Method of obtaining 3,3'-(3,6-dioxaoctane-1,8-diyl)bis-1,5,3-dithiazepinane and its application as agent with fungicidal activity

FIELD: chemistry.

SUBSTANCE: invention relates to field of synthesis of compounds with biological activity, namely to method of obtaining compound 3,3'-(3,6-dioxaoctane-1,8-diyl)bis-1,5,3-dithiazepinane. Essence of method consists in interaction of 3,6-dioxaoctane-1,8-diamine with N1,N1,N6,N6-tetramethyl-2,5-dithiahexane-1,6-diamine in medium ethanol-chloroform (1:2 volume) in presence of catalyst SmCl3·6H2O with molar ratio 3,6-dioxaoctane-1,8-diamine:N1,N1,N6,N6-tetramethyl-2,5-dithiahexane-1,6-diamine:SmCl3·6H2O=1:2:(0.03-0.07) at temperature (~20°C) and atmospheric pressure for 2.5-3.5 h. Invention also relates to application of 3,3'-(3,6-dioxaoctane-1,8-diyl)bis-1,5,3-dithiazepinane as agent with fungicidal activity for fighting fungal diseases of agricultural crops.

EFFECT: improved method of obtaining 3,3'-(3,6-dioxaoctane-1,8-diyl)bis-1,5,3-dithiazepinane, possessing fungicidal activity against Botrytis cinerea.

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 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone formula (1) based on the catalytic reaction of 3,6-dioxaoctyl-1,8-diamine with N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine. The compound (1) having fungicidal activity against Botrytis cinerea, can be used to fight the microscopic fungi in plant protection:

The known method (Khafizova S. R., V. R. Akhmetova, L. F. Korzhova, T. V. Khakimova, G. R. Nadyrgulova, R. V. Kulakova, E. A. Kruglov, U. M. Dzhemilev. Multicomponent condensation of aliphatic amines with formaldehyde and hydrogen sulfide, Izv. An. Ser. chem., 2005, 2, 423) obtain 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (2) three-component condensation of Ethylenediamine with formaldehyde and hydrogen sulfide, taken in the molar ratio 1:6:4, respectively, at 80°C:

The known method does not allow to obtain 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine of formula (1).

The known method (R. V. Akhmetova, E. B. Rakhimova, A. B. Minnebaev, R. V. Kulakova, N. F. Galimzyanov. Cyclotrimethylene hetero-chain α,ω-diamines with formaldehyde and H2S // Russian journal of organic chemistry, 2012, (2) to obtain 5,5'-[ox(TIA)alkane-α,ω-diyl]-�IP-1,3,5-diazinane (3) three-component condensation of the Oxus(TIA)alkane-α,ω-diamines (3-oxapentane-1,5-diamine, 3,6-dioxaoctyl-1,8-diamine, 3,4-ditegakkan-1,6-diamine) with formaldehyde and hydrogen sulfide, taken in the molar ratio 1:6:4, respectively, at 60°C:

R=CH2CH2OCH2CH2,(CH2CH2O)2CH2CH2,(CH2CH2S)2.

The known method is not technological, as it implies the use of gaseous and highly toxic hydrogen sulfide, which at high concentrations is odourless, but even once its inhalation may cause pulmonary edema. In addition, the known method does not allow to obtain 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine of formula (1).

The known method (E. V. Rakhimova, E. A. Efremova, I. S. Bushmarinov, A. S. Goloveshkin, L. M. Khalilov, A. G. Ibragimov, U. M. Dzhemilev. A new method for the synthesis of α,ω-bis-1,5,3-dithiazepinanes using SmCl3·6H2O as the catalyst. // Tetrahedron Letters, 2012, 53, 32, 4225-4227) obtaining α,ω-bis-(1,5,3-diazepine-3-yl)-alkanes (4) reactions of transamination of N-(tert-butyl)-perhydro-1,5,3-diazepinone and recyclable 1-ox-3,6-ditzikloverina with α,ω-diamines:

The known method does not allow to obtain 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine of formula (1).

