• 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:
    This invention relates to a chemical agent for controlling undesirable vegetation. The tool has a herbicidal and growth-regulating effect and can be used in agricultural and industrial areas, railways, forest and ornamental groves. The invention allows to increase the efficiency of action due to the fact that the agent contains 25 May as an active principle. % of the sulfonic acid derivative of the formula u, O ys & JN -, l, j n; h, s to and. or Rr, x N S - N S N G 1 I J J NN I. where RI is I, CI, F, Br, CPh, CH3O, CH3CO, CH3CO2. С2Н5ОСО, (СН3) 2СНОСО, N. СН3, СНзО, СНзСО, СНзОСО, С2Н50СО, (СНз) 2 СНСОСО, Н, СНз, (СНзЬН, CH3S; R2 - Н, СНз; Нз - Н, Be, F; Ri - Н CH3; RS - H, CI, F, Br, N02. SNE. C2H5. SNZO; R6 - H, CH3. C2H5, CH3NHCO, N (C2Hs) 3, R - H, CH3, C2H5, phenyl; RB - H , CH3, C2Hs, phenyl; X is oxygen or sulfur. The product also contains 60% by weight of kaolin, 10% by weight of silicic acid, 3% by weight of Ca-salt of lignosulfonic acid and 2% by weight of Na-salt of methyl oleyl - urate 5 tabs of C
    公开号:SU1658808A3
    申请号:SU874203886
    申请日:1987-12-18
    公开日:1991-06-23
    发明作者:Крюгер Мартин；Вестерманн Юрген；Арндт Фридрих；Кеттер Клеменс；Рис Ричард
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to chemical means of controlling undesirable vegetation used in agricultural and industrial areas, railways, roads, forest and ornamental groves, and the like.
    Means possesses herbicidal and growth-regulating action.
    The aim of the invention is to increase efficiency.
    PRI mme R 1. 5,6-Dimethyl-7-oxo-6,7-di-hydro- {1,2,4-triazolo- 1, 3,5-triazol
    im-2-sulfonic acid- (M-methyl-2,6-dichloroanilide).
    1.30 g (3.4 mmol) of 5-amino-1-methylaminocarbonyl-1,2,4-triazole-3-sulphonic acid ta- (N-methyl-2,6-dichloropanilide) is stirred in 10 ml of orthoacetic triethylether with 5 drops of glacial acetic acid for 12 hours at 120 ° C. The insoluble precipitate is filtered off and drained. The product is chromatographed on a mixture of hexane and ethyl acetate over a silica gel.
    Os
    ate
    00 00
    about
    00

    with
    The output of 0.77 g (56% of theoretical). M.p. 286-288 ° C.
    Calculated,%: C 38.72; H 3.00; N 20.84; S 7.95; CI 17.59.
    Found,%: C 38.54; H 3.10; N 20.79: S 8.01; CI 17.59.
    a) 5-Amino-1-methylaminocarbonyl-1,2,4-triazole-3-sulfonic acid (M-methyl-2,6-dichloroanilide).
    2.0 g (6.2 mmol) of 5-amino- {1,2,41-triazole-3-sulfonic acid- (M-methyl-2,6-dichloroanilide) are suspended in 30 ml of tetrahydrofuran and mixed with 0 , 5 ml (8.5 mmol) of methyl isocyanate and 0.9 ml (6.5 mmol) of triethylamine. The mixture is stirred for 3 hours at room temperature and left overnight. The solution is concentrated and chromatographed with a mixture of hexane and ethyl acetate via silica gel.
    The output of 1.36 g (58% of theoretical). M.p. 220-222 ° C.
    Calculated,%: C 34.8; H 3.19; N 22.16; S 8.46; CI 18.70.
    Found %: C 34.8; H 3.64; N 21.99; S 8.13; CI 18.33.
    b) 5-Amino-1,2,4-triazole-3-sulfonic acid- (M-methyl-2,6-dichloranilide)
    9.80 g (22.8 mmol) of 1-acetyl-5-amino-1,2,4-triazole-3-sulfonic acid-2,6-dichloroanilide, the pyridine salt is dissolved in 300 ml of dimethylformamide and 0, 89 g (29.7 mmol) of 80% sodium hydride in portions at room temperature. Stir for 30 minutes and add 1.7 ml (27.8 mmol) of methyl iodide. The mixture was left to stand for a day and concentrated. The precipitate is transferred to a 2 N sodium hydroxide solution and placed in a slightly acidic 3 N hydrochloric acid solution. The crystals are filtered off with suction, washed with water and ether and recrystallized from acetonitrile.
    The output of 3.4 g (46% of theoretical). M.p. 254-255 ° C.
    Calculated,%: C 33.55; H 2.82; N 21.74; 59.95; CI 22.01.
    Found,%: C 33.95; H 3.10; N21.63; S 10.08; CI22.18.
    PRI mme R 2. 5,6-Dimethyl-7-oxo-6,7-di-hydro-1,2,4-triazolo-1, 2. triazin-2-sulfonic acid-2,6-dichloranilide.
