CN103270041A - 二噻英-四羧基-二酰亚胺的制备方法 - Google Patents
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Abstract
本发明涉及一种新的制备二噻英-四羧基-二酰亚胺的方法。
Description
本发明涉及一种新的制备二噻英-四羧基-二酰亚胺(dithiine-tetracarboxy-diimide)的方法。
二噻英-四羧基-二酰亚胺本身已经是已知的。还已知这些二噻英-四羧基-二酰亚胺可以用作驱虫剂抵抗动物体内寄生虫，特别是线虫，并且具有杀虫活性（参见US 3,364,229）。此外还已知某些二噻英-四羧基-二酰亚胺具有抗菌活性并且对人类真菌（human mycoces）具有一定的活性（参见Il Farmaco
60,944-947）。还已知二噻英-四羧基-二酰亚胺在作物保护中可以用作杀真菌剂抵抗植物病原真菌（参见WO 2010/043319）。此外已知二噻英-四羧基-二酰亚胺可以在光电照相感光器中用作颜料或在油漆和聚合物中用作染料（参见JP-A 10-251265、PL-B 143804）。
式（I）的二噻英-四甲酰亚胺可以以各种已知的方式制备
其中
R1和R2相同或不同，并且为氢、或为任选地被卤素、-OR3，和/或-COR4单取代或多取代的C1-C8-烷基、为任选地被卤素、C1-C4-烷基或C1-C4-卤代烷基单取代或多取代的C3-C7-环烷基、或为任选地被卤素、C1-C4-烷基、C1-C4-卤代烷基、-COR4或磺酰胺基单取代或多取代的芳基或芳基-(C1-C4-烷基)，
R3为氢、C1-C4-烷基或C1-C4-烷基羰基或为任选地被卤素、C1-C4-烷基或C1-C4-卤代烷基单取代或多取代的芳基，
R4为羟基、C1-C4-烷基或C1-C4-烷氧基。
例如，在一种已知的方法中（参见Synthetic Communications
，36，3591-3597），在第一步，琥珀酸酐任选地在一种稀释剂存在下与式（II）的胺反应。随后，生成的式（III）琥珀单酰胺与大大过量的亚硫酰氯在作为稀释剂的二氧杂环己烷存在下在室温下反应，最终在多个反应步骤之后得到式（I）二噻英-四羧基-二酰亚胺。二噻英-四羧基-二酰亚胺任选地从反应混合物直接分离或通过加入水后过滤分离。根据反应条件（稀释剂）和R基团的性质，在某些情况下可以在式（IV）二噻英-二异酰亚胺转化为式（I）二噻英-四羧基-二酰亚胺前将其分离：
此方法的不利之处在于长的反应时间以及产量，其中所获得的收率通常不超过理论值的约30-40%，或者所分离产品的纯度不足。在水后处理（aqueous work-up）反应混合物的情况下，另一个不利之处为其涉及破坏大量的亚硫酰氯，形成的气体（SO2和HCl）必须被处理。同样不利之处为，由经验得知，产品不能一次性获得。相反，通常情况是通过过滤首先分离产品后，延长停留时间（例如过夜）之后，另外的产品从滤液中沉淀出，并且必须通过过滤再次分离。有时这种操作必须再进行一次。该步骤非常费力并且耗费时间。
在另一个已知的方法中（参见US3,364,229；Chem.Ber.
