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    Herbicides containing substituted 2-aminothiophenes
    1.
    发明授权
    Herbicides containing substituted 2-aminothiophenes 失效

    公开(公告)号：US5422335A

    公开(公告)日：1995-06-06

    申请号：US70389

    申请日：1993-06-07

    申请人： Helmut Hagen ,  Gerhard Nilz ,  Helmut Walter ,  Andreas Landes

    发明人： Helmut Hagen ,  Gerhard Nilz ,  Helmut Walter ,  Andreas Landes

    IPC分类号： A01N25/32 ,  A01N35/06 ,  A01N39/02 ,  A01N43/10 ,  C07D333/38 ,  C07D333/68 ,  C07D333/70 ,  C07D409/04 ,  C07D409/12 ,  C07D417/12 ,  A01N43/12 ,  A01N47/24 ,  C07D333/54

    CPC分类号： C07D409/04 ,  A01N25/32 ,  C07D333/38 ,  C07D333/68 ,  C07D409/12 ,  C07D417/12

    摘要： A herbicidal composition containing one or more substituted 2-aminothiophenes of the formula I ##STR1## where R.sup.1 and R.sup.2 together from a C.sub.4 -alkylene chain to which a benzene ring may be fused,R.sup.3 is --CN or CX--R.sup.6, where R.sup.6 is hydroxyl, C.sub.1 -C.sub.4 -alkoxy or amino,R.sup.4 is hydrogen or a phenyl group which may carry one or two nitro radicals,--PO(OR.sup.8).sub.2, --CX--R.sup.9, --SO.sub.2 R.sup.10, --CX--N(H) --CO--R.sup.8 or --CX--N(R.sup.7)--SO.sub.2 --R.sup.11,whereR.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl groupR.sup.9 is C.sub.1 -C.sub.20 -alkyl, partially or completely halogenated C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.6 -cycloalkyl, or amino, C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkylamino, phenyl or phenylamino, where the aromatic moiety may carry at least one of nitro and halogen;R.sup.10 is C.sub.1 -C.sub.4 -alkyl or phenyl, which may carry one C.sub.1 -C.sub.4 -alkyl radical;R.sup.11 is pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl, where the heterocyclic structures may carry one C.sub.1 -C.sub.4 -group;R.sup.5 is hydrogen;orR.sup.4 and R.sup.5 together form a group .dbd.CR.sup.12 R.sup.13 or --CO--W--CO--, where R.sup.12 is hydrogen, amino, C.sub.1 -C.sub.4 -alkylamino or C.sub.3 -C.sub.8 -cycloalkylamino;R.sup.13 is amino, C.sub.3 -C.sub.8 -cycloalkylamino, phenyl or pyridyl, where the two last mentioned substituents may carry at least one halogen or nitro radicals;W is an ethylene or ethenylene bridge, or a 6-membered 1,2-C-bonded aromatic bridge where these bridge members may carry, on each substitutable carbon atom, at least one halogena 5-membered or 6-membered 1,2-C-bonded cycloalkylene or cycloalkenylene bridge,and the basic salts of the compounds I in which R.sup.3 is hydroxycarbonyl or hydroxythiocarbonyl, and the acidic salts of the compounds I which contain a basic nitrogen atom, as antagonistic compoundsand one or more herbicidal active ingredients from the group consisting ofthe cyclohexenone derivatives of the formula III ##STR2##