Known fungicidal agents for combating fungal diseases of plants based on 1,3,4-thiadiazolidine of Bicycle (5) and its adduct with CH3I (6) that to�centration of 0.04-0.13% completely inhibit the growth of V. sorokiniana, F. oxysporum, A. fumigatus, A. niger, P. variotii [Akhmetova, V. R., Murzakova, N. N., Khabibullina, G. R., Galimzyanova, N. F. Synthesis of N - and N,N'-coordinated derivatives of 3,7-dithia-1,5-diazabicyclo [3.3.0]octanes and their fungicidal activity. Russian Journal of Applied Chemistry, 2011, 84, 2, 225-229]. Bipolaris sorokiniana and Fusarium oxysporum included in the complex of root rot pathogens of cereals, Aspergillus niger is a common contaminant different materials and can cause allergic reactions and fungal infections in people with weakened immune systems [Microorganisms - causative agents of plant diseases. // Edited by beat VI - Kiev: Naukova Dumka, 1988, 552 S.; Sutton, D., Fothergill A., Rinaldi M. the Determinant of pathogenic and opportunistic fungi. New York: Wiley, 2001, 486]:

Known fungicidal agent against fungal diseases of plants based on derivatives thiazolyl-5-carbonamide formula (7) (Adolf Hubele, Patent RF 2070197), where R3- 2-furanyl, 2-thienyl, 3-furanyl, 3-thienyl; R1, R2- cyclopropyl, C1-C4- alkyl, CH2-O-R4, R4-C1-C4- alkyl:

Known (H. Kanno. Pure&Appl. Chem. 1987. Vol.59. No. 8. P. 1027-1032) fungicide buprofezin of the General formula (8), the structure of which contains 1,3,5-thiadiazines cycle, designed to combat fungal diseases of crops. Production famous�th fungicide (8) is a 2-stage synthesis and is based on the use of remote initial reagents:

Known fungicidal activity for derivatives on the basis of 1.5-thiazepine (9) [V. Ambrogi et al. European Journal of Medicinal Chemistry, 1990, 25, 5, 403-411]:

Known fungicidal agents to combat fungal diseases of crops on the basis of 3,3'-bi-1,5,3-diazepinone formula (10) (Dzhemilev U. M., Murzakova N. N., G. R. Khabibullin, V. R. Akhmetov, Temkina T. V., N. Galimzyanov.F., Ibragimov A. G. Patent RF 2448107):

The syntheses of these compounds or multi-stage or based on the use of expensive reagents.

Known fungicidal activity for 5,5'-(3,6-dioxaoctyl-1,8-diyl)bis-1,3,5-diazinane (11) in respect of microscopic fungi Bipolaris sorokiniana and Aspergillus niger [Akhmetova, R. V., Rakhimova, E. B., Minnebaev, B. A., Kunakova, R. V., Galimzyanova, N. F. Cyclothiomethylation of heterochain α,ω-diamines with formaldehyde and H2S. Russian Journal of Organic Chemistry, 2012, 48, 2, 202-208]. The compound (11) receive a three-component condensation of 3,6-dioxaoctyl-1,8-diamine with formaldehyde and hydrogen sulfide, taken in the molar ratio 1:6:4, respectively, at a temperature of 60°C. a Method of producing 5,5'-(3,6-dioxaoctyl-1,8-diyl)bis-1,3,5-diazinane (11) not technologically, as it implies the use of gaseous and highly toxic hydrogen sulfide, which at high concentrations is odourless, but even odnokratno�e its inhalation may cause instant death:

A new method of obtaining 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone of formula (1) as a means fungicidal activity in one preparative stage of initial reagents available.

The method consists in the interaction of 3,6-dioxaoctyl-1,8-diamine with N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine in the presence of a catalyst SmCl3·6H2Oh, taken in a molar ratio of 3,6-dioxaoctyl-1,8-diamine: N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine: SmCl3·6H2About=1:2:(0.03-0.07), preferably 1:2:0.05, for 2.5-3.5 h at room temperature (~20°C) and atmospheric pressure in the environment of the solvent ethanol-chloroform (1:2, by volume). The yield of 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone (1) is 47-55%. The reaction proceeds according to the scheme:

3,3'-(3,6-Dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine (1) is formed only with the participation of N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine [P. P. Khairullina, B. F. Akhmanov, T. V. Temkina, R. V. Kunakova, A. G. Ibragimov. N,N,N',N'-tetramethylethylene is an effective reagent for aminomethylpyridine thiols. Russian journal of organic chemistry, 2012, 48, 2, 189-193] and 3.6-dioxaoctyl-1,8-diamine, taken in the molar ratio 2: 1 (stoichiometric amount). In another aspect]�tion to the initial reagents reduces the yield of the target product (1). Without catalyst the reaction proceeds with output not exceeding 10%.

