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    N-Substituted .alpha.-ketocarboxylic acid amides
    1.
    发明授权
    N-Substituted .alpha.-ketocarboxylic acid amides 失效
    N-取代的α-酮羧酸酰胺

    公开(公告)号：US4228082A

    公开(公告)日：1980-10-14

    申请号：US56084

    申请日：1979-07-09

    申请人： Axel Kleemann ,  Herbert Klenk ,  Heribert Offermanns ,  Paul Scherberich ,  Werner Schwarze

    发明人： Axel Kleemann ,  Herbert Klenk ,  Heribert Offermanns ,  Paul Scherberich ,  Werner Schwarze

    IPC分类号： A01N25/00 ,  A01P3/00 ,  A01P13/00 ,  C07C67/00 ,  C07C231/00 ,  C07C231/06 ,  C07C231/08 ,  C07C235/72 ,  C07D307/54 ,  C07C103/737 ,  C07C103/76

    CPC分类号： C07D307/54

    摘要： Compounds are prepared of the formula ##STR1## where R' is a t-alkyl group having 4 to 18 carbon atoms, preferably t-butyl, t-amyl or t-octyl and R is a straight or branched chain alkyl group with 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms or an alkyl group substituted with one or more phenyl group or a halogen atom, particularly a chlorine atom, or a cycloalkyl group with 3 to 8 carbon atoms, particularly cyclopropyl, which can be substituted by one or more 1 to 3 carbon atom alkyl groups or one or more halogen atoms, preferably chlorine, or phenyl or naphthyl or a five membered heterocyclic group or such phenyl, naphthyl or heterocyclic group substituted by halogen atoms, nitro groups, alkyl or alkoxy with 1 to 5 carbon atoms by condensing in acid medium an acyl cyanide of the formulaR--CO--CN (II)where R is as defined above with either(a) a tertiary alcohol of the formulaHO--R' (III) in which R' is as defined above, or preferably(b) an alkene of the formula ##STR2## where R.sub.1 and R.sub.2 are the same or different and are hydrogen or an alkyl group and wherein R.sub.3 and R.sub.4 are the same or different and wherein the alkyl groups in each case can be 1 to 15 carbon atoms. Some of the compounds are new. They are useful as intermediates for synthesizing herbicides and can be used directly as fungicides.

    摘要翻译： 化合物由式（I）制备，其中R'是具有4至18个碳原子的叔烷基，优选叔丁基，叔戊基或叔辛基，R是直链或支链烷基 具有1至18个碳原子，优选1至10个碳原子的烷基或被一个或多个苯基或卤素原子，特别是氯原子或具有3至8个碳原子的环烷基特别是环丙基取代的烷基，其可以 被一个或多个1至3个碳原子的烷基或一个或多个卤素原子，优选氯，或苯基或萘基或五元杂环基或被卤素原子取代的苯基，萘基或杂环基，硝基，烷基 或具有1至5个碳原子的烷氧基，通过在酸性介质中缩合式R-CO-CN（II）的酰基氰，其中R如上定义，与（a）式HO-R'（III ），其中R'如上所定义，或优选（b）下式的烯烃（I） V）其中R 1和R 2相同或不同并且是氢或烷基，并且其中R 3和R 4相同或不同，并且其中每种情况下的烷基可以是1至15个碳原子。 一些化合物是新的。 它们可用作合成除草剂的中间体，可直接用作杀真菌剂。

    Process for the production of N-substituted .alpha.-ketocarboxylic acid amides
    2.
    发明授权
    Process for the production of N-substituted .alpha.-ketocarboxylic acid amides 失效
    制备N-取代的α-酮羧酸酰胺的方法

    公开(公告)号：US4224226A

    公开(公告)日：1980-09-23

    申请号：US926322

    申请日：1978-07-20

    申请人： Axel Kleemann ,  Herbert Klenk ,  Heribert Offermanns ,  Paul Scherberich ,  Werner Schwarze

