Method of obtaining 1,6-bis-(1,5,3-dithiazepan-3-yl)-2,5-disulphanylhexane, possessing fungicidal activity

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 1,6-bis-(1,5,3-dithiazepan-3-yl)-2,5-disulphanylhexane of formula (1), possessing fungicidal activity against Botrytis cinerea and Rhizoctonia solani. Essence of method lies in interaction of mixture of 1,2-ethanedithiol and formaldehyde with water solution of ammonium salts NH4X (X=F, Br, OAc, NO3, 1/2SO4) with molar ratio HS(CH2)2SH:CH2O:NH4X=3:6:2 at room temperature (~20°C) and atmospheric pressure for 5-7 h.

EFFECT: output of 1,6-bis-(1,5,3-dithiazepan-3-yl)-2,5-disulphanylhexane of general formula (1) depending on applied ammonium salts (NH4X) constitutes 31-67%.

2 cl, 2 tbl, 1 ex

 

The present invention relates to the field of synthesis of compounds with biological activity, specifically, to a method for producing 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation formula (1) based on three-component reaction of 1,2-identicial, formaldehyde and ammonium salts. The compound (1) having fungicidal activity against Botrytis cinerea and Rhizoctonia solani, can be used to fight the microscopic fungi in the protection of plants and materials.

The known method [K. Ito. Preparation of N-Alkylthiomethyl Derivatives of Hydroxylamines. Chem. Pharm. Bull. 1979, 27 (7), 1691-1694] obtain hydrochloride of 3-hydroxy-1,5,3-diazepine (2) the reaction of hydrochloric acid hydroxylamine with formaldehyde (35% aqueous solution) and 1,2-acondition in ethanol at room temperature with a yield of 74% according to the scheme:

The known method cannot be obtained 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-disulfonates of the General formula (1).

The known method [U. M. Dzhemilev, N. N. Murzakova, G. R. Khabibullin, V. R. Akhmetov, T. V. Temkina, N. F. Galimzyanov, A. G. Ibragimov. A method of obtaining 3,3'-bi-1,5,3-diazepine and its use as a medium with fungicidal activity against Bipolaris sorokiniana, Aspergillus fumigates, Aspergillus niger and Paecilomyces variotii. RF patent №2448107 from 20.04.2012] obtain 3,3'-bi-1,5,3-diazepine (3) fungicidal activity by the interaction of 1,2-atandi�Iola with formaldehyde (37% aqueous solution) and hydrazine hydrate (60% solution) with access 64-87% scheme:

The known method cannot be obtained 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1).

Thus, the literature contains no information on obtaining 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation of the General formula (1).

A method of obtaining 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation of the General formula (1) having fungicidal activity, in one-stage process of initial reagents available.

The method consists in the preliminary mixing 1,2-identicial with formaldehyde (CH2O) at room temperature (~20°C) for 30 min followed by the addition of an aqueous solution of ammonium salts of NH4X, where X=F, Cl, Br, SLA, NO3,1/2SO4taken in a molar ratio of HS(CH2)2SH:CH2About:NH4X=3:6:2, and stirring for 5-7 hours at a temperature of ~20°C and atmospheric pressure. Allocate 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation of formula (1), the output of which depending on the applied ammonium salts is 31-67%. The reaction proceeds according to the scheme:

1,6-Bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation of formula (1) is formed only with the participation of 1,2-identicial, formaldehyde and an aqueous solution of ammonium salts (X=F, Cl, Br, OAc, NO3,1/2SO4) taken in stechiometric�whom the ratio 3:6:2. When a different ratio of initial reagents decreases the selectivity of the reaction. In the presence of other α,ω-dithiolo (for example, 1,3-propanedithiol, 1,4-butandiol, 1,5-pentandiol), other aldehydes (e.g., alkyl-, arylamidine aldehydes) of the target product (1) is formed. Reactions were carried out at room temperature (~20°C). At temperatures above 20°C (e.g. 60°C) increase energy costs, and at temperatures below 20°C (for example, -10°C) decreases the reaction rate. Reactions were carried out in water, because the reactants are readily soluble in water and the target product of the General formula (1) precipitates and is easily separated from the reaction mass.

Identification of fungicidal activity carried out using microscopic fungi Bipolaris sorokiniana, Fusarium oxyspomm, Aspergillus fumigates, Paecilomyces variotii, Botrytis cinerea and Rhizoctonia solani, which cause various diseases of agricultural plants, including root rot of cereals and wood (Microorganisms - causative agents of plant diseases. Ed beat V. I. Kiev: Naukova Dumka, 1988, 552 p.). Microscopic fungi are maintained in the collection of microorganisms of the Institute of biology, Ufa research centre.

Evaluation of the fungicidal activity was conducted by the method of diffusion in agar (Workshop on Microbiology. Ed Egorova N. With. - M.: Publishing house of Moscow state University, 1976, 307 p.).

For tests used the solutions of (1) in DMF. Est�and the influence of the solvent DMF with the test culture of fungi showed no negative impact on the development of microscopic fungi.

1,6-Bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1) in the studied concentrations inhibits development of Botrytis cinerea and Rhizoctonia solani in all investigated concentrations and has no negative impact on the development of Bipolaris sorokiniana, Fusarium oxysporum, Aspergillus fumigates, Paecilomyces variotii.

