Iminopyridine derivatives and use thereof as microbiocides

FIELD: chemistry.

SUBSTANCE: invention relates to a method of controlling infection of useful plants with phytopathogenic microorganisms or prevention thereof, wherein a compound of formula I or a composition thereof, which contains said compound as an active ingredient, is deposited on plants, on a parts thereof or place where said plants grow, where the compound of formula I is substitutes are as defined in claim 1.

EFFECT: obtaining a compound for controlling infection of useful plants with phytopathogenic microorganisms.

26 cl, 2 tbl, 8 ex

 

The present invention relates to new microbicide active, in particular, fungicide active pyridylamine. The present invention also relates to intermediate products used in obtaining these compounds, to compositions which contain these compounds, and to their use in agriculture or horticulture to combat the infestation of plants by phytopathogenic microorganisms, preferably fungi, or warnings.

Some derivatives of phenylaniline proposed in the literature as Microbiocide active ingredients in pesticides. For example, in WO 00/46184 and WO 03/093224 revealed phenylaniline applicable as fungicides. However, the biological properties of these known compounds is not entirely satisfactory to combat the infestation of plants by phytopathogenic microorganisms or warnings, so the need for new compounds that have microbiocidal ability. According to the invention, we have discovered new pyridylamine with microbiocidal activity.

Therefore, the present invention relates to compounds of formula I

in which

aa) R1and R2independently of one another represent hydrogen, cyano, formyl, nitro-group, With1-C7alkyl, C2-C6Ala the Nile, With2-C6quinil,2-C7alkylsulphonyl,3-C7alkenylboronic,4-C9cycloalkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, C2-C7alkylsulphonyl-C1-C6alkyl, C3-C6alkenylacyl-C1-C6alkyl, C3-C6alkyloxy-C1-C6alkyl, benzyloxy-C1-C6alkyl, C3-C8cycloalkyl-C1-C6alkyl, C2-C7allyloxycarbonyl,4-C7alkenylacyl,4-C7alkyloxyaryl,4-C9cycloalkylcarbonyl, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylsulfonyl or C1-C6halogenacetylenes; or

ab) R1and R2independently of one another denote-Si(R51)(R52)(R53), where R51, R52, R53independently of one another represent halogen, cyano, C1-C6alkyl, C2-C6alkenyl,3-C8cycloalkyl,5-C8cycloalkenyl,2-C6quinil, C1-C6alkoxygroup, benzyl or phenyl; or

ac) R1and R2independently of one another denote-Si(OR54)(OR55)(OR56), where R54, R55, 56independently of one another denote C1-C6alkyl, C3-C6alkenyl,3-C8cycloalkyl,3-C6quinil, benzyl or phenyl; or

ad) R1and R2independently of one another denote phenylsulfonyl, phenylsulfinyl, phenylcarbinol, phenoxycarbonyl, benzyl, benzylcarbamoyl or benzyloxycarbonyl; or

ae) R1and R2independently of one another denote phenylsulfonyl, phenylsulfinyl, phenylcarbinol, phenoxycarbonyl, benzyl, benzylcarbamoyl, benzyloxycarbonyl, mono - or politeley

ae1) substituents, independently selected from the group comprising a hydroxy-group, mercaptopropyl, halogen, cyano, azide group, a nitrogroup, SF5, an amino group, a C1-C6alkyl, C1-C6halogenated,3-C8cycloalkyl,3-C8halogenosilanes,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil,2-C6halogenoalkanes, C1-C6alkoxygroup,1-C6halogenlampe,1-C6alkoxyl1-C6alkyl, C1-C6alkylthio1-C6alkyl, C3-C6alkenylacyl,3-C6halogenaryloxy,3-C6alkyloxy, C1-C6allylthiourea, C1-C6 halogenation, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, benzyloxy, fenoxaprop, benzyl and phenyl, where benzyloxy, fenoxaprop, benzyl and phenyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

e) substituents, independently selected from the group comprising carboxypropyl, -C(=O)-Cl, -C(=O)-F, C2-C7alkoxycarbonyl,2-C7alkylthiomethyl,2-C7halogenosilanes,3-C7alkenylacyl,3-C7gelegenheitsarbeit,3-C7alkyloxyaryl, benzyloxycarbonyl and phenoxycarbonyl where benzyloxycarbonyl and phenoxycarbonyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

e) substituents, independently selected from the group include formyl, C2 -C7alkylsulphonyl,2-C7halogenoalkanes,3-C7alkenylboronic, phenylcarbinol and benzylcarbamoyl where phenylcarbinol and benzylcarbamoyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

e) substituents, independently selected from the group comprising aminosulfonyl, C1-C6alkylaminocarbonyl, N,N-di(C1-C6alkyl)-aminosulfonyl, -C(=O)NR57R58, -C(=S)NR57R58and-NR57R58where R57and R58independently of one another denote hydrogen, C1-C6alkyl, C1-C6halogenated,3-C6alkenyl,3-C6halogenoalkanes,3-C6quinil,3-C8cycloalkyl,3-C8halogenosilanes, phenyl or benzyl, where phenyl, benzyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup, or R57and R58together with the atom connecting them estabrished aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group, thiomorpholine group, each of which, in turn, may be mono - or polyamidine substituents selected from the group comprising methyl, halogen, cyano and nitro-group; and the substituents at nitrogen atoms in the ring systems do not represent a halogen; or

af) R1or R2means

af1) a hydroxy-group, an amino group, a C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation,3-C6alkyloxy or benzyloxy; or

af2) C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation,3-C6alkyloxy, benzyloxy, mono - or polyamidine substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6halogenlampe; or

ag) R1and R2independently of one another denote With1-C7al the sludge, With2-C6alkenyl,2-C6quinil,2-C7alkylsulphonyl,3-C7alkenylboronic,4-C9cycloalkylcarbonyl,1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, C3-C6alkenylacyl-C1-C6alkyl, C2-C6alkylsulphonyl-C1-C6alkyl, C3-C6alkyloxy-C1-C6alkyl, benzyloxy-C1-C6alkyl, C3-C8cycloalkyl-C1-C6alkyl, C2-C7allyloxycarbonyl,4-C7alkenylacyl,4-C7alkyloxyaryl or4-C9cycloalkylcarbonyl, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, azide group, a C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6halogenlampe, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C2-C7alkoxycarbonyl, formyl, C2-C7alkylsulphonyl, -Si(R51)(R52)(R53and-Si(OR54)(OR55)(OR56); or

ah) R1and R2independently of one another denote a group of A-;

DG is And denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system, which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine

A1) substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, the nitro-group, azide group, formyl, carboxylate, -C(=O)-Cl, =O, =S, -C(=O)-F, C1-C6alkyl, C2-C6alkenyl,2-C6quinil,3-C8cycloalkyl, C5-C8cycloalkenyl,5-C8cycloalkenyl, C1-C6halogenated,2-C6halogenoalkanes,2-C6halogenoalkanes,3-C8halogenosilanes,5-C8halogennitroalkanes,5-C8halogennitroalkanes, C1-C6alkoxygroup, C1-C6halogenlampe,3-C6alkenylacyl,3-C6halogenaryloxy,3-C6alkyloxy,3-C8cycloalkylation,3-C8halogennitroalkanes,3-C8cycloalkanones,3-C8halogennitroalkanes, is enteroctopus and fenoxaprop, where benzyloxy and fenoxaprop, in turn, can be mono - or polyamideimide substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, azide group, an amino group, -SF5C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6halogenlampe, C1-C6alkoxyl1-C6alkyl, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

A2) substituents, independently selected from the group including HC(=NOR59)-, (C1-C6alkyl)C(=NOR59)-, (C1-C6halogenated)C(=NOR59)-, (C1-C6alkyl)C(=NOR59)1-C6alkyl - and (C1-C6halogenated)C(=NOR59)C1-C6alkyl-, where R59denotes hydrogen, C1-C6alkyl, C1-C6halogenated,3-C6alkenyl,3-C6halogenoalkanes,3-C6quinil,3-C8cycloalkyl,3-C8halogenosilanes, benzyl and phenyl, and benzyl, and phenyl, mono - or politeley halogen, cyano, hydroxy-group, C1-C6the alkyl, C1-C6halogenation or1-C6alkoxygroup; or

A3) substituents, n is dependent selected from the group including C1-C6allylthiourea, C1-C6halogenation, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, (R14)S(=O)(=NR13)- and (R14)(R15)S(=O)=N-, where R13denotes hydrogen, C1-C6alkyl, C1-C6halogenated,3-C6alkenyl,3-C6halogenoalkanes,3-C6quinil,3-C8cycloalkyl,3-C8halogenosilanes, phenyl or benzyl, or represents phenyl or benzyl, mono - or politeley halogen, cyano, hydroxy-group, C1-C6the alkyl, C1-C6halogenation or C1-C6alkoxygroup, and R14and R15independently of one another denote C1-C6alkyl, C3-C8cycloalkyl, C1-C6halogenated,3-C8halogenosilanes,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil, benzyl or phenyl, or benzyl or phenyl, independently of one another containing substituents selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

A4) substituents, independently selected from the group comprising-NR57R58, -C(=O)NR57R58and-C(=S)NR57R 58; or

A5) substituents, independently selected from the group include formyl, C2-C7alkylsulphonyl,2-C7halogenoalkanes,3-C7alkenylboronic,3-C7halogenoalkanes,4-C9cycloalkylcarbonyl,4-C9halogencycloprapanes,2-C7alkoxycarbonyl,2-C7halogenosilanes,3-C7alkenylacyl,3-C7alkyloxyaryl,4-C9cycloalkylcarbonyl,2-C7alkylthiomethyl and benzyloxycarbonyl, and benzyloxycarbonyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

A6) substituents, independently selected from the group comprising-Si(R51)(R52)(R53and-Si(OR54)(OR55)(OR56); or

A7) substituents, independently selected from the group comprising aminosulfonyl, (C1-C6alkyl)aminosulfonyl, N,N-di(C1-C6alkyl)-aminosulfonyl, di(C1-C6alkyl)amino group, (C1-C6alkyl)amino, phenyl, fenoxaprop, benzyl and benzyloxy, where phenyl, fenoxaprop, benzyl and benzyloxy, in the howling of all, may be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, an amino group, a nitro-group, azide group, mercaptopropyl, formyl, -SF5C1-C6alkyl, C1-C6halogenated,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil, C1-C6alkoxygroup, C1-C6halogenlampe,1-C6allylthiourea,1-C6halogenation,3-C6altertekhnogrupp,3-C6halogeenilamppu,3-C6alinytjara,1-C3alkoxy-C1-C3allylthiourea,2-C6alkylsulphonyl-C1-C3allylthiourea,2-C6alkoxycarbonyl-C1-C6allylthiourea, cyano-C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, aminosulfonyl, (C1-C6alkyl)aminosulfonyl, N,N-di(C1-C6alkyl)aminosulfonyl, di(C1-C6alkyl)amino group and (C1-C6alkyl)amino group; or

ai) R1and R2independently of one another represent-C(=O)NR57R58; or

aj R 1and R2together form2-C6Allenby bridge, which may be mono - or polyamidine halogen, cyano, C1-C6alkyl or C1-C6halogenoalkanes groups; or

ak) R1and R2together with the connecting nitrogen atom of form pyrazolinone group, pyrazolidine group, pyrrolidone group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, morpholino group, thiomorpholine group, each of which independently of one another may be mono - or polyamidine methyl groups, halogen, cyano and nitro-group; or

al) fragment

can be a

,,,,

,,,,,

or;

where each of these fragments may be mono - or polyamidine substituents, independently selected from the group comprising halogen, cyano, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup the u;

ba) R3, R4and R7independently of one another denote

ba1) hydrogen, halogen, a cyano, a nitro-group, mercaptopropyl, the hydroxy-group, azide group, SF5, -NR64R65where R64and R65independently of one another denote hydrogen, C1-C6alkyl, C1-C6halogenated,3-C6alkenyl,3-C6halogenoalkanes,3-C6quinil,3-C8cycloalkyl,3-C8halogenosilanes, phenyl or benzyl, where phenyl, benzyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup, or R64and R65together with the connecting nitrogen atom of form aziridine group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group, thiomorpholine group, each of which, in turn, may be mono - or polyamidine substituents selected from the group comprising methyl, halogen, ziang is the SCP and the nitro-group; and the substituents at nitrogen atoms in the ring systems do not represent a halogen; or R3, R4and R7independently of one another represent-C(=S)NH2, -N=C=O, -N=C=S, amino group, (R51)(R52)(R53Si-, (R51)(R52)(R53)Si-(C1-C6alkyl)-, (R51)(R52)(R53)Si-(C2-C6quinil)-, (OR54)(OR55)(OR56Si - or (OR214)(OR215)(OR216)Si-(C1-C6alkyl)-; where R214, R215and R216independently of one another represent halogen, cyano, C1-C6alkyl, C2-C6alkenyl,3-C8cycloalkyl,5-C8cycloalkenyl,2-C6quinil, benzyl or phenyl;

or R3, R4and R7independently of one another denote

ba2) C1-C6allylthiourea,1-C6alkylsulfonyl,1-C6alkylsulfonyl, C1-C6halogenation,1-C6halogenacetylenes,1-C6halogenallylacetic, aminosulfonyl, aminosulfonyl, C1-C6alkoxygroup, C1-C6halogenlampe,3-C6alkenylacyl,3-C6halogenaryloxy,3-C6alkyloxy, (C1-C6alkyl)aminosulfonyl, di(C1-C6alkyl)aminosulfonyl,1 6alkoxygroup,2-C6alkenylacyl,2-C6alkyloxy,1-C6alkyl-S(=O)(R14)=N-, (R14)S(=O)(=N-R13)-, (R14)(R15)S(=O)=N-, -S-C3-C6alkenyl, -S-C3-C6-quinil, -S-C3-C8-cycloalkyl, S-benzyl, or-S-C3-C6alkenyl, -S-C3-C6-quinil, -S-C3-C8-cycloalkyl or S-benzyl; each of which may be mono - or polyamidine substituents selected from the group comprising halogen, cyano, C1-C6-alkyl, C1-C6-halogenated, C1-C6-alkoxygroup;

or R3, R4and R7independently of one another denote

ba3) C1-C6alkyl, C2-C6alkenyl or2-C6quinil, or C1-C6alkyl, C2-C6alkenyl or2-C6quinil, mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, mercaptopropyl, a cyano, a nitro-group, C1-C6alkyl, C1-C6halogenated,1-C6alkoxygroup, C1-C6hydroxyalkyl, three(alkyl)silyl, C1-C6halogenlampe,1-C6allylthiourea,1-C6halogenation, C1-C6alkylsulfonyl, C1-C6g is legendkiller, C1-C6alkylsulfonyl and C1-C6halogenallylacetic;

or R3, R4and R7independently of one another denote

ba4) formyl, C2-C7alkoxycarbonyl,2-C7halogenosilanes,3-C7alkenylacyl,3-C7gelegenheitsarbeit,2-C7alkylsulphonyl, carboxypropyl, -C(=O)-Cl, -C(=O)-F, C2-C7halogenoalkanes,3-C7alkenylboronic or3-C7halogenoalkanes; or R3, R4and R7independently of one another denote

ba5) phenyl, fenoxaprop, benzyl or benzyloxy, or fenoxaprop, benzyl or benzyloxy, mono - or polyamidine substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, azide group, an amino group, -SF5C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup,1-C6halogenlampe, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

bb) R3, R4and R7independently of one another denote a group-, And-O - or A-(C1-C6alkyl)-, where group a is as defined above in section ah);

CA) R5 denotes hydrogen, C1-C12alkyl, C2-C12alkenyl,2-C12quinil, C1-C12alkylsulfonyl, C2-C12alkanesulfonyl, phenylsulfonyl or bansilalpet, or denotes a C1-C12alkyl, C2-C12alkenyl,2-C12quinil,1-C12alkylsulfonyl, C2-C12alkanesulfonyl, phenylsulfonyl or bansilalpet, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, azide group, formyl, C2-C7alkylsulphonyl,2-C7halogenoalkanes, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6halogenlampe, C1-C6allylthiourea,1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

cb1) R5denotes formyl, C2-C12alkylsulphonyl,3-C12alkenylboronic,3-C12alkenylboronic,4-C12cycloalkylcarbonyl, benzylcarbamoyl, phenylcarbinol,2-C12alkoxycarbonyl,4-C12alkenylacyl,4-C12alkyloxyaryl,4-C12cycloalkylcarbonyl, benzyloxycarbonyl or phenoxycarbonyl or means

cb2)2-C12alkylsulphonyl,3-C12alkenylboronic,3-C12alkenylboronic,4-C12cycloalkylcarbonyl, benzylcarbamoyl, phenylcarbinol,2-C12alkoxycarbonyl,4-C12alkenylacyl,4-C12alkyloxyaryl,4-C12cycloalkylcarbonyl, benzyloxycarbonyl or phenoxycarbonyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

