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    Process for the preparation of cyclohexanedionecarboxylic acid derivatives
    1.
    发明授权
    Process for the preparation of cyclohexanedionecarboxylic acid derivatives 失效
    环己二酸羧酸衍生物的制备方法

    公开(公告)号：US4803268A

    公开(公告)日：1989-02-07

    申请号：US008445

    申请日：1987-01-29

    申请人： Hans-Georg Brunner ,  Urs Muller

    发明人： Hans-Georg Brunner ,  Urs Muller

    IPC分类号： A01N37/42 ,  C07C51/00 ,  C07C51/347 ,  C07C62/00 ,  C07C62/38 ,  C07C67/00 ,  C07C67/22 ,  C07C69/757 ,  C07C201/00 ,  C07C205/43 ,  C07C231/00 ,  C07C231/12 ,  C07C233/12 ,  C07C235/82 ,  C07C253/00 ,  C07C255/55 ,  C07C255/60 ,  C07C313/00 ,  C07C323/12 ,  C07C323/40 ,  C07D295/18 ,  C07D295/185 ,  C07D279/10

    CPC分类号： C07D295/185 ,  C07C323/00 ,  C07C51/347

    摘要： The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C. to room temperature, zinc chloride, an equimolar amount, with respect to the carboxylic acid derivative of formula III, of a 3,5-cyclohexanedione-1-carboxylic acid derivative of formula II ##STR3## wherein A is an ester or amide radical, and, dropwise, an amine, and, after acidifying the reaction mixture with an aqueous acid, isolating the resultant 4-acyl-3,5-cyclohexanedione-1-carboxylic acid derivative of formula I ##STR4## by extraction. Said cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.

    摘要翻译： 本发明涉及一种用于制备式I的环己二酸羧酸衍生物的新型优化方法，其可以在单一容器中进行，提供非常好的产率，该方法包括加热式III的反应性羧酸衍生物 （III）其中X是卤化物，烷基磺酸或芳基磺酸基团或在惰性有机溶剂中与碱金属氰化物或氰化铜形成酸酐而R1是烷基或环烷基所必需的分子基团 ，得到混合物，然后在0℃至室温的温度下连续加入所述混合物，相对于式III的羧酸衍生物，等摩尔量的氯化锌为3 （II）的5-环己二酮-1-羧酸衍生物其中A是酯或酰胺基，并逐滴加入胺，并且在用酸水溶液酸化反应混合物后， 通过萃取分离得到式I的所得4-酰基-3,5-环己二酮-1-羧酸衍生物（I）图像+ TR图像。 所述环己二酸羧酸衍生物具有除草和植物生长调节性质。

    Herbicidally, acaricidally and insecticidally active pyrazolidine compounds
    3.
    发明授权
    Herbicidally, acaricidally and insecticidally active pyrazolidine compounds 失效
    除草剂，杀螨剂和杀虫活性吡唑烷化合物

    公开(公告)号：US5506193A

    公开(公告)日：1996-04-09

    申请号：US119103

    申请日：1993-09-17

    申请人： Frederik Cederbaum ,  Hans-Georg Brunner ,  Manfred Boger

    发明人： Frederik Cederbaum ,  Hans-Georg Brunner ,  Manfred Boger

    IPC分类号： A01N43/56 ,  A01N43/90 ,  C07C251/76 ,  C07C251/78 ,  C07C255/65 ,  C07C271/62 ,  C07C281/02 ,  C07C281/04 ,  C07C317/44 ,  C07C323/62 ,  C07D231/08 ,  C07D231/32 ,  C07D231/34 ,  C07D231/36 ,  C07D237/04 ,  C07D401/04 ,  C07D401/12 ,  C07D487/04

    CPC分类号： C07D401/12 ,  A01N43/56 ,  A01N43/90 ,  C07C251/76 ,  C07C251/78 ,  C07C281/02 ,  C07C281/04 ,  C07D231/32 ,  C07D237/04 ,  C07D487/04

