Benzylhydroxylamines and intermediates used to prepare them

    公开(公告)号:US6057269A

    公开(公告)日:2000-05-02

    申请号:US973780

    申请日:1998-01-05

    摘要: Benzylhydroxylamines I ##STR1## (X=--N(R.sup.7)--O--; Y=O, S; R.sup.1 =halogen, CN, NO.sub.2, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3 =H, NH.sub.2, CH.sub.3 ;R.sup.4 =H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl or C.sub.1 -C.sub.6 -alkylsulfonyl;R.sup.5 =H, halogen, C.sub.1 -C.sub.6 -alkyl;R.sup.6 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl;R.sup.7 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.2 -C.sub.8 -alkenyloxycarbonyl, C.sub.2 -C.sub.6 -alkynyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylcarbamoyl, it being possible for the 14 last-mentioned radicals to have attached to them 1-3 substituents:NO.sub.2, CN, halogen, C.sub.3 -C.sub.8 -cycloalkyl, OH, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkylcarbonyloxy, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylideneaminoxy, C.sub.1 -C.sub.6 -alkylcarbamoyl,unsubstituted or substituted phenyl, phenoxy or phenylsulfonyl,a 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1-3 hetero atoms, it being possible for this group to be saturated, unsaturated or aromatic and to have attached to it 1-3 substituents,--CO--Z.sup.1 R.sup.9, --OCO--Z.sup.1 R.sup.9, --N(R.sup.9)R.sup.10 orR.sup.7 =unsubstituted or substituted cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl, phenylcarbamoyl;R.sup.8 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, it being possible for each of the 5 last-mentioned radicals to have attached to it 1-3 substituents:NO.sub.2, CN, halogen, C.sub.3 -C.sub.8 -cycloalkyl, OH, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylideneaminoxy,unsubstituted or substituted phenyl- [sic], phenoxy-[sic] or phenylsulfonyl,a 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1-3 hetero atoms, it being possible for this group to be saturated, unsaturated or aromatic and to have attached to it 1-3 substituents,--CO--Z.sup.2 R.sup.11, --OCO--Z.sup.2 R.sup.11, --N(R.sup.11)R.sup.12 ;Z.sup.1 a chemical bond, oxygen, sulfur or --N(R.sup.10)--;Z.sup.2 =a chemical bond, oxygen, sulfur or --N(R.sup.12)--;R.sup.9, R.sup.11 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, unsubstituted or substituted phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl,orZ.sup.1 and R.sup.9 and/or Z.sup.2 and R.sup.11 together=a 3- to 7-membered heterocycle having 1-3 hetero atoms and bonded via nitrogen, it being possible for this heterocycle to be saturated, unsaturated or aromatic and, if desired, to have attached to it one to three substituents,R.sup.10, R.sup.12 =H, OH, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy)and the salts of I where R.sup.3, R.sup.7 and/or R.sup.8 =hydrogenare used as herbicides and for the desiccation/defoliation of plants.

    Substituted 2-phenylpyridines
    3.
    发明授权
    Substituted 2-phenylpyridines 失效
    取代的2-苯基吡啶

    公开(公告)号:US6100218A

    公开(公告)日:2000-08-08

    申请号:US117655

    申请日:1998-08-04

    摘要: 2-Phenylpyridines I ##STR1## wherein X is a chemical bond, 1,2-ethynediyl or optionally substituted --(CH.sub.2).sub.1-3 --, --O--(CH.sub.2).sub.1-2 --, --s--(CH.sub.2).sub.1-2 --, --CH.sub.2 --O--CH.sub.2 --, --CH.sub.2 --S--CH.sub.2 -- or --CH.dbd.CH--;Y is oxygen or sulfur;Z.sup.1 is oxygen, sulfur or --N(R.sup.7)--;Z.sup.2 is oxygen, sulfur or --N(R.sup.8)--;R.sup.1, R.sup.2, R.sup.7 and R.sup.8 independently of one another are hydrogen, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or heterocyclyl; orR.sup.1 and R.sup.2 or R.sup.7, or R.sup.2 and R.sup.8 together are optionally substituted --(CH.sub.2).sub.2-5 -- or --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --, orR.sup.1 and R.sup.2 together are optionally substituted 1,2-phenylene;R.sup.3 is cyano, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 and R.sup.5 are hydrogen or halogen;R.sup.6 is halogen or haloalkyl;n is zero or one;and their salts are suitable for controlling undesirable vegetation and as desiccants or defoliants.

