• 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:
    The present invention relates to novel N- and optionally N'-substituted (N-dichloroacetyl)glycine amides of the formula I with antidote action, to antidote compositions containing such compounds, to selective herbicide compositions containing these antidotes together with herbicidally active compounds and to a method for treating cultivated plants with said compositions.
    公开号:SU1395138A3
    申请号:SU843814616
    申请日:1984-11-23
    公开日:1988-05-07
    发明作者:Байус Юдит；Балог Карой；Бартфаи Жужанна；Береш Илона；Домбаи Жолт；Грега Эржебет；Лерик Ерне；Надь Йожеф；Пастор Карой；Тарпаи Дьюла；Таши Ласло；Тот Иштван；Урсин Эстер
    申请人:Эсакмадьярорсаги Ведьимювек (Инопредприятие)；
    IPC主号:
    专利说明:

    00
    wed
    with
    00

    cm
    The invention relates to organic chemistry, namely to a method for producing new N -substituted K- (dichloroacetyl) glycinamides of the general formula
    2
    "XC1
    with cHj-N-sn
    R P C1
    oh oh
    (I)
    where Ef and R ,. - independently of each other lower alkip or allyl, which can be used as antidotes in herbicidal agents.
    The aim of the invention is to develop an accessible method for producing N -substituted H- (dichloroacetyl) glycine amides, which are effective antidotes used in herbicidal agents.
    Example 1. A B-equipped with a stirrer, thermometer and dropping funnel of a 500 ml round-bottomed flask cooled 15.4 g of N, H-diallyl-glycinamide, 100 ml of dichloromethane and a solution of 4.4 g of sodium hydroxide in 100 ml in an ice bath to 5 ° C, after which, with vigorous stirring, this mixture is mixed with 15.0 g of dichloroacetyl chloride, and the temperature of the mixture is kept lower. After the addition is complete, the mixture is stirred at room temperature for another 4 hours, then the organic phase is separated, washed twice with water, dried over sodium sulfate, and then the solvent is distilled off in vacuo. As a result, 24.1 g (91%) of N, N-diallyl-K - (dichloro-acetyl) glycinamide (l) are obtained. Degree chig. strty (according to gas chromatograph - 1.5250, ie, 98.8%.
    Calculated,%: N 10.56; C1 26.79,
    Found,%: N 10.48; C1 26.71.
    Example 2. To a cooled mixture (up to 5 ° C) of 10, 2 g of N, n-dimethylglycinamide, 100 ml of benzene and a solution of 6 g of sodium carbonate in water was added dropwise, with stirring, 16.0 g of dichloroacetyl chloride; the temperature of the mixture is kept below 10 ° C. After the addition is completed, the mixture is stirred for another 3 hours at room temperature. The organic phase is then separated, washed with water, dried over sodium sulfate, and benzene is distilled off. 17.0 g (80%) of N, N -DIFY are obtained as a result.
    0
    five
    0
    five
    0
    five
    0
    five
    0
    five
    Methyl-N - (dichloroacetyl) glycinamum, t. pcs. about 36-40 C. The degree of purity (gas chromatography) is 96.8%.
    Calculated,%: N 13,14; C1 33.33.
    Found,%: N 13.25; C1 33.01.
    Example 3. To a mixture cooled to 5-10 ° C, 13.0 g of N, N -dimethylglycinamide, 100 ml of toluene and 11.0 g of trimethylamine were added dropwise with stirring and ice-cooling to 16.5 g of dichloroacetyl chloride. After completion of the reaction, the mixture is washed with water, dried over sodium sulfate and the solvent is distilled off. As a result, 21.7 g (90%) of N, N-diethyl-N - - (dichloroacetyl) glycinamide, m.p. 79 - 82.5 ° C. The degree of purity (gas chromatography) is 98.2%.
    Calculated,%: N 11.61; 01 29.46.
    Found,%: N 11.69; C1 29.78.
    Other compounds listed in Table 2 were prepared analogously. one.
