• 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:
    Beim Verfahren zum Schützen von Kulturpflanzen gegen schädigende Wirkungen von Agrarchemikalien werden Chinolinderivate der Formel worin R1, R2 und R3 unabhängig voneinander Wasserstoff, Halogen, Nitro, Cyan, Alkyl oder Alkoxy, R4, R5 und Re unabhängig voneinander Wasserstoff, Halogen oder Alkyl, X einen aliphatischen, acyclischen, gesättigten Kohlenwasserstoffrest mit 1 bis 3 Kohlenstoffatomen und Y eine Carboxylgruppe oder ein Salz davon, eine Mercaptocarbonylgruppe oder ein Salz davon, eine Carbonsäureestergruppe, eine Carbonsäurethiolestergruppe, eine unsubstituierte oder substituierte Carbonsäureamidgruppe, ein cyclisiertes, unsubstituiertes oder substituiertes Derivat einer Carbonsäureamidgruppe oder eine Carbonsäurehydrazidgruppe oder X und Y zusammen einen unsubstituierten oder substituierten Tetrahydrofuran-2-on-Ring bedeuten, unter Einschluss ihrer Säureadditionssalze und Metallkomplexe, oder Mittel, welche solche Derivate enthalten, eingesetzt. Es werden auch neue Chinolinderivate und ihre Herstellung beschrieben.
    公开号:SU1658807A3
    申请号:SU833592351
    申请日:1983-05-06
    公开日:1991-06-23
    发明作者:Хубеле Адольф
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to the protection of cultivated plants from the damaging effects of herbicides and may be used in agriculture.
    The purpose of the invention is to increase the protective effect of herbicide damage to a number of pyridyloxyphenoxypropionic acids.
    The compounds of the invention are particularly suitable for protecting crop plants from the damaging effects of herbicides of the formula
    Have
    HN
    x1.1 S-Q-o
    J-O-CH-COOR (A)
    where XT is hydrogen or halogen;
    X2 is hydrogen, halogen or trifluoromethyl.
    Q fragment M- or -CH-;
    R - St-C-alkyl. which is unsubstituted or substituted with C1 C4 alkoxyl; kenyl; Cz C4-alkynyl or C h, where Ri3 Ci is C4-alkyl; Ri4 Ci-C-alkyl or Ria and Ri.i BM-j .-. Those mean Ci-Cs-alkylene.
    As cultivated plants that can be protected by quinoline formulas (I)
    Agricultural Chemicals. for example, cultivated millet, rice, corn, cereals (wheat, rye barley, oat), cotton, sugar beet, sugar cane and soybean are used.
    Particularly noteworthy is the protective effect of compounds of formula (I) in the case of crops against the damaging effects of herbicides, for example, diphenyl ethers and substituted complex
    |
    fe
    ioo
    Od o
    Ksl
     with
    pyridyloxyphenoxypropionic acid esters, especially 2-propynyl ester (3,5-dichloropyridyl-2-hydroxy) -phenoxy-propionic acid.
    A method of protecting cultivated plants when using compounds of formula () is that cultivated plants, parts of these plants, or intended for cultivation of these cultivated plants, the soil before or after adding plant material to the soil is treated with a compound of formula (I) or a tool that contains such a compound . The treatment can be carried out before, simultaneously with or after applying agricultural chemicals.
    A compound of formula (I) is prepared. The compound of the formula
    -
    AND)
    where RI, R2, Ra, R4, RS and Re are as defined for formula (I);
    M is hydrogen, an alkali metal or alkaline earth metal atom, introduced into interaction with a compound of the formula
    Z-X-Y (III), where X and Y have the indicated meanings;
    Z is a cleavable residue, or for the preparation of compounds of formula (I) in which Y is COORy, an acid halide, compounds of formula
    | 3 1 Ь х-Ч-Ч Р
     N A (W
    ohs about
    Hal
    where RI, R2, Ra, Ri, Rs, Re, and X have the indicated meanings;
    Na is a halogen atom,
    introduced into interaction with the compound 45 of the formula
    M —O — R, (V), where R has the indicated meaning;
    M - hydrogen, alkali metal or alkaline earth atom. 50
    For the preparation of compounds of formula (I) in which Y is -COSRs, an acid halide of the compound of formula
    where RI, R2, R3, R4. Rs, Re and X have the indicated meanings;
    Hal is a halogen atom,
    introduced into interaction with the compound of the formula
    M-S-RB, (vii)
    where Re has the specified value;
     hydrogen, alkali metal or alkaline earth atom,
    For the preparation of compounds of formula (I) in which Y is -CONRgRto, an acid halide of a compound of formula
    R

    15
    (M)
    Ohh Hal
    where RI, R2, RS, RI, Rs, Re and X have the indicated meanings;
    Hal is a halogen atom,
    introduced into interaction with the compound of the formula
    HNRgRio (IX), where Rg and Rio have the indicated meanings.
