CN105017036B - There is the 2-(virtue aminoethylamino of bactericidal activity) benzyl alcohol compounds and application thereof - Google Patents
There is the 2-(virtue aminoethylamino of bactericidal activity) benzyl alcohol compounds and application thereof Download PDFInfo
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Abstract
The invention discloses a kind of 2 (virtue aminoethylamino) benzyl alcohol compounds with bactericidal activity, its structure is as shown in formula I, and in formula I, R is H, or o CH3, or m CH3, or p CH3, or m CH3O, or p CH3O, or p Cl.Benzyl alcohol compounds has preferable bactericidal activity to the present invention 2 (virtue aminoethylamino) to the disease of crops, and its synthetic material is easy to get, and synthetic method is simple.
Description
Technical field
The invention belongs to pesticide field, be specifically related to a class and there is the novel 2-(virtue aminoethylamino of bactericidal activity) benzene
Methanol compounds.
Background technology
O-benzyl alcohol is a kind of very important organic synthesis intermediate, can be used to synthesize Schiff alkali, a class tool
There is the material of multi-functional character, not only can form coordination compound with metal, and there is good biological activity, as antibacterial and anticancer
Activity etc.；O-benzyl alcohol reacts with 5-hydroxyl-2,3-Dihydrobenzofuranes-6-formaldehyde can generate 5-hydroxyl-6-(2-hydroxyl first
Base) amino methyl-2,3-Dihydrobenzofuranes, this compounds can be as medicines such as anti-tumor agent, hiv protease preparations
Intermediate raw material；O-benzyl alcohol and β-chloro-n-methyl phenethylamine react and can synthesize β [(O-hydroxymethyl)-anilino-]-N-
Methylphenethylamine, the important source material of a kind of synthesizing hydrogenated isoquinolin alkali；O-benzyl alcohol may further be used to synthesize 3,1-benzo
Piperazine compounds and 3,1-benzoxazoles ketone compounds, these compounds have biological activity widely.Recently, we study
O-benzyl alcohol and the alkylated reaction of acetyl bromide arylamine, synthesized aryl amine and replaced acetanilide compounds, Yi Zhonghe
Become the important intermediate of 3,1-benzimidazole dihydrochloride compounds.When we use LiAlH4Synthesized aryl amine is replaced acetanilide
Compounds carry out reducing generate the 2-(virtue aminoethylamino that a class formation is novel) benzyl alcohol compounds, and sterilize
Active testing shows that this compounds has preferable bactericidal activity.But document is to this 2-(virtue aminoethylamino) benzene first
Alcohol compound is almost without report.Therefore, the present invention provides a class to have the novel 2-(virtue amino-ethyl of preferable bactericidal activity
Amino) benzyl alcohol compounds.
Summary of the invention
It is an object of the invention to provide a kind of novel 2-(virtue aminoethylamino with bactericidal activity) benzyl alcohol class
Compound.
Novel 2-(virtue aminoethylamino) benzyl alcohol compounds, its structure is as shown in formula I:
In formula I, R is-H, or o-CH3, or m-CH3, or p-CH3, or m-CH3O, or p-CH3O, or p-Cl.
The described 2-(virtue aminoethylamino with bactericidal activity) application in terms of sterilization of the benzyl alcohol compounds.
It being experimentally confirmed the above-mentioned novel 2-(virtue aminoethylamino of the present invention) benzyl alcohol compounds is to crops
Disease there is preferable bactericidal activity, and its synthetic material is easy to get, and synthetic method is simple.
Detailed description of the invention:
Use vitro method, to 2-((2-(phenyl amino) ethyl) amino) benzyl alcohol, 2-((2-(2-Tolylamino) second
Base) amino) benzyl alcohol, 2-((2-(3-Tolylamino) ethyl) amino) benzyl alcohol, 2-((2-(4-Tolylamino) ethyl)
Amino) benzyl alcohol, 2-((2-(3-methoxyphenyl) amino) ethyl) amino) benzyl alcohol, 2-((2-(4-methoxyphenyl) ammonia
Base) ethyl) amino) benzyl alcohol, 2-((2-(4-chlorphenyl) amino) ethyl) amino) benzyl alcohol carried out bactericidal activity test.