The conduct of a specified reaction in the presence of a catalyst SmCl3·6H2Of more than 7 mol. % does not significantly increase the yield of the target product (1). The use of the catalyst SmCl3·6H2About less than 3 mol. % reduces output (1), which is connected, possibly, with a reduction of catalytically active sites in the reaction mass. 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 (e.g., at 0°C) decreases the reaction rate. The experiments were carried out in the solvents ethanol-chloroform (1:2, by volume), because they are well dissolved starting compounds.

Identification of fungicidal activity carried out using microscopic fungi Bipolaris sorokinlana, Fusarium oxysporum, Botrytis cinerea and Rhizoctonia solani. Microscopic fungi are maintained in the collection of microorganisms of the Institute of biology, Ufa research centre. For tests used the solutions of (1) in DMF. Evaluation of the influence of the solvent DMF with the test culture of fungi showed no negative impact on the development of microscopic fungi.

A common methodology for the evaluation of fungicidal activity of the compound (I):

Evaluation of the fungicidal activity was conducted by the method of diffusion in agar (Workshop on Microbiology. // Ed. by Egorov� N. With. - M.: Publishing house of Moscow state University, 1976, 307). The surface of the medium (potato-glucose agar), and poured 15 ml in Petri dishes (d 70 mm, was inoculated with spore suspension of the test cultures of fungi. Then in the environment of a drill diameter of 10 mm cut out hole into which was placed 100 μl of the test solutions. Fungicidal activity was evaluated by the diameter of the zone of inhibition of growth of micromycetes, as well as watching the development of the test cultures using a light microscope Leica DM 1000 at magnification ×10. Repeated three times. Control was the development of fungi on nutrient medium. The time of incubation 7 days at 28°C.

The influence of a solution of 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone (1) in DMF with the test culture withspecific. 3,3'-(3,6-Dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine (1) in the studied concentration completely inhibits development of Botrytis cinerea, have fungistatic activity against Rhizoctonia solani, has no negative impact on the development of Bipolaris sorokiniana and Fusarium oxysporum (table 1).

Table 1
The effect of 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone (1) on the development of test-cultures of fungi after 7 days incubation
Types of mushroomsThe diameter of zone filing�moving the growth of fungi, (mm)Control
C10.04andC10.09andC10.13a
Botrytis cinereaThere is no development of fungusThere is no development of fungusThere is no development of fungusThe beginning of the spore formation
Rhizoctonia solaniSeparate microcolonies out of rangeSeparate microcolonies out of rangeSeparate microcolonies out of rangeNormal development of the fungus
Bipolaris sorokinianaThere is no areaThere is no areaThere is no areaThe beginning of the spore formation
Fusarium oxysporumThere is no areaThere is no areaThere is no areaSporulation
andthe concentration of compound (1) in DMFA %

Thus, 3,3'-(3,6-dioxa�Chan-1,8-diyl)bis-1,5,3-diazepine (1) shows fungicidal effect against Botrytis cinerea and has fungistatic activity against Rhizoctonia solani.

Significant differences of the proposed method:

In the known method the reaction proceeds with participation as a source of gaseous reactants and hydrogen sulfide aqueous solution of formaldehyde at a temperature of 60°C with the formation of six-membered 5,5'-[ox(TIA)alkane-α,ω-diyl] bis-1,3,5-diazinane (3). The known method cannot be obtained individually 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine of formula (1). In the proposed method the reaction proceeds with participation as a source of reagent N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine at room temperature, -20°C under the action of catalyst SmCl3·6H2About the Proposed method allows one preparative stage to synthesize individual 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepine (1) with fungicidal activity.

