• 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:
    A herbicidal composition which comprises an adjuvant and an active ingredient of heterocyclic ether type phenoxy fatty acid derivative having the formula <IMAGE> (I) wherein A represents -CH- or -N-; X represents a halogen atom; n is 0, 1 or 2; R1 represents a hydrogen atom; a lower alkyl group; R2 represents -OH; -O-alkyl group; -OM group (M is an inorganic or organic salt moiety); <IMAGE> -O-lower alkenyl group; -O-benzyl group; -O-lower alkylalkoxy group; -O-phenyl; -O-cyclohexyl, -O-halogenoalkyl, -O-lower alkynyl and -O-cyanoalkyl; R3 and R4 respectively represent a hydrogen atom or a lower alkyl group.
    公开号:SU1452455A3
    申请号:SU802883702
    申请日:1980-02-21
    公开日:1989-01-15
    发明作者:Ура Ясуказу；Саката Гозио；Макино Кензи；Кавамура Ясуо；Кавамура Юзи；Икаи Такаси；Огути Тосихико
    申请人:Ниссан Кемикал Индастриз Лтд (Фирма)；
    IPC主号:
    专利说明:

     C (X) CH-C-A CH-C (ClOCHR C (0) (; H) K
    I with
    (I)
    ABOUT)
    where a is —CH — or —N—; X - hydrogen, fluorine, chlorine, bromine; Y is hydrogen, R is a dimethylamino group, a GR group in which R means hydrogen, C, kil, cyanomethyl, 2-chloroethyl, R. is methyl or the D-enantiomer of the active substance of general formula G in which A is —CH — or -N-; X - hydrogen or fluorine; R - gtstsroksil or methyloxy, with the following content of ingredients of the composition, wt.%: -Active substance 10-60; carrier 34-74, surfactant 2-23; 2) emulsifiable concentrate containing carrier, surfactant and active substance derived
    , aryloxyalkanecarboxylic acid. General formula (1), where A is —CH — or: —N—; X - hydrogen, fluorine, chlorine, bromine, iodine; W-- hydrogen or chlorine; R OR, where R is alkyl., Benzyl, phenyl, cyclohexyl, 2-methoxyethyl 1, allyl, propargyl; R is hydrogen or methyl, with the proviso that Y is chlorine, if X is chlorine, R is hydrogen, if A is -CH-, X and Y are hydrogen, and R is methyl; or D - znantiomer of the active substance of the general formula T, in which A is N, X is chlorine or fluorine; Y is hydrogen, C -C-alkyl, R is methyl. 4 s. and 1 z. p. f-ly, 7 tab.
    four
    after that
    4 SP
    cl

    cm
    This invention relates to chemical plant protection agents, namely, herbicidal compositions.
    The aim of the invention is to increase the herbicidal activity of a composition containing an aryloxy-alkanecarboxylic acid derivative as an active substance.
    Example. Methyl (2-quinolyloxy) phenoxy propionate (compound No. 2).
    12 g of monobenzyl simple are dissolved in 50 ml of dimethyl sulfoxide
    14524552
    distillation yields 2.2 g (yield 6S% of theor.) of the desired product. , EXAMPLE 2. 2 - (: 4- (2-Quinolyloxy) phenoxy propionic acid H, N- dimethylamide (compound No. 6).
    In 100 ml of methyl ethyl ketone, 2.3 g of the intermediate product obtained in accordance with the primacy of 1, 2- (4-hydroxyphenoxy) quinoline, 1.3 g of S, K-dimethyl-amido-6-bromopropionic acid and 1, are added. 4 g of potassium carbonate. The mixture thus obtained is subjected to refluxing for
    n „..-.-. v-j. fj I 1 dn Miu a 1 shChNS
    ether of gtsrokhinona ,. 8.2 g of 2-chloroquino-fj 5 h. After the end of the reaction, the precipitate GTT. And OT1, .. - eG.
    lina and 8.3 g of potassium carbonate. The mixture thus obtained is heated.
