• 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:
    1. ESHAB OF OBTAINING ACYLALININES of the general formula: R - lower alkyl, Substituted by 1-4 atoms i reaioi •• -. . - dd, -. ".:. '',. Y is the lowest aksh1eH | distinguishing with the fact that the compound of the general formula '^^^ T ^ H-Y-COOKz" Nggdanizshy alkyl; Rj is hydrogen, alkyl, nyspaphenyl, lower alkyl, or cyclohexyl, where R, R.R.J and Y have the above - 1 "- ^ 2" values, are reacted with an acid halide hydride of the general formula. R ^ "^ OX, where R - is as defined above, 'X is halogen,.' '• in the presence of a dehydroaprghenic agent agent at a temperature from room temperature to the boiling point of the reaction mass in an inert organic solvent. 2. The method according to claim 1, 1 and 2, so that it is used as a dehydrohalogenating agent. triethylamine. '. (LS' • ^^^ I4D
    公开号:SU721000A1
    申请号:SU2017322
    申请日:1974-04-18
    公开日:1986-11-30
    发明作者:Акиба Кеитиро；Сатоми Такео；Фудзинами Акира；Асано Ясухиса；Камеда Нобуюки；Мине Акихико；Хино Наганори；Татейси Кохси
    申请人:Сумитомо Кемикал Компани (Фирма)；
    IPC主号:
    专利说明:

    AT /
    I:
    "- - l-yy
    -.... -J; This invention relates to a process for the preparation of HOBbnt acylanilines of the general formula. , w-sovz, where R ,, R is a lower alkyl; / Rg is hydrogen, alkyl, lower appenyl, lower quinil or cyclohexyl; R is lower aikil, substituted with 1-4 aTOMafJH halogen; Y is lower alkylene. - - The method of obtaining compounds of formula (1) is based on the known reaction a1 9 li | Oxygenated nitrogen compounds of hectares: p6-anhydrides of acids. The process is usually carried out at room or peri phenol yu {go, 111 $ only in an organic solvent medium, in the presence of dehydrogalogenizing agent. (I). The aim of the invention is the co-ordination of compounds for expanding the assortment of substances of herbicidal action. ; - ;; -. : -7 --- .-. .-Tsei is achieved by the compound of the general formula ISIH-Y-COORs R H Y HMeitfr above R, R, the indicated values are subjected to interaction by acid halide with an acid anhydride of the general formula. ;; .-; ; . where R has the above §1 data. value, X is a halogen, in the presence of an appropriate kind of carbon dioxide generating agent, usually TPJI ethyl amine, at a temperature from room temperature and a percentage of its mass in an inert organic solvent. The compounds of formula (1) have a strong herbicidal action with a broad spectrum of action, for example, they have a herbicidal effect on 02 such sorrow. As Kirovinova, foxtail articulated, one-year-old,. In addition, the proposed compounds have a selective effect on various agricultural crops, so that they are able to kill weeds without having a phytoxic effect on cultivated plants, such as radish, cabbage, peas, sugar beets, tomatoes, cotton, wheat, rye (corn) ,. The compounds of formula (I) are prepared generally as follows. . Compounds of formula (I) and equimol pH are the amount of acid halide acid of formula (IG) dissolved in an inert organic solvent, for example, benzene, toluene, xylene, ethyl ether, isopropyl ether, ligroine, hexane, acetone, methylisobutyl ketone, chloroform, uniforms, chloroform, uniforms, chloroform, acetone, chloroform, acetone, chloroform. benzene, then an equivalent amount of a dehydrohalogenating agent, such as pyridine, triztilamine, H, N-diethylaniline, N-methylmorpholine, sodium carbonate or potassium carbonate, preferably triztilamine, is added dropwise, pereme- admixture. sew for some time, the resulting solution sequentially. washing | diluted with hydrochloric acid, diluted with an aqueous solution of alkali, then with water and after drying the solvent is distilled off. Get a clean target product with a good yield. :. ;: -:;,. {. . The proposed SoEdNeny can be applied as such or in the form of granules, wettable powder, emulsion. and dust. As solid Carriers (fillers) for this, for example, calves, bentonite, clay, kaolin, diatrmic earth, vermiculite, slaked lime, etc. are used. For example, benzene, toluene, xylene, alcohols, acetone, metnaphaphthalene, dioxane, cyclohexanone, etc. As emulsifying agents, for example, alkyl sulfuric acid esters (esters), alkyl sulfonates, arylsulfonates, full nitrate glycol esters, polyhydric alcohols (esters), and the like are used. In practical use in the field, to ensure herbicidal action, surfactants are added to the compounds of formula (T), if necessary, also with other agricultural chemicals such as fungicides, insecticides, herbicides, etc. or with fertilizers.
