PROCESS FOR THE PREPARATION OF (THIO-)CARBONIC/CARBAMIC ACID 2-PYRROLIDONYL-3-ESTERS, THIO ESTERS AND AMIDES
    1.
    发明申请
    PROCESS FOR THE PREPARATION OF (THIO-)CARBONIC/CARBAMIC ACID 2-PYRROLIDONYL-3-ESTERS, THIO ESTERS AND AMIDES 审中-公开
    制备(硫代)碳酸/碳酸2-吡咯烷酮-3-酯,硫酸铵和氨基酸的方法

    公开(公告)号:WO1996037466A1

    公开(公告)日:1996-11-28

    申请号:PCT/GB1996001150

    申请日:1996-05-13

    Inventor: ZENECA LIMITED

    CPC classification number: C07D207/273

    Abstract: A process for the preparation of a compound of general formula (II) wherein R is hydrogen or C1-C10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms, either of which may optionally be substituted with halogen (i.e. chlorine, bromine, fluorine or iodine), hydroxy, SO2NR R (where R and R are independently H or C1-C6 alkyl), SiR 3 (where each R is independently C1-C4 alkyl or phenyl), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, carboxy, carboxyamide, in which the groups attached to the N atom may be hydrogen or optionally substituted lower hydrocarbyl; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such as phenyl; each R , R , R and R is independently hydrogen or C1-C4 alkyl; A is an aromatic or heteroaromatic ring system optionally substituted with one or more substituents selected from: halogen or C1-C10 hydrocarbyl, -O(C1-C10 hydrocarbyl), -S(C1-C10 hydrocarbyl), -SO(C1-C10 hydrocarbyl) or -SO2(C1-C10 hydrocarbyl), cyano, nitro, SCN, SiR 3 (where each R is independently C1-C4 alkyl or phenyl), COR , CR NOR , NHOH, ONR R , SF5, COOR , SO2NR R , OR or NR R ; and in which any ring nitrogen atom may be quaternised or oxidised; alternatively, any two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring in which any carbon or quaternised nitrogen atom may be substituted with any of the groups mentioned above for A or in which a ring carbon atom may be oxidised; R and R are each independently hydrogen or C1-C10 hydrocarbyl; R is hydrogen, C1-C10 hydrocarbyl, SO2(C1-C10 hydrocarbyl), CHO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR R ; R and R are each independently hydrogen, C1-C10 hydrocarbyl, O(C1-C10 hydrocarbyl), SO2(C1-C10 hydrocarbyl), CHO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR R ; any of the hydrocarbyl groups within the group A may optionally be substituted with halogen (i.e. chlorine, bromine, fluorine or iodine), hydroxy, SO2NR R (where R and R are independently H or C1-C6 alkyl), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, carboxy, carboxyamide, in which the groups attached to the N atom may be hydrogen or lower hydrocarbyl optionally substituted with halogen; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such as phenyl; R is hydrogen, halogen OH3 or OCONHR , wherein R is as defined above; the process comprising cyclising a compound of general formula (III), wherein A, R , R , R , R and R are as defined in general formula (II) and R is a leaving group such as a halogen atom; under basic conditions.

