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Synthesis method and antibacterial application of symmetrical gemini quaternary ammonium salt containing hydrogenated nob group

A Gemini quaternary ammonium salt, hydrogenated nob base technology, applied in the fields of application, botanical equipment and methods, fungicides, etc., can solve the problems of large pesticide residues, loss of agricultural, forestry and animal husbandry production, environmental pollution, etc., and achieve product yield and high purity, mild and easy-to-control conditions, and simple equipment

Active Publication Date: 2020-11-13
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Plant pathogenic bacteria not only endanger the normal growth of crops and cause heavy losses to agriculture, forestry and animal husbandry, but also cause a series of foodborne diseases, which seriously threaten the life and health of humans and animals. However, plant pathogenic bacteria are extremely resistant to general chemical pesticides and fungicides. Moreover, a large amount of chemical fungicides is likely to cause problems such as large pesticide residues in plants and environmental pollution.
But there is no research on the gemini quaternary ammonium salts containing hydrogenated nobyl groups and their synthetic methods and antibacterial applications at present.

Method used

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  • Synthesis method and antibacterial application of symmetrical gemini quaternary ammonium salt containing hydrogenated nob group
  • Synthesis method and antibacterial application of symmetrical gemini quaternary ammonium salt containing hydrogenated nob group
  • Synthesis method and antibacterial application of symmetrical gemini quaternary ammonium salt containing hydrogenated nob group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 150mL ground-necked Erlenmeyer flask, add 55mmoL of nobyldimethylamine, 25mmoL of 1,3-dibromopropane, 50mL of methanol / ethanol / isopropanol / methyl acetate / ethyl acetate / acetone / butanone / acetonitrile , put in a stirrer, install a spherical condenser, place it on a magnetic heating stirrer for stirring and reflux, stop heating after 24 hours, cool to 10°C, and obtain crystals, filter the crystals, and filter them with cold petroleum ether to dryness , and vacuum-dried to obtain trimethylene-1,3-bis(hydrogenated dimethyl ammonium bromide) (1-3-1BB) finished product. White fine columnar crystals, the yield is 81%, m.p.245.7-247.3℃. NMR, δH (CDCl3): 3.748 (4H, t, J = 8Hz, 2 12-CH3), 3.543 (4H, m, 2 11-CH2), 3.326 (12H, s, 4α-CH3), 2.359 (2H, m,2 2-CH),2.292(2H,m,13-CH2),2.018~1.698[6H,m,2(7-CH,10-CH2,5-CH,1-CH,4-CH2,3 -CH)], 1.434 (2H, m, 2 5-CH), 1.150 (6H, s, 2 9-CH3), 0.988 (6H, s, 2 8-CH3), 0.830 (2H, d, J = 9.6 Hz,2 7-CH); δC(CDCl3):38.585(C-1),46.286(C-2),22.328...

Embodiment 2

[0019] In a 150mL ground-mouth Erlenmeyer flask, add 55mmoL of nobyldimethylamine, 25mmoL of 1,4-dibromobutane, 50mL of methanol / ethanol / isopropanol / methyl acetate / ethyl acetate / acetone / butanone / Put acetonitrile into a stirring bar, install a spherical condenser, place it on a magnetic heating stirrer for stirring and reflux, stop heating after 24 hours, cool to 10°C, and obtain crystals, filter the crystals, and suction filter with cold petroleum ether to Dry and vacuum-dry to obtain the finished product of tetramethylene-1,4-bis(hydrogenated dimethylammonium bromide) (1-4-1BB). White fine columnar crystals, the yield is 87%, m.p.263.7-265.5℃. NMR, δH (CDCl3): 3.817 (4H, m, 2 12-CH2), 3.045 (4H, m, 2 11-CH2), 3.240 (12H, s, 4α-CH3), 2.288 (2H, m, 2 2 -CH2),2.041~1.765[20H,m,2(7-CH,10-CH2,5-CH,1-CH,4-CH2,3-CH),2 13-CH2],1.427(2H,m ,23-CH),1.147(6H,s,9-CH3),0.975(6H,s,2 8-CH3),0.821(2H,d,J=9.6Hz,2 7-CH); δC(CDCl3) :37.782(C-1),45.339(C-2),21.363(C-3),25.80(C-4),40.859(C-5),...

