含6-烷(芳)氧基多取代吡啶衍生物的合成与除草活性

Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives

采用6-烷硫基吡啶化合物为原料，用N，N-二甲基甲酰胺（DMF）为溶剂，双氧水为氧化剂，水合钨酸钠为催化剂，经过一步氧化变成6-烷砜基多取代吡啶化合物，再在醇钠或碳酸钾的催化作用下与醇或酚反应生成含烷（芳）氧基的多取代吡啶衍生物.通过^1H NMR，EI-MS，IR，元素分析等方法对所合成的化合物进行了结构表征.代表化合物2-甲基-4-氨基-5-氰基-6-（3-硝基苯氧基）烟酸甲酯经单晶X衍射确证了结构.对合成的含6-烷（芳）氧基多取代吡啶衍生物作了初步的除草活性测试，测试结果表明：含6-烷（芳）氧基多取代吡啶衍生物对油菜和稗草具有一定的除草活性，且化合物对油菜和稗草根的抑制优于对茎的作用，表现出明显的选择性.

Alkyl multisubstituted pyridine-2-yl sulfones have been designed and synthesized from 6-alkylthiopyridine using H2O2 and NaWO3·2H2O as catalysts in N,N-dimethylformamide （DMF）. A series of new 6-alkoxy（aryloxy） multisubstituted pyridine derivatives have been synthesized from alkyl multisubstituted pyridine-2-yl sulfone and alcohol or phenol using K2CO3 （NaOC2H5 or NaOCH3） as catalyst in CH3CN. The structures of target compounds have been confirmed by ^1H NMR, ^13C NMR, EI-MS, IR spectroscopy and elemental analysis. The structure of 4-amino-5-cyano-2-methyl-6-（3-nitryl phenoxy） nicotinic acid methyl ester has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess moderate herbicidal activities against the rape and barnyard grass and show obvious selectivity.