• 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:
    Use as fungicides of N-(3-pyridylmethyl)-N-acyl anilines, of the formula <IMAGE> wherein the symbols have assigned meanings.
    公开号:SU1186073A3
    申请号:SU2950207
    申请日:1980-07-16
    公开日:1985-10-15
    发明作者:Тен Хейкен Питер；Беатрис Вебб Ширли
    申请人:Шелл Интернэшл Рисерч Маатсхаппий Б.В. (Фирма)；
    IPC主号:
    专利说明:

    00 O5 Od 1 The invention relates to agriculture, namely to a method for regulating plant growth using chemical compounds. The purpose of the invention is to increase the growth regulating activity. Example 1. A method for producing N-tret-butylcarbonyl-N (4-chlorophenyl methyl) aminopyrazine — Compound A). To formic acid (98%, 10.8 g) is added to a suspension of 4-chloro- (pyrazini minomethyl) benzene (21.75 g, 0.1 mo in dry toluene (50 ml)) and the mixture is stirred and heated refluxing for 16 hours. Toluene and mu1) avianic acid is distilled off in vacuo, to the remaining stripping product is added 10% IC1 (100 ml). The mixture is extracted with 10 ml of toluene, the aqueous layer is separated and alkalinized with a concentrated aqueous solution of KOH. The product is extracted with diethyl ether and the extracts are dried with MgSO4. After distilling off the solids, the product is purified by passing it through a chromatographic column (neutral alumina / diethyl ether). Pure N- (4-chlorophenylmethyl) -aminopyrazine is obtained with a code of 27% in the form of a besttvetny substance with m.p. 86-87 C. as read,%: C 60.14; H 4.56; N 19.13i C1 16.17. ,, H,
    Table 1 3 Found,%: C 60.4J H 4.8; N 19.2; C1 16.0 N B) To a solution of M- (4-chlorophenylmethyl) aminopyrazine (2.2 g, 0.01 mol) in anhydrous benzene (30 ml) was added a solution of trimethylacetyl chloride (1.4 g, 0.012 mol) in anhydrous benzene (10 ml), followed by the addition of a solution of dehydrated triethylamine (1.3 g, 0.013 mol) in dehydrated benzene (10 ml). The mixture was stirred and heated to reflux for 22 hours. After cooling, the reaction mixture was washed three times with water and dried with MgSQ. The solvent is distilled off in vacuo, the remaining Stripping product is subjected to chromatographic separation in a column filled with neutral alumina, and by aluminizing with diethyl ether / hexane in a ratio of 3: 1. As a result, N-tert-butylcarbonyl-M- (4-chlorophenylmethyl) -aminopyrazine is obtained with a yield of 58% as a colorless solid, mp 65-68 ° C. Calculated,%: C 63.26; H 5.93; N 13.84. NgClC, gH, 8 Found,%: C 63.3 | H 5.9; N 13.9. Carrying out the processes of Example 1j, compounds 2-15 are obtained. The physicochemical properties of compounds 2-14 derived from aminopyrazine are listed in Table. one.
    2 tert-butyl
    4-fluorine
    3-CH-tert-butyl
    4-chloro
    4 - about SI,
    14.6
    41-42
    53/55
    Oil Example 2. The effect of compound 1 on the GROWTH of various herbs is compared with that of maleic hydrazide.
    Continued table. 1 acid. Herbs bonfire barren (BB), six-sided Bukharnik (PP), tall oats (TF), fenders
    common (BT) and rye grassland (LP). divisible P e in plastic fittings. The sod is cut, which is cut, and the herbs are pealed at the peak of the tick before it is processed. A drug
    Hydrazide MaleiBOBOfi Acid
    Complete destruction of all treated plants;
    A visual assessment of the appearance of the. Kernel was carried out 25 days after processing on a linear scale in units of 0-9: O - good sod appearance, 9 - unacceptable appearance. These results translate into percentages of the control, results exceeding 100% show that the treated plants have a more attractive appearance than the untreated control plants. .
    : It has been established that compound 1 gives the most attractive dark green grass cover. In contrast, maleic hydrazide gives rise to symptoms of chlorosis and necrosis, which weaken the plants. Table. 2 show that Compound 1 is more effective than maleic hydrazide.