    Abstract translation: 制备通式(II)的化合物的方法,其中R 1是氢或具有3至8个环原子的C 1 -C 10烃基或杂环基,其任一个可以任选地被卤素(即氯,溴, 氟或碘),羟基,SO 2 NR a R b(其中R a和R b独立地为H或C 1 -C 6烷基),SiR c 3(其中每个R c独立地为 C 1 -C 6烷基或苯基),氰基,硝基,氨基,一烷基氨基和二烷基氨基,其中烷基具有1至6个或更多个碳原子,酰基氨基,C 1 -C 6烷氧基,C 1 -C 6卤代烷氧基,C 1 -C 6烷硫基, C 1 -C 6烷基亚磺酰基,C 1 -C 6烷基磺酰基,羧基,羧酰胺,其中与N原子连接的基团可以是氢或任选取代的低级烃基; 烷氧基羰基,其中烷氧基可以具有1至6个或更多个碳原子,或芳基如苯基; 每个R 2,R 3,R 4和R 5独立地是氢或C 1 -C 4烷基; A是任选被一个或多个选自以下的取代基取代的芳族或杂芳族环系:卤素或C 1 -C 10烃基,-O(C 1 -C 10烃基),-S(C 1 -C 10烃基), - (C 1 -C 10烃基) )或-SO 2(C 1 -C 10烃基),氰基,硝基,SCN,SiR c 3(其中每个R c独立地为C 1 -C 4烷基或苯基),COR 7, 8,NHOH,ONR 7 R 8,SF 5,COOR 7,SO 2 NR 7 R 8,OR 9或NR 10 R 11; 并且其中任何环氮原子可被季铵化或氧化; 基团A的任何两个取代基可以组合形成稠合的5-或6-元饱和或部分饱和的碳环或杂环,其中任何碳或季铵化的氮原子可以被上述任何A或 其中环碳原子可被氧化; R 7和R 8各自独立地为氢或C 1 -C 10烃基; R 9是氢,C 1 -C 10烃基,SO 2(C 1 -C 10烃基),CHO,CO(C 1 -C 10烃基),COO(C 1 -C 10烃基)或CONR 7 R 8; R 10和R 11各自独立地为氢,C 1 -C 10烃基,O(C 1 -C 10烃基),SO 2(C 1 -C 10烃基),CHO,CO(C 1 -C 10烃基),COO 烃基)或CONR 7 R 8; 基团A中的任何烃基可以任选地被卤素(即氯,溴,氟或碘),羟基,SO 2 NR a R b(其中R a和R b独立地是H 或C 1 -C 6烷基),氰基,硝基,氨基,一烷基氨基和二烷基氨基,其中烷基具有1至6个或更多个碳原子,酰基氨基,C 1 -C 6烷氧基,C 1 -C 6卤代烷氧基,C 1 -C 6烷硫基,C 1 -C 6烷基亚磺酰基,C 1 -C 6烷基磺酰基,羧基,羧酰胺,其中与N原子连接的基团可以是氢或任选被卤素取代的低级烃基; 烷氧基羰基,其中烷氧基可以具有1至6个或更多个碳原子,或芳基如苯基; R 21是氢,卤素OH 3或OCONHR 1,其中R 1如上定义; 该方法包括使通式(III)的化合物环化,其中A,R 2,R 3,R 4,R 5和R 21如通式(II)中所定义,和 R 25为离去基团,例如卤素原子; 在基本条件下

    INDOLIZINES AS HERBICIDES
    2.
    发明申请
    INDOLIZINES AS HERBICIDES 审中-公开
    不溶于除草剂

    公开(公告)号:WO1994005662A1

    公开(公告)日:1994-03-17

    申请号:PCT/EP1993002132

    申请日:1993-08-12

    Inventor: ZENECA LIMITED

    CPC classification number: C07D471/04 A01N43/90 C07D471/14

    Abstract: A herbicidal composition comprising a compound of formula (I) or a tautomer or a quaternised derivative thereof where Y is a group of formula -CR1=CR2-CO- and R1, R2, R3, R4 and R5 are independently selected from hydrogen; optionally substituted alkyl; optionally alkenyl; optionally substituted alkynyl; optionally substituted aryl; optionally substituted aromatic heterocyclic; halo; nitro; cyano; a group OR6 where R6 is hydrogen or a salt thereof, carboxy or an ester thereof, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted aryl; carboxy or a salt, ester or amide derivative thereof; S(O)nR7 where n is 0, 1 or 2 and R7 is optionally alkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted aryl; NR8R9 where R8 and R9 are independently selected from hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted aryl and R9 may additionally be acyl, or R8 and R9 together with the nitrogen atom to which they are attached form a heterocyclic ring; or R1 and R2 and/or any adjacent two of R3, R4 and R5 together with the carbon atoms to which they are attached form an optionally substituted fused saturated or unsaturated carbocyclic or heterocyclic ring; in combination with a carrier or diluent.