Embodiment 3

[0021] In a 150mL ground-mouth Erlenmeyer flask, add 55mmoL of nobyldimethylamine, 25mmoL of 1,5-dibromopentane, 50mL of methanol / ethanol / isopropanol / methyl acetate / ethyl acetate / acetone / butanone / Put acetonitrile into a stirring bar, install a spherical condenser, place it on a magnetic heating stirrer for stirring and reflux, stop heating after 24 hours, cool to 10°C, and obtain crystals, filter the crystals, and suction filter with cold petroleum ether to Dry and vacuum-dry to obtain the finished product of pentamethylene-1,5-bis(hydrogenated dimethyl ammonium bromide) (1-5-1BB). White crystals, yield 85%, m.p.239.1-241.7°C. NMR, δH (CDCl3): 3.365~3.280 (8H, m, 2 11-CH2, 2 12-CH2), 3.051 (12H, s, 4α-CH3), 2.329 (2H, m, 2 2-CH2), 1.934 ~1.826[12H,m,2(7-CH,10-CH2,5-CH,3-CH)],1.719(8H,m,24-CH2,2 13-CH2),1.475(2H,m,2 3-CH), 1.289 (2H, m, 14-CH2), 1.817 (6H, s, 2 9-CH3), 1.036 (6H, s, 2 8-CH3), 0.859 (2H, d, J = 9.6Hz ,27-CH); δC(CDCl3):37.924(C-1),45.420(C-2),21.731(C-3),25....

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Abstract

The invention discloses a synthesis method and antibacterial application of a symmetrical gemini quaternary ammonium salt containing a hydrogenated nobyl group. The tertiary amine containing a hydrogenated nobyl group and α,ω-dibromohalogenated alkanes are used as raw materials and heated to reflux in an organic solvent to react After cooling, crystallization, filtration, washing, and vacuum drying, seven kinds of symmetrical gemini quaternary ammonium salts containing hydrogenated nobyl groups were obtained. At a liquid mass concentration of 500mg / L, seven kinds of quaternary ammonium salts containing hydrogenated nobyl groups have good inhibitory effects on ten kinds of plant pathogenic bacteria used, especially on Fusarium laminarum, Alternaria pears, Phyllostachys pubescens The inhibition rate of the fungus, pine blight fungus and Aescin sp. was much higher than that of chlorothalonil, and the inhibition rate of the rice sheath blight fungus was equivalent to that of chlorothalonil.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis of natural products, and in particular relates to a synthesis method and an antibacterial application of a symmetrical gemini quaternary ammonium salt containing a hydrogenated nobyl group. Background technique [0002] Plant pathogenic bacteria not only endanger the normal growth of crops and cause heavy losses to agriculture, forestry and animal husbandry, but also cause a series of foodborne diseases, which seriously threaten the life and health of humans and animals. However, plant pathogenic bacteria are extremely resistant to general chemical pesticides and fungicides. Moreover, a large amount of chemical fungicides is easily used to cause problems such as large pesticide residues in plants and environmental pollution. Quaternary ammonium compounds are a class of stable properties, with strong surface activity and bactericidal effect. The N,N-dimethyl(ethyl)-N-alkylhydrogenated n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/08C07C211/63A01N33/12A01P3/00
CPCA01N33/12C07C209/08C07C2602/42C07C211/63
Inventor 王宗德冯雪贞肖转泉范国荣陈尚钘廖圣良罗海贺璐王鹏司红燕秦金梦
Owner JIANGXI AGRICULTURAL UNIVERSITY
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