    发明人： Axel Kleemann ,  Herbert Klenk ,  Heribert Offermanns ,  Paul Scherberich ,  Werner Schwarze

    IPC分类号： A01N25/00 ,  A01P3/00 ,  A01P13/00 ,  C07C67/00 ,  C07C231/00 ,  C07C231/06 ,  C07C231/08 ,  C07C235/72 ,  C07D307/54 ,  C07C102/08

    CPC分类号： C07D307/54

    摘要： Compounds are prepared of the formula ##STR1## where R' is a t-alkyl group having 4 to 18 carbon atoms, preferably t-butyl, t-amyl or t-octyl and R is a straight or branched chain alkyl group with 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms or an alkyl group substituted with one or more phenyl groups or a halogen atom, particularly a chlorine atom, or a cycloalkyl group with 3 to 8 carbon atoms, particularly cyclopropyl, which can be substituted by one or more 1 to 3 carbon atom alkyl groups or one or more halogen atoms, preferably chlorine, or phenyl or naphthyl or a five membered heterocyclic group or such phenyl, naphthyl or heterocyclic group substituted by halogen atoms, nitro groups, alkyl or alkoxy with 1 to 5 carbon atoms by condensing in acid medium an acyl cyanide of the formulaR--CO--CN (II)where R is as defined above with either(a) a tertiary alcohol of the formulaHO--R' (III) in which R' is as defined above, or preferably(b) an alkene of the formula ##STR2## where R.sub.1 and R.sub.2 are the same or different and are hydrogen or an alkyl group and wherein R.sub.3 and R.sub.4 are the same or different and wherein the alkyl groups in each case can be 1 to 15 carbon atoms. Some of the compounds are new. They are useful as intermediates for synthesizing herbicides and can be used directly as fungicides.

    摘要翻译： 化合物由式（I）制备，其中R'是具有4至18个碳原子的叔烷基，优选叔丁基，叔戊基或叔辛基，R是直链或支链烷基 具有1至18个碳原子，优选1至10个碳原子的烷基或被一个或多个苯基或卤素原子，特别是氯原子或具有3至8个碳原子的环烷基，特别是环丙基取代的烷基，其可以 被一个或多个1至3个碳原子的烷基或一个或多个卤素原子，优选氯，或苯基或萘基或五元杂环基或被卤素原子取代的苯基，萘基或杂环基，硝基，烷基 或具有1至5个碳原子的烷氧基，通过在酸性介质中缩合式R-CO-CN（II）的酰基氰，其中R如上定义，与（a）式HO-R'（III ），其中R'如上所定义，或优选（b）式“IMAGE”（ IV）其中R 1和R 2相同或不同并且是氢或烷基，并且其中R 3和R 4相同或不同，并且其中每种情况下的烷基可以是1至15个碳原子。 一些化合物是新的。 它们可用作合成除草剂的中间体，可直接用作杀真菌剂。

    Process for the production of acyl cyanides (B)
    3.
    发明授权
    Process for the production of acyl cyanides (B) 失效
    酰基氰生产工艺（二）

    公开(公告)号：US4108875A

    公开(公告)日：1978-08-22

    申请号：US802942

    申请日：1977-06-02

    申请人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    发明人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    IPC分类号： C07C253/14 ,  B01J23/00 ,  B01J27/00 ,  C07B61/00 ,  C07C67/00 ,  C07C253/00 ,  C07C255/17 ,  C07C255/18 ,  C07C255/31 ,  C07C255/40 ,  C07C255/45 ,  C07C255/53 ,  C07C255/56 ,  C07D307/06 ,  C07D307/54 ,  C07D307/56 ,  C07D333/04 ,  C07D333/22 ,  C07D333/24 ,  C07D307/36 ,  C07C57/00 ,  C07C63/06