    Abstract translation: 一种除草组合物,其包含式(I)化合物或其互变异构体或其季铵化衍生物,其中Y为式-CR1 = CR2-CO-基团,R1,R2,R3,R4和R5独立地选自氢; 任选取代的烷基; 烯基; 任选取代的炔基; 任选取代的芳基; 任选取代的芳族杂环; 光环; 硝基; 氰基; 任选取代的烷基,任选取代的烯基,任选取代的炔基或任选取代的芳基;其中R 6为氢或其盐,羧基或其酯,任选取代的烷基,任选取代的烯基, 羧基或其盐,酯或酰胺衍生物; S(O)n R 7,其中n为0,1或2,R 7为任选烷基,任选取代的烯基,任选取代的炔基或任选取代的芳基; NR 8 R 9,其中R 8和R 9独立地选自氢,任选取代的烷基,任选取代的烯基,任选取代的炔基或任选取代的芳基,R 9可以另外是酰基,或者R 8和R 9与它们所连接的氮原子一起形成杂环 环; 或R 1和R 2和/或R 3,R 4和R 5中的任何相邻的两个与它们所连接的碳原子一起形成任选取代的稠合饱和或不饱和碳环或杂环; 与载体或稀释剂组合。

    HERBICIDAL INDOLINES
    4.
    发明申请
    HERBICIDAL INDOLINES 审中-公开
    除草剂

    公开(公告)号:WO1997045408A1

    公开(公告)日:1997-12-04

    申请号:PCT/GB1997001386

    申请日:1997-05-21

    Inventor: ZENECA LIMITED

    Abstract: Compounds of formula (I) are useful as herbicides: wherein R and R independently represent hydrogen or C1-4 alkyl; R is hydrogen or a C1-10 aliphatic radical optionally substituted with one or more halogen atoms; W1 and W2 independently represent O or S; Y is O or NR4, wherein R is hydrogen, C1-4 alkoxy or a C1-6 aliphatic radical optionally substituted with one or more halogen atoms or C1-4 alkoxy groups; Z is NR or CR R ; or, when Y is NR and Z is NR , R and R together may represent -CH2CH2-, -CH=CH-, -C(O)C(O)- or -CH2C(O)-; or, when Y is NR4 and Z is CR R , R and one of R and R may represent -CH2- or -CH2CH2-; or, when Z is CR R , R may be a C1-6 alkoxycarbonyl group; X is C1-10 alkyl, halo-C1-10 alkyl, C1-10 alkoxy, halo-C1-10 alkoxy, cyano, -SF5, SO2CF3, -SCF3, nitro or halo; and n is 0, 1, 2, 3 or 4.

    Abstract translation: 式(I)化合物可用作除草剂:其中R 1和R 2独立地表示氢或C 1-4烷基; R 3是氢或任选被一个或多个卤素原子取代的C 1-10脂族基; W1和W2独立地表示O或S; Y是O或NR4,其中R 4是氢,C 1-4烷氧基或任选被一个或多个卤素原子或C 1-4烷氧基取代的C 1-6脂族基; Z是NR 5或CR 6 R 7; 或者当Y为NR 4且Z为NR 5时,R 4和R 5一起可以表示-CH 2 CH 2 - , - CH = CH - , - C(O)C(O) - 或 -CH 2 C(O) - ; 或者当Y为NR 4且Z为CR 6 R 7时,R 4和R 6和R 7中的一个可以表示-CH 2 - 或-CH 2 CH 2 - ; 或者当Z是CR 6 R 7时,R 3可以是C 1-6烷氧基羰基; X为C 1-10烷基,卤代C 1-10烷基,C 1-10烷氧基,卤代C 1-10烷氧基,氰基,-SF 5,SO 2 CF 3,-SCF 3,硝基或卤素; n为0,1,2,3或4。

    SUBSTITUTED PYRROLIDINONE, THIAZOLIDINONE OR OXAZOLIDINONE AS HERBICIDES
    5.
    发明申请
    SUBSTITUTED PYRROLIDINONE, THIAZOLIDINONE OR OXAZOLIDINONE AS HERBICIDES 审中-公开
    取代的吡咯烷酮,噻唑烷酮或氧杂环己胺作为除草剂

    公开(公告)号:WO1997020838A1

    公开(公告)日:1997-06-12

    申请号:PCT/GB1996002946

    申请日:1996-11-28

    Inventor: ZENECA LIMITED

    Abstract: Compounds of formula (I) wherein: n is 0 or an integer from 1 to 5; X is halogen, nitro or cyano, or C1-10 hydrocarbyl or C1-10 hydrocarbyloxy, either of which may be substituted with one or more halogen atoms; Y is CH2, O or S; and R and R independently represent hydrogen, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl or halogen. Processes for the preparation of compounds of formula (I), herbicidal compositions and methods utilizing them are also disclosed.