    摘要： The present invention relates to herbicidally, acaricidally and insecticidally active pyrazolidine-3,5-diones of the formula I ##STR1## in which R.sub.1 is ##STR2## R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; orR.sub.2 and R.sub.3 together are a --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, --CH.sub.2 --CH.dbd.CH-- or --(CH.sub.2).sub.2 --CH.dbd.CH-- bridge which is unsubstituted or up to trisubstituted by C.sub.1 -C.sub.4 alkyl;n is 0; 1; 2; 3; or 4;m is 0; or 1; the total of m and n being less than, or equal to, 4; theR.sub.4 radicals independently of one another are halogen; nitro; cyano, C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.10 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; C.sub.3 -C.sub.6 alkenyloxy; C.sub.1 -C.sub.4 alkoxy-C.sub.2 -.sub.4 alkoxy; C.sub.3 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.4 alkylcarbonyl; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.4 alkylthio; C.sub.1 -C.sub.4 alkylsulfinyl; C.sub.1 -C.sub.4 alkylsulfonyl; amino; mono-C.sub.1 -C.sub.4 alkylamino; di-C.sub.1 -C.sub.4 alkylamino;R.sub.5 is ##STR3## X is oxygen; sulfur; CH.sub.2 ; or NR.sub.7 ; o is 0; 1; 2; or 3;R.sub.6 radicals independently of one another are C.sub.1 -C.sub.4 alkyl; halogen; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 haloalkoxy; C.sub.1 -C.sub.4 alkoxy; nitro; cyano; C.sub.1 -C.sub.4 alkoxycarbonyl; amino; mono-C.sub.1 -C.sub.4 alkylamino; or di-C.sub.1 -C.sub.4 alkylamino; andR.sub.7 is hydrogen; C.sub.1 -C.sub.4 alkyl; formyl; or C.sub.1 -C.sub.4 alkylcarbonyl;the acid addition salts thereof, as well as processes for their preparation, and novel intermediates for these processes. The invention furthermore relates to herbicidally, acaricidally or insecticidally active compositions as well as to methods for controlling weeds, Acarina or insects.

    摘要翻译： PCT No.PCT / EP92 / 00452 Sec。 371日期：1993年9月17日 102（e）日期1993年9月17日PCT提交1992年3月2日PCT公布。 出版物WO92 / 本发明涉及除草，杀螨剂和杀虫活性的式I（I）的吡唑烷-3,5-二酮，其中R 1和R 3独立地为 彼此是C1-C6烷基; C 3 -C 6烯基; 或C 3 -C 6炔基; 或者R 2和R 3一起是 - （CH 2）3 - ， - （CH 2）4 - ， - CH 2 -CH = CH-CH 2 - ， - CH 2 -CH = CH-或 - （CH 2）2 -CH = 其是未取代的或被C1-C4烷基三取代; n为0; 1; 2; 3; 或4; m为0; 或1; m和n的总和小于或等于4; R4基彼此独立地是卤素; 硝基 氰基，C 1 -C 4烷基; C 1 -C 4卤代烷基; C1-C10烷氧基; C1-C4卤代烷氧基; C3-C6链烯氧基; C1-C4烷氧基-C2-4烷氧基; C3-C6炔氧基; C1-C4烷基羰基; C1-C4烷氧基羰基; C 1 -C 4烷硫基; C 1 -C 4烷基亚磺酰基; C 1 -C 4烷基磺酰基; 氨基; 单C 1 -C 4烷基氨基; 二-C 1 -C 4烷基氨基; R5是氧; 硫; CH2; 或NR7; o是0; 1; 2; 或3; R 6基彼此独立地是C 1 -C 4烷基; 卤素; C 1 -C 4卤代烷基; C1-C4卤代烷氧基; C1-C4烷氧基; 硝基 氰基; C1-C4烷氧基羰基; 氨基; 单C 1 -C 4烷基氨基; 或二-C 1 -C 4烷基氨基; 而R7是氢; C 1 -C 4烷基; 甲酰基 或C 1 -C 4烷基羰基; 其酸加成盐及其制备方法，以及这些方法的新型中间体。 本发明还涉及除草，杀螨剂或杀虫活性组合物以及控制杂草，螨虫或昆虫的方法。

    Novel herbicidally active n-phenyl-azoles
    4.
    发明授权
    Novel herbicidally active n-phenyl-azoles 失效
    新型除草活性的n-苯基 - 唑类