With fusarium graminearum, botrytis cinerea pers, P. capsici, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and
The material to be tested that Pyricularia oryzae is tested as bactericidal activity, is dissolved in reagent agent in acetone, then uses 200 g/mL
Sorporl-144 emulsifying agent is diluted to 500 g/mL medicinal liquids.Under aseptic operating condition, draw the chemical combination of 1mL with liquid-transfering gun
Thing solution adds in sterilized plate, then adds the sterilizing PDA of 9 mL with pipet and cultivate based in plate, and mixing is made
The pastille flat board of respective concentration.By cultured pathogen, aseptically with the sterilizing card punch of a diameter of 4 mm, from bacterium
The edge that falls cuts bacterium cake, after culture medium solidifying, with inoculator by pure culture biscuits involvng inoculation in pastille flat board central authorities, is placed in preference temperature
Incubator is cultivated.Blank is done with not adding medicine.Each process is cultivated in 24 ± 1 DEG C of incubators, observes after 72 hours
And measuring colony diameter, it is each once that each bacterium colony decussation method vertically measures diameter, takes its meansigma methods.Growth inhibition ratio
(%)=(comparison colony diameter-process colony diameter) × 100/ (comparison colony diameter-4 mm).Drug concentration is 25 μ g/mL
(when wherein material to be tested is Pyricularia oryzae, concentration is 50 μ g/mL).Bactericidal activity test result is shown in Table one.
Knowable to table one, 2-(virtue aminoethylamino) benzyl alcohol has preferable activity to for examination pathogenic bacteria.Wherein, target chemical combination
Thing is the highest to the suppression ratio of P. capsici, 2-((2-(4-methoxyphenyl) amino) ethyl) amino) benzyl alcohol is to Fructus Capsici
The suppression ratio of phytophthora pathogenic bacteria reaches 73.0%.Secondly, target compound also has preferable inhibitory activity, compound to hyphal cluster germ
2-((2-(4-chlorphenyl) amino) ethyl) amino) inhibitory activity of benzyl alcohol is 68.1%.Again, target compound is to rice blast
Pathogenic bacteria also has preferable inhibitory activity, compound 2-((2-(4-chlorphenyl) amino) ethyl) amino) benzyl alcohol suppression live
Property is 52.9%.
In order to be more fully understood that the present invention, be now given and prepare 2-(virtue aminoethylamino) example of benzyl alcohol compound.
The synthesis of example 1:2-((2-(phenyl amino) ethyl) amino) benzyl alcohol.
To 50 the mono-neck round-bottom flasks of mL add 2-((2-hydroxymethyl phenyl) amino)-phenyl acetanilide,Phenacetylanilines (0.508 g,
2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g , 9.2
Mmol), 24 h it are heated to reflux.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL15% subsequently
Sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate ethyl acetate
After extraction, organic solvent anhydrous sodium sulfate is dried.Pale yellow oil matter, productivity is obtained through column chromatography for separation after concentrating under reduced pressure
80.4 %。1H NMR (CDCl3, 500 MHz) δ: 3.42(s, 4H, -CH2-NH-), 4.62(s, 2H, -CH2OH),
6.65(d, 2H, J=8.0Hz, HAr), 6.69~6.75(m, 3H, HAr), 7.06(d, 1H, J=7.5Hz, HAr),
7.18~7.26(m, 3H, HAr). 13C NMR (CDCl3, 125 MHz) δ: 42.90, 43.06, 64.74,
110.91, 113.14(2C), 117.03, 117.80, 124.78, 129.38, 129.41(2C), 129.74,
147.42, 148.09. IR (KBr, ν/cm-1): 750, 994, 1075, 1135, 1219, 1258, 1317,
1463, 1505, 1603, 2864, 2921, 3047, 3395.
Example 2:2-((2-(2-Tolylamino) ethyl) amino) synthesis of benzyl alcohol.
2-((2-hydroxymethyl phenyl is added to the 50 mono-neck round-bottom flasks of mL) amino)-N-(2-tolyl) acetamide
(0.536 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL subsequently
15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid second
After ester extraction, organic solvent anhydrous sodium sulfate is dried.Faint yellow solid, productivity must be obtained through column chromatography for separation after concentrating under reduced pressure
95.30%.Mp:77.6-77.9 ° of C.1H NMR (CDCl3, 500 MHz) δ: 2.05(s, 3H, -CH3), 3.41(s,
4H, -CH2-NH-), 4.57(s, 2H, -CH2OH), 6.59~6.63(m, 3H, HAr), 6.67(d, 1H, J=
8.0Hz, HAr), 7.00(d, 2H, J=7.0Hz, HAr), 7.06(t, 1H, J=7.5Hz, HAr), 7.17(1H, J
=7.0Hz, HAr). 13C NMR (CDCl3, 125 MHz) δ: 17.62, 42.79, 43.04, 64.87, 109.94,
110.91, 117.06, 117.42, 122.53, 124.79, 127.23, 129.36, 129.81, 130.32,
145.98, 147.50. IR (KBr, ν/cm-1): 751, 930, 941, 1048, 1134, 1262, 1311, 1443,
1465, 1509, 1584, 1604, 2855, 3040, 3394.