    Abstract translation: 式(I)的化合物,其中:n为0或1至5的整数; X是卤素,硝基或氰基,或C 1-10烃基或C 1-10烃氧基,其中任一个可被一个或多个卤素原子取代; Y是CH 2,O或S; R 1和R 2独立地表示氢,C 1-6烷基,C 1-6卤代烷基,C 2-6烯基,C 2-6炔基或卤素。 还公开了制备式(I)化合物,除草组合物和利用它们的方法的方法。

    SUBSTITUTED PYRROLIDONE, THIAZOLIDONES OR OXAZOLIDONES AS HERBICIDES
    6.
    发明申请
    SUBSTITUTED PYRROLIDONE, THIAZOLIDONES OR OXAZOLIDONES AS HERBICIDES 审中-公开
    取代的吡咯烷酮,噻唑烷酮或氧杂环己酮作为除草剂

    公开(公告)号:WO1995033719A1

    公开(公告)日:1995-12-14

    申请号:PCT/GB1995001224

    申请日:1995-05-26

    Inventor: ZENECA LIMITED

    Abstract: Compounds of general formula (I), wherein X is O, S or CR R ; each R and R is, independently, hydrogen or C1-C4 alkyl; Z is O, S or NR ; n is 0 or 1; Y is O, S, NR or CR R ; R is H, OH, CHO, NR R or C1-C10 hydrocarbyl, 0-(C1-C10 hydrocarbyl), either of which may be substituted with one orm ore substituents chosen from OR , COR , COOR , OCOR , CN, halogen, S(O)pR , NR R , NO2, NR COR , NR CONR R , CONR R or heterocyclyl; R , R and R are each, independently, hydrogen, C1-C6 hydrocarbyl or C1-C6 halohydrocarbyl; p is 0, 1 or 2; alternatively: when Y is NR or CR R , and: a) Z is NR ; or b) n is 0; the substituents of Y and Z or Y and R may together form a bridge represented by the formula -Q -Q - or -Q -Q -Q -, where Q , Q and Q each independently represent CR R , =CR , CO, NR , =N, O or S; each or R and R independently represents hydrogen, C1-C4 alkyl, OH or halogen; R represents hydrogen or C1-C4 alkyl; W is O or S; R is hydrogen or C1-C10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms; R and R are each independently hydrogen or C1-C4 alkyl; A is an aromatic or heteroaromatic ring system optionally substituted alternatively, two or more substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring in which any carbon or quaternised nitrogen atom may be substituted with any of the groups mentioned above for A or in which a ring carbon atom may be part of a carbonyl group or a nitrogen atom may be oxidised.

    Abstract translation: 通式(I)的化合物,其中X是O,S或CR 4 R 5; 每个R 4和R 5独立地是氢或C 1 -C 4烷基; Z是O,S或NR 4; n为0或1; Y是O,S,NR 6或CR 4 R 5; R 6是H,OH,CHO,NR 16 R 17或C 1 -C 10烃基,O-(C 1 -C 10烃基),其中任一个可以被一个选自OR 16的取代基取代 ,COR 16,OCOR 16,CN,卤素,S(O)p R 16,NR 16 R 17,NO 2,NR 16 COR 17, NR 16 CONR 17 R 18,CONR 16 R 17或杂环基; R 16,R 17和R 18各自独立地为氢,C 1 -C 6烃基或C 1 -C 6卤代烃基; p为0,1或2; 或者:当Y是NR 6或CR 4 R 5时,和:a)Z是NR 4; 或b)n为0; Y和Z或Y和R 1的取代基可以一起形成由式-Q 1 -Q 2 - 或-Q 1 -Q 2 -Q 3 - 其中Q 1,Q 2和Q 3各自独立地表示CR 12 R 13,= CR 12,CO,NR 14,= N,O或S; 每个或R 12和R 13独立地表示氢,C 1 -C 4烷基,OH或卤素; R 14表示氢或C 1 -C 4烷基; W为O或S; R 1是氢或C 1 -C 10烃基或具有3至8个环原子的杂环基; R 2和R 3各自独立地为氢或C 1 -C 4烷基; A是任选地任选取代的芳族或杂芳族环系统,组A中的两个或多个取代基可以结合形成稠合的5或6元饱和或部分饱和的碳环或杂环,其中任何碳或季铵化氮原子可以是 被上述任何A取代或环碳原子可以是羰基或氮原子的一部分被氧化。

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