• 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:
    Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4- trisubstituted benzoyl)-1,3-cyclohexanediones. The intermediate benzoic acids of this invention have the following structural formula: wherein R6 is chlorine, C1-C4 alkoxy, C1-C4 alkylthio or hydroxy; n is the integer 0 or 2; and R7 is C1-C4 alkyl.
    公开号:SU1436870A3
    申请号:SU864027161
    申请日:1986-03-06
    公开日:1988-11-07
    发明作者:Луис Ли Давид
    申请人:Стауффер Кемикал Компани (Фирма)；
    IPC主号:
    专利说明:

    four;
    00
    Od 00
    The invention relates to a process for the preparation of 4- (alkylsulfone) -2-chloro-3-hydroxybenzoic acid of the formula
    BUT C1
    /
    KSO VCOOH
    (I)
    where R is C-Cd-alkyl,
    which can be used in the synthesis of 1,3-dicyclohexanedione derivatives used as herbicides.
    The purpose of the invention is to develop a method for the preparation of new compounds of formula (I), on the basis of which new derivatives of 1,3-dicyclohexanedione would be obtained, having higher
    herbicidal activity than known analogues in structure and purpose of
    Example 1. 2-Chloro-A-ethylsulfonyl-3-hydroxybenzoic acid.
    A solution of 4-ethylsulfoalkyl-2,3-dichlorobenzoic acid, 94 g (0.35 mol) in 500 MP of a 20% sodium hydroxide solution is heated under reflux for 7 hours. After cooling, the aqueous solution is acidified with concentrated hydrochloric acid (300 ml) and two odes extracted with ethyl acetate (400 ml). The ethyl acetate extracts are mixed, dried over magnesium sulphate and concentrated in vacuo to give a crude acid (77 g) - 84%. Recrystallization of the crude acid from ethyl acetate (250 ml) gives pure target acid as white crystals of 44 g, m.p. 188-192 ° C.
    : Others, the compounds are prepared in the same manner as described in Example 1 and are listed in Table. one.
    4- (Alkylsulfonyl) -2-chloro-3-hc, - roxybenzoic acid is used to produce 1,3-dicyclohexanedione derivatives, which are used as herbicides.
    Comparative data on the herbicidal activity of these herbicides are given in Table. 2-4. In tab. Table 2 lists the herbicides that have been tested and Table. 3 and 4 - the results of testing of herbicides before (Table 3) and after (Table 4) on the appearance of seedlings. These data in the table. 3 and 4 for the compounds of table. 2 demonstrate
    for most compounds, herbicidal activity at a dose of 0.56 kg / ha.
    As prior art, well-known compounds are contrasted, which are similar in structure to the compounds of table. 2 and have the following structural formulas:
    compound 1
    compound 2
    compound 3
    OSI:
    compound 4

    Compounds 1-4 were tested to determine herbicidal activity in accordance with test methods for the compounds of Table. 2 with a spread rate of 4.48 kg / ha.
    In tab. 3 and 4 mark - means that this species, for some reason, did not germinate. Letters denote herbs: a fluffy bonfire Bromus tectorum (DB). multi-flowered loliura multi-florum (ARC), sorghum bicolor bicolor sorghum (SHC), sesbani hemp Sesbania exaltata (SESB), nightshade Solanum sp. (SP), Cocktail Xattiium sp. (CB).
    As can be seen from the table. 3 and 4 herbicides, prepared on the basis of new compounds of formula (I), are more active than the known ones.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining 4- (alkylsulfonyl) -2-chloro-3-hydroxybenzoic acid -. lots of general formula
    BUT Cl KSO -Q-COgH
    where R is C, -C-alkyl, characterized in that 4- (alkylsulfonyl) -2,3-dichlorobenzoic acid of the general formula
    C1 C1
    t a b i: c
    4-Alkylsulfonyl-2-chloro-3-hydroxybenzoic acid
    BUT C1 RS02 fjVCOOH
    Continuation of table 2
    1436870.-8
    Continuation of table 3
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    同族专利:
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3729508A|1969-11-20|1973-04-24|Merck & Co Inc|Sulfonylbenzoic acids|
    US3663615A|1970-03-02|1972-05-16|Merck & Co Inc|Nuclear sulfamoyl n-organosulfonyl benzamides|
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    US4350705A|1979-03-31|1982-09-21|Eisai Co., Ltd.|Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives|
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    US4806146A|1984-12-20|1989-02-21|Stauffer Chemical Company|Certain 2--1,3-cyclohexanediones|
    US4780127A|1982-03-25|1988-10-25|Stauffer Chemical Company|Certain 2--1,3-cyclohexanediones and their use as herbicides|
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    JPS58198464A|1982-05-14|1983-11-18|Seitetsu Kagaku Co Ltd|Preparation of 4-methylthio-2-alkoxybenzoic acid|
    EP0137963B1|1983-09-16|1988-09-28|Stauffer Chemical Company|Certain 2--1,3-cyclohexanediones|
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    US4695673A|1985-11-20|1987-09-22|Stauffer Chemical Company|Process for the production of acylated 1,3-dicarbonyl compounds|JP2734579B2|1988-09-19|1998-03-30|日産化学工業株式会社|Method for producing substituted benzoic acid|
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    US5073642A|1988-11-18|1991-12-17|Ici Americas Inc.|Trisubstituted benzoic acid intermediates|
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    DE69933222T2|1998-07-14|2007-01-04|Nippon Soda Co. Ltd.|Benzoic acid derivatives and process for their preparation|
    JP4592129B2|1998-07-14|2010-12-01|日本曹達株式会社|Novel benzoic acid derivatives and process for producing the same|
    AR056889A1|2005-12-15|2007-10-31|Ishihara Sangyo Kaisha|BENZOILPIRAZOL AND HERBICIDE COMPOUNDS CONTAINING THEM|
    CN101691347A|2009-09-28|2010-04-07|唐保清|Preparation process of 4-benzoyl chloride|
    DE102017010478A1|2016-12-02|2018-06-07|Merck Patent Gmbh|Thioether compounds|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US06/709,006|US4898973A|1985-03-07|1985-03-07|Trisubstituted benzoic acid intermediates|
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