Example 3:2-((2-(3-Tolylamino) ethyl) amino) synthesis of benzyl alcohol.
2-((2-hydroxymethyl phenyl is added to the 50 mono-neck round-bottom flasks of mL) amino)-N-(3-tolyl) acetamide
(0.536 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL subsequently
15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid second
After ester extraction, organic solvent anhydrous sodium sulfate is dried.Faint yellow solid, productivity is obtained through column chromatography for separation after concentrating under reduced pressure
91.1%.Mp:55.1-58.3 ° of C. 1H NMR (CDCl3, 500 MHz) δ: 2.26(s, 3H, -CH3), 3.40(s,
4H, -CH2-NH-), 4.61(s, 2H, -CH2OH), 6.45(s, 2H, HAr), 6.54(d, 1H, J=7.5Hz,
HAr), 6.67~6.72(m, 2H, HAr), 7.04~7.08(m, 2H, HAr), 7.22(t, 1H, J=8.0Hz,
HAr). 13C NMR (CDCl3, 125 MHz) δ: 21.74, 43.01, 43.08, 64.82, 110.33, 110.91,
113.91, 117.01, 118.75, 129.28, 129.39, 129.78, 139.22, 147.46, 148.15. IR
(KBr, ν/cm-1): 750, 850, 1000, 1074, 1137, 1175, 1254, 1322, 1467, 1497, 1587,
1606, 2856, 2923, 3347, 3387.
Example 4:2-((2-(4-Tolylamino) ethyl) amino) synthesis of benzyl alcohol.
2-((2-hydroxymethyl phenyl is added to the 50 mono-neck round-bottom flasks of mL) amino)-N-(4-tolyl) acetamide
(0.536 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL subsequently
15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid second
After ester extraction, organic solvent anhydrous sodium sulfate is dried.Faint yellow solid, productivity 94.7 is obtained through column chromatography for separation after concentrating under reduced pressure
%, mp:69.1-72.5 ° of C.1H NMR (CDCl3, 500 MHz) δ: 2.24(s, 3H, -CH3), 3.41(s, 4H, -
CH2-NH-), 4.64(s, 2H, -CH2OH), 6.57(d, 2H, J=8.5Hz, HAr), 6.67~6.73(m, 2H,
HAr), 6.99(d, 2H, J=8.0Hz, HAr), 7.06(d, 1H, J=7.5Hz, HAr), 7.21~7.25(m, 1H,
HAr). 13C NMR (CDCl3, 125 MHz) δ: 20.50, 42.93, 43.48, 64.73, 110.93, 113.40
(2C), 116.99, 124.77, 127.12, 129.36, 129.73, 129.88(2C), 145.78, 147.44. IR
(KBr, ν/cm-1): 737, 809, 996, 1121, 1216, 1244, 1291, 1311, 1452, 1489, 1516,
1589, 1609, 2854, 1921, 3273, 3401.
Example 5:2-((2-(3-methoxyphenyl) amino) ethyl) amino) synthesis of benzyl alcohol.
2-((2-hydroxymethyl phenyl is added to the 50 mono-neck round-bottom flasks of mL) amino)-N-(3-methoxyphenyl) acetamide
(0.568 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL subsequently
15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid second
After ester extraction, organic solvent anhydrous sodium sulfate is dried.Obtain the grease of brown color, productivity through column chromatography for separation after concentrating under reduced pressure
82.3%. 1H NMR (CDCl3, 500 MHz) δ: 3.41(s, 4H, -CH2-NH-), 3.75(s, 3H, -CH3),
4.63(s, 2H, -CH2OH), 6.19(s, 1H, HAr), 6.25~6.29(m, 2H, HAr), 6.67~6.72(m,
2H, HAr), 7.05~7.09(m, 2H, HAr), 7.21~7.25(m, 1H, HAr). 13C NMR (CDCl3, 125
MHz) δ: 42.95, 43.10, 55.22, 64.88, 99.07, 102.89, 106.26, 110.91, 117.06,
124.76, 129.41, 129.81, 130.17, 147.46, 149.55, 160.93. IR (KBr, ν/cm-1): 750,
827, 991, 1046, 1162, 1209, 1265, 1310, 1462, 1515, 1606, 2861, 2929, 3397.