    Connection 123456 Action .7645465
    For comparison, the test was carried out under identical conditions, but with ispol. by identifying a technically available plant growth regulator A (mericchloride or M, N-dimethylpiperidinium chloride), for which the absence of any activity is observed at a dosage of 1 kg / ha. C used was applied to test plants at doses of 1.0, 2.5 and 5.0 kg / ha.
    The test results are shown in Table. 2
    Table 2
    PRI me 3. Conduct a series of tests by spraying the leaves in which the soybean seedlings are treated with compositions containing the test compound.
    The compositions are prepared by diluting with water solutions of the test compounds in acetone, which contains 0.4% by weight of surfactant. Acetone solutions are diluted with equal volumes of water and treated at a dose of the active compound of 1.0 kg / ha.
    Evaluation of the effect of regulating plant growth was performed on the eleventh day after spraying. The results are shown
    45 below (O indicates growth of untreated, control plants, and 7 is the maximum growth retardant effect).
    7 8 9 10 11 12 13 14 15 A
    51545534О
    By such a compound, the effect of controlling plant growth (score 4) is observed only when the dosage is increased to 5 kg / ha. 55 Example4. Experiments with increased tillering of wheat.
    Wheat wheat plants are grown in 7-centimeter pots in
    greenhouse conditions at 20 ° C and a duration of 16 hours a day,
    When the first shoots appear (after 21. day after sowing), the soil is treated with solutions of Compound 1 as a 2% aqueous plant. a thief of acetone in amounts equivalent to the dosage of 0.01 - 3.0 kg / ha
    In the course of control experiments. The soil is treated at a rate of 10 15 MP each with a 2% aqueous solution of acetone.
    After 29 days after treatment, the number of visible, shoots in both treated and 5 untreated plants is counted.
    The data in the tables below correspond to the average number of visible shoots for 10 pots used during each 20 processing experiments.
    The effect of compound 1 on tillering of wheat (see Table 3).
    Table
    % of control plants 21 days after treatment
    114.43 174.13
    Continued table. 3
    With the help of a winter cultivator, barley was processed in two experiments (A and B) at the late tiller stage with a compound .1. Harvest harvest compare the vals with the crop of the untreated control. The results are shown in Table. four.
    | T a b and c a 4
    Effect of compound 1 on barley harvest
    The results indicate the use of the compound contributes to increasing the yield of winter barley.
    权利要求:
    Claims (1)
    [1]
    METHOD FOR REGULATING PLANT GROWTH, including treating plants with an active compound, characterized in that, in order to increase the growth regulating activity, an aminopyrazine derivative of the general formula is used as an active compound: where R is an alkyl group C f - C 6 ;
    X is a fluorine atom with η = 0-1 or a chlorine atom with η = 0t2, and the treatment is carried out at a dose of the active compound of 0.1-5 kg / ha.
    类似技术:
    公开号 | 公开日 | 专利标题
    SU1186073A3|1985-10-15|Method of regulating growth of plants
    DD273768A5|1989-11-29|PLANT GROWTH REGULATOR COMPOSITION
    US4075000A|1978-02-21|Herbicidal use of 4-amino-3,3-dimethyl-1-phenyl-2-azetidinones
    US3175897A|1965-03-30|Asymmetric thiolcarbamates as herbicides
    DE2548231A1|1976-05-06|1- | -2-OXOPYRROLIDINE-4-CARBONIC ACID DERIVATIVES, THEIR PRODUCTION AND USE AS PLANT GROWTH REGULATORS AND HERBICIDES
    US4092432A|1978-05-30|Mixtures having antimicrobial or pesticidal effect
    EP0269656B1|1993-12-29|Novel malonic acid derivative compounds and compositions thereof for retarding plant growth
    DE2515113C2|1989-04-27|
    US3120434A|1964-02-04|Herbicidal method employing n, n-dialkyl-diphenylacetamides
    DD149935A5|1981-08-05|PROCESS FOR THE PREPARATION OF RACEMENS OR OPTICALLY ACTIVE 2- | -1,7,7-TRIMETHYLBICYCLO | HEPTANE
    US3816092A|1974-06-11|Herbicidal 3,1-dichloroanilides
    CH628017A5|1982-02-15|METHOD FOR PRODUCING THE NEW COMPOUND N- | -N&#39;-METHYL-N&#39;-METHOXY-UREA.
