• 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:
    3-Phenyl-5-(substituted)-4(1H)-pyridones of the formula I <IMAGE> are prepared by cyclising a compound of the formula IV <IMAGE> in which one of the two substituents Q<1> or Q<2> represents two hydrogen atoms, while the other of the two substituents represents a group of the formula =CHNHR, using a formylating agent. In the compounds of the formulae I and IV, the radicals R, R<1> and R<2>, and m, have the meaning given in Patent Claim 1. The pyridones can be reacted with phosphorus pentasulphide to prepare the corresponding pyridothiones. Both the pyridones and the corresponding pyridothiones, and also the salts of these compounds, are employed as the active component in herbicides. They display their activity against an unusually broad range of weeds.
    公开号:SU716522A3
    申请号:SU772446155
    申请日:1977-01-26
    公开日:1980-02-15
    发明作者:Меллон Тейлор Харольд
    申请人:Эли Лилли Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for producing new pyridine derivatives, which may find application in agriculture.
    A method is known in the literature for the transfer of the oxy group of heterocyclic compounds by their interaction with Pi> S 5 (1].
    The aim of the invention is to develop a basic on a known reaction of a method for producing new biologically active compounds.
    This goal is achieved by the method of obtaining 3-Lenyl-5-substituted-4 (1H) -pyridinediones -
    general formula / 1 ΛYu ~ ilT RZ ("),and
    where R is C ^ -C ^ -alkyl; R ^ is hydrogen, trifluoromethyl, C ^ -C ^ -alkyl, halogen, methoxy or methylthio; I am 2 C ^ -Cd-alkyl, C ^ -C 3 -alkoxy, C ^ -C ^ -alkylthio, phenyl, phenoxy, phenyl.thio or Phenyl, phenoxy or Phenylthio monosubstituted with trifluoromethyl, -C ^ -alkyl, halogen, methoxy
    Or methylthio or their salts, л t l y ^ characterized in that the compound of general formula AND
    where R, R -1 and R 2 have the indicated meanings, are reacted with P 2 S 5 in pyridine, quinoline or picoline at a temperature of from 20 ° C 1S to the boiling point of the reaction mixture and the target product is isolated or converted into an acid addition salt.
    Example 1. The south of 3,5-diphe20 nil-1-methyl-4 (1H) -pyridone is mixed with 10 g of P ^ Sg in 100 ml of pyridine and the mixture is refluxed for 2 hours, after which it is poured into a large amount 25 water and stirred for 1 hour. Then the mixture is filtered, the solid product is recrystallized from ethanol to obtain 9.8 g of 3,5-diphenyl-1-methyl-4 (1H) -pyridinethione, mp.
    168-171 ° C.
    According to the method of example 1, the following typical pyridinthiomas were obtained. .
    3,5-bys-TZ-chlorophenyl) -1-methyl-4 (1H) -Pyridinedione, mp. 210 212 ° C, yield 86% 5 , 5 / 3- (3-Chlorf & nyl) -1-methyl-5-phenyl * 4 (ΪΉ) pyridinethione, mp 19O-193 ° C, 71% yield.
    1-methyl-3-phenyl-5/3-trifluoromethylphenyl-4 (1H). pyridinethione, mp, 210 ^ 0,, θ yield 70%. ,
    3- (3-Bromophenyl.) - 1-methyl-5-phenyl-4 (1H) pyridinedione, m.p. 185188 * C, yield 59%.
    1-Methyl-3- (4-chlorophenyl) -5- (3-trifluoromethylphenyl) -4 (1Н) -pyridinethione, 1 5 mp 229-242 ° С, 25% yield ..
    1-Methyl-3- (3-meth and l phenyl) -5- [3-trifluoromethylphenyl] -4 (1H) pyridinethione, Ϊ * mp. 193-196 R C, yield 50%.
    1-Methyl-Z- (2-methylphenyl) -5- (3-20
    trifluoromethylphenyl) -4 (1H) pyridinethione, T.P. 193-195 ° C, yield 35%.
    1-Methyl-Z-propyl-5- (3-trifluoromethylphenyl) g4 (1H) pyridinedione, mp. 145-148 r C, yield 40%.