100，1559-70），在第一步，式（V）二氯马来酸酐任选地在一种稀释剂存在下与一种式（II）的胺反应。随后，生成的式（VI）二氯马来酰亚胺与一种硫给体化合物（例如硫化氢、硫脲或硫代硫酸钠）反应：
该方法具有不利之处在于，例如，用高毒性气体硫化氢操作从技术角度讲非常困难、昂贵并且不方便。在US3,364,229中，当使用硫脲时，使用水和醇（例如甲醇、乙醇和异丙醇）的混合物。此外，推荐丙酮和水的混合物。根据所述方法（实施例7），在反应温度最高达60℃使用N-甲基二氯马来酰亚胺作为起始原料在均匀的混合物中仅能获得57%的产率。
因此仍然需要式（I）二噻英-四羧基-二酰亚胺的技术上简单和经济的制备方法。
现在发现了新的方法用于制备通式（I）二噻英-四羧基-二酰亚胺
其中R1和R2具有上面指出的定义，
其特征在于
式（VI）的二氯马来酰亚胺
其中R为R1或R2
任选地在一种相转移催化剂存在下与硫脲在水中反应。
当实施本发明方法时用作起始原料的二氯马来酰亚胺的一般定义由式（VI）提供。R代表R1或R2的定义。
R1和R2优选为相同或不同并且优选为氢，或为任选地被氟、氯、溴、-OR3和/或-COR4单取代或多取代的C1-C6-烷基，或为任选地被氯、甲基或三氟甲基单取代或多取代的C3-C7-环烷基，或为各自任选地被氟、氯、溴、甲基、三氟甲基、-COR4和/或磺酰胺基单取代或多取代的苯基或苯基-(C1-C4-烷基)。
R1和R2更优选为相同或不同并且更优选为氢，或为任选地被氟、氯、羟基、甲氧基、乙氧基、甲基羰氧基和/或羧基单取代或多取代的C1-C4-烷基，或为任选地被氯、甲基或三氟甲基单取代或多取代的C3-C7-环烷基，或为各自任选地被氟、氯、溴、甲基、三氟甲基、-COR4和/或磺酰胺基单取代至三取代的苯基、苯甲基、1-苯乙基、2-苯乙基或2-甲基-2-苯乙基。
R1和R2极优选为相同或不同并且极优选为氢、甲基、乙基、正丙基、异丙基、2,2-二氟乙基或2,2,2-三氟乙基，或为各自任选地被氯、甲基或三氟甲基取代的环丙基或环己基。
R1和R2更特别优选同时为甲基。
R3优选为氢、甲基、乙基、甲基羰基或乙基羰基或为任选地被氟、氯、甲基、乙基、正丙基、异丙基或三氟甲基单取代或多取代的苯基。
R3更优选为氢、甲基、甲基羰基或苯基。
R4优选为羟基、甲基、乙基、甲氧基或乙氧基。
R4更优选为羟基或甲氧基。
作为起始原料特别优选使用N-甲基二氯马来酰亚胺（VI-1），R=Me，得到终产物化合物（I-1）2,6-二甲基-1H,5H-[1,4]二噻英[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮。
如果二氯马来酰亚胺（VI-2），R=H用作起始原料，获得化合物(I-2)1H,5H-[1,4]二噻英[2,3-c:5,6-c’]联吡咯-1,3,5,7(2H,6H)四酮作为终产物。
本发明的方法不需要任何在反应终止时需处理或回收的有机溶剂，并且达到了相对高的产率。
硫脲用量为每摩尔式（VI）二氯马来酰亚胺0.8至2mol。优选的用量为每摩尔式（VI）的二氯马来酰亚胺0.9至1.7mol的硫脲，更优选为1.0至1.3mol的硫脲。
硫脲可以以固体形式或作为水中的溶液/悬浮液加入至反应混合物。优选首先加入水中的硫脲。
本发明方法的反应温度可以在宽的界限内变化，并且在40℃至150℃之间。为获得满意的时空产率，优选在50℃至120℃，更优选在60℃至100℃之间进行。
式（VI）二氯马来酰亚胺优选在60℃至90℃计量加入至水溶液。
在水中反应的情况下，可以任选地加入相转移催化剂（PTC）。作为相转移催化剂原则上可以使用具有已知作为PTC活性的所有化合物。该化合物可以为例如季铵盐或季鏻盐类的相转移催化剂。
该相转移催化剂优选具有通式（VII）
其中
A为N或P，
R5、R6、R7和R8为相同或不同并且独立地为支化或未支化的C1-C28-烷基、C6-C10-芳基或苯甲基，
X为卤素、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根或乙酸根。
X优选为溴、氯、氟、硫酸氢根、硫酸根、磷酸根和乙酸根。
式（VII）相转移催化剂可以给出的实例包括下述物质：苯甲基三丁基溴化铵、苯甲基三丁基氯化铵、苯甲基三乙基溴化铵、苯甲基三乙基氯化铵、苯甲基三甲基氯化铵、十六烷基三甲基溴化铵、二癸基二甲基氯化铵、二甲基双十八烷基硫酸氢铵、二甲基双十八烷基甲硫酸铵、十二烷基三甲基溴化铵、十二烷基三甲基氯化铵、甲基三丁基氯化铵、甲基三丁基硫酸氢铵、甲基三辛酰基氯化铵、甲基三辛基氯化铵、十四烷基三甲基溴化铵、苯基三甲基氯化铵、四丁基氯化铵、四丁基氟化铵、四丁基溴化铵、四丁基硫酸氢铵、四丁基氢氧化铵、四丁基碘化铵、四乙基溴化铵、四乙基氯化铵、四乙基氢氧化铵、四己基溴化铵、四己基碘化铵、四甲基溴化铵、四甲基氯化铵、四甲基氟化铵、四甲基氢氧化铵、四甲基碘化铵、四辛基溴化铵、四丙基溴化铵、四丙基氯化铵、四丙基氢氧化铵、三丁基甲基氯化铵、三乙基苯甲基氯化铵、四苯基溴化鏻、乙基三苯基溴化鏻、乙基三苯基碘化鏻和乙基三苯基乙酸鏻，以及这些物质的混合物。
此外，对于相转移催化剂还可以使用例如4-二烷基氨基-吡啶鎓盐或六烷基-胍盐。
相转移催化剂可以使用的范围为0.1至20mol%，基于式（VI）二氯马来酰亚胺计。
本发明方法中反应时间为15分钟至24小时。优选进行30分钟至12小时，更优选1至6小时。
产品后处理通过过滤进行。
本发明方法通过下面实施例阐明，但不限于此。
对比实施例1
对比实施例根据Chemische Berichte[Chemical Reports]1967，100，1559-1570（第1566页，Method B）进行。
加入9g（0.05mol）的N-甲基二氯马来酰亚胺在50 g水中的溶液，然后在60分钟的时间段内在40℃下逐滴加入10%硫脲水溶液。随后，将混合物在40℃下搅拌5小时。之后使反应混合物冷却至10℃，并且通过抽吸过滤分离固体，各用20ml水然后用20mlMeOH洗涤，并且干燥。这得到3.7g绿色固体，根据HPLC分析，其75.8面积%的量由化合物（I-1）组成，相应于收率为理论值的38.8%。
实施例1
将4.2g（0.055mol）硫脲加入至100g水中。随后加入1.6g四丁基溴化铵并且将混合物加热至80℃。随后加入9g（0.05mol）的N-甲基二氯马来酰亚胺。然后反应混合物在80℃下搅拌2小时。之后将其冷却至20℃，并且通过抽吸过滤分离固体，各用20 ml水然后用20 mlMeOH洗涤，并且干燥。这得到6.5g绿色固体，根据HPLC分析，其含有93%量（相对于标准品）的化合物（I-1），相应于收率为理论值的85.3%。