    Substituted 5-aminopyrazoles
    3.
    发明授权
    Substituted 5-aminopyrazoles 失效

    公开(公告)号：US5486618A

    公开(公告)日：1996-01-23

    申请号：US70386

    申请日：1993-06-07

    申请人： Helmut Hagen ,  Gerhard Nilz ,  Helmut Walter ,  Andreas Landes

    发明人： Helmut Hagen ,  Gerhard Nilz ,  Helmut Walter ,  Andreas Landes

    IPC分类号： A01N43/56 ,  A01N25/32 ,  C07D231/38 ,  C07D231/40 ,  C07D309/12 ,  C07D335/02 ,  C07D403/04 ,  C07D231/00

    CPC分类号： C07D403/04 ,  A01N25/32 ,  C07D231/40

    摘要： Substituted 5-aminopyrazoles I ##STR1## where R.sup.1 is C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -hydroxyalkyl, phenyl which may carry 1-3 of the following radicals: halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or --NR.sup.6 R.sup.7, and which may additionally carry a number of halogen atoms so that the total number of radicals is 5, R.sup.6 and R.sup.7 are each H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, R.sup.3 is CN, --CO--R.sup.8 or --CS--R.sup.8, R.sup.8 is OH, C.sub.1 -C.sub.4 -alkoxy, NH.sub.2, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, R.sup.4 and R.sup.5 are each H, C.sub.1 -C.sub.4 -alkyl, PX(OR.sup.9).sub.2, --SO.sub.2 --R.sup.9, --CX--R.sup.10, --CX--NH--CY--R.sup.9 or CX--NH--SO.sub.2 --R.sup.11, X and Y are each O or S, R.sup.9 is one of the substituents R.sup.1, R.sup.10 is C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.4 -alkoxy, unsubstituted or substituted phenyl or unsubstituted or substituted NH.sub.2, R.sup.11 is NH.sub.2, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, pyrrolidinyl, piperidinyl or morpholinyl, R.sup.4 and R.sup.5 together form a group .dbd.CR.sup.12 R.sup.13 or --CO--W--CO--, R.sup.12 is H, NH.sub.2, C.sub.1 -C.sub.4 -alkylamino or C.sub.3 -C.sub.8 -cycloalkylamino, R.sup.13 is NH.sub.2, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkylamino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl and W is an unsubstituted or substituted ethylene or ethenylene bridge, an unsubstituted or substituted 5-membered or 6-membered 1,2-C-bonded aromatic or heteroaromatic bridge, or an unsubstituted or substituted 5-membered or 6-membered 1,2-C-bonded cycloalkylene or cycloalkenylene bridge,and the basic salts of the compounds I in which R.sup.3 is hydroxycarbonyl or hydroxythiocarbonyl, and the acidic salts of the compounds I which contain a basic nitrogen atom,with the exception of 1-phenyl- and 1-methyl-4-cyano-5-acylaminopyrazole, 1-methyl-4-cyano-5-(chloromethylcarbonylamino)-pyrazole, 1-methyl-4-cyano-5-(phenylcarbonylamino)-pyrazole, 1-methyl-4-cyano-5-(p-chlorophenylcarbonylamino)-pyrazole and the compounds I in which R.sup.1 is methyl, phenyl, 4-chlorophenyl or 4-nitrophenyl, R.sup.2 is hydrogen, methyl or trifluoromethyl, R.sup.3 is cyano and R.sup.4 and R.sup.5 are simultaneously hydrogen, and herbicides which contain 2-(4-hetaryloxy)- and 2-(4-aryloxy)-phenoxyacetic acid or -propionic acid derivatives and/or cyclohexenone derivatives as herbicidal active ingredients and substituted 5-aminopyrazoles I' or, in the case of acidic terminal groups or basic nitrogen atoms, the salts of I' as antidotes.

    Thiochromenone derivatives as antidotes, and herbicides containing them
    6.
    发明授权
    Thiochromenone derivatives as antidotes, and herbicides containing them 失效
    硫代苯并醌衍生物作为解毒剂，以及含有它们的除草剂

