Herbicidally active thiadiazabicyclononanes and nonenes

    公开(公告)号:US5180418A

    公开(公告)日:1993-01-19

    申请号:US732988

    申请日:1991-07-19

    摘要: Cycloalkanecarboxylic acid derivatives of formula I ##STR1## wherein W is ##STR2## and A is CO--R.sub.3 or CN; R.sub.1 is hydrogen or fluorine; R.sub.2 is halogen or cyano; R.sub.3 is chlorine, X--R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, d-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 hydroxyalkylamino, di-C.sub.1 -C.sub.4 hydroxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(R.sub.9)R.sub.10 or the group --N--R.sub.6 (OR.sub.6); each of R.sub.4 and R.sub.14, independently of the other, is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, halo-C.sub.3 -C.sub. 8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyl-C.sub.1 -C.sub.4 alkyl or halo-C.sub.3 -C.sub.7 cycloalkyl, or benzyl which is unsubstituted or substituted at the phenyl ring by up to three identical or different substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkoxy, or is an alkali metal ion, an alkaline earth metal ion or an ammonium ion, the group --[CHR.sub.6 --(CH.sub.2).sub.m ]--COOR.sub.7, or the group [CHR.sub.6 --(CH.sub.2).sub.t --Si(R.sub.8).sub.3 ]; R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.7 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 alkoxy-C.sub.2 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkylthio-C.sub.2 -C.sub.8 alkyl or C.sub.3 -C.sub.7 cycloalkyl; R.sub.8 is C.sub.1 - C.sub.4 alkyl; R.sub.9 is C.sub.1 -C.sub.4 alkyl; R.sub.10 is C.sub.1 -C.sub.4 alkyl or phenyl; or R.sub.9 and R.sub.10, together with the carbon atom to which they are bonded, form a cyclohexane ring; R.sub.11 is C.sub.1 -C.sub.8 alkyl; R.sub.12 is hydrogen or C.sub.1 -C.sub.8 alkyl; R.sub.13 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 alkenyl or C.sub.3 -C.sub.7 alkynyl; X, Y, Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, Z.sub.1 and Z.sub.2 are each independently oxygen or sulfur; n is 0, 1, 2, 3 or 4; m is 0, 1, 2, 3 or 4; q is 1 or 2; and t is 0, 1, 2, 3 or 4, have good pre- and post-emergence selective herbicidal and growth regulating properties.

    Cyclohexanediones and their use as plant growth regulators
    12.
    发明授权
    Cyclohexanediones and their use as plant growth regulators 失效
    环己酮和它们作为植物生长调节剂的用途

    公开(公告)号:US4872902A

    公开(公告)日:1989-10-10

    申请号:US153376

    申请日:1988-02-08

    摘要: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl,R.sub.6 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, andR.sub.7 is hydrogen, 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, and to salts of the compounds of formula I with acids, bases or complex-formers, to processes for the preparation thereof and to novel intermediates. The compounds of formula I have herbicidal and growth-regulating action.

    摘要翻译: 本发明涉及式I的新型环己二酮,其中R是氢或C 1 -C 6 - 烷基,A是R 2,OR 3或NR 3 R 4,R 2是未被取代或是未取代的C 1 -C 6烷基, 被C1-C4-烷氧基取代或被卤素单取代或多取代,或为C3-C6-环烷基,R3为C1-C6-烷基或C3-C6-环烷基,或为苯基或苄基,各为未取代的或 是被R5,R4和R4独立地被R5,R4是氢,C1-C6-烷基,C1-C4-烷氧基或C3-C6-环烷基,R3和R4与氮原子一起, 它们是键合的,吡咯烷,吗啉或哌啶基,B是基团之一,m是0,1,2或3,R 5是卤素,硝基,氰基,C 1 -C 4 - 烷基,C 1 -C 4 - 烷氧基 ,C 1 -C 4 - 烷硫基,C 1 -C 4卤代烷基,C 1 -C 4 - 烷基亚磺酰基或C 1 -C 4 - 烷基磺酰基,R 6是C 1 -C 6烷基或C 3 -C 6环烷基,R 7是氢,C 1 -C 6烷基, C 1 -C 6卤代烷基,C 3 -C 6烯基,C 3 -C 6卤代链烯基或C 3 -C 6炔基,以及式I化合物与酸的盐, 碱或复合物,其制备方法和新型中间体。 式I的化合物具有除草和生长调节作用。