实施例2
将4.2g（0.055mol）硫脲加入至100 g水中并且将溶液加热至80℃。随后加入9g（0.05mol）N-甲基二氯马来酰亚胺。然后反应混合物在80℃下搅拌2小时。之后将其冷却至20℃，并且通过抽吸过滤分离固体，用20ml水然后用20ml MeOH洗，并且干燥。这得到6.02g绿色固体，根据HPLC分析，其含有94.3%量（相对于标准品）的化合物（I-1），相应于收率为理论值的80.6%。
实施例3
将4.2g（0.055mol）硫脲加入至100g水中。随后加入0.8g四丁基溴化铵并且混合物加热至80℃。随后加入9g（0.05mol）N-甲基二氯马来酰亚胺。然后反应混合物在80℃下搅拌2小时。之后将其冷却至20℃，并且通过抽吸过滤分离固体，用20ml水然后用20ml MeOH洗，并且干燥。这得到6.2g绿色固体，根据HPLC分析，其含有94.3%量（相对于标准品）的化合物（I-1），相应于收率为理论值的82.6%。
实施例4
将4.2g（0.055mol）硫脲加入至100g水中。随后加入0.15g四丁基溴化铵并且混合物加热至80℃。随后加入9g（0.05mol）N-甲基二氯马来酰亚胺。然后反应混合物在80℃下搅拌2小时。之后将其冷却至20℃，并且通过抽吸过滤分离固体，用20ml水然后用20ml MeOH洗，并且干燥。这得到5.94g绿色固体，根据HPLC分析，其含有91.4%量（相对于标准品）的化合物（I-1），相应于收率为理论值的81%。
实施例5
将4.2g（0.055mol）硫脲加入至100g水中。随后加入0.38g甲基三正辛基氯化铵并且混合物加热至80℃。随后加入9g（0.05mol）N-甲基二氯马来酰亚胺。然后反应混合物在80℃下搅拌2小时。之后将其冷却至20℃，并且通过抽吸过滤分离固体，用20ml水然后用20mlMeOH洗，并且干燥。这得到5.8g绿色固体，根据HPLC分析，其含有94.7面积%量的化合物（I-1），相应于收率为理论值的82.1%。
Claims (6)
1.制备通式（I）二噻英-四羧基-二酰亚胺的方法
其中
R1和R2为相同或不同并且为氢，或为任选地被卤素、-OR3，和/或-COR4单取代或多取代的C1-C8-烷基，为任选地被卤素、C1-C4-烷基或C1-C4-卤代烷基单取代或多取代的C3-C7-环烷基，或为各自任选地被卤素、C1-C4-烷基、C1-C4-卤代烷基、-COR4或磺酰胺基单取代或多取代的芳基或芳基-(C1-C4-烷基)，
R3为氢、C1-C4-烷基或C1-C4-烷基羰基或为任选地被卤素、C1-C4-烷基或C1-C4-卤代烷基单取代或多取代的芳基，
R4为羟基、C1-C4-烷基或C1-C4-烷氧基，
其特征在于
式（VI）二氯马来酰亚胺
其中R为R1或R2
任选地在相转移催化剂存在下，在不含有机溶剂的条件下与硫脲在水中反应。
2.权利要求1的方法，其特征在于使用式（VII）相转移催化剂
其中
A为N或P，
R5、R6、R7和R8为相同或不同并且独立地为支化或未支化的C1-C28-烷基、C6-C10-芳基或苯甲基，
X为卤素、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根或乙酸根。
3.权利要求1或2的方法，其特征在于对于每mol式（VI）的二氯马来酰亚胺使用0.8至2mol硫脲。
4.权利要求1或2的方法，其特征在于对于每mol式（VI）二氯马来酰亚胺使用0.9至1.7mol硫脲。
5.权利要求1或2的方法，其特征在于对于每mol式（VI）二氯马来酰亚胺使用1.0至1.3mol硫脲。
6.权利要求1、2、3、4或5的方法，其特征在于硫脲首先加入至水中。
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| US61/345,268 | 2010-05-17 | ||
| PCT/EP2011/056967 WO2011138281A2 (de) | 2010-05-06 | 2011-05-02 | Verfahren zur herstellung von dithiin-tetracarboxy-diimiden |
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| MX2013002395A (es) * | 2010-09-03 | 2013-04-03 | Bayer Ip Gmbh | Procedimiento de preparacion de ditiin-tetracarboximidas. |
| EP2641908A1 (de) * | 2012-03-23 | 2013-09-25 | Bayer CropScience AG | Verfahren zur Herstellung von Dithiin-tetracarboximiden |
| US20190345150A1 (en) | 2016-04-12 | 2019-11-14 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| BR112018074943B1 (pt) | 2016-06-03 | 2022-07-26 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos |
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| BR112019001229B1 (pt) | 2016-07-22 | 2022-11-16 | Syngenta Participations Ag | Composto derivado de oxadiazol, composição agroquímica compreendendo o mesmo, método para controlar ou impedir infestação de plantas úteis por microrganismos fitopatogênicos e uso do referido composto como fungicida |
| WO2018029242A1 (en) | 2016-08-11 | 2018-02-15 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