    Example 1. In 100 MP of benzene, 23.5 g (0.1 mol) of 2,6-diethylanilinoacetic acid ethyl ester and 11.3 g (0.1 mol) of monochl acid chloride (rosus acid 1slot) are dissolved, then 11 g of triztilamine with stirring, maintaining the reaction temperature at about 10-20 ° C, then stirring for 2 hours at room temperature.The resulting solution is washed successively with a 5% aqueous solution of sodium hydroxide, a 5% aqueous solution of hydrochloric acid, and water. the layer is dried over anhydrous sodium sulfate. Benzene is distilled off in a vacuum; The target product is yl-chloroacetin-2,6-diethylaniline-acetic acid ethyl ester, p 1.5225.
     Found,%: C 61.81; H 7.0V; N 4.42; C1 11.48.
    C H jNClOj.
    Calculated,%: C, 61.63; H 7.11; N 4.49; C1 11.37.
    Other compounds of formula (1) are obtained similarly, the list and indicators of which are listed in Table 1.
    EXAMPLE 5. In 100 ml of tetrahydrofuran, 22.6 g (O, mol) of 2,6-diethylchloroacetoanilide are dissolved, then at room temperature and 45 g of a hexane solution containing Nbuty lithium is added dropwise while stirring. . Then, l |, 3 g (0.1 mol) of ethyl chloroacetic acid is added and the mixture is heated at the boiling point (e) by refluxing) for hours. After cooling, the reaction mixture is cooled.
    the mixture is poured on 20 g of ethanol, and the solvent is distilled off under vacuum. The residue after distillation is extracted with 100 MP ether (diethyl ether).
    5 Washed with water, the ether layer was dried over anhydrous sodium sulfate, the solvent was distilled off, to obtain 24.9 g of ethyl ester of N-chloroacetyl 2,6 diethylaniline acetic acid,
    O pJ 1.5228.
    Found,%: C 61.77; H 7.20; N 4.46; C1 1 1.22.
    .
    Calculated,%: C 6-1,63; H 7.11; 5 N 4.49; C1 11.37.
    Compounds of formula (1) are obtained in a similar way, the list and indicators of which are given in Table 2.
    Example 8 p 9. In 100 MP of benzene 0, 24.7 g of 2,6-diethylanshino-acetic acid allylic ester are dissolved. and 11.3 g of monochloroacetic acid chloride, then 11 g of triethylamine are added dropwise while stirring, maintaining the reaction temperature in the range of 10–20 ° C, and then stirring is continued for 2 hours at room temperature. The resulting solution was washed successively with a 5% aqueous solution of sodium hydroxide, a 5% aqueous solution of hydrochloric acid, and water. The benanol layer is then dried over anhydrous sodium sulfate. The benzene is distilled off in vacuo and the N-chloroacetyl 2,6-diethyl aniloic cyclic acid allyl ester, 1.5288, is obtained.
    Elementary analysis.
    0 .-
    Calculated,%: C 63.05; H 6.85;
    N 4.33; C1 10.95. . WITH.. - .
    Found,%: C 63.09; H 6.85; 5 N 4.19; C1 10.88.
    Other compounds of formula (I) are obtained similarly, the list and indicators of which are given in Table 3.
    权利要求:
    Claims (2)
    [1]
    1. METHOD FOR PRODUCING ACYLANILINES of the general formula:
    z Y-C00R 3 x CR <t II where R ^ and R ^ are lower alkyl;
    R 3 is hydrogen, alkyl, lower alkenyl, lower artkinyl. or cyclohexyl;
    ~ H lower alkyl substituted by 1-4 halo atoms, t
    . Yes;
    Y is lower alkylene, characterized in that the compound of the general formula where R *, R ^, R 3 and Y have the above meanings, is reacted with halogen ! acid hydride of the general formula
    R COX,
    4 * . .
    where - has the above meanings,
    X is a halogen, in the presence of a dehydrohalogenating agent at a temperature from room temperature to the boiling point of the reaction mixture in an inert organic solvent.