    DE1493992A1|1969-05-29|Manufacture and use of herbicides
    US3318679A|1967-05-09|Process of controlling plant growth
    DE69823191T2|2004-08-19|1,2,3-THIADIAZOLE DERIVATIVES, MEANS FOR CONTROLLING PLANT DISEASES AND METHOD FOR THE USE THEREOF
    CH616687A5|1980-04-15|
    EP0019978B1|1982-11-17|Novel phenylpyrrole derivatives, process for the preparation thereof, fungicidal compositions containing them and method for controlling fungi
    DE2112643C3|1981-02-19|Formamidine derivatives and compositions containing them
    US3158624A|1964-11-24|Preparation of trichlorofuroylchloride
    US3844762A|1974-10-29|Phenylnitramine herbicides
    US3637851A|1972-01-25|N - cycloalkyl-chlorobenzylidenimines and herbicidal compositions containing same
    DE2624094A1|1976-12-02|N-CARBAMOYL-N-PHENYLAMINO ACID DERIVATIVES, METHOD FOR THEIR PRODUCTION AND HERBICIDAL AGENTS
    DE2745229C2|1986-03-27|4-Alkylsulfonyloxyphenyl-N-alkylthiocarbamates, process for their preparation and their use as fungicides
    US3266883A|1966-08-16|Herbicidal method
    US3884670A|1975-05-20|Plant growth regulators
    同族专利:
    公开号 | 公开日
    PT71564A|1980-08-01|
    AU536746B2|1984-05-24|
    CS504880A2|1989-03-14|
    TR21816A|1985-07-23|
    IL60614D0|1980-09-16|
    FR2461457B1|1984-11-16|
    ES8104990A1|1981-05-16|
    CH647649A5|1985-02-15|
    CU35278A|1982-03-28|
    IE801477L|1981-01-19|
    NO164451B|1990-07-02|
    FI802258A|1981-01-20|
    FI76792B|1988-08-31|
    FR2461457A1|1981-02-06|
    LU82630A1|1981-02-02|
    AU6044080A|1981-01-22|
    IT1132198B|1986-06-25|
    HU186300B|1985-07-29|
    DD154468A5|1982-03-24|
    IL60614A|1984-08-31|
    BR8004436A|1981-02-24|
    NO802135L|1981-01-20|
    MW2480A1|1981-12-09|
    SE452544B|1987-12-07|
    RO84716A|1984-07-17|
    BE884340A|1981-01-16|
    NL8004078A|1981-01-21|
    DK163907B|1992-04-21|
    IT8023496D0|1980-07-16|
    DK307780A|1981-01-20|
    GR69690B|1982-07-08|
    BG35181A3|1984-02-15|
    CA1231710A|1988-01-19|
    SE8005190L|1981-01-20|
    RO84716B|1984-09-30|
    JPS5616469A|1981-02-17|
    PL225696A1|1981-05-08|
    DE3026926A1|1981-04-30|
    ATA369180A|1982-07-15|
    US4441912A|1984-04-10|
    FI76792C|1988-12-12|
    NO164451C|1990-10-10|
    ZA804285B|1981-06-24|
    US4359576A|1982-11-16|
    NZ194365A|1983-03-15|
    US4358446A|1982-11-09|
    ES493416A0|1981-05-16|
    OA06692A|1982-05-31|
    CS266307B2|1989-12-13|
    DK163907C|1992-09-21|
    ZM5980A1|1981-05-21|
    IE50011B1|1986-01-22|
    AT369950B|1983-02-10|
    JPH024566B2|1990-01-29|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2731470A|1956-01-17|N-pyrtoylmethyl |
    US3055906A|1960-10-19|1962-09-25|Us Vitamin Pharm Corp|Pyridylethylated d-alpha-methylphenethylamines|
    NL6707290A|1966-05-28|1967-11-29|
    ES368093A1|1968-07-16|1971-07-16|Degussa|Benzyl amino carbamate substituted pyridines|
    US3674459A|1969-06-30|1972-07-04|Monsanto Co|Phytotoxic compositions|
    US3819661A|1971-11-01|1974-06-25|Mobil Oil Corp|2-chloro-n-furfuryl or tetrahydrofur-furylacetanilides and ring substituted derivatives|
    US3880840A|1974-02-01|1975-04-29|Hoffmann La Roche|Pyrazino-1,4-diazepines|