SS) R5means (R51)(R52)(R53Si-, (R51)(R52)(R53)Si-(C1-C12alkyl)-, (R51)(R52)(R53)Si-(C3-C8cycloalkyl)-, (R54O)(R55O)(R56O)Si, (R54O)(R55O)(R56O)Si-(C1-C12alkyl)- or (R54O)(R55O)(R56O)Si-(C3-C8cycloalkyl)-; or

cd) R5stands With1-C6alkyl-b-C1-C12alkyl, C2-C6alkenyl-b-C1-C12alkyl, C2-C6quinil-b-C1-C12alkyl, C3-C8cycloalkyl-b-C1-C12alkyl-, benzyl-B-C1-C12alkyl-, phenyl-b-C1-C12alkyl, C1-C6alkyl-b-C2-C12alkenyl-From2-C6al is enyl-b-C 2-C12alkenyl-From2-C6quinil-b-C2-C12alkenyl-From3-C8cycloalkyl-b-C2-C12alkenyl-, benzyl-b-C2-C12alkenyl-, phenyl-b-C2-C12alkenyl-, C1-C6alkyl-b-C2-C12quinil-From2-C6alkenyl-b-C2-C12quinil-From2-C6quinil-b-C2-C12quinil-From3-C8cycloalkyl-b-C2-C12quinil-, benzyl-b-C2-C12quinil-, phenyl-b-C2-C12quinil-From1-C6alkyl-b-C3-C8cycloalkyl-From2-C6alkenyl-b-C3-C8cycloalkyl-From2-C6quinil-b-C3-C8cycloalkyl-From3-C8cycloalkyl-b-C3-C8cycloalkyl-, benzyl-b-C3-C12cycloalkyl - or phenyl-b-C3-C12cycloalkyl-where group refers to-S(=O)-, -C(=S)-, -C(=NOR59)-, -C(R60)=NO-, -ON=C(R60)-, -O-C(=O)-, -C(=O)-O-, -O-, -S-, -S(=O)-, -S(=O)2-, -S(=O)(=NR13)-, -S(=O)(R14)=N-, -N=S(=O)(R14)-, -N(R62)-C=O)-, -C=O)-N(R62)-, -N(R62)-SO2- or-SO2-N(R62)-;

cd1) where R60denotes hydrogen, C1-C6alkyl, C3-C8cycloalkyl, C1-C6halogenated,3-C8halogenosilanes,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil, Benz is l or phenyl, or benzyl or phenyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup, and

cd2) R62denotes hydrogen, C1-C6alkyl, C3-C8cycloalkyl, C1-C6halogenated,3-C8halogenosilanes,3-C6alkenyl,3-C6quinil, benzyl or phenyl, or benzyl or phenyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or

ce) R5stands With1-C6alkyl-b-C1-C12alkyl, C2-C6alkenyl-b-C1-C12alkyl, C2-C6quinil-b-C1-C12alkyl, C3-C8cycloalkyl-b-C1-C12alkyl-, benzyl-b-C1-C12alkyl-, phenyl-b-C1-C12alkyl, C1-C6alkyl-b-C2-C12alkenyl-From2-C6alkenyl-b-C2-C12alkenyl-From2-C6quinil-b-C2-C12alkenyl-From3-C8cycloalkyl-b-C2-C12alkenyl-, benzyl-b-C2-C12alkenyl-, phenyl-b-C2-C12alkenyl-, 1-C6alkyl-b-C2-C12quinil-From2-C6alkenyl-b-C2-C12quinil-From2-C6quinil-b-C2-C12quinil-From3-C8cycloalkyl-b-C2-C12quinil-, benzyl-b-C2-C12quinil-, phenyl-b-C2-C12quinil-From1-C6alkyl-b-C3-C8cycloalkyl-From2-C6alkenyl-b-C3-C8cycloalkyl-From2-C6quinil-b-C3-C8cycloalkyl-From3-C8cycloalkyl-b-C3-C8cycloalkyl-, benzyl-b-C3-C12cycloalkyl-, phenyl-b-C3-C12cycloalkyl-, each of which, in turn, contains substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, mercaptopropyl, C1-C6halogenated, C1-C6alkoxygroup, formyl, C2-C6alkylsulphonyl, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

cf) R5refers to A-, And-(C1-C6alkyl)-, And-O-(C1-C6alkyl)-, And-(C2-C6alkenyl)-, And-O-(C2-C6alkenyl)-, And-(C2-C6-quinil)-, And-O-(C2-C6quinil)-, And-(C3-C8cycloalkyl)- or a-O-(C3-C8cycloalkyl)-; where group a is as defined above in section the ah); or

cg) R5refers to a group-N=C(R8R9;

cg1) where R8and R9independently of one another denote hydrogen, halogen, cyano, C1-C12alkyl, C2-C12alkenyl,2-C12quinil,1-C12alkoxygroup, formyl, C2-C12alkylsulphonyl,3-C12alkenylboronic, carboxypropyl,2-C12alkoxycarbonyl or4-C12alkenylacyl, or C1-C12alkyl, C2-C12alkenyl,2-C12quinil,1-C12alkoxygroup,2-C12alkylsulphonyl,3-C12alkenylboronic,2-C12alkoxycarbonyl or4-C12alkenylacyl, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6halogenlampe, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

cg2) R8and R9together form2-C8Allenby bridge, which optionally may be mono - or polyamidine substituents, independently selected from the group comprising halogen, tzia is Gruppo, C1-C6alkyl and C1-C6halogenated; or

cg3) R8and R9independently of one another denote a group-, And-O - or A-(C1-C6alkyl)-; where group a is as defined above in section ah);

d) R6denotes hydrogen, halogen, cyano, formyl, C1-C6alkyl, C1-C6halogenated, -SH, -S-C1-C6alkyl, -S-C1-C6halogenated, -S-C1-C6halogenated,2-C6alkenyl,2-C6halogenoalkanes or2-C6quinil;

and agronomically acceptable salts/complexes with metals/complexes with metalloids/isomers/structural isomers/stereoisomers/diastereoisomers/enantiomers/tautomers/N-oxides of these compounds.

The substituents at the nitrogen atom are never free. Hydroxy-, mercapto - or amino substituents are not the atom of carbon in α-position to the heteroatom of the main fragment.

The alkyl groups contained in the definitions of the substituents may have a linear or branched chain and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl and their branched isomers. CNS, alkeline and alkyline radicals formed from the above alkyl, RA is Ikhlov. Alkeneamine and alkyline groups may be mono - or polyunsaturated.

Cycloalkyl group contained in the definitions of substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Halogen usually means fluorine, chlorine, bromine or iodine, preferably fluorine, bromine or chlorine. This also applies to combinations of halogen with other values, such as halogenated or halogenlampe.

Halogenoalkane groups preferably contain in the chain from 1 to 4 carbon atoms. Halogenated represents, for example, vermeil, deformity, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-triptorelin, 2-foretel, 2-chloroethyl, pentafluoroethyl, 1,1-debtor-2,2,2-trichloroethyl, 2,2,3,3-tetraborate or 2,2,2-trichloroethyl; preferably trichloromethyl, diperchlorate, deformity, trifluoromethyl or dichloromethyl.

Suitable halogenoalkane groups are alkeneamine group, which mono - or polyamidine halogen, halogen is fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine, for example 2,2-debtor-1-methylvinyl, 3-forproper, 3-chloropropionyl, 3-bromopropionyl, 2,3,3-triptocaine, 2,3,3-trichlorpropane and 4,4,4-triflorum-2-EN-1-yl.

Suitable halogenalkyls groups are, for example, alkyline group, which mono - or polyamidine what alogena, halogen is bromine, iodine, preferably fluorine and chlorine, for example, 3-forproposal, 3-chloropropionyl, 3-bromopropyl, 3,3,3-triptocaine and 4,4,4-triflorum-2-in-1-yl.

Alkoxygroup represents, for example, a methoxy group, ethoxypropan, propoxylate, isopropoxy, n-butoxypropyl, isobutoxy, sec-butoxypropyl and tert-butoxypropan; preferably the methoxy group and ethoxypropan. Halogenlampe represents, for example, formatexpr, dipterocarp, cryptometer, 2,2,2-triptracker, 1,1,2,2-tetrafluoroethoxy, 2-floridacheap, 2-chlorethoxyfos, 2,2-dipterocarp and 2,2,2-trichlorethene; preferably dipterocarp, 2-choreograph and cryptometer.

Alkoxycarbonyl represents, for example, methoxycarbonyl, etoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxide, second-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or etoxycarbonyl. Halogenlampe preferably contain in the chain of 1 to 6 carbon atoms. Halogenlampe represents, for example, formatexpr, dipterocarp, cryptometer, 2,2,2-triptracker, 1,1,2,2-tetrafluoroethoxy, 2-floridacheap, 2-chlorethoxyfos, 2,2-deflorate is the system of groups and 2,2,2-trichlorethene; preferably dipterocarp, 2-choreograph and cryptometer. Ancilliary preferably contain in the chain of 1 to 6 carbon atoms.

Alkoxyalkyl represents, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxyphenyl or isopropoxide.

Allylthiourea represents, for example, methylthiourea, ethylthiourea, PropertyGroup, isopropylthio, n-butylthiourea, isobutylthiazole, sec-butylthiourea or tert-butylthiourea, preferably metalcorp and ethylthiourea. Alkylsulfonyl represents, for example, methylsulfinyl, ethylsulfinyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl, tert-butylsulfonyl; preferably methylsulfinyl and ethylsulfinyl. Alkylsulfonyl is, for example, methylsulphonyl, ethylsulfonyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl; preferably methylsulphonyl or ethylsulfonyl.

With2-C6Alkylsulphonyl represents, for example, methylcarbamyl, ethylcarboxyl, propylmalonic, isopropylcarbonate, n-butylcarbamoyl, isobutylketone, second-butylcarbamoyl, tert-butylcarbamoyl or n-internabonal and the x branched isomers, preferably methylcarbamyl and ethylcarboxyl. Galogenirovannyie radicals formed from the above alkyl radicals.

In the context of the present invention the expression "mono - or politeley"contained in the definitions of the substituents, depending on the chemical structure of the substituents usually means from mono - to emiratesunited, preferably mono - to petiteteenager, more preferably mono-, di - or tizamidine.

In the context of the present invention 3-10-membered monocyclic or condensed bicyclic ring system, which may be partially saturated or fully saturated, depending on the number of ring elements, for example, selected from the group including

,,,,,

,,,,

,,,,,

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where these cycloalkyl group, in turn, can be preferably nezamedin the mi or substituted C 1-C6by alkyl or halogen, or denotes phenyl, benzyl, naphthyl or heterocyclic groups: pyrrolyl; pyridyl; pyrazolyl; pyrimidyl; pyrazinyl; imidazolyl; thiadiazolyl; hintline; furyl; oxadiazolyl; indolizinyl; pyranyl; isobenzofuranyl; thienyl; naphthyridine; (1-methyl-1H-pyrazole-3-yl)-; (1-ethyl-1H-pyrazole-3-yl)-; (1-propyl-1H-pyrazole-3-yl)-; (1H-pyrazole-3-yl)-; (1,5-dimethyl-1H-pyrazole-3-yl)-; (4-chloro-1-methyl-1H-pyrazole-3-yl)-; (1H-pyrazole-1-yl)-; (3-methyl-1H-pyrazole-1-yl)-; (3,5-dimethyl-1H-pyrazole-1-yl)-; (3-isoxazolyl)-; (5-methyl-3-isoxazolyl)-; (3-methyl-5-isoxazolyl)-; (5-isoxazolyl)-; (1H-pyrrol-2-yl)-; (1-methyl-1H-pyrrol-2-yl)-; (1H-pyrrol-1-yl)-; (1-methyl-1H-pyrrol-3-yl)-; (2-furanyl)-; (5-methyl-2-furanyl)-; (3-furanyl)-; (5-methyl-2-thienyl)-; (2 thienyl)-; (3-thienyl)-; (1-methyl-1H-imidazol-2-yl)-; (1H-imidazol-2-yl)-; (1-methyl-1H-imidazol-4-yl)-; (1-methyl-1H-imidazol-5-yl)-; (4-methyl-2-oxazolyl)-; (5-methyl-2-oxazolyl)-; (2-oxazolyl)-; (2-methyl-5-oxazolyl)-; (2-methyl-4-oxazolyl)-; (4-methyl-2-thiazolyl)-; (5-methyl-2-thiazolyl)-; (2-thiazolyl)-; (2-methyl-5-thiazolyl)-; (2-methyl-4-thiazolyl)-; (3-methyl-4-isothiazolin)-; (3-methyl-5-isothiazole)-; (5-methyl-3-isothiazole)-; (1-methyl-1H-1,2,3-triazole-4-yl)-; (2-methyl-2H-1,2,3-triazole-4-yl)-; (4-methyl-2H-1,2,3-triazole-2-yl)-; (1-methyl-1H-1,2,4-triazole-3-yl)-; (1,5-dimethyl-1H-1,2,4-triazole-3-yl)-; (3-methyl-1H-1,2,4-triazole-1-yl)-; (5-methyl-1H-1,2,4-triazole-1-yl)-; (4,5-dimethyl-4H-1,2,4-triazole-3-yl)-; (4-methyl-4H-1,2,4-Tr the azole-3-yl)-; (4H-1,2,4-triazole-4-yl)-; (5-methyl-1,2,3-oxadiazol-4-yl)-; (1,2,3-oxadiazol-4-yl)-; (3-methyl-1,2,4-oxadiazol-5-yl)-; (5-methyl-1,2,4-oxadiazol-3-yl)-; (4-methyl-3-furutani)-; (3-furutani)-; (5-methyl-1,2,4-oxadiazol-2-yl)-; (5-methyl-1,2,3-thiadiazole-4-yl)-; (1,2,3-thiadiazole-4-yl)-; (3-methyl-1,2,4-thiadiazole-5-yl)-; (5-methyl-1,2,4-thiadiazole-3-yl)-; (4-methyl-1,2,5-thiadiazole-3-yl)-; (5-methyl-1,3,4-thiadiazole-2-yl)-; (1-methyl-1H-tetrazol-5-yl)-; (1H-tetrazol-5-yl)-; (5-methyl-1H-tetrazol-1-yl)-; (2-methyl-2H-tetrazol-5-yl)-; (2-ethyl-2H-tetrazol-5-yl)-; (5-methyl-2H-tetrazol-2-yl)-; (2N-tetrazol-2-yl)-; (2-pyridyl)-; (6-methyl-2-pyridyl)-; (4-pyridyl)-; (3-pyridyl)-; (6-methyl-3-pyridazinyl)-; (5-methyl-3-pyridazinyl)-; (3-pyridazinyl)-; (4,6-dimethyl-2-pyrimidinyl)-; (4-methyl-2-pyrimidinyl)-; (2-pyrimidinyl)-; (2-methyl-4-pyrimidinyl)-; (2-chloro-4-pyrimidinyl)-; (2,6-dimethyl-4-pyrimidinyl)-; (4-pyrimidinyl)-; (2-methyl-5-pyrimidinyl)-; (6-methyl-2-pyrazinyl)-; (2-pyrazinyl)-; (4,6-dimethyl-1,3,5-triazine-2-yl)-; (4,6-dichloro-1,3,5-triazine-2-yl)-; (1,3,5-triazine-2-yl)-; (4-methyl-1,3,5-triazine-2-yl)-; (3-methyl-1,2,4-triazine-5-yl)-; (3-methyl-1,2,4-triazine-6-yl)-;

,,,

,,,,,,,,,

,,,,,,,,

,,,,,

,,,,,

,,,,,

and,

where each R26denotes methyl, each of R27and each of R28independently represent hydrogen, C1-C3alkyl, C1-C3alkoxy is to Rupp, C1-C3allylthiourea or trifluoromethyl, X4denotes oxygen or sulfur, and r=1, 2, 3, or 4.

If these definitions do not specify a free valency, for example, as in, the place of attachment is the carbon atom marked as "CH", or in this case, as, for example,the position of the connection, indicated at the bottom left.

The preferred compounds are those in which

ba) R3, R4and R7independently of one another denote

ba1) hydrogen, halogen, a cyano, a nitro-group, mercaptopropyl, the hydroxy-group, azide group, SF5, -N=C=O, -N=C=S, amino group, (R51)(R52)(R53Si-, (R51)(R52)(R53)Si-(C1-C6alkyl)-, (R51)(R52)(R53)Si-(C2-C6quinil)-, (OR54)(OR55)(OR56Si - or (OR214)(OR215)(OR216)Si-(C1-C6alkyl)-, where R214, R215and R216independently of one another represent halogen, cyano, C1-C6alkyl, C2-C6alkenyl,3-C8cycloalkyl,5-C8cycloalkenyl,2-C6quinil, benzyl or phenyl; or R3, R4and R7independently of one another denote

ba2)1-C6allylthiourea,1-C6alkylsulfonyl,1-C61-C6halogenation,1-C6halogenacetylenes,1-C6halogenallylacetic, aminosulfonyl, (C1-C6alkyl)aminosulfonyl, di(C1-C6alkyl)aminosulfonyl, C1-C6alkyl-S(=O)(R14)=N-, (R14)S(=O)(=N-R13)- or (R14)(R15)S(=O)=N-; or R3, R4and R7independently of one another denote

ba3) C1-C6alkyl, C2-C6alkenyl or2-C6quinil, or C1-C6alkyl, C2-C6alkenyl or2-C6quinil, mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, mercaptopropyl, a cyano, a nitro-group, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6hydroxyalkyl, three(alkyl)silyl,1-C6halogenlampe,1-C6allylthiourea,1-C6halogenation, C1-C6alkylsulfonyl, C1-C6halogenacetylenes,1-C6alkylsulfonyl and C1-C6halogenallylacetic; or R3, R4and R7independently of one another denote

ba4) formyl, C2-C7alkoxycarbonyl,2-C7halogenosilanes,3-C7alkenyl dicarbonyl, With3-C7gelegenheitsarbeit,2-C7alkylsulphonyl, carboxypropyl, -C(=O)-Cl, -C(=O)-F, C2-C7halogenoalkanes,3-C7alkenylboronic or3-C7halogenoalkanes; or R3, R4and R7independently of one another denote

ba5) phenyl, fenoxaprop, benzyl or benzyloxy, or fenoxaprop, benzyl or benzyloxy, mono - or polyamidine substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, a hydroxy-group, mercaptopropyl, azide group, an amino group, -SF5C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup, C1-C6halogenlampe,1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or

bb) R3, R4and R7independently of one another denote a group-, And-O - or A-(C1-C6alkyl)-, where group a is as defined above in section ah);

d) R6denotes hydrogen, halogen, cyano, formyl, C1-C6alkyl, C1-C6halogenated,2-C6alkenyl,2-C6halogenoalkanes or2-C6quinil; and agronomically acceptable salts/complexes with metals/complexes with metalloids/Isom the market/structural isomers/stereoisomers/diastereoisomers/enantiomers/tautomers/N-oxides of these compounds.

In a preferred group of compounds R1and R2independently of one another represent hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxygroup; or R1and R2together form2-C6Allenby bridge, which may be mono - or polyamidine metal groups; or R1and R2together with the connecting nitrogen atom of form pyrazolinone group, pyrazolidine group, pyrrolidone group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, morpholino group, thiomorpholine group, each of which independently of one another may be mono - or polyamidine metal groups; or

R1denotes hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polysome the military deputies, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxy and R2denotes a hydroxy-group, an amino group, a C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation or3-C6alkyloxy; or

R2denotes hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxy and R1denotes a hydroxy-group, an amino group, a C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation or3-C6alkyloxy.

