• 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:
    The present invention relates to mixtures of guanidated aliphatic polyamines, or their acid addition salts, having antimicrobial or pesticidal effect. More particularly the invention relates to such mixtures which have a total degree of guanidation exceeding 30%. The mixtures are suitable for agricultural and industrial use.
    公开号:SU852169A3
    申请号:SU782618097
    申请日:1978-05-29
    公开日:1981-07-30
    发明作者:Аксель Христер Берклунд Джеймс；Рагнар Ройтерхель Альф
    申请人:Кеманорд Аб (Фирма)；
    IPC主号:
    专利说明:

    Example 1, Preparation of .tatas. Of a guanidated 1,13-diamino-7-aeattripecane.
    110 g of 1,13-diamino-7-aerodridecane is dissolved by partial neutralization in 250 g of water containing 74 g of acetic acid. The mixture is heated until 154 g (50%) of the cyanamide solution is added. The reaction of the mixture is continued at 75 ° C for 5 hours. The solution is neutralized with 18 g of acetic acid. The degree of guanidization of the resulting mixture is 92%. After evaporation of the solvent and separation, the mixture is obtained;
    a) 200 g (75% of theory) of 1,7,13-triguanidated 1,13-diamino-7-azatridecane triacetate with mp, 153 ° C
    5) 29 g (12% of theory) of 1.7-diguanidized triacetate of 1,13-diamino-7-azatridecane with m.p.
    b) 12 g (5% of theoretical) of 1,13-diguanidized 1,13-diamino-7-azatridekane triacetate with m, pl „
    1230С; PRI mme R 2. Obtaining guanidated triacetates 1,13-diamino-7-azatridecane and 1,17-diamino-9-azaheptadecane.
    100 g of 1,13-diamino-7-azatridecane and 100 g of 1,17-diamino-9-azaheptadecane are added to a mixture of 70 g of water and 100 g of acetic acid. The mixture was heated to T5 ° C and 190 g of 50% cyanamide was added over 3 hours. After stirring at 75 ° C for 5 hours, the reaction mixture is neutralized with 35 g of acetic acid. The resulting mixture has a guanidation rate of 78%. After evaporation of the solvent and separation of the mixture, the following is obtained:
    a) 98.6 g (46% of theory) of triacetate 1,9,17-triguanidirovannogo 1D7 diamnno-9-azaheptadekana st. mp.
    b) 50 g (25% of theoretical) of triacetate. 1,9-diaguanidized: L J A7 diamino-9-azaheptadecane with mp 1230 ° C;
    (B) 23 g (11% of theoretical) of 1,17-diguanidized 1,17-d5-at "Shno-9-azaheptadecane triacetate with mp 1400 ° C;
     g (9% of theory) of mono-guanidized 1,17-diamino-9-azaheptTc1decane triacetate with mp B7 ° C;
     E) 110 g (45% of theory) of triacetate of 1,6,13-triguanidated 1,13-diamino 7-azatridecane with m.p. 1530С;
    e -55 g (25% of theoretical) triacetate 1,7-digenidirovannogo i, 13-diamino-7-azatridekane with t, Sh1. 1070s;
    G) 30 g (13% of theoretical) of 1,13-diguanidized triacetate
    1,13-diamino-7-azatridecane with m.p. 1230С:
    1) 18 g (9% of theory) of mono-guanidized 1,13-diamino-7-azatridecane triacetate with m.p.
    Example 3. Preparation of guanidated 1,17-diamino-9-azaheptadecane triacetate.
    200 g of 1,17-diamino-9-azaheptadecane are added to a mixture of 80 g of water and 95 g of acetic acid. The mixture is heated to and 205 g of 50% cyanamide is added over 3 hours. After stirring at 8 ° C for 5 hours, the reaction mixture is neutralized with 30 g of acetic acid. The resulting c viecb has a guanidation rate of 88%. After evaporation of the solvent and separation of the mixture, the following is obtained:
    a) 170 g (66% of theory) of triacetate of 1,9,17-triguanidated 1,17-diamino-9-azaheptadecane with mp 161 ° C;
    b) 42 g (17% of theoretical) triacetate of 1,9-diguanidized 1,17-diamino-9-azaheptadecane with m.p. 1230 ° C;
    b) 20 g (9% of theory) of 1,17-diaguanidated 1,17-diamino-9-azaheptadecane triacetate with mp 140 ° C;
    2i) In g (3% of theoretical) of mono-guanidized 1,17-diamino-9-azaheptadecane triacetate with m.p. 87 ° C.
    Example 4. Obtaining guanidated triacetate of 1,17-di Eno-9-azaheptadekana.
