• 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:
    Hydantoin N-methylol esters of the formula, <IMAGE> wherein one of X and Y is a carbonyl group and the other is a methylene, ethylidene or propylidene group, R1 is a lower alkyl, lower alkenyl or lower alkynyl having up to 3 carbon atoms, R2 is a group represented by the formula, <IMAGE> in which R3 is a hydrogen atom or a methyl group; when R3 is a hydrogen atom, R4 is a methoxyiminomethyl or 2,2-disubstituted vinyl group in which the substituents can be selected from the group consisting of methyl, vinyl, fluorine, chlorine and bromine, or both of the substituents may form tetramethylene chain; when R3 is a methyl group, R4 is a methyl group; R5 is a methyl, methoxy, fluorine, chlorine, bromine or 3,4-methylenedioxy group; and n is 1 or 2, a process for producing the same, insecticides and acaricides containing the same as an active ingredient, and novel intermediate compounds.
    公开号:SU850003A3
    申请号:SU782628302
    申请日:1978-06-19
    公开日:1981-07-23
    发明作者:Итая Нобусиге；Хирано Масатика
    申请人:Сумитомо Кемикал Компани, Лимитед (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of the M-methyl ester hydanthone formula of formula. I where one of the x and y x and y is a carbonyl group and the other is methylene, ethylidene or propylidene, RY is lower alkyl, lower alkenyl, or lower alkynyl, having up to 3 carbon atoms, R, j is a group represented by The formula is -c-c: C CHj CMj, K, is a hydrogen atom or a methyl group, if Ra is a hydrogen atom, then R ,. is methoxyimino methyl or 2,2-disubstituted vinyl in which the substituents can be selected from the group comprising methyl vinyl, chlorine, fluorine and bromine, or both substituents can form a tetramethylene chain; if R is a methyl group, then R is also a methyl group, Rg is methyl, methoxy, fluoro, chloro, bromo or 3,4-methylenedioxy and n is 1 or 2, which can be used as insecticides and acaricides. A known method for producing esters by reacting alcohols with carboxylic acids or their derivatives 1. The purpose of the invention is the synthesis of new compounds possessing valuable properties and allowing them to be used in agriculture. This goal is achieved in that according to the method for preparing the N-methyl hydantoin esters of the formula G, an alcohol or its halide of the formula. —— Where are R, X and Y as defined above, and A represents a hydroxyl group or a halogen atom such as chlorine or bromine, with a carboxylic acid of the formula C-C-H-O-OH I O (° GHj OH R Rj.R and n are defined as f 7, F j (higher values, or with its reactive derivative. Reactable carboxylic acid derivative means acid halides (mixed) acid anhydrides alkali metal salts and organic tertiary base salts. If an alcohol of formula II is used (i.e., in this case, A is a hydroxyl group) and a carboxylic acid of formula III or IV, the reaction is preferably carried out in the presence of a dehydrating agent such as dicyclohexylcarbodiimide, in an appropriate solvent such as benzene, toluene, diethyl ether at a temperature from lOoc to the boiling point of the solvent used, and the reaction proceeds from 30 minutes to one day. If an alcohol of formula II is used (i.e., A is a hydroxyl group in this case) and an acid halide, preferably chloride or bromide of formula III or IV, then the reaction is carried out mainly in a suitable solvent such as benzene, toluene, diethyl ether at temperatures from 0 ° C to the boiling point of the acceptor used, for example, an organic tertiary amine, i.e. pyridine or triethylamine. The reaction is completed shortly after mixing the reagents. If (mixed) acid anhydride is used instead of acid halide, the reaction is carried out in the same way, except that the reaction proceeds more slowly and at elevated temperatures. If a halide derivative of an alcohol of formula II is used (i.e., in this case, A is chlorine or bromine), then the carboxylic acid of Formula III or IV is used as an alkali metal salt or an organic tertiary basic salt or they can be added into the reaction system together with the corresponding base. An alcohol of formula II (i.e., with A in the value of hydroxyl) is easily obtained