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    • 21. 发明授权
      US06815563B2 Method for producing bicyclic 1,3-diketones 失效
    • Method for producing bicyclic 1,3-diketones
    • 双环1,3-二酮的制备方法
    • US06815563B2
    • 2004-11-09
    • US10332034
    • 2003-01-06
    • Klaus Langemann , Ulf Misslitz , Ernst Baumann , Wolfgang von Deyn , Steffen Kudis , Thorsten Volk , Guido Mayer
    • Klaus Langemann , Ulf Misslitz , Ernst Baumann , Wolfgang von Deyn , Steffen Kudis , Thorsten Volk , Guido Mayer
    • A01N4358
    • C07C255/47 , C07C17/00 , C07C45/27 , C07C45/29 , C07C45/298 , C07C45/673 , C07C49/433 , C07C2602/44 , C07C23/30 , C07C49/693
    • A process for preparing bicyclic 1,3-diketones of the formula I where R1, R2, R3 and R4 are hydrogen, C1-C4-alkyl, C1-C4-alkoxy-carbonyl, halogen, cyano, nitro, C1-C4-alkylthio, C1-C4-alkylsulfenyl or C1-C4-alkylsulfonyl and Z is C1-C4-alkylene, O, S, N—R5 where R5 is C1-C4-alkyl or C1-C4-alkylcarbonyl, which comprises a) reacting a bicyclic olefin of the formula II with haloform in the presence of a base to give the ring-expanded product of the formula III  where R1-R4 and Z are as defined above and X is halogen; b) hydrolyzing the allylic halogen of the compound of the formula III to the allyl alcohol of the formula IV c) oxidizing the allyl alcohol of the formula IV to the unsaturated ketone of the formula V d) reacting the ketone of the formula V with a nucleophilic ion Y− which stabilizes a negative charge to give the ketone of the formula VI e) hydrolyzing the ketone of the formula VI to the bicyclic 1,3-diketone of the formula I, novel intermediates and novel processes for preparing these intermediates are described.
    • 制备式I其中R 1，R 2，R 3和R 4的双环1,3-二酮的方法是氢，C 1 -C 4 - 烷基，C 1 -C 4 - 烷氧基 - 羰基，卤素 氰基，硝基，C 1 -C 4 - 烷硫基，C 1 -C 4烷基硫基或C 1 -C 4 - 烷基磺酰基，Z是C 1 -C 4 - 亚烷基，O，S，NR 5，其中R 5是C 1 -C 4烷基或C 1 -C4 - 烷基羰基，其包括a）在碱存在下使式II的双环烯烃与卤代甲基反应，得到式III的环扩展产物，其中R 1 -R 4和Z如上所定义，X和X 将式III的化合物的烯丙基卤水解成式IVc的烯丙醇，将式Ⅳ的烯丙醇氧化为式ⅤⅤ的不饱和酮）使式Ⅴ的酮与 使负电荷稳定以得到式VIe的酮）将式VI的酮水解成式I的双环1,3-二酮的新型中间体和新方法 描述这些中间体。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 29. 发明授权
      US06559100B1 2-benzoyl-cyclohexane-1,3-diones 失效
    • 2-benzoyl-cyclohexane-1,3-diones
    • US06559100B1
    • 2003-05-06
    • US09485223
    • 2000-02-07
    • Stefan Engel , Joachim Rheinheimer , Ernst Baumann , Wolfgang von Deyn , Regina Luise Hill , Guido Mayer , Ulf Misslitz , Oliver Wagner , Matthias Witschel , Martina Otten , Helmut Walter , Karl-Otto Westphalen
    • Stefan Engel , Joachim Rheinheimer , Ernst Baumann , Wolfgang von Deyn , Regina Luise Hill , Guido Mayer , Ulf Misslitz , Oliver Wagner , Matthias Witschel , Martina Otten , Helmut Walter , Karl-Otto Westphalen
    • C07D2604
    • C07D307/58 , A01N43/80 , C07D261/04
    • Substituted 2-benzoylcyclohexane-1,3-diones of the formula I where: R1 and R2 are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, —OR3, —OCOR3, —OSO2R3, —S(O)nR3, —SO2OR3, —SO2N(R3)2, —NR3SO2R3 or —NR3COR3; R3 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl or phenyl-C1-C6-alkyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R3, —OR3, —SR3, —N(R3)2, ═NOR3, —OCOR3, —SCOR3, —NR3COR3, —CO2R3, —COSR3, —CON(R3)2, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last mentioned radicals may in turn be substituted; n is 0, 1 or 2; Q is a cyclohexane-1,3-dione ring with or without substitution which is attached in position 2; X1 is a straight-chain or branched C1-C6-alkylene, a C2-C6-alkenylene or a C2-C6-alkynylene chain, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups: —OR4, —OCOR4, —OCONHR4 or —OSO2R4; except for those of the abovementioned alkenylene radicals where the double bond is &agr;,&bgr; to