Other preferred compounds of formula I are those in which

R6denotes hydrogen, fluorine, chlorine, bromine, cyano, C1-C6alkyl, C1-C6halogenated or SNO;

R7denotes hydrogen, C1-C6-alkyl, C1-C6-halogena the sludge, halogen or cyano;

R4denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated,3-C7cycloalkyl, halogen, cyano, hydroxy-group, C1-C6alkoxygroup, amino group, azide group, mercaptopropyl, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, SNO,2-C7alkylsulphonyl, aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group, thiomorpholine group; or aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group, thiomorpholine group, each of which, in turn, is mono - or polyamidine substituents selected from the group comprising methyl, halogen; or R4denotes phenyl or phenyl which is mono - or polyamidine substituents, independently selected from the group VK is causa halogen, a cyano, a hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup;

R3denotes hydrogen, C1-C6-alkyl, C2-C6alkenyl,2-C6quinil,3-C7cycloalkyl, halogen, cyano, azide group, a nitro-group, -N=C=O, -N=C=S, -C(=O)NH2, -C(=S)NH2, -C(=O)NH(CH3), -C(=S)NH(CH3), -C(=O)N(CH3)2, -SO2NH2, -SO2NH(CH3), -SO2N(CH3)2-C(=S)N(CH3)2, -COOH, three(C1-C4alkyl)silyl, three-(C1-C4alkoxy)silyl, the hydroxy-group, With1-C6alkoxygroup, amino group, azide group, mercaptopropyl, C1-C6alkylamino,2-C12dialkylamino,3-C6alkenylamine,6-C12dialkylamino, C1-C6alkyls3-C6alkenylamine,1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6halogenation, C1-C6halogenacetylenes, C1-C6halogenallylacetic, SNO,2-C7alkylsulphonyl,2-C6alkoxycarbonyl,3-C6alkenylacyl,3-C6alkyloxyaryl, phenyl, aziridinyl group, azetidinone group, p is razorenova group, pyrazolidinone group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group or thiomorpholine group; or R3means aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, piperidino group, morpholino group, thiomorpholine group, mono - or polyamidine substituents, independently selected from the group comprising methyl, halogen and phenyl, and phenyl mono - or politeley substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup; or R3represents C1-C6-alkyl, C2-C6alkenyl,2-C6quinil,3-C7cycloalkyl, C1-C6alkoxygroup,2-C7alkylsulphonyl,2-C6alkoxycarbonyl,3-C6alkenylacyl,3-C6alkyloxyaryl or phenyl, or denotes phenyl, mono - or politeley will replace the guides and independently selected from the group comprising halogen, a cyano, a nitro-group, C1-C6alkyl, C1-C6halogenated, the hydroxy-group, C1-C6alkoxygroup, C1-C6halogenlampe and phenyl, where phenyl, in turn, may be mono - or polyamidine substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated and C1-C6alkoxygroup;

R5denotes phenyl, phenyl-C1-C12alkyl, phenyl-C3-C12cycloalkyl, phenyl-C3-C12alkenyl, or phenyl, phenyl-C1-C12alkyl, phenyl-C3-C12cycloalkyl, phenyl-C3-C12alkenyl, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, amino group, azide group, a hydroxy-group, mercaptopropyl, trialkylsilyl, tralkoxydim, Cho, COOH, C1-C6alkyl, C1-C6halogenated, C1-C6hydroxyalkyl,3-C8cycloalkyl,3-C8halogenosilanes,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil,2-C6halogenoalkanes, C1-C6alkoxygroup, C1-C6halogenlampe,3-C 6alkenylacyl,3-C6halogenaryloxy,3-C6alkyloxy,3-C6cycloalkanes,3-C6halogenocarboxylic, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6halogenation, C1-C6halogenacetylenes, C1-C6halogenallylacetic, -C(=O)NH2, -C(=S)NH2, -C(=O)NH(CH3), -C(=S)NH(CH3), -C(=O)N(CH3)2, -SO2NH2, -SO2NH(CH3), -SO2N(CH3)2and-C(=S)N(CH3)2.

Also particularly noteworthy is the compounds of formula I, in which

R5denotes hydrogen, (R51)(R52)(R53)Si-(C1-C12alkyl)-, Tris1-C6alkylsilane, phenyl-dis1-C6alkylsilane,1-C12alkyl, C3-C12alkenyl,3-C12quinil,3-C12cycloalkyl,3-C12cycloalkyl-C1-C12alkyl, C5-C12cycloalkenyl,1-C12alkoxy-C1-C12alkyl, C1-C12alkenylacyl-C1-C12alkyl, C1-C12alkyloxy-C1-C12alkyl, C1-C12alkylthio-C1-C12alkyl, C1-C12alkylsulfanyl-C1-C12alkyl, C1-C12al is ylsulphonyl-C 0-C12alkyl, C2-C12alkylsulphonyl-C0-C12alkyl, C3-C12alkenylboronic-C0-C12alkyl, C2-C12alkoxycarbonyl-C0-C12alkyl, C3-C12alkenylacyl-C0-C12alkyl or C3-C12alkyloxyaryl-C0-C12alkyl, or R5stands With1-C12alkyl, C3-C12alkenyl,3-C12quinil,3-C12cycloalkyl,3-C12cycloalkyl-C1-C12alkyl, C5-C12cycloalkenyl,1-C12alkoxy-C1-C12alkyl, C1-C12alkenylacyl-C1-C12alkyl, C1-C12alkyloxy-C1-C12alkyl, C1-C12alkylthio-C1-C12alkyl, C1-C12alkylsulfanyl-C1-C12alkyl, C1-C12alkylsulfonyl-C0-C12alkyl, C2-C12alkylsulphonyl-C0-C12alkyl, C3-C12alkenylboronic-C0-C12alkyl, C2-C12alkoxycarbonyl-C0-C12alkyl, C3-C12alkenylacyl-C0-C12alkyl, C3-C12alkyloxyaryl-C0-C12alkyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, is itagroup, an amino group, a hydroxy-group, mercaptopropyl, Cho, COOH, C1-C6trialkylsilyl, Tris1-C6alkoxysilyl, C1-C6alkyl, C1-C6halogenated,3-C8cycloalkyl,3-C8halogenosilanes, C1-C6alkenyl,1-C6halogenoalkanes, C1-C6alkoxygroup, C1-C6halogenlampe, C2-C7alkylsulphonyl,2-C7alkoxycarbonyl,2-C7alkenylacyl,2-C7alkyloxyaryl, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, -C(=O)NH2, -C(=S)NH2, -C(=O)NH(CH3), -C(=S)NH(CH3), -C(=O)N(CH3)2and-C(=S)N(CH3)2and R51, R52and R53are as defined above.

Another preferred subgroup of compounds represented by formula I, in which

R1and R2independently of one another denote C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;

or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;

R3denotes hydrogen, C1-C6halogenated, C1-C6alkyl, halogen, cyano, a nitro-group, With1-C4alkoxygroup, phenyl, phenyl containing as is amestitelj halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53are as defined above; preferably hydrogen, C1-C6alkyl, halogen, cyano, a nitro-group, With1-C4alkoxygroup, phenyl, phenyl containing as substituents halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53are as defined above;

R4denotes hydrogen, halogen, phenyl, imidazolyl, an amino group, a C1-C6alkoxygroup or C1-C6alkyl;

R5stands With1-C12alkyl or the group a, where a denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine

substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;

R6denotes hydrogen; and

R 7denotes hydrogen or C1-C6alkyl.

In other preferred compounds of formula I R6means-SH, -S-C1-C6alkyl or-S-C1-C6halogenated.

In a particularly preferred group of compounds of formula I

R1and R2independently of one another denote With3-C7cycloalkyl, C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;

or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;

preferably R1and R2independently of one another denote C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;

or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;

R3denotes hydrogen, C1-C6alkyl, C1-C6alkoxygroup, C1-C6halogenated, halogen, cyano, phenyl, phenyl containing as substituents halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53are as defined above;

preferably hydrogen, C1-C6alkyl, halogen, cyano, phenyl, phenyl containing as substituents halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53are such as defined above;

R4denotes hydrogen, halogen, C1-C6alkoxygroup or C1-C6alkyl;

preferably hydrogen or C1-C6alkyl;

R5represents C1-C6alkyl, phenyl or pyridyl, or C1-C6alkyl, phenyl or pyridyl mono - or disubstituted by halogen, C1-C6the alkyl, C1-C6halogenation, C1-C6alkoxygroup, C1-C6alkylthiol,

preferably C1-C6alkyl, phenyl or pyridyl, or phenyl or pyridyl mono - or disubstituted by halogen, C1-C6the alkyl, C1-C6halogenation,1-C6alkoxygroup, C1-C6alkylthiol,

R6denotes hydrogen; and

R7denotes hydrogen or C1-C6alkyl. Other preferred variants of implementation of the present invention are embodiments of E1-E, which are defined as the compounds of formula I, which are described by one formula selected from the group comprising formulas T1-T, described below, where the formulas T1-T values of the substituents R1, R2, R5and R6are the preferred values listed above.

For example, an implementation option E1 is characterized by compounds of the formula T1

in which

R1and R2independently of one another represent hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxygroup; or R1and R2together form2-C6Allenby bridge, which may be mono - or polyamidine metal groups; or R1and R2together with the connecting nitrogen atom of form pyrazolinone group, pyrazolidine group, pyrrolidone group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group, morpholino group, thiomorpholine group, each of which independently of one another may be mono - or polyamidine metal groups; or

R1denotes hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polyamidine substituents, n is dependent selected from the group including halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxy and R2denotes a hydroxy-group, an amino group, a C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation or3-C6alkyloxy; or R2denotes hydrogen, cyano, C1-C6alkyl, C3-C6cycloalkyl,2-C6alkenyl,2-C6quinil, benzyl or2-C7alkylsulphonyl, each of which may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6allylthiourea and C1-C6alkoxy and R1denotes a hydroxy-group, an amino group, a C1-C6alkoxygroup,3-C6alkenylacyl,3-C8cycloalkylation or3-C6alkyloxy;

R6denotes hydrogen, fluorine, chlorine, bromine, cyano, C1-C6alkyl, C1-C6halogenated or SNO; and

R5denotes phenyl, phenyl-C1-C12alkyl, phenyl-C3-C12cycloalkyl, phenyl-C3-C12alkenyl, or phenyl, phenyl-C1-C12alkyl, phenyl-C3-C12the CEC is alkyl, phenyl-C3-C12alkenyl, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, amino group, azide group, a hydroxy-group, mercaptopropyl, trialkylsilyl, tralkoxydim, Cho, COOH, C1-C6alkyl, C1-C6halogenated, C1-C6hydroxyalkyl,3-C8cycloalkyl,3-C8halogenosilanes,2-C6alkenyl,2-C6halogenoalkanes,2-C6quinil,2-C6halogenoalkanes, C1-C6alkoxygroup, C1-C6halogenlampe,3-C6alkenylacyl,3-C6halogenaryloxy,3-C6alkyloxy,3-C6cycloalkanes,3-C6halogenocarboxylic, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6halogenation,1-C6halogenacetylenes, C1-C6halogenallylacetic, -C(=O)NH2, -C(=S)NH2, -C(=O)NH(CH3), -C(=S)NH(CH3), -C(=O)N(CH3)2, -SO2NH2, -SO2NH(CH3), -SO2N(CH3)2and-C(=S)N(CH3)2.

Also particularly noteworthy is the connection option exercise E1, in which

R5the convoy is achet hydrogen, Tris1-C6alkylsilane, phenyl-dis1-C6alkylsilane,1-C12alkyl, C3-C12alkenyl,3-C12quinil,3-C12cycloalkyl,3-C12cycloalkyl-C1-C12alkyl, C5-C12cycloalkenyl, C1-C12alkoxy-C1-C12alkyl, C1-C12alkenylacyl-C1-C12alkyl, C1-C12alkyloxy-C1-C12alkyl, C1-C12alkylthio-C1-C12alkyl, C1-C12alkylsulfanyl-C1-C12alkyl, C1-C12alkylsulfonyl-C0-C12alkyl, C2-C12alkylsulphonyl-C0-C12alkyl, C3-C12alkenylboronic-C0-C12alkyl, C2-C12alkoxycarbonyl-C0-C12alkyl, C3-C12alkenylacyl-C0-C12alkyl or C3-C12alkyloxyaryl-C0-C12alkyl, or R5stands With1-C12alkyl, C3-C12alkenyl,3-C12quinil,3-C12cycloalkyl,3-C12cycloalkyl-C1-C12alkyl, C5-C12cycloalkenyl,1-C12alkoxy-C1-C12alkyl, C1-C12alkenylacyl-C1-C12alkyl, C1-C12alkyloxy-C1-C12alkyl, C1 -C12alkylthio-C1-C12alkyl, C1-C12alkylsulfanyl-C1-C12alkyl, C1-C12alkylsulfonyl-C0-C12alkyl, C2-C12alkylsulphonyl-C0-C12alkyl, C3-C12alkenylboronic-C0-C12alkyl, C2-C12alkoxycarbonyl-C0-C12alkyl, C3-C12alkenylacyl-C0-C12alkyl, C3-C12alkyloxyaryl-C0-C12alkyl, mono - or politeley substituents, independently selected from the group comprising halogen, a cyano, a nitro-group, an amino group, a hydroxy-group, mercaptopropyl, Cho, COOH, C1-C6trialkylsilyl, Tris1-C6alkoxysilyl, C1-C6alkyl, C1-C6halogenated,3-C8cycloalkyl,3-C8halogenosilanes, C1-C6alkenyl, C1-C6halogenoalkanes, C1-C6alkoxygroup, C1-C6halogenlampe,2-C7alkylsulphonyl,2-C7alkoxycarbonyl,2-C7alkenylacyl,2-C7alkyloxyaryl, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, -C(=O)NH2, -C(=S)NH2-C(=O)NH(CH3), -C(=S)NH(CH3), -C(=O)N(CH3)2and-C(S)N(CH 3)2.

In another preferred group of compounds of option exercise E1 R6means-SH, -S-C1-C6alkyl or-S-C1-C6halogenated.

In a particularly preferred group of compounds of option exercise E1 R1and R2independently of one another denote C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;

or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;

R5represents C1-C6alkyl, phenyl or pyridyl, or phenyl or pyridyl mono - or disubstituted by substituents selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6alkylthiols; and R6denotes hydrogen. The substituents R1, R2, R5and R6options for the implementation of E2-E are determined accordingly.

The compounds of formula I, and also used intermediates and reagents can be obtained by techniques known to the skilled chemist, in different ways, or they are available for sale.

The compounds of formula I can be obtained using a number of well-known techniques from amines of the formula II. These techniques include the following:

(a) the following scheme 1: Amide of the formula (R6)C(=O)-N(Rsub> 1)(R2or formamid formula HC(=O)-N(R1)(R2handle these reagents as POCl3, PCl3, SOCl2, COCl2Ph-SO2Cl, Me2N-SO2Cl (CF3CO)2O, and then with the amine of formula II.

(b) the following scheme 1: the interaction of the amino derivatives of formula II in which R3, R4, R5and R7are as defined above for formula I, with a compound of formula R6-C(OR)2-N(R1)(R2), where R1, R2and R6are as defined above for formula I, or with the compound of the formula R6-C(OR)(NR1R2)2where R preferably denotes alkyl or phenyl group, and R1, R2and R6are as defined above for formula I, or, for the first reagent, the two R together form alkylidene fragment. Such transformations are described in the literature, for example, in Bashkirskii Khimicheskii Zhurnal (2000), 7(2), 5-9; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1981), 20B(12), 1075-7; ARKIVOC (Gainesville, FL, United States) (2004), (10), 20-38.

Scheme 1

c) the following scheme 2: Amino derivatives of formula II can be converted into amide and, in turn, in the final compound of formula I using a two-stage sequence: 1) activation (using, for example, PCl5or Ph3PO together with (CF3SO2) 2O, and then 2) by reaction with an amine of the formula HN(R1)(R2), in which R1and R2are as defined above for formula I.

Such techniques are described in the literature, for example, in the Journal of Organic Chemistry (1989), 54(5), 1144-9; Zhurnal Organicheskoi Khimii (1989), 25(2), 357-67.

Scheme 2

d) following scheme 3: Amino derivatives of formula II can first be converted into the corresponding isocyanate. It, in turn, is then injected into the reaction with formamide of the General formula HC(=O)-N(R1)(R2), in which R1and R2are as defined above for formula I, and get formamidine formula I. Such techniques can be found in the literature, for example, in the Journal of Pharmaceutical Sciences (1964), 53(12), 1539-40; Journal für Praktische Chemie (Leipzig) (1961), 13, 265-71.

Scheme 3

(e) the following scheme 4: compounds of General formula (Ie2) and (Ie1) are subgroups of compounds opissyvayusya General formula (I). Compounds of General formula (Ie2can be obtained by reaction of compounds of General formula (Ie1) with an amine of the formula HN(R1e)(R2e) under suitable conditions. Fragments of the formula-N(R1e1)(R2e1) are a subgroup of the fragments of the formula-N(R1)(R2), and the compounds of formula HN(R1e2)(R2e2) form a subgroup of compounds of formula HNR1R2. Such techniques can the be found in literature, for example, in Tetrahedron Letters (1989), 30(1), 47-50; Khimicheskii Zhurnal (2000), 7(2), 5-9.

Scheme 4

f) the following scheme 5: compounds of General formula Ifwhich is a subgroup of the compounds of formula I, can be obtained by acylation or alkylation of compounds of formula If1. Such techniques can be found in the literature, for example, in Chemical & Pharmaceutical Bulletin (1983), 31(10), 3534-43; Zhurnal Organicheskoi Khimii (1989), 25(2), 357-67; Tetrahedron (2000), 56(39), 7811-7816; Journal of the Chemical Society, Transactions (1923), 123, 3359-75.

Scheme 5

The substituents R and Rfin the formulas is a subset of substituents R1(or R2).

The compounds of formula II can be obtained from the corresponding nitro-derivatives of the formula III according to different methods of recovery.

(g) the following scheme 6: recovery Techniques include the transformation of the nitro compounds of formula III in which R3, R4, R5and R7are as defined above for formula I, in the presence of a catalyst, for example, catalysts based on Pd, Ni or Pt, and molecular hydrogen, in a suitable solvent at ambient temperature or at elevated temperatures, under normal or higher pressure, or recovery can be performed using one of several methods of restoring metal, for example, with the use of such measures is allow, as Fe, Sn, Zn, or such reagents as SnCl2in acidic and/or proton environment.

Scheme 6

Nitro compounds of formula III can be obtained in various ways. They include the following:

h) the following diagram 7: the compounds of formula III can be obtained from compounds of formula IV in which R3, R4and R7are as defined above for formula I, containing useplease group R100where R100denotes SH-, nitro-group, a halogen, imidazolyl, triazolyl,1-C6allylthiourea, C1-C6alkylsulfonyl or C1-C6alkylsulfonyl, preferably halogen, C1-C6allylthiourea, C1-C6alkylsulfanyl,1-C6alkylsulfonyl, more preferably F, Cl, Br, I, MeS-, MeSO - or MeSO2-; or R100indicates imidazolyl, triazolyl, PhSO2, CF3SO2-O-, p-MeC6H4SO2O-, O2N-) by reaction with R5-OH, where R5is the same as defined above for formula I, in the presence of a base. This transformation can be done using the previously obtained salt R5OH.

Scheme 7:

i) the following scheme 8, Compounds of formula IIIican be obtained by the reaction of the precursor of formula IViwith the electrophilic previous the nick R 5i-X, where R5idenotes a suitable subset of R5and X denotes useplease group, such as halogen or MeSO2O or p-MeC6H4SO2O, the reaction is preferably carried out in the presence of a base. Or, alternatively, compound IViyou can enter into reaction with the alcohol of formula R5i-OH when the reaction conditions, Mitsunobu, using for example, Ph3P, EtO-C-N=N-CO-OEt in solvents such as dioxane, THF or toluene. Such techniques are described in the literature, for example, Journal of Medicinal Chemistry (2006), 49(15), 4455-4458; Tetrahedron Letters (2006), 47(28), 4897-4901.

Scheme 8

(j) the following diagram 9: nitro compounds of formula IIIjwhich is a subgroup of the compounds of formula III can also be obtained by using an appropriate precursor Vjwith a group Y, for example, halogen or a group of CF3SO2O, which can be used for the introduction of R3j, R3jwhich is a subgroup of R3. For such transformations is developed and described in the literature a large number of reliable methods (for example, reaction of a combination of Suzuki, Suzuki-Miyaura, Negishi, Steele, or the Heck reaction and Sonogashira).