    公开(公告)号：US5049181A

    公开(公告)日：1991-09-17

    申请号：US440007

    申请日：1989-11-21

    申请人： Georg Pissiotas ,  Hans Moser ,  Hans-Georg Brunner

    发明人： Georg Pissiotas ,  Hans Moser ,  Hans-Georg Brunner

    IPC分类号： A01N43/90 ,  C07D231/12 ,  C07D231/22 ,  C07D231/56 ,  C07D401/12 ,  C07D403/12 ,  C07D405/12 ,  C07D409/12 ,  C07D417/12 ,  C07D471/04 ,  C07D487/04 ,  C07D521/00

    CPC分类号： C07D249/08 ,  C07D231/12 ,  C07D231/56 ,  C07D233/56 ,  C07D401/12 ,  C07D403/12 ,  C07D405/12 ,  C07D409/12 ,  C07D417/12 ,  C07D471/04 ,  C07D487/04

    摘要： The invention relates to novel phenyl substituted pyrazoles, 4,5,6,7-tetrahydro-indazoles, 2,4,5,6-tetrahydro-cyclopenta[c]pyrazoles, octahydroimidazo[1,5-a]pyridin-1,3-diones, hexahydro-1H-pyrrolo[1,2-c]-imidazol-1,3-diones, hexahydro-1H-1,2,4-triazolo[1,2-a]pyridazin-1,3-diones and tetrahydro-1H,5H-pyrazolo[1,2-a][1,2,4]triazol-1,3-diones which have phenyl-substituted in the 2-position, herbicidal activity. It furthermore relates to agrochemical compositions, which contain these compounds, to their use for controlling undesirable plant-growth and for processes for the preparation of the compounds according to this invention.The novel N-Phenyl-azoles correspond to the formula I ##STR1## R.sup.1 is hydrogen or halogen; R.sup.2 is halogen;A is a straight-chain or branched C.sub.1 -C.sub.4 -alkylene chain;n is zero or 1;Q is --S(O).sub.m --R.sup.3 ; di-C.sub.1 -C.sub.4 -alkylamino; a 5- or 6-membered heterocyclus, that is bound via a carbon or nitrogen atom and which contains 1 to 3 hetero-atoms selected from the group consisting of N, O and S, which heterocycles can be fused to a benzene ring and mono- or disubstituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -dialkylamino, hydroxy or carboxyl;R.sup.3 is C.sub.1 -C.sub.10 -alkyl; ##STR2## m is zero, 1 or 2; R.sup.4 is C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy;p is zero 1, 2, or 3;X is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl;Y is C.sub.1 -C.sub.4 -alkyl; orX and Y form together a --(CH.sub.2).sub.q -chain, which is optionally mono- or disubstituted by methyl;q is three or four; andZ is halogen, methyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio; under inclusion of the salts of these azoles with acids, bases and complex-building substances.

    摘要翻译： 本发明涉及新的苯基取代的吡唑，4,5,6,7-四氢 - 吲唑，2,4,5,6-四氢 - 环戊二烯并[c]吡唑，八氢咪唑并[1,5-a]吡啶-1,3 六氢-1H-吡咯并[1,2-c] - 咪唑-1,3-二酮，六氢-1H-1,2,4-三唑并[1,2-a]哒嗪-1,3-二酮和 四氢-1H，5H-吡唑并[1,2-a] [1,2,4]三唑-1,3-二酮，其具有2位的苯基取代，除草活性。 此外，它还涉及含有这些化合物的农药组合物，其用于控制​​不期望的植物生长和根据本发明的化合物的制备方法。 新型N-苯基 - 吡咯对应于式I（I）其中R1是氢或卤素; R2是卤素; A是直链或支链的C 1 -C 4 - 亚烷基链; n为零或1; Q是-S（O）m -R 3; 二-C 1 -C 4烷基氨基; 通过碳或氮原子结合并含有1至3个选自N，O和S的杂原子的5-或6-元杂环，该杂环可以与苯环稠合并且单 或被卤素，C 1 -C 4 - 烷基，C 1 -C 3 - 卤代烷基，C 1 -C 3 - 烷氧基，C 1 -C 3 - 卤代烷氧基，C 1 -C 3 - 二烷基氨基，羟基或羧基二取代; R3是C1-C10-烷基; m是零，1或2; R4是C1-C4-烷基，卤素或C1-C4-烷氧基; p为零1,2或3; X是氢，卤素或C 1 -C 4 - 烷基; Y是C 1 -C 4 - 烷基; 或X和Y一起形成 - （CH 2）q链，其任选被甲基单或二取代; q是三四个; Z为卤素，甲基，C 1 -C 6 - 烷氧基或C 1 -C 6 - 烷硫基; 在这些唑类的盐类与酸，碱和复合物构成物质之间。

