α-(4-氯-1-萘氧基乙酰氧基)烃基膦酸酯的合成与植调活性  

Synthesis and Plant Growth Regulation Activity of α-(4-Chloro-1-naphthyloxy acetoxy)alkyl phosphonates

作　　者：刘绪峰[1] 王运[1] 程珍贤[1] 贺红武[1] 

机构地区：[1]湖北大学化学与材料科学学院,武汉430062

出　　处：《应用化学》2005年第1期40-44,共5页Chinese Journal of Applied Chemistry

基　　金：湖北大学青年基金资助项目(090209)

摘　　要：在25℃V(CF3COOH)∶V(CH3COOH)=1∶9的反应介质中1萘甲醚被Cl-氯化,O2及催化量的NO+BF-4为氧化剂,合成了8种标题化合物6a^6h,产率为432%~565%,采用元素分析、IR、1HNMR和MS测试技术确证了它们的结构。初步考察了目标化合物的植物生长调节活性,大多数化合物显示出较好的生长素类的激素作用,质量浓度为01g/L时,化合物6f对小麦牙鞘的抑制率为-203%,促进率为258%,而化合物6h则分别为-153%和204%。比较了目标化合物6a^6h与萘氧乙酸及相应的α羟基膦酸酯的植物调节活性,目标化合物6a^6h在质量浓度为01g/L时,对小麦牙鞘的抑制率较相应的α羟基膦酸酯高出23%~45%,促进率高出024%~058%。比较了氯原子引入萘环后目标化合物生物活性的变化,氯原高母体化合物的植物调节活性。Eight title compounds were synthesized in yields of 43 2%~56 5% by chlorination of 1 methoxynaphthalene in CF 3 COOH/CH 3 COOH mixtures(volume ratio,1∶9) at 25℃ with Cl - as chlorine source, O 2 and catalytic amount of NO + BF - 4 as the oxidant. Their structures were confirmed by virtue of elemental analysis , IR, 1 H NMR and MS. The plant growth regulating activities of the compounds were examined . Most of the compounds have a remarkable plant growth regulating activity, for compounds 6f and 6h the inhibiting activities are -20 3%(6f) and -15 3%(6h) respectively on wheat coleoptile at the concentration of 0 1 g/L , and promoting activities 2 58%(6f) and 2 04%(6h) at the concentration of 0 01 g/L. The inhibition rates of compounds 6a^6h on wheat coleoptile are increased compared with those of 1 hydroxyalkanephosphonic esters (5a^5h) by 2 3%~4 5%, and promotion rates are also increased by 0 24%~0 58%. Chlorine in naphthalene ring appears in favor of improving biological activity of these compounds.

关 键 词：膦酸酯 氯萘酚 植物生长调节活性 

分 类 号：O624.5[理学—有机化学]