by reacting the corresponding hydantoin with a formaldehyde or its equivalent (i.e., paraformaldehyde), the halogen-substituted spir compounds of the formula II (i.e. in which A is halogen such as lor or bromine) are easily obtained with alcohol reakia. formulas And with a halogenating agent (i.e. with oxophosphorus oxide, phosphorus trichloride, phosphorus rechbromide, hydrochloric acid, hydrobromic acid, thionyl chloride). Example I. 8.4 g of 1-propargyl-3-hydantoinylmethyl alcohol are dissolved in a mixture of 26 ml of benzene and 6 g of pyridine, and a solution of 12.0 g of d6-cis-trans-2-chloride is added dropwise to the solution while stirring , 2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylic acid in 36 ml of benzene. The reaction mixture is left overnight and a small amount of water is added to dissolve the precipitated pyridine hydrochloride, and the resulting salts are separated from each other. The organic layer is sequentially washed with 5% aqueous hydrochloric acid, an aqueous solution of sodium carbonate and a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The benzene solution is concentrated and purified by chromatography on silica gel. Yield 16.7 g (93.0%), 1.5341. Found,%: c 50.41, H 4.32, N 7.62. Calculated,%: C 50.15, H 4.4, N 7.80. Example 2. 8.4 g of 1 propargyl-2-hydantoinylmethyl alcohol and 9.0 g of d, 0-trans-2,2-dimethyl-3- (2-methylbutadienyl) cyclopropanecarboxylic acid are dissolved in 52 ml of benzene and in solution while stirring, 16.5 g of dicyclohexylcarbodiimide is added and the mixture is left overnight. The next day, the reaction solution is heated at reflux temperature for 2 hours and cooled. The precipitated dicyclohexyl urea is removed by filtration, and the solvent is concentrated. The subsequent processing is carried out according to Example 1. Exit 11.1 (67.3%), 1.5373. Found,%: C 65.19, 6.78, N 8.40. / Calculated,%: C 65.43, H 6.71, N 8.48. Example 3. 8.5 g of 1 allyl-3-hydhentoinyl methyl alcohol is dissolved in a mixture of 26 ml of toluene and 6 g of pyridine, 20.4 g of flC- (4-chlorophenyl) isovaleric anhydride is added to the solution, followed by heating at reflux temperature for 3 hours. After cooling, the resulting toluene solution is extracted with 5% sodium hydroxide to remove the carboxylic acid formed as a by-product, followed by washing with a final charge. aqueous solution of sodium chloride. The toluene solution was concentrated and the remaining operations were carried out as in Example 1. The yield was 13.0 (71.0%), nf 1.5357. Found,%: C 58.92, H 5.77, N 7.49. calculated in%: C 59.26, H 5.80, N 7.68. Example 4. 9.3 g of 1-propargyl-3-hydantoinylmethyl chloride and 11.7 g of 0 dB-trans-2,2-dimethyl-3-cyclopentylidenemethylcyclopropanecarboxylic acid are dissolved in 63 ml of acetone and a solution of 8.1 g is added to it trimethylamine in 63 ml of acetone is added dropwise. 15 The reaction mixture is gradually heated to reflux temperature and heating is continued at this temperature for 2 hours. After cooling, triethyl- 20 hydrochloric acid is removed by filtration, water and benzene are added to the filtrate stir by shaking and divide into two layers. The organic layer is successively washed with a 5% aqueous solution of sodium hydroxide and with a saturated aqueous solution of sodium chloride and the solvent is concentrated. Subsequent operations are performed analogously to Example 1, Yield 10.7 g - (62.1%), 1.5172. Found,%: C 66.30, H 7.08, N 8.39. C, 66.26; H, 7.02; Calculated,%: N, 8.13. The following compounds are obtained and C, HCEC-CH -N s-nc-o-o-cn-cc. c: -c 1-propargyl-3-hydanthionylmethyl-2,2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylate g (d &amp; c-trans-ether: pr 1.5341) (rt-trans- Ether: 1.5328)
    .h-s
    CH-Cn, -. M-CHJD C-CH-CH-CH C
    one
    with
    one
     N
    si
    1-allyl-3-hydantoinylmethyl 2,2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylate
    (d8-cis-trans-ether: njf
    1.5303)
    (
    / te
    cwrCH-w -N N-CH o s-sn-sn-s-ss
    IIOC
    V
    X
    Cn, pa Zaf-c HZ2, -Ci NS 1-p ester-cci KrC 1-n ester
    about
    |
    xCHv ce
    HC-.C-CM -N N-CH-0-C-CH - CH.CH C
    I
    about hjco
    sn.

