光气下游农药研究进展
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摘要
光气作为一种重要的精细化工中间体,广泛应用于合成农药、医药、材料等。综述了近年来光气下游农药研究进展。主要介绍了以光气作为原料在合成杀虫剂、杀菌剂、除草剂中的应用以及合成路线的优化。
Phosgene is a very important fine chemical intermediate, and widely used in the synthesis of agrochemical,medicine, material, etc. The article gives a review of the progress of research on the downstream agrochemicals of phosgene in recent years. This paper mainly introduces phosgene as raw material to synthesize insecticide, fungicide and herbicide, and the optimum process of preparing in agrochemicals.
Phosgene is a very important fine chemical intermediate, and widely used in the synthesis of agrochemical,medicine, material, etc. The article gives a review of the progress of research on the downstream agrochemicals of phosgene in recent years. This paper mainly introduces phosgene as raw material to synthesize insecticide, fungicide and herbicide, and the optimum process of preparing in agrochemicals.
引文
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[3]张建宇,雷粮林,汪影,等.光气生产技术及光气化产品开发进展[J].农药,2004,43(6):245-248.
[4]杨兴武.光气路线合成4-氯丁酰氯[J].精细化工中间体,2003,33(2):25-26.
[5]CLARK D A,FRAGA B G,ZHANG Wen-ming.Preparation of Heterocycle-substituted Bicyclic Azoles as Pesticides:WO,2016144351[P].2016-09-15.
[6]葛青,赵敏,郭飞,等.水合肼下游农药研究综述[J].农药,2009,48(3):157-162.
[7]王一军.500吨/年6-甲基-4-(3-吡啶亚甲基氨基)-1,2,4-三嗪酮工业化生产工艺总结[J].化工中间体,2012,4:1-8.
[8]赵东江,杨彬,王宇,等.吡蚜酮合成工艺改进研究[J].农药研究与应用,2011(2):12-14.
[9]KLAUS H M,KLAUS K,ODENTHAL P H.Preparation of4-Amino-1,2,4-triazol-5-ones:US,4952101[P].1990-08-28.
[10]徐庆丰,田超.高效杀虫剂吡蚜酮的合成[J].安徽农学通报,2013,19(4):76-77.
[11]CIPAC.Analysis of Technical and Formulated Pesticide[M].Handbook N,2009:73-82.
[12]FINNESSY J J,NAVARRO S X,SAMMONS R D,et al.Methods and Herbicidal Compositions that Modulate Expression of Plastid Protein Import System of Plants for Weed Control:US,0274712[P].2014-08-18.
[13]李翔,马海军,顾林玲,等.茚虫威合成路线研究与比较[J].现代农药,2009,8(5):23-16.
[14]杨丙连,孙克,张敏恒.茚虫威合成方法述评[J].农药,2012,51(10):774-777.
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[16]郑亚清,丁克鸿,冀超,等.硝基胍法制备吡虫啉工艺[J].农药,2014,53(1):17-20.
[17]METE A,MANKEE J B.Methylene-substituted Heterocyclic Compounds:EP,0652215[P].1995-05-10.
[18]程磊磊.杀虫剂吡虫啉的合成进展[J].安徽化工,2011,37(5):12-13.
[19]杨惠,张金桐.杀虫隆对末龄幼虫家蝇表皮成分及体内激素滴度的影响[J].寄生虫与医学昆虫学报,2004,11(3):174-178.
[20]仇是胜,李祥志,张世海,等.光气法合成杀虫隆[J].现代农药,2004,3(2):17-18.
[21]朱建荣,姜友法.三光气法合成恶虫酮的工艺[J].农药,2015,54(6):400-402.
[22]AGAR A D,SHINDE N A,BANDGAR B P.Microwaveassisted Synthesis of Triaryl Phosphatcs[J].Org Prep Proced,2000,32(3):26-27.
[23]陈霖,于海波,宋玉泉,等.恶虫酮的合成[C].中国化工学会农药专业委员会第十五届年会论文集,2012,233-236.
[24]胡笑形.重磅炸弹级农药的中间体市场与开发[J].精细化工中间体,2007,38(2):25-28.
