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1. 发明申请

US20110218340A1 2-[1-Cyanopropyl)Carbamoyl]-5-Chloromethyl Nicotinic Acids and the Use Thereof in Manufacturing Herbicidal Imidazolinones 有权
标题翻译： 2- [1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸及其用途制造除草咪唑啉酮
公开(公告)号：US20110218340A1
公开(公告)日：2011-09-08
申请号：US13128782
申请日：2009-11-03
申请人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
发明人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
IPC分类号： C07D401/04 , C07D213/80
CPC分类号： C07D401/04 , C07D213/81
摘要： 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.
摘要翻译：其中Z是氢或卤素的式（I）的2- [（1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸; Z1是氢，卤素，氰基或硝基; R1是C1-C4烷基; R 2是C 1 -C 4烷基，C 3 -C 6环烷基或R 1和R 2，当与它们所连接的原子一起表示任选被甲基取代的C 3 -C 6环烷基时，R 3是氢或优选选自由碱金属，碱土金属，锰，铜，铁，锌，钴，铅，银，镍，铵和有机铵组成的组; 是合成除草咪唑啉酮的有用中间体。

2. 发明授权

US08629279B2 Process for manufacturing 5-formyl-pyridine-2,3-dicarboxylic acid esters 有权
标题翻译： 5-甲酰基 - 吡啶-2,3-二羧酸酯的制备方法
公开(公告)号：US08629279B2
公开(公告)日：2014-01-14
申请号：US13133013
申请日：2009-12-07
申请人： Michael Rack , Joachim Gebhardt , Frederik Menges , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
发明人： Michael Rack , Joachim Gebhardt , Frederik Menges , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
IPC分类号： C07D213/48 , C07D213/55
CPC分类号： C07D213/80
摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.
摘要翻译：制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式在碱金属或碱土金属醇盐或碳酸盐存在下，在极性非质子溶剂中，温度为-45〜40℃的亚硝化剂（Ⅲ）R3-ON = O（Ⅲ）其中R3为C1-C8-烷基 ℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在在0至100℃的温度范围内的路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

3. 发明授权

US08563734B2 2-[1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones 有权
标题翻译： 2- [1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸及其制备除草咪唑啉酮的用途
公开(公告)号：US08563734B2
公开(公告)日：2013-10-22
申请号：US13128782
申请日：2009-11-03
申请人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
发明人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
IPC分类号： C07D401/04 , C07D211/78
CPC分类号： C07D401/04 , C07D213/81
摘要： 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.
摘要翻译：其中Z是氢或卤素的式（I）的2- [（1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸; Z1是氢，卤素，氰基或硝基; R1是C1-C4烷基; R 2是C 1 -C 4烷基，C 3 -C 6环烷基或R 1和R 2，当与它们所连接的原子一起表示任选被甲基取代的C 3 -C 6环烷基时，R 3是氢或优选选自由碱金属，碱土金属，锰，铜，铁，锌，钴，铅，银，镍，铵和有机铵组成的组; 是合成除草咪唑啉酮的有用中间体。

4. 发明申请

US20110245505A1 Process for Manufacturing 5-Formyl-Pyridine-2,3-Dicarboxylic Acid Esters 有权
标题翻译： 5-甲酰基 - 吡啶-2,3-二羧酸酯的制备方法
公开(公告)号：US20110245505A1
公开(公告)日：2011-10-06
申请号：US13133013
申请日：2009-12-07
申请人： Michael Rack , Joachim Gebhardt , Frederik Menges , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
发明人： Michael Rack , Joachim Gebhardt , Frederik Menges , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schröder
IPC分类号： C07D491/048 , C07D213/803 , C07D213/80 , C07D401/04
CPC分类号： C07D213/80
摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.
摘要翻译：制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式在碱金属或碱土金属醇化物或碳酸盐存在下，在极性非质子溶剂中，温度为-45℃的亚硝化剂（III）R3-O-N = O（Ⅲ）其中R3为C1-C8-烷基至40℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在在0至100℃的温度范围内存在路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