    To obtain compounds of formula (J), in which Y is -COOR, a compound of formula
    thirty
    ABOUT)
    ° A-COOMe
    five
    0
    where RI, Rz, Ra, R, RS, Re and X have the indicated meanings;
    Me, an alkali metal, alkaline earth metal, lead or silver atom, is introduced into interaction with a compound of the formula
    Hal-R. (XI) where R - has the indicated value;
    Na is a halogen atom.
    To obtain compounds of formula (I) in which Y is -COSRs, a compound of formula R.
    R
    (NI)
    0
    five
    ohhh oh
    SMe
    where RI, R2- R3, R4, Rs, Re and X have the indicated meanings;
    Me, an alkali metal, alkaline earth metal, lead or silver atom, is introduced into interaction with a compound of the formula
    Hal-Ra, (XIII) where Ra has the indicated meaning;
    Hal is a halogen atom.
    For the preparation of compounds of formula (I) in which Y is -COORy a compound of formula
    CWY;
    oh-soon
    where Ri, R2, Ra, R4, Rs, Re and X have the indicated meanings, is reacted with a compound of the formula
    HO-R, (XV) where R has the indicated value.
    For the preparation of compounds of formula (I) in which Y is -COSRe, a compound of formula
    (xv /;
    ohhhh
    SH
    where Ri, R2, Ra. R4, Rs, Re and X have the indicated meanings, are reacted with a compound of the formula
    HO-Re, (XVII) where Re has the indicated value.
    To obtain compounds of formula (I) in which Y is -COOR, a compound of formula
    where Ri, R2, Ra, R4, Rs. Re and X have the indicated meanings;
    Rx is an aliphatic, acyclic hydrocarbon residue, which is reacted with the compound
    Formulas HNRgRio, (XXI) where Rg and RIO have the indicated meanings.
    For the preparation of compounds of formula (I) in which X is —CH 2 CH 2 -. compound of formula
    (hhp)
    15
    where Ri, R2, Ra, R4, Rs. Re have the indicated meanings, are reacted with a compound of the formula
    , (XXIII) where Y has the indicated value.
    For the preparation of compounds of formula (I). in which Y is, under certain conditions, a substituted oxazolin-2-yl residue, soy
    R
    0-XC 0
    OR 7
    where Ri, R2. Ra, R4, Rs, Re and X have the indicated
    for meaning and Ry has indicated for Ry
    value,
    interact with the compound
    formulas
    HO-R7, (XVIII)
    where Ry has the meaning indicated for Ry and is not identical to Ry.
    For the preparation of compounds of formula (I) in which Y is -COSRe, a compound of formula
    R, T N R "Oh-oh-oh
    i
    SR8
    where Ri, R2. Ra, R4, Rs, Re, and X have the indicated meanings;
    Re has the meaning indicated for Re in formula (I),
    introduced into interaction with the compound of the formula
    HSRe (XIX)
    where Re has the value specified for Re in formula (I) and is not identical to Re
    For the preparation of compounds of formula (I) in which Y is -CONRgRio, a compound of formula
    RO
    G. J
    (ft)
    25 dinene formula
    R
    R,
    oh-oo
     mn-ch, pm
    where RI, R2, R3, R4, Rs, Re and X have the indicated meanings;
    Hal - a halogen atom, especially a chlorine or bromine atom, in the presence of an acid-binding agent is cyclized.
    In the compound of formula (III), in particular, a halogen atom or methylsulfonyloxy-phenylsulfonyloxy or p-tolylsulfonyloxy group is taken into account as the cleavage Z residues; halogen here represents fluorine, chlorine, bromine and iodine, preferably chlorine or bromine. . If in the compound of formula (II) M is hydrogen and in the compound of formula III, Z is a halogen atom, then the interaction is carried out in the presence of the usual proton acceptor. If in the compound of formula (III) Z is a halogen atom, then the addition of an insignificant amount of alkali metal iodide acts catalytically.
    In the compounds of formulas (IV), (VI), (VIII), Hal is a halogen atom, for example, fluorine, chlorine, bromine and iodine, preferably chlorine and bromine.
    If in the compounds of formulas (V) or (VII) M or M is hydrogen, the reaction is carried out in the presence of an acid-binding agent.
    As halides of the compounds (IV). (VI) and (VIII), hydrohalic acids, in particular hydrochloric and hydrohomic acids, are used.