[25]董捷,廖道华,楼江松,等.嘧菌酯的合成[J].精细化工中间体,2013,43(6):1-9.
[26]GILLIAN B,EWAN B C,VASS J H,et al.Preparation of Azoxystrobin:WO,2008043978[P].2008-04-17.
[27]彭志海.嘧菌酯关键中间体CMB的合成工艺研究及CMP的回收利用(硕士论文)[D].长沙:湘潭大学,2013.
[28]尹山红.一种邻羟基苯甲腈的制备方法:CN,104610095[P].2016-09-28.
[29]何伟明,郭嘉昒,周艳明.光气法合成邻羟基苯甲腈研究[J].上海化工,2012,37(6):10-13.
[30]周勇,黄炜,臧阳陵.邻羟基苯甲腈的合成方法及市场前景[J].精细化工中间体,2015,45(2):9-11,15.
[31]黄路,何海军,刘祈星.芳氧苯氧羧酸除草剂HNPC-A8169的创制研究[J].精细化工中间体,41(4):21-23.
[32]刘峰,慕卫,高杨杨,等.一种含啶菌恶唑和氟菌唑的杀菌组合物:CN,106035348[P].2016-06-28.
[33]KOZUE J,KAWAHARA A,TANIGAWA H,et al.Paste Formulations of Pesticides:JP,2007246496[P].2007-09-27.
[34]KOZUE J,KAWAHARA A,TANIGAWA H,et al.Method Using Agrochemicals for Controlling Plant Diseases and Pests:JP,2007246495[P].2007-09-27.
[35]谭成侠,徐瑶,曾仲武,等.杀菌剂氟菌唑的合成及表征[J].农药,2008,47(7):497-499.
[36]徐妍,马超,胡奕俊,等.咪鲜胺生产现状与市场分析[J].农药,2009,48(8):552-554.
[37]ANNA S,LUCIANA B,MIRELLA B,et al.Application of Liquid Chromatography with Electrospray Tandem Mass Spectrom Etrytothe Determination of a New Generation of Pesticides in Processed Fruits and Vegetables[J].J Chromatogr A,2004(1036):1612-1619.
[38]JOSE F,PILAR H,JOSEFA L,et al.Simplified Multiresidue Method for Determination of Pesticide Residues in Lettuce by Gas Chromatography with Nitrogen-phosphorus Detection[J].Anal Bioanal Chem,2007,389:643-651.
[39]张捷龙,张万昌,李纯聪,等.杀菌剂咪鲜胺的绿色合成[J].化学试剂,2010,32(9):856-858.
[40]翟慎吉,张薇,吴晓琳.一种含甲酰氨基嘧磺隆的除草组合物及其应用:CN,105994337[P].2016-10-12.
[41]DIEHR H J.Process for Preparing Substitute Oxadiazolones:US,5756752[P].1998-06-18.
[42]DIEHR H J.Prepara of Substituted Aminocarbonyltriazo-linones:EP,75704[P].1997-02-05.
[43]严传鸣,朱长武.胺唑草酮的除草特点和合成方法[J].现代农药,2006,5(2):11-13.
[44]陈明,聂萍,杨彬,等.2-溴-3-乙磺酰基吡啶的合成[J].农药,2010,49(5):326-328.
[45]童军,郑占英,严东文,等.玉喀磺隆新合成方法研究[J].化工中间体,2009(5):29-31.
[46]张大永,朱圣勇.玉嘧磺隆的合成[J].农药,2005,44(12):541-543.
[47]陈明,聂萍,杨彬.乙磺酰基乙腈的一种制备方法[J].精细化工中间体,2010,40(1):31-33.
[46]葛家成,陈鹏,司国栋.一种含有嘧啶肟草醚与丙苯磺隆的除草组合物:CN,104663698[P].2015-06-03.
[48]赵邦斌,姚日生,何普泉.三光气法合成磺酰脲类除草剂的研究[J].农药,2003,42(7):9-10.
[49]宋丽丽,耿丽文,杨丙连,等.丙苯磺隆合成方法概述[J].现代农药,2012,11(2):11-15.
[50]SUBLETT B J,MCCONNELL R L.Improved Process for Making Sulfonyl Isocyanates:WO,9606126[P].1996-07-03.