Scheme 9

k) the following diagram 10: the compounds of formula IIIkwhich is a subgroup of the compounds opissyvayusya Faure who uloi III, can be obtained, as shown in figure 10, using well known techniques. These include, for example, reaction of a combination of Suzuki-Miyaura and still using electrophilic reagents (R3k1)-X, X denotes useplease group, preferably Cl, Br or I. In light of the definition given in scheme 10, R3k1is part of many molecular frameworks that are commonly used for carrying out reactions that are possible in this case. (R3k1)-X includes halides aryl-, heteroaryl or vinylsamurais systems. The technique described in the present invention, also includes reactions with the precursor (R5k2)-H, with the formation of the nucleophilic systems, which under certain conditions can be joined with the main pyridine fragment (Vk). The last classes include, for example, the amination reaction or reacting with the precursor carbonyl compounds (containing an acidic group SN in α-position to the carbonyl). In both cases, there are many catalytic systems described in the literature for carrying out the transformation.

Scheme 10

1) the following diagram 11: the compounds of formula IIILwhich is a subgroup of the compounds of formula III can be obtained by the reaction of electrophilic compounds of the formula (R3La)-X (X denotes useplease group, so the Yu as halogen or MeSO 2O) with the anion formed from compounds of formula VLwith the base under suitable conditions, which are described in the literature.

Scheme 11

m) the following diagram 12: the compounds of formula IIImwhich is a subgroup of the compounds of formula III can also be obtained by transformation of a functional group R3m1predecessor to the group R3m. Fragments of formula R3m, which is a subset of fragments defined by the formula R3and the predecessor of the fragment of the formula R3maare such that the definitions of formula R3mpreserved after the transformation. For example: (R3m1- can be a VAT-which can be transformed into F2CH - using such reagents as (diethylamino)certified or SF4or (R3m1)-) can be represented as H3With-H2C-S-which can be split in N3C-H2With-S(=O)- and N3C-H2With-S(=O)2by oxidation by standard techniques, which are described in detail in the literature; or (R3m1-) can be a-C=S)NH2that can be converted into optionally substituted thiazolidines fragment by standard methods described in the literature.

Scheme 12

n) the Techniques described above in sections (j)-m), for the introduction of prevrasheniya Deputy R 3also you can use in case the substituents R4And R7.

(o) the following diagram 13: the Methods listed above in sections (j)-m), in the appropriate form can also be used for treatment of compounds of formula IIIorepresenting the connection of the subgroups of compounds of formula III. In this case, suitable substituent R5o1turn in the substituent R5othe substituents R5oare a subgroup of the substituents R5.

Scheme 13

p) the following diagram 14: the Methods described above in sections (g)) are also applicable in cases when the nitro-group is replaced by hydrogen or amino group, or a suitably protected amino group (such as, for example, -NH-C(=O)-CH3, -NH-C(=O)-tert-butyl, -NH-benzoyl, -N(C(=O)-CH3)2-phthaloyl, -N(benzyl)2, -NH-C(=O)-O-tert-butyl), or any amedieval group-N=C(R6)-N(R1)(R2). However, the specialist in the art knows that this is not the General approach is applicable in cases where the existence of compatible functional groups. For example, this approach is presented in figure 14 for the transformations described in section m) above if, when, instead of the nitro group contains medinova group (formula X). Cm. define R3m1and R3min section m) above and the definition of R100in section a is e (h) above. The compounds of formula X, in which R1, R2, R3, R4, R6and R7are as defined for formula I in section I, and R100denotes SH-, nitro-group, a halogen, imidazolyl, triazolyl, C1-C6allylthiourea, C1-C6alkylsulfonyl or C1-C6alkylsulfonyl are new and therefore constitute another object of the present invention.

Scheme 14

q) the following diagram 15: the compounds of formula III can be obtained by direct nitration of the appropriate precursor, provided that the used method of nitration applicable to the original substances. This nitration can be performed in various well known ways. For example, using a mixture of acid HNO3and H2SO4. By this method, the precursor may be first dissolved in H2SO4and to enter into reaction with the mixture of acids, or it can be processed directly by a mixture of acids under various conditions. In addition, nitration can be performed at the system inert solvents such nitrous reagents, as BF4NO4. The nitration can be carried out using HNO3in a suitable solvent, such as H2O, Asón, acetic anhydride. These same techniques can also be used to podhodyashego the precursor of formula VII to obtain a compound of formula IV. X denotes useplease group that is defined above in section h).

Scheme 15

r) the following diagram 16: the compounds of formula VII can be synthesized using a variety of well known techniques. Preferably, by transformation of the precursors of formula VIII or IX. X denotes useplease group that is defined above in section h).

r1) If the compound of formula VIII is a precursor, the method includes the transformation of the compound in which X denotes Cl, using such reagents as PCl5, POCl3, SOCl2or ClCO-COCl, usually by heating in an inert solvent, in the absence or in the presence of a suitable base. If X denotes Br, the preferred reagents include POBr3, PBr3and NBS together with Ph3P. If X denotes CF3SO2O, the preferred methods of synthesis using such reagents as (CF3SO2)2O in the presence of a base, for example, Et3N or 2,6-lutidine.

r2) If the compound of formula (IX) is a precursor, it is preferred methods include the following. If X denotes Cl or Br, then you can use a technique type Sandmeyer, i.e. the diazotization and subsequent reaction with chloride or copper bromide(I). Or, if X denotes F, after diazotization get diazo is iverboat, which then in turn ftoroproizvodnykh. Perborate can also be obtained using organic nitrite and epirate BF3.

Scheme 16

s) the following diagram 17: the Large number of compounds of formulas VIII and IX, or connections that are possible precursors, available for sale. In addition, there are many ways of synthesis of pyridine structural elements of the General formulas VIII and IX, in large quantities described in the literature. For example, note the following 3 synthesis of compounds corresponding to the General definition of the compounds of formula IX, which are presented below in schemes 18-20.

Scheme 17

Scheme 18

Journal of Organic Chemistry (2005), 70(4), 1364-1368

Scheme 19

Journal of Heterocyclic Chemistry (1977), 14(2), 203-5

Scheme 20

Synthesis (2005), (8), 1269-1278

Reactions leading to compounds of formula I, preferably carried out in aprotic inert organic solvents. Such solvents are hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride or chlorobenzene, ethers, such as diethyl ether, dimethyl ether of ethylene glycol, dimethyl ether is of etilenglikola, tetrahydrofuran or dioxane, NITRILES, such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone. The temperature of the reaction is preferably from -20 to +120°C. Usually the reaction is slightly exothermic and usually they can be carried out at room temperature. To shorten the duration of the reaction or to initiate the reaction mixture is briefly heated to the boiling temperature of the reaction mixture. The duration of the reaction can also be reduced by adding a few drops of a base as catalyst of the reaction. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, Hinkley, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. However, as the bases can be used inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, such as sodium carbonate and potassium carbonate, or hydrogen carbonates, such as potassium bicarbonate and sodium bicarbonate. Grounds can be used by themselves or with the addition of catalytic amounts of phase transfer catalyst, for example, crown ether, in particular 18-crown-6, or a salt tetr is alkylamine.

The compounds of formula I can be distinguished in the usual manner by concentration and/or by evaporation of the solvent and purify by recrystallization, trituration of the solid residue with solvents in which they are poorly soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

The compounds of formula I and, if appropriate, their tautomers can be in the form of one of the isomers, which is possible, or mixtures thereof, for example, in the form of pure isomers, such as antipodes and/or diastereoisomers, or as mixtures of isomers, such as mixtures of structural isomers, stereoisomers, diastereoisomers and enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates depending on quantities, absolute or relative configuration of asymmetric carbon atoms contained in the molecule, and/or depending on the configuration of non-aromatic double bonds, which are contained in the molecule; the present invention relates to the pure isomers and to all mixtures of isomers that are possible, and in each case above and below in the present invention, it should be understood in this sense, even if not specified the details of the stereochemistry.

A mixture of diastereoisomers or mixtures of racemates of the compounds I, to the that you can get depending on, what source materials and methods selected by known methods can be divided into pure diastereoisomers or racemates on the basis of differences in physico-chemical characteristics of the components, for example, by fractional crystallization, distillation and/or chromatography.

Mixtures of enantiomers, such as racemates, which can be obtained in a similar way, can be divided into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral sorbents, for example, by high performance liquid chromatography (HPLC) on a cellulose acetate, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of compounds including, for example using chiral crown ethers, which forms a complex with only one enantiomer, or by conversion into salts diastereoisomers, for example, by reaction of the racemate primary outcome product with an optically active acid, such as carboxylic acid, for example, camphor, tartaric or malic acid, or sulfonic acid, for example, camphorsulfonic acid, and separating a mixture of diastereoisomers that you can obtain thus, for example, by means of fractional crystallization, basedon the difference in their solubilities, obtaining diastereoisomers from which you can select the desired enantiomer by treatment with suitable reagents, for example, the main reagents.

Net diastereoisomers or enantiomers in the context of the present invention can be obtained not only by the separation of suitable mixtures of isomers, but also by well-known methods of diastereoselective or enantioselective synthesis, for example, by implementing the method. proposed in the present invention, the starting materials with the appropriate stereochemical configuration.

In each case, it is preferable to select or synthesize more effective biological isomer, for example enantiomer or diastereoisomer, or a mixture of isomers, for example, a mixture of enantiomers, or a mixture of diastereoisomers, if the individual components have different biological activity.

The compounds I and, if appropriate, their tautomers, it is also possible, if appropriate, to receive in the form of the hydrates and/or form, to include other solvents, for example, those that could be used for the crystallization of compounds that are in solid form.

According to the invention it was found that the compounds of formula I proposed in the present invention, from a practical point of view have a very attractive range of the instrument is vnesti for protecting useful plants against diseases caused by phytopathogenic microorganisms, such as fungi, bacteria and viruses.

The present invention relates to a method of combating infestation of useful plants by phytopathogenic microorganisms or warnings, in which the compound of formula I is applied as the active ingredient to the plants, to parts thereof or the place of their growth. The compounds of formula I proposed in the present invention, an excellent performance at low consumption rates, are well tolerated by plants and are environmentally safe. They have a very useful curative, preventive and systemic characteristics and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests found on plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) in different crops of useful plants and at the same time to protect those parts of plants which grow later, for example, from phytopathogenic microorganisms. The compounds of formula I can also be used as an etching agent for the material for the propagation of plants, such as seeds (fruit, tubers, grains) and plants (e.g. rice), to protect against fungal infections, as well as phytopathogen the different mushrooms, found in the soil.

In addition, the compounds proposed in the present invention, can be used to control fungi in related industries, for example, for the protection of technical materials, including timber and manufactured timber-technical products, during storage of food products with hygienic measures.

The compounds of formula I, for example, effective against the phytopathogenic fungi of the following classes: Fungi deuteromycota (for example, Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and basidiomycetes (for example, Rhizoctonia, Hemileia, Puccinia). In addition, they are also effective against classes of records of Ascomycetes (for example Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and the class of the oomycetes (for example, Phytophthora, Pythium, Plasmopara). Found to have extremely high activity against powdery mildew (Erysiphe spp.). In addition, the new compounds of formula I are effective against phytopathogenic bacteria and viruses (for example, against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora, and also against tobacco mosaic virus). Found a good activity against Asian soybean rust (Phakopsora pachyrhizi).

In the scope of the present invention is useful plants to be protected, typically include the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); apples, cost the same and berries (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and black currants); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor, cocoa beans, groundnut); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, paprika); Laurel (avocado, cinnamon, camphor), and plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamental plants.

The term "useful plants" is to be understood as including also useful plants engineered resistance to herbicides, such as bromoxynil, or or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example, primisulfuron, prosulfuron and trifloxysulfuron, EPSPS protein inhibitors (5-enolpyruvylshikimate-3-paspatinath), inhibitors of GS (glutamylcysteine) using conventional methods of breeding or genetic engineering. An example of a culture, which with the aid of conventional methods of breeding (mutagenesis) given resistance, for example, to imidazolinones, for example, imazamox is rape Clearfield® canola). Examples of crops, which by means of techniques of genetic engineering has resistance to herbicides or classes of herbicides, are maize, resistant, for example, to glifosato or glufosinate, which are commercially available under the trade names RoundupReady® and LibertyLink®.

The term "useful plants" is to be understood as including also useful plants that are by the use of techniques based on recombinant DNA modified so that they are capable to synthesize one or more providing selective exposure to toxins, such as, for which it is known, for example, that they are produced producing toxins by bacteria, especially of the genus Bacillus.

Transgenic plants containing one or more genes that encode resistance to insects and Express one or more toxins are known and some are commercially available. Examples of such plants are: YieldGard® (maize, which expresses the toxin CryIA(b)); YieldGard Rootworm® (maize, which expresses the toxin CryIIIB(b1)); YieldGard Plus® (a corn variety that expresses a CryIA toxins(b) and CryIIIB(b1)); Starlink® (maize, which expresses the toxin Cry9(c)); Herculex I® (maize, which expresses the toxin CryIF(a2) and the enzyme phosphinotricin-N-acetyltransferase (PAT) for imparting resistance to the herbicide glufosinate-ammonium); NuCOTN 33B® (grade cotton, which expresses the toxin CryIA(c)); Bollgard I® (grade cotton, which expresser is no toxin CryIA(c)); Bollgard II® (grade cotton that expresses a CryIA toxins(c) and a CryIIA(b)); VIPCOT® (grade cotton that expresses a VIP toxin); NewLeaf® (potato variety that expresses a toxin CryIIIA); NatureGard®, Agrisure® GT Advantage (GA21 resistant to glyphosate), Agrisure® CB Advantage (Bt11 resistant to corn borer (CB)) and Protecta®.

The term "useful plants" is to be understood as including also useful plants that are by the use of techniques based on recombinant DNA modified so that they are able to synthesize providing selective exposure protivopolojnye substances, such as, for example, so-called "associated with the pathogenesis of proteins" (PRPS, see, for example, EP-A-0392225). Examples of such protivopolojnih substances and transgenic plants capable of synthesizing such protivopolojnye substances, see, for example, in EP-A-0392225, WO 95/33818, EP-A-0353191. Methods of producing such transgenic plants are usually well-known specialist in the art and described, for example, in the above publications.

The term "locus" useful plants for use in the present invention means a place where grow useful plants, which were planted materials for the propagation of useful plants or on which will be placed in the soil materials for the propagation of useful plants. An example of such a place protract the Oia is a field, on which to grow crops.

The term "material for breeding plants" should be understood as meaning all the generative parts of the plant, such as seeds, which can be used for reproduction of the latter, and vegetative material such as cuttings and tubers, such as potatoes. For example, it can be noted seeds (in the strict sense of the word), roots, fruits, tubers, bulbs, rhizomes, plant parts. You can also sprouted plants or seedlings that need to be transplanted after germination or seedling emergence from the soil. The seedlings can be protected before transplanting by complete or partial processing carried out by dipping. It should be understood that the preferred material for propagation" means the seeds.

The compounds of formula I are used in unmodified form or, preferably, together with carriers and excipients commonly used for the preparation of drugs.

Therefore, the present invention also relates to compositions for combating phytopathogenic microorganisms and protection, including the compound of the formula I and an inert carrier, and to a method of combating infestation of useful plants by phytopathogenic microorganisms and their prevention, in which a composition including a compound of formula I as the active ingr diente and an inert carrier, applied to plants, to parts thereof or to the place of their growth.

For this purpose the compounds of formula I and an inert carriers usually are prepared in a known manner in the form of mulgirigala concentrates, pastes for application, directly spray or dilutable solutions, diluted emulsions, wettable powders, soluble powders, Farrukh Dustov, granulates, and also forms, encapsulated, for example in polymeric substances. As the type of composition, methods of application, such as spraying, atomization, dusting, scattering, coating or watering, are selected in accordance with intended use and prevailing circumstances. The composition may also contain other excipients, such as stabilizers, antifoaming agents, viscosity regulators, binders or substance, which imparts stickiness, as well as fertilizers, micronutrients sources or other arrangements designed to provide special effects.

Suitable carriers and excipients can be solid or liquid and are substances used in the preparation technology of drugs, for example, natural or regenerated mineral substances, solvents, dispersing agents, wetting agents, substances imparting stickiness, thickeners, binders or adobr the deposits. Such systems are for example described in WO 97/33890.

The compounds of formula I or compositions containing the compound of formula I as active ingredient and an inert carrier, can be applied on the place of cultivation or on the treated plant simultaneously or sequentially with additional compounds. These additional compounds can be, for example, fertilizers or micronutrients or other preparations that influence plant growth. They can also be selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if necessary, together with further carriers, surfactants, or excipients that improve the application, commonly used in the field of preparation.

The preferred method of making compounds of formula I or a composition comprising the compound of formula I as active ingredient and an inert carrier, is foliar application. The frequency of payment and the rate of application depend on the exposure of the corresponding pathogen. However, the compounds of formula I can also penetrate the plant through the roots from the soil (systemic exposure) under sprinkler irrigation habitats of plants with liquid drug or when making connections to Itochu in solid form, for example, in granular form (soil application). Under flooded crops such as rice, such granules can be made in flooded rice field. The compounds of formula I also can be applied to seeds (coating) by soaking seeds or tubers liquid drug fungicide or coated solid preparation.

The drug, i.e. a composition comprising a compound of formula I and optionally a solid or liquid excipient, are prepared by known methods, typically by careful mixing and/or grinding the compound with extenders, e.g. solvents, solid carriers and optionally a surface-active substances.

The agrochemical preparations usually contain from 0.1 to 99 wt.%, preferably from 0.1 to 95 wt.% the compounds of formula I, from about 99.9 to 1 wt.%, preferably from 99,8 to 5 wt.% solid or liquid excipients and from 0 to 25 wt.%, preferably from 0.1 to 25 wt.% surface-active substances.

Whereas commercial products are preferably prepared in the form of concentrates, the end user typically will use diluted preparations.

Preferred application rates typically range from 5 g to 2 kg of active ingredient (AI) per hectare (ha), preferably from 10 g to 1 kg AI/ha, most preferably from 20 g to 600 g And/ha. When used as a means for seed soaking the usual dose is from 10 mg to 1 g of active substance per 1 kg of seeds. The rate of application for ensuring impact can be determined experimentally. It depends on the type of exposure, the stage of development of the crop and the application (site, time mode, methods of making and depending on these parameters vary widely.

These methods are especially effective for combating phytopathogenic organisms of the Kingdom fungi, type the basidiomycetes class Uredinomycetes, subclass Urediniomycetidae and detachment of the Uredinales (commonly known as rust). Types of rust, particularly affecting crops include species of the family Phakopsoraceae, especially species of the genus Phakopsora, for example, Phakopsora pachyrhizi, which is also known as Asian soybean rust, and species of the family Pucciniaceae, especially species of the genus genus Puccinia, such as Puccinia graminis, also known as stem rust, or black rust, which is a dangerous disease of cereals, and Puccinia recondita, also known as leaf rust.

The embodiment of the above method is a method of protecting crops of useful plants from the invasion of pathogenic microorganisms and/or treatment of crops of useful plants, infected by the phytopathogenic the microorganisms, this method involves the simultaneous application of glyphosate, including its salts or esters, and at least one of the compounds of formula I, which has activity against phytopathogenic microorganisms, at least one object selected from the group comprising plant, plant part and place of origin.