    摘要翻译: PCT No.PCT / EP97 / 00735 Sec。 371日期:1998年8月4日 102(e)日期1998年8月4日PCT提交1997年2月17日PCT公布。 第WO97 / 30059号公报 日期:1992年8月21日 - 苯基吡啶I其中X为化学键,1,2-亚乙炔基或任选取代的 - (CH 2)1-3 - , - O-(CH 2)1-2 - , - 1-2-,-CH 2 -O-CH 2 - , - CH 2 -S-CH 2 - 或-CH = CH-; Y是氧或硫; Z1是氧,硫或-N(R7) - ; Z2是氧,硫或-N(R8) - ; R 1,R 2,R 7和R 8彼此独立地是氢,任选取代的烷基,烯基,炔基,环烷基,苯基或杂环基; 或者R 1和R 2或R 7,或者R 2和R 8一起是任选取代的 - (CH 2)2-5 - 或 - (CH 2)2 -O-(CH 2)2 - ,或者R 1和R 2一起是任选取代的1,2- 亚苯基; R3是氰基,卤素,烷基,卤代烷基,烷氧基或卤代烷氧基; R4和R5是氢或卤素; R6是卤素或卤代烷基; n为零或一; 并且它们的盐适合于控制不期望的植物和干燥剂或脱叶剂。

    Substituted 2-phenylpyridines useful as herbicides
    4.
    发明授权
    Substituted 2-phenylpyridines useful as herbicides 失效
    用作除草剂的取代的2-苯基吡啶

    公开(公告)号:US5968874A

    公开(公告)日:1999-10-19

    申请号:US983288

    申请日:1998-01-20

    摘要: Substituted 2-phenylpyridines I ##STR1## where n is 0, 1;R.sup.1 is halogen, C.sub.1 -C.sub.6 -haloalkyl;R.sup.2 and R.sup.3 are H, halogen;R.sup.4 is cyano, halogen;X and Y are --O--, --S--;R.sup.5 and R.sup.6 are H, C.sub.1 -C.sub.4 -alkyl or together are a 1,2-ethylene, 1,3-propylene, 1,4-tetramethylene or 1,5-pentamethylene chain;R.sup.7 is C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -haloalkenyl, C.sub.2 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkadienyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.5 -C.sub.6 -cycloalkenyl, 3-oxetanyl, 3-thietanyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl or 5/6-membered heteroaryl having 1 to 3 hetero atoms selected from the group consisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, orR.sup.6 and R.sup.7 together are a 1,2-ethylene or 1,3-propylene chain which can have attached to it one or two C.sub.1 -C.sub.4 -alkyl substituents are used as herbicides and for the desiccation/defoliation of plants.

    摘要翻译: PCT No.PCT / EP96 / 03243 Sec。 371日期1998年1月20日 102(e)1998年1月20日PCT PCT 1996年7月23日PCT公布。 公开号WO97 / 06143 日期1997年2月20日取代的2-苯基吡啶I,其中n为0,1; R1是卤素,C1-C6-卤代烷基; R2和R3是H,卤素; R4是氰基,卤素; X和Y是-O - , - S- R5和R6是H,C1-C4-烷基或一起是1,2-亚乙基,1,3-丙烯,1,4-四亚甲基或1,5-五亚甲基链; R 7是C 1 -C 6卤代烷基,C 3 -C 6卤代链烯基,C 2 -C 6 - 烯氧基-C 1 -C 4 - 烷基,C 2 -C 6 - 烯氧基-C 1 -C 4 - 烷氧基-C 1 -C 4烷基,C 3 -C 6 - 烯基, C 3 -C 6 - 链烯基,C 3 -C 6 - 炔基,C 3 -C 6 - 环烷基,C 5 -C 6 - 环烯基,3-氧杂环丁烷基,3-硫杂环丁基,苯基,苯基-C 1 -C 4烷基或5 至3个选自两个氧原子,两个硫原子和3个氮原子的杂原子,或者R6和R7一起是可以连接至一个或两个的1,2-亚乙基或1,3-亚丙基链 C1-C4烷基取代基用作除草剂和用于植物的干燥/脱叶。

    Substituted 2-phenylpyridines as herbicides
    7.
    发明授权
    Substituted 2-phenylpyridines as herbicides 失效
    取代的2-苯基吡啶作为除草剂

    公开(公告)号:US6010980A

    公开(公告)日:2000-01-04

    申请号:US29994

    申请日:1998-03-13

    CPC分类号: C07D213/61 A01N43/40

    摘要: Substituted 2-phenylpyridines I and their salts ##STR1## where n=0, 1;R.sup.1 =halogen, C.sub.1 -C.sub.4 -haloalkyl;R.sup.2 and R.sup.3 =H, halogen;R.sup.4 =CN, halogen;R.sup.5 =--CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6, --CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sup.8, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7) R.sup.8, --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6 or --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sup.8 ;R.sup.6 =H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.3 -C.sub.4 -alkynyl;R.sup.7 =H, C.sub.1 -C.sub.4 -alkyl, carboxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl;R.sup.8 =H or C.sub.1 -C.sub.4 -alkyl,are used as herbicides and for the desiccation/defoliation of plants.