[51]静桂兰,张未星,钱柯伟.三光气合成恶草酮的研究[J].精细化工中间体,2008,38(3):18-20.
[52]何普泉,王兰兰.一种恶草酮的合成方法:CN,103641790[P].2015-09-30.
[53]潘忠稳.恶草酮的合成[J].安徽化工,2002(1):37-40.
[2]BABAD H,ZEILER A G.Chemistry of Phosgene[J].Chemical Reviews,2002,73(1):75-91.
[3]张建宇,雷粮林,汪影,等.光气生产技术及光气化产品开发进展[J].农药,2004,43(6):245-248.
[4]杨兴武.光气路线合成4-氯丁酰氯[J].精细化工中间体,2003,33(2):25-26.
[5]CLARK D A,FRAGA B G,ZHANG Wen-ming.Preparation of Heterocycle-substituted Bicyclic Azoles as Pesticides:WO,2016144351[P].2016-09-15.
[6]葛青,赵敏,郭飞,等.水合肼下游农药研究综述[J].农药,2009,48(3):157-162.
[7]王一军.500吨/年6-甲基-4-(3-吡啶亚甲基氨基)-1,2,4-三嗪酮工业化生产工艺总结[J].化工中间体,2012,4:1-8.
[8]赵东江,杨彬,王宇,等.吡蚜酮合成工艺改进研究[J].农药研究与应用,2011(2):12-14.
[9]KLAUS H M,KLAUS K,ODENTHAL P H.Preparation of4-Amino-1,2,4-triazol-5-ones:US,4952101[P].1990-08-28.
[10]徐庆丰,田超.高效杀虫剂吡蚜酮的合成[J].安徽农学通报,2013,19(4):76-77.
[11]CIPAC.Analysis of Technical and Formulated Pesticide[M].Handbook N,2009:73-82.
[12]FINNESSY J J,NAVARRO S X,SAMMONS R D,et al.Methods and Herbicidal Compositions that Modulate Expression of Plastid Protein Import System of Plants for Weed Control:US,0274712[P].2014-08-18.
[13]李翔,马海军,顾林玲,等.茚虫威合成路线研究与比较[J].现代农药,2009,8(5):23-16.
[14]杨丙连,孙克,张敏恒.茚虫威合成方法述评[J].农药,2012,51(10):774-777.
[15]许胜,张赟,金标.一种合成吡虫啉的方法:CN,105924428[P].2016-09-07.
[16]郑亚清,丁克鸿,冀超,等.硝基胍法制备吡虫啉工艺[J].农药,2014,53(1):17-20.
[17]METE A,MANKEE J B.Methylene-substituted Heterocyclic Compounds:EP,0652215[P].1995-05-10.
[18]程磊磊.杀虫剂吡虫啉的合成进展[J].安徽化工,2011,37(5):12-13.
[19]杨惠,张金桐.杀虫隆对末龄幼虫家蝇表皮成分及体内激素滴度的影响[J].寄生虫与医学昆虫学报,2004,11(3):174-178.
[20]仇是胜,李祥志,张世海,等.光气法合成杀虫隆[J].现代农药,2004,3(2):17-18.
[21]朱建荣,姜友法.三光气法合成恶虫酮的工艺[J].农药,2015,54(6):400-402.
[22]AGAR A D,SHINDE N A,BANDGAR B P.Microwaveassisted Synthesis of Triaryl Phosphatcs[J].Org Prep Proced,2000,32(3):26-27.
[23]陈霖,于海波,宋玉泉,等.恶虫酮的合成[C].中国化工学会农药专业委员会第十五届年会论文集,2012,233-236.
[24]胡笑形.重磅炸弹级农药的中间体市场与开发[J].精细化工中间体,2007,38(2):25-28.
[25]董捷,廖道华,楼江松,等.嘧菌酯的合成[J].精细化工中间体,2013,43(6):1-9.
[26]GILLIAN B,EWAN B C,VASS J H,et al.Preparation of Azoxystrobin:WO,2008043978[P].2008-04-17.
[27]彭志海.嘧菌酯关键中间体CMB的合成工艺研究及CMP的回收利用(硕士论文)[D].长沙:湘潭大学,2013.
