含芳氧乙酰基和间-三氟甲基苯基的双酰胺化合物的合成及其除草活性

doi:10.11944/j.issn.1000-0518.2016.06.150322

摘要/Abstract

摘要：

通过组合不同除草作用机制的活性基团,采用芳氧乙酸为酸组分的Ugi四组分反应合成了一系列芳氧乙酰基和间三氟甲基苯基片段的双酰胺化合物3a~3v,采用IR、¹H NMR、EI-MS和元素分析等技术手段对其结构进行了表征。温室盆栽测试结果表明,部分目标化合物对油菜、反枝苋、稗草和马唐表现出中等至良好的除草活性,如化合物3r在温室盆栽时,在1.5 kg/ha剂量下,在苗前处理时对反枝苋和马唐显示出100%的抑制活性;在苗后处理时对马唐显示出100%的抑制活性。初步探讨了目标化合物的构效关系。

关键词: 双酰胺, 取代苯氧乙酸, 八氢番茄红素脱氢酶抑制剂, Ugi反应, 除草活性

Abstract:

Based on the combination of different active groups with different herbicidal modes of action, a series of diamide compounds 3a~3v containing of 2-(aryloxy)acetyl and meta-trifluoromethylphenyl moieties were designed and synthesized via the four-component Ugi reaction. Their structures were characterized by IR, ¹H NMR, EI-MS, and elemental analyses. The glass house bioassay(in vivo) shows that some of compounds 3 exhibit moderate to good herbicidal activities against B.campestris, A.retroflexus, E.crusgalli, and D.sanguinalis at a dose of 1.5 kg/ha. For example, compound 3r displays 100% inhibition aganist both of A.retroflexus and D.sanguinalis in the pre-emergence treatment, it also exhibits 100% inhibition aganist D.sanguinalis in the post-emergence treatment. In addition, the preliminary structure-activity relationships are also discussed.

Key words: diamide, aryloxy acetic acid, phytoene desaturase inhibitor, Ugi reaction, herbicidal activity

张瀚匀, 刘曼赟, 严刚, 石德清. 含芳氧乙酰基和间-三氟甲基苯基的双酰胺化合物的合成及其除草活性[J]. 应用化学, 2016, 33(6): 668-676.

ZHANG Hanyun, LIU Manyun, YAN Gang, SHI Deqing. Synthesis of Diamides Containing of 2-Aryloxyacetyl and meta-Trifluoromethylphenyl Moieties and Their Herbicidal Activity[J]. Chinese Journal of Applied Chemistry, 2016, 33(6): 668-676.

