• 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:
    FUNGICIDE MEANS in the form of an emulsifiable concentrate, containing the active ingredient carboxylic acid anilide derivative and emulsifier, characterized in that, in order to enhance the fungicidal activity, it contains a compound of the general formula O OR {1} 4; i, VL 0 as a carboxylic acid ailide derivative where R is methyl, ethyl; Rf is hydrogen, Zmetil, Zethyl; chlorine, methyl; R; j is hydrogen, 3 methyl, and as an emulsifier polyoxyethylene sorbitan monooleate with the following radicals: R is methyl, ethyl; R | is hydrogen, 3-methyl, 3-ethyl, R-methyl, H-hydrogen, or ligninsulf (L. sodium phonate, with the following meaning from the radicals: R, methyl, hydrogen, 3-methyl; chlorine, methyl, and hydrogen, 3-methyl, with a ratio of components equal to 80:20.
    公开号:SU1019989A3
    申请号:SU802983471
    申请日:1980-09-23
    公开日:1983-05-23
    发明作者:Цее Бернд；Теобальд Ганс；Аммерманн Эберхард；Поммер Эрнст-Гейнрих
    申请人:Басф Аг (Фирма)；
    IPC主号:
    专利说明:

     with
    00
    with The invention relates to chemical plant protection agents, more specifically to fungicidal agents based on carboxylic anilide derivatives. A fungicidal agent based on aniline derivatives and an emulsifier GJ is known. The agent in the form of an emulsifiable concentrate, based on carboxylic acid anilides and emulsifier C2}, is closest to the proposed one. However, these fungicidal agents have insufficient activity at low concentrations. The purpose of the invention is to enhance the fungicidal activity of the drug. To achieve this goal, the proposed fungicidal agent is used in the form of an emulsifiable concentrate containing a compound of the general formula 1: as a carboxylic acid anilide derivative. R / is hydrogen, 3-methyl, 3 ethyl; Cd-chloro, methyl; Rj is hydrogen, 3-methyl, and as an emulsifier, polyoxy ethylene sorbitan monooleate with the following radicals: R is methyl, ethyl; R is hydrogen, 3 methyl, R is methyl and R is hydrogen, or sodium lignin sulfonate with the following radical values: R is methyl; p .. is hydrogen 3-methyl; chlorine, methyl and I - hydrogen, 3-methyl, with a ratio of components equal to 80:20. The proposed fungicidal agent is obtained by known methods, for example by mixing the components. The compounds of formula 1 can be obtained by reacting an anilide derivative of the formula OK G}) where R, Rj, Rj have the indicated values with an isoxazolylcarboxylic acid derivative of the formula - -O-P-R where RY is methyl or ethyl; A - nucleophilic substitutable waste group, c. if necessary, in the presence of a solvent, inorganic or organic base, and a catalyst at 0-120 ° C. Preferred solvents include methylene chloride, chloroform, 1,2-dichloroethane, chlorobenzene, cyclohexane, petroleum ether, benzene, toluene or xylenes, ethyl acetate, acetonitrile, dimethylsulfoxide, acetone, methylethylketone, dietilovy ether, tetrahydrofuran, dioxane or mixtures these solvents. It is advisable to use solvents in an amount of 100-2000 wt.%, Preferably from 100 to 10000 weight at the rate of c.a starting materials of the formula 1J and 11.1. Preferred inorganic or organic bases are potassium carbonate or. sodium, sodium hydride, trimethylamine, triethylamine, M, K-dimethylaniline, N; N-Dimethylcyclohexyl silumin, N-methylpiperidine, pyridine, 1,2, -triazole, imidazole. Sodium bromide, potassium iodide, imide ash, 1,2,4-triazole, A-dimethylaminopyridine or mixtures of these substances can be used as catalysts. Preferably, the anilide derivative of the formula P takes 0.9 1.3 the acid derivative of the formula 11J and, if necessary, 0.5-2 mol of base and 0.01-0.1 mol of catalyst. The reaction is usually carried out at 0-120 ° C, for 1-60 hours without pressure or under pressure, continuously or periodically. Example 1. In a solution of 20.7 wt. CH; H- (1-methoxycarbonylethyl) -2, 6-dimethylaniline 100 ob.h. toluene is added dropwise 15.2 vol. triethylamine and then a solution of 16 weight.h. 5-chloride 3-methylisoxazyl carboxylic acid in 30 parts by volume toluene. The temperature of the reaction mixture rises to. After stirring at room temperature for two hours, 50 vol. Hours is added. water.
    The organic phase is separated, washed three times with water, each in an amount of 50 parts by volume, then dried and concentrated. The remaining oil is distilled under reduced pressure.
