Synthesis and herbicidal activity of 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy) carbonyl]-5-cyano-6-[(3-trifluoromethyl)phenoxy]-pyridines

Zhai Y.-E.; Shi D.-Q.

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Synthesis and herbicidal activity of 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy) carbonyl]-5-cyano-6-[(3-trifluoromethyl)phenoxy]-pyridines

机译：2-烷基（芳基）-4-氨基-3- [烷基（烷氧基）羰基] -5-氰基-6-[（3-三氟甲基）苯氧基]-吡啶的合成及除草活性

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To find novel bleaching herbicide lead compounds, a series of novel 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy)carbonyl]-5-cyano-6-[(3-trifluoromethyl) phenoxy]-pyridines was designed and synthesized by the multistep reactions. N,S-acetal 1 reacted with 2 to obtain multisubstituted pyridines 3 in the presence of zinc nitrate as the catalyst. The target compounds 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l were formed by the oxidation of 3, followed by the substitution with 3-(trifluoromethyl)phenol in the presence of potassium carbonate. Their structures were confirmed by IR, ~1H NMR, EI-MS, and elemental analyses. The preliminary bioassays indicated that some of them displayed moderate herbicidal activity against dicotyledonous weed Brassica campestris L at the concentration of 100 mg/L.

机译：为了找到新型的漂白除草剂先导化合物，制备了一系列新型的2-烷基（芳基）-4-氨基-3- [烷基（烷氧基）羰基] -5-氰基-6-[（3-三氟甲基）苯氧基]-吡啶。通过多步反应设计合成。在硝酸锌作为催化剂的存在下，N，S-乙缩醛1与2反应得到多取代的吡啶3。通过氧化3形成目标化合物5a，5b，5c，5d，5e，5f，5g，5h，5i，5j，5k，5l，然后在钾存在下用3-（三氟甲基）苯酚取代碳酸盐。通过IR，〜1H NMR，EI-MS和元素分析确认了它们的结构。初步的生物测定表明，其中一些对浓度为100 mg / L的双子叶杂草甘蓝型油菜具有中等的除草活性。

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《Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry》 |2013年第5期|共4页
作者
Zhai Y.-E.; Shi D.-Q.;
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正文语种 eng
中图分类 54.5;
关键词
herbicidal activity; multi-substituted pyridine; PDS inhibitor;

机译：除草活性;多取代吡啶;PDS抑制剂;

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1. Synthesis and herbicidal activity of 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy) carbonyl]-5-cyano-6-[(3-trifluoromethyl)phenoxy]-pyridines [J] . Zhai Y.-E., Shi D.-Q. Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2013,第5期

机译：2-烷基（芳基）-4-氨基-3- [烷基（烷氧基）羰基] -5-氰基-6-[（3-三氟甲基）苯氧基]-吡啶的合成及除草活性
2. Synthesis and Herbicidal Activity of 5-Alkyl(aryl)-3-[(3-trifluoromethyl) anilino]-4,5-dihydro-1H-pyrazolo[4,3-d]pyrimidin-4-imines [J] . Hai-Bo Li, De-Qing Shi Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2014,第3期

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3. Synthesis and Analgesic-Antiinflammatory Activities of Ethyl 2-[3-(1-phenoxy(methoxy)carbonyl-4-aryl-(alkyl)-1,4-dihydropyridyl)]acetates [J] . Sammy A. Agudoawu, Edward E. Knaus Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2000,第2期

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4. A Convenient Synthesis of 5-Alkyl Oxy- Carbonyl-6-Methyl-4-Aryl-3,4-Dihydro- Pyridone under Microwave Irradiation [C] . (missing) International symposium on green chemistry in China . 2002

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8. SYNTHESIS AND REACTIONS,OF CARBAMOYL AND ALKOXY-CARBONYL COMPLEXES OF MANGANESE AND RHENIUM [R] . R. W. Brink 1972

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Synthesis and herbicidal activity of 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy) carbonyl]-5-cyano-6-[(3-trifluoromethyl)phenoxy]-pyridines

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