    CPC分类号： C07C255/00 ,  C07C253/14 ,  C07D307/54 ,  C07D333/24

    摘要： There are prepared acyl cyanides of the formula ##STR1## where R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and which also can be substituted by one or more phenyl groups or halogen atoms, preferably chlorine, or R is preferably a cycloalkyl group having 3 to 8 carbon atoms, preferably cyclopropyl, which can have one or more 1 to 3 carbon atom alkyl or halogen, preferably chlorine, substituents wherein in all of the above set forth substitutions the halogen atoms and the phenyl groups are not on the carbon atom adjacent to the carbonyl group or R is a substituted phenyl group, a naphthyl group, a substituted naphthyl group or a five membered heterocyclic group, e.g., furyl, thienyl or alkyl substituted thienyl, wherein the substituents on the phenyl or naphthyl are halogen atoms, nitro groups or alkyl or alkoxy groups having 1 to 5 carbon atoms. The process comprises reacting an acyl halide of the formulaR--CO--Hal (II)in which R is as defined above and Hal is a chlorine or bromine atom, with a mixture consisting of about 0.1 to 5 equivalents of the alkali metal cyanide and about 0.05 to 2 equivalents of the copper (I) salt at a temperature of about 50.degree. to 180.degree. C in the presence of a carboxylic acid nitrile inert under the reaction conditions employed. Certain of the compounds are novel per se.

    摘要翻译： 制备式（I）的酰基氰化物，其中R是具有1至18个碳原子，优选1至10个碳原子的直链或支链烷基，并且也可被一个或多个苯基取代 或卤素原子，优选氯，或R优选为具有3至8个碳原子的环烷基，优选环丙基，其可以具有一个或多个1至3个碳原子的烷基或卤素，优选氯，取代基，其中在上述所有 卤素原子和苯基不在与羰基相邻的碳原子上，或者R是取代的苯基，萘基，取代的萘基或五元杂环基，例如呋喃基，噻吩基或烷基 取代的噻吩基，其中苯基或萘基上的取代基是卤素原子，硝基或具有1-5个碳原子的烷基或烷氧基。 该方法包括使式R-CO-Hal（II）的酰卤，其中R如上定义，Hal是氯或溴原子，与由约0.1至5当量的碱金属氰化物和 在约50至180℃的温度下，在所用反应条件下在惰性的羧酸腈存在下，约0.05-2当量的铜（I）盐。 某些化合物本身是新颖的。

    Substituted cyclopropyl glyoxylnitriles
    4.
    发明授权
    Substituted cyclopropyl glyoxylnitriles 失效
    取代的环丙基乙醛腈

    公开(公告)号：US4122116A

    公开(公告)日：1978-10-24

    申请号：US880483

    申请日：1978-02-23

    申请人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    发明人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    IPC分类号： C07C255/45 ,  C07C255/56 ,  C07D307/54 ,  C07C61/00 ,  C07C51/00 ,  C07C121/46

    CPC分类号： C07C253/14 ,  C07D307/54

    摘要： There are prepared acyl cyanides of the formula ##STR1## where R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and which also can be substituted by one or more phenyl groups or halogen atoms, preferably chlorine, or R is preferably a cycloalkyl group having 3 to 8 carbon atoms, preferably cyclopropyl, which can have one or more 1 to 3 carbon atoms alkyl or halogen, preferably chlorine, substituents wherein in all of the above set forth substitutions the halogen atoms and the phenyl groups are not on the carbon atom adjacent to the carbonyl group or R is a substituted phenyl group, a naphthyl group, a substituted naphthyl group or a five membered heterocyclic group, e.g., furyl, thienyl or alkyl substituted thienyl wherein the substituents on the phenyl or naphthyl are halogen atoms, nitro groups or alkyl or alkoxy groups having 1 to 5 carbon atoms. The process comprises reacting and acyl halide of the formulaR--CO--Hal (II)in which R is as defined above and Hal is a chlorine or bromine atoms, with CuCN at a temperature of about 50.degree. to 180.degree. C in the presence of a carboxylic acid nitrile inert under the reaction conditions, there being employed about 1 to 10 parts by weight of the carboxylic acid nitrile and about 0.5 to 20 parts by weight of at least one organic solvent which is inert under the reaction conditions. Certain of the compounds are novel per se.

