N-杂环甲基2-(4-杂芳氧基苯氧基)丙酰胺的合成及除草活性  

Synthesis and Herbicidal Activity of N-Arylmethyl-2-( 4-arylxoyphenoxy) propionamide

作　　者：刘祈星[1,2] 胡艾希[1] 王晓光[2] 雷满香[2] 欧晓明[2] 任叶果[2] 黄路[2] 柳爱平[2] 

机构地区：[1]湖南大学化学化工学院,长沙410082 [2]湖南化工研究院国家农药创制工程技术研究中心,长沙410007

出　　处：《高等学校化学学报》2014年第2期262-270,共9页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:21272062);"十二五"国家科技支撑计划课题(批准号:2011BAE06B03)资助~~

摘　　要：以2-(4-羟基苯氧)丙酸为原料,设计合成了16个新的手性N-杂环甲基2-(4-杂芳氧基苯氧基)丙酰胺化合物,其化学结构经核磁共振、色谱-质谱、红外光谱及元素分析确证.初步生物活性测定结果表明,合成的化合物在2.25×103g/ha剂量时对单子叶杂草马唐(Digitaria sanguinalis)、稗草(Echinochloa crus-galli)及狗尾草(Setaria viridis)等均具有90%以上的活性;进一步活性及作物安全性测试表明,化合物(R)-(+)-N-[(6-氯吡啶-3-基)甲基]-2-[4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯氧基]丙酰胺(2b)的除草活性高于噁唑酰草胺,且对水稻茎叶处理安全,同时对水稻田主要杂草千金子的活性远高于氰氟草酯;化合物的除草活性与立体构型有关,R构型为活性构型.Aryloxyphenoxypropionic acid（ APP） herbicides inhibiting acetyl-CoA carboxylase（ ACCase） have been identified as one of the most important herbicides. As part of continuous efforts to search for new herbi-cides with high efficacy, broad-spectrum activity and safety to crops, the commercialized APP herbicide metamifop was used as lead compounds for further optimization. Sixteen new N-arylmethyl 2-（ 4-arylxoy-phenoxy） propionamide compounds were designed and prepared by multistep synthetic procedures starting from （ R ）-（＋） 2-（ 4-hydroxyphenoxy ） propanoic acid, and their structures were characterized by 1 H NMR, 13 C NMR, LC/MS, IR and elemental analysis. Steric configuration was confirmed by chiral column liquid chromatography. The bioassay results indicated that all compounds exhibited 〉90% activity against crabgrass （ Digitaria sanguinalis L. ） , barnyard grass（ Echinochloa crus-galliL. ） and green foxtail（ Setaria Viridis L. ） at 2250 g/ha. Further herbicidal activity and phytotoxicit to crops results indicated that（ R）-（＋）-N-[ （6-chloro-pyridin-3-yl） methyl]- 2-（4-{[3-chloro-5-（ trifluoromethyl） pyridin-2-yl] oxy}phenoxy）-propanamide （2b） was more effective against Digitaria sanguinalis （ IC50 =15.4 g/ha ） and Echinochloa crus-galli （ IC50 =22.8 g/ha） than metamifop（IC50=31.9 g/ha and 25.0 g/ha）. In particular, compound 2b was safe to rice （Xiang zao xian 24） and more effective against Leptochloa than commercial cyhalofop-butyl. The herbicidal activity is related to steric configuration that the compounds of R configuration have more effective activity.

关 键 词：N-杂环甲基2-(4-杂芳氧基苯氧基)丙酰胺 除草活性 作物安全性 

分 类 号：O626[理学—有机化学]