The method is illustrated by examples:

Example 1. In the vessel Slanka, mounted on a magnetic stirrer in an argon atmosphere at a temperature of ~20°C is placed 0.15 g (1 mmol) of 3,6-dioxaoctyl-1,8-diamine in 5 ml of ethanol and 0.018 g (0.05 mmol) SmCl3·6H2Oh, then added 0.42 g (2 mmol) of N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine in 10 ml of chloroform. The reaction mixture was stirred at a temperature of ~20°C for 3 h and allocate column chromatography on SiO23,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-disease�Inan with a yield of 51%.

Other examples of the method are shown in table 2.

Table 2
№№ p/pSource alindemanThe ratio of alindeman: N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine: SmCl3·6H2Oh, mmol 1:2:0.05Reaction time, hoursOutput (1), %
13,6-dioxaoctyl-1,8-diamine351
2- "-1:2:0.03347
3- "-1:2:0.07355
4- "-1:2:0.052.548
5- "-1:2:0.05 3.554

All experiments were performed in the environment of ethanol-chloroform (1:2, by volume) at room temperature (~20°C).

The spectral characteristics of 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone*:

A white crystalline solid. So a MP 74-75°C. the NMR Spectrum1N (δ, M. D., J, CDCl3): 2.93 t (4H, J=5.4 Hz, H-8, H-8/); 3.06 ush.(8H, H-6, H-6/N-7, N-7/); 3.62 m (8H, H-9, H-9/, H-10, H-10/); 4.23 ush.(8H, H-2, H-2/, H-4, H-4/). The NMR spectrum13With (δ, M. D.): 35.87 (C-6, C-6/, C-7, C-7/); 50.40 (C-8, C-8/); is at 59.97 (s-2, s-2/, C-4, C-4/); 68.83 (C-9, C-9/), 70.41 (C-10, C-10/). MALDI TOF, m/z: 385.321 [M+H]+. C14H29N2O2S4:

*Control reactions were carried out by TLC on plates Silufol W-254, showed 12 pairs. For column chromatography used silica gel KSK (100-200 µm). The melting point is defined on the device OOC 80/2617. The NMR spectra of 1D (1N,13C) and 2D (COSY, NOESY, HSQC, NMVS) filmed on a Bruker Avance 400 (100.62 MHz for13With and 400.13 MHz for1H) by standard methods Bruker, internal standard Me4Si, solvent - CDCl3. Mass high resolution spectra obtained on the instrument MALDI TOF/TOF AUTOFLEX III, Bruker.

The advantages of the present invention:

The compound (1) is an effective means� against Botrytis cinerea, the synthesis is carried out in one preparative stage, based on available reagents, in contrast to the multistep syntheses of known agents used to combat fungal diseases of plants.

1. A method of obtaining 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone (1):

characterized in that the 3.6-dioxaoctyl-1,8-diamine is subjected to interaction with N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine in the environment of ethanol-chloroform (1:2, by volume) in the presence of a catalyst SmCl3·6H2O with a molar ratio of 3,6-dioxaoctyl-1,8-diamine : N1N1N6N6tetramethyl-2,5-ditegakkan-1,6-diamine : SmCl3·6H2O=1:2:(0.03-0.07) at room temperature (~20°C) and atmospheric pressure for 2.5-3.5 h.

2. The use of 3,3'-(3,6-dioxaoctyl-1,8-diyl)bis-1,5,3-diazepinone as a means fungicidal activity to combat fungal diseases of crops, caused by the fungus Botrytis cinerea.



 