    FVpi 0.005 mbar and 170-17 C receive, 1 weight.h. H- (1 methoxycarbonylethyl), 6-dimethylanilide) 3-methylisoxazolyl-5-carboxylic acid.
    Calculated, |: С 6А, 5; H 6.4;
    N8.9 ..
    0 „H-„ O.M2 (316.3).: С 6It, 6; H 6.3;
    N 8.9.
    The following compounds of formula 1 can be prepared analogously:
    ™, G .0
    he
    0: 1- f-Ui
    II hg. " V l
    s
    V
    are given in table. one.
    The high fungicidal activity of the proposed agent is visible from the following examples.
    . Example 2. 80 wtL active ingredient listed in table. 2, mixed with 20 wtD of polyoxyethylene sorbitan monooleate. The resulting mixture is diluted with water to the indicated in table. 2 concentrations of active ingredient. This preparation is used to spray the leaves of Yubil r cultivars grown in pots and, after drying, the leaves are dusted with spores of wheat powdery mildew (Eryslphe graminis var. Tritici).
    The test plants are then placed in a greenhouse at 20-22 ° C and relative humidity 75-80. After 10 days. The degree of development of the powdery mildew fungi is determined.
    The results of the experiment are given in table. 2..
    Example 3. In wt.% The active substance specified in the table. 3. Mix with 20% by weight sodium ligninsulfonate. The resulting mixture is diluted with water to the indicated in table. 3 concentrations of active substance. This preparation is used to spray the leaves of tomato varieties of plant 0 Professor Rudlov. After drying, the leaves are affected with a suspension of zoospores of the fungus Phytophtora infestans. The plants are then placed in a water-saturated chamber at 16–18 ° C. After 5 days. the disease on untreated, but also affected, control plants. Since it is strongly developed, it is possible to determine the fungicidal effect of the substances; 0 The results of the experiment are visible from the table. 3
    Thus, the proposed fumgitsidny agent has a high fungicidal activity at low concentrations.
    sn,
    sn
    sn sn
    H
    CHj
    H
    sn,
    H
    H
    C1
    sn,
    3-CH, 5 BH
    H
    bp / 0,005 mbar
    T. Kip. 170-17 ° C
    3 / 0.01 mbar
    Butter
    i m.p. 75-77 ° C
    M.p. 85 ° С
    Butter
    M.p. 88-90С
    Control without processing
    Note: E - fungal infection
    table 2
    missing; 5 complete defeat; A - C - (- Metoy-bicarbonylU-M- (furan-2 -carbonyl -2,6 dimethylaniline (iridescent; B - N - (1-methoxycarbonyl 3TwO-Vl- (pyridine-3 carbonyl) -2-methyl-6-hlopaniline (known)
    T a b l and c a. 3
    权利要求:
    Claims (1)
    [1]
    A FUNGICID AGENT in the form of an emulsifiable concentrate, εογ containing the active ingredient - a carboxylic acid anilide derivative and emulsifier, characterized in that, in order to enhance fungicidal activity; it contains, as a derivative of a carboxylic acid anilide, a compound of the general form - »эти Chel;
    hydrogen, 3-methyl, 3 “3tyl; chlorine, methyl;
    hydrogen, 3 ”methyl, as an emulsifier - polyoxyethylene sorbitan monooleate with the following radicals: R - methyl, ethyl; Rj is hydrogen, 3-methyl, 3-ethyl, R ^ -methyl and K3-hydrogen, or sodium ligninsul * phonate with the following radicals: R-methyl; Rj is hydrogen, 3-methyl-; chlorine, methyl and Ry hydrogen, 3-methyl, with a component ratio of 80:20.
    with CO
    Q0 CO
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    同族专利:
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    引用文献:
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    DE3133418A1|1981-08-24|1983-03-10|Basf Ag, 6700 Ludwigshafen|THIAZOLYL AND ISOTHIAZOLYLCARBONIC ACID ANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
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    US4504486A|1982-05-17|1985-03-12|Chevron Research Company|3-Isoxazolin-5-one fungicides|
    US5196046A|1984-07-26|1993-03-23|Rohm And Haas Company|N-acetonyl-substituted-amides|
    US4863940A|1984-07-26|1989-09-05|Rohm And Haas|N-acetonyl-substituted amides and phytopathogenic fungicidal use thereof|
    DE3506814A1|1985-02-27|1986-08-28|Basf Ag, 6700 Ludwigshafen|5-ISOXAZOLE CARBONIC ACID AMIDES, THEIR PRODUCTION AND USE AS FUNGICIDES|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792940189|DE2940189A1|1979-10-04|1979-10-04|ISOXAZOLYLCARBONIC ACID ANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
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