• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Die neuen Derivate von im Phenylring substituierten 1-Phenyl-imidazol-5-carbonsäuren werden durch die allgemeine Formel (I) beschrieben, worin die Symbole folgende Bedeutung haben: R1, R2 unabhängig voneinander (C1-C4)Alkyl; R3 (C1-C4)Alkyl, (C,-C4)Alkoxy oder Halogen, wobei bei n > 1 die Substituenten auch unterschiedlich sein können; n 0, 1, 2 oder 3; und X eine Cyano-, Ester-, Thiolester-, Amid-, Thioester-, Amidoxim-, Alkoxymethyl-, Hydroxymethyl-, Aldehyd-, Keto-, Oxim-, Acetal-, Ketal-, Thioacetal- oder Thioketalgruppe oder ein heterocyclischer Substituent (z.B. Tetrazolyl). Die neuen Verbindungen weisen eine das Pflanzenwachstum regulierende Wirkung auf. In einem Verfahren zur Herstellung dieser Verbindungen wird von der freien Carbonsäure (X= -COOH), ihrem Amid (X= -CONH2), ihren Niederalkylestern [X= -CO-O-(C1-C4)Aklyl] oder aktivierten Derivaten wie Säurehalogeniden ausgegangen und diese dann derivatisiert. Zu den Verbindungen zählen auch die Salze und Quaternisierungsprodukte des basischen Imidazolrings.
    公开号:SU1452456A3
    申请号:SU853990698
    申请日:1985-12-06
    公开日:1989-01-15
    发明作者:Шмирер Роланд；Мильденбергер Хильмар；Хандте Райнхард；Бюрстелль Хельмут
    申请人:Хехст Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to chemicals that regulate plant growth, and may find application in crop production, in particular for growing crops.
    The purpose of the invention is to increase the retardant activity of biologically active substances.
    According to the invention, compounds of the formula (O $ —NX Mui, where X is a group C00N = C (CH 3 ) g , COON = C CONH-OH, formyl or a group of the formula
    OOS-S (O) —N
    Oh or
    0-n
    C2H5 at a dose of 0.0751.25 kg / ha.
    The proposed compounds, which can be used in a mixture with other active components, can be in the form of wettable powder emulsion concentrates, solutions, they can be used for spraying, in the form of dusty preparations, mordants,
    dispersions, granular products or microgranular preparations.
    Example 1, 1- (2,6-Diethylphenyl) -5- / 3-methyl-1,2,4-oxydiazol-5! Yl / imidazole.
    K 5.1 parts by weight (0.047 mol) of acetamidoxime hydrochloride in 50 vol.h. pyridine at 0-10 ° C. was added in portions 10.0 parts by weight (0.033 mol) of 1- (2,6-diethylphenyl hydrochloride, imvda: zol-5-carbonyl chloride). The reaction mixture was stirred for 2 hours at room temperature, then it was poured into water, after which the product was separated by filtration 15. As a result, 6.6 parts by weight (50% of theory) of 1- (2,6-diethylphenyl) -5- (3-methyl-1,2,4- oksdiazol-5-yl) -imidazole s t;. mp 14953 C. in.
    PRI me R 2. 1- / 2,6-Diethylphenyl-5-formylimidazole.
    To 500 ob.ch. absolute methylene chloride and 32.5 parts by weight (0.25 mol) of oxalyl chloride was added dropwise at a temperature of 78 ° C. 25.4 parts by weight (0.33 mol) of oxide in 50 lenchloride. for 1/2 h and then a solution of 39.0 g (0.17 mol) of 1- (2,5-di-ethylphenyl) -5-hydroxymethylimidazole in 50 vol.h, absolute methylene chloride was added to it. Mixture; incubated 2 hours at -70 e C after which was added dropwise thereto 85 parts by weight (0.85 mol) triethipamine. After warming to room temperature, the organic phase was washed twice with water, dried over sodium sulfate and evaporated. As a result, 38.5 parts by weight were obtained. (98% of theory.) - 1- (2,6-diethylphenyl) -5-formylimidazole in the form of an oily substance colored in light yellow; Identification was performed using n-NMR spectroscopy.
    Examples for other compounds are presented in table 1.
    absolute dimethyl sulfob.ch. absolute marks, the mixture was kept at a temperature of 78 ° C,
    After untreated control plants reached a height of approximately 55 cm, growth was measured for all plants and growth inhibition was calculated as a percentage of the growth of control plants. In addition, the phytotoxic effect of the compound was determined. Growth inhibition was determined as a percentage, with 100% indicating the cessation of growth, and 0% denoting growth corresponding to the untreated control plant. It turned out that the proposed compounds have a very good ability to regulate plant growth (table 2,3).