    摘要翻译: PCT No.PCT / EP96 / 03949 Sec。 371日期1998年3月13日 102(e)1998年3月13日PCT PCT 1996年9月9日PCT公布。 出版物WO97 / 11059 日期1997年3月27日取代的2-苯基吡啶I及其盐,其中n = 0,1; R1 =卤素,C1-C4卤代烷基; R2和R3 = H,卤素; R4 = CN,卤素; R5 = -CO-O-(C1-C4-亚烷基)-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-N(R7)R8,-O-(C1-C4-亚烷基) -CO-O-(C1-C4-亚烷基)-CO-OR6,-O-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-N(R7)R8,-S - (C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-OR6或-S-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基) N(R 7)R 8; R6 = H,C1-C4-烷基,C1-C4-烷氧基-C1-C4-烷基,C2-C4-烯基,C3-C4-炔基; R7 = H,C1-C4-烷基,羧基-C1-C4-烷基,C1-C4-烷氧基羰基-C1-C4-烷基; R8 = H或C1-C4烷基,用作除草剂和用于植物的干燥/脱叶。

    Substituted 2-benz(o)ylpyridines, their preparation and their use as herbicides
    10.
    发明授权
    Substituted 2-benz(o)ylpyridines, their preparation and their use as herbicides 失效
    取代的2-苯并(o)吡啶,其制备及其作为除草剂的用途

    公开(公告)号:US06337305B1

    公开(公告)日:2002-01-08

    申请号:US09381033

    申请日:1999-09-15

    IPC分类号: C07D21330

    CPC分类号: C07D213/61 A01N43/40

    摘要: Substituted 2-benz(o)ylpyridines I and salts thereof where n=0, 1; X=CO, CH2, CH(C1-C4-alkyl), CH—OH, CH—CN, CH-halogen, C(halogen)2, CH—CONH2, CH—CO—O(C1-C4-alkyl), CH—O(C1-C4-alkyl), C(CN)(C1-C4-alkyl); R1=halogen, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl; R2=H, halogen; R3=H, NO2, OH, halogen, C1-C4-alkoxy; R4=H, NO2, OH, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; R5=H, NO2, CN, halogen, C1-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C8-cycloalkyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkinyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C2-C4-alkynyloxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C8-alkyl, cyano-C2-C8-alkenyl, cyano-C3-C8-alkynyl, unsubstituted or substituted OH, SH, SO—H, —SO2—H, COOH or NH—COOH, —SO2Cl, —N(R9,R10), —NH—SO2—(C1-C8-alkyl), —N[—SO2—(C1-C8-alkyl)]2, —N(C1-C8-alkyl)[—SO2—(C1-C8-alkyl)], —SO2—N(R9,R10), —O—CO—NH—R9, unsubstituted or substituted CHO, —O—CHO or —NH—CHO, —NH—CO—NH—R9, —O—CS—NH2, —O—CS—N(C1-C8-alkyl)2, —CO—N(R9,R10), —CS—N(R9,R10), —CO—NH—SO2—(C1-C4-alkyl).

    摘要翻译: 取代的2-苯并(o)吡啶I和其中n = 0,1; X = CO,CH 2,CH(C 1 -C 4 - 烷基),CH-OH,CH-CN,CH-卤素,C(卤素) CH-CONH 2,CH-CO-O(C 1 -C 4 - 烷基),CH-O(C 1 -C 4 - 烷基),C(CN)(C 1 -C 4 - 烷基); R 1 =卤素,C 1 -C 4卤代烷基, 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; R 2 = H,卤素; R 3 = H,NO 2,OH,卤素,C 1 -C 4 - 烷氧基; R 4 = H,NO 2,OH,卤素, C 1 -C 4 - 烷基,C 1 -C 4 - 卤代烷基,C 1 -C 4 - 烷氧基; R 5 = H,NO 2,CN,卤素,C 1 -C 8烷基,C 3 -C 8 - 烯基,C 3 -C 8炔基,C 3 -C 8 - 环烷基,C 1 -C 8 - 卤代烷基,C 2 -C 8 - 卤代烯基,C 2 -C 8 - 卤代炔基,C 1 -C 4 - 烷氧基-C 1 -C 4烷基,C 2 -C 4 - 烯氧基-C 1 -C 4烷基,C 2 -C 4 - C 1 -C 4烷基,C 1 -C 4烷硫基-C 1 -C 4烷基,C 1 -C 4烷基亚磺酰基-C 1 -C 4烷基,C 1 -C 4烷基磺酰基-C 1 -C 4 - 烷基,氰基-C 1 -C 8烷基, 氰基-C 2 -C 8 - 烯基,氰基-C 3 -C 8 - 炔基,未取代或取代的OH,SH,SO-H,-SO 2 -H,COOH或NH-COOH,-SO 2 Cl,-N(R 9,R 10) NH-SO 2 - (C 1 -C 8 - 烷基),-N [-SO 2 - (C 1 -C 8 - 烷基)] 2,-N(C 1 -C 8 - 烷基) -SO 2 -N(R 9,R 10),-O-CO-NH-R 9,未取代的 取代的CHO,-O-CHO或-NH-CHO,-NH-CO-NH-R9,-O-CS-NH2,-O-CS-N(C1-