    [2]
    2. The method according to claim 1, characterized in that as a dehydrohalogenating agent is used. triethylamine. ”
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    同族专利:
    公开号 | 公开日
    GB1377225A|1974-12-11|
    US3780090A|1973-12-18|
    DE2212268C3|1979-09-13|
    FR2141035A5|1973-01-19|
    BR7201491D0|1973-04-26|
    FR2323681B2|1978-03-24|
    US4402734A|1983-09-06|
    DE2212268B2|1979-01-25|
    FR2323681A2|1977-04-08|
    DE2212268A1|1972-09-28|
    SU721000A3|1986-11-30|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    GB1041982A|1963-09-30|1966-09-07|Boots Pure Drug Co Ltd|Herbicidal compounds and compositions|
    US3403994A|1964-10-15|1968-10-01|Monsanto Co|Herbicidal method|
    US3539618A|1966-04-15|1970-11-10|Monsanto Co|Oxamyl chloride substituted carbamates|
    GB1164160A|1966-12-30|1969-09-17|Shell Int Research|N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides|
    US3442945A|1967-05-22|1969-05-06|Monsanto Co|Phytotoxic alpha-halo-acetanilides|
    US3780095A|1970-04-08|1973-12-18|Byk Gulden Lomberg Chem Fab|Acylated anilino-carboxylic acids and their salts|
    US3830829A|1971-06-01|1974-08-20|Monsanto Co|Chlorophenoxyalkyl anilides|US3901685A|1971-06-01|1975-08-26|Monsanto Co|Herbicidal acetanilides 2-halo-n-|
    US3907544A|1971-06-01|1975-09-23|Monsanto Co|Herbicidal 2-halo-N--substituted acetanilides|
    DK140082C|1972-03-10|1979-11-19|Hercules Incorporated|
    US4034108A|1972-10-13|1977-07-05|Ciba-Geigy Corporation|N--N-haloacetyl-2,6-dialkylanilines for the control of phytopathogenic fungi|
    SE397191B|1972-10-13|1977-10-24|Ciba Geigy Ag|N--N-HALOACETYL-2,6-DIALKYLANILINES FOR USE AS FUNGICIDE|
    US4205168A|1973-09-24|1980-05-27|Chevron Research Company|N-Carbamylalkyl-2,6-dialkyl-α-haloacetanilides|
    FR2265726B1|1974-04-01|1978-03-17|Ciba Geigy Ag|
    CH587605A5|1974-04-01|1977-05-13|Ciba Geigy Ag|
    US4008066A|1974-04-08|1977-02-15|Ciba-Geigy Corporation|Phenylaminoacetamides for regulating plant growth|
    US4206228A|1974-04-09|1980-06-03|Ciba-Geigy Corporation|Microbicidal aniline derivatives|
    OA04979A|1974-04-09|1980-11-30|Ciba Geigy|New aniline derivatives useful as microbicidal agents and their preparation process.|
    US4098895A|1975-09-30|1978-07-04|Ciba-Geigy Corporation|Triazolylacetanilide compounds and microbicidal compositions|
    US4165381A|1975-09-30|1979-08-21|Ciba-Geigy Corporation|Microbicidal compositions|
    US4044147A|1976-05-26|1977-08-23|Pfizer Inc.|N--p-amino-N'--benzamide anti-ulcer agents|
    DE2648074A1|1976-10-23|1978-04-27|Bayer Ag|N-CHLORACETYL-N-PHENYL-ALANINE ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
    US4311516A|1976-10-29|1982-01-19|Montedison S.P.A.|Method of combatting plants which infest maize cultivations without damaging the maize|
    US4494978A|1976-12-30|1985-01-22|Chevron Research Company|Herbicidal N--2,6-dialkyl-alpha-haloacetanilides|
    US4243819A|1978-02-16|1981-01-06|Zoecon Corporation|Substituted amino acids|
    US4258196A|1978-04-17|1981-03-24|Monsanto Company|Process for the production of tertiary 2-haloacetamides|
    DE2836158A1|1978-08-18|1980-02-28|Bayer Ag|N-OXALYL DERIVATIVES OF N-PHENYL-AMINO ACID, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
    CH637368A5|1978-10-27|1983-07-29|Ciba Geigy Ag|ANILINE DERIVATIVES AND Pesticides Manufactured From Them.|
    US4650516A|1979-03-23|1987-03-17|Stauffer Chemical Co.|α-halo-Ω-haloalkylamides herbicidal antidotes|
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    DE2916692A1|1979-04-25|1980-11-06|Bayer Ag|N-ALLENYL ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP1460971A|JPS51178B1|1971-03-15|1971-03-15|
    FR7400874A|FR2323681B2|1971-03-15|1974-01-10|
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