    The precipitated crystals are separated by filtration and the product is dried under reduced pressure, -7 ohm pressure. The resultant reaction to these substances. The crystalline product is then subjected to cooling. The reaction mixture is v-20. Recrystallization from solvent
    In the EYu-T H RonV nnnrrxri -Ti,,.
    up to 150-160 seconds for 4 hours to
    The product is extracted into water, the product is extracted several times with ether, the resulting ether layer is washed with an aqueous solution of sodium hydroxide with water, and then the ether layer is dried with sodium sulfate. The solvent is separated by distillation. The resulting crystalline intermediate is washed with diisopropyl ether to give 12 g of 2- (4-benzyloxyphenoxy) quinoline. The entire amount of intermediate was dissolved in 200 ml of a mixed solvent consisting of tetragvdrofuran and ethanol 5: 1, and 1.5 g of catalyst (palladium on activated carbon) was added. Thereafter, 880 ml of hydrogen gas is introduced into the mixture in order to carry out a hydrogenation reaction at atmospheric pressure. After hydrogenation, the catalyst is separated by filtration and suction, the solvent is separated by distillation, and the resulting residue is washed with a solvent consisting of chloroform and norms, hexane, to obtain 6.3 g of a white crystalline product of 2- (4-hydroxyphenoxy) quinoline, so pl. .
    2.37 g of the product obtained, 2.1 g of methyl 6-bromopropionate and 2.0 g of potassium carbonate are added to 50 ml of methyl ethyl ketone. The mixture thus obtained is boiled for 5 hours. After cooling to room temperature, the precipitated product is separated by filtration, the solvent is separated.
    25
    thirty
    consisting of methanol and water, with a gain of 3.6 g (approximately 88% of theor.) white crystalline target product.
    Froze Ethyl (2-hinoke-alyloxy) phenoxy propionate (compound No. 10).
    To 50 ml of acetonitrile, 2.1 g of ethyl 2- (4-hydroxyphenoxy) propionate and 1.66 g of potassium carbonate are added. The mixture thus obtained was subjected to refluxing for 1 h, then 1.65 g of 2-chloroquinoxaline was added and the mixture thus obtained was subjected to refluxing for an additional 30 hours. After cooling, the precipitated inorganic salt was separated by php. Acetone is separated from the filtrate by distillation under reduced pressure to obtain 3.5 g of an oily residue. This residue was purified by chromatography on a column filled with silica gel (chloroform was used as the developing solvent), to give 2.6 g (yield 77% of theory) of the desired product.
    EXAMPLE 4 (2-Hinoxal-1-hydroxy) phenoxy} propionic acid (compound No. 8).
    In 10 ml of ethanol, 1.7 g of ester prepared in Example 3 and 5 ml of an aqueous solution containing 0.3 g of sodium hydroxide are added. The mixture thus obtained is refluxed for 1 hour. After completion of the reaction, ethanol is separated by distillation, the remaining aqueous solution is oxidized with sulfuric acid.
    35
    40
    45
    50
    552
    distillation yields 2.2 g (yield 6S% of theor.) of the desired product. , EXAMPLE 2. 2 - (: 4- (2-Quinolyloxy) phenoxy propionic acid H, N- dimethylamide (compound No. 6).
    2.3 g of the intermediate product obtained in accordance with Example 1, 2- (4-hydroxyphenoxy) quinoline, 1.3 g of S, K-dimethyl-amido-6-bromopropionic acid and 1.4 are added to 100 ml of methyl ethyl ketone. g potassium carbonate. The mixture thus obtained is subjected to refluxing for
    n „- .-. v-j. fj I 1 dn Miu a 1 shChNS
    5 hours. After the end of the reaction,
    25
    0
    consisting of methanol and water, with a gain of 3.6 g (approximately 88% of theor.) white crystalline target product.
    Froze Ethyl (2-hinoke-alyloxy) phenoxy propionate (compound No. 10).
    To 50 ml of acetonitrile, 2.1 g of ethyl 2- (4-hydroxyphenoxy) propionate and 1.66 g of potassium carbonate are added. The mixture thus obtained was subjected to refluxing for 1 h, then 1.65 g of 2-chloroquinoxaline was added and the mixture thus obtained was subjected to refluxing for an additional 30 hours. After cooling, the precipitated inorganic salt was separated by php. Acetone is separated from the filtrate by distillation under reduced pressure to obtain 3.5 g of an oily residue. This residue was purified by chromatography on a column filled with silica gel (chloroform was used as the developing solvent), to give 2.6 g (yield 77% of theory) of the desired product.
