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1.
Pest Manag Sci ; 71(3): 404-14, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-24777582

RESUMO

BACKGROUND: Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with broad spectrum and high activity, a series of novel oxime ether strobilurin derivatives containing substituted benzofurans in the side chain were synthesised and bioassayed. RESULTS: The synthesised compounds were characterised by (1) H NMR, (13) C NMR, MS and HRMS. Bioassays demonstrated that most target compounds possessed good or excellent fungicidal activities, especially against Erysiphe graminis and Pyricularia oryzae. Furthermore, methyl 3-methoxypropenoate oxime ethers exhibited remarkably higher activities against E. graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. Notably, (E,E)-methyl 3-methoxy-2-{2-[({[5-fluoro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF2) and (E,E)-methyl 3-methoxy-2-{2-[({[5-chloro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF3) were identified as the most promising candidates for further study. CONCLUSION: The present work demonstrates that oxime ether strobilurin derivatives containing benzofurans can be used as possible lead compounds for developing novel fungicides.


Assuntos
Fungos/efeitos dos fármacos , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Ácidos Graxos Insaturados/síntese química , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/farmacologia , Fungicidas Industriais/farmacologia , Espectroscopia de Ressonância Magnética , Metacrilatos/síntese química , Metacrilatos/química , Metacrilatos/farmacologia , Oximas/síntese química , Oximas/química , Oximas/farmacologia , Relação Estrutura-Atividade
2.
Chem Biol Drug Des ; 85(6): 743-55, 2015 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-25346294

RESUMO

Twenty-one novel oxime ether strobilurins containing indole moiety, which employed an indole group to stabilize the E-styryl group in Enoxastrobin, were designed and synthesized. The biological assay indicated that most compounds exhibited potent fungicidal activities. The structure-activity relationship study demonstrated that the synthesized methyl 3-methoxypropenoate oxime ethers 7b-e exhibited remarkably high activities among all the synthesized oxime ether compounds 7. Moreover, the fungicidal activities of methyl α-(methoxyimino)benzeneacetate oxime ethers compounds 7f-i and N-methoxy-carbamic acid methyl esters compounds 7j-m showed significant differences compared to the corresponding products of ammonolysis.


Assuntos
Fungos/efeitos dos fármacos , Fungicidas Industriais/química , Indóis/química , Oximas/química , Éteres/síntese química , Éteres/química , Éteres/farmacologia , Ácidos Graxos Insaturados/síntese química , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/farmacologia , Fungicidas Industriais/síntese química , Fungicidas Industriais/farmacologia , Indóis/síntese química , Indóis/farmacologia , Metacrilatos/síntese química , Metacrilatos/química , Metacrilatos/farmacologia , Oximas/síntese química , Oximas/farmacologia , Estrobilurinas , Relação Estrutura-Atividade
3.
Bioorg Med Chem Lett ; 24(9): 2173-6, 2014 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-24717155

RESUMO

Twenty-one novel benzothiophene-substituted oxime ether strobilurins, which employed a benzothiophene group to stabilise the E-styryl group in Enoxastrobin (an unsaturated oxime strobilurin fungicide developed by Shenyang Research Institute of Chemical Industry, China) were designed and synthesised. The biological assay indicated that most compounds exhibited good or excellent fungicidal activities, especially against Colletotrichum lagenarium and Puccinia sorghi Schw. In addition, methyl 3-methoxypropenoate oxime ethers and N-methoxy-carbamic acid methyl esters exhibited good in vivo fungicidal activities against Erysiphe graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. under the tested concentrations. Notably, (E,E)-methyl 3-methoxy-2-(2-((((6-chloro-1-(1H-benzo[b]thien-2-yl)ethylidene)amino)oxy)methyl)phenyl)propenoate (5E) exhibited more potent in vivo fungicidal activities against nearly all of the tested fungi at a concentration of 0.39 mg/L compared to Enoxastrobin.


Assuntos
Fungos/efeitos dos fármacos , Fungicidas Industriais/química , Fungicidas Industriais/toxicidade , Tiofenos/química , Tiofenos/toxicidade , Ácidos Graxos Insaturados/síntese química , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/toxicidade , Fungicidas Industriais/síntese química , Metacrilatos/síntese química , Metacrilatos/química , Metacrilatos/toxicidade , Oximas/síntese química , Oximas/química , Oximas/toxicidade , Estrobilurinas , Tiofenos/síntese química
4.
J Nat Prod ; 75(10): 1810-3, 2012 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-23075087

RESUMO

The roots of Polygonum cuspidatum produce several phenolic compounds, including trans-resveratrol (1), trans-piceid (2), and emodin (3), and are a commercial source of the botanical dietary supplement 1. Ultrasonic-assisted extraction technology and conventional shaking extraction procedures were compared for the extraction of 1-3 from P. cuspidatum roots, using 50% ethanol as a food grade solvent. These compounds were extracted successfully, and their mass transfer coefficients were calculated by fitting the experimental results to a model derived from Fick's second law. The results indicated that ultrasonic-assisted extraction had higher mass transfer efficacies and extraction yields for 1-3 as compared with conventional shaking extraction. Under the extraction conditions used (extraction temperature 50 °C; ultrasonic power 150 W), yields of 3.5, 9.2, and 7.8 mg/g were obtained for 1-3, respectively.


Assuntos
Fallopia japonica/química , Estilbenos/química , Estilbenos/farmacologia , Ultrassom/métodos , Suplementos Nutricionais , Espectroscopia de Ressonância de Spin Eletrônica , Modelos Químicos , Estrutura Molecular , Raízes de Plantas/química , Resveratrol , Estereoisomerismo , Estilbenos/isolamento & purificação , Taiwan
5.
J Agric Food Chem ; 56(13): 5247-53, 2008 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-18547049

RESUMO

Nineteen novel indene-substituted oxime ether strobilurins, which used an indene group to stabilize the ( E)-styryl group in SYP-Z071 (an unsaturated oxime strobilurin fungicide under development by the Shenyang Research Institute of Chemical Industry), were designed and synthesized. The biological assay results showed that all compounds possessed good or excellent fungicidal activities. It was found that most of the compounds showed higher fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Erysiphe graminis, and Colletotrichum lagenarium than SYP-Z071 at the tested concentration. The biological assay results also indicated that most of the compounds exhibited higher in vivo fungicidal activities against cucumber Pseudoperonospora cubensis and C. lagenarium than the commercial fungicides trifloxystrobin and kresoxim-methyl at a concentration of 6.25 mg/L. Furthermore, it was found that alpha-(methoxyimino)- N-methylphenylacetamide oxime ethers 6m- s exhibited a broad spectrum and remarkably higher activities against all tested fungi. Especially, the 6-methylindene-substituted compound 6p was identified as the most promising candidate for further study.


Assuntos
Acrilatos/síntese química , Acrilatos/farmacologia , Fungos/efeitos dos fármacos , Fungicidas Industriais/síntese química , Fungicidas Industriais/farmacologia , Acrilatos/química , Éteres , Fungicidas Industriais/química , Indenos/síntese química , Indenos/química , Indenos/farmacologia , Estrutura Molecular , Oximas/síntese química , Oximas/química , Oximas/farmacologia , Relação Estrutura-Atividade
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