    公开(公告)号：US5378677A

    公开(公告)日：1995-01-03

    申请号：US5797

    申请日：1993-01-19

    申请人： Helmut Hagen ,  Peter Raatz ,  Helmut Walter ,  Andreas Landes

    发明人： Helmut Hagen ,  Peter Raatz ,  Helmut Walter ,  Andreas Landes

    IPC分类号： A01N25/32 ,  A01N43/18 ,  C07D335/06

    CPC分类号： C07D335/06 ,  A01N25/32 ,  A01N43/18

    摘要： Herbicidal agents containing at least one thiochromenone of the formula I ##STR1## where n is 1, 2, 3 or 4, and the radicals R.sup.3 may have different meanings when n is>1;R.sup.1 is hydrogen; cyano; halogen; substituted or unsubstituted alkyl, aryl or hetaryl;a group --XR.sup.4 or a group --COYR.sup.4, whereX is oxygen, sulfur and NR.sup.5,Y is oxygen and NR.sup.5,R.sup.4 is one of the following groups:hydrogen; formyl; alkyl; cycloalkyl; alkylcarbonyl; cycloalkylcarbonyl; alkylsulfonyl; cycloalkylsulfonyl;substituted or unsubstituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl;andR.sup.5 is hydrogen or substituted or unsubstituted alkyl, aryl or hetaryl;R.sup.2 is hydrogen; cyano; nitroso; nitro; halogen; substituted or unsubstituted alkyl, alkoxy, alkylthio, aryl or hetaryl;a group --NR.sup.4 R.sup.5 or a group --COYR.sup.4, whereY, R.sup.4 and R.sup.5 have the above meanings;R.sup.3 is hydrogen; cyano; halogen; substituted or unsubstituted alkyl, aryl or hetaryl;a group --YR.sup.4, a group --COYR.sup.4, a group --COR.sup.6 or a group --SO.sub.2 R.sup.7, whereY and R.sup.4 have the above meanings;R.sup.6 is one of the following groups:hydrogen; alkyl; cycloalkyl; substituted or unsubstituted aryl or hetaryl;andR.sup.7 is hydrogen; alkyl; cycloalkyl; substituted or unsubstituted aryl or hetaryl;or a group --NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 have the above meanings,and the plant-tolerated salts of those compounds I in which one or several of the substituents denote an acidic or basic group,and at least one herbicidal active ingredient.

    摘要翻译： 含有至少一种式I的图象的除草剂，其中n是1,2,3或4，当n大于1时，基团R 3可以具有不同的含义; R1是氢; 氰基; 卤素; 取代或未取代的烷基，芳基或杂芳基; 基团-XR4或基团-COYR4，其中X是氧，硫和NR5，Y是氧和NR5，R4是以下基团之一：氢; 甲酰基 烷基; 环烷基 烷基羰基; 环烷基羰基; 烷基磺酰基; 环烷基磺酰基; 取代或未取代的芳基，杂芳基，芳基羰基，杂芳基羰基，芳基磺酰基或杂芳基磺酰基; 和R 5是氢或取代或未取代的烷基，芳基或杂芳基; R2是氢; 氰基; 亚硝基 硝基 卤素; 取代或未取代的烷基，烷氧基，烷硫基，芳基或杂芳基; 基团-NR4R5或-COYR4基团，其中Y，R4和R5具有上述含义; R3是氢; 氰基; 卤素; 取代或未取代的烷基，芳基或杂芳基; 基团-YR4，-COYR4基团，基团-COR6或基团-SO2R7，其中Y和R4具有上述含义; R6是以下组之一：氢; 烷基; 环烷基 取代或未取代的芳基或杂芳基; 和R7是氢; 烷基; 环烷基 取代或未取代的芳基或杂芳基; 或-NR4R5基团，其中R4和R5具有上述含义，以及其中一个或几个取代基表示酸性或碱性基团的那些化合物I的植物耐受性盐和至少一种除草活性成分。

    2-amino-4-trichloropyridine derivatives
    7.
    发明授权
    2-amino-4-trichloropyridine derivatives 失效
    2-氨基-4-三氯吡啶衍生物

    公开(公告)号：US5216171A

    公开(公告)日：1993-06-01

    申请号：US681254

    申请日：1991-04-08

    申请人： Helmut Hagen ,  Hans Ziegler ,  Juergen Pfister ,  Gerhard Nilz ,  Gisela Lorenz ,  Juergen Dressel

    发明人： Helmut Hagen ,  Hans Ziegler ,  Juergen Pfister ,  Gerhard Nilz ,  Gisela Lorenz ,  Juergen Dressel

    IPC分类号： C05G3/08 ,  C07D213/74 ,  C07D213/75 ,  C07D213/76 ,  C07D401/04 ,  C07F9/58

    CPC分类号： C07D213/74 ,  C07D213/75 ,  C07D213/76 ,  C07D401/04 ,  C07F9/588 ,  Y02P60/218 ,  Y10S106/90

    摘要： 2-Amino-4-trichloromethylpyridines of the general formula I ##STR1## where R.sup.1 is hydrogen or C.sub.1 -C.sub.8 -alkyl,R.sup.2 is C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.4 -alkenyl or phenyl, benzyl or phenylsulfonyl,--CX--R.sup.3, --SO.sub.2 R.sup.3 or --PX(OR.sup.4).sub.2 orR.sup.1 and R.sup.2 together form .dbd.CR.sup.5 R.sup.6 or --CO--Z--CO--,X is oxygen or sulfur,R.sup.3 is C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.6 -alkenyl, amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, morpholino, piperidino, pyrazolidino or C.sub.1 -C.sub.8 -alkylcarbonylamino, substituted or unsubstituted phenylamino or benzylamino,R.sup.4 is C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -haloalkyl or substituted or unsubstituted phenyl,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl, or substituted or unsubstituted phenyl,R.sup.6 is substituted or unsubstituted phenyl,Z is substituted or unsubstituted ethylene which may be part of a substituted or unsubstituted cycloalkyl or cycloalkylene radical, substituted or unsubstituted ethenylene which may be part of a substituted or unsubstituted aromatic or heteroaromatic ring, and Z is not part of an unsubstituted phenyl radical, agriculturally useful salts thereof, processes for their preparation and the use thereof as nitrification inhibitors.