    In the case of the preparation of compounds (XIV) and XVI), the water formed during the reaction can be removed, for example, by means of a water separator from the reaction mixture. By adding acid, a catalytic effect is achieved.
    The transesterification by addition of acid or base can be catalytically affected. The reaction is carried out in an excess of compounds of formula (XVIII) or (XIX).
    In the compounds of formula (XX), R is an alkyl residue with 1-6 carbon atoms, especially methyl or ethyl.
    The interactions are more advantageously carried out in the presence of solvents which are inert with respect to the reaction components. Hydrocarbons are used as inert solvents, for example, benzene, toluene, xylene, petroleum ether or cyclohexane, ethers, for example diethyl ether, tetrahydrofuran, dioxane, dimethoxyethane or diethylene glycol-dimethyl ether; acid amides, for example dimethylformamide, 2-pyrrolidinone or hexamethylphosphortriamide, or sulfoxides, for example dimethyl sulfoxide.
    As acid binding agents, for example, alkali metal and alkaline earth metal hydroxides or alkali metal or alkaline earth metal alkoxides, alkali metal carbonates or tertiary organic bases can be used.
    Reaction temperatures are generally in the range of 0-200 ° C, especially in the region of 50-150 ° C.
    The starting materials used in the compounds are known or can be prepared analogously to known methods.
    Example. 23.2 g of 8-hydroxyquinoline are dissolved in 400 ml of butanone-2 when heated and mixed in portions with 30 g of potassium carbonate. The mixture is heated under reflux for 1 h. Then, 2 g of potassium iodide is added dropwise first and then 40 g of 2-bromopropionic acid methyl ester in 100 ml of butanone-2 for 1 hour with stirring and boiling. The mixture is heated for another 10 hours under reflux. After cooling to room temperature, the mixture is poured into 1 l of water and extracted three times with 200 ml of ethyl acetate. The combined extracts are washed once with 50 ml of water, dried over sodium sulfate and filtered. The solvent is evaporated and the oily residue is triturated with
    petroleum ether is brought to crystallization. Recrystallization from hexane gives
    methyl 2- {8-quinolinoxy) -propionic acid (compound 3) in the form of beige-colored crystals, so pl. 70-72 ° C.
    Similarly to one of the methods described, it is also possible to obtain the following, listed in Table. 1 and 2, together with the compound of the example compound of formula (I).
    Comparison of the activity of the proposed antidotes with known compounds of a similar purpose against the aggressive action on cultivated plants of herbicidal pyridyloxyphenoxycarboxylic acid derivatives.
    Tested compounds: A1 herbicide
    20
    , CHS1 C1 OO-o-sn-coaxial 2S SN
    sn.
    its aggressive action on crop plants is reduced by the antidote; 25 Connection A2 for comparison:
    Compound A3: o
    J O-CH-C-N
     СН3. СЖСН
    n
    35 A4 connection:
    H
     About CH-C-NX CfVb And, ČSN -S ° N
    Compound A5:
    L
    C1
     (SNL
    five
    0
    five
    Compound A6:
     N0
    .0
    oh si
    I I s (GN. G h pz 1
    | Ј 1 W V / lU L
    C1
    connection A7:
    C1
    /
    "ABOUT
    , 0-CH-С
    ЈH XN (CVy
    n, with fci 3
    about
    Compound A8:
     h g
    .0
    C1 N CC1,
    active substances as a 10% emulsion preparation; 10% herbicide or antidote; 3% octylphenol polyethylene glycol ether (4-5 mol. AeO); 3% Ca-dodecylbenzene sulfonate; 4% glycol ether of ricin oil (35 mol. AeO); 30% cyclohexanone; 50% xylene mixture.
    Seeds are sown in plastic pots with 0.5 liters of greenhouse earth in the greenhouse. After sprouting of plants up to the stage of 2–3 leaves, the subjects were applied as an antidote of the substance together with the A1 herbicide at a consumption rate of 0.75 kg of the herbicide and 1.5 kg of the antidote per hectare. 20 days after application, the protective effect of the antidote is assessed as a percentage. Compared with plants treated with a single herbicide, as well as with a fully untreated control. The results are presented in table. 3 (herbicide: 0.75 kg / ha, antidote: 1.5 kg / ha).