    200 g of 1,17-diamino-9-azaheptadecane are added to a mixture of 20 g of water, 50 g of ethylene glycol and 95 g of acetic acid. The mixture is heated to and 185 g of 50% cyanamide is added over 3 hours. After stirring for 7 hours, the reaction mixture is neutralized by the addition of 30 g of acetic acid. The resulting mixture has a guanidation rate of 82%. After evaporation of the solvent and separation of the reaction mixture:
    ) 136 g (53% of theoretical) triacetate of 1,9,17-diamino-9-azaheptadecane with m.p. 161С;
    b) 55 g (23% of theoretical) triacetate of 1,9-diguanidized 1,17-diamino-9-azaheptadecane with m.p. 123®С;
     B) 27 g (11% of theoretical) of triacetate of 1,17-diaguanidated 1,17-diamino-9-azaheptadekan with m.p.
    ) 16 g (7% of the theoretical) triacetate of mono-guanidized 1,17-diamino-9-azaheptadecane with mp 85 ° C.
    Example 5. Preparation of guanidated triacetate1,17-diamino-9g5 -azaheptadecane. A solution of 200 g of 1,17-diamino-9-azaheptadekan in 30 g of water is stirred and heated to b. Then, 850 g of a 30% solution of O-methylthiourea acetate is added. After stirring at 600 ° C for 5 hours, the reaction mixture is neutralized with 30 g of acetic acid. The resulting mixture has a guanying degree of 70%. After evaporation of the solvent and separation of the mixture, a) 98 g (33% of theoretical) of triacetate of 1,9,17-triguanidine .1,17-diamino-9-aaaeptedecane with mp 16; ° C: b) 54 g ( 23% of theoretical) triacetate of 1,9-diguanidized 1,17-diamino-9-azaheptadecane with mp 123 ° C; b) 43 g (18% of theory) of 1,17-diaguanidated 1,17-diamino-9-azaheptadecane triacetate with mp 140 ° C; J 31 g (14% of theory) of mono-guanidized triacetate with 1.17-diamino-9-azaheptadecane, m.p. 850s . H m i R 6. Preparation of guanidated triacetate 1,17-diamino-9-azaheptadecane. A solution of 200 g of 1,17-diamino-9-azaheptadekan in 30 g of water is stirred and heated to 70 s. Then 950 g of a 30% 5-methylisourea acetate solution are added. After stirring for 5 hours, the reaction mixture is neutralized with 30 g of acetic acid. The resulting mixture has a guanidation rate of 95%. After evaporation of the solvent and separation of the mixture, a) 103 g (40% of theoretical) of 1,9,17-triguanidated triacetate are obtained. 1,17-diamino-9-azaheptalecan with mp 5) 65 g (27% of theory) of 1,9-diguanide triacetate 1,17-diamino-9-azaheptadecane with mp 125 ° C; b) 34 g (14% of theory) of 1,17-diguanidized 1D7-diamino-9-azaheptadecane triacetate with mp 1400 ° C; g) 26 g (12% of theory) of mono-guanidized 1,17-diamino-9-azaheptadecane-triacetate with m.p. 87 Example 7. Preparation of a triacetate and guanidated 1,15-diamino-8-az anden tad exec but. 100 g of 1,15-diamino-8-azaheptadecane with partial neutralization is dissolved in 100 g of water containing 60 g of acetic acid. The mixture is heated to and within 4 hours, 160 g of a 50% aqueous solution of cyanamide is added. After stirring at the same temperature for 2 hours, the mixture is neutralized with 25 g of acetic acid. The guanidation rate is 91%. After evaporation of the solvent and separation of the mixture, a: 182 g (72% of theoretical) of 1,8,15-triguanidated 1,15-diamino-8-azaheptadecane triacetate with mp. 151С; b) 30 g (13% of theory) of 1,8-diaguanidized 1,15-diamino-8-azaheptadecane triacetate with a mp. 112 ° Cj b} ilg (5% of theoretical) of 1,15-diguanidized 1,15-diamino-8-azaheptadecane with m.p. 130 ° C. Example 8. Obtaining guanidated triacetate 1,19-diamino-10-azanonedecane. 200 g of 1,19-diamino-10-azanonedecane are dissolved in 80 g of ethylene glycol and 90 g of acetic acid. The mixture is heated to 70 ° C and 185 g of a 50% -th 8th aqueous solution of cyanamide are added over 3 hours, followed by aging for 4 hours. Then 30 g of acetic acid is neutralized. The guanidation rate is 81%. After evaporation of the solvents and separation of the product mixture, a) 157 g (64% of theoretical) of 1,10,19-triaguanidized 1,19-diamino-10-azanonadecane triacetate with mp. 166 ° C; 5) 40 g of fl7% of theoretical) triacetate of 1,10-diguanidized 1,19-diamino-10-azanonedecane with mp .. 128 ° C; B) 21 g (10% of theoretical) of 1,19-diganidated 1,19-diamino-10-azanonedecan with m.p. 142 ° C; 2.) 