    摘要翻译： 通式I的2-氨基-4-三氯甲基吡啶其中R1是氢或C1-C8-烷基，R2是C1-C8-烷基，C5-C8-环烷基，C2-C4-烯基或苯基，苄基 或苯基磺酰基，-CX-R3，-SO2R3或-PX（OR4）2或R1和R2一起形成= CR5R6或-CO-Z-CO-，X是氧或硫，R3是C1-C20-烷基，C2- C 1 -C 6 - 烯基，氨基，C 1 -C 6 - 烷基氨基，二-C 1 -C 6烷基氨基，吗啉代，哌啶子基，吡唑烷基或C 1 -C 8烷基羰基氨基，取代或未取代的苯基氨基或苄基氨基，R 4是C 1 -C 8烷基， 卤代烷基或取代或未取代的苯基，R 5是氢，C 1 -C 4烷基或取代或未取代的苯基，R 6是取代或未取代的苯基，Z是可以是取代或未取代的环烷基或环亚烷基的一部分的取代或未取代的乙烯 取代或未取代的亚乙烯基，其可以是取代或未取代的芳族或杂芳族环的一部分，Z不是未取代的苯基的一部分，农业 其文化上有用的盐，其制备方法及其作为硝化抑制剂的用途。

    Cyanoquinoline compounds
    8.
    发明授权
    Cyanoquinoline compounds 失效
    氰基喹啉化合物

    公开(公告)号：US5565408A

    公开(公告)日：1996-10-15

    申请号：US423325

    申请日：1995-04-17

    申请人： Helmut Hagen ,  Juergen Pfister ,  Gunter Brill ,  Gerhard Nilz ,  Bruno Wuerzer ,  Karl-Otto Westphalen

    发明人： Helmut Hagen ,  Juergen Pfister ,  Gunter Brill ,  Gerhard Nilz ,  Bruno Wuerzer ,  Karl-Otto Westphalen

    IPC分类号： A01N43/42 ,  A01N25/32 ,  C07D215/48 ,  C07D215/50 ,  C07D215/54 ,  C07D215/56 ,  C07D401/04 ,  C07D401/06 ,  C07D401/12 ,  C07D401/14 ,  C07D413/04 ,  C07D413/14 ,  C07D417/04 ,  C07D215/28 ,  A01N43/40 ,  C07D215/26

    CPC分类号： C07D401/04 ,  A01N25/32 ,  C07D215/48 ,  C07D215/54 ,  C07D215/56 ,  C07D401/12

    摘要： Cyanoquinoline compounds Ia or Ib ##STR1## where R.sup.1 is CH.dbd.C(CN).sub.2 ; CH.dbd.N--N.dbd.CH--(5-quinolyl); methylsulfonyl; CH.dbd.NOH; halogen; hydroxyl; nitro; cyano; unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, pyrrolidinyl; piperidinyl; morpholinyl; thiomorpholinyl; unsubstituted or substituted phenyl, phenoxy, phenylthio, phenyldithiolyl, phenylsulfonyl or pyrrolyl;m is 0, 1, 2 or 3;R.sup.2 is hydrogen; hydroxyl; halogen; C.sub.1 -C.sub.4 -alkoxy; --NR.sup.3 R.sup.4 ; --NR.sup.5 --CXR.sup.6 or --N.dbd.CR.sup.7 R.sup.8 ;R.sup.3 is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl;R.sup.4 is a radical R.sup.3 ; C.sub.1 -C.sub.4 -alkylamino; di-C.sub.1 -C.sub.4 -alkylamino; substituted C.sub.1 -C.sub.4 -alkyl; CH.dbd.N--(3-cyano-2-quinolinyl); or R.sup.3 and R.sup.4 together form C.sub.4 - or C.sub.3 -alkylene which may be interrupted by a hetero atom, or unsubstituted or substituted 1,3-butadienyl;R.sup.5 and R.sup.7 are each hydrogen or C.sub.1 -C.sub.4 -alkyl;R.sup.6 and R.sup.8 are each a radical R.sup.5 ; substituted C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.7 -cycloalkyl; C.sub.1 -C.sub.4 -alkoxycarbonyl; unsubstituted or substituted phenyl or unsubstituted or substituted amino, andX is oxygen or sulfur,processes for their preparation and herbicides which contain them.