    The results described show that the proposed antidotes can reduce the phototoxic effect of pyridyloxyphenoxycarboxylic acid derivatives in cultivated plants. These antidotes are significantly superior in their activity to known compounds, primarily in wheat and millet against the aggressive action of the pyridyloxyphenoxycarboxylic acid herbicide.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    Means for protecting crops from the phytotoxic effect of herbicides, including the active substance and auxiliary additives, characterized in that, in order to increase the protective effect of the pyridyloxyphenoxypropionic acid range on herbicide damages, it contains the compound of formula I as an active substance:
    Rs
    ooh
    at a) RI and H3 are chlorine and Re is hydrogen, X is CH (CH3),
    Y is methoxycarbonyl; or
    b) RI and P3 are hydrogen and Re is methyl, X is the group CHg, Y is C1-C2-alkoxycarbonyl; or
    c) RI is iodine, P3 is chlorine and Re is hydrogen, and X is the CH2 group, Y is C1 C4 alkoxycarbonyl, dicyloxycarbonyl, benzyloxycarbonyl. chloroethoxycarbonyl;
    d) Ri, R3, Re are hydrogen and X is a CH (CH3) group, Y is methoxycarbonyl, dimethylaminocarbonyl, M-methyl-L-hydroxyethylaminocarbonyl. benzylaminocarbonyl, butylaminocarbonyl, hydroxypropyl0
    five
    0
    five
    0
    five
    0
    five
    0
    five
    nocarbonyl, ethoxypropylaminocarbonyl, morpholinocarbonyl;
    or
    e) Ri and Re are hydrogen; each R3 is hydrogen, chlorine. X is C (CH3) 2 group; Y is ethoxycarbonyl;
    or
    e) RI, RS, Re is hydrogen and X is a -CH2 group, Y is carboxyl, sodium or potassium carboxylate, three (C1-C2-alkyl) -ammonium carboxylate, tri- (hydroxyethyl) ammoniumcarboxylate, alkoxycarbonyl, tetrahydrofuranyl-methoxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, chloroethoxycarbonyl,
    C1 C2-alkoxyethoxycarbonyl-dimethyl-aminocarbonyl, ethylaminocarbonyl, butylaminocarbonyl, dodecylaminocarbonyl, cyclohexylaminocarbonyl, hydroxypropylaminocarbonyl, M-methylhydroxyethylaminocarbonyl, diethylaminoethylaminocarbonyl,
    M, M-bis- (hydroxyethyl) -aminocarbonyl,
    dimethylaminopropylaminocarbonyl, N-methylbutylaminocarbonyl, dibutylsminocarbonyl, tetsyhliches, atsychystroxypropylaminocarbonyl, hydroxyethylaminoethylaminocarbonyl, allylaminocarbonyl, S, I-bis- (hydroxyethyl) -aminopropylaminocarboxylic, and aylaminocarbonyl or
    g) Ri and Re are hydrogen, RS is chlorine, X and Y together are tetrahydrofuran-2-OH-5-yl;
    or
    s) Ri and Re-hydrogen, Ry-chloro, X - CH2 group, Y - carboxyl, sodium carboxylate, potassium, ammonium, tri- (hydroxyethyl) -immonium carboxylate, C1-C12-alkoxycarbonyl. C1-C2-alkoxyethoxycarbonyl, phenoxy-to-toxycarbonyl,
    benzyloxycarbonyl alcohol contains octylphenol polyethylene glycol
    ether, calcium dodecylbenzenesulfonate, polyoxyethylated castor oil, cyclohexanone and xylene in the following ratio, wt.% Active substance10
    Octylphenol polyethylene glycol ether3 Calcium dodecylbenzenesulfonate 3
    Polyoxyethylated castor oil
    82
    -SNG86
    TIN
    -sn,
    NII
    IIIIH
    TIN
    -snsn, -snSn3
    cn cn
    Cyclohexanone Xylene
    30 50
    Table 1
    -CON
    sn2nnon
    - coax
    I I V
    ONlKCIlj), C1C. Hgo
    -with me
    -CON
    41U
    M.p. 146-149 ° C
    M.p. 73-76 ° C m.p. 120-121 ° C
    M.p. 105-111 ° С
    izi: ii: i :: i
    Continued table. one
    406
    - SI,
    M.p. 109-110 ° c
    17165880718
    Continued tlbp.1
    T a
    blitz 2.
    Continuation of table.3 f
    50
    sn
    12.5
    38
    25
    38
    25
    25
    25 38 .50 38 25 50 63 38 38 50 25 25 38
    63
    63
    50
    38
    38
    25
    25
    38
    12.5
    38
    38 38 38 25 25 38 50 50
    behind
    25 38
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    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH284182|1982-05-07|LV930556A| LV5154A3|1982-05-07|1993-06-11|A means of protecting crops against phytotoxic effects of herbicides|
    LTRP1335A| LT2617B|1982-05-07|1993-09-30|PREPARATION OF THE INFLUENCE OF HERBICIDE WITH FULL CULTURAL PROTECTION|
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