According to the invention it has been unexpectedly found that the compounds of formula I or a pharmaceutical salt, described above, also have a spectrum of activity that is suitable for removing and/or preventing a microbial infection in an animal.

"Animal" means any animal, for example, insect, mammal, reptile, fish, amphibian, preferably a mammal, most preferably a human. "Treatment" means the application to the animal, which has a microbial infection, to reduce, or diminish or stop the increase or spread of infection, to reduce infection, or to eliminate the infection. "Warning" means applying to the animal, in which there are no visible signs of microbial infection, to prevent any future infection, or to reduce or mitigate the gain or distribution of any future infections.

Therefore, the present invention relates to the use of compounds of formula I DL the preparation of a medicinal product, designed to eliminate and/or prevent microbial infection in an animal. The present invention also relates to the use of compounds of formula I as a drug. The present invention also relates to the use of compounds of formula I as an antimicrobial agent for the treatment of the animal. The present invention also relates to pharmaceutical compositions comprising as active ingredient a compound of formula I or its pharmaceutically acceptable salt and a pharmaceutically acceptable carrier or diluent. This composition can be used to eliminate and/or prevent microbial infection in an animal. This pharmaceutical composition may be in a form suitable for oral administration such as tablet, pellet, hard capsules, aqueous suspensions, oily suspensions, emulsions, dispergirujutsja powders, dispergirujutsja granules, syrups and elixirs. Alternatively, this pharmaceutical composition may be in a form suitable for topical application, such as a spray, cream or lotion. Alternatively, this pharmaceutical composition may be in a form suitable for parenteral administration, for example, injection. Alternatively, this pharmaceutical composition can be in an inhaled form, such as the RAS is ilyaimy the aerosol.

The compounds of formula I can be effective against the organisms of different species, which can lead to microbial infection in an animal. Examples of these types of microorganisms are those that cause aspergillosis, such as Aspergillus fumigatus, A.flavus, A.terrus, A.nidulans and A.niger; which causes blastomycosis, such as Blastomyces dermatitidis; which cause a Candida, such as Candida albicans, .glabrata, .tropicalis, .parapsilosis, .krusei and .lusitaniae; which causes coccidioidomycosis, such as Coccidioides immitis, which causes cryptococcosis, such as Cryptococcus neoformans; which cause histoplasmosis, such as Histoplasma capsulatum and which cause zivotopis, such as Absidia corymbifera, Rhizomucor pusillus and Rhizopus arrhizus. Other examples are Fusarium Spp, such as Fusarium oxysporum and Fusarium solani and Scedosporium Spp, such as Scedosporium apiospermum and Scedosporium prolificans. Additional examples are Microsporum Spp, Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.

Following non-limiting examples illustrate in more detail the present invention described above, without imposing on him the constraint.

Examples of making connections:

Example P1: Obtaining N'-[6-(4-chloro-3-triptoreline)-5-(4-forfinal)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 3,5-dibromo-6-methylpyridin-2-ol:

In pathology p is a promotional flask with a volume of 1.5 l, equipped with a mechanical stirrer and protected from sunlight with aluminum foil, 30.0 g of 6-methylpyridin-2-ol are suspended in 300 ml of dry acetonitrile and stirred at ambient temperature. When cooled in a cooling bath of ice water for 25 min servings slowly add 97.9 g of N-bromosuccinimide (NBS). There is a slight evolution of heat (the temperature rises to 29°C). Because the suspension is difficult to mix, re-add 300 ml of dry acetonitrile and stirring is continued at ambient temperature for about 1.75 hours Then the suspension is filtered, the filter cake is washed thoroughly with methanol to remove succinimide and dried, yielding the 64.1 g of compound as a white solid (TPL (melting point) >225°C).

b) Obtaining 3-bromo-6-methylpyridin-2-ol:

In pathology reaction flask with a volume of 1.5 l (flame dried) to 63.1 g of 3,5-dibromo-6-methylpyridin-2-ol are suspended in 300 ml of dry THF and stirred under argon atmosphere at ambient temperature. The reaction mixture is cooled to a temperature equal to from -78 to -80°C (cooling bath with a mixture of Et2O/solid carbon dioxide). For 2.5 h add 295 ml of 1.6 M solution of n-utility in hexane, resulting in the observed temperature increase up to -74°C (who, Alto-orange suspension). Stirring is continued at a temperature of from -78 to -80°C for 1 h and Then for 15 min slowly add 42,6 ml of water. After stirring at -78°C for 20 min the reaction mixture during the night allowed to warm to ambient temperature. The next day, the mixture was concentrated in vacuo and get wet yellow solid. After adding 200 ml of an aqueous solution of NaCl, the mixture is extracted with AcOEt when the pH value is equal to 9, and after drying the organic phase over sodium sulfate, filtration and concentration in vacuo get to 37.2 g of a resinous substance. The concentration of the aqueous phase in vacuo gives to 70.1 g of solid substance. United party, thus obtained, purified using flash chromatography [silica gel (column: h = 25 cm ⌀=12 cm) and tert-butyl methyl ether with 1% vol. Asón]. Fraction mainly containing the desired compound are pooled (only 29.7 g) and suspended in Et2O at ambient temperature, the mixture is stirred, then filtered, the filter cake is washed with Et20 and after drying gain of 14.7 g of compound as a white solid (TPL=212-213°C).

1H NMR (400 MHz, CDCl3): δ of 2.35 (s, 3H), 5,97 (d, 1H), 7,71 (d, 1H), 12,35 (broad, 1H).

c): Obtain 3-bromo-6-methyl-5-nitropyridine-2-ol:

In odnogolosy round the bottom flask 500 ml add 230 ml of 65% aqueous solution of HNO 3and stirred under cooling (cooling bath with a mixture of ice/water). When the ambient temperature is added in several portions of 7.00 g of 3-bromo-6-methylpyridin-2-ol. Stirring is continued at ambient temperature for 3.5 hours the Mixture was poured into 200 ml of a mixture of ice/water (pH 1), then the aqueous phase is extracted with AcOEt. The organic phase is washed twice with water with pH is brought to 4 by adding aqueous NaOH solution (pH measured pH meter), then dried over sodium sulfate, filtered and concentrated in vacuo and get 7,52 g yellow solid. The crude substance is suspended in diethyl ether and stirred at ambient temperature for 1 h, filtered, washed with the same solvent and dried, yielding to 3.89 g of compound as a yellow-orange solid (TPL >220°C).

1H NMR (400 MHz, CDCl3): δ of 2.86 (s, 3H), 8,66 (s, 1H), was 12.75 (broad, 1H).

d) Obtaining 3-bromo-2-chloro-6-methyl-5-nitropyridine:

In odnogolosy round bottom flask of 100 ml equipped with a fridge, 4,36 g of pyridone added to 17 ml of phosphorus oxychloride (brown suspension). Then this mixture is stirred at the boil under reflux for 7 hours, After cooling the mixture to ambient temperature it was concentrated in vacuo at 50°C, then 3 times to ablaut toluene and concentrated in vacuo and get brown oily resinous substance. This resinous substance is treated with ice, then an excess of a saturated aqueous solution of sodium bicarbonate. The mixture is extracted with AcOEt. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo and get 3,79 g brown solid. Purification of solids by using flash chromatography using a cartridge of silica gel (50 g, 150 ml) and a mixture of heptane/ethyl acetate 95:5 (vol.:about.) network of 3.32 g of compound as a pale yellow solid (TPL = 76-78°C).

1H NMR (400 MHz, CDCl3): δ 2,82 (s, 3H), 8,55 (s, 1H).

e) Obtaining 3-bromo-2-(4-chloro-3-triptoreline)-6-methyl-5-nitropyridine:

In odnogolosy round bottom flask of 50 ml volume of 1.21 g of 4-chloro-3-triptoreline dissolve 0.13 ml hexamethyldisilazane and stirred in an argon atmosphere at ambient temperature in 3.0 ml of dry dioxane. This mixture is carefully added 270 mg of a 55% suspension of sodium hydride (gas evolution) and the stirring continued for 30 minutes Then with a syringe and added dropwise a solution of 1.55 g of 3-bromo-2-chloro-6-methyl-5-nitropyridine 4.0 ml of dry dioxane and stirring is continued at ambient temperature for 22 hours the Reaction is stopped by adding an excess of dilute aqueous NaOH solution (pH of the aqueous phase = 12), and the mixture is extracted with cyclohex the nom. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo and get an orange oil. Purification using flash chromatography using a cartridge of silica gel (50 g, 150 ml) and a mixture of heptane/ethyl acetate 95:5 (vol.:about.) as eluent give 480 mg of the compound in the form of wet solids.

1H NMR (400 MHz, CDCl3): δ to 2.65 (s, 3H), 7,07 (dd, 1H), 7,55 (d, 1H), 7,58 (d, 1H), 8,65 (s, 1H).

f) Obtaining 2-(4-chloro-3-triptoreline)-3-(4-forfinal)-6-methyl-5-nitropyridine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a fridge, 260 mg of 3-bromo-2-(4-chloro-3-triptoreline)-6-methyl-5-nitropyridine and 97 mg p-ftorhinolonovy acid are dissolved in 1.7 ml of dioxane and stirred in an argon atmosphere at ambient temperature (yellow solution). Then add 228 mg K3PO4dissolved in 0,85 ml H2O. the mixture is Then Tegaserod by stirring in an argon atmosphere for 15 minutes Then add 4.3 mg tricyclohexylphosphine and 3.6 mg of bis(benzylideneacetone)palladium. Then the solution is vigorously stirred at 100°C for 6.5 hours Then dark brown suspension is cooled to ambient temperature, then add 10 ml of a saturated aqueous solution of NH4Cl. This mixture is extracted with AcOEt. The organic phase is dried over Na2SO4 , filtered and concentrated in vacuo and obtain 340 mg of a dark brown oil. After purification of the residue via flash chromatography [cartridge with silica gel (20 g, 60 ml) and a mixture of heptane/ethyl acetate 95:5 (vol.:vol.), then 9:1 (vol./about.)] receive 120 mg of the compound as a yellow oil.

TLC (thin layer chromatography): Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 2:1 (by vol.:vol.); Rfconnection = 0,50.

g) Receiving 6-(4-chloro-3-triptoreline)-5-(4-forfinal)-2-methylpyridin-3-ylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a fridge, 120 mg of the original substance is stirred at 0.50 ml of methanol (light yellow suspension). While cooling with ice with a syringe and added dropwise to 0.50 ml of an aqueous solution of concentrated HCl (loss of additional quantities of sediment). Bath with ice and remove slowly added 270 mg of anhydrous SnCl2(light yellow suspension). Stirring is continued while boiling under reflux for 6.5 h (light yellow solution). Then the mixture was concentrated in vacuo and get wet beige solid. After addition of AcOEt add 5 ml of 4 M aqueous NaOH solution. After extraction the organic phase is dried over Na2SO4the filter is ut (sintered glass) and the solvent is removed in vacuum and obtain 110 mg of the crude compound (light yellow-brown oil). Purification of the residue is performed using flash chromatography (cartridge with silica gel (20 g, 60 ml) and a mixture of heptane/ethyl acetate 2:1 (by vol.:about.)) and receive 60 mg of the compound as a yellow oil. RP HPLC (high performance liquid chromatography with reversed phase): retention Time of compound: 2,10 min

h) Obtaining N'-[6-(4-chloro-3-triptoreline)-5-(4-forfinal)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml at ambient temperature 30 mg ethylmethylamine dissolved in 0.5 ml of dry dichloromethane (colourless solution). Syringe with stirring, added dropwise to 50 mg of phosphorus oxychloride. The stirring at ambient temperature is continued for 1.5 h, resulting in a pink-orange solution. Then with a syringe and added dropwise to 60 mg of the original substance dissolved in 1 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 2 hours the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 5 minutes the mixture is Then extracted with two portions of diethyl ether and 10 ml. Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and receive 80 mg of the crude compound as a yellow oil. RP HPLC: retention Time of compound: 1,55 minutes

Example P2: Obtaining N'-[5-bromo-6-(4-chloro-3-triptoreline)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

a) Receiving 5-bromo-6-(4-chloro-3-triptoreline)-2-methylpyridin-3-ylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a refrigerator, 140 mg of crude 3-bromo-2-(4-chloro-3-triptoreline)-6-methyl-5-nitropyridine mix of 0.50 ml of methanol (yellow suspension). When cooled in a bath of ice water with a syringe and added dropwise to 0.50 ml of concentrated aqueous HCl solution (precipitation). Bath with ice to be removed and added in several portions 322 mg anhydrous SnCl2. Stirring while boiling under reflux continued for 4.5 hours (yellow solution). After cooling the mixture to ambient temperature it was concentrated in vacuo and receives a yellow oil. After addition of AcOEt add 5 ml of 4 M aqueous NaOH solution (pH 12). After extraction phase containing AcOEt, dried over Na2SO4, filtered and the solvent is removed in vacuum and receive 150 mg of a yellow oil. Purification of the residue is performed using flash chromatography [cartridge with silica gel (20 g, 60 ml) and a mixture of heptane/ethyl acetate 2:1 (by vol.:about.)] and receive 80 mg of the compound as a pale yellow solid. RP HPLC: retention Time of compound 2,04 minutes

b) Obtaining N'-[5-bromo-6-(4-chloro-3-triptoreline)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml of 36.5 mg ethylmethylamine when the ambient temperature is dissolved in 0.5 ml of dry dichloromethane (colourless solution). Syringe with stirring, added dropwise 0,038 ml of phosphorus oxychloride. The stirring at ambient temperature is continued for 1.75 hours, resulting in a pink-orange solution. To this solution was injected dropwise added 80 mg of 5-bromo-6-(4-chloro-3-triptoreline)-2-methylpyridin-3-ylamine dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 45 minutes the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with two portions of diethyl ether and 10 ml. Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and receive 80 mg of the crude compound as a yellow oil. (the mixture of E - and Z-isomers).

1H NMR (400 MHz, CDCl3): δ 1,15-1,35 (broad, 3H), of 2.34 (s, 3H), 3,03 (s, 3H), 3.25 to of 3.60 (broad, 2H), 7,16 and 7,19 (dd, 1H), 7,35 (s, 1H), 7,42 (m, 1), was 7.45 (m, 1H), 7,30-of 7.55 (broad, 1H).

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 2:1 (by vol.:vol.); Rfconnection = 0,27.

Example P3: Obtaining N'-[6-(4-chloro-3-triptoreline)-2-methyl-5-trimethylsilylethynyl-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 2-(4-chloro-3-triptoreline)-6-methyl-5-nitro-3-trimethylsilylmethylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a fridge, 220 mg of 3-bromo-2-(4-chloro-3-triptoreline)-6-methyl-5-nitropyridine dissolved in 4.0 ml of Diisopropylamine and the solution is stirred in an argon atmosphere at ambient temperature. After 20 minutes add 15 mg of copper iodide and 56 mg of bis(triphenylphosphine)paradigalla. Then added dropwise of 0.081 ml of amenitieseven. Thus obtained red solution was stirred at 70°C for 5 hours After cooling the mixture to ambient temperature it was concentrated in vacuo and obtain 490 mg of a brown solid. Purification of this crude product is performed using flash chromatography using a cartridge with silica gel (20 g; 60 ml) and a mixture of heptane/ethyl acetate 98:2 (by vol.:about.) and receive 40 mg of the compound as a brown oil.

TLC: Plates: Merck DC-Platten, silicia the ü F 254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 2:1 (by vol.:vol.); Rfconnection = 0,63.

b) Receiving 6-(4-chloro-3-triptoreline)-5-ethinyl-2-methylpyridin-3-ylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a fridge, 35 mg of 2-(4-chloro-3-triptoreline)-6-methyl-5-nitro-3-trimethylsilylmethylamine mix of 0.50 ml of methanol. When cooled in a bath of ice water with a syringe and added dropwise to 0.50 ml of concentrated aqueous HCl (observed loss of small amounts of sediment). Bath with ice and remove portions add 77 mg anhydrous SnCl2. Stirring while boiling under reflux continued for 2 hours After cooling the mixture to ambient temperature it was concentrated in vacuo and get a brown solid. After addition of AcOEt add 5 ml of 4 M aqueous NaOH solution (pH 12). After extraction phase containing AcOEt, dried over Na2SO4, filtered and the solvent is removed in vacuum and receive 30 mg of brown oil. Purification of the residue is performed using flash chromatography [cartridge with silica gel (5 g, 20 ml) and a mixture of heptane/ethyl acetate 3:1 (by vol.:about.)] and obtain 7 mg of fraction 1, 6-(4-chloro-3-triptoreline)-2-methyl-5-trimethylsilylethynyl-3-ylamine, and 15 mg fraction 2, the desired compound in the form of a brown solid. RP HPLC: retention Time of compound: 1,87 minutes

C) Obtaining N'-[6-(4-chloro-3-triptoreline)-2-methyl-5-trimethylsilylethynyl-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 10 ml 3.1 mg ethylmethylamine when the ambient temperature is dissolved in 0.25 ml of dry dichloromethane (colourless solution). Syringe with stirring, added dropwise 0,0032 ml of phosphorus oxychloride. The stirring at ambient temperature is continued for 1.0 hour, resulting in a pink-orange solution. To this solution with a syringe and added dropwise to 7.0 mg of 6-(4-chloro-3-triptoreline)-2-methyl-5-trimethylsilylethynyl-3-ylamine dissolved in 0.75 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at room temperature for 2.5 hours the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 15 minutes the mixture is Then extracted with two portions of diethyl ether and 10 ml. Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 6.0 mg of the compound as a yellow Maslov HPLC: retention Time of compound: 1,61 minutes

Example P4: Obtaining N'-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 3-bromo-6-methyl-2-(4-methylpentylamino)-5-nitropyridine:

In odnogolosy round bottom flask of 50 ml volume of 1.00 g of 3-bromo-6-methyl-5-nitropyridine-2-ol are dissolved 4.50 ml of dry dioxane and stirred in an argon atmosphere at ambient temperature (yellow-orange suspension). Add 0,593 ml of 4-methyl-1-pentanol and 2,354 g of triphenylphosphine. Then a syringe over 10 min added dropwise 0,801 ml of diethylazodicarboxylate (DEAD), while adding moderate heat. Stirring is continued at ambient temperature for 4.5 hours and Then the reaction stopped by adding 10 ml of water (pH=5-6), then the mixture is extracted with pentane (3×20 ml). The combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and get to 1.87 g of compound as a yellow-orange oil.