    US3946044A|1974-08-01|1976-03-23|Velsicol Chemical Corporation|N-alpha-chloroacetyl-n--2-ethyl-6-methylaniline|
    US3901917A|1974-11-04|1975-08-26|Velsicol Chemical Corp|N-thienylalkylacetanilides|
    US3946045A|1974-11-13|1976-03-23|Velsicol Chemical Corporation|Dioxolane substituted anilids|
    GB1533705A|1975-03-10|1978-11-29|Ici Ltd|Method of combating fungal infections in plants using imidazoles and 1,2,4-triazoles|
    US4172893A|1975-12-19|1979-10-30|Rohm And Haas Company|Rodenticidal 3-pyridylmethyl phenyl carbamate metal salt complexes|
    DD123049A1|1975-12-23|1976-11-20|
    USRE30563E|1977-07-27|1981-03-31|Eli Lilly And Company|Preparation of benzoylureas|
    DE2744396A1|1977-10-03|1979-04-12|Basf Ag|ACETANILIDE|
    ZA786052B|1977-10-26|1980-06-25|Wellcome Found|Imidazoline derivatives and their salts|
    DE2805757A1|1978-02-10|1979-08-16|Bayer Ag|N-AZOLYLALKYL HALOGEN ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES|
    US4293552A|1978-02-27|1981-10-06|Eli Lilly And Company|Novel 1--3- ureas|
    DE2832940A1|1978-07-27|1980-02-14|Basf Ag|HERBICIDAL AGENTS|US4501746A|1981-12-18|1985-02-26|Eli Lilly And Company|N,N-disubstituted carboxamide derivatives, and fungicidal use thereof|
    US4517186A|1982-09-30|1985-05-14|Merck & Co., Inc.|2-Amino-3,5-dicyano-6-pyrazine antimicrobial compounds|
    US4518599A|1982-09-30|1985-05-21|Merck & Co., Inc.|2-Amino-3-cyano-5-halo-6-pyrazine|
    US4552960A|1983-06-20|1985-11-12|Eli Lilly And Company|Fungicidal amines|
    US4571337A|1984-05-10|1986-02-18|Hunt-Wesson Foods, Inc.|Container and popcorn ingredient for microwave use|
    AT47846T|1985-06-21|1989-11-15|Ciba Geigy Ag|MICROBICIDES.|
    US4797313A|1985-11-08|1989-01-10|Monsanto Company|Non-metallic polymeric twist tie|
    US4742167A|1986-05-30|1988-05-03|The Dow Chemical Company|Biologically active N-pyrazinyl-haloacetamides|
    US5006154A|1986-07-24|1991-04-09|Shell Oil Company|Method of synchronizing flowering in plants|
    CH668969A5|1986-09-05|1989-02-15|Ciba Geigy Ag|METHOD FOR CONTROLLING UNWANTED PLANT GROWTH AND FOR REGULATING PLANT GROWTH.|
    RU2077531C1|1990-05-31|1997-04-20|Пфайзер Инк.|Method for production of substituted -2-phenyl piperidines, substituted -2-phenyl pyridine and method for its production|
    DE69128036T2|1990-08-10|1998-02-19|Reilly Ind Inc|METHOD FOR PRODUCING IMINES, ALDEHYDES AND UNSYMMETRIC SECONDARY AMINES|
    US5364943A|1991-11-27|1994-11-15|Pfizer Inc.|Preparation of substituted piperidines|
    DE69331190T2|1992-05-18|2002-04-18|Pfizer|BRIDGED AZABICYCLIC DERIVATIVES AS SUBSTANCE P ANTAGONISTS|
    AU4314693A|1992-06-02|1993-12-30|Ciba-Geigy Ag|Pyrimidinyl- and triazinyl- salicyl- and picolylamides and the use, as herbicides, and preparation thereof|
    EP0654029A1|1992-08-04|1995-05-24|Pfizer Inc.|3-benzylamino-2-phenyl-piperidine derivatives as substance p receptor antagonists|
    JP4877679B2|1999-09-03|2012-02-15|雪印種苗株式会社|Plant growth regulator|
    EP1377163B1|2001-04-11|2006-11-15|Valent Biosciences Corporation|A concentrated, water-soluble, granular plant growth regulator formulation and methods for use of same|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB7925164|1979-07-19|
    [返回顶部]