    Method of combating undesirable plant growth and of regulating plant
growth
    13.
    发明授权
    Method of combating undesirable plant growth and of regulating plant growth 失效
    打击不良植物生长和调节植物生长的方法

    公开(公告)号:US4851028A

    公开(公告)日:1989-07-25

    申请号:US92252

    申请日:1987-09-02

    摘要: A method of combating undesirable plant growth and of regulating plant growth, which comprises allowing a herbicidal or plant-regulating amount of a compound of the formula I ##STR1## in which R.sub.1 is SR.sub.2 ; OR.sub.2 ; O--CHR.sub.10 R.sub.2 ; N(R.sub.3) (CHR.sub.10 R.sub.4); N(R.sub.11)(CHR.sub.10 R.sub.4) or NR.sub.3 R.sub.4 ; R.sub.2 is optionally substituted C.sub.1 -C.sub.10 -alkyl C.sub.1 -C.sub.4 -haloalkyl; C.sub.3 -C.sub.8 -alkenyl; (3-methyloxetan-3-yl)methyl; C.sub.3 -C.sub.8 -alkynyl; or an optionally substituted radical from the group comprising phenyl, benzyl, C.sub.3 -C.sub.7 -cycloalkyl, furanyl or furfuryl R.sub.3 and R.sub.4 independently of one another are hydrogen; an optionally substituted phenyl or benzyl radical; C.sub.1 -C.sub.8 -alkyl; or C.sub.3 -C.sub.6 -cycloalkyl; or R.sub.3 and R.sub.4, together with the nitrogen atom, form a saturaated 5- or 6-membered heterocyclic ring which contains up to two heteroatoms from the group comprising N, O and S and can be mono- or disubstituted by C.sub.1 -C.sub.4 -alkyl; R.sub.5 is hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl; nitro; cyano; C.sub.1 -C.sub.4 -haloalkoxy; phenylthio; di-C.sub.1 -C.sub.4 - alkylamino; phenyl; or is optionally substituted phenoxy; and R.sub.6 and R.sub.7 independently of one another are hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; nitro; cyano; or di-C.sub.1 -C.sub.4 -alkylamino, and R.sub.10 and R.sub.11 independently of one another are C.sub.1 -C.sub.4 -alkyl; and salts of compounds of the formula I with acids and bases, to act on the plants or on the environment of the plants, and novel compounds of the formula I' ##STR2## process for their preparation and herbicidal or plant growth-regulating compositions containing these novel compounds.