the phenyl ring and where Het is linked to the double bond via the &bgr; position; R4 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, phenyl-C1-C6-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals: hydroxyl, mercapto, amino, cyano, nitro, formyl, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy, C1-C4-haloalkoxy; Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the group consisting of: nitrogen, oxygen or sulfur, where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R5; R5 is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy, C1-C4-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals: cyano, formyl, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkoxy, C1-C4-haloalkoxy; and agriculturally useful salts thereof, processes and intermediates for preparing compounds of the formula I, compositions comprising them, and the use of the compounds of the formula I and compositions comprising them for controlling harmful plants are described.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 30. 发明授权
      US06500950B1 Benzylidenepyrazolones, their preparation and use 失效
    • Benzylidenepyrazolones, their preparation and use
    • 亚苄基吡唑啉酮，其制备和用途
    • US06500950B1
    • 2002-12-31
    • US09765626
    • 2001-01-22
    • Joachim Rheinheimer , Matthias Witschel , Stefan Engel , Ernst Baumann , Wolfgang von Deyn , Regina Luise Hill , Guido Mayer , Ulf Misslitz , Oliver Wagner , Martina Otten , Karl-Otto Westphalen , Helmut Walter
    • Joachim Rheinheimer , Matthias Witschel , Stefan Engel , Ernst Baumann , Wolfgang von Deyn , Regina Luise Hill , Guido Mayer , Ulf Misslitz , Oliver Wagner , Martina Otten , Karl-Otto Westphalen , Helmut Walter
    • C07D41310
    • C07D413/06 , A01N43/56 , A01N43/78 , A01N43/80 , C07D231/16 , C07D231/20
    • Benzylidenepyrazolones of the formula I, where the substituents and the index n have the following meanings: R1 is unsubstituted or substituted C1-C6-alkyl; R2 is unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C1-C6-alkoxy, halogen, nitro, cyano; R3 is hydrogen, halogen, nitro, cyano, a group NR5R6, OCOR5, NR5COR6, CO2R5, —COSR5, —CONR5R6, C1-C4-alkoxyiminoalkyl, C1-C6-alkylcarbonyl, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-alkylthio, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, an unsubstituted or substituted 5- or 6-membered saturated or unsaturated heterocycle which may contain up to 4 nitrogen atoms and/or up to 2 oxygen or sulfur atoms as ring members; R4 is C1-C6-alkyl, C1-C4-haloalkyl; R3 and R4 form an optionally substituted saturated or unsaturated 2- or 3-membered bridge which may contain a sulfur atom which may be oxidized to the sulfoxide or sulfone; R5 is hydrogen or unsubstituted or substituted C1-C6-alkyl; R6 is unsubstituted or substituted C1-C6-alkyl; R7 is hydrogen, C1-C6-alkyl or C1-C4-haloalkyl; n is 0,1 or 2, X is hydrogen, chlorine or bromine; where the compounds claimed may be present both in the trans and in the cis form or as a mixture of these isomers, are described.
    • 式I的亚苄基吡唑酮，其中取代基和指数n具有以下含义：R 1是未取代的或取代的C 1 -C 6 - 烷基; R 2是未取代的或取代的C 1 -C 6 - 烷基，未取代或取代的C 1 -C 6 - 烷氧基，卤素 硝基，氰基; R 3是氢，卤素，硝基，氰基，NR 5 R 6，OCOR 5，NR 5 COR 6，CO 2 R 5，-COSR 5，-CONR 5 R 6，C 1 -C 4烷氧基亚氨基烷基，C 1 -C 6烷基羰基，未取代或取代的C 1 -C 6 - 未取代或取代的C 1 -C 6 - 烷硫基，未取代或取代的C 2 -C 6 - 烯基，未取代或取代的C 2 -C 6 - 炔基，未取代或取代的苯基，未取代或取代的苯氧基，未取代的 或可以含有至多4个氮原子和/或至多2个氧或硫原子作为环成员的取代的5或6元饱和或不饱和杂环; R 4是C 1 -C 6烷基，C 1 -C 4卤代烷基; R 3和 R4形成任选取代的饱和或不饱和的2-或3-元 桥可以含有可被氧化成亚砜或砜的硫原子; R5是氢或未取代或取代的C1-C6-烷基; R6是未取代的或取代的C1-C6-烷基; R7是氢，C1-C6-烷基 或C 1 -C 4卤代烷基; n为0,1或2，X为氢，氯或溴;其中要求保护的化合物可以以反式和顺式形式存在，或以这些异构体的混合物存在。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
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