参考文献

[1]	WANG Mingqi,YE Fei. Study and Application of Phenoxycarboxylic Acid Herbicides[J]. New Pestic,2005,39(1):20-22(in Chinese). 王铭琦,叶非. 苯氧羧酸类除草剂的研究与应用进展[J]. 新农药,2005,39(1):20-22.
[2]	ZHANG Yuju,LI Jide,ZHANG Desheng,et al.Diagnose of Phytotoxicity and Technology of Safe Application of Phenoxycarboxylic Acid and Benzoic Acid Herbicides[J]. J He'nan Agric Sci,2001,30(11):13-15(in Chinese). 张玉聚,李继德,张德胜,等. 苯氧羧酸类和苯甲酸类除草剂药害诊断与安全应用技术[J]. 河南农业科学,2001,30(11):13-15.
[3]	Sandmann G,Böger P. In Herbicide Activity:Toxicology, Biochemistry, and Molecular Biology[M]. Roe R M,Burton J D,Kuhr R J. Eds. Amsterdam: IOS Press,1997: 1-10.
[4]	Sandmann G. In Herbicidal Classes in Development:Mode of Action, Targets, Genetic Engineering, Chemistry[M]. Böger P,Wakabayashi K,Hirai K,Eds. Berlin:Springer,2002: 43-55.
[5]	Mitchell G. In Synthesis and Chemistry of Agrochemicals IV, ACS Symposium Series[M]. Baker D A,Fenyes J G,Moberg W K,et al. Ed. Washington DC:American Chemical Society,1995,584:161-170.
[6]	Sandmann G,Kowalczyk-Schroder S,Taylor H M. Quantitative Structure-Activity Relationship of Fluridone Derivatives with Phytoene Desaturase[J]. Pestic Biochem Physiol,1992,42(1):1-6.
[7]	Sandmann G,Bramley P M,Böger P. New Herbicidal Inhibitors of Carotene Biosynthesis[J]. Pestic Sci,1985,10(1):19-24.
[8]	Heap I. International survey of herbicide resistance weeds,http://weedscience.com.
[9]	Ohno R,Nagaoka M,Hirai K,et al.Synthesis and Insecticidal Activity of Novel 1-Alkyl-3-Sulfonyloxypyrazole-4-Carboxamide Derivatives[J]. J Pestic Sci,2010,35(1):15-22.
[10]	Omura S,Tanaka T. Pesticide Chemistry[M]. Ohkawa H,Miyagawa H,Lee P W. Ed. Weinheim:Wiley-VCH,1991,7:87.
[11]	Guan A,Liu C,Yang X,et al.Application of the Intermediate Derivatization Approach in Agrochemical Discovery[J]. Chem Rev,2014,114(14):7079-7107.
[12]	Dömling A,Wang W,Wang K. Chemistry and Biology of Multicomponent Reactions[J]. Chem Rev,2012,112(6):3083-3155.
[13]	Marcaccini S,Torroba T. The Use of the Ugi Four-component Condensation[J]. Nat Protoc,2007,2(3):632-639.
[14]	Ugi I,Werner B,Dömling A. The Chemistry of Isocyanides, Their MultiComponent Reactions and Their Libraries[J]. Molecules,2003,8(1):53-66.
[15]	Zuo X,Mi N,Fan Z,et al.Synthesis of 4-Methyl-1,2,3-thiadiazole Derivatives via Ugi Reaction and Their Biological Activities[J]. J Agric Food Chem,2010,58(5):2755-2762.
[16]	HU Hanning,LI Anling,ZHANG Hanyun,et al.Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl-]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their Herbicidal Activity Evaluation[J]. Chinese J Org Chem,2015,35:2162-2167(in Chinese). 胡汉宁,黎安玲,张瀚匀,等. 利用Ugi反应合成2-{N-(3-三氟甲基苯基)-[3-(三氟甲基)苯甲酰、2-(取代苯氧)丙酰、2-(4,6-二甲氧基-嘧啶-2-氧基)苯甲酰]-氨基}-取代苯乙酰环己胺及其除草活性评价[J]. 有机化学,2015,35:2162-2167.
[17]	HE Hongwu,WANG Jun,LIU Zhaojie,et al.Study on Biologically Active Organophosphorus Compounds V.Syntheses and Properties of α-(Sunstituted Phenoxy-acetoxy) Alkyl Phosphonates[J]. Chinese J Appl Chem,1994,11(4):21-26(in Chinese). 贺红武,汪军,刘钊杰,等. 具有生物活性的有机磷化合物的研究V. α-[( 取代) 芳氧基乙酰氧基]烷基膦酸酯的合成和性质[J]. 应用化学,1994,11(4):21-26.
[18]	Ugi I,Meyr R,Lipinski M,et al.Cyclohexyl Isocyanide[J]. Org Synth,1961,41:13.
[19]	Chen X B,Shi D Q,Zhu X F. Synthesis, Crystal Structure and Biological Activities of O,O-Dialkyl α-[1-(2-Chlorothiazol-5-ylmethyl)-5-methyl-1H-1,2,3-triazol-4-ylcarbonyloxy]alkylphosphonates[J]. Chinese J Chem,2007,25(12):1854-1858.
[20]	Liu Y X,Wei D G,Zhu Y R,et al.Synthesis, Herbicidal Activities, and 3D-QSAR of 2-Cyanoacrylates Containing Aromatic Methylamine Moieties[J]. J Agric Food Chem,2008,56(1):204-212.