    摘要翻译: 一种防治不期望的植物生长和调节植物生长的方法,其包括允许除草或植物调节量的其中R 1为SR 2的式I化合物(I); OR2; O-CHR10R2; N(R3)(CHR10R4); N(R11)(CHR10R4)或NR3R4; R2是任选取代的C 1 -C 10 - 烷基C 1 -C 4 - 卤代烷基; C3-C8-烯基; (3-甲基氧杂环丁烷-3-基)甲基; C3-C8-炔基; 或由苯基,苄基,C 3 -C 7 - 环烷基,呋喃基或糠基R3和R4彼此独立地选自任意取代的基团是氢; 任选取代的苯基或苄基; C 1 -C 8 - 烷基; 或C 3 -C 6 - 环烷基; 或R3和R4与氮原子一起形成饱和的5或6元杂环,其含有至多两个来自包含N,O和S的基团的杂原子,并且可被C1-C4烷基单或二取代 ; R5是氢; 卤素; C 1 -C 8 - 烷基; C 1 -C 4 - 烷氧基,C 1 -C 4 - 卤代烷基; 硝基 氰基; C 1 -C 4卤代烷氧基; 苯硫基 二-C 1 -C 4烷基氨基; 苯基; 或任选取代的苯氧基; 且R 6和R 7彼此独立地为氢; 卤素; C 1 -C 8 - 烷基; C 1 -C 4 - 卤代烷基; C1-C4-烷氧基; C 1 -C 4卤代烷氧基; 硝基 氰基; 或二-C 1 -C 4烷基氨基,R 10和R 11彼此独立地为C 1 -C 4 - 烷基; 和式I化合物与酸和碱的盐作用于植物或植物环境,以及式I'(I')的新化合物,其制备和除草或植物生长过程 含有这些新化合物的调节组合物。

    Heterocyclically fused pyridine compounds as herbicides
    14.
    发明授权
    Heterocyclically fused pyridine compounds as herbicides 失效
    杂环稠合吡啶化合物作为除草剂

    公开(公告)号:US4743296A

    公开(公告)日:1988-05-10

    申请号:US936214

    申请日:1986-12-01

    CPC分类号: C07D471/14 A01N43/90

    摘要: This is a continuation in part application derived from our copending application Ser. No. 837,977 (filing date Mar. 10, 1986). 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, R is a C.sub.1 -C.sub.4 nitroalkyl group, a substituted C.sub.1 -C.sub.4 alkylthio group or C.sub.1 -C.sub.4 alkoxy group, an unsubstituted or substituted C.sub.3 -C.sub.4 alkenylthio or C.sub.3 -C.sub.4 alkynylthio group, the hydroxyamino group, a C.sub.1 -C.sub.4 alkoxyamino, C.sub.3 -C.sub.4 alkenyloxyamino or C.sub.3 -C.sub.4 alkynyloxyamino group, a --PO(C.sub.1 -C.sub.4 alkyl).sub.2 or --PO(CH.sub.3)OC.sub.1 -C.sub.4 -alkyl radical or an unsubstituted or substituted hydrazino radical.

    摘要翻译: 这是来自我们的共同未决申请Ser的部分申请的延续。 837,977号(1986年3月10日提交)。 这一延续部分涉及式I的新型吡啶化合物具有良好的选择性除草性能和芽后效应,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,或两个相邻的取代基一起也形成饱和或不饱和的3-或4-元 亚烷基链或烯基链,其中每个链依次可被一至四个C 1 -C 4烷基取代,R是C 1 -C 4硝基烷基,取代的C 1 -C 4烷硫基或C 1 -C 4烷氧基,未取代或取代的C 3 -C 4烷氧基, C 4链烯基硫基或C 3 -C 4炔硫基,羟基氨基,C 1 -C 4烷氧基氨基,C 3 -C 4链烯氧基氨基或C 3 -C 4炔氧基氨基,-PO(C 1 -C 4烷基)2或-PO(CH 3)OC 1 -C 4烷基或未取代或未取代的 取代的肼基。

    1H-Imidazo [1',2':1,2]pyrrolo[3,4-b]pyridines and their use as
herbicidal agents
    15.
    发明授权
    1H-Imidazo [1',2':1,2]pyrrolo[3,4-b]pyridines and their use as herbicidal agents 失效
    1H-咪唑并[1',2':1,2]吡咯并[3,4-b]吡啶及其作为除草剂的用途

    公开(公告)号:US4721522A

    公开(公告)日:1988-01-26

    申请号:US926925

    申请日:1986-11-03

    CPC分类号: C07D471/14 A01N43/90

    摘要: 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, R is the hydroxyamino group, a C.sub.1 -C.sub.4 alkoxyamino, C.sub.3 -C.sub.4 alkenyloxyamino or C.sub.3 -C.sub.4 alkynyloxyamino group, a --PO(C.sub.1 -C.sub.4 alkyl).sub.2 or --PO(CH.sub.3)OC.sub.1 -C.sub.4 alkyl radical or an unsubstituted or substituted hydrazino radical.