    Phytotoxic side effect was not observed, compound A for comparison / _ / С 2 Н 5 О / у - N — yC00Na С 2 Н 5 Sr
    When using the proposed compounds, the growth-regulating effect can be achieved with lower doeah "
    权利要求:
    Claims (2)
    [1]
    Claim
    A method of regulating the growth of crops, including treating plants with a biologically active substance, characterized in that, in order to increase the retardant activity, a compound of the general formula 40 is used as a biologically active substance
    -N— X about U jl ’
    N where X-COON = C (CH % ) Q , COON - (^,
    CONHOH, formyl or group of the formula
    Biological tests.
    When conducting experiments in the greenhouse, young grain crops (wheat, barley, rye) at the stage of three leaves, were sprayed during h attacks and were sprayed with β-droplets of the proposed compounds at various concentrations of biological active substances.
    OR .
    . 1452456
    Table!
    Imidazole derivatives of the formula
    ExampleIN" X Tpa "° C 3 COOH C (CH b ) g C00N- θ Oily substance 4 Resinous substance
    CONH-OH rcooccq
    A resinous substance obtained by saponification of complex 120-8. The result of the action of the hydrochloric acid chloride of anhydride with the salt of XCOONa______ ether in the reimmosoot5
    Continuation of Table 2
    Connection example No. Concentration, kg / ha --------------- -------]Inhibition of growth,% in the case of wheat barley - nya rye 1.25 14 19 24 2,5 27 8 10 1.25 23 0 0 ------- ---— - - Prim e ch n and e, <4mtotoxic act: re- rebirth lack of they steal in all cases / ζ + 2-chloroethyl- triethylammonium chloride T a b l c a 3 Influence proposed compounds on height plants
    T a b l c a
    [2]
    2 The effect of the proposed compounds on grain growth
    Connection example> Concentration, kg / ha Inhibition of growth,% in the case of 40 wheat barley rye 1 2,5 24 39 28 45 1.25 fifteen 19 ' 21 2 2.5, 24 37 27 ά 1.25 fifteen 1 $ 19 3 2,5 25 38 271.25 16 19 21 fifty 4 2,5 25 37 271.25 16 . 18 20 5 2.5. 24 34 271.25 20 21 21 6 2,5 24 38 31 55
    Connection example " Dose kg / ha Inhibition of growth, X, in the case of wheat barley rye J ———— J —————— L ———— 0.62 14 o 16 fifteen 1 0.15 9 9 8 0,075 5 7 5fifteen 16 14 2 AND 7 9 84 4 2 0.62 thirteen 17 14 3 0.15 9 thirteen eleven 0,075 7 6 614 fifteen 16 4 P 9 9 96 4 7 0.62 16 17 16 5 0,075 9 10 95. 6 4 0.62 fifteen 16 fifteen 6 0.15 eleven 12 9 0,075 7 8 3 1.25 14 17 18 A 0.6 ^ 7 10 9 0.15 2 2 0 0,075 0 0 0
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    同族专利:
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    PH21354A|1987-10-15|
    EP0185961A2|1986-07-02|
    ZA859364B|1986-08-27|
    BR8506130A|1986-08-26|
    AU5088485A|1986-06-12|
    JPS61151175A|1986-07-09|
    DK566885A|1986-06-09|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE3217094C2|1982-05-07|1989-12-14|Hoechst Ag, 6230 Frankfurt, De|DE3515094C2|1985-04-26|1988-05-05|Hoechst Ag, 6230 Frankfurt, De|
    DE3608143A1|1986-03-12|1987-09-17|Hoechst Ag|1-PHENYLIMIDAZOLE CARBONIC ACID AMIDES, THEIR PRODUCTION AND THEIR USE AS GROWTH REGULATORS|
    DE3627155A1|1986-08-11|1988-02-18|Schering Ag|IMIDAZOLE DERIVATIVES|
    DE3629064A1|1986-08-27|1988-03-03|Hoechst Ag|2,3,6-SUBSTITUTED PHENYLIMIDAZOLE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS GROWTH REGULATORS|
    EP0319057B1|1987-11-06|1994-03-02|Shell Internationale Researchmaatschappij B.V.|Imidazole derivatives|
    DE3742716A1|1987-12-14|1989-06-22|Schering Ag|IMIDAZOLE DERIVATIVES II|
    DE3808896A1|1988-03-17|1989-09-28|Hoechst Ag|PLANT PROTECTION AGENTS BASED ON PYRAZOL CARBON SEA DERIVATIVES|
    DE4017338A1|1990-05-30|1991-12-05|Bayer Ag|SULFONYLATED CARBONIC ACID AMIDES|
    FR2671348B1|1991-01-09|1993-03-26|Roussel Uclaf|NOVEL PHENYLIMIDAZOLIDINES, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.|
    JP2011502133A|2007-11-02|2011-01-20|メシルジーンインコーポレイテッド|Inhibitors of histone deacetylase|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19843444918|DE3444918A1|1984-12-08|1984-12-08|1-PHENYL-IMIDAZOLE-5-CARBONIC ACID DERIVATIVES, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS GROWTH REGULATORS|
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