TLC: Plates: Merck DC-Platten, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfconnection = 0,72.

b) Receiving 5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-ylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with holodilny the Ohm, of 1.36 g of the crude 3-bromo-6-methyl-2-(4-methylpentylamino)-5-nitropyridine dissolve to 3.15 ml of methanol and the resulting solution is stirred. When cooled in a bath of ice water with a syringe and added dropwise 3,15 ml of concentrated aqueous HCl (observed precipitation). Bath with ice to be removed and added in several portions of 2.23 g of anhydrous SnCl2. Stirring while boiling under reflux continued for 5.5 h (yellow suspension). After cooling the mixture to ambient temperature it was concentrated in vacuo and receives a yellow solid. After adding dichloromethane, add 10 ml of 4 M aqueous NaOH solution (pH 12). After extraction the organic phase is dried over Na2SO4, filtered and the solvent is removed in vacuum and gain of 1.62 g of a yellow oil. Purification of the residue is performed using flash chromatography [cartridge with silica gel (50 g, 150 ml) and a mixture of heptane/ethyl acetate 4:1 (by vol.:about.)] and obtain 490 mg of the compound as a yellow oil. RP HPLC: retention Time of compound: 2,12 minutes

c) Obtaining N'-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask of 50 ml volume 182 mg ethylmethylamine dissolved in 3.0 ml of dry dichloromethane (colourless solution). Syringe with stirring at the temperature of the environment added dropwise 0,191 ml of phosphorus oxychloride. The stirring at ambient temperature is continued for 1.75 hours, resulting in a pink-orange solution. Then with a syringe and added dropwise to 300 mg of 5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-ylamine dissolved in 1.50 ml of dry dichloromethane, the solution becomes yellow. Stirring is continued at ambient temperature for 5 h Then the solution was poured into a mixture of ice/water (pH of the aqueous phase = 2). To create a pH of approximately 11, added 2 M aqueous NaOH solution and the mixture is stirred for 10 minutes the mixture is Then extracted with two portions of diethyl ether and 10 ml. combined ether phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 380 mg of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6N), 1,15-of 1.40 (m, m, 5H), to 1.61 (m, 1H), 1,78 (m, 2H), of 2.38 (s, 3H), 3.04 from (broad, 3H), 3.25 to of 3.60 (broad, 2H), 4,30 (t, 2H), 7,28 (s, 1H), 7,30-7-50 (broad, 1H).

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfconnection = 0,48.

Example P5: Obtaining N'-[5-(4-chlorophenyl)-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 10 ml, equipped with a fridge (the device is dried by flame), 160 mg is eojidanno N'-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-N-ethyl-N-methylformamidine and 167,5 mg p-Chlorfenvinphos acid dissolved in 1.20 ml of dioxane. To this solution in an argon atmosphere at ambient temperature is added 162 mg K3PO4in of 0.60 ml of water. The obtained two-phase mixture Tegaserod in an argon atmosphere for 20 min, then add 3.0 mg of tricyclohexylphosphine and 2.6 mg of bis(benzylideneacetone)palladium. The resulting suspension is vigorously stirred at a temperature of 100°C for 5 hours the Mixture allowed to warm to ambient temperature, then add 5.0 ml of a saturated aqueous solution of NH4Cl. The aqueous phase is extracted with AcOEt. The organic phase is dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 220 mg of a yellow oil. Purification of the residue via flash chromatography using a cartridge with silica gel (20 g; 60 ml) and a mixture of heptane/ethyl acetate 9:1 then 4:1, then 3:2 (vol.:about.) give 80 mg of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,88 (d, 6N); of 1.20 (t, 3H), of 1.23 (m, 2H), 1,58 (m, 1H), 1,72 (m, 2H), 2,44 (s, 3H), to 3.02 (s, 3H), 3,15-of 3.60 (broad, 2H), 4,29 (t, 2H), 7,06 (s, 1H), 7,34 (d, 2H), 7,42 (broad, 1H), 7,52 (d, 2H).

Example P6: Obtaining N-ethyl-N-methyl-N'-[2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-formamidine:

In odnogolosy round bottom flask with a volume of 50 ml flame dried) 150 mg N'-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-N-ethyl-N-methylformamidine dissolved in 1.0 ml of absolute THF and stirred in the atmosphere is e argon. The solution is cooled to -82°C (cooling bath with a mixture of solid carbon dioxide/acetone). Syringe with stirring, added dropwise to 0.263 ml, 1.6 M solution of n-utility in hexane. Stirring is continued at -82°C for 45 minutes Then with a syringe and added dropwise 0,091 ml trimethylchlorosilane and stirring is continued at -82°C for 3 h then the reaction mixture is allowed to warm to ambient temperature. Then the reaction is stopped by adding 0,020 ml Asón, then 5.0 ml of water. The aqueous phase is extracted with diethyl ether and the organic phase is dried over sodium sulfate, filtered and the solvent is removed in vacuum and receive 30 mg yellow oil. Then the pH value of the aqueous phase was adjusted to 7 by adding 10 ml of a saturated aqueous solution of NaHCO3. The mixture is then extracted with diethyl ether, the organic phase is dried, filtered and concentrated in vacuo and receive 90 mg of a yellow oil. Two oily fractions are combined and purified using flash chromatography [cartridge with silica gel (20 g, 60 ml) and a mixture of heptane/ethyl acetate 95:5, then 9:1, then 4:1 (by vol.:about.)] and receive 30 mg of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ of 0.90 (d, 6H), of 1.20 (t, 3H), of 1.33 (m, 2H), 1,60 (m, 1H); to 1.76 (m, 2H), 2,41 (s, 3H), 2,99 (s, 3H), 3,20-3,50 (broad, 1H), 3,35 (broad, 1H), 4,18 (t, 2H), 6,46 (d, 1H), 7,01 (d, 1H), 7,38 (broad, 1H).

RP HPLC: a Time to keep the project connection: 1,26 minutes

Example P7: Obtaining N'-[6-(4-chloro-3-triptoreline)-5-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 2-chloro-3-methyl-5-nitropyridine:

In a three-neck round bottom flask with a volume of 350 ml, equipped with a magnetic stirrer, thermometer, dropping funnel and reflux condenser, was placed 3-methyl-5-nitropyridine-2-ol (23.1 g) and 1,2-dichloroethane (150 ml). Added dropwise phosphorus oxychloride (17 ml). To this mixture at room temperature is added dropwise DMF (dimethylformamide) (11.5 ml). The reaction mixture is heated with stirring at 70°C for 0.5 hours, After cooling the mixture to ambient temperature it was concentrated in vacuo at 50°C and obtain a brown oily resinous substance. Cleaning this resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 7:3 (vol.:about.) gives 23,34 g of compound as a pale yellow solid (TPL: 40-42°C).

1H NMR (400 MHz, CDCl3): δ by 2.55 (s, 3H, CH3), 8,35 (d, 1H), 9,11 (d, 1H).

b) Obtaining 2-(4-chloro-3-triptoreline)-3-methyl-5-nitropyridine:

In a two-neck round bottom flask of 250 ml, equipped with a magnetic stirrer, thermometer and reflux condenser, are placed DMF (50 ml), 4-chloro-3-triptoreline (4.6 g), 2-chloro-3-methyl-5-nor is retiredin (4.0 g) and potassium carbonate (6.4 g). The reaction mixture is heated at 100°C for 2.5 hours, After cooling the mixture to room temperature it was poured into water (200 ml). The mixture is then extracted with ethyl acetate (2×40 ml). The combined organic layers dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 6,10 g of compound as yellow solid (TPL: 95-97°C).

1H NMR (400 MHz, CDCl3): δ 2.50 each (s, 3H, CH3), 7,30 (d×d, 1H), 7,49 (d, 1H), 7,55 (d, 1H), 8,35 (d, 1H), 8,80 (d, 1H).

c) Receiving 6-(4-chloro-3-triptoreline)-5-methylpyridin-3-ylamine:

In a two-neck round bottom flask of 250 ml, equipped with a KPG stirrer, thermometer and reflux condenser, placed in ethanol (100 ml), water (10 ml), iron (3.11 g) and 37% hydrochloric acid solution (0.3 ml). The reaction mixture is heated at 50°C. Portions add 2-(4-chloro-3-triptoreline)-3-methyl-5-nitropyridine (of 5.81 g). The mixture is refluxed for 2 hours, After cooling the mixture to 50°C. it is filtered through celite. The filtrate was poured into water (200 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 4,20 g of compound as yellow solid (TPL: 92-94°C).

1H NMR (400 MHz, CDCl3): δ of 2.25 (s, 3H, CH3), 3,55 (s br, 2H, NH2), 6,98 (d, 1H), 7,14 (d×d, 1H), 7,38 (d, 1H), 7,45 (d, 1H), 7,52 (d, 1H).

d) Obtaining N'-[6-(4-chloro-3-triptoreline)-5-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml ethylmethylamine (350 mg) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0.4 ml). The stirring at ambient temperature is continued for 1 h, resulting in a pink-orange solution. To this solution with a syringe and added dropwise 6-(4-chloro-3-triptoreline)-5-methylpyridin-3-ylamine (0.6 g)dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 1 h the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Cleaning this resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 1:2 (vol.:about.) give 0.52 g of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), of 2.28 (s, 3H, CH3), to 3.00 (s, 3H, CH3), 3,28-of 3.53 (m, 2H, CH2), 7,15-7,26 (m, 2H), 7,40 (d, 1H), 7,46 (d, 1H), 7,55 (sbr, 1H), 7,65 (d, 1H).

Example P8: Obtaining N'-[6-(4-chloro-3-triptoreline)-5-methylpyridin-3-yl]-N-ethyl-N-pyridine-2-informativna:

In odnogolosy round bottom flask with a volume of 25 ml of N-methyl-N-pyridin-2-informed (0.5 ml) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0.4 ml). The stirring at ambient temperature is continued for 1 h To this solution with a syringe and added dropwise 6-(4-chloro-3-triptoreline)-5-methylpyridin-3-ylamine (0.6 g)dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 1 h the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Cleaning this resinous substance using flash chromatography on silica gel using mixture is hexane/ethyl acetate 1:1 (by vol.:about.) give 0.33 g of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 2,34 (t, 3, CH3), 3,53 (s, 3H, CH3), of 6.96 (d, 1H), 7.00 the (d×d, 1H), 7,21 (d×d, 1H), 7,38 (d, 1H), 7,45-7,51 (m, 2H), 7.68 per-7,72 (m, 1H), 7,79 (d, 1H), 8,33 (d×d, 1H), 9,11 (s, 1H).

Example P9: Receive [6-(4-chloro-3-triptoreline)-5-methylpyridin-3-yl]-(1-pyrrolidin-1-methylidene)-amine:

In odnogolosy round bottom flask with a volume of 25 ml pyrrolidin-1-carbaldehyde (0.4 ml) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0.4 ml). The stirring at ambient temperature is continued for 1 h To this solution with a syringe and added dropwise 6-(4-chloro-3-triptoreline)-5-methylpyridin-3-ylamine (0.6 g)dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 1 h the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Cleaning this resinous substance (0.7 g) using flash chromatography on silica gel using ethyl acetate Mae is 0,59 g of compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 1,95 (mbr, 4H, 2×CH2), of 2.28 (s, 3H, CH3), 3,50-3,55 (m, 4H, 2×CH2), 7,17 (d×d, 1H), 7.23 percent (d, 1H), 7,39 (d, 1H), 7,55 (d, 1H), to 7.64 (d, 1H), of 7.75 (s, 1H).

Example P10: Obtaining N'-[6-(3-tertBUTYLPEROXY)-5-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 2-(3-tertBUTYLPEROXY)-3-methyl-5-nitropyridine:

In a two-neck round bottom flask of 50 ml volume, equipped with a magnetic stirrer, thermometer and reflux condenser, are placed DMF (50 ml), 3-tert-butylphenol (1.5 g), 2-chloro-3-methyl-5-nitropyridine (1.73 g) and potassium carbonate (2.76 g). The reaction mixture is heated at 60°C for 2 hours, After cooling the mixture to room temperature it was poured into water (200 ml). The mixture is then extracted with ethyl acetate (2×40 ml). The combined organic layers dried over sodium sulfate, filtered and the solvent is removed in vacuum. Purification of this crude substances by means of flash chromatography on silica gel using mixtures of hexane/ethyl acetate 4:1 (by vol.:about.) give 2.55 g of the compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ of 1.30 (s, 9H, 3×CH3), 2,48 (s, 3H, CH3), to 6.95 (d×d, 1H), 7,18 (m, 1H), 7,30-7,41 (m, 2H), 8,30 (d, 1H), cent to 8.85 (d, 1H).

b) Receiving 6-(3-tertBUTYLPEROXY)-5-methylpyridin-3-ylamine:

In a two-neck round bottom flask of 100 ml equipped with a KPG stirrer, thermometer obratnym refrigerator, put ethanol (50 ml), water (5 ml), iron (1,43 g) and 37% hydrochloric acid solution (0.2 ml). The reaction mixture is heated at 50°C. Portions add 2-(3-tertBUTYLPEROXY)-3-methyl-5-nitropyridine (of 2.26 g). The mixture is refluxed for 3 hours After cooling the mixture to 50°C. it is filtered through celite. The filtrate was poured into water (200 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuum. Purification using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 1:1 (by vol.:about.) give 1.10 g of the compound as a brownish solid (TPL: 83-84°C).

1H NMR (400 MHz, CDCl3): δ 1.32 to (s, N, 3×CH3in ), 2.25 (s, 3H, CH3), 3,35 (sbr, 2H, NH2), to 6.75 (d×d, 1H), 6,80 (d, 1H), 7,07-to 7.15 (m, 2H), 7.23 percent (d, 1H), 7,55 (d, 1H).

C) Obtaining N'-[6-(3-tertBUTYLPEROXY)-5-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml ethylmethylamine (350 mg) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0.4 ml). The stirring at ambient temperature is continued for 0.5 h, resulting in a pink-orange R is the target. To this solution with a syringe and added dropwise 6-(3-tertBUTYLPEROXY)-5-methylpyridin-3-ylamine (0.51 g), dissolved in 5.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 2 hours the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Cleaning this resinous substance using flash chromatography on silica gel using ethyl acetate to give 0.56 g of the compound as a brown oil.

1H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), of 1.30 (s, 9H, 3×CH3), of 2.28 (s, 3H, CH3), to 3.00 (s, 3H, CH3), of 3.25 to 3.35 (mbr, 2H, CH2), to 6.80 (d×d, 1H), 7,08 for 7.12 (m, 2H), 7,20-7,27 (m, 2H), 7,53 (sbr, 1H), to 7.67 (d, 1H).

Example P11: Obtaining N'-[6-(3,4-dichlorophenoxy)-2,4-diisopropylidene-3-yl]-N,N-dimethylformamidine:

In odnogolosy a round bottom flask of 25 ml volume, equipped with a reflux condenser, was placed dimethylformamidine (1.6 g), DMF (10 ml) and 6-(3,4-dichlorophenoxy)-2,4-diisopropylidene-3-ylamine (1.70 g). The reaction mixture is refluxed and the ethanol is distilled off within 2.5 hours The mixture is then concentrated in vacuo at 50°C. the Crude substance is crystallized from a mixture of hexane/coluracetam 4:1 (by vol.:about.) and gain of 1.41 g of compound as a white solid (TPL: 102-103°C).

1H NMR (400 MHz, CDCl3): δ 1,11-1,17 (2q, 12H, 4×CH3), 3,20 (s, 6H, 2×CH3), is 3.08-3,20 (m, 2H), between 6.08 (s, 1H), 6,85 (d×d, 1H), 7,14 (s, 1H), 7,28 (d, 1H), 7,37 (d, 1H).

Example R: Obtaining N'-[6-(2,4-dichlorophenoxy)pyridine-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml ethylmethylamine (350 mg) at ambient temperature was dissolved in dry dichloromethane (4 ml) environment (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0.4 ml). The stirring at ambient temperature is continued for 1 h To this solution with a syringe and added dropwise 6-(2,4-dichlorophenoxy)pyridine-3-ylamine (0.5 g)dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 1 h the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in VA is uume. Purification using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 3:4 (vol.:about.) gives 0.31 g compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 1.18 to to 1.23 (t, 3H, CH3), 2,98 (s, 3H, CH3), 3,25-3,51 (mbr, 2H, CH2), at 6.84-6.89 in (d, 1H), to 7.09 (d, 1H), 7.23 percent (d×d, 1H), 7,35 (d×d, 1H), 7,45 (d, 1H), 7.50 for (sbr, 1H), of 7.75 (d, 1H).

Example P13: Obtaining N'-[6-(4-chloro-3-triptoreline)-4-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

a) Obtaining 2-chloro-4-methyl-5-nitropyridine:

In a three-neck round bottom flask with a volume of 100 ml, equipped with a magnetic stirrer, thermometer, dropping funnel and reflux condenser, was placed 4-methyl-5-nitropyridine-2-ol (5.0 g), and 1,2-dichloroethane (30 ml). Added dropwise phosphorus oxychloride (3.6 ml). To this mixture at ambient temperature is added dropwise DMF (2.5 ml). With stirring, the reaction mixture is heated at 70°C for 0.5 hours, After cooling the mixture to ambient temperature it was concentrated in vacuo at 50°C and obtain a brown oily resinous substance. Cleaning this resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 7:3 (vol.:about.) gives 4,91 g of compound as a pale yellow solid (TPL: 35-38°C).

1H NMR (400 MHz, CDCl3): δ of 2.68 (s, 3H, CH3/sub> ), 7,38 (d, 1H), 8,98 (d, 1H).

b) Obtaining 2-(4-chloro-3-triptoreline)-4-methyl-5-nitropyridine:

In a two-neck round bottom flask of 250 ml, equipped with a magnetic stirrer, thermometer and reflux condenser, are placed DMF (30 ml), 4-chloro-3-triptoreline (4.5 g), 2-chloro-4-methyl-5-nitropyridine (4.0 g) and potassium carbonate (6.4 g). The reaction mixture was stirred at ambient temperature for 1 h, poured into water (300 ml), acidified with 5 M HCl solution (15 ml)and then extracted with ethyl acetate (4×50 ml). The combined organic layers washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuum. Purification using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 7:3 (vol.:about.) gives 7,03 g of compound as a red solid (TPL: 75-80°C).

1H NMR (400 MHz, CDCl3): δ 2,70 (s, 3H, CH3), 6,93 (s, 1H), 7,28 (d×d, 1H), 7,49 (d, 1H), 7,56 (d, 1H), 8,35 (s, 1H).

c) Receiving 6-(4-chloro-3-triptoreline)-4-methylpyridin-3-ylamine:

In a two-neck round bottom flask of 100 ml equipped with a KPG stirrer, thermometer and reflux condenser, placed in ethanol (50 ml), water (5 ml), iron (1.29 g) and 37% hydrochloric acid solution (0.2 ml). The reaction mixture is heated at 50°C. Portions add 2-(4-chloro-3-cryptomite is phenoxy)-4-methyl-5-nitropyridine (2.4 g). The mixture is refluxed for 1 h After cooling the mixture to 50°C. it is filtered through celite. The filtrate was poured into water (100 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuum. Purification using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 1:1 (by vol.:about.) give 1.90 g of the compound as a brownish solid (TPL: 105-107°C).

