• 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:
    There is disclosed the 2-(2-aminoethoxy) ethanol salt of dicamba. This compound has herbicidal utility, and the advantages of a lower volatility and excellent solubility in water and organic solvents.
    公开号:SU1380618A3
    申请号:SU853979502
    申请日:1985-11-25
    公开日:1988-03-07
    发明作者:С.Джоунс Рита；Т.Чирчирилло Майкл；Л.Бернс Джонни
    申请人:Велсикол Кемикал Корпорейшн (Фирма)；
    IPC主号:
    专利说明:

    with
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    about
    O5 00

    sn
    one
    The invention relates to organic synthesis, specifically a new salt of 2- (2-aminoethoxy) ethanol salt of 3,6-dichloro-2-methoxybenzoic acid (Dicamba), which has a herbicidal effect.
    The aim of the invention is to develop, on the basis of a known method, a method for producing a new compound having improved herbicidal properties.
    It was found that the salt of 2- (2- -hydroxyethoxy) ethylamine and D1CAMBA
    13
    (3,6-dichloro-2-methoxybenzoic acid, with a volatility of 2- (2-aminoethoxy) etati) reduces volatility and improves other not very successful properties of DICAMBA without affecting the beneficial herbicidal properties of this compound.
    The invention illustrates jn with the following examples.
    Example 1. D1CAMBA (22.1 g; 0.10 mol) and water (100 ml) are placed in a beaker. To mix
    compared with the volatility of the commercial dimethyl-amine salt DJCAMBA, experiments were carried out with these compounds. Example 6. The dimethyl amine salt 14, .- B1CAMBA (DMA) and 2- (2-aminoethoxy) ethanol salt 14C -DJCAMBA is obtained . Compounds are applied to glass Petri bags in a concentration of
    thirty
    35
    mixtures are added 2- (2-hydroxyethoxy) 25 about 1134 g / ha and soak. Ethylamine (10.5 g; 0.10 mol) and stirring are continued until the solid compounds dissolve. The cloudy solution is washed twice with methylene chloride, filtered, evaporated on a rotary evaporator, and stripped under vacuum to obtain the desired product — 2-salt-2-hydroxy-ethoxy-ethylamine and (32.3 g). The product has a mp. 76-78 s. Below are the results of elemental analysis:
    Calculated,%: C 44.19; H 5.25; N 4.29; C1 21, 74; 0
    Found,%: C 43.87; H 5.28; N 4.30, C1 21, 09; 0.74.
    In actual use, the salt is used in the form of a solution containing 1814.4 g of the salt of 2- (2-hydroxyethoxy) ethylamine DtCAMBA per 4 liters of water. This solution is easily prepared according to the procedure described in the example below by mixing D1CAMBA, amine and water. The desired salt concentration is obtained by adding a sufficient amount of water to the solution. For that
    45
    at a relative humidity of 70-90%. Samples are taken through O, 2, 5, 15 and 30 days to determine the amount of radiocarbon left in the petri dishes, and the following results are obtained (Table 5).
    At 50 ° C, the chemical stability of the DtCAMBA salt of the invention is determined and the following results are obtained:
    Time days
    ABOUT
    7
    14
    28
    56
    84
    Dicamba is currently used commercially in the form of dimethyl ammonium salt (DMA). As can be seen from the description of this application, the proposed salt is used as a herbicide, and in lower doses than the known salt. For example, the dose of use of compounds
    DJCAMBA,% 39.6 40.1 39.9 39.5 39.4 39.5
    show herbicidal efficacy according to the invention is 141 75 g / ha
    A new compound of the present invention was carried out in a series of tests and compared with the results of using the known UICAMBA dimethylammonium salt (DMA).
    In each case, the tested compounds were deposited 1 by spraying onto the plants using the standard procedure of the method55
    which causes an 85% suppression of the Pensilvian recipe in corn, while the known salt provides only 40% suppression at the same dose. In addition, the proposed salt is more stable at a dose of 145.75 g / ha; it provides 84% suppression of the width of the hybrid
    3806182
    herbicide torture after germination. In this case, the following results were obtained.
    Example 2. Suppression of Pennsylvanian peach in maize (Table 1).
    Example 3. Suppression of the width of the hybrid in sorghum (Table 2).
    Example 4. Suppression of the width of the hybrid in sorghum (Table 3).
    Example 5. Suppression of breadth in sorghum (Table 4).
    To show reduced 10
    compared with the volatility of the commercial dimethyl-amine salt DJCAMBA, experiments were carried out with these compounds. Example 6. The dimethyl-amine salt of 14,.-B1CAMBA (DMA) and 2- (2-aminoethoxy) ethanol salt of 14C-DJCAMBA is obtained. Compounds are applied to glass Petri glasses in a concentration of
    0
    five
    5 approximately 1134 g / ha and soak.
    0
    five
    at a relative humidity of 70-90%. Samples are taken through O, 2, 5, 15 and 30 days to determine the amount of radiocarbon left in the petri dishes, and the following results are obtained (Table 5).