    摘要翻译： 氰基喹啉化合物Ia或Ib其中R 1是CH = C（CN）2; CH = N-N = CH-（5-喹啉基）; 甲基磺酰基; CH = NOH; 卤素; 羟; 硝基 氰基; 未取代或取代的C 1 -C 4 - 烷基，C 1 -C 4 - 烷氧基或C 1 -C 4 - 烷硫基，吡咯烷基; 哌啶基; 吗啉基 硫代吗啉基; 未取代或取代的苯基，苯氧基，苯硫基，苯基二硫代基，苯基磺酰基或吡咯基; m为0,1,2或3; R2是氢; 羟; 卤素; C1-C4-烷氧基; -NR3R4; -NR5-CXR6或-N = CR7R8; R3是氢或未取代的或取代的C1-C4-烷基; R4是一个基团R3; C 1 -C 4烷基氨基; 二-C 1 -C 4烷基氨基; 取代的C 1 -C 4 - 烷基; CH = N-（3-氰基-2-喹啉基）; 或者R 3和R 4一起形成可以被杂原子间隔的C4-或C3-亚烷基，或未取代或取代的1,3-丁二烯基; R5和R7各自为氢或C1-C4-烷基; R6和R8各自为基团R5; 取代的C 1 -C 4 - 烷基; C 3 -C 7 - 环烷基; C 1 -C 4烷氧基羰基; 未取代或取代的苯基或未取代或取代的氨基，X为氧或硫，其制备方法和含有它们的除草剂。

    Method of producing 2-alkyl-3-(4,5-dihydroisoxazole-3-yl)-halobenzenes
    10.
    发明授权
    Method of producing 2-alkyl-3-(4,5-dihydroisoxazole-3-yl)-halobenzenes 有权
    2-烷基-3-（4,5-二氢异恶唑-3-基） - 卤代苯的制备方法

    公开(公告)号：US06548677B1

    公开(公告)日：2003-04-15

    申请号：US09856037

    申请日：2001-05-17

    申请人： Michael Rack ,  Norbert Götz ,  Helmut Hagen ,  Wolfgang von Deyn ,  Ernst Baumann ,  Rene Lochtman ,  Joachim Gebhardt

    发明人： Michael Rack ,  Norbert Götz ,  Helmut Hagen ,  Wolfgang von Deyn ,  Ernst Baumann ,  Rene Lochtman ,  Joachim Gebhardt

    IPC分类号： C07D26118

    CPC分类号： C07D261/04

    摘要： A novel process for preparing the compounds of the formula I where: n is 0, 1 or 2; R1, R2 are C1-C6-alkyl; R3, R4, R5 are hydrogen or C1-C6-alkyl, or R4 and R5 together form a bond; R6 is Cl, Br, which comprises a synthesis sequence starting from 1,2-dialkylbenzenes of the formula II with subsequent halogenation to give 3,6-dihalo-1,2-dialkylbenzenes, haloalkylation to give benzyl bromides, oxidation to give benzaldehydes, oximation, reaction with alkenes to give isoxazoles, conversion into thioethers and, if appropriate, oxidation to give sulfenyl or sulfonyl derivatives of the formula I.

    摘要翻译： 一种制备式I化合物的新方法，其中n为0,1或2; R 1，R 2为C 1 -C 6 - 烷基; R 3，R 4，R 5为氢或C 1 -C 6烷基，或者R 4和R 5一起形成 R 6是Cl，Br，其包含从式II的1,2-二烷基苯开始的合成序列，随后卤化以得到3,6-二卤代-1,2-二烷基苯，卤代烷基化得到苄基溴，氧化得到 苯甲醛，肟化，与烯烃的反应得到异恶唑，转化成硫醚，如果合适，氧化得到式I的磺酰基或磺酰基衍生物。