    摘要翻译: 以下式Ⅰ的新型吡啶化合物具有良好的选择性除草性能和芽后效应,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,或两个相邻的取代基一起也形成饱和或不饱和的3-或4-元 亚烷基链或烯基链,其中每个链依次可被一至四个C 1 -C 4烷基取代,R是羟基氨基,C 1 -C 4烷氧基氨基,C 3 -C 4链烯氧基氨基或C 3 -C 4炔氧基氨基,-PO(C1- C4烷基)2或-PO(CH3)OC1-C4烷基或未取代或取代的肼基。

    Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant
growth regulating properties
    16.
    发明授权
    Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties 失效
    具有除草和植物生长调节性质的环己烷二羧酸衍生物

    公开(公告)号:US4623382A

    公开(公告)日:1986-11-18

    申请号:US788176

    申请日:1985-10-16

    摘要: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloaklyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -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,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy orR.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring system which may contain an additional oxygen or sulfur atom in the ringor a metal or ammonium salt thereof.

    摘要翻译: 新型环己二酸羧酸衍生物具有除草和植物生长调节性质。 环己烷二羧酸衍生物具有式I(I)其中A为-OR 2或-NR 3 R 4基团,R为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 6烷氧基或C 2 -C 4烷硫基取代, R1是C1-C6烷基,C1-C6卤代烷基,C3-C6-烯基,C3-C6卤代烯基或C3-C6-炔基,R2,R3和R4分别独立地是氢,C1-C6烷基,C1-C6卤代烷基,C2-C10烷氧基烷基,C2- C10烷硫基烷基; 未被取代或被卤素,C 1 -C 4烷氧基或C 1 -C 4烷硫基取代的C 3 -C 6烯基; C 3 -C 6炔基; 苯基或C 1 -C 6烷基,其中所述苯基核未被取代或被卤素取代; C 1 -C 4烷基,C 1 -C 4烷氧基,C 1 -C 4卤代烷基,硝基或氰基; R 3和R 4中的一个是甲氧基或R 3和R 4与它们所连接的氮原子一起形成5-或6-元杂环体系,其可在环中含有另外的氧或硫原子或金属或 其铵盐。

    Herbicidal thiadiazabicyclooctanes
    20.
    发明授权
    Herbicidal thiadiazabicyclooctanes 失效
    除草剂噻二唑二环辛烷

    公开(公告)号:US5416065A

    公开(公告)日:1995-05-16

    申请号:US154243

    申请日:1993-11-18

    IPC分类号: C07D513/04 A01N43/90

    CPC分类号: C07D513/04

    摘要: Thiadiazabicyclooctanes of formula I ##STR1## wherein Z is oxygen or sulfur;R.sub.53 is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.54 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C3-C6alkynyioxy, hydroxy or C.sub.1 -C.sub.6 haloalkoxy; orR.sub.53 and R.sub.54, together with the carbon atom to which they are bonded, form an unsubstituted 3-, 4-, 5- or 6-membered saturated ring;W is a group of formulae W.sub.1 to W.sub.10 ##STR2##

    摘要翻译: 式I的噻二唑二环辛烷其中Z是氧或硫; R53是氢或C1-C6烷基; R 54是C 1 -C 6烷基,C 1 -C 6烷氧基,C 3 -C 6烯氧基,C 3 -C 6炔氧基,羟基或C 1 -C 6卤代烷氧基; 或R 53和R 54与它们所键合的碳原子一起形成未取代的3-,4-,5-或6-元饱和环; (W1)(W2)(W3)(W4)(W5)(W6)(W7 )(W8)(W9)或(W10)