1-alkynyl-2-aryloxyalkylamides and use thereof as fungicides

FIELD: chemistry.

SUBSTANCE: compounds of formula (1) are described, where substitutes are as defined in the formula of invention. Methods of obtaining formula (1) compounds are described, when n equals 0. Described also is a fungicide composition based on formula (1) compounds and a phytopathogenic fungus control method which uses compounds in paragraph 1 or a composition based on the said compounds.

EFFECT: obtaining compounds with fungicide properties.

17 cl, 60 tbl, 5 ex

 

The text descriptions are given in facsimile form.

1. N-quinil-2-alkylthio-2-(aryloxy or heteroaromatic)alkylamide General formula (1):

in which Ar denotes a group of formula (A):

in which Ar denotes fenoxaprop, and2and3denote H;
or And1and2form a 5-membered saturated or unsaturated ring or 6-membered saturated ring, optionally containing as substituents With1-C6alkyl or oxoprop, where if ring is a 5 membered saturated ring, optionally 2 carbon atoms are independently replaced by an atom of O or S, or if the ring is 5-membered unsaturated ring, optionally 1 carbon atom is replaced by an atom of O or S and unsaturated 5-membered ring optionally condensed with a benzene ring, which optionally may be substituted with halogen, and3denotes H; or Ar represents a group of formula (B1):

in which L denotes CQ, and M denotes N;
Kaand Kbindependently oboznachayut;
V denotes N or C1-C6alkyl;
Q represents phenyl or thienyl;
R1stands With1-C4alkyl;
R2denotes H;
R2and R4independently denote With1-C6alkyl;
R5denotes H, C1-C8alkyl, which optionally contains, as a Deputy With1-C6alkoxygroup; and
n is 0.

2. The compound according to claim 1, in which R5denotes H or methyl, Ar denotes a group of formula (A), and1denotes fenoxaprop.

3. The compound according to claim 1, in which Ar denotes a group of formula (A), and1denotes fenoxaprop.

4. The compound according to claim 1, in which Ar represents 3-phenoxyphenyl.

5. The compound according to claim 1, in which Ar denotes dibenzofuran-2-yl, optionally substituted with halogen or1-C4the alkyl.

6. The compound according to claim 1, in which Ar denotes benzofuranyl or benzothiophene.

7. The compound according to claim 1, in which Ar represents 3-phenylindolin-6-yl.

8. The compound according to claim 1, in which R1denotes methyl.

9. The compound according to claim 1, in which R2denotes N.

10. The compound according to claim 1, in which R3and R4both represent methyl.

11. The compound according to claim 1, in which R5denotes H, methyl or methoxymethyl.

12. The connection section 12, in which R5denotes H or methyl.

13. The compound according to claim 1, in which oterom Ar denotes benzofuran-5-yl, benzothiophen-5-yl, benzofuran-6-yl or benzothiophen-6-yl, R1, R3and R4denote methyl, R2denotes H, R5denotes H or methyl, and n is 0.

14. The method of obtaining the compounds of formula (1) according to claim 1, in which n is 0, including
(a) interactions of the compounds of formula (4)
,
where R6stands With1-C4alkyl, a R1is such as defined in claim 1, with a halogenation reagent,
(b) the interaction of the compounds of the formula (5)

in the presence of a base with a compound Ar-HE, where Ar is as defined in claim 1, to obtain the compounds of formula (6)
,
(C) the transformation of this compound in the presence of a base to the corresponding acid of formula (7)

and (d) the interaction of this acid with the amine of formula (8)
,
where R2-R5are as defined in claim 1.

15. The method of obtaining the compounds of formula (1) according to claim 1, in which n is 0, including
(a) interactions of the compounds of formula (13)

where R1is such as defined in claim 1,
with an amine of formula (8)
,
where R2-R5are as defined in claim 1,
getting connection f is rmula (14)
,
(b) the processing of this connection halogenation reagent to obtain the compounds of formula (16)

and (C) the interaction of this compound in the presence of a base with Ar-HE, where Ar is as defined in claim 1.