    摘要翻译： 制备式（I）的酰基氰化物，其中R是具有1至18个碳原子，优选1至10个碳原子的直链或支链烷基，并且也可被一个或多个苯基取代 或卤素原子，优选氯，或R优选为具有3至8个碳原子的环烷基，优选环丙基，其可以具有一个或多个1至3个碳原子的烷基或卤素，优选氯，取代基，其中在所有上述定义 卤素原子和苯基不在与羰基相邻的碳原子上，或者R是取代的苯基，萘基，取代的萘基或五元杂环基，例如呋喃基，噻吩基或烷基 取代的噻吩基，其中苯基或萘基上的取代基是卤素原子，硝基或具有1至5个碳原子的烷基或烷氧基。 该方法包括在存在下将式R-CO-Hal（II）的酰卤与其中R定义如上和Hal为氯或溴原子的酰卤与CuCN在约50-180℃的温度下反应， 的在反应条件下为惰性的羧酸腈，使用约1-10重量份的羧酸腈和约0.5-20重量份的至少一种在反应条件下为惰性的有机溶剂。 某些化合物本身是新颖的。

    Process for the production of acyl cyanides (A)
    5.
    发明授权
    Process for the production of acyl cyanides (A) 失效
    酰基氰的制备方法（A）

    公开(公告)号：US4108877A

    公开(公告)日：1978-08-22

    申请号：US802944

    申请日：1977-06-02

    申请人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    发明人： Herbert Klenk ,  Heribert Offermanns ,  Werner Schwarze

    IPC分类号： C07C67/00 ,  C07C253/00 ,  C07C253/14 ,  C07C255/16 ,  C07C255/17 ,  C07C255/18 ,  C07C255/31 ,  C07C255/40 ,  C07C255/45 ,  C07C255/53 ,  C07C255/56 ,  C07D307/06 ,  C07D307/38 ,  C07D307/46 ,  C07D307/54 ,  C07D307/56 ,  C07D333/16 ,  F28F3/00 ,  C07D307/36 ,  C07C57/00 ,  C07C63/06

    CPC分类号： C07C255/00 ,  C07C253/14 ,  C07D307/54

    摘要： There are prepared acyl cyanides of the formula ##STR1## where R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and which also can be substituted by one or more phenyl groups or halogen atoms, preferably chlorine, or R is preferably a cycloalkyl group having 3 to 8 carbon atoms, preferably cyclopropyl, which can have one or more 1 to 3 carbon atom alkyl or halogen, preferably chlorine, substituents wherein in all of the above set forth substitutions the halogen atoms and the phenyl groups are not on the carbon atom adjacent to the carbonyl group or R is a substituted phenyl group, a naphthyl group, a substituted naphthyl group or a five membered heterocyclic group, e.g., furyl, thienyl or alkyl substituted thienyl, wherein the substituents on the phenyl or naphthyl are halogen atoms, nitro groups or alkyl or alkoxy groups having 1 to 5 carbon atoms. The process comprises reacting an acyl halide of the formulaR -- Co -- Hal (II)in which R is as defined above and Hal is a chlorine or bromine atom, with CuCN at a temperature of about 50.degree. to 180.degree. C in the presence of a carboxylic acid nitrile inert under the reaction conditions, there being employed about 1 to 10 parts by weight of the carboxylic acid nitrile and about 0.5 to 20 parts by weight of at least one organic solvent which is inert under the reaction conditions. Certain of the compounds are novel per se.