    ABOUT
    2,2-Dimethyl-3-cyclopentylidenemethylcyclopropanecarboxylic acid 1-propargyl-3-hydantoinylmethyl ester (de-trans-ether: nif 1.5172)
    ABOUT
    ABOUT
    II
    Snp,
    ., OS-si-si
    Metc-cHj
    sn
    four-
    H / CKj
    about propyl-3-hydantoinylmethyl-2,2-dityl-3- (2,2-dichlorovinyl) -cycloproncarboxylate (d-cis-trans-ether: p 1.5288) -CM-CHSC x dd, - m- c-c-cc-c-sleep propargyl-1-hydantoinylmethyl resin 2,2-dimethyl-3- (2,2-dichlorovinyl) and cyclopropanecarboxylic acid (d-cis-trans-ether: n 1.5365) xYN- CH, 0 — C — CH — CH — CH — C — CH — CV jN I, r, j S with —CH j / CH C “j llyl-1-hydantoinyl methyl ester 2-dimethyl-3- (2,2-dichlorovinyl ) klopropancarbonovaya (dg-cis-trans-ether: 1.5290) Ñ-СН. -М N-CH, jO-C-CM. ropargil-3-hydantoinylmethyl p 2,2-dimesh-3- (2,2-difluoromethyl) clopropanecarboxylic acid (a6-trans-ester: 1.4925) -CK -N N-CH-0-C-CH - CH -CH 1 (and - ° n, ropargil-3-hydantoinylmethyl p of chrysanthemic acid (d-trans-ether: 1.5185)
    2,2-3,3-tetramethyl-cyclopropanecarboxylic acid 1-propargyl-3-hydantoinyl methyl ester
    (melting point 86-93c)
    1-propargyl-3-hydantoinyl methyl ester of L - (4-methylphenyl) -sovaleric acid
    (1.5257)
    0-C-CM - CMCSC
    “Cr si
    "G CHj
    2,2-Dimethyl-3- (2-methylbutadienyl) cyclopropanecarboxylic acid 1-propargyl-3-hydantoinyl methyl ester (df-trans ether; 1.5773)
    H C-.CH-CV.-H VCH O-C-CM-CHCH C
    11 о с
    xh
    5VV
    sn.
    WITH"
    about II
    sn.
    SV, C4, jCLY
    l-CHj- M l-CKjO-C -tH
    CH
    1-propargyl-3-hydantoinylmethyl ether - (3,4-methylenedioxyphenyl) -isovaleric acid (1.5371)
      "HCtC-CH, -" -SI-O
     II 1-propargyl-3-hydantoinylmethyl ester 2,2-dimethyl-3- (2,2-dibromo-cyclopropanecarboxylic acid (d-trans-ether: p 1.5925) (d-cis-ether: p 1.5921) p., 0-C-CH-tH-CH-N-0HC "CH-CHj IJ h 1-propargyl-3-hydantoine naphthylether 2,2-dimethyl-3-methoxyiminomethyl cyclopropanecarboxylic acid (d-ether-1.5175) HC C-CH - N M-CH-OO-CH 1-propargyl-3-hydantoinylmethyl ester 01 - (4-chlorophenyl) -isovalerian acids 1.5377) SK xCS хСч. HC c-CHj-N H -CM, jO-c -n H, U4 ° 1-propargyl-3-hydantoinylmethyl ester of α- (3-chlorophenyl) -io-valeric acid (p, 1.5391)
    9
     /
    xy MCsC-CHj-w m-SMdO-cn-I.
    I I
    ABOUT
    Cc 1-propargyl-3-hydantoinyl methyl ester (t- (4-methoxyphenyl) -isovaleric acid 1.5290) ОЧр-С-с-н g f OMjtcH-CHj II 1-allyl-3-gndantinoylmethyl ether L (4-bromophenyl ) -isovaleric cis (ni 1.5423) -L f-CHeO-. I.S., 1-propargyl-3-hydantoinyl methyl ether ot- (3,4-dichlorophenyl) -isovaleric acid (n 1.5403) HC5C-CH-allyl-3-hydantoinyl methyl ether t- (4-chlorophenyl) -isovaleric acid - (, f 1.5357)
    3-p1ropargil-1-hydantoylH11lmethyl 1L ether c6- (4 fluorofensh1) - eoyaleric acid
    (p "1.4478) |
    M «c - S-cw-: f- w
    tib.i-.c; / V
    0j L CMjCH
    . 1-prop1fgyl-4-metr l 3-g1i | antovi11l oryl ester 2,2-d | methyl-2- (2,2dichlornovyl) -cycltropancarOanonic acid .v
    . | ... snn; -H sn,
    The table shows the eaicheii radicals R, x. Y and d compound fsmmyly
    1-propargyl-5-methyl-3-hydantoinylmethyl ester chryantemotec kHcnoTu
    thats
    -sie
    OcC-Cty
    at
    H
    ct
    C- P% "
    / h
    CHjCHj
    g-propargi-3-ethyl-3-hydantoinyl methyl 2,2-dimethyl-3- (2,2-dhhpsch biyl) -cyclopropanecarboxylic ester
    acid.