    The proposed herbicidal compositions are predominantly emulsion concentrates (EC), wettable powders (SP) granulated products, aqueous or oil suspensions. In order to illustrate the preparation of preparations containing opposite in accordance with the invention, table. 2 shows some examples.
    In tab. 3 shows the composition of the EC, prepared from compounds of General formula (I).
    Experiments carried out to clarify the relationship between doses and activity have shown that according to the invention of the compound in doses of 0.5-64% (applied herbicide 100%) leads to a significant improvement in the results.
    Example 14. A series of experiments was carried out in growth vessels with an area of 1.13 dm with four parallel repetitions. In each case, the vessels were filled with 400 g of air and sifted through a sieve with 2 mm openings on meadow soil with a humus content of 1.4% and with a pH value of 7.5, (Arani 61 potentiality of the soil). The plants used in the dough are sown in these vessels: maize MVTC 596 (Zea mays) 15 grains per vessel; Green mustard (Sefaria viritus) 0.5 g per jar. A chemical treatment is then carried out by spraying.
    The amount applied is calculated per hectare. 20 ml of water are each used to prepare the spray liquid.
    After chemical treatment, another 100 g of soil is placed in the vessels and poured to a water capacity of 65%. During cultivation through daily irrigation, care is taken to maintain humidity at a constant level. A high-pressure mercury lamp (HgMI / D 400 W) is irradiated every day. The average daily temperature is 25 ° С (minimum 23 ° С, maximum 27 ° С). To evaluate experiments
    the length of the shoots and the morphological abnormalities are determined. The results obtained in the experiments are presented in Table 5-10.
    Maize is treated with 5.6 l / ha ERTS, as well as those indicated in the table. 5 amounts of a compound according to example 1 and R 25788.
    A similar method is applied with butylate (K, H-diisobutyl-3-ethylthiol-carbamate) with a consumption rate of 6.0 l / ha, as well as with counterweight R 25788. The results are presented in Table. 6 (5 percent value for untreated control plants).
    Similar experiments are repeated with fernolate and, K-di- (n-propyl) (n-propane 1) -thiolcarbamate | at the norm, control tests without a stroke of 4.0 l / ha were also performed. The obtained results of the treatment. As substances for are presented in Table. 7. Comparisons R-25788 (M, H-diallyl-2,2-dichloroacetamide) is used.
    The evaluation was performed on the 10th day after the treatment by measuring the length of the shoots and assessing the morphological changes. The following scale is used for evaluation: 100% healthy ma-. is; 87% - weak coagulation of leaves,
    distortion; 75% - average curvature of zo-bamat) at consumption rates of 8.0 l / ha, stem, leaf deformation; 50% - half- Results are presented in table. 9.
    Similar experiments were repeated with 2-chloro-2, 6 -distil-K- (methoxymethyl) acetanshidine with apa-chloro at a rate of pacxo-ri / 25 and 1.5 l / ha. The results (data as a percentage of untreated control plants) are presented in Table. AT.
    Similar experiments were repeated with etiolate (K, K-diethyl-5-ethylthiol carcinoma, growth and development in a state of calm.
    Green as a single leaf weed; mustard green dies during all treatments, i.e. the protecting effect of compounds (l) does not extend to this species.
    In tab. 4 shows the length of the shoots and the appearance of the plants (as a percentage of the untreated control plants). The treatment was carried out using 5.5 l / ha EPTC (L, M-di- (n-propch1) -3-ethylcarbamate), to which in one case 8% was added, a. in another case, 16% of a specific antidote. Example 15. Dose and activity.
    Using compound., As in example 1, the activity of compounds of general formul (l) is examined in various doses. For comparison, experiments were also carried out with non-countering agents containing EPTC, ferpolate, butylate, alachlor, ethiolate and acetochlor, as well as with agents containing these biologically active substances and the known counterpart R 25788.