    摘要翻译： 制备式（I）的酰基氰化物，其中R是具有1至18个碳原子，优选1至10个碳原子的直链或支链烷基，并且也可被一个或多个苯基取代 或卤素原子，优选氯，或R优选为具有3至8个碳原子的环烷基，优选环丙基，其可以具有一个或多个1至3个碳原子的烷基或卤素，优选氯，取代基，其中在上述所有 卤素原子和苯基不在与羰基相邻的碳原子上，或者R是取代的苯基，萘基，取代的萘基或五元杂环基，例如呋喃基，噻吩基或烷基 取代的噻吩基，其中苯基或萘基上的取代基是卤素原子，硝基或具有1-5个碳原子的烷基或烷氧基。 该方法包括使式R-Co-Hal（II）的酰卤，其中R如上所定义，Hal是氯或溴原子，与CuCN在约50-180℃的温度下反应， 的在反应条件下为惰性的羧酸腈，使用约1-10重量份的羧酸腈和约0.5-20重量份的至少一种在反应条件下为惰性的有机溶剂。 某些化合物本身是新颖的。

    Process for the production of alpha-ketocarboxylic acid amides and cycloaliphatic products
    6.
    发明授权
    Process for the production of alpha-ketocarboxylic acid amides and cycloaliphatic products 失效
    制备α-酮羧酸酰胺和脂环族产物的方法

    公开(公告)号：US4161491A

    公开(公告)日：1979-07-17

    申请号：US802903

    申请日：1977-06-02

    申请人： Axel Kleemann ,  Herbert Klenk ,  Werner Schwarze

    发明人： Axel Kleemann ,  Herbert Klenk ,  Werner Schwarze

    IPC分类号： C07C231/06 ,  C07C20060101 ,  C07C67/00 ,  C07C231/00 ,  C07C235/72 ,  C07C235/80 ,  C07C102/02 ,  C07C102/08 ,  C07C103/127 ,  C07C103/19

    CPC分类号： C07C231/06

    摘要： There are prepared .alpha.-ketocarboxylic acid amides of the formula ##STR1## where R is hydrogen, R.sub.1 and R.sub.2 are the same or different, R.sub.1 is alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms, and R.sub.2 is hydrogen, alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms or ##STR2## together is a cycloalkyl group of 3 to 8 carbon atoms which can be substituted by one or more 1 to 5 carbon atom alkyl groups or by one or more halogen atoms, preferably chlorine atoms, with the proviso that when ##STR3## form a cycloalkyl group then R can also be alkyl of 1 to 5 carbon atoms. The process comprises saponifying an acyl cyanide of the formula ##STR4## in which R, R.sub.1 and R.sub.2 are as defined above in an organic solvent or mixture of such solvents which is liquid and inert under the reaction conditions, first with gaseous hydrogen chloride and then treating with water at a temperature of about -70.degree. C. to about +70.degree. C. and then isolating the .alpha.-ketocarboxylic acid amide in conventional manner. Several of the cyclic .alpha.-ketocarboxylic acid amides are new compounds.

    摘要翻译： 制备式（I）的α-酮羧酸酰胺，其中R是氢，R 1和R 2相同或不同，R 1是1至18个碳原子的烷基或卤代烷基，优选氯代烷基，其为1至18 碳原子，R 2是氢，1至18个碳原子的烷基或具有1至18个碳原子的卤代烷基，优选氯代烷基，或者“IMAGE”是3-8个碳原子的环烷基，其可以被一个或多个 1至5个碳原子的烷基或一个或多个卤素原子，优选氯原子，条件是当形成环烷基时，则R也可以是1至5个碳原子的烷基。 该方法包括在其中R 1，R 2和R 2如上所定义的式（Ⅶ）的酰基氰在有机溶剂或这种在反应条件下为液体和惰性的溶剂的混合物中，首先用气态氢 然后在约-70℃至约+70℃的温度下用水处理，然后以常规方式分离α-酮羧酸酰胺。 几种环状α-酮羧酸酰胺是新的化合物。