    3.4 g (9.0 mmol) of M- (2,6-dichlorophenyl) -5- (1-ethoxyethylideneamino) -1H-1,2,4-triazole-3-sulfonamide is shaken in 70 ml of tetrahydrofuran with 0.66 ml (11.3 mmol) of methyl isocyanate and 1.3 ml (9.3 mmol) of triethylamine for 4 hours at room temperature. The crystals are sucked off, washed with a mixture of tetrahydrofuran and water (4: 1), tetrahydrofuran and ether, then dried under vacuum.
    The yield of 3.4 g (97% of theoretical). M.p. 331-334 ° C.
    Data on the proposed compounds
    presented in table 1.
    PRI me R 3. Mix 25% of the active substance, 60% kaolin, 10% silicic acid, 3% calcium salt of lignins sulfate and 2% sodium salt of M-methyl-N-oleyl taurate. The resulting wettable powder is suspended in water at the rate of 1 kg of active substance per 500 l of water. The test plants of 5 species of Helianthus and Chrysanthemum are sprayed with an aqueous suspension prior to the emergence of seedlings and after emergence. Weed destruction is estimated in the comparative scheme with points from 0 to 4 within three weeks after treatment, and the points mean: 0 - no effect; 1 — average growth retardation; 2 - a strong slowdown in growth; 3 - a complete slowdown in growth; 4 - complete destruction. 5Dose of active substance 1 kg / ha.
    The test results are presented in Table. 2-5.
    EXAMPLE 4 Seeds of monocotyledonous and dicotyledonous weeds, as well as cultivated plants of wheat (Triticum aestivum), barley (Hordeum dlstlchum) and rice (Oryza sativa) are planted in pots and covered with sandy soil containing humus. On the surface of the soil before planting nano-5 tons of suspension specified in example 3.
    After processing, the test pots are placed in a greenhouse and the test plants are grown under good growth conditions. After four weeks from the start of the treatment, plant death is evaluated. Untreated control samples are used as a comparison.
    As can be seen from the table. 3, all weeds were destroyed without any damage to cultivated 5 plants.
    In tab. 4 principles of designation: score 0 - no effect; 4 - destruction of plants, Tr - Triticum aestivum; But - Hordeum dlstichum; Or - Oryza sativa; Se - Setaria sp; 0 He - Helianthus sp; St - Stellaria sp; Ab - Abutllon sp; Vi-Viola sp; Br - Brasslca sp; So-Solanum sp; Ma - Matricaria sp: Cy - Cyperus sp; EC - Echinochloa.
    EXAMPLE 5 Seeds of monocotyledons and 5 dicotyledonous weeds, as well as cultivated plants of wheat (Triticum aestivum), barley (Hordeum distlchum) and rice (Oryza sativa) are planted in sandy soil containing humus and covered with soil. . The aqueous suspension prepared from the proposed agent is applied to the soil surface after the plants have been planted. Soil treatment is carried out at the rate of the active substance dose of 1 kg / ha.
    After processing, the test pots are placed in t in the greenhouse and the plants are grown under good conditions. Two weeks after the treatment, plant death was evaluated. For comparison, untreated control samples are used.
    As can be seen from Table 4, all weeds were destroyed without any damage to cultivated plants.
    In the following table. 4 points means: About
    - no impact; 4 - destruction of plants, Tr - Tritlcum aestlvum; But - Hordeum distichum; Or - Oryza sativa; Se - Setaria sp; He - Hellanthus sp; St - Stellarla sp; Ab - Abutllon sp; VI - Viola sp; Br - Brassica sp; So - Solarium sp; Ma - Matricarla sp; Cy - Cyperus sp; EC - Echinochloa sp.
    P p and m e p b. Suspensions were prepared as in Example 3. Echinochloa crusgalll, Flmbrlstylls mlllacea, Paspalum distichum and Cyperus dlfformis were used as test plants at a stage of from 2 to 5 leaves. Dose of the active substance 1 kg / ha
    In tab. 5 marks mean: O
    - no impact; 1 - low impact (damage); 2 — mean influence; 3 - strong influence; 4 - complete destruction, Her - Echinochloa - crushgalll: Fl - Fimbritylis miHacea; Pa - Paspalum distichum, Cy - Cyperus dlfformis.
    权利要求:
    Claims (1)
    [1]
    Claims of the invention: Herbicidal and growth regulating agent, comprising as active
    start sulfonic acid derivative. containing condensed heterocycles, carrier and surfactant, characterized in that, in order to increase the effectiveness of the action, it contains the compound of the formula as active principle
    "L
     Sr, N -N
    OR
    where Ri is I, Cl, F, Br, CPH, CH3O, CH3CO, 15 CH3SO4, C2H5-CCA, (CH3) 2CHNOSO, H, CH3, (CH3CH2, CH3S:
    R2 is H, CH3;
    Рз - Н, Br, F;
    R4-H, CH3;
    Rs - H, Cl, F, Br, N02, CH3, C2H5, CH3O;
    Re - H, CH3, C2Hs, CH3MNSO, N (C2Hs) 3.