16. Fungicidal composition comprising fungicide effective amount of the compounds of formula (1) according to claim 1 and a suitable carrier or diluent.

17. A method of combating phytopathogenic fungi, comprising applying to the plant, to seed of a plant, to the locus of the plant or seed or to soil or any other medium in which the plant grows fungicide effective amount of a compound according to claim 1 or the composition according to item 16.



 

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FIELD: chemistry, pharmacology.

SUBSTANCE: claimed invention relates to sulfamate derivatives of benzothiophene, obtained by method including stages: 1) conversion of 6-methoxybenzothiophene (3); , where R3 represents monobromine-derivative using N-bromosuccinimide and APTS in standard conditions; 2) conversion of said monobromine-derivative by interaction with Mg in Et2O in argon atmosphere into magnesium-organic bromide and its further condensation with ketone or aldehyde selected from group, consisting of cyclopentanone, cyclohexanone, cycldecanone, 4-methylcyclohexanone, 2-methylcyclohexanone, 2,2-dimethylcyclopentanone, 2-adamantanone, propanal, hexanal, cyclohexane carboxaldehyde, cycloheptancarboxaldehyde in Et2O obtaining corresponding hydroxyl-substituted methoxybenzothiophene in standard conditions; 3) processing said hydroxy-substituted methoxybenzothiophene with triethylsilane in argon atmosphere in dichlomethane obtaining corresponding substituted methoxybenzothiophene; 4) optional alkylating of corresponding substituted methoxybenzothiophene using standard conditions obtaining corresponding substituted methoxybenzothiophene, carrying (C1-C6)alkyl or (C3-C12)cycloalkyl; removal of protective group from substituted methoxybenzothiophene, obtained at stage 3) or stage 4) in presence of tribromborane in standard conditions; conversion of obtained hydroxy-compound into corresponding sulfamate by processing with sodium hydrate and amidochlorsulfonic acid, or interaction with sulfamoylchloride in dimethylacetamide; 7) optional oxidation of obtained compound with hydrogen peroxide in trifluoracetic acid in standard conditions. Compounds can be used as inhibitors of steroid sulfatase enzyme in production of medication for treatment or prevention of estrogen-depending disorders. Also described are pharmaceutical composition based on compounds I and application of the latter.

EFFECT: obtaining compounds which can be used as inhibitors of steroid sulfatase enzyme in production of medication for treatment or prevention of estrogen-depending disorders.

43 cl, 1 dwg, 10 tbl, 67 ex

FIELD: organic chemistry, analytical chemistry.

SUBSTANCE: invention relates to synthesis of novel analytical reagents of chelate-forming type. Synthesized compounds represent chelate-forming dibenzo-containing five-membered cyclic compounds comprising two symmetric β-dicarbonyl substitutes bound covalently with fluorine-containing radicals of the general formula (1): , wherein X means -CH2, oxygen (O), sulfur (S) atom, -NR; if X means -CH2 then R means hydrogen atom (H); R2 means -C(O)CH2C(O)Rf wherein Rf means -(CF2)nY wherein n = 1-6, and at n = 1 Y means H, F, Cl, Br, -OCF3, -OCH3, -OC3F7, -OCF2-CF2-OCF3, -C6F5, -C(O)OAlk wherein Alk means hydrocarbon radical; at n = 2 Y means H, F, Cl, Br, -OCF3, -OC3F7, -OCF2-CF2-OCF3, -C(O)OAlk; at n = 3, 5 or 6 Y means F, -C(O)OAlk; at n = 4 Y means H, F, Cl, -C(O)OAlk; if X means O, S or -NR then R means H or Alk, R2 means H, R1 means -C(O)CH2C(O)Rf. Invention can be used in field of luminescent-spectral analysis, in particular, for clinical diagnosis of object of biogenic origin, and in technique field for using as extractants of heavy and rare-earth metal ions for their extraction and/or purifying from their impurities of sewage and contour waters.

EFFECT: valuable medicinal and technical properties of compounds.

