucleosides containing the barbituric acid moiety.
J Org Chem. 2002 Feb 22;67(4):1302-7. doi: 10.1021/jo016194y.
5
A potent aldose reductase inhibitor, (2S,4S)-6-fluoro-2', 5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (Fidarestat): its absolute configuration and interactions with the aldose reductase by X-ray crystallography.
J Med Chem. 2000 Jun 15;43(12):2479-83. doi: 10.1021/jm990502r.
6
Adenylosuccinate synthetase from maize. Purification, properties, and mechanism of inhibition by 5'-phosphohydantocidin.
Plant Physiol. 1997 Jun;114(2):549-55. doi: 10.1104/pp.114.2.549.
7
Refined crystal structure of adenylosuccinate synthetase from Escherichia coli complexed with hydantocidin 5'-phosphate, GDP, HPO4(2-), Mg2+, and hadacidin.
Biochemistry. 1996 Dec 10;35(49):15753-9. doi: 10.1021/bi961758r.
8
Adenylosuccinate synthetase: site of action of hydantocidin, a microbial phytotoxin.
Plant Physiol. 1996 Mar;110(3):753-8. doi: 10.1104/pp.110.3.753.
9
The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.
Proc Natl Acad Sci U S A. 1996 Sep 3;93(18):9431-6. doi: 10.1073/pnas.93.18.9431.
10
S-glucosylated hydantoins as new antiviral agents.
J Med Chem. 1994 Jan 7;37(1):73-7. doi: 10.1021/jm00027a009.
Zotero 插件