含取代吡啶基的不对称硫代磷(膦)酸酯的合成及杀菌活性研究  

Studies on Synthesis and Fungicidal Activities of Asymmetric Phosphoro(-no)thioates Containing Substituted Pyridine

作　　者：李小梅[1] 蔡觉晓[1] 刘建兵[1] 刘天麟[1] 唐除痴[1] 

机构地区：[1]南开大学元素有机化学重点实验室元素有机化学研究所,天津300071

出　　处：《农药学学报》2001年第4期22-30,共9页Chinese Journal of Pesticide Science

摘　　要：从二硫代磷酸二乙酯钠盐或 O,O-二乙基硫代磷酰氯出发 ,经酯化、去烷基化反应得到相应的硫代或二硫代铵盐 ,分别与 2 -氯 - 5 -氯甲基吡啶反应得产物 2 a～ 2 c。从 O-乙基硫代磷酰二氯或苯基硫代膦酰二氯出发 ,先与取代苯酚或甲胺反应 ,然后与 2 -氯 - 5 -羟甲基吡啶反应得到产物 2 d～ 2 k和 2 m～ 2 u。O-乙基 - S-丙基二硫代磷酰氯、O-乙基硫代磷酰二氯和苯基硫代膦酰二氯与 2 -氯 - 5 -羟甲基吡啶反应分别得产物 2 l、2 v和 2 w。所合成的 2 3个新化合物对9种植物病菌的离体及活体杀菌活性测试表明 ,其中一些化合物对水稻稻瘟病和水稻纹枯病有一定活性 ,个别化合物活性很好 。As starting materials, Na salt of O,O diethyldithiophosphoric acid and O,O diethyl thiophosphorochloridate via esterification and dealkylation give O ethyl ammoniumdithio or thiophosphates, which are treated with 2 chloro 5 chloromethylpyridine to give 2a^2c . O ethylthiophosphorodichloridate and phenylthiophosphorodichloride react with a substituted phenol or methylamine and then with 2 chloro 5 hydroxymethylpyridine forming 2d^2k and 2m^2u . O ethyl S propyldithiophosphorochloridate, O ethylthiophosphorodichloridate and phenylthiophosphonodichloride react with 2 chloro 5 hydroxymethylpyri dine to afford 2l, 2v and 2w, respectively. In this way, twenty three new title compounds 2 were prepared. The bioassay results showed that some of the title compounds possess a satisfactory or excellent fungicidal activity towards the R. solani(Palo) and P. oryzae fungus at mass fraction 5.0×10 -5 ( in vitro ) or 5.0×10 -4 ( in vivo ), but they have non or only lower fungicidal activity towards other seven plant fungi.

关 键 词：取代吡啶 硫(酮)代磷(膦)酸酯 二硫(醇)代磷酸酯 杀菌活性 有机磷杀菌剂 

分 类 号：TQ455.43[化学工程—农药化工]