    35
    40
    Analogous experiments carried out with acetochlore 2-chloro-2 -methyl-b-ethyl- -T} - (ethoxymethyl) acetanilide 1, the flow rate of 1.5 l / ha. The results are presented in table. ten,
    The data in the tables below show that the new compounds according to the invention, in particular at doses of 0.5-2.0%, are more beneficial than the known agent R 25788. In the higher concentration range, it may not be detected with static tests are the difference between the two opposites. In amounts of 4-16%, they provide healthy and free from the presence of adverse symptoms of maize.
    The novel compounds also contribute to the selectivity of thiol carbamates and chloroacetanilides. The phytotoxic properties are eliminated; While the herbicidal activity is preserved.
    权利要求:
    Claims (1)
    [1]
    55 claims
    The method of obtaining N -substituted N- - (dichloroacet) glycine amides of the general formula
    50
    ten
    five
    Similar experiments are repeated with fernolate and, K-di- (n-propyl) (n-propane 1) -thiolcarbamate | with a consumption rate of 4.0 l / ha “The results obtained are presented in Table. 7
    bamah) at consumption rates of 8.0 l / ha, the results are presented in table. 9.
    Similar experiments were repeated with 2-chloro-2, 6 -distil-K- (methoxymethyl) acetanshidine with apa-chloro at a rate of pacxo-ri / yes 1.5 l / ha. The results (data as a percentage of untreated control plants) are presented in Table. AT.
    Similar experiments were repeated with ethiolate (K, K-diethyl-5-ethylthiolcar5
    0
    Analogous experiments carried out with acetochlore 2-chloro-2 -methyl-b-ethyl- -T} - (ethoxymethyl) acetanilide 1, the flow rate of 1.5 l / ha. The results are presented in table. ten,
    The data in the tables below show that the new compounds according to the invention, in particular at doses of 0.5-2.0%, are more beneficial than the known agent R 25788. In the higher concentration range, it may not be detected with static tests are the difference between the two opposites. In amounts of 4-16%, they provide healthy and free from the presence of adverse symptoms of maize.
    The novel compounds also contribute to the selectivity of thiol carbamates and chloroacetanilides. The phytotoxic properties are eliminated; While the herbicidal activity is preserved.
    5 claims
    The method of obtaining N -substituted N- - (dichloroacet) glycine amides of the general formula
    0
    -sn, -sn
    Ooh
    K-c-CHt ira R2 „X -

    about
    where R, and R - independently of each other, lower alkyl shsh allyl; characterized in that the compound has a general form; & 1
    where R, and R have the indicated meanings, are reacted with dichloroacetyl chloride in the presence of an organic solvent and a base as a hydrogen chloride acceptor.
    Table 1
    Table 2
    ERTS 72EK
    ERTS + R25788
    ERTS + connection example
    one
    2
    3
    4 5
    6
    eight
    9
    10 11 12 13
    five%
    Note: a - in comparison with untreated control plants there are no significant deviations (95% certainty); (B) in comparison with the processing of ERTS without significant deviations (with 95% confidence).
    Table3
    Table 4
    B
    100 a, b
    90 a, b

    78 b
    48
    65 b
    41
    36
    38
    68 b
    B 98 a, b
    B 89 a, b
    50
    98 a, b
    100 a, b 100 a, b 100 a, b 98 a, b 81 b
    63b 67 b 60
    64
    65Ъ 80 Ъ 88 а, Ъ
    99a, b
    100a, b 97 a, b
    99a, b 87 a, b 55
    57 55
    70 b 75 b
    100a, b 100a, b
    10.6 13.3
    11.7
    13.9
    + 15 + 12
    eleven
    5% 16.3% between any SJD combining w
    The length of the shoots of maize, processed - External maize of maize treated with EPTS without contra, 52% of EPTS without contra, 63%
    1395138
    12
    Continued .tab.5
    5% 13.8% between any SD combinations
    13
    1395138
    14 Table 7
    15
    Shoot length (etiolate without counter) 67%
    1395138
    sixteen
    Continuation of table.8
    Appearance (etiolate without counter) 77%
    Shoot length (acetochlor without back di) 44%
    Appearance (without acetochlor) 68%
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    法律状态:
    优先权:
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