Synthesis method of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron and antibacterial application

A technology for hydrogenating nobyl and gemini quaternary ammonium, applied in the fields of application, botany 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 The effect of high purity, mild conditions and easy control, and simple equipment

Active Publication Date: 2019-12-20
JIANGXI AGRICULTURAL UNIVERSITY
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  • 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 pe

Method used

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  • Synthesis method of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron and antibacterial application
  • Synthesis method of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron and antibacterial application
  • Synthesis method of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron and antibacterial application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 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 / 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 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, 212-CH3), 3.543 (4H, m, 211-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,25-CH),1.150(6H,s,29-CH3),0.988(6H,s,28-CH3),0.830(2H,d,J=9.6Hz,27-CH ); δC(CDCl3): 38.585(C-1), 46.286(C-2), 22.328(C-3), 26.268(C-4)...

Embodiment 2

[0020] In a 150mL ground-necked Erlenmeyer flask, add 55mmoL of nobyldimethylamine, 25mmoL of 1,4-dibromobutane, 50mL of methanol / ethanol / isopropanol / methyl acetate / ethyl acetate / acetone / butanone / acetonitrile, put in a stirring bar, install a spherical condenser, place on a magnetic heating stirrer for stirring and reflux, stop heating after 24 hours, cool to 10°C to obtain crystals, filter the crystals, and suction filter with cold petroleum ether To dryness, vacuum-dry to obtain tetramethylene-1,4-bis(hydrogenated dimethyl ammonium bromide) (1-4-1BB) finished product. White fine columnar crystals, the yield is 87%, m.p.263.7-265.5℃. NMR,δH(CDCl3):3.817(4H,m,212-CH2),3.045(4H,m,211-CH2),3.240(12H,s,4α-CH3),2.288(2H,m,22-CH2) ,2.041~1.765[20H,m,2(7-CH,10-CH2,5-CH,1-CH,4-CH2,3-CH),213-CH2], 1.427(2H,m,23-CH ),1.147(6H,s,9-CH3),0.975(6H,s,28-CH3),0.821(2H,d,J=9.6Hz, 27-CH); δC(CDCl3):37.782(C-1 ), 45.339(C-2), 21.363(C-3), 25.80(C-4), 40.859(C-5), 38.047(C-6), 29.430(C-7), ...

Embodiment 3

[0022] In a 150mL ground-necked Erlenmeyer flask, add 55mmoL of nobyldimethylamine, 25mmoL of 1,5-dibromopentane, 50mL of methanol / ethanol / isopropanol / methyl acetate / ethyl acetate / acetone / butanone / acetonitrile, put in a stirring bar, install a spherical condenser, place on a magnetic heating stirrer for stirring and reflux, stop heating after 24 hours, cool to 10°C to obtain crystals, filter the crystals, and suction filter with cold petroleum ether To dryness, vacuum-dry to obtain pentamethylene-1,5-bis(hydrogenated dimethyl ammonium bromide) (1-5-1BB) finished product. White crystals, yield 85%, m.p.239.1-241.7°C. NMR, δH(CDCl3): 3.365~3.280(8H, m, 211-CH2, 212-CH2), 3.051(12H, s, 4α-CH3), 2.329(2H, m, 22-CH2), 1.934~1.826[ 12H, m,2(7-CH,10-CH2,5-CH,3-CH)],1.719(8H,m,24-CH2,213-CH2),1.475(2H,m,2 3-CH) ,1.289(2H,m,14-CH2),1.817(6H,s,29-CH3),1.036(6H,s,28-CH3),0.859(2H,d,J=9.6Hz,27-CH); δC(CDCl3): 37.924(C-1), 45.420(C-2), 21.731(C-3), 25.908(C-4), 40.977(C-5), 38.116(C-6...

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Abstract

The invention discloses a synthesis method of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron and antibacterial application. The synthesis method comprises the following steps:performing heating reflux on hydrogenated nopyl-containing tertiary amine and alpha-omega-dibromohaloalkane as raw materials in an organic solvent, and performing cooling, crystallization, filtering,washing and vacuum drying after reactions, so as to obtain seven types of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron. When the mass concentration of a medicine liquid is500mg/L, the seven types of hydrogenated nopyl-containing symmetric genini quaternary ammonium iron have good inhibition functions on ten plant pathogenic fungi, particularly the inhibition rates uponfusarium proliferatum, alternaria kikuchiana, ceratosphaeria phyllostachydis, sphaeropsis sapinea and fusicoccum aesculi are greatly higher than that of chlorothalonil upon the plant pathogenic fungi, and the inhibition rates of the hydrogenated nopyl-containing symmetric genini quaternary ammonium iron upon thanatephorus cucumeris is 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 antibacterial application of symmetrical Gemini quaternary ammonium ferric ammonium containing hydrogenated nob 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...

Claims

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Application Information

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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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