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| BR112019020739B1 (pt) | 2017-04-05 | 2023-12-19 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
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| BR112019020756B1 (pt) | 2017-04-05 | 2023-11-28 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbicidas, composição agroquímica compreendendo os mesmos, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso desses compostos |
| WO2018185211A1 (en) | 2017-04-06 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
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| WO2019012011A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
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| WO2019053024A1 (en) | 2017-09-13 | 2019-03-21 | Syngenta Participations Ag | MICROBIOCIDE DERIVATIVES OF QUINOLINE (THIO) CARBOXAMIDE |
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| US20230112306A1 (en) | 2020-03-13 | 2023-04-13 | Syngenta Crop Protection Ag | Methods of controlling or preventing infestation of soybean plants by the phytopathogenic microorganism corynespora cassiicola |
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| EP4117435A1 (en) | 2020-03-13 | 2023-01-18 | Syngenta Crop Protection AG | Methods of controlling or preventing infestation of plants by the phytopathogenic microorganism corynespora cassiicola |
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| WO2022049144A1 (en) | 2020-09-02 | 2022-03-10 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
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2011
- 2011-05-02 EP EP11716588A patent/EP2566871A2/de not_active Withdrawn
- 2011-05-02 WO PCT/EP2011/056967 patent/WO2011138281A2/de active Application Filing
- 2011-05-02 RU RU2012152237/04A patent/RU2012152237A/ru not_active Application Discontinuation
- 2011-05-02 KR KR1020127031586A patent/KR20130065663A/ko not_active Application Discontinuation
- 2011-05-02 BR BR112012028395A patent/BR112012028395A2/pt not_active Application Discontinuation
- 2011-05-02 CN CN201180033469XA patent/CN103270041A/zh active Pending
- 2011-05-02 JP JP2013508457A patent/JP2013534904A/ja active Pending
- 2011-05-02 MX MX2012012872A patent/MX2012012872A/es not_active Application Discontinuation
- 2011-05-05 US US13/101,739 patent/US8609868B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2012152237A (ru) | 2014-06-20 |
| WO2011138281A2 (de) | 2011-11-10 |
| MX2012012872A (es) | 2012-11-29 |
| JP2013534904A (ja) | 2013-09-09 |
| WO2011138281A3 (de) | 2015-09-03 |
| EP2566871A2 (de) | 2013-03-13 |
| US20110275831A1 (en) | 2011-11-10 |
| BR112012028395A2 (pt) | 2015-09-15 |
| KR20130065663A (ko) | 2013-06-19 |
| US8609868B2 (en) | 2013-12-17 |
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