    T
    where one of the radikgshovs X and Y is where R is an atom
    carbonyl group, and the other is a non-hydrogen or methyl group. Cd
    Tylenoyl, ethylidene or Ps is a methoxyiminomethyl- or
    The den group, R, is a lower, 2-double-valued vinyl group. wherein the substituents can be selected from the group comprising methyl, vinyl, fluorine, chlorine and bromine or both substituents can form a tetramethylene chain; if R is a methyl group, then L is also methyl to group, Rj represents methyl, methoxy, fluorine, chlorine, bromine or 3,4-methylene-dioxygroup and n is 1 or 2, characterized in that the alcohol or its halide of formula II XS, where R, X and Y have the above values, A is a hydroxyl group or a halbene atom, is reacted with a carboxylic acid of formula III or IV CCM-O-OH n-o (H where RT, "G,, Rg and p have the meanings indicated above, or with its reaction derivative, with B14 aiming the target product. 2. The method according to claim 1, characterized in that when A is a hydroxyl group, its acid halide or anhydride is used as a reactive derivative of a carboxylic acid and the process is carried out in an organic solvent and in the presence of an acid acceptor. 3. The method according to claim 1, wherein is a hydroxyl group, the reaction of a compound of formula II with a carboxylic acid is carried out in an organic solvent medium in the presence of a dehydrating agent. 4. A method according to claim 1, characterized in that when A is a halogen, its alkali metal salt or its organic tertiary base salt is used as a reactive carboxylic acid derivative. Sources of information taken into account in the examination 1. Carrer P. COURSE of organic chemistry. L / Chem. literature, I960, p. 262.
    权利要求:
    Claims (4)
    [1]
    Claim
    1. method of obtaining the Ν-methyl esters of hydantoin of the formula
    alkyl, lower alkenyl or lower alkynyl having up to 3 carbon atoms of L-55, B 2 'is a group of formulas
    60
    G ζΜ- ™
    ei> © 4
    where one of the X and Y radicals is a carbonyl group, and the other is a methylene, ethylidene or propylidene group, 1C is the lowest
    in which is an atom
    hydrogen or methyl group, K 4
    is methoxminomete- or
    65 2,2-disubstituted vinyl group
    eleven
    850003
    12
    in which the substituents can be selected from the group comprising methyl, vinyl, fluorine, chlorine and bromine, or both substituents can form a tetramethylene chain; if it is a methyl group, it is also a methyl group, is a methyl, methoxy, fluorine, chlorine, bromine or 3,4-methylene-dioxy group and η is 1 or 2, characterized in that the alcohol or its halide of the formula I
    where 1 ^, X and V have the above values, A is a hydroxyl group or a halogen atom, is reacted with a carboxylic acid 20 of formula III or IV.
    Ά '. £
    iki
    * 5 <
    SI
    I η and O
    25
    where, K 5
    yours,
    and η have the value indicated with its reactionary
    derivative, with the selection of the target product.
    [2]
    2. The way pop. 1, characterized in that when A is a hydroxyl group, its acid halide or anhydride is used as a reactive carboxylic acid derivative and the process is carried out in an organic solvent medium in the presence of an acid acceptor.
    [3]
    3. The method according to π. 1, in that when A is a hydroxyl group, the reaction of a compound of formula II with a carboxylic acid is carried out in an organic solvent medium in the presence of a dehydrating agent.
    [4]
    4. The method according to π. 1, characterized in that, when A is a halogen, its alkali metal salt or its organic tertiary base salt is used as a reactive carboxylic acid derivative.
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    同族专利:
    公开号 | 公开日
    FR2415105A1|1979-08-17|
    DE2826864C2|1989-07-06|
    NL188904C|1992-11-02|
    DE2826864A1|1979-01-11|
    JPS549269A|1979-01-24|
    HK56381A|1981-11-27|
    US4176189A|1979-11-27|
    ZA783058B|1979-06-27|
    IT7849931D0|1978-06-19|
    JPS609715B2|1985-03-12|
    HU176713B|1981-04-28|
    GB1581124A|1980-12-10|
    MY8200170A|1982-12-31|
    AU3671778A|1979-12-06|
    AU508983B2|1980-04-17|
    IT1105521B|1985-11-04|
    DK159430B|1990-10-15|
    AR218921A1|1980-07-15|
    CH636861A5|1983-06-30|
    NL7806586A|1978-12-22|
    NL188904B|1992-06-01|
    FR2415105B1|1984-10-05|
    DK159430C|1991-03-18|
    CH638188A5|1983-09-15|
    DK275878A|1978-12-21|
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    JP52073721A|JPS609715B2|1977-06-20|1977-06-20|LV920389A| LV5242A3|1977-06-20|1992-12-22|Saturation of hydantoin n-methyl esters|
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