    3H imidazo[1'2':2,2]pyrrolo[3,4-b]pyridine-2,5-dione, useful as herbicidal agents
    5.
    发明授权
    3H imidazo[1'2':2,2]pyrrolo[3,4-b]pyridine-2,5-dione, useful as herbicidal agents 失效
    3H咪唑并[1'2“：2,2]吡咯并[3,4-b]吡啶-2,5-二酮，可用作除草剂

    公开(公告)号：US4726838A

    公开(公告)日：1988-02-23

    申请号：US936216

    申请日：1986-12-01

    申请人： Dieter Durr ,  Hans-Georg Brunner ,  Henry Szczepanski

    发明人： Dieter Durr ,  Hans-Georg Brunner ,  Henry Szczepanski

    IPC分类号： A01N43/90 ,  C07D471/14 ,  A01N43/36 ,  A01N43/40

    CPC分类号： C07D471/14 ,  A01N43/90

    摘要： This continuation-in-part is directed to novel pyridine compounds of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The compounds are of formula I ##STR1## wherein each of X, Y and Z independently of one another is hydrogen or a C.sub.1 -C.sub.4 alkyl group, or two adjacent substituents together also form a saturated or unsaturated 3- or 4-membered alkylene chain or alkenyl chain, each of which chains may in turn by substituted by one to four C.sub.1 -C.sub.4 alkyl groups and R is a C.sub.1 -C.sub.4 nitroalkyl group.

    摘要翻译： 这部分继续部分是针对以下式I的新型吡啶化合物在芽前和芽后具有良好的选择性除草性质，并且还影响或抑制植物生长。 所述化合物具有式I（I）其中X，Y和Z各自独立地为氢或C 1 -C 4烷基，或两个相邻取代基一起也形成饱和或不饱和的3-或4- 每个链可以依次被1-4个C1-C4烷基取代，R是C1-C4烷基。

    Cyclohexenonecarboxylic acid derivatives with herbicidal and plant growth regulating properties
    6.
    发明授权
    Cyclohexenonecarboxylic acid derivatives with herbicidal and plant growth regulating properties 失效
    环己烯酸衍生物具有除草和植物生长调节特性

    公开(公告)号：US4640706A

    公开(公告)日：1987-02-03

    申请号：US714133

    申请日：1985-03-20

    申请人： Hans-Georg Brunner

    发明人： Hans-Georg Brunner

    IPC分类号： C07D295/18 ,  A01N37/08 ,  A01N37/18 ,  A01N37/22 ,  A01N37/34 ,  A01N37/50 ,  A01N41/04 ,  C07C67/00 ,  C07C239/00 ,  C07C251/44 ,  C07C301/00 ,  C07C303/28 ,  C07C309/63 ,  C07C313/00 ,  C07C323/55 ,  C07C323/60 ,  C07D295/192 ,  A01N31/06 ,  A01N33/24 ,  C07C131/08

    CPC分类号： C07D295/192 ,  A01N37/50

    摘要： Novel cyclohexenonecarboxylic acid derivatives exhibit herbicidal and plant growth regulating activity.The cyclohexenonecarboxylic derivatives are of the formula I ##STR1## wherein A is an aliphatic or aromatic alcohol, or is an amino group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano, or is a heterocyclic amino group which is unsubstituted or substituted,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,B is an aliphatic or aromatic radical or is an aliphatic or aromatic carbonyl or sulfonyl group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano.The compounds are suitable for selectively controlling grasses in crops of useful plants.