    EXAMPLE 4 (2-Hinoxal-1-hydroxy) phenoxy} propionic acid (compound No. 8).
    In 10 ml of ethanol, 1.7 g of ester prepared in Example 3 and 5 ml of an aqueous solution containing 0.3 g of sodium hydroxide are added. The mixture thus obtained is refluxed for 1 hour. After completion of the reaction, ethanol is separated by distillation, the remaining aqueous solution is oxidized with sulfuric acid.
    five
    0
    five
    0
    3.1452455
    acids and precipitated crystals. The conditions of examples 1-4 are obtained.
    the lytic product is separated by filtration — and other compounds represented by
    her, washed with water and dried to obtain tab. 1. 1.3 g (yield 84% of theory) of a white crystalline target product.
    Table 1 Active substances of general formula
    ethyloxy
    85N 6-Fluorine Propargyloxy
    86N 6-Fluoride cyanomethyloxy
    87N 6-Chloromethane
    A note is methyl, except for compound # 7, where Ri is hydrogen. 5 pounds per million (CDC1,): 1.2 (ZN, t); 1.6 (3N, d);
    4.15 (2H, q); 4.65 (1H, q); 6.75-8.05 (UN, t) 0h. per million (CDCI,): 3.75 (ZN, S); 4.55 (2H, S); 6.7-8.1 (UN, t).

    D-isomers of compounds nos. 2, 9, 14, 22, 25, .26.
    Specific forms of the herbal composition are presented in Table. 2-5.
    Wettable powder
    qi (7)
    10 8 30 Calcium carbonate (63), Sorpol 5039 (5), Runox
    1000-Ce (2)
    141240 Kaolinite (54), Sorpol 5039 (4),; 1 Signesulfonate
    rub (2)
    1513 20 Zeklit Pi-Ef-Pi (74), Sorpol 5050 (4), yox
    1000-Ce (2)
    27 25 35 Zeeklit Phi-Phi (57), Karplex N 80 (1),
    Sorpol 005D (4), sodium ligninsulfonate (3)
    2927 40 Talc (54), Sorpol 5050 (3), Runox 1000-Ce (3)
    3028 45 Zeklit Pi-Ef-Pi (48), Karplex 80 (1), Sorpol
    5029-0 (4), calcium ligninsulfonate (2)
    1.5731
    110-111
    116-118
    Table 2
    (30), Sorpol 3005 (10)
    2680 (8)
    Polyoxyethylene styrylphenyl ether (31) + nonylphenol (ethylene ethoxy 2 mol) (31%) Calcium dodecylbenzenesulfonate (38%)
    Continued table. 3
    Suspension concentrate
    18
    23
    28
    31
    41
    45
    47
    49
    58
    sixteen
    21
    26
    29
    39
    43
    45
    47
    56
    50
    20
    thirty
    ten
    15
    15
    35
    25
    Soprophore Ef-El (3), Antiform Ar-D (0.5), eti-, lenglikol (10), xanthan gum (0.15), formalin (0.25), water (36.1)
    Propylene glycol (20), carboxymethylcellulose (3), sodium ligninsulfonate (2), water (55)
    Propylene glycol (15), polyvinyl alcohol (2), water (33), Agrisol S-710 (7), sodium ligninsulfonate (13)
    Ethylene glycol (15), sodium alginate (4), formalin (0.3), Runex iOOO-Ce (5), Nippol (15), water (50.7)
    Ethylene glycol (15), xanthan gum (0,2), formalin (0,3), Nippol (20), water (54,5)
    Ethylene glycol (10), xanthan gum (0.3), formalin (0.2), sodium ligninsulfonate (6), Agrisol S-710 (3), water (65.5)
    Ethylene glycol (10), polyvinyl alcohol (3), water (63), calcium ligninsulfonate (6), Agrisol S-710 (3)
    Propylene glycol (15), xanthan gum (0.3), formalin (0.2), Agrisol S-710 (10), water (charger, 5)
    Ethylene glycol (15), sodium alginate (3), sodium ligninsulfonate (8), Agrisol S-710 (4), water (45)
    59
    57 35 Propylene glycol (l5), xanthan gum (0.3),