1 cl, 19 dwg, 19 ex

The invention relates to a method for producing crystalline MES or resolutionvideo crystalline 6-hydroxy-2(4-hydroxyphenyl) 3-(4-(2-piperidinoethyl)benzoyl/benzo (b)difengidramin by acylation protected derivative of 2-arylbenzofurans trichloride in the presence or trichromate boron, followed by separation of the crystalline MES, by dissolving the latter in a hot solution containing methanol and water, the concentration of a solution

FIELD: chemical technology.

SUBSTANCE: invention relates to a method for preparing tetrafluoroethane-β-sultone that can be used in synthesis of substances used as bactericidal and insecticide preparations, chemical sources of current and fluorine-containing membranes. Method involves interaction of gaseous tetrafluoroethylene with preliminary prepared mixture of liquid freshly distillated sulfuric anhydride with tetrafluoroethane-β-sultone wherein tetrafluoroethylene is fed to this mixture at temperature 80°C, not above, and under autogenous pressure. The preferable mass ratio of sulfuric anhydride to tetrafluoroethane-β-sultone = 100:(2-10). Process is carried out preferably in device fitted with cooling jacket and stirring device under atmosphere pressure, or in the column type device fitted by dephlegmator under pressure 0.5-2.0 ati. Method provides enhancing yield of the end product.

EFFECT: improved preparing method.

4 cl, 4 ex

FIELD: medicine.

SUBSTANCE: carboxylic acid compounds are presented by formula (I) where R1 represents (1) hydrogen atom, (2) C1-4alkyl; E represents -CO-; R2 represents (1) halogen atom, (2) C1-6 alkyl, (3) trihalogen methyl; R3 represents (1) halogen atom, (2) C1-6alkyl; R4 represents (1) hydrogen atom; R5 represents (1) C1-6alkyl; represents phenyl; G represents (1) C1-6alkylene; represents 9-12-merous bicyclic heterocycle containing heteroatoms, chosen of 1-4 nitrogen atoms, one or two oxygen atoms; m represents 0 or an integer 1 to 4, n represents 0 or an integer 1 to 4, and i represents 0 or an integer 1 to 11 where R2 can be identical or different provided m is equal to 2 or more, R3 can be identical or different provided n is equal to 2 or more, and R5 can be identical or different provided i is equal to 2 or more; both R12 and R13, independently represent (1) C1-4alkyl, (2) halogen atom, (3) hydroxyl or (4) hydrogen atom, or R12 and R13 together represent (1) oxo or (2) C2-5alkylene and where provided R12 and R13 simultaneously represent hydrogen atom, carboxylic acid compound presented by formula (I), represents a compound chosen from the group including the compounds (1) - (32), listed in cl.1 of the patent claim. Besides the invention concerns a pharmaceutical composition based in the compound of formula I and to application of the compound of formula I for making the pharmaceutical composition.

EFFECT: there are produced new carboxylic acid derivatives with antagonistic activity with respect to DP receptor.