    摘要翻译： 新型环己烯羧酸衍生物具有除草和植物生长调节活性。 环己烯羧酸衍生物具有式I（I）其中A是脂族或芳族醇，或是可以被卤素，低级烷氧基，低级烷硫基，硝基或氰基取代的氨基，或是杂环氨基 基团是未取代或取代的，R是C 1 -C 6烷基或C 3 -C 6环烷基，各自未被取代或被卤素，C 1 -C 4烷氧基或C 1 -C 4烷硫基取代，R 1是C 1 -C 6烷基，C 1 -C 6卤代烷基，C 3 -C 6烯基，C 3 -C 6卤代烯基或 C 3 -C 6炔基，B是脂族或芳族基团，或者是可被卤素，低级烷氧基，低级烷硫基，硝基或氰基取代的脂族或芳族羰基或磺酰基。 该化合物适用于有选择地控制有用植物作物中的草。

    Benzo-1,2,3-thiadiazole derivatives
    10.
    发明授权
    Benzo-1,2,3-thiadiazole derivatives 失效
    苯并-1,2,3-噻二唑衍生物

    公开(公告)号：US5248683A

    公开(公告)日：1993-09-28

    申请号：US893292

    申请日：1992-06-04

    申请人： Hans-Georg Brunner ,  Walter Kunz ,  Rolf Schurter

    发明人： Hans-Georg Brunner ,  Walter Kunz ,  Rolf Schurter

    IPC分类号： A01N43/82 ,  A01N43/828 ,  C07D285/14 ,  C07D405/06 ,  C07D409/06 ,  C07D417/06

    CPC分类号： C07D285/14 ,  A01N43/82 ,  C07D405/06 ,  C07D409/06 ,  C07D417/06

    摘要： Compounds of the formula ##STR1## in which A.sub.1 and A.sub.2 independently of one another are CO--C.sub.1 -C.sub.4 alkyl, COO--C.sub.1 -C.sub.4 alkyl, CO--CF.sub.3, CO--N(R).sub.2 or cyano;A.sub.1 and A.sub.2 together are CO(X).sub.n --C.sub.1 -C.sub.3 alkylene-(X).sub.n CO, CO(X).sub.n --C.sub.1 -C.sub.3 alkylene-(X).sub.n CO which is substituted by C.sub.1 -C.sub.4 alkyl, COOR, CON(R).sub.2, cyano or phenyl, it being possible for the phenyl ring, in turn, to be substituted by halogen, methyl, trifluoromethyl, methoxy, nitro or cyano; CO--N(R)--CO--N(R)--CO;R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl;X is oxygen, sulfur or N(CH.sub.3);X.sub.1, X.sub.2 and X.sub.3 independently of one another are hydrogen, halogen, methyl, methylthio, methoxy or nitro;n is 0 or 1;including the salts of the compounds of the formula I with agriculturally acceptable organic or inorganic bases, and including the metal complexes; have valuable microbicidal properties.The novel compounds can be used in crop protection for preventing the attack of crop plants by phytopathogenic microorganisms and for the control of these pests.

    摘要翻译： 其中A 1和A 2彼此独立的式“IMAGE”的化合物是CO-C 1 -C 4烷基，COO-C 1 -C 4烷基，CO-CF 3，CO-N（R）2或氰基; A1和A2一起是被C1-C4烷基，COOR，CON（R）2取代的CO（X）n-C1-C3亚烷基 - （X）nCO，CO（X）n-C1-C3亚烷基 - （X） 氰基或苯基，苯环可以被卤素，甲基，三氟甲基，甲氧基，硝基或氰基取代; CO-N（R）-CO-N（R）-CO; R是氢，C 1 -C 6烷基，C 3 -C 6烯基或C 3 -C 6炔基; X是氧，硫或N（CH 3）; X1，X2和X3彼此独立地是氢，卤素，甲基，甲硫基，甲氧基或硝基; n为0或1; 包括式I化合物与农业上可接受的有机或无机碱的盐，并包括金属络合物; 具有有价值的杀菌特性。 新型化合物可用于作物保护，以防止植物病原微生物侵袭作物和控制这些害虫。