    60
    58
    45
    formalin (0,2), Agrisol ES-710 (15), water (34,5)
    Propylene glycol (15), xanthan gum (0.5), formalin (0.5), sodium ligninsulfonate (9), Agrisol S-710 (5), water (25)
    Eziin
    one
    67
    2 65
    3 20
    Ethylene glycol (15), sodium alginate (3), sodium ligninsulfonate (9), Agrisol S-710 (5), water (48)
    6866 30 Ethylene glycol (15), carboxymethylcellulose (3),
    Runox 1000-Tse (2), Nippol (4), water (46)
    6967 40 Ethylene glycol (15), polyvinyl alcohol (3),
    Soprofor Ef-El (7), water (35)
    73 71 50 Ethylene glycol (10), carboxymethylcellulose (3),
    Runox 1000-Tse (2), Nippol (4), water (31)
    8381 30 Propylene glycol (10), polyvinyl alcohol (3),
    water (48), calcium ligninsulfonate (6), Agrisol S-710 (3)
    8482 35 Ethylene glycol (15), sodium alginate, (3), water
    (38) ,, Runox 1000-Ce (3), Nippol (6)
    89 87 15 Ethylene glycol (15), xanthan gum (0.3),
    formalin (0,2), Soprofora Ef-El (9,5), water (60)
    9223 10 Ethylene glycol (13), xanthan gum (0.23),
    formalin (0.23), Agrisol ES-710 (1.5), Nippol (21), water (54.04)
    9323 50 Ethylene glycol (10), xanthan gum (0.15),
    formalin (0,25), Soprophore Ef-El (3), Antiform Ar-Di (0.5), water (36.1)
    Table 5
    23
    no components in the table. 2-5. Bela Soot - Silica Powder
    Polyoxyethylene alkylaryl
    50% sulphate ester, dioxvide silicon hydrate 50%
    Dioctitol Sulfo Amber
    acid, sodium salt
    50% white carbon black silica powder 50%
    Sodium Salt Lauric Acid 90% Sulfate
    rub 10%
    Polyoxyethylene nonylphenyl ether 50%, white carbon black - silicon dioxide 50%
    Naphthyl methane sulfonate sodium
    Polyoxyethylene formyl nonyl ether 50%, polyoxyethylene nonylphenol ether 20%, polyoxyethyl sorbitan lauric acid ester 10%, dodecyl benzene sulfonate 20%
    Polyoxyethylene ester with castor oil 11%, polyoxyethylene alkylphenyl ether, polymer 26%, dobecylbenzenesulfonate 33%, xylene 30%
    Polyoxyethylene styrylphenyl ether 7%, polyoxyethylene styrylphenyl ether 43%, calcium dodecyl benaenesulfonate 30%, xylene 20%
    Polyoxyethylene nonylphenyl ether 10%, polyoxy ethylether n-t t yrylphene Sh10B ether 10%, ethylene oxide block copolymer and propylene

    1A52L5524
    Continuation of table.5
    Nippol 15
    Soprofor Ef-El
    20 Sorpol W-i50
    25
    Sorbon Ti-20
    Sorbon Ti 80
    oxide 60%, isobutyl alcohol 20%
    Polyoxyethylene octylphenyl ether
    Polyethylene with ethylene-polyarylphenol phosphate, triethanolamine salt
    Polyoxyethylene nonylphenyl ether.
    Polyoxyethylene sorbitan monolaurate (20 mol of ethylene oxide)
    Polyoxyethylene sorbitan monolaurate (ethylene oxide 80 mol)
    Antiform of Silicon Emulsion 30 Ar-Dee
    Zeklit Pi-Ef-Pi contains,%: SiQ.,. 67-70; A12.0-, 18-20; less than 0.4; CaO less than 1.8; MgO less than 1.8; less than 0.05; CgO less than 5.5; loss during combustion 4.5-5.5.
    Heyklit contains;%: SiO 56-58; , 26-28; less than 0.5; CaO less than 2.0; MgO less than 2.0; Na.j, 0 less than 0.05; less than 6.5; loss on combustion 6.0-7.0.
    Shelsol AB-trimethylbenzene with so kip. 187-201 ° C.
    Determination of herbicidal action in tillage (pre-emergence 5 application).