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32 cl, 111 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel chromenone derivatives of formula II or its pharmaceutically acceptable salts, where each R20 is hydrogen; R11 is selected from phenyl and 5-6 member saturated or aromatic heterocycle, including one or two heteroatoms, selected from N, O or S, where R11 is optionally substituted with one-two substituents, independently selected from C1-C4alkyl, =O, -O-R13, -(C1-C4alkyl)-N(R13)(R13), -N(R13)(R13), where each R13 is independently selected from hydrogen and -C1-C4alkyl; or two R13 together with nitrogen atom, to which they are bound, form 5-6-member saturated heterocycle, optionally including one additional O, where, when R13 is alkyl, alkyl is optionally substituted with one or more substituents, selected from -OH, fluorine, and, when two R13 together with nitrogen atom, to which they are bound, form 6-member saturated heterocycle, saturated heterocycle is optionally substituted on each carbon atom with -C1-C4alkyl; R12 is selected from phenyl and pyridyl, where R12 is optionally substituted with one or more substituents, independently selected from halogen, C1-C4alkyl, C1-C2 fluorine-substituted alkyl, -O-R13, -S(O)2-R13, -(C1-C4alkyl)-N(R13)(R13), -N(R13)(R13); R14 is selected from hydrogen; and X1 is selected from -NH-C(=O)-†, -C(=O)-NH-†, - -S(=O)2-NH-†, where † stands for place, where X1 is bound with R11; and, when R14 is H; R12is phenyl; and X1 is - C(=O)-NH-†, then R11 is not 1H-pyrazol-3-yl, possessing stimulating activity.

EFFECT: invention relates to pharmaceutical composition based on said compounds, method of treating subject, suffering from or having resistance to insulin, metabolic syndrome or diabetes, as well as to method of increasing sensitivity to insulin.

16 cl, 1 tbl, 24 ex

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

FIELD: chemistry.

SUBSTANCE: invention relates to pesticides. Compound of formula in which X1 stands for halogen; X2 stands for CF3, OCF3, SCF3, S(O)CF3, S(O2)CF3 or SF5, and Y stands for O, S, S(O) or S(O2) (1S)-enantiomer of formula I compound. Composition for fighting parasites in addition to carriers and/or dispersing substances contains as active ingredient at least one formula I compound. Formula I compound is applied for fighting parasites on warm-blooded animals.

EFFECT: invention makes it possible to increase fight efficiency.

13 cl, 3 tbl

FIELD: chemistry.

SUBSTANCE: herbicidal composition in the form of a microemulsion concentrate contains an ester of C7-C9 alcohols of 2,4-dichlorophenoxyacetic acid with a normal or isomeric structure separately or in a combination, a trialkylamine salt of 2,4-dichlorophenoxyacetic acid which includes one alkyl radical with not less than 8 carbon atoms, a trialkylamine salt of 2-methoxy-3,6-dichlorobenzoic acid which includes one alkyl radical with not less than 8 carbon atoms, a nonionic or cationic surfactant or a mixture thereof and possibly contains an organic solvent or a mixture thereof.

EFFECT: herbicidal composition is capable of forming thermodynamically stable microemulsion aqueous solutions with droplet size of the dispersion phase in the nanometre range.

3 cl, 5 tbl

FIELD: chemistry.

SUBSTANCE: herbicidal agent contains a herbicidally effective amount of a surface-active trialkylamine salt of 2,4-dichlorophenoxyacetic acid, wherein one alkyl radical contains at least 8 carbon atoms, and a surfactant. The surfactant used is a nonionic or cationic surfactant or a mixture thereof. The herbicidal agent can contain a herbicidally effective amount of a C7-C9 alcohol ester of 2,4-dichlorophenoxyacetic acid with a normal or isomeric structure separately or in a combination. The herbicidal agent can contain an organic solvent.

EFFECT: invention increases stability of the agent.

3 cl, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to antifungal preparation, containing effective quantity of methyl ether of 2-benzimidazolylcarbamic acid, or its salts with inorganic and organic acids, or their hydrates, or its complex compounds with organometallic and inorganic salts, containing transition metal. Claimed invention demonstrates antifungal activity with respect to causative agents of mycoses from the group, including Trichophyton mentagrophytes var. Interdigitale, Trichophyton rubrum, Microsporum canis, Trichophyton mentagrophytes var. granulosum, Candida albicans. Antifungal activity has been detected with respect to pathogenic and opportunistic fungi, causing mycoses of mucosa and skin in humans and animals.

EFFECT: increased activity of preparation.

9 cl, 4 tbl, 28 ex

FIELD: chemistry.

SUBSTANCE: group of inventions relates to biotechnology and agriculture. Claimed are compounds A-87774, represented by compounds A-87774-1, A-87774-2, A-87774-3 or their salt, method of obtaining compounds A-87774, strain Streptomyces sp. FERM BP-10840, producing compounds A-87774, culture product, obtained by cultivation of strain Streptomyces sp. FERM BP-10840, method of elimination of weeds and method for plant growth regulation with application of said compounds, as well as herbicide and plant growth regulator, containing culture product or said compounds as active ingredient.