[28]尹山红.一种邻羟基苯甲腈的制备方法:CN,104610095[P].2016-09-28.
[29]何伟明,郭嘉昒,周艳明.光气法合成邻羟基苯甲腈研究[J].上海化工,2012,37(6):10-13.
[30]周勇,黄炜,臧阳陵.邻羟基苯甲腈的合成方法及市场前景[J].精细化工中间体,2015,45(2):9-11,15.
[31]黄路,何海军,刘祈星.芳氧苯氧羧酸除草剂HNPC-A8169的创制研究[J].精细化工中间体,41(4):21-23.
[32]刘峰,慕卫,高杨杨,等.一种含啶菌恶唑和氟菌唑的杀菌组合物:CN,106035348[P].2016-06-28.
[33]KOZUE J,KAWAHARA A,TANIGAWA H,et al.Paste Formulations of Pesticides:JP,2007246496[P].2007-09-27.
[34]KOZUE J,KAWAHARA A,TANIGAWA H,et al.Method Using Agrochemicals for Controlling Plant Diseases and Pests:JP,2007246495[P].2007-09-27.
[35]谭成侠,徐瑶,曾仲武,等.杀菌剂氟菌唑的合成及表征[J].农药,2008,47(7):497-499.
[36]徐妍,马超,胡奕俊,等.咪鲜胺生产现状与市场分析[J].农药,2009,48(8):552-554.
[37]ANNA S,LUCIANA B,MIRELLA B,et al.Application of Liquid Chromatography with Electrospray Tandem Mass Spectrom Etrytothe Determination of a New Generation of Pesticides in Processed Fruits and Vegetables[J].J Chromatogr A,2004(1036):1612-1619.
[38]JOSE F,PILAR H,JOSEFA L,et al.Simplified Multiresidue Method for Determination of Pesticide Residues in Lettuce by Gas Chromatography with Nitrogen-phosphorus Detection[J].Anal Bioanal Chem,2007,389:643-651.
[39]张捷龙,张万昌,李纯聪,等.杀菌剂咪鲜胺的绿色合成[J].化学试剂,2010,32(9):856-858.
[40]翟慎吉,张薇,吴晓琳.一种含甲酰氨基嘧磺隆的除草组合物及其应用:CN,105994337[P].2016-10-12.
[41]DIEHR H J.Process for Preparing Substitute Oxadiazolones:US,5756752[P].1998-06-18.
[42]DIEHR H J.Prepara of Substituted Aminocarbonyltriazo-linones:EP,75704[P].1997-02-05.
[43]严传鸣,朱长武.胺唑草酮的除草特点和合成方法[J].现代农药,2006,5(2):11-13.
[44]陈明,聂萍,杨彬,等.2-溴-3-乙磺酰基吡啶的合成[J].农药,2010,49(5):326-328.
[45]童军,郑占英,严东文,等.玉喀磺隆新合成方法研究[J].化工中间体,2009(5):29-31.
[46]张大永,朱圣勇.玉嘧磺隆的合成[J].农药,2005,44(12):541-543.
[47]陈明,聂萍,杨彬.乙磺酰基乙腈的一种制备方法[J].精细化工中间体,2010,40(1):31-33.
[46]葛家成,陈鹏,司国栋.一种含有嘧啶肟草醚与丙苯磺隆的除草组合物:CN,104663698[P].2015-06-03.
[48]赵邦斌,姚日生,何普泉.三光气法合成磺酰脲类除草剂的研究[J].农药,2003,42(7):9-10.
[49]宋丽丽,耿丽文,杨丙连,等.丙苯磺隆合成方法概述[J].现代农药,2012,11(2):11-15.
[50]SUBLETT B J,MCCONNELL R L.Improved Process for Making Sulfonyl Isocyanates:WO,9606126[P].1996-07-03.
[51]静桂兰,张未星,钱柯伟.三光气合成恶草酮的研究[J].精细化工中间体,2008,38(3):18-20.
[52]何普泉,王兰兰.一种恶草酮的合成方法:CN,103641790[P].2015-09-30.
[53]潘忠稳.恶草酮的合成[J].安徽化工,2002(1):37-40.