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العنوان
Synthesis Of Some Amide And Phenoxy Derivatives And Their Biological Activity /
المؤلف
Mahmoud, Hemdan Ibrahem.
هيئة الاعداد
باحث / Hemdan Ibrahem Mahmoud
مشرف / A. H. El-Sayed
مشرف / S. M. Abd El-Kader
مشرف / E. A. El-Malt.
الموضوع
Agricultural chemistry. Biochemistry.
تاريخ النشر
2000.
عدد الصفحات
90 p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الزراعية والعلوم البيولوجية (المتنوعة)
تاريخ الإجازة
1/1/2000
مكان الإجازة
جامعة المنيا - كلية الزراعة - Agriculture BioChemistry
الفهرس
Only 14 pages are availabe for public view

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Abstract

Two different groups of organic compounds belonging to different classes were prepared according to the available methods.
With the aim of developing new compounds contain both of phenoxy and amide groups together in their skeletons in intent to possess a broad biological effects, six novel compounds of the [N-(substituted methyllphenyl) ]-carbamoylmethylene-sub stituted-methy 1- phenoxide derivatives (6-11) were synthesized. Also, four compounds of Schiff base, the 44Hydroxy-3-methoxy-benzylidene derivatives (18-21), were also synthesized.
In the present study, to evaluate the bacteriological efficiency of the new synthesized compounds, three microorganisms, one of useful bacteria, Sarcina urea, which fix the nitrogen in the soil asymbiotically, one pathogenic bacteria, Staphylococcus aureus, and one of the useful yeast, Saccharomyces cerevisiea, which use for the industrial fermentation processes, were used.
5.1- The Carbamoylmethylene derivatives:
ill The synthesis mechanism of carbamoylmethylene derivatives involves a nucleophilic backside attack of the phenolic ion (substituted-phenol derivatives) on the alkyl halide ([N-(substituted methylphenyl)]]carbamoyl methylene chloride).
o [N-(2-methylphenyl)]-carbamoylmethylene chloride (1) and [N-(4-
methylphenyl)]-carbamoylmethylene chloride (2) were prepared by the
reaction of both 2-methylaniline and 3-methylaniline, respectively, with a-chloroacetyl cWoride.
ill [N-(2-methylphenyl)]-carbamoylmethylene-2-methyl-phenoxide (6) was prepared by the reaction of [N-(2-methylphenyl)]-carbamoylmethylene chloride (1) and 2-methyl-phenol (3) in the presence of potassium polyethylene glycolate. Similarlly, and under the same conditions, [Nmethylphenyl)]-carbamoylmethylene-3-methyl-phenoxide (7) was prepared by the reaction of 3-methyl-phenol (4) and [Nmethylphenyl)]-carbamoylmethylene chloride (1); [Ncarbamoylmethylene-4-methyl-phenoxide (8) by the reaction of [Nmethylphenyl)]-carbamoylmethylene chloride (1) and 4-methyl-phenol (5); [N-( 4-methylphenyl) ]-carbamoylmethylene- 2-methy l-phenoxide (9) by the reaction of 2-methyl-phenol (3) and [Ncarbamoyl methylene chloride (2); [N-( 4carbamoylmethylene-3-methyl-phenoxide (10) by the reaction of [N-( 44methylphenyl)]-carbamoylmethylene cWoride (2) and 3-methyl-phenol (4); [N-( 4-methylphenyl)]-carbamoylmethylene-4-methyl-phenoxide (11) by the reaction of 4-methyl-phenol (5) and [Ncarbamoyl methylene cWoride (2).
ill All compounds were purified by crystallization and recrystallization resulted in pure crystals. The physical constants, melting points, R[values in different solvents systems were recorded. Both ofIR spectrum and MS spectrum of these compounds were in full agreement with their assigned chemical structures.
ill In respect to the asymbiotic nitrogen fixers bacteria, the survival of the Sarcina urea (Gram positive bacteria) was activated by all of the synthesized carbamoylmethylene phenoxide derivatives. The highly activation was carried out by [N3 - methyl-phenoxide (7), [N -(2-methy lphenyl) ]-carbamoy Imethylene-4-
® Both of 4-Hydroxy-3-methoxy-benzylidene-phenylamine (18) and 44Hydroxy-3-methoxy-benzylidene-imino-phenylamine (21), which have no methyl group at ortho- or para-position were activated the proliferation of the Sarcina urea.
ill The 4-Hydroxy-3-methoxy-benzylidene-4-methyl-phenylamine (20) and 44Hydroxy-3-methoxy-benzylidene-2-methyl-phenylamine (19) were also activated the Sarcina urea but in ratio less than the two latter compounds.
The Conc1ousion:
Summarizing the considered results of these new compounds. It could be conclude that it could be use of [Ncarbamoylmethylene-3-methyl-phenoxide (7), [Ncarbamoylmethylene-4-methyl-phenoxide (8) and [Ncarbamoylmethylene-2-methyl-phenoxide (9) to accelerate the stimulation of the nitrogen fixers bacteria group in its growth media. Also, it could be mix these compounds with the inoculum which mixed with the seeds before planting. Both of the [N3-methyl-phenoxide (7) and [N-( 42-methyl-phenoxide. (9) could be used to inhanced the propagation of the Saccharomyces cerevisiea. In addition, 4benzylidene-2-methyl-phenylamine (19) and 4benzylidene-4-methyl-phenylamine (20), could be used to stop the fermentation process in some maniefactor systems required that. The compounds [N -(2-methy1phenyl)] -earbamoylmethylene- 2-methyl-phenoxide (6), [N-(4-methylphenyl)]-earbamoylmethylene-3-methyl-phenoxide (10), 44Hydroxy-3-methoxy-benzylidene-2-methyl-phenylamine (19) and 43-methoxy-benzylidene-imino-phenylamine (21) could be surved as a germicidal agent against the pathogenic bacteria Staphylococcus aureus.