1H NMR (400 MHz, CDCl3): δ of 2.23 (s, 3H, CH3), 3,50 (sbr, 2H, NH2), to 6.75 (s, 1H), 7,18 (d×d, 1H), 7,40 (d, 1H), 7,43 (d, 1H), 7,63 (d, 1H).

d) Obtaining N'-[6-(4-chloro-3-triptoreline)-4-methylpyridin-3-yl]-N-ethyl-N-methylformamidine:

In odnogolosy round bottom flask with a volume of 25 ml ethylmethylamine (349 mg) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0,37 ml). The stirring at ambient temperature is continued for 1 h, resulting in a pink-orange solution. To this solution with a syringe and added dropwise 6-(4-chloro-3-triptoreline)-4-methylpyridin-3-ylamine (605 mg), dissolved in 1.0 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at t is mperature environment within 1 hour The mixture is then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Cleaning this resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 1:1 (by vol.:about.) network of 0.67 g of compound as brownish oil.

1H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), is 2.30 (s, 3H, CH3), to 3.00 (s, 3H, CH3), 3,28-of 3.53 (m, 2H, CH2), 6,78 (s, 1H), 7,19 (d×d, 1H), 7,39 was 7.45 (m, 3H), 7,54 (s, 1H).

Example R: Obtaining N'-[6-(4-chloro-3-triptoreline)-4-methylpyridin-3-yl]-N-methyl-N-(1-methylprop-2-inyl)-formamidine:

a) Obtaining N-methyl-N-(1-methylprop-2-inyl)formamide:

In a three-neck round bottom flask with a volume of 350 ml, equipped with a magnetic stirrer, thermometer, device, Dean-stark for the Department of water and reflux condenser, was placed methyl-(1-methylprop-2-inyl)-amine (8,31 g) and toluene (100 ml). Added dropwise formic acid (6.9 g). The reaction mixture is refluxed for 2 hours, After cooling the mixture to ambient temperature it was concentrated in vacuo at 50°C and receive coric ewww liquid. Purification using silica gel and a mixture of hexane/ethyl acetate 1:1 (by vol.:about.) give 4.83 g of the compound as a brownish liquid.

1H NMR (400 MHz, CDCl3): δ 1,38+1,49 (2d, 3H, CH3), 2,30+2,43 (2d, 1H, CH), 2,90+2,98 (2s, 3H, CH3), to 4.62+5,38 (2m, 1H, CH), 6,78 (s, 1H), 7,99+8,16 (2s, 1H).

b) Obtaining N'-[6-(4-chloro-3-triptoreline)-4-methylpyridin-3-yl]-N-methyl-N-(1-methylprop-2-inyl)-formamidine:

In odnogolosy round bottom flask with a volume of 25 ml of N-methyl-N-(1-methylprop-2-inyl)-formamide (223 mg) at ambient temperature was dissolved in dry dichloromethane (4 ml) (colourless solution). Syringe with stirring, added dropwise a mixture of phosphorus oxychloride (of 0.18 ml) and dichloromethane (1 ml). The stirring at ambient temperature is continued for 1 h To this solution with a syringe and added dropwise 6-(4-chloro-3-triptoreline)-4-methylpyridin-3-ylamine (303 mg), dissolved in 10 ml of dry dichloromethane, and receives a yellow solution. Stirring is continued at ambient temperature for 3 hours the mixture is Then poured into a mixture of ice/water (pH of the aqueous phase = 2). Then to create a pH of approximately 11, added 2 M aqueous NaOH solution and stirring is continued for 10 minutes the mixture is Then extracted with dichloromethane (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is dilaut in vacuum. Cleaning this resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 3:2 (vol.:about.) give 198 mg of the compound as a brownish oil.

1H NMR (400 MHz, CDCl3): δ 1,38+1,48 (2d, 3H, CH3), of 2.20 (s, 3H, CH3), 2,30+2,40 (2d, 1H, CH), 2,89+2,98 (2s, 3H, CH3), 4,43+5,38 (2m, 1H, CH), 6,72 (s, 1H), 7,15 (d×d, 1H), 7,38 (d, 1H), 7,42 (d, 1H), 7.62mm (s, 1H), 7,98+8,15 (2s, 1H).

The technique OF HPLC

The HPLC firm Agilent: quadratic pump HP1100 HPLC detector with variable wavelength NR, thermostatted block column HP1100 and device for degassing solvent NR.

A = water with 0.04% HCOOH, B = acetonitrile/methanol (4:1, vol/about.) + 0.05% HCOOH

Column: Phenomenex Gemini C18, particle size 3 μm, 110 Angstrom, 30×3 mm,

temperature: 60°C.

When using gradient mode was introduced following mixture:

TimeAnd%In%With%D%Flow rate (ml/min)
0,0095,05,00,00,01,700
2,000,0100,0 0,00,01,700
2,800,0100,00,00,01,700
2,9095,05,00,00,01,700
3,1095,05,00,00,01,700

Example R: Obtaining 2-(4-methylpentylamino)-5-nitropyridine

In pathology reaction flask with a volume of 350 ml (mechanical stirrer, dropping funnel and thermometer) 3-hydroxy-1H-pyridine-2-he [SA registration No. 626-06-2] (35,0 g) at ambient temperature suspended in water (120 ml). Within 10 minutes under stirring portions add sodium hydroxide (13,48 g), there is an exothermic reaction. Then to achieve a temperature of 0°C, the mixture is placed in a cooling bath (common salt/crushed ice). Then for 15 min add dimethylsulfate (41,72 g) while cooling and stirring is continued. Then the cooling gap the surrounding bath is removed and the mixture is stirred at room temperature overnight. The mixture is then extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and the solvent is removed in vacuum and get a dark brown viscous substance.

This substance is transferred in 112 ml of concentrated sulfuric acid and the mixture is placed in pathology the reaction flask with a volume of 350 ml After stirring and cooling in a bath of ice water for 1.5 h added dropwise a freshly prepared solution of the mixture of acids [freshly prepared from sulfuric acid and 31.7 ml) and fuming nitric acid (31.8 ml)], keeping the temperature below 15°C. Stirring is continued at temperatures below 10°C for a further 45 minutes the mixture is Then carefully transferred into ice and then add water (just get 700 ml of the aqueous phase). The resulting precipitate is stirred for 40 min, then filtered and the filter cake washed with water and after drying gain of 19.6 g of orange solid.

In pathology reaction flask with a volume of 350 ml, equipped with a fridge, a suspension of this intermediate product (of 5.00 g) in dry dioxane (30,0 ml) was stirred at room temperature. First, add 1-bromo-4-methylpentan (of 5.82 g), then the silver oxide (13,62 g). The resulting suspension is stirred at the boil under reflux for 13.5 hours After cooling to room temperature, add ethyl acetate (5 ml) and the mixture is filtered through a layer of Hyflo and washed with ethyl acetate (50 ml). The organic phase is washed with water and brine, then dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 4,00 g orange oil. This crude product was then purified using chromatography on silica gel (eluent: hexane/ethyl acetate 9:1 (by vol.:vol.)). So get 1,49 g of the desired compound as a yellow solid (TPL: 48-49°C).

1H NMR (400 MHz, CDCl3): δ to 0.92 (d, 6H), 1.32 to (m, 2H), 1,62 (m, 1H), to 1.86 (m, 2H), 3.96 points (s, 3H), 4,48 (t, 2H), 7,76 (d, 1H), 7,68 (d, 1H).

LC: UV detection: 220 nm; Rt=2,08 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,63.

Example P16: Obtain 2-bromo-5-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine:

In pathology reaction flask with a volume of 50 ml, equipped with a fridge, 5-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine (70 mg) was dissolved in dry acetonitrile (0,50 ml) and stirred at room temperature. With stirring, add N-bromosuccinimide (55 mg). Stirring while boiling under reflux continued for 1.25 hours Then added 2 M aqueous solution of sodium hydroxide (20 ml, pH 10) and the mixture extracted with ether (3 times 20 ml). The organic layer is washed with 10% aqueous solution bisul the ITA sodium (20 ml). Ambassador drying over sodium sulfate the organic layer was filtered and the solvent is removed in vacuum and receive 40 mg of a brown resinous substance. After chromatography on silica gel (eluent: hexane/ethyl acetate 2:1 (by vol.:about.) gain of 6.3 mg of the desired compound as a red oil.

1H NMR (400 MHz, CDCl3): δ of 0.90 (d, 6H), of 1.29 (m, 2H), 1,60 (m, 1H), 1,79 (m, 2H), to 3.67 (s, 3H), 3,81 (s, 3H), 4.26 deaths (t, 2H), is 6.61 (s, 1H).

LC: UV detection: 220 nm; Rt=1,94 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:2 (vol.:vol.); Rfthe desired connection = 0,47.

Example R17: Obtain 6-(4-methylpentylamino)-3-nitropyridine-2-ylamine:

A) In a three-neck round bottom flask of 100 ml equipped with a refrigerator and thermometer, sodium hydride (of 2.51 g of a 55% suspension in mineral oil) is suspended in dry tetrahydrofuran (15 ml) and add hexamethyldisilazane (0,60 ml) and the mixture is stirred in an argon atmosphere at room temperature for 20 minutes by Syringe with stirring dropwise within 10 min add 4-methyl-1-pentanol (of 7.23 ml), resulting in gas and increasing the temperature to 31°C. Stirring is continued for another 50 minutes

B) In pathology reaction flask with a volume of 200 ml, provided with a mechanical the second mixer, addition funnel, a refrigerator and a thermometer, 6-chloro-3-nitropyridine-2-ylamine (5,00 g, see registration No. 27048-04-0) in an argon atmosphere at room temperature, suspended in dry tetrahydrofuran (15 ml). Under stirring for 15 min in small portions add the suspension obtained as described in paragraph (a). To maintain the temperature below 30°C from time to time use a cooling bath with a mixture of ice/water. To facilitate mixing, re-add dry tetrahydrofuran (20 ml). Stirring is continued for 3.5 hours and Then the reaction is stopped by the careful addition of excess water (50 ml). The mixture is then extracted with ether (2 x 60 ml). The organic phase is washed with brine, dried over sodium sulfate and filtered. Then the solvent is removed in vacuum and get 10,78 g of yellow-brown oil. Subsequent chromatography on silica gel (eluent: hexane/ethyl acetate 97:3 (by vol.:about.)) gives 6,89 g of the desired compound as a yellow solid (TPL: 57-58°C).

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6H), 1.28 (in m, 2H), 1,60 (m, 1H), about 1.75 (m, 2H), 4,28 (t, 2H), 4,90-to 8.20 (broad, 2H), 6,11 (d, 1H), 8,28 (d, 1H).

LC: UV detection: 220 nm; Rt=1,97 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfsearch soybean is inania = 0,22.

Example P18: Obtain 5-bromo-6-(4-methylpentylamino)-3-nitropyridine-2-ylamine:

In a three-neck round bottom flask of 50 ml volume, equipped with a refrigerator, 6-(4-methylpentylamino)-3-nitropyridine-2-ylamine (1,83 g) dissolved in dry acetonitrile (8,00 ml) and stirred in an argon atmosphere at room temperature. With stirring, add N-bromosuccinimide (1,36 g). Stirring while boiling under reflux continued for 3.5 hours Then add water (30 ml) and the mixture extracted with ether (2 x 60 ml). The organic layer is washed with 10% solution of sodium bisulfite (40 ml). Ambassador drying over sodium sulfate the organic layer was filtered and the solvent is removed in vacuum and get to 2.41 g of a dark red oil. After chromatography on silica gel (eluent: hexane/ethyl acetate 94:6 (vol.:about.) get to 1.87 g of the desired compound as a dark red oil.

1H NMR (400 MHz, CDCl3): δ to 0.92 (d, 6H), of 1.33 (m, 2H), 1,62 (m, 1H), is 1.81 (m, 2H), 4,34 (t, 2H), 4,70-to 8.40 (broad, 2H), charged 8.52 (s, 1H).

LC: UV detection: 220 nm; Rt=2,16 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,20.

Getting 5-chloro-6-(4-methylpentylamino)-3-nitropyridine-2-ylamine:

This connection can get anal is the same, of 6-(4-methylpentylamino)-3-nitropyridine-2-ylamine using N-chlorosuccinimide.

1H NMR (400 MHz, CDCl3): δ to 0.92 (d, 6H), 1.32 to (m, 2H), 1.61 of (m, 1H), is 1.81 (m, 2H), 4,36 (t, 2H), 4.80 to 8,30 (broad, 2H), of 8.37 (s, 1H).

LC: UV detection: 220 nm; Rt=2,13 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,18.

TPL: 53-54°C.

Example P19: Obtaining 2,5-dibromo-6-(4-methylpentylamino)-3-nitropyridine:

In odnogolosy round bottom flask of 25 ml volume of 1.41 ml of 48% aqueous Hydrobromic acid under stirring and cooling in a bath of ice water to maintain the temperature equal to the approximate room temperature, added dropwise to the sulfoxide (7,40 ml).

C) In a three-neck reaction flask with a volume of 50 ml, equipped with a fridge, 5-bromo-6-(4-methylpentylamino)-3-nitropyridine-2-ylamine (1,00 g) dissolved in dimethyl sulfoxide (3,70 ml). With stirring, add the potassium nitrite (1.07 g) and copper bromide (I) (90 mg). With stirring, the temperature of the support is equal to 35 to 38°C and for 5 min added dropwise a solution obtained as described in paragraph (a). Stirring is continued in the same temperature range for a further 18 h, the resulting get a dark brown suspension. After cooling to room temperature, the suspension is transferred into a feast upon the config aqueous solution of sodium carbonate (70 ml, pH 8). The mixture is extracted with ether (3 x 40 ml). The combined organic phases are dried over sodium sulfate and then filtered through a layer of silicon dioxide (placed on the surface of a disk of sintered glass filter). After washing with ether, the combined ether phase was concentrated in vacuo and obtain 790 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,93 (d, 6N), of 1.35 (m, 2H), and 1.63 (m, 1H), of 1.84 (m, 2H), 4,47 (t, 2H), 8,43 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,56.

Example P20: Obtain 3-bromo-2-(4-methylpentylamino)-5-nitro-6-phenylpyridine:

In a three-neck round bottom flask of 50 ml volume, equipped with a fridge, 2,5-dibromo-6-(4-methylpentylamino)-3-nitropyridine (200 mg) in an argon atmosphere dissolved in a mixture of toluene (to 6.00 ml) and ethanol (0.75 ml). With stirring, add potassium carbonate (159 mg) in water (0.95 ml), resulting in a gain of two-phase yellow mixture. Add phenylboronic acid (63,8 mg). Stirring at room temperature continued for 15 minutes, passing through a mix of current of argon. Then add tetrakis(triphenylphosphine)palladium (18,1 mg) and the solution is stirred while boiling under reflux in t is an increase of 3.5 hours The mixture is then stirred at room temperature overnight. Then add saturated aqueous solution of ammonium chloride (25 ml) and the mixture extracted with ether (2 x 30 ml). The organic phase is dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 220 mg of a yellow oil. After purification on silica gel (eluent: hexane/ethyl acetate, gradient mode from 100:0 to 98:2) to obtain 140 mg of a yellow oil containing a mixture of the desired compound (43%) with the following two by-products:

6-(4-methylpentylamino)-3-nitro-2-phenylpyridine 36%
2-(4-methylpentylamino)-5-nitro-3,6-diphenylpyridine 21%

This mixture without processing used in the next stage of recovery to obtain the corresponding anilines.

Example P21: Obtain 5-bromo-6-(4-methylpentylamino)-2-phenylpyridine-3-ylamine:

In a three-neck reaction flask of 25 ml volume, equipped with a fridge, obtained above mixture (140 mg) (mixture contains 3-bromo-2-(4-methylpentylamino)-5-nitro-6-phenylpyridine (43%), 6-(4-methylpentylamino)-3-nitro-2-phenylpyridine (35%) and 2-(4-methylpentylamino)-5-nitro-3,6-diphenylpyridine (21%)) is astonaut in methanol (0,50 ml). Under stirring and cooling in a bath of ice water are added dropwise 37% aqueous solution of hydrochloric acid (0.15 ml). After removal of the cooling bath add powdered tin (88 mg). The resulting suspension is stirred while boiling under reflux in a period of 3.25 hours the mixture is allowed to warm to room temperature and the methanol removed in vacuo. To the resulting orange resinous substance is added 2 M aqueous sodium hydroxide solution (10 ml). The mixture is extracted with ethyl acetate (2 x 20 ml). The organic layer is dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 130 mg of a yellow resinous substance. The crude substance is purified using chromatography on silica gel (eluent: hexane/ethyl acetate 97:3 (by vol.:vol.)). Receive 50 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6H), of 1.33 (m, 2H), 1.61 of (m, 1H), 1,79 (m, 2H), of 3.56 (s, 3H), or 4.31 (t, 2H), 7,33 (s, 1H), 7,37 (tt, 1H), 7,46 (td, 2H), 7,71 (dt, 2H).

LC: UV detection: 220 nm; Rt=2,30 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 3:1 (by vol.:vol.); Rfthe desired connection = 0,35.

In addition, there are also a mixture of the following two compounds as a yellow oil (53 mg).

6-(4-methylpentylamino)-2-phenylpyridine-3-ylamine
6-(4-methylpentylamino)-2,5-diphenylpyridine-3-ylamine

This mixture is directly used in the next stage.

Example P22: Obtaining N-ethyl-N-methyl-N'-[6-4-methylpentylamino]-2,5-diphenylpyridine-3-yl]-formamidine:

In the reaction vessel Supelco volume of 8 ml (closed membrane) ethylmethylamine (13,7 mg) at ambient temperature was dissolved in dry dichloromethane (3,00 ml) (colourless solution). Syringe with stirring, added dropwise phosphorus oxychloride (0,37 ml). The stirring at ambient temperature is continued for 1.5 h, the resulting receive light orange solution. To this solution with a syringe and added dropwise to 36.2 mg of a mixture of two obtained above by-products [mix consists of 6-(4-methylpentylamino)-2,5-diphenylpyridine-3-ylamine and 6-(4-methylpentylamino)-2-phenylpyridine-3-ylamine] in the form of a solution in dry dichloromethane (2.00 ml) and receive a light brown solution. Stirring is continued at ambient temperature for 3.5 hours the mixture is Then poured into a mixture of ice/water. Then to create a pH of approximately 12, add 2 M aq is th NaOH solution (10 ml) and stirring is continued for 10 minutes The mixture is then extracted with dichloromethane (2×20 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Clean yellow resinous substance using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 4:1 (by vol.:about.) network of 17.1 mg of the desired compound as a yellow oil (66%).

1H NMR (400 MHz, CDCl3): δ of 0.90 (d, 6H)and 1.15 (t, 3H), of 1.33 (m, 2H), 1,59 (m, 1H), 1,79 (m, 2H), 2,98 (s, 3H), 3,10-3,70 (broad, 2H), to 4.41 (t, 2H), 7,33 (mm, 8H), to 7.67 (dd, 2H), 8,18 (dd, 2H).

LC: UV detection: 220 nm; Rt=1,61 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 3:1 (by vol.:vol.); Rfthe desired connection = 0,18.

Example R23 is applied: Obtain 2-bromo-5-chloro-6-(4-methylpentylamino)-3-nitropyridine:

A) odnogolosy round bottom flask with a volume of 25 ml of 1.40 ml of 48% aqueous Hydrobromic acid under stirring and cooling in a bath of ice water to maintain the temperature equal to the approximate room temperature and added dropwise to the sulfoxide (7,30 ml).