13 g (5% of theoretical) of mono-guanidized 1,19-diamino-10-azanonadecane triacetate with m.p. 900s Example 9 illustrates the fungicidal activity of new compounds in comparison with the known. EXAMPLE 9: Experiments were carried out in accordance with the Gilthner method, which consists in the following: infected seed, untreated or treated with the active substance, is grown with wet brick, gravel plates at 13-14 ° C and 80% relative humidity . The tests are carried out for 1 month, after which the degree of fungicidal activity is determined in percent of the control, i.e. determines the percentage of unaffected plants from treated seeds relative to the results when using untreated seeds. In each experiment 100 grains were consumed. Infected with the fungus Drechslera gramlneum wheat. The treatment is carried out by intensive mixing of the seeds with 2 ml / kg of a liquid preparation containing the specified active ingredient in a mixture of water and ethylene glycol (60:40). Then the seeds are left in contact with the drug for 24 hours before pro. The table shows the actual concentration of the activity. a) 4,6 A mixture of products 6) 2,8 8,0 tov cf), b) and d) b) 0.6 of example 3 1 D7-diguanidino-9-azagep tadecane (known) Formula and; master Method for producing guanidated acet aliphatic amines of the general formula I X-KYYA-NY-g H-X X where R is hexamethylene, heptamethylene, octamethylene, nonamethylene; X is a hydrogen or carboxamidine group, and at least one radical X means a carboxamidine group, 0 tl and h and with the fact that, aliphatic polyamine common formula - NHR - NHj where R is the above value, or a mixture with an aliphatic polyamine of the general formula Ml H, j, NR — NHR — NHj where R is the above value, different from the radical R in formula II, is reacted with cyanamide or O-or S-methyl urea to a guanidation level of 70-95%. I Sources of information taken into account in the examination 1. UK patent W1294443, cl. C 2 C, published, 1972.
    权利要求:
    Claims (1)
    [1]
    The table shows the active substances, their concentration and fungicidal activity.
    Active substance The concentration of the active substance in the tool, weight. % Fungicidal activity,% of control A mixture of products ci), b) and d) of example 3 a) 4.65) 2.8 8.05) 0.6 91 1,17-diguanidino-9-azaheptadecane (known) 10 73 Claim _A method of producing acetate salts of guanidinated aliphatic polyamines of the general formula I X-HHfc-NR-NH-X.
    where R is hexamethylene, heptamethylene, octamethylene, nonamethylene;
    X is hydrogen or a carboxamidine group, and at least one radical with X means a carboxamidine group, characterized in that, an aliphatic polyamine of the general formula !!
    NR - NHR - NH 2 where R is the above value, or a mixture thereof with an aliphatic polyamine of the general formula II |
    H a NR - NHR - NHj where R is the above value, different from the value of the radical R in formula II, is reacted with cyanamide or O- or S-methylisourea to a degree of guanidation of 70-95%.
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    同族专利:
    公开号 | 公开日
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    AU505423B2|1979-11-22|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE466879C|1925-08-04|1928-10-17|Schering Kahlbaum Ag|Process for the preparation of aminoguanidines|
    US2325586A|1940-03-21|1943-08-03|Du Pont|Polymeric guanidines and process for preparing the same|
    GB1114155A|1964-08-24|1968-05-15|Evans Medical Ltd|Guanidino derivatives|SE425043B|1977-05-10|1982-08-30|Kenogard Ab|FUNGICID COMPOSITION, PREFERRED FOR USE AS A THREE PROTECTIVE, CONTAINING AT LEAST ONE QUARTER OF AMMONIUM SUBSTANCE IN MIXING WITH AN AMINE COMPONENT|
    DE2952167A1|1979-12-22|1981-07-02|Hoechst Ag, 6230 Frankfurt|NEW GUANIDINIUM COMPOUNDS, METHOD FOR THE PRODUCTION AND USE THEREOF AS A MICROBIOCIDE AGENT|
    JPH027564B2|1984-02-24|1990-02-19|Dainippon Ink & Chemicals|
    JPS60160903U|1984-03-30|1985-10-25|
    US5753714A|1987-02-03|1998-05-19|Merrell Pharmaceuticals Inc.|Polyamine derivatives|
    DE4001117A1|1990-01-17|1991-07-18|Bayer Ag|Fungicidal drug combinations|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    SE7511852A|SE417569B|1975-10-22|1975-10-22|Certain stated mixtures of guanidated aliphatic polyamines, or their acid addition salts, for use as pesticides and antimicrobial agents|
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