    Special plastic boxes fill the prepared sterilized diluvial soil and plant seeds of experimental plants to a depth of 1.5 cm. The soil is treated with an appropriate form of the herbicidal composition diluted with the required amount of water at a dose of 2.5 kg / ha.
    The assessment of the herbicidal effect is carried out 5 tons after three weeks after tillage on the following rating scale: Score Suppressed plant growth,% 590-100
    35
    40
    0
    0
    Note: Under the influence of the proposed substances on marh, purslane, galinsogu, yellow cress, there is no herbicidal effect. The exception is compound no. 4 (herbalized action 5 points).
    Determination of herbicidal activity in the treatment of leaves (post-emergence application).
    The seeds of the experimental plants are sown in special vessels filled with soil, plants are grown to a stage of 2-3 leaves and treated with their appropriate forms of the herbicidal composition diluted with the required amount of water at a dose of 2.5 kg / ha.
     The evaluation of the herbicidal action was carried out two weeks after the treatment according to the rating scale presented above. The results of the experiments are presented in table 0. 7
    Table 7 Herbicidal activity during processing
    leaves
    five
    5 5 5 5 5
    5 2
    five
    five
    four
    five
    five
    3
    5 5 4 5 5
    4 2
    5 3 3 5
    4 5
    31 Continued table. 7
    -u-t
    Note.: Under the influence of the proposed compounds on march, purslane, galinsogu, yellow cress, tomatoes, there is no herbicidal effect. The exception is compound no. 4 (herbalized action 5 points).
    The known compound dichlofop-methyl acts on plants as follows, a score: Figure 1; Elefsina 3; Mar 1; purslane 1; Galinsog 0; yellow cress 1; tomatoes 0.
    The results of the experiments indicate a significantly greater efficacy of the herbicidal composition according to the invention as compared with the known herbicomide dichlofop-methyl.
    权利要求:
    Claims (3)
    [1]
    Invention Formula
    1. A herbicidal composition in the form of a wettable powder, containing the active substance - arst-oxyalkanoic acid derivative, carrier and surfactant, characterized in that, in order to enhance the herbicidal activity, it contains the active substance of the general formula 1
    where a CH- or -N-;
    X - hydrogen, fluorine, chlorine, bromine;
    R is a dimethylamino group or a group OR, where R is hydrogen, C, -C4-alkyl, cyanomethyl, 2-chloroethyl, or the D-enantiomer of the active substance
    1452455
    32
    ten
    15
    General formula 1, where a is —CH — or —N—; X is hydrogen or fluorine; R is hydroxyl or methyloxy; a carrier selected from the group of diatomaceous earth, kaolinite, cerisite, cream dioxide, aluminum oxide, talc, calcium carbonate, or a combination thereof; a surfactant selected from the group of calcium ligninsulfonate uu, sodium ligninsulfonate, poly-oxyethylene alkylaryl ether sulfate hydrate dioks1scha silica, sodium Salts of dioctylsulphosuccinic acid, silica, sodium lauryl sulphate, sodium polioksietilennonilfenilovo- of ester naphthylmethanesulfonate or a combination thereof, with the following content of 20 research institutes of the ingredients of the composition, wt.%: Active substance 10-60
    Carrier 34-74
    Surfactant2-23 25
    2. The herbicidal composition in the form of an emulsifying concentrate, containing the active substance — an aryloxyalkanoic acid derivative, a carrier and a surfactant;
    [2]
    the fact that, in order to enhance the herbicidal activity, it contains an active substance of the general formula
    R
    / 7 0- (O) -OCH-CQOR,
    where a CH- or -N-;
    X is hydrogen, fluorine, chlorine, bromine, 0 iodine;
    Y is hydrogen or chlorine;
    K-4 C (-Su-alkyl benzyl, phenyl, cyclohexyl, 2-methoxyethyl, allyl, propargyl;
    5 2. hydrogen or methyl, with the proviso that Y is chlorine; if X is chlorine ,. R is hydrogen, if A is —CH—, X and Y are hydrogen, R is methyl.