    1-Methyl-3-phenoxy-5- (3-trifluoromethylphenyl) -4 (1H) pyridinethione, m.p. 127-131 ° C, yield 40%,
    EtylTio 3-1-methyl-5- (3- triftorme tilfenil) -4 (1H) pyridinethione,: m.p. 136-138 R C, yield 55%, '
    3-ethoxy-1-methyl-5- (3-trifluoroMe5 Ylphenyl) -4 (1H) pyridinedione, mp. 153-155 ° C, 5% yield.
    权利要求:
    Claims (1)
    [1]
    According to the method of example 1, typical pyridinium compounds were obtained; 3,5-5IS-G-chlorophenyl) -1-methyl-4 Cn) -g1yrydintirn, so pl. 210212С, exhaust. 86%. / 3- (3-Chlorof | ntsl) -1-methi -5-phenyl 4 (ta) n "fusion, t.p. 190-193 ° C, yield 71%. 1-methyl 3-phenyl-5/3-trifluoromethyl phenyl-4 (1H pyridinethione, mp. Zy, 70%, 1 3- (3-Bromophenyl.) -L-methyl-5-phenyl-4 (lH ) pyridinthione, mp 185188 C, 59% yield. 1-Methyl-3- (4-chlorophenyl) -5- (3-trI fluoromethylphenyl) -4 (1H) -pyridinthione, mp.239-242 C , yield 25%. 1-Methyl-3- (3-methylphenyl) -5-3-tr fluoromethylphenyl-4 (1H) pyridinium, g, pl. 193-196 s, yield 50%. 1-Methyl-3- { 2-methylphenyl) -5- (3-trifluoromethylphenyl) -4 (1H) pyridinthio Tn; i.L93-i95C, yield 35%. 1-Methyl-3-propyl-5- (3-trifluorome Nlphenyl) g4 (1H) pyridinium, m.p. 145-14s, wyzSod 40%. 1-Methyl-3-phenoxy-5- (3-trifluoromethylphenyl) -4 (1H) pyridinium, mp 127-131 s, yield 40%. 3-5fyl io-1-methyl-5- (3- trifluorum tylphenyl) -4 (1H) pyridinethione, m.p. 136-1-38 C, 55% yield, 3-9TOXI-1-methyl-5- {3-trifluorome RILPHENY) -4 (1H) pyridinethione, m.p. NZ-aZ C, 5% yield. Claims of the invention The method of producing 3-phenyl-5-N-1 -N-4 (1H) pyridinethion of the general formula 1., where R is C-C „-alkyl; R is hydrogen, trifluoromethyl, C C-alkyl, halogen, methoxy or methylthi. R C-Cd-alkyl, -alkoxy, C-C-alkylthio, phenyl, phenoxy, phenylthio or phenyl, phenoxy or phenylthio, mono-substituted with trifluoromethyl, C, -Cd-alkyl, halo, methoxy or methyl tir or their salts, distinguished by that a compound of the general formula I, where R, R and R have the indicated meanings, is reacted with S. pyridine, quinoline or picoline at a temperature of from 20 ° C to the temperature that the reaction mixture boils and the target product is isolated or converted to acid addition salt . Conventional priority according to the following signs: 28.08.74 g at R - C-Cdalkyl, R - hydrogen, C-C alkyl, halo, methoxy, K phenyl, phenyl, monosubstituted with trifluoromethyl, halo, methoxy; 03.07.75 g. With R - swept methylthio, C-C-alkyl, C-C-alkoxy. C.) - C-alkylthio, Lenoksi, phenylthio, substituted phenoxy, substituted phenylthio, methylthiophenyl, Sources of information taken into account in the examination 1. Heterocyclic compounds, ed. Elderfield. M., World, 1969, p. 245.