EFFECT: compounds A-87774 possess excellent herbicidal and plant growth regulating action, are easily degradable in the environment.

13 cl, 9 dwg, 8 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to field of organic chemistry, namely to crystalline form of 2-ethyl-3,7-dimethyl-6-(4-trifluoromethoxy)phenoxy)quinolin-4-ylmethylcarbonate. Invention also relates to method of obtaining said crystalline form and agrochemical composition based on said crystalline form.

EFFECT: obtained is stable in storage crystalline form of 2-ethyl-3,7-dimethyl-6-(4-trifluoromethoxy)phenoxy)quinolin-4-ylmethylcarbonate, possessing insecticidal activity.

6 cl, 8 dwg, 2 tbl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 4-amino-5-fluoro-3-halogen-6-(substituted)picolinate of formula I , where W represents Cl, Br or I; R represents C1-C4 alkyl, cyclopropyl, C2-C4 alkenyl or phenyl, substituted with 1-4 substituents, independently selected from halogen, C1-C4 alkyl, C1-C4 halogenalkyl, C1-C4 alkoxy or C1-C4 halogenalkoxy; and R1 represents C1-C12 alkyl or non-substituted C7-C11 arylalkyl; which includes the following stages: fluorine exchange, amination, halogen exchange, halogenation and binding by means of transition metal.

EFFECT: method improvement.

7 cl, 6 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of obtaining 4-amino-3-chloro-5-fluoro-6-(substituted)picolinate of formula I where R stands for (C1-C4)alkyl, cyclopropyl, (C2-C4)alkenyl or phenyl, which contains from 1 to 4 substituents, as such independently selected are: a halogen, (C1-C4)alkyl, (C1-C4)halogenalkyl, (C1-C4)alkoxy or (C1-C4)halogenalkoxy; R1 stands for (C1-C12)alkyl or non-substituted or substituted (C7-C11)arylalkyl; which includes the following stages: a) fluorination of 3,4,5,6-tetrachloropicolinonitrile by a source of fluoride-ions, b) amination of 3-chloro-4,5,6-trifluoro-2-picolinonitrile with ammonia, c) substitution of fluorine-substituent in position 6 with 4-amino-3-chloro-5,6-difluoropicolinonitrile by means of hydrogen bromide (HBr), hydrogen chloride (HCl) or hydrogen iodide (HI) and nitrile hydrolysis, d) etherification of 4-amino-3-chloro-5-fluoro-6-halogenpicolineamide by a strong acid and alcohol (R1OH) and e) combination of 4-amino-3-chloro-5-fluoro-6-halogenpicolinate of formula E with an aryl-, alkyl- or alkenylmetalorganic compound.

EFFECT: obtaining the target product with the high output.

2 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to herbicidal compositions, containing glyphosphate or its salt and surface-active substance, including, at least, one alkoxylated monoglyceride, at least, one alkoxylated diglyceride or mixture of alkoxylated mono- and diglycerides. Undesired plants are processed with effective quantity of said compositions.

EFFECT: invention makes it possible to increase processing efficiency.

34 cl, 2 dwg, 6 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the field of organic chemistry, in particular, to a method of obtaining N, N'-bis-(2-hydroxyethyl)tetrathiadiazacycloalkanes of the general formula (1) 1a n=3, 1b n=4, 1c n=5, 1d n=6. The essence of the method consists in the interaction of a formaldehyde mixture and α,ω-dithiol with 2-aminoethanol with the molar ratio of formaldehyde : α,ω-dithiol : 2-aminoethanol = 2:1:1 at room temperature (~20°C) and atmospheric pressure for 2.5-3.5 h. The invention also relates to the application of the formula (1) compounds as means with fungicidal activity for fighting fungal diseases of agricultural cultures.

EFFECT: obtaining the formula (1) compounds, possessing the fungicidal activity against Bipolaris sorokiniana and Rhizoctonia solani.

2 cl, 5 tbl, 1 ex

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