5. 发明授权

US09096570B2 Process for manufacturing substituted 3-pyridylmethyl ammonium bromides 有权
标题翻译：制备取代的3-吡啶基甲基溴化铵的方法
公开(公告)号：US09096570B2
公开(公告)日：2015-08-04
申请号：US13128787
申请日：2009-11-13
申请人： Joachim Gebhardt , Frederik Menges , Michael Rack , Michael Keil , Jochen Schroeder , Stefan Orsten , Helmut Zech , David Cortes , Robert Leicht , Tony Yegerlehner , Rodney F. Klima
发明人： Joachim Gebhardt , Frederik Menges , Michael Rack , Michael Keil , Jochen Schroeder , Stefan Orsten , Helmut Zech , David Cortes , Robert Leicht , Tony Yegerlehner , Rodney F. Klima
IPC分类号： C07D401/06 , C07D403/06 , C07D413/06 , C07D417/06 , C07D213/80 , C07D401/04
CPC分类号： C07D401/04 , C07D213/80 , C07D401/06 , C07D403/06 , C07D413/06 , C07D417/06
摘要： A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; Y and Y1 are each independently OR1, NR1R2, or when taken together YY1 is —O—, —S— or NR3—; R1 and R2 are each independently hydrogen, C1-C4 alkyl optionally substituted with C1-C4 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is hydrogen or C1-C4 alkyl; comprises the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with bromine in the presence of a radical initiator in a solvent mixture comprising an aqueous phase and an organic phase, where the organic phase comprises a solvent selected from 1,2-dichloroethane, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene and tetrachloromethane, and where the pH-value of the aqueous phase is from 3 to
摘要翻译：制备5,6-二取代-3-吡啶基甲基溴化铵（I）的方法，其中Q是叔脂族或环状饱和的，部分不饱和的或芳族的胺; Z是氢或卤素; Z1是氢，卤素，氰基或硝基; Y和Y1各自独立地为OR 1，NR 1 R 2，或者当Y Y 1为-O - ， - S-或NR 3 - 时。 R 1和R 2各自独立地为氢，任选被C 1 -C 4烷氧基取代的C 1 -C 4烷基或任选被一至三个C 1 -C 4烷基，C 1 -C 4烷氧基或卤素原子取代的苯基，或任选被一至三个 C1-C4烷基，C1-C4烷氧基或卤原子; R3是氢或C1-C4烷基; 包括以下步骤：（i）在自由基引发剂存在下，将包含式（I）中给出的符号的式（II）化合物与溴在含水相和有机相的溶剂混合物中反应，其中有机相包含选自1,2-二氯乙烷，氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯和四氯甲烷的溶剂，其中水相的pH值来自 3至<8，得到3-溴甲基-5,6-二取代的吡啶化合物（III），其中Y，Y 1，Z和Z 1具有式（I）中给出的含义，和（ⅱ）使溴化合物式（III）与叔胺碱Q在溶剂中在约0℃至100℃的温度范围内

6. 发明授权

US08722893B2 Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides 有权
标题翻译：制备5-氯甲基-2,3-吡啶二羧酸酐的方法
公开(公告)号：US08722893B2
公开(公告)日：2014-05-13
申请号：US13128779
申请日：2009-11-03
申请人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schroeder
发明人： Frederik Menges , Joachim Gebhardt , Michael Rack , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schroeder
IPC分类号： C07D401/04 , C07D211/78
CPC分类号： C07D491/048 , C07D213/803 , C07D213/81 , C07D401/04 , C07D405/04
摘要： A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; comprising the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with a chlorinating agent, optionally in the presence of a radical initiator in a solvent selected from halogenated hydrocarbons, and (ii) crystallizing the compound (I) formed in step (i) from a solvent selected from chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, dichloroethane, trichloromethane, dichloromethane, toluene, xylenes, ethyl acetate, methyl tert.-butyl ether, and mixtures thereof. Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.
摘要翻译：制备其中Z为氢或卤素的5-氯甲基-2,3-吡啶二羧酸酐（I）的方法; Z1是氢，卤素，氰基或硝基; 包括以下步骤：（i）使式（II）化合物（其中符号具有式（I）中给出的含义）与氯化剂反应，任选在自由基引发剂存在下，在选自卤代烃，和（ii）从选自氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯，二氯乙烷，三氯甲烷，二氯甲烷，甲苯，二甲苯中的溶剂中使步骤（i）中形成的化合物（I），乙酸乙酯，甲基叔丁基醚及其混合物。化合物（I）是合成除草咪唑啉酮的有用中间体。