14 cl, 74 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel soluble pharmaceutical salts formed from salt-forming active compound of the general formula (I) or (II) and sugar substitute that can be used in preparing medicinal agents useful in pain and enuresis treatment. Salt-forming active substance represents a salt-forming compound among 1-phenyl-3-dimethylaminopropane compounds of the general formula (I) wherein X means -OH, F, Cl, H or group -OCOR6; R1 represents (C1-C4)-alkyl group; R2 represents H or (C1-C4)-alkyl group; R3 represents H or (C1-C4)-alkyl group with a direct chain, or R2 and R3 form in common (C4-C7)-cycloalkyl group and if R5 means H then R4 represents group O-Z in meta-position wherein Z means H,(C1-C3)-alkyl, -PO-(O-C1-C4-alkyl)2, -CO-(O-C1-C5-alkyl), -CONH-C6H4-(C1-C3-alkyl), -CO-C6H4-R7 wherein R7 represents -OCO-C1-C3-alkyl in ortho-position or group -CH2N(R8)2 in meta- or para-position and wherein R8 means (C1-C4)-alkyl or 4-morpholino-group, either R4 represents S-(C1-C3)-alkyl in meta-position, meta-Cl, meta-F, group -CR9R10R11 in meta-position wherein R9, R10 and R11 mean H or F, group -OH in ortho-position, O-(C2-C3)-alkyl in ortho-position, para-F or group -CR9R10R11 in para-position wherein R9, R10 and R11 mean H or F, or if R5 means Cl, F, group -OH or O-C1-C3-alkyl in para-position then R4 means Cl, F, group -OH or O-(C1-C3)-alkyl in meta-position, or R4 and R5 form in common group 3,4-OCH=CH- or OCH=CHO-; R6 means (C1-C3)-alkyl, or salt-forming active substance represents a salt-forming compound among 6-dimethylaminomethyl-1-phenylcyclohexane compounds of the general formula (II) wherein R1' represents H, -OH, Cl or F; R2' and R3' have similar or different values and represent H, (C1-C4)-alkyl, benzyl, -CF3, -OH, -OCH2-C6H5, O-(C1-C4)-alkyl, Cl or F under condition that at least one among radicals R2' either R3' means H; R4' represents H, -CH3, -PO-(O-C1-C4-alkyl)2, -CO-(O-C1-C5-alkyl, -CO-NH-C6H4-(C1-C3)-alkyl, -CO-C6H4-R5', CO-(C1-C5)-alkyl), -CO-CHR6'-NHR7' or unsubstituted either substituted pyridyl, thienyl, thiazolyl or phenyl group; R5' represents -OC(O)-(C1-C3)-alkyl in ortho-position or -CH2N(R8')2 in meta- or para-position and wherein R8' means (C1-C4)-alkyl, or both radicals R8' in common with nitrogen atom (N) form 4-morpholino-group, and R6' and R7' have similar or different values and represent H or (C1-C6)-alkyl under condition that if both radicals R2' and R3' represent H then R4' doesn't mean -CH3 when R1' represents additionally H, -OH or Cl, either R4' doesn't mean H when R1' represents additionally -OH. Also, invention relates to a medicinal agent based on indicated salts.

EFFECT: valuable medicinal properties of salts and drug.

14 cl, 1 tbl, 8 ex

Novel benzodioxols // 2304580

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of benzodioxol of the formula (I): wherein R1, R2, R3, R4, R5, R6, R7 and X are given in the description and the invention claim, and to their pharmaceutically acceptable salts. Also, invention relates to pharmaceutical compositions based on compounds of the formula (I) and their using for preparing medicinal agents used in treatment and/or prophylaxis of diseases associated with modulation of CB1 receptors.

EFFECT: valuable medicinal properties of compounds and pharmaceutical compositions.

19 cl, 279 ex

The invention relates to compounds of General formula I

including their optical isomers and mixtures of such isomers, where r1denotes hydrogen, C1-C6alkyl, C3-C6cycloalkyl or aryl, optionally substituted by 1-3 halogen atoms, R2and R3each independently of one another denote hydrogen or C1-C6alkyl, R4stands WITH1-C6alkyl or C3-C6quinil, R5, R6, R7and r8each denotes hydrogen and

,

r10denotes aryl, optionally substituted by 1-3 substituents selected from the group comprising halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6haloalkyl,1-WITH4haloalkoxy,1-C4alkoxy, C1-C4alkyl, C1-C6alkylthio,3-C6alkyloxy, nitro and C1-C6alkoxycarbonyl or optionally substituted heteroaryl representing aromatic kolicevo the t hydrogen, WITH1-C6alkyl or C3-C6quinil, R12denotes hydrogen or C1-C6alkyl, Z represents hydrogen,- CO-R16or-CO-COOR16and R16stands WITH1-C6alkyl, -CH2-CO - C1-C6alkyl or phenyl

FIELD: chemistry.