Example 6:2-((2-(4-methoxyphenyl) amino) ethyl) amino) synthesis of benzyl alcohol.
2-((2-hydroxymethyl phenyl is added to the 50 mono-neck round-bottom flasks of mL) amino)-N-(4-methoxyphenyl) acetamide
(0.568 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 mL subsequently
15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid second
After ester extraction, organic solvent anhydrous sodium sulfate is dried.Brown oil, productivity 91.8 is obtained through column chromatography for separation after concentrating under reduced pressure
%. 1H NMR (CDCl3, 500 MHz) δ: 3.30(d, 2H, J=5.0Hz, -CH2-NH-), 3.33(d, 2H, J=
5.0Hz, -CH2-NH-), 3.75(s, 3H, -CH3), 4.01(s, 2H, -NH-CH2-), 4.54(s, 2H, -
CH2OH), 6.61(d, 2H, J=9.0Hz, HAr), 6.70~6.74(m, 2H, HAr), 6.80(d, 2H, J=
9.0Hz, HAr), 7.02(d, 1H, J=7.0Hz, HAr), 7.26(t, 1H, J=8.0Hz, HAr). 13C NMR
(CDCl3, 125 MHz) δ: 42.99, 44.19, 55.92, 64.80, 110.95, 114.65(2C), 115.01
(2C), 117.01, 124.78, 129.39, 129.77, 142.21, 147.48, 152.47. IR (KBr, ν/cm-1): 746, 825, 994, 1035, 1238, 1285, 1311, 1443, 1465, 1509, 1584, 1607,
2832, 2904, 3276, 3374, 3401.
Example 7:2-((2-(4-chlorphenyl) amino) ethyl) amino) synthesis of benzyl alcohol.
N-(4-chlorphenyl is added to the 50 mono-neck round-bottom flasks of mL)-2-((2-hydroxymethyl phenyl) amino) acetamides
(0.580 g, 2 mmol), the 30 anhydrous THF of mL make solvent, under the conditions of ice-water bath, are dividedly in some parts LiAlH4 (0.349 g ,
9.2 mmol), it is heated to reflux 24 h.After the cooling of ice-water bath condition, it is slowly added to 0.5 mL distilled water, adds 1.0 subsequently
ML15% sodium hydroxide solution and 1.5 mL distilled water.After stirring 2 ~ 3min, sucking filtration, filter cake ethyl acetate washing, filtrate acetic acid
After ethyl ester extraction, organic solvent anhydrous sodium sulfate is dried.Pale yellow oil, productivity is obtained through column chromatography for separation after concentrating under reduced pressure
79.5%. 1H NMR (CDCl3, 500 MHz) δ: 3.37(d, 2H, J=5.0Hz, -CH2-NH-), 3.40(d, 2H,
J=6.0Hz, -CH2-NH-), 4.60(s, 2H, -CH2OH), 6.56(d, 2H, J=8.5Hz, HAr), 6.73~6.77
(m, 2H, HAr), 7.06(d, 1H, J=7.5Hz, HAr), 7.15(d, 2H, J=9.0Hz, HAr), 7.29(t,
1H, J=7.5Hz, HAr). 13C NMR (CDCl3, 125 MHz) δ: 42.62, 43.10, 64.50, 110.92,
114.17(2C), 117.16, 122.21, 124.77, 129.13(2C), 129.38, 129.71, 146.59,
147.20. IR (KBr, ν/cm-1): 750, 815, 991, 1090, 1126, 1177, 1260, 1311, 1459,
1496, 1600, 2868, 2922, 3417。
Claims (2)
1. there is the 2-(virtue aminoethylamino of bactericidal activity) a benzyl alcohol compound, its structure is as shown in formula I:
In formula I, R is-H, or o-CH3, or m-CH3, or p-CH3, or m-CH3O, or p-CH3O, or p-Cl.
2. the 2-(virtue aminoethylamino with bactericidal activity described in claim 1) benzyl alcohol compound is to crops
Application in terms of disease sterilization.
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