7. 发明申请

US20110224433A1 Process for Manufacturing Substituted 3-pyridylmethyl Ammonium Bromides 有权
标题翻译：制备取代的3-吡啶基甲基溴化铵的方法
公开(公告)号：US20110224433A1
公开(公告)日：2011-09-15
申请号：US13128787
申请日：2009-11-13
申请人： Joachim Gebhardt , Frederik Menges , Michael Rack , Michael Keil , Jochen Schroeder , Stefan Orsten , Helmut Zech , David Cortes , Robert Leicht , Tony Yegerlehner , Rodney F. Klima
发明人： Joachim Gebhardt , Frederik Menges , Michael Rack , Michael Keil , Jochen Schroeder , Stefan Orsten , Helmut Zech , David Cortes , Robert Leicht , Tony Yegerlehner , Rodney F. Klima
IPC分类号： C07D251/00 , C07D213/80 , C07D237/00 , C07D241/00 , C07D401/04
CPC分类号： C07D401/04 , C07D213/80 , C07D401/06 , C07D403/06 , C07D413/06 , C07D417/06
摘要： A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; Y and Y1 are each independently OR1, NR1R2, or when taken together YY1 is —O—, —S— or NR3—; R1 and R2 are each independently hydrogen, C1-C4 alkyl optionally substituted with C1-C4 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is hydrogen or C1-C4 alkyl; comprises the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with bromine in the presence of a radical initiator in a solvent mixture comprising an aqueous phase and an organic phase, where the organic phase comprises a solvent selected from 1,2-dichloroethane, chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene and tetrachloromethane, and where the pH-value of the aqueous phase is from 3 to
摘要翻译：制备5,6-二取代-3-吡啶基甲基溴化铵（I）的方法，其中Q是叔脂族或环状饱和的，部分不饱和的或芳族的胺; Z是氢或卤素; Z1是氢，卤素，氰基或硝基; Y和Y1各自独立地为OR 1，NR 1 R 2，或者当Y Y 1为-O - ， - S-或NR 3 - 时。 R 1和R 2各自独立地为氢，任选被C 1 -C 4烷氧基取代的C 1 -C 4烷基或任选被一至三个C 1 -C 4烷基，C 1 -C 4烷氧基或卤素原子取代的苯基，或任选被一至三个 C1-C4烷基，C1-C4烷氧基或卤原子; R3是氢或C1-C4烷基; 包括以下步骤：（i）在自由基引发剂存在下，将包含式（I）中给出的符号的式（II）化合物与溴在含水相和有机相的溶剂混合物中反应，其中有机相包含选自1,2-二氯乙烷，氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯和四氯甲烷的溶剂，其中水相的pH值来自 3至<8，得到3-溴甲基-5,6-二取代的吡啶化合物（III），其中Y，Y 1，Z和Z 1具有式（I）中给出的含义，和（ⅱ）使溴化合物式（III）与叔胺碱Q在溶剂中在约0℃至100℃的温度范围内