Table 1
Evaluation of the effect of 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1) on the development of test-cultures of fungi (the period of 7 days incubation, zone of inhibition, mm)
Types of mushroomsConcentration, % (in DMF)Control
0.10.20.5
Bipolaris sorokinianaThere is no areaThere is no areaThere is no areaSporulation
Fusarium oxysporumThere is no areaThere is no areaThere is no areaSporulation
Aspergillus fumigatesNo zone d�istia There is no areaThere is no areaSporulation
Paecilomyces variotiiThere is no areaThere is no areaThere is no areaSporulation
Botrytis cinereaThere is no development of fungusThere is no development of fungusThere is no development of fungusThe beginning of the spore formation
Rhizoctonia solaniThere is no development of fungusThere is no development of fungusThere is no development of fungusNormal development

Thus, 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1) exhibits fungicidal activity against Botrytis cinerea and Rhizoctonia solani.

The results indicate that compound (1) can be used in the seed treatment, the spraying of aerial parts of the plants during budding, the processing of natural and synthetic polymeric materials.

Significant differences of the proposed method.

In the proposed method, in kachestvuimportnym reagents used are commercially available ammonium salts (NH 4X, where X=F, Cl, Br, OAc, NO3,1/2SO4)). The proposed method allows in one technological stage to synthesize individual 1,6-bis-(1,5,3-diazepan-3-yl)-2,5 - desulfonylation (1) with fungicidal activity. In the known method the reaction proceeds with participation as a source of reagent water 60% solution of hydrazine with the formation of 3,3'-bi-1,5,3-diazepine (3). The known method does not allow to obtain 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation the General formula (1).

The method is illustrated by the following examples.

Example 1. In a glass reactor, mounted on a magnetic stirrer at room temperature (~20°C) was placed 1,2-acondition (0.25 ml, 3 mmol) and 37% aqueous formaldehyde (0.44 ml, 6 mmol), stirred for 30 min, add salt ammonium NH4F (0.074 g, 2 mmol) in 3 ml of water, stirred for 6 h, the resulting white precipitate was filtered, washed with distilled water 3*15 ml), and dried. The crystals were recrystallized from chloroform. The yield of 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1) 65% (0.25 g).

Other examples of the method are shown in table.2.

Table 2
№ p/pNH4X, XTotal output (1), %
1F665
2F558
3F767
4Cl660
5Br631
6NO3644
7OAc641
81/2SO4636

All experiments were performed in water at a molar ratio of 1,2-acondition : formaldehyde : ammonium salt=3:6:2 and room temperature (~20°C).

Physico-chemical characteristics of compounds (1).

(NMR-spectra of1H and13C were recorded on a Bruker Avance-400 working hours�the frequency 300.13 and 100.62 MHz, solvent - CDCl3C77.10 M. D.). IR spectra were filmed on a Bruker Vertex 70 v in suspension in vaseline oil. The mass spectra of compounds were recorded on spectrometer MALDI - TOF Autoflex III (Broker, Germany), as the matrices used α-cyano-4-hydroxycinnamic and 2,5-dihydrobenzoic acid. Elemental composition (C, H, N and S was determined on the device Karlo Erba-1106.)

1,6-Bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1)

White crystals, MP of 142-143°C (CHCl3). The IR spectrum, ν/cm-1: 666 (-C-S-C-), 1093 (C-N), 1461 (CH2), 2923 (CH3). The NMR spectrum1H (5, M. D., CDCl3, J/Hz): 2.75 (s, 4H, H2C(10, 10')); 3.06 (C, 8H, H2C(2, 2', 3, 3')); 3.93 (s, 4H, H2C(8, 8')); 4.30 (C, 8H(5, 5', 7, 7')). The NMR spectrum13C (5, M. D.): 30.95 (C(10, 10')); 35.94 (C(2, 2', 3, 3')); 54.89 (With(8, 8')); 58.07 (With(5, 5', 7, 7')). Found (Percent): C, 57.88; H, 6.64; N, 16.53; S, 20.30. C8H10ON2S. Calculated (Percent): C, 57.80; H, 6.06; N, 16.85; S, 19.29. The mass spectrum (MALDI): 388.416 (100) [M]+.

1. The method for obtaining 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation (1)

wherein the pre-prepared at 20°C a mixture of an aqueous solution of formaldehyde and 1,2-identicial is subjected to interaction with aqueous solution of ammonium salt NH4X (X=F, Cl, Br, OAc, NO3,1/2SO4) with a molar ratio of HS(CH2)2SH:CH2O:NH4X=3:6:2 at a temperature of ~20°C and at�uspernom pressure within 5-7 p.m.

2. The use of 1,6-bis-(1,5,3-diazepan-3-yl)-2,5-desulfonylation as a means fungicidal activity to combat fungal diseases of crops, Botrytis cinerea and Rhizoctonia solani.



 

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SUBSTANCE: paleontological objects with soft tissues are treated for 1-4 months with an embalming solution containing 40% formalin - 0.516%, crystalline phenol - 0.262%, glycerine - 79.077%, 96% alcohol - 18.576%, sodium chloride - 1.569%. The ratio of the embalming solution to the mass of the paleontological object must not be less than 3:1. Embalming is carried out at room temperature.

EFFECT: method of embalming paleontological objects with soft tissues provides prolonged preservation of soft tissues, minimises loss of soft tissues having different rotting stages, stops rotting processes, skin straightening, preserves natural colour thereof and natural morphometric parameters, which enables further use of the paleontological object for scientific purposes and for exhibition in dry form.

3 cl

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