RU2292451C1 - Chemical compound for suppressing growth of sulphate-restoring bacteria - Google Patents

Abstract

FIELD: chemical composition, possible use as bactericide for suppressing growth of sulfate-restoring bacteria, possible use in oil industry during extraction of oils containing hydrogen sulfide, in particular, in system for utilization of wastewater, and also .

SUBSTANCE: invented chemical compound is 2-(4-pyridile)-3-pentil-6-bromium-8-nitrilquinoline of formula

, useable for suppressing growth of sulfate-restoring bacteria.

EFFECT: creation of new chemical compound, having increased bactericide ability for suppressing growth of sulfate restoring bacteria and low flow norm.

3 ex, 1 tbl

Description

The invention relates to new chemical compounds as a bactericide to inhibit the growth of sulfate-reducing bacteria and can be used in the oil industry for the extraction of oils containing hydrogen sulfide, in particular in a wastewater disposal system, as well as in industrial water recycling systems.

The closest analogue in structure and achieved effect is 4-aminopyridine [Gerasimenko A.A., Aleksandrov Y.I., Andreev I.N. and others. Protection against corrosion, aging and biodeterioration of machines, equipment and structures. Directory. T.1 / Ed. A.A. Gerasimenko. - M.: Mechanical Engineering, 1987. - 687 p.].

However, this compound is insoluble in water and to achieve the effect of suppressing the vital activity of microorganisms requires high consumption rates (0.5% concentration in an aggressive environment). The latter circumstance, combined with the need to use specific solvents, significantly limits the scope of 4-aminopyridine.

It is known the use of quinoline derivatives as bactericides: 6,7-heterocyclo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid [US Pat. calculation of Germany 1936393, C 07 a, AO61, 02/05/1970, Laboratore Roger Bellon. - M. Pesson, CA73 (15), 77079], 8-acyloxy-7-nitriloquinoline [US Pat. Layout of Germany 2005959, C 07 d, 08/06/1970, Recordati Industria Chimica e Farmaceutica s.a.s. - D. Nardi, E. Massarani, L. Degen, CA73 (15), 77076].

The disadvantage of these prototype bactericides is low efficiency in relation to sulfate-reducing bacteria.

The present invention is based on the task of creating a new chemical compound with a higher bactericidal ability to inhibit the growth of sulfate-reducing bacteria and a low consumption rate.

The problem is solved in that the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitriloquinoline of the following formula is used as a bactericide to inhibit the growth of sulfate-reducing bacteria:

The chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitriloquinoline is obtained by mixed condensation of 2-nitro-5-bromaniline with pyridin-4-aldehyde and heptanal. To a solution of 0.4 mmol RUCl ₃ (0.1 g) and 1.2 mmol PPh ₃ (0.3 g) in 1 ml of absolute benzene in an argon stream at 10 ° C, 1.2 mmol Et ₃ Al was added and stirred 10 minutes. The resulting catalyst solution was placed in a steel autoclave (V = 17 cm ³ ), where 20 mmol of 2-nitro-5-bromaniline, 21 mmol of pyridin-4-aldehyde, 21 mmol of heptanal and 6 ml of benzene were pre-charged. The autoclave was heated for 6 hours at 150 ° C with constant stirring, then cooled. The reaction mass was extracted three times with ether (3 × 50 ml), the combined extracts were dried over anhydrous MgSO ₄ . The precipitated crystals were recrystallized from benzene, filtered off and held in a desiccator. Received 5.6 g (yield 70%) of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline. This compound is a characteristic odor powder. Melting point T _pl. = 112 ° C.

PMR spectrum (δ, ppm): 0.9 t (3H, CH ₃ ); 1.35-1.85 m (6H, CH ₂ ); 2.9 t (2H, CH ₂ ); 7.39-7.62 m (4H, 4-Ru); 7.57 d; 7.88 d; 8.1 days

Found,%: C 56; H 5; N 11; About 8; Br 20.

C ₁₉ H ₁₈ N ₃ O ₂ Br. Calculated,%: C 57; H 4.5; About 10.5; N 8; Br 20. M ⁺ 400.

An analysis of the known technical solutions selected in the search process showed that in science and technology there is no object similar in terms of the claimed combination of features and advantages, which allows us to conclude that its criteria are “novelty” and “inventive step”.

Compliance with the criterion of "industrial applicability" is proved by the following specific examples.

In all examples, tests of the protective effect of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline were carried out in accordance with RD 39-0147103-350-89 "Evaluation of the bactericidal efficacy of reagents with respect to adhered cells of sulfate-reducing bacteria in laboratory tests "(Murzagildin ZG, Yudina EG, Sabirova A.Kh. - VNIISPTneft, 1989). The essence of the method consists in keeping samples of mild steel in an active culture of sulfate-reducing bacteria (SBB) with their subsequent treatment with a bactericide, aseptic transfer to culture vessels with a nutrient medium and determining the minimum lethal concentration of the reagent.

Example 1. With an initial amount of SVB equal to 10 ⁶ cells / ml, in the control experiment, an increase in SVB is observed, and at a concentration of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline 75 mg / ml - partial suppression of the growth of SVB.

Example 2. With an initial amount of SVB equal to 10 ⁶ cells / ml, in the control experiment, an increase in SVB is observed, and at a concentration of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline 100 mg / ml - complete suppression of the growth of SVB.

Example 3. With the initial number of SVB equal to 10 ⁶ cells / ml, in the control experiment, an increase in SVB is observed, and at a concentration of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline 150 mg / ml - complete suppression of the growth of SVB.

Data illustrating the advantages of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline as a bactericide for inhibiting the growth of sulfate-reducing bacteria compared to the analogue are shown in table 1.

Table 1
The effectiveness of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline as a bactericide to inhibit the growth of sulfate-reducing bacteria The number of SVB, cells / ml Test compound Dosage, mg / l Control sowing fifty 75 one hundred 150 500 10 ³ 4-aminopyridine + + + + - + 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline - - - - - + 10 ⁶ 4-aminopyridine + + + + + + 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline ± - - - - + Note: + There is an increase in the SVB; ± partial suppression of the growth of SVB;
- Complete suppression of the growth of SVB

Advantages of the chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitroquinoline as a bactericide for inhibiting the growth of sulfate-reducing bacteria in comparison with the analogue:

1. High degree of protection. The analogue is effective only in the example with an amount of SVB equal to 10 ³ cells / ml. With more SVB, it does not work.

2. Low consumption rates (50 mg / l versus 500 mg / l in the analogue).

Claims (1)

Chemical compound 2- (4-pyridyl) -3-pentyl-6-bromo-8-nitriloquinoline of the formula

to inhibit the growth of sulfate-reducing bacteria