    five
    0
    or the D-enantiomer of the active substance of the general formula 11, where A is N, X is chlorine or fluorine; Y is hydrogen; R, - C, -C4-alkyl; R is methyl; media selected from the group of xylene, methyl-5 naphthalene, phenol, cyclohexanone, acetophenone, isophorone, dimethylformamide, orthochlorotoluene, anisole, morpholine, orthodichlorobenzene, 1,4-dioxane, N-methylpyrrolidone, tri33
    methylbenzene or a combination thereof; a surfactant selected from the group of calcium dodecylbenzenesulfonate, polyoxyethylene formyl nonyl ester, polyoxyethylene nonylphenyl ester, polyoxyethylene sorbitan lauric acid ester, polyoxyethylene ester; Lena and Castor oil, Polymer polyoxyethylene alkylphenyl ether, Xylene, Polyoxyethylene styrene polyphenyl ether, Polyoxy ethylene styryl phenyl ether, Polyoxyethylene alkylate ether polyether sulfate, polyhydroxyethylene, polyhydroxyethylene, polyoxyethylene ethylenyl ether .%:
    Active Substance5-40
    Carrier48-90
    Surfactant5-32
    3. A herbicidal composition in the form of a solution, containing the active substance, an aryloxyalkanoic acid derivative, carrier and surfactant, characterized in that, in order to enhance the herbicidal activity, it contains the active substance of the general formula 111
    [3]
    where a is —CH — or —N—;
    X - hydrogen, fluorine, chlorine, bromine;
    Z is a sodium, ammonium, substituted ammonium cation, the carrier is water and a surfactant selected from the group of 45 sodium alginate or a combination thereof.
    lyoxyethylene nonylphenyl ether, polyoxyethylene sorbitan monolaurate, polyoxyethylene octylphenyl ether or a combination thereof, with the following content of ingredients of the composition, wt%:
    Active Substance8-30 Surfactant5-30 Water 60-85 4, Herbicidal composition in suspension suspension form, containing active substance - derivative
    245534
    aryloxyalkanecarboxylic acid, surfactant, carrier, antifreeze and thickener, characterized in that, in order to enhance the herbicidal activity, it contains a common active ingredient. Formula IV
    BUT
    about;;;
    N
    ten
    Where
    A - -CH- or -N-; X - hydrogen, fluorine.
    chlorine, bromine.
    iodine;
    OR where
    Y is hydrogen, chlorine; R is a dimethylamino group or a group is hydrogen, C -Cj-alkyl,
    cyanomethyl, 2-methoxyethyl, benzyl, allyl, provided that X is chlorine, when Y is chlorine, or the D-enantiomer of the active substance of general formula IV, where A is —CH — or
    -N-; X is hydrogen or fluorine; Y is hydrogen; R is methyloxy, provided that X is hydrogen, when A is -N-; X - fluorine, when A - -CH-; surfactant selected from the group of polyoxyethylenenonyl-. phenyl ether, polyoxyethylene
    the carrier is water; antifreeze selected from the group of ethylene glycol and propylene glycol; thickener selected from the group of xanthan gum, carboxy methylcellulose, polyvinyl alcohol
    with the following content of ingredients of the composition, wt.%:
    Active substance 10-50
    Surfactant 3,0-22,5
    Antifreeze10-20
    Thickener 0.15-4.00
    WaterEverything
    5. The herbicidal composition according to claim 4, characterized in that it contains an antifoaming agent — a silicone emulsion in an amount of 0.5% by weight and / or a preservative — formalin in an amount of 0.2-0.5% by weight.
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    同族专利:
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    GB2126580A|1984-03-28|
    ES8103044A1|1981-02-16|
    FR2449683B1|1983-09-16|
    CA1306259C|1992-08-11|
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    PL128652B1|1984-02-29|
    FR2449683A1|1980-09-19|
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    PL222116A1|1981-04-24|
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    CH647510A5|1985-01-31|
    JPS6033389B2|1985-08-02|
    ATA93280A|1981-06-15|
    NL185280B|1989-10-02|
    IL59281A|1985-02-28|
    NL8000888A|1980-08-26|
    BR8001061A|1980-11-04|
    GB2042539A|1980-09-24|
    GB2126580B|1984-08-30|
    CA1304377C|1992-06-30|
    AU5572980A|1980-08-28|
    CS226009B2|1984-03-19|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP54020164A|JPS6033389B2|1979-02-22|1979-02-22|
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