8. 发明申请

US20110224439A1 Process for Manufacturing 5-Chloromethyl-2,3-Pyridine Dicarboxylic Acid Anhydrides 有权
标题翻译：制备5-氯甲基-2,3-吡啶二羧酸酐的方法
公开(公告)号：US20110224439A1
公开(公告)日：2011-09-15
申请号：US13128779
申请日：2008-11-13
申请人： Frederik Menges , Joachim Gebhardt , Michael Rach , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schroeder
发明人： Frederik Menges , Joachim Gebhardt , Michael Rach , Michael Keil , Rodney F. Klima , David Cortes , Robert Leicht , Helmut Zech , Jochen Schroeder
IPC分类号： C07D471/04 , C07D401/04 , C07D213/80
CPC分类号： C07D491/048 , C07D213/803 , C07D213/81 , C07D401/04 , C07D405/04
摘要： A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; comprising the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with a chlorinating agent, optionally in the presence of a radical initiator in a solvent selected from halogenated hydrocarbons, and (ii) crystallizing the compound (I) formed in step (i) from a solvent selected from chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, dichloroethane, trichloromethane, dichloromethane, toluene, xylenes, ethyl acetate, methyl tert.-butyl ether, and mixtures thereof. Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.
摘要翻译：制备其中Z为氢或卤素的5-氯甲基-2,3-吡啶二羧酸酐（I）的方法; Z1是氢，卤素，氰基或硝基; 包括以下步骤：（i）使式（II）化合物（其中符号具有式（I）中给出的含义）与氯化剂反应，任选在自由基引发剂存在下，在选自卤代烃，和（ii）从选自氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯，二氯乙烷，三氯甲烷，二氯甲烷，甲苯，二甲苯中的溶剂中使步骤（i）中形成的化合物（I），乙酸乙酯，甲基叔丁基醚及其混合物。化合物（I）是合成除草咪唑啉酮的有用中间体。

9. 发明授权

US5935488A Deicing and anti-icing concentrated composition for aircraft 失效
标题翻译：除冰和防冰集中组合的飞机
公开(公告)号：US5935488A
公开(公告)日：1999-08-10
申请号：US133504
申请日：1998-08-12
申请人： Arnold Wiesenfeld , Alex Meyers , Robert Leicht
发明人： Arnold Wiesenfeld , Alex Meyers , Robert Leicht
IPC分类号： C09K3/18
CPC分类号： C09K3/185
摘要： A concentrated deicing and anti-icing composition which is diluted and is primarily used for aircraft surfaces being a mixture including a deicing and anti-icing base compound being propylene glycol and/or ethylene glycol in the overall range of 78.0% to 95.0% by weight of the deicing and anti-icing composition. A diluent is included in the form of water for use as a carrier fluid of the glycol in the overall range of 5.0% to 22.0% by weight of the deicing and anti-icing composition. A first nonionic surfactant agent is included having an HLB in the overall range of 4 to 17; and used in a weight proportion where the overall range is 1 ppm to 0.5% by weight of the deicing and anti-icing composition. A second nonionic surfactant agent is included having an HLB in the overall range of 5 to 18; and used in a weight proportion where the overall range is 1 ppm to 0.5% by weight of the deicing and anti-icing composition. The second nonionic surfactant agent has an HLB at least two (2) units higher than the first nonionic surfactant agent. An emulsifier is included in the form of a polycarboxylate compound being in the overall range of 1 ppm to 0.5% by weight of the deicing and anti-icing composition. A pH control agent maintains the pH of the deicing and anti-icing composition between a 6 and 10 value; and used in a weight proportion where the overall range is 1 ppm to 1.0% by weight of the deicing and anti-icing composition.
摘要翻译：被稀释并主要用于飞行器表面的集中除冰和防冰组合物是包含除冰和防冰基础化合物为丙烯二醇和/或乙二醇的混合物，其总重量范围为78.0％至95.0％的除冰和防冰组合物。在除冰和除冰组合物的5.0〜22.0重量％的范围内，以乙二醇的载体流体的形式含有稀释剂。包括HLB在4至17的总范围内的第一非离子表面活性剂; 并且以整体范围为除冰和除冰组合物的1〜0.5重量％的重量比例使用。包括HLB在5至18的总范围内的第二非离子表面活性剂; 并且以整体范围为除冰和除冰组合物的1〜0.5重量％的重量比例使用。第二非离子表面活性剂具有比第一非离子表面活性剂高至少两（2）单元的HLB。包含聚羧酸酯化合物形式的乳化剂在除冰和除冰组合物的1重量％至0.5重量％的范围内。 pH控制剂使除冰和防结冰组合物的pH维持在6至10之间; 并且以整体范围为除冰和除冰组合物的1〜1.0重量％的重量比例使用。

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