SUBSTANCE: invention relates to new derivatives of dibenzofuran-4,6-dicarboxylic acid of formula 1 , where: X is absent or represents a diradical, which is chosen from a group containing -O-, -S- and -NH-, R2 and R4 are independently chosen from a group which contains -H, -OH, -F, -CI, -Br, -CF3 and -CO2H, and R3 and R5 are independently chosen from a group which contains -H, -OH, -F, -Cl, -Br and -CO2H, which are extremely efficient inhibitors of amyloidogenesis, exhibit high affinity and considerably high selectivity when bonding to transthyretin (TTR) compared to the rest of plasmatic proteins and compared to control compound 1. The said compounds also increase kinetic stability of the tetrameric structure of TTR.

EFFECT: design of an effective method of inhibiting formation of amyloid fibrils.

16 cl, 11 dwg

FIELD: agriculture.

SUBSTANCE: can be used for increase of biological efficiency of insecticidal preparations on basis of entomopathogenic microorganisms. Efficiency upgrading of insecticidal preparations is reached by use of usnic acids as synergist of such insecticides. It is shown increase in percent of beer small copper caterpillars, potato bug larvas and gypsy moth caterpillars demise at usnic acid mix and entomopathogenic microorganisms use, such as fungi Metarhizium anisopliae and Beauveria bassiana (conidium), bacterium Bacillus turhingiensis (spore-crystalline mass), Baculoviridae virus nuclear polyhedrosis.

EFFECT: efficiency upgrading of insecticidal preparations.

1 cl, 3 ex, 3 tbl

FIELD: organic chemistry, analytical chemistry.

SUBSTANCE: invention relates to synthesis of novel analytical reagents of chelate-forming type. Synthesized compounds represent chelate-forming dibenzo-containing five-membered cyclic compounds comprising two symmetric β-dicarbonyl substitutes bound covalently with fluorine-containing radicals of the general formula (1): , wherein X means -CH2, oxygen (O), sulfur (S) atom, -NR; if X means -CH2 then R means hydrogen atom (H); R2 means -C(O)CH2C(O)Rf wherein Rf means -(CF2)nY wherein n = 1-6, and at n = 1 Y means H, F, Cl, Br, -OCF3, -OCH3, -OC3F7, -OCF2-CF2-OCF3, -C6F5, -C(O)OAlk wherein Alk means hydrocarbon radical; at n = 2 Y means H, F, Cl, Br, -OCF3, -OC3F7, -OCF2-CF2-OCF3, -C(O)OAlk; at n = 3, 5 or 6 Y means F, -C(O)OAlk; at n = 4 Y means H, F, Cl, -C(O)OAlk; if X means O, S or -NR then R means H or Alk, R2 means H, R1 means -C(O)CH2C(O)Rf. Invention can be used in field of luminescent-spectral analysis, in particular, for clinical diagnosis of object of biogenic origin, and in technique field for using as extractants of heavy and rare-earth metal ions for their extraction and/or purifying from their impurities of sewage and contour waters.

EFFECT: valuable medicinal and technical properties of compounds.

1 cl, 19 dwg, 19 ex

The invention relates to new derivatives of nitromethylene General formula 1 in which R represents the radical (I), (II) or (III)

The invention relates to compounds having the structural formula I, where X, Y, R and Z are defined in the description of the application

FIELD: chemistry.

SUBSTANCE: method involves asymmetric reduction of (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethyleneamine, catalytic reduction of the obtained product at temperature ranging from 40 to 100C and pH ranging from 3 to 9, propionylation of the obtained (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine, and then crystallisation from the reaction mixture.

EFFECT: obtaining optically active amine derivatives of high purity with high output and prevention of formation of by-products.

6 cl, 1 tbl, 3 ex

The invention relates to new derivatives of 4-oxobutanoic acid of formula 1, where groups a and b independently from each other selected from mono - or bicyclic aryl group selected from phenyl and naphthyl, cycloalkyl group having 5 to 8 carbon atoms, a saturated heterocyclic group selected from tetrahydrofuryl groups; group a and b may have 1 to 3 substituents selected from C1-C6alkyl group, a C1-C6alkoxygroup, halogen; or two Deputy together represent methylenedioxy

FIELD: chemistry.

