苯嗪草酮的合成工艺研究进展
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摘要
苯嗪草酮是一种低毒、高效、低残留的优良除草剂,主要用于甜菜田防除禾本科杂草和阔叶杂草,具有良好的市场前景。主要总结了近年来苯嗪草酮的合成工艺研究进展,对以苯甲酰甲酸酯为原料通过与乙酰肼反应缩合、肼解、脱水环合的3步法制备苯嗪草酮进行详细分析,对合成路线的原料、中间体及目标产物的合成进行分析对比,探讨每步的最优合成工艺,指出苯嗪草酮生产的关键问题及工业化生产的方向。
Metamitron is a kind of excellent herbicide with low toxicity, high efficiency and low residue. It is mainly used in beet field to control grass weeds and broadleaf weeds with good market prospect. The recent progress of the synthesis of metamitron was summarized. For the preparation of acethydrazide with benzoylformate as the raw material by three-step reaction of acetohydrazide condensation, hydrazinolysis, dehydration and cyclization, the synthesis of raw materials, intermediates and the synthesis of the target product were analyzed and compared to explore the optimal synthesis of each step process, the key issues in production of metamitron and the direction of industrial production were pointed out.
Metamitron is a kind of excellent herbicide with low toxicity, high efficiency and low residue. It is mainly used in beet field to control grass weeds and broadleaf weeds with good market prospect. The recent progress of the synthesis of metamitron was summarized. For the preparation of acethydrazide with benzoylformate as the raw material by three-step reaction of acetohydrazide condensation, hydrazinolysis, dehydration and cyclization, the synthesis of raw materials, intermediates and the synthesis of the target product were analyzed and compared to explore the optimal synthesis of each step process, the key issues in production of metamitron and the direction of industrial production were pointed out.
引文
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[17]蒋晓帆,赵昊昱.苯嗪草酮的合成[J].化学世界,2015,56(10):626-629.
[18]潘忠稳,杲海霞.苯嗪草酮的合成[J].农药,2007,46(3):166-167.
[19]陆阳,陶京朝,周志莲.苯嗪草酮的合成新工艺[J].化工中间体,2010(6):50-55.
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[22]鲍菊篱,鲍明路.苯嗪草酮的生产方法:CN,106187929[P].2015-05-05.
[2]CERARD A L,LISOWSKI V,RAULT S.Direct Synthesis of New Arylanthranilic Acids via a Suzuki cross Coupling Reaction from Iodoisatins[J].Tetrahedron,2005,61:6082-6087.
[3]APER J,MECHANT E,RUBIN B,et al.Absorption,Translocation and Metabolism of Metamitron in Chenopodium Album[J].Pest Management Science,2012,68(2):209-216.
[4]BETTINI P,MCNALLY S,SEVIGNAC M,et al.Atrazine Resistance in Chenopodium Album:Low and High Levels of Resistance to the Herbicide are Related to the Same Chloroplast PSBA Gene Mutation[J].Plant Physiol,1987,84(4):1442-1446.
[5]陆石松,施娟娟,倪珏萍.甜菜田除草剂应用研发进展[J].杂草科学,2012,30(2):6-10.
[6]顾林玲.三嗪酮类除草剂——苯嗪草酮[J].现代农药,2016,15(6):51-54.
[7]MANANDHAR J B.Effect of Light Temperature and Water Potential on Growth and Sporulation of Microdochiumoryzae[J].Mycologia,1998,90(6):995-1000.
[8]WINFRIED L,ANDREAS W.Process for the Preparation of Phenyiglyoxylic Acid Esters:US,4596885[P].1986-06-24.
[9]ROBERT H S,BARRY L S.Process for Making Nicotinic Acid Hydrazides:US,3951996[P].1976-04-20.
[10]ROBERT J S.Process for the Reductive Methylation of an Acid Hydrazide:US,4127611[P].1978-11-28.
[11]朱领地,赵继全,殷学智.乙酰肼合成新工艺研究[J].河北工业大学学报,1997,26(1):65-68.
[12]张翼.苯嗪草酮的合成研究(硕士论文)[D].杭州:浙江工业大学,2010.
[13]陈娟.苯嗪草酮的合成工艺研究(硕士论文)[D].上海:华东师范大学,2013.
[14]张晓玲.一种乙酰肼的合成方法:CN,106977420[P].2017-04-25.
[15]SHALIL S S.A Process for the Production of 4-Amino-3-methyl-6-phenyl-1,2,4-triazin[P].Indian:2003Mu00850,2005-06-10.
[16]丁成荣,张翼,谢思泽,等.2-乙酰肼基苯甲酰甲酸乙酯的合成[J].农药,2009,48(7):479-480.
[17]蒋晓帆,赵昊昱.苯嗪草酮的合成[J].化学世界,2015,56(10):626-629.
[18]潘忠稳,杲海霞.苯嗪草酮的合成[J].农药,2007,46(3):166-167.
[19]陆阳,陶京朝,周志莲.苯嗪草酮的合成新工艺[J].化工中间体,2010(6):50-55.
[20]HELMUT T,WILFRIED D.4-Amino-1,2,4-triazon-5-ones:US,4057546[P].1977-11-08.
[21]孔永辉,孔繁蕾,张元元,等.苯嗪草酮的制备方法:CN,102952089[P].2012-10-19.
[22]鲍菊篱,鲍明路.苯嗪草酮的生产方法:CN,106187929[P].2015-05-05.