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[1]郑怡倩,等.杀菌剂氟嘧菌酯的合成[J].武汉工程大学学报,2018,40(01):23-27.[doi:10. 3969/j. issn. 1674?2869. 2018. 01. 004]
 ZHENG Yiqian,DING Lili,WANG Luyan,et al.Synthesis of Fungicides Fluoxastrobin[J].Journal of Wuhan Institute of Technology,2018,40(01):23-27.[doi:10. 3969/j. issn. 1674?2869. 2018. 01. 004]
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杀菌剂氟嘧菌酯的合成(/HTML)
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《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
40
期数:
2018年01期
页码:
23-27
栏目:
化学与化学工程
出版日期:
2018-02-25

文章信息/Info

Title:
Synthesis of Fungicides Fluoxastrobin
文章编号:
20180104
作者:
郑怡倩1 2丁莉莉1 2汪鲁焱1 2余 玉1 2刘安昌*1 2
1.武汉工程大学化工与制药学院,湖北 武汉 430205; 2.绿色化工过程教育部重点实验室(武汉工程大学),湖北 武汉 430205
Author(s):
ZHENG Yiqian12 DING Lili12 WANG Luyan12 YU Yu 12 LIU Anchang*12
1. School of Chemical Engineering and Pharmacy,Wuhan Institute of Technology,Wuhan 430205,China;2. Key Laboratory of Green Chemical Process(Wuhan Institute of Technology),Ministry of Education,Wuhan 430205,China
关键词:
:氟嘧菌酯杀菌剂合成
Keywords:
fluoxazole fungicide synthesis
分类号:
TQ450
DOI:
10. 3969/j. issn. 1674?2869. 2018. 01. 004
文献标志码:
A
摘要:
:以丙二酸二乙酯作为起始原料,依次经过氯化、氟化、环合得到3, 5-二羟基-4-氟嘧啶,然后与三氯 氧磷在回流作用下经过氯化反应,再与邻氯苯酚经过醚化反应得到4-氯-6-(2-氯苯氧基) -5-氟嘧啶,最后与 E-(5.6-二氢-[1, 4, 2] -二噁嗪-3-基) (2-羟基苯基) -甲酮-O-甲基肟发生醚化反应得到氟嘧菌酯。该合成工 艺的总收率为33.2%。产品结构经1HNMR光谱鉴定。该工艺路线具有原料易得、易于控制、收率高等优 势,适宜于工业化生产
Abstract:
Using diethyl 2-chloro-malonate as starting material, the 3,5-dihydroxy-4-fluoropyrimidine was synthesized through chlorination, fluorination, and cyclization reaction, then the 4-Chloro-6- (2-chlorophenoxy)-5-fluoropyrimidine was generated by chlorinating the 3,5-dihydroxy-4-fluoropyrimidine in the presence of phosphine oxychloride under reflux, and etherifying with o-chlorophenol. The final product fluoxastrobinto was obtained through the reaction of 4-Chloro-6-(2-chlorophenoxy) -5-fluoropyrimidine with E-(5.6-Dihydro-[1,4,2]-dioxizin-3-yl) - (2-hydroxyphenyl) -methanone-O-methyloxime. The structure of the product was confirmed by nuclear magnetic spectroscopy. The total yield of this synthetic process was more than 33.2%. Due to the available raw materials, mild?reactiveconditions and highyields, the developed synthetic routes is suitable forthe large-scale production in industry.

参考文献/References:

[1] 殷锦捷, 马海云,关爱莹,等. 高效杀菌剂氟嘧菌酯[J]. 农药,2003,42(3):40-42. [2] 武恩明, 孙克, 张敏恒. 氟嘧菌酯合成方法述评[J]. 农药, 2014, 53(7): 537-541. [3] 刘长令,李正名. Strobin类杀菌剂的创制经纬[J]. 农药,2003,42(3):43-46. [4] RAVI BABU G, RAJESH T, NAJARJUNA R, et al . An efficient and practical synthesis of dimethyl 2-chloromalonate[J]. Der Pharma Chemica, 2011, 3 (6):437-442 . [5] 娄万乔,张大永. 杀菌剂氟嘧菌酯的合成[J]. 现代农药,2017, 16(3):14-16,20. [6] 丁成荣,张长勇,张国富. 苯并呋喃-2,3-二酮(O-甲基肟)-2-肟的合成工艺[J]. 精细化工,2014,31(3):394-408.[7] BRAUN M, BROSCH C. Production of fluorine compounds: WO, 2002060838[P]. 2002-08-08. [8] CHEN W, COSSROW J, FRANKLIN L, et al. Pyrimidine-4-carboxamide compounds useful as Raf kinase inhibitors and their preparation and use in the treatment of Raf-mediated diseases:WO,2009006389[P]. 2009-01-08. [9] KOLN A P,LEVERKUSEN A M. Process for preparing ring-fluorinated aromatics :US,20060009643[P]. 2005-07-06. [10] RAO K, SUNDARAMU RTHYV. Reactivity of 2-Hydroxy--nitroacetophenones :syn-thesis of 2-Oximinocoumaranones[J]. Proceeding Indian Academic Science Section A,1976,83:238-242. [11] Pleschke A, Marhold A. Process for preparing ring-fluorinated aromatics: US, 2008182986 [P]. 2008-07-31. [12] VIC P, RAMA M H, AVINASH S M, et al. Process for preparing fluoxastrobin: US, 2015011753 [P]. 2016-11-14. [13] JONES R M , LEHMANN J, CHEN W , et al. Preparation of oxadiazolyl containing compounds as modulators of the GPR119 receptor for use in therapy:WO,2012040279[P]. 2012-05-29. [14] PRASAD V , GIBB C , LARSON C L . Process for preparing (E)(5,6-dihydro-1,42-dioxazine-3-yl) (2-hydroxyphenyl) methanone O-methyl oxime:WO,2016193822[P]. 2016-12-08.[15] HINDUPUR R M,MANE A S, BALAKRISHNAN S,et al. A process for the preparation of fluoxastrobin:US, 20150011753[P]. ?2015-01-08.

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备注/Memo

备注/Memo:
作者简介:郑怡倩,硕士研究生。 E-mail: lanchang163@163.com*通讯作者:刘安昌,博士,教授。E-mail:lanchang163@163.com引文格式:郑怡倩,丁莉莉,汪鲁焱,等. 杀菌剂氟嘧菌酯的合成[J]. 武汉工程大学学报,2017,40(1):23-27.
更新日期/Last Update: 2018-02-01