SUBSTANCE: invention refers to compounds of the formula (I): , where R1 is C1-C8alkyl optionally substituted with one to three substitutes selected out of substitute group A; R2 is C1-C6alkyl or C1-C6alkoxyC1-C6alkyl; R3 is C1-C6alkyl or C1-C6alkoxy; or R2 and R3 together with adjoining carbon atoms form optionally substituted non-aromatic 5-10-member carbon ring; R4 is hydrogen; G is group represented by the formula: or the rest as provided in the invention claim; and to pharmaceutical composition, application of claimed compounds, and method of atopic dermatitis prevention or treatment.

EFFECT: novel compounds useful as atopic dermatitis treatment medication and antipruritic medicines.

24 cl, 75 ex, 290 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds with general formula (I) and its isomers, where R1 is a hydrogen atom of an alkyl C1-4 group with a straight or branched chain, or a phenyl group, thienyl group or furyl group, optionally substituted with one or more alkyl C1-4 groups with a straight or branched chain, C1-4 alkoxy groups with a straight or branched chain, or halogen atoms; R2 is a hydrogen atom or an alkyl C1-4 group with a straight or branched chain, or a phenyl, benzyl, thienyl or furyl group, optionally substituted with a methylenedioxy group, or one or more alkyl C1-4 groups with a straight or branched chain, or C1-4 alkoxy-, hydroxyl-, trifluoromethyl- or cyano-group with a straight or branched chain, or halogen atoms, as well as to a method of producing said compound. The invention also relates to new intermediates with general formula (II) and their production.

EFFECT: radioligands A3 with antagonistic action are obtained and described, labeled with iodine isotopes with mass number 125, which have high specific activity.

16 cl, 3 ex, 2 tbl, 1 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to dihydropyridine derivatives with general formula , or their pharmaceutically acceptable salts, where R1 is C1-6alkyl or phenyl, C1-5heteroaryl, both optionally substituted with one or more substitutes, chosen from hydroxy, amino, halogen, nitro, cyano; R2, R3 are independently C1-4alkyl, C1-4alkoxy group, C2-4alkenyloxy group, C3-4alkynyloxy group, halogen; R4 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkylC1-4alkyl, C6-10aryl, C6-10arylC1-4alkyl, C1-9heteroaryl, where the (hetero)aryl group is optionally substituted with one or more substitutes, chosen from hydroxy, amino, halogen, nitro, trifluoromethyl, cyano, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4alkoxy group, C1-4(di)alkylamino group, and, if R4 is a phenyl, additionally from C1-4alkylthio group, C1-4alkylsulphonyl, R5-oxycarbonyl, R5-carbonyl or R5,R6-aminocarbonyl; X is SO2, CH2, C(O) or X is absent, where X is CH2, R4 can additionally represent R5-oxycarbonyl, or R5-carbonyl; R5, R6 are independently H, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C3-6cycloakyl, C3-6cycloalylC1-4alkyl, C2-6heterocycloalkyl, C2-6heterocycloalkylC1-4alkyl, C1-4alkoxycarbonylC1-4alkyl, C1-4(di)alkylaminocarbonylC1-4alkyl or C6-10arylaminocarbonylC1-4alkyl, C1-9heteroarylaminocarbonylC1-4alkyl, C6-10aryl, C1-9heteroaryl, C6-10arylC1-4alkyl, C1-9heteroarylC1-4alkyl, where the (hetero)aryl group is optionally substituted with one or more substitutes, chosen from hydroxy, amino, halogen, nitro, trifluoromethyl, cyano, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4alkoxy group, C1-4(di)alkylamino group or R5, R6 in R5, R6- aminocarbonyl group can be bonded to a C2-6heterocycloalkyl ring, as well as to a pharmaceutical composition with antagonistic activity towards FSH receptor and to use of these compounds for making medicinal agents.

EFFECT: compounds which are suitable for treating fertility disorders are obtained and described.

11 cl, 33 ex

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