    At 50 ° C, the chemical stability of the DtCAMBA salt of the invention is determined and the following results are obtained:
    Time days
    ABOUT
    7
    14
    28
    56
    84
    Dicamba is currently used commercially in the form of dimethyl ammonium salt (DMA). As can be seen from the description of this application, the proposed salt is used as a herbicide, and in lower doses than the known salt. For example, the dose of use of compounds
    DJCAMBA,% 39.6 40.1 39.9 39.5 39.4 39.5
    which causes an 85% suppression of the Pensilvian recipe in corn, while the known salt provides only 40% suppression at the same dose. In addition, the proposed salt is more stable at a dose of 145.75 g / ha; it provides 84% suppression of the width of the hybrid
    in sorghum after 10 days, 40% suppression after 31 days and 31% suppression after 49 days (example 2), while the known dimethylammonium salt provides 73% suppression at the same dose. After 10 days, 0% rejection after 31 days or 0% rejection after 49 days (example 3).
    Moreover, the data of Example 6 demonstrate that the salt of the bol is more stable and less volatile than the known dimethylammonium salt of DjCAMBA. Low volatility with a separate advantage; a more volatile compound will migrate from the floor on which it is applied to the floors adjacent to the corn and will damage them, for example, soybean floors, for which DJCAMBA salts are very harmful. However, a compound with lower volatility will be more conserved on the crop, such as corn with sufficient penetration, on the treated fields, to destroy the weeds listed in the application.
    Below are the comparative data of the proposed salt with the corresponding salt of 2-hydroxyethylamine and dicamba, which is closest to that known compared to all other salts.
    Example 7, proposed below, shows that the proposed salt is more preferable than the known one in terms of volatility.
    Example 8 shows the advantage of a salted salt over the known, such as reainit, which promotes the ripening of sugar cane with high purity of juice.
    Example 7. Plants of soybeans are located in the neighborhood, but not in the immediate vicinity, and Petri drags, which are applied, respectively, or known salt of 2-hydroxyethylamine and DjCAMBA, or the proposed salt.
    In tab. 6 below shows the phytotoxic effect of these compounds. It can be seen that% lesion of soybob from the 2-hydroxy salt side
    0 5
    P
    five
    five
    ethylamine is significantly higher than that of the proposed compound with the same contact time, therefore, the proposed compound is less volatile than the known salt (AEch-).
    Example 8 Sugarcane plants are exposed to the salt of 2- (2-hydroxyethoxy) ethylamine and DICAMBA or the salt of 2-hydroxyethylamine DICAMBA. The cane is then subjected to testing to control the purity of the juice or% soluble solid, which is cane sugar. The proposed salt gives an increase of 9.26%, while the known salt gives an increase of only 4.27%.
    The results show that the compound according to the invention has a lower volatility than the previously known salts of DICAMBA, excellent chemical stability and is suitable as a herbicide.
    In addition, the salt of 2- (2-hydroxy-ethoxy) ethylamine and DICAMBA is unique in terms of its high solubility in water. It is almost easy to get a solution containing 2721.6 g of salt in 4 liters of water. This makes it easy to prepare highly concentrated solutions without the need to add additives or solvents.
    In addition, the salt is readily soluble in such organic solvents as butyl cellosolve, 2-ethyl-1-hexanol, and cyclohexanone. This allows formulation of emulsifiable concentrates containing the above amount of salt per liter of solvent.
    Also valuable is the fact that the salt according to the invention) has a smell.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    A method for producing a salt of 2- (2-hydroxyethoxy) ethylamine and 3,6-dichloro-2-methoxybenzoic acid, characterized in that 3,6-dichloro-2-methoxybenzoic acid is reacted with 2- (2- hydroxy-1-ethoxy) ztsh: amine.
    Salt on offer
    table 2
    According to the offer
    haemom
    way
    Control
    Table 3
    Table 4
    Connect, DaysDay
    2 I 7 1 15 I 30 J
    Proposed 99.42 99.23 97.63 100.71 97.01 1257
    DMA91.52 87.16 90.35 90.42 79.86 180
    Table 6
    Ex-Damage%
    position h 1
    The proposed connection (AE.)
    1.5 GS
    18О50
    221070
    Table 5
    类似技术:
    公开号 | 公开日 | 专利标题
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    同族专利:
    公开号 | 公开日
    PL256442A1|1987-06-01|
    BR8505886A|1986-08-12|
    AU5000485A|1986-06-05|
    DD246245A5|1987-06-03|
    DK169027B1|1994-08-01|
    EP0183384A1|1986-06-04|
    NZ213901A|1988-01-08|
    DK542885D0|1985-11-22|
    RO92258A|1987-08-31|
    DE3564258D1|1988-09-15|
    HU202180B|1991-02-28|
    ZA858264B|1986-08-27|
    PL145095B1|1988-08-31|
    EP0183384B1|1988-08-10|
    CA1242748A|1988-10-04|
    AU585910B2|1989-06-29|
    BG46451A3|1989-12-15|
    AT36315T|1988-08-15|
    HUT42049A|1987-06-29|
    ES8606237A1|1986-04-16|
    US5175353A|1992-12-29|
    CS261892B2|1989-02-10|
    ES549239A0|1986-04-16|
    UA7088A1|1995-06-30|
    MX163240B|1992-03-23|
    DK542885A|1986-05-27|
    MY101799A|1992-01-31|
    引用文献:
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    US3056669A|1957-06-03|1962-10-02|Dow Chemical Co|Composition and method for modifying plant growth|
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    法律状态:
    2007-09-20| REG| Reference to a code of a succession state|Ref country code: RU Ref legal event code: MM4A Effective date: 20041126 |
    优先权:
    申请号 | 申请日 | 专利标题
    US67462884A| true| 1984-11-26|1984-11-26|
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