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    同族专利:
    公开号 | 公开日
    IL47938A|1979-07-25|
    DK385075A|1976-02-29|
    NL181272B|1987-02-16|
    AT365577B|1982-01-25|
    YU39076B|1984-04-30|
    BE832702A|1975-12-16|
    FR2283130B1|1983-04-08|
    AR218211A1|1980-05-30|
    PL109320B1|1980-05-31|
    TR19047A|1978-03-20|
    IT1042113B|1980-01-30|
    JPS5148671A|1976-04-26|
    NL181272C|1987-07-16|
    SU1074403A3|1984-02-15|
    OA05093A|1981-01-31|
    NZ178426A|1978-06-20|
    IL47938D0|1975-11-25|
    JPS60350B2|1985-01-07|
    YU216375A|1982-02-28|
    IE42444L|1976-02-28|
    NO752942L|1976-03-02|
    AU8427875A|1977-03-03|
    DE2537753A1|1976-03-11|
    DE2537753C2|1984-05-30|
    CA1075696A|1980-04-15|
    HU169687B|1977-02-28|
    JPS5151520A|1976-05-07|
    NO145617B|1982-01-18|
    ATA660375A|1981-06-15|
    LU73264A1|1976-04-13|
    NL7509935A|1976-03-02|
    BR7505487A|1976-08-31|
    JPS611401B2|1986-01-17|
    EG12953A|1980-03-31|
    PL111873B1|1980-09-30|
    IE42444B1|1980-08-13|
    DD127452A5|1977-09-21|
    CH632248A5|1982-09-30|
    DD123461A5|1976-12-20|
    FR2283130A1|1976-03-26|
    MX5136E|1983-03-28|
    GB1521092A|1978-08-09|
    CH630356A5|1982-06-15|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    AT362613B|1975-08-27|1981-06-10|Lilly Co Eli|HERBICIDAL AGENT|
    US4051142A|1976-05-24|1977-09-27|Rohm And Haas Company|1-Aryl-4-pyridones|
    US4174209A|1978-06-19|1979-11-13|Eli Lilly And Company|Herbicidal 1-alkyl-3-phenylpyridinium salts|
    EP0073999B1|1981-09-05|1986-01-15|Bayer Ag|Pyridin-4-one derivatives substituted by a heterocyclic ring, process for their preparation and their use as herbicides|
    AU570466B2|1983-06-17|1988-03-17|Rhone-Poulenc Agro|3-oxo-2,3-dihydrofuran derivatives|
    US4537623A|1984-03-29|1985-08-27|Chevron Research Company|Herbicidal 2-5-amino-3-oxo-4--2,3-dihydrofurans|
    US4568376A|1984-05-09|1986-02-04|Chevron Research Company|Herbicidal 5-amino-3-oxo-4--2,3-dihydrofuran and derivatives thereof|
    US4596595A|1984-06-22|1986-06-24|Chevron Research Company|Herbicidal 5-amino-3-oxo-4--2,3-dihydrothiophene and derivatives thereof|
    DE3430232A1|1984-08-17|1986-02-27|Bayer Ag, 5090 Leverkusen|N-METHYL-4-PYRIDONE|
    US4606756A|1984-10-26|1986-08-19|Chevron Research Company|Herbicidal 2-5-amino-3-oxo-4--2,3-dihydrofurans|
    US4568375A|1984-10-26|1986-02-04|Chevron Research Company|2-Substituted 5-amino-3-oxo-4--2,3-dihydrofuran herbicides|
    US4568378A|1984-12-21|1986-02-04|Chevron Research Company|Herbicidal 5-cycloalkylamino-3-oxo-4--2,3-dihydrofuran and derivatives thereof|
    US4568377A|1985-04-26|1986-02-04|Chevron Research Company|Herbicidal 5-amino-3-oxo-4--2,3-dihydrofuran|
    US4978386A|1985-06-11|1990-12-18|Chevron Research Company|Herbicidal 2--3-amino-2-cyclopentenone derivatives|
    DE3531773A1|1985-09-06|1987-03-19|Bayer Ag|3.5 DISUBSTITUTED 4-PYRIDONE|
    CA1317599C|1986-03-26|1993-05-11|Yukio Nezu|1,2,6-triphenyl-4-pyridinone derivatives, production and uses thereof|
    DE19518739A1|1995-05-22|1996-11-28|Basf Ag|N-aminopyridone derivatives|
    DE69735049T2|1996-02-02|2006-07-20|Kumiai Chemical Industry Co., Ltd.|PYRIDINE DERIVATIVES AND HERBICIDES|
    EP2052612A1|2007-10-24|2009-04-29|Bayer CropScience AG|Herbicide combination|
    DE102008037629A1|2008-08-14|2010-02-18|Bayer Cropscience Ag|Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides|
    US11026423B2|2013-04-17|2021-06-08|Sepro Corporation|Herbicidal compositions and methods|
    JP2017206440A|2014-09-10|2017-11-24|日本曹達株式会社|Pyridine compound and use therefor|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US50142474A| true| 1974-08-28|1974-08-28|
    US59166175A| true| 1975-07-03|1975-07-03|
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