    R - H, CH3, C2Hs, phenyl,
    Re - N. СНз, С2Нб, phenyl;
    X - oxygen or sulfur, as a nano-element - a mixture of kaolin with silicic acid, as a surfactant - a mixture of Ca-salt of lignosulfonic acid with the Na-salt of M-methyl-N-oleyl taurate, in the following ratio of components, wt.%.
    Active start25
    Kaolin60 Silicic acid10
    Ca salt of lignosulfonic acid3 Na salt of N-methyl-Moleyl taurate2
    one
    2
    3
    four
    five
    6
    7
    eight
    9
    ten
    eleven
    12
    13
    14
    15
    sixteen
    17
    18
    nineteen
    20
    21
    22
    23
    24
    25
    26
    27
    28
    29
    thirty
    31
    32
    33
    34
    35
    4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4
    4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4
    four
    4 4 4 4 4 4 4 4 4 4 4 4
    4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4
    36 37 38
    39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 -70 71
    13165880814
    11Continue; tab. 2
    five
    Continued
    ::;:; :::: g ::::::: 1 ::: t ::; gt ;;: g; g; :: c:
    if
    15
    165880816
    Continuation of table 2
    The compound used in the known means:
    7-amino- 1, 2,4j-triazolo-1, 5-a-l, 3, 5-triazin-2-sulphoxylum-2,6-dichloranilide
    7-amino-5-methyl- Ј1, 2, 43 -griazolo- D, 3, triazin-2-sulyo-acid-2,6-dichloroanilide
    30004444444434
    40004444444434
    50003334433434 120003334334434 14 000443444 4443 1800-044 43444434 L500 034 44.43-3433 510003334333433 5500043 433 i. 4443 5900 033 434.3 3434. 690003343433434 77.1004334443444 860004343334433 Control 00 000 0000 0000
    A well-known tool containing:
    7-amino- I, 2.4 / triaino- | , 5-aJII, 3, 5-tri-aein-2 sulfonic acid-2, 6-dichloroyl and 10,000,000,000,000
    7-amino-5-methylL1 2, 4J -triato
    Lo-0, 5-aj-l, 3.5 tria Eu11-2-sulfonic acid-2, 6-dichlorannndnd0000000000000
    C l l DINSIP, NG SCH-il. - IVCMOe H tnn -. C i h) M
    Wed ds i ve:
    7-d.,, 2, PH POLH-, 5-nJ, 3,5j-h riazip-2-su; H) wk1 spot- 2, 6-dichlorannlnd
    7-aminp-5-methyl 1 - 3, 4-trnaeolo-l, 5-aJ - ,, 3, trnatn-2-sulfo-acid-2,6-dp-chlorachilnd
    7 Amino, 2, acholo-O, 5-aJ-l, 3, triazin-2-sulfonic acid a-2, 6-dichloroylide30
    7-Amino-5-methyl-fl, 2,4j-Tpna30jio-fl ,, 3,5jtriazn-2-suprapiospot-2,6-di-chloroanilide 30
    Table
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    引用文献:
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    DE2236340A1|1972-07-25|1974-02-07|Bayer Ag|Triazolo-triazine derivs - with selective herbicidal activity, prepd from 3-mercapto-4-amino-5-imino-1,2,4-triazines|
    GB1579932A|1976-05-12|1980-11-26|Ici Ltd|Herbicidal triazolotriazines|
    DD205905A1|1982-08-17|1984-01-11|Univ Rostock|PROCESS FOR PREPARING SUBSTITUTED 1,2,4-TRIAZOLO -1,3,5-TRIAZINES|
    US4565815A|1982-12-30|1986-01-21|Biomeasure, Inc.|Pyrazolo[1,5-a]-1,3,5-triazines|
    EP0330137B1|1983-11-14|1994-03-02|DowElanco|Intermediate compounds for the preparation of 1,2,4-triazolo [1,5-a]pyrimidine-2-sulfonamides|
    GR850161B|1984-01-26|1985-05-21|Dow Chemical Co|
    US4685958A|1986-05-06|1987-08-11|The Dow Chemical Company|Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]-1,3,5-triazines and compositions and methods of controlling undesired vegetation|US4954163A|1983-11-14|1990-09-04|The Dow Chemical Company|Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides|
    DE3808122A1|1988-03-11|1989-09-21|Bayer Ag|TRIAZOLOPYRIMIDINE-2-SULPHONAMIDE|
    US5391759A|1988-12-19|1995-02-21|Dowelanco|Preparation of 5-acylamino-1,2,4-triazole-3-sulfonamides|
    DE3916469A1|1989-05-20|1990-11-22|Basf Ag|SULPHONAMID|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19863644343|DE3644343A1|1986-12-19|1986-12-19|6,7-DIHYDRO-TRIAZOLO TRIAZINE-2-SULPHONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS AGENTS WITH HERBICIDES AND REGULATING GROWTH|
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