B) In a three-neck reaction flask with a volume of 50 ml, equipped with a fridge, 5-chloro-6-(4-methylpentylamino)-3-nitropyridine-2-ylamine (850 mg) at room temperature was dissolved in dimethyl sulfoxide (3,70 ml). When re is eshiwani add potassium nitrite (1.06 g) and copper bromide (I) (89 mg). With stirring, the temperature of the support is equal to 35 to 38°C and for 6 min added dropwise a solution obtained as described in paragraph (a). Stirring is continued in the same temperature range for a further 20 h, resulting in a get a dark brown solution. After cooling to room temperature, the suspension is transferred into a saturated aqueous solution of sodium carbonate (50 ml, pH 9). The mixture is extracted with ether (3 times 50 ml). The combined organic phases are dried over sodium sulfate and then filtered through a layer of silicon dioxide (placed on the surface of a disk of sintered glass filter). After washing with ether, the combined ether phase was concentrated in vacuo and obtain 810 mg of the desired compound as a yellow oil. After purification by chromatography on silica gel (eluent: hexane/ethyl acetate 95:5 (vol.:about.)) obtain 870 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,93 (d, 6N), of 1.35 (m, 2H), and 1.63 (m, 1H), of 1.85 (m, 2H), 4,48 (t, 2H), 8,28 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,55.

Example R24: Obtain 5-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine:

In a three-neck reaction flask with a volume of 25 is l, equipped with a refrigerator, 3-methoxy-2-(4-methylpentylamino)-5-nitropyridine dissolved in methanol (2.00 ml). Under stirring and cooling in a bath of ice water added 37% aqueous hydrochloric acid solution (0,82 ml). After removal of the cooling bath add powdered tin (470 mg). Then, the resulting suspension is stirred at the boil under reflux for 3.5 hours the mixture is allowed to warm to room temperature and the methanol removed in vacuo. To the resulting yellow resinous substance is added 2 M aqueous sodium hydroxide solution (25 ml). The mixture is extracted with ethyl acetate (2 x 30 ml). The organic layer is dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 350 mg of brown oil. The crude substance is purified using chromatography on silica gel (eluent: hexane/ethyl acetate 2:1 (by vol.:vol.)). Obtain 170 mg of the desired compound (38,5%) as a red oil.

1H NMR (400 MHz, CDCl3): δ of 0.90 (d, 6N), of 1.30 (m, 2H), 1,59 (m, 1H), is 1.81 (m, 2H), 3,36 (s, 2H), 3,82 (s, 3H), 4,27 (t, 2H), 6,56 (d, 1H), 7,21 (d, 1H).

LC: UV detection: 220 nm; Rt=1,47 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,15.

In addition, also provide 70 mg of the mixture of the two side ol the product as a brown oil. This mixture is separated by repeated chromatography on silica gel (eluent: toluene/acetone 97:3 (by vol.:about.)) and receive the following connections:

Connection
2-chloro-5-methoxy-6-(4-methylpentylamino)-pyridine-3-ylamine 35 mg (86% together with about 14% of connections)
Connection
2,5-dimethoxy-6-(4-methylpentylamino)-pyridine-3-ylamine 55% (92% together with about 8% of compound (A)

Example P25: Obtaining 2-(4-methylpentylamino)-5-nitro-3,6-bis-triptoreline:

In odnogolosy round bottom flask with a volume of 10 ml, equipped with a fridge, 2,5-dibromo-6-(4-methylpentylamino)-3-nitropyridine (150 mg) is dissolved in dry dichloromethane (1,00 ml). To the resulting yellow solution was added methyl-2,2-debtor-2-(persulfonic)-acetate (377 mg), copper iodide (I) (90 mg) and hexamethylphosphoramide (HMPA) (350 mg). The resulting suspension is stirred while boiling under reflux for 6 hours Over the course of the reaction is monitored using19F-NMR (CDCl3). Stirring is continued at ambient temperature overnight. Then dobavlaut a saturated solution of ammonium chloride (30 ml) and the mixture extracted with ether (2×20 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum. Purification of the yellow oil (120 mg) using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 98:2 (by vol.:about.) give 100 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,92 (d, 6N), of 1.34 (m, 2H), and 1.63 (m, 1H), of 1.85 (m, 2H), 4,59 (t, 2H), 8,49 (s, 1H).

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane; Rfthe desired connection = 0,11.

Example R: Obtain 5-chloro-6-(4-methylpentylamino)-3-nitropyridine-2-carbonitrile:

In odnogolosy round bottom flask with a volume of 10 ml, equipped with an efficient refrigerator, 2-bromo-5-chloro-6-(4-methylpentylamino)-3-nitropyridine (200 mg) is dissolved in dry acetonitrile (3,00 ml). To the resulting yellow solution was added copper cyanide (I) (109 mg). The resulting suspension is stirred while boiling under reflux for 6 h, resulting in a get a brown solution. Over the course of the reaction is monitored by GC-MS (gas chromatography-mass spectrometry). Mixture is allowed to warm to ambient temperature. Then add a saturated solution of ammonium chloride (20 ml) with a small amount of ice and the mixture extracted with ether (2×20 ml)Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and receive 150 mg of the desired compound as a yellow oil (89%).

1H NMR (400 MHz, CDCl3): δ 0,93 (d, 6N), of 1.36 (m, 2H), and 1.63 (m, 1H), 1,87 (m, 2H), 4,54 (t, 2H), 8,53 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,28.

Example P27: Obtain 3-chloro-2-(4-methylpentylamino)-5-nitro-6-triptoreline:

In odnogolosy round bottom flask with a volume of 10 ml, equipped with an efficient refrigerator, 2-bromo-5-chloro-6-(4-methylpentylamino)-3-nitropyridine (150 mg) is dissolved in dry dimethylformamide (1.20 ml). To the resulting yellow solution was added methyl-2,2-debtor-2-(persulfonic)-acetate (256 mg), copper iodide (I) (102 mg) and hexamethylphosphoramide (HMPA) (400 mg). The resulting suspension is stirred and heated at 100°C for 2 hours Over the course of the reaction is monitored by GC-MS. The reaction mixture is allowed to warm to room temperature. Then add a saturated solution of ammonium chloride (30 ml, pH is approximately 3) and the mixture extracted with ether (2×30 ml). Then the combined organic phases are dried over sodium sulfate, filtered through a layer of silica gel and the solvent is removed in vacuum. Purification of the yellow oil (120 mg) using flash chromatography is as silica gel using mixtures of hexane/ethyl acetate 98:2 (by vol.:about.) give 120 mg of the desired compound as a yellow oil (83%).

1H NMR (400 MHz, CDCl3): δ of 0.93 (d, 6H), of 1.35 (m, 2H), 1,62 (m, 1H), to 1.86 (m, 2H), to 4.52 (t, 2H), compared to 8.26 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane; Rfthe desired connection = 0,11.

Example P28: Obtain 6-chloro-2-methoxy-3-nitropyridine:

A) In a three-neck round-bottom flask with a volume of 10 ml, equipped with a refrigerator and thermometer, sodium hydride (of 2.26 g of 0.55% dispersion in mineral oil) in an argon atmosphere suspended in dry dioxane (10 ml). Then add hexamethyldisilazane (0,81 ml). Syringe with stirring, added dropwise dry methanol (2.10 ml) (foaming, gas evolution). The temperature is kept lower than 34°C in a bath of ice water. After the addition stirring is continued at ambient temperature for 50 minutes To facilitate the subsequent transfer of the suspension (in another flask) re-added dioxane (10 ml).

In pathology reaction flask with a volume of 200 ml equipped with a refrigerator, a mechanical stirrer, addition funnel and thermometer, 2,6-dichloro-3-nitropyridine [SA registration No. 136901-10-5] (10.0 g)dissolved in dry dioxane (40 ml), stirred in an argon atmosphere. Within 12 minutes slowly add freshly prepared suspension obtained as described in paragraph (a) (REP the RNA foam and gas). To maintain the temperature below 32°C. using a cooling bath with a mixture of ice/water. Stirring at ambient temperature continued for 2 hours Over the course of the reaction is monitored by thin layer chromatography (see below). Then add water (50 ml, pH is approximately 8-9) and the mixture extracted with ether (2×50 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 10,45 g light yellow solid. Purification of the yellow oil (120 mg) using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 97:3 (by vol.:about.) give 8.00 g of the desired compound as a pale yellow solid (TPL: 73-74°C, yield: 82%).

1H NMR (400 MHz, CDCl3): δ 4,14 (s, 3H), 7,05 (d, 1H), 8,28 (d, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: hexane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,33, Rfeduct = 0,21.

Found only a small amount of the isomer of the desired compound and bis-methoxypyridine.

Example R29: Getting 2-methoxy-6-(4-methylpentylamino)-3-nitropyridine:

A) pathology reaction flask with a volume of 100 ml, equipped with a fridge, a mechanical stirrer, addition funnel and Ter what ometron, sodium hydride (1,16 g 0,55% dispersion in mineral oil) in an argon atmosphere suspended in dry dioxane (20 ml). Then add hexamethyldisilazane (of 0.44 ml) and stirring is continued for 15 minutes by Syringe with stirring for 5 minutes and added dropwise 4-methyl-1-pentanol of 3.33 ml) (foaming, gas, slight heat). The temperature does not rise above 25°C. Stirring is continued for 60 min at ambient temperature, resulting in receive light yellow suspension.

B) Then for 8 min add 6-chloro-2-methoxy-3-nitropyridine dissolved in dry dioxane (10 ml) (foam and gas). To maintain the temperature below 28°C. using a cooling bath with a mixture of ice/water. Re-added dioxane (10 ml) and the suspension stirred at ambient temperature overnight. Over the course of the reaction is monitored by examining the sample by using the1H-NMR (produced by processing a small sample as described below), which shows the presence of 30% of the original substance. For further carrying out the reaction, double-add alcohol solution of 4-methyl-1-pentanol according to the method described in paragraph (a): first add the number that represents half of the amount specified in paragraph (a), and stirring is continued for 1 hour the second time dobavlaut amount equal to 0.3 × quantity specified in paragraph (a), and stirring is continued for 2.5 hours Then add water (50 ml, pH is equal to about 10) and the mixture extracted with ether (2×80 ml). Then the combined organic phases are dried over sodium sulfate, filtered and the solvent is removed in vacuum and get 6,70 g of orange-brown oil. Purification using flash chromatography on silica gel using mixtures of hexane/ethyl acetate 98:2 (by vol.:about.) give 2.70 g of a mixture of the desired compound (15%) and 6-methoxy-2-(4-methylpentylamino)-3-nitropyridine (85%, the structure below). The mixture in this form is used for subsequent recovery of the nitro group and obtain the corresponding aniline derivatives.

6-methoxy-2-(4-methylpentylamino)-3-nitropyridine

1H NMR (400 MHz, CDCl3) of the desired compound: δ is 0.92 (d, 6H), to 1.37 (m, 2H), 1,62 (m, 1H), of 1.85 (m, 2H), 4,10 (s, 3H), 4,37 (t, 2H), 6.35mm (d, 1H), with 8.33 (d, 1H).

1H NMR (400 MHz, CDCl3) isomer: δ is 0.92 (d, 6H), to 1.37 (m, 2H), 1,62 (m, 1H), of 1.85 (m, 2H), 3,99 (s, 3H), 4,48 (t, 2H), 6,34 (d, 1H), 8,32 (d, 1H).

LC: UV detection: 220 nm; Rt=2,12 min (both components).

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection and Isom is RA = 0,35, Rfeduct = 0,33.

Example P30: Getting 2-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine and 6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine:

In odnogolosy round bottom flask with a volume of 10 ml, equipped with a fridge, 400 mg of a mixture of 2-methoxy-6-(4-methylpentylamino)-3-nitropyridine (15%) and 6-methoxy-2-(4-methylpentylamino)-3-nitropyridine (85%), suspended in methanol (1.50 ml). Under stirring and cooling in a bath of ice water added 37% aqueous hydrochloric acid solution (0,66 ml). After removal of the cooling bath add powdered tin (280 mg). Then, the resulting suspension is stirred at the boil under reflux for 3.5 hours the mixture is allowed to warm to room temperature and the methanol removed in vacuo. To the resulting dark green resinous substance is added 2 M aqueous solution of sodium hydroxide (10 ml, pH is approximately 12). The mixture is extracted with ethyl acetate (2×20 ml). The organic layer is dried over sodium sulfate, filtered and the solvent is removed in vacuum and obtain 310 mg of a yellow oil. The crude substance is purified using chromatography on silica gel (eluent: hexane/ethyl acetate, gradient mode from 1:0 to 98:2 (by vol.:vol.)). Receive 30 mg of the desired compound (8,5%) as a brown oil.

The desired connection

1The NMR (400 MHz, CDCl3): δ of 0.90 (d, 6N), to 1.31 (m, 2H), 1,60 (m, 1H), about 1.75 (m, 2H), 3,37 (broad, 2H), 3,95 (s, 3H), 4,14 (t, 2H), x 6.15 (d, 1H), 6,93 (d, 1H).

LC: UV detection: 220 nm; Rt=1,69 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,10, Rfeduct = 0,35.

In addition to the required connections are also emit 250 mg isomer, 6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine, in the form of an orange-brown oil (71%).

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6N), of 1.33 (m, 2H), 1.61 of (m, 1H), 1,79 (m, 2H), 3,38 (broad, 2H), 3,82 (s, 3H), 4,32 (t, 2H), 6,14 (d, 1H), 6,94 (d, 1H).

LC: UV detection: 220 nm; Rt=1,72 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rf=0,15.

Example P31: Obtain 3-chloro-6-methoxy-2-(4-methylpentylamino)-5-nitropyridine and 3-chloro-2-methoxy-6-(4-methylpentylamino)-5-nitropyridine:

In a three-neck round-bottom flask with a volume of 10 ml, equipped with a fridge, 2-methoxy-6-(4-methylpentylamino)-3-nitropyridine (15%) and 6-methoxy-2-(4-methylpentylamino)-3-nitropyridine (85%) (250 mg) is dissolved in dry acetonitrile (1,00 ml) and stirred at room temperature. With stirring N-chlorosuccinimide (131 mg). Re eshiwani boiling under reflux continued for 3.5 hours After cooling to room temperature, add water (5 ml, pH is approximately 6) and the mixture extracted with ether (2×10 ml). The organic layer is washed with 10% aqueous solution of sodium bisulfite (10 ml). After drying over sodium sulfate the organic layer was filtered and the solvent is removed in vacuum and receive 250 mg of yellow solid. After chromatography on silica gel (eluent: hexane/ethyl acetate 99:1 (by vol.:about.)) obtain 230 mg of a dark red oil of the following composition:

3-chloro-6-methoxy-2-(4-methylpentylamino)-5-nitropyridine 11%
3-chloro-2-methoxy-6-(4-methylpentylamino)-5-nitropyridine 84%
6-methoxy-2-(4-methylpentylamino)-3-nitropyridine 5%

1H NMR (400 MHz, CDCl3) of the desired compound: δ is 0.92 (d, 6H), of 1.36 (m, 2H), 1,62 (m, 1H), of 1.85 (m, 2H), 4,10 (s, 3H), of 4.46 (t, 2H), 8,42 (s, 1H).

1H NMR (400 MHz, CDCl3) of 3-chloro-2-methoxy-6-(4-methylpentylamino)-5-nitropyridine: δ is 0.92 (d, 6H), of 1.36 (m, 2H), 1,62 (m, 1H), of 1.85 (m, 2H), 4,08 (s, 3H), 4,47 (t, 2H), to 8.41 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/etilize is at 9:1 (by vol.:vol.); Rfthe desired compounds and 3-chloro-2-methoxy-6-(4-methylpentylamino)-5-nitropyridine = 0,43, Rfeduct = 0,35.

Example R: Obtain 5-chloro-2-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine, 5-chloro-6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine and 6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine:

In odnogolosy round bottom flask of 50 ml volume, equipped with a fridge, 220 mg of a mixture of 3-chloro-6-methoxy-2-(4-methylpentylamino)-5-nitropyridine (11%), 3-chloro-2-methoxy-6-(4-methylpentylamino)-5-nitropyridine (84%) and 6-methoxy-2-(4-methylpentylamino)-3-nitropyridine (5%), suspended in methanol (1.50 ml). Under stirring and cooling in a bath of ice water added 37% aqueous hydrochloric acid solution (0,32 ml). After removal of the cooling bath add powdered tin (181 mg). Then, the resulting suspension is stirred at the boil under reflux for 2.5 hours Over the course of the reaction is monitored by thin layer chromatography, which shows the absence of starting material. The mixture is allowed to warm to room temperature and the methanol removed in vacuo. To the resulting yellow solid substance is added 2 M aqueous sodium hydroxide solution (5 ml, pH is approximately 12). The mixture is extracted with ethyl acetate (2×10 ml). The organic layer is dried over sulfate NAT the Oia, filtered and the solvent is removed in vacuum and obtain 170 mg of a yellow oil. The crude substance is purified using chromatography on silica gel (eluent: hexane/ethyl acetate 97:3 (by vol.:vol.)). Cleaning gives 170 mg of pure 5-chloro-6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine and 20 mg of a mixture of 5-chloro-2-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine (62%) and 6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine (38%). The mixture in this form used for the reaction to obtain the corresponding derivative of amidine.

The desired compound (5-chloro-6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine):

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6H), of 1.33 (m, 2H), 1.61 of (m, 1H), 1,78 (m, 2H), 3,42 (broad, 2H), 3,91 (s, 3H), or 4.31 (t, 2H), 6,99 (s, 1H).

LC: UV detection: 220 nm; Rt=2,07 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfisomer = 0,28, Rfeduct = 0,43.

The mixture consisting of the following compounds:

5-chloro-2-methoxy-6-(4-methylpentylamino)pyridine-3-ylamine (62%)

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6H), 1.32 to (m, 2H), 1.61 of (m, 1H), 1,79 (m, 2H), 3,40 (broad, 2H), 3,93 (s, 3H), 4,27 (t, 2H), 6,98 (s, 1H).

LC: UV detection: 220 nm; Rt=2,09 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1(by vol.:vol.); Rfthe desired connection = 0,18, Rfeduct = 0,43.

6-methoxy-2-(4-methylpentylamino)pyridine-3-ylamine (38%)

1H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6H), of 1.33 (m, 2H), 1.61 of (m, 1H), 1,79 (m, 2H), 3,40 (broad, 2H), 3,82 (s, 3H), 4,32 (t, 2H), 6,14 (d, 1H), 6,94 (d, 1H).

LC: UV detection: 220 nm; Rt=1,72 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 9:1 (by vol.:vol.); Rfthe desired connection = 0,15, Rfeduct = 0,35.

Example P33: Obtain 3-nitro-2-phenylpyridine:

In odnogolosy round bottom flask of 250 ml, equipped with a fridge, 10.0 g of 2-chloro-3-nitropyridine (SA registration No. 5470-18-8) in argon atmosphere was dissolved in of 75.0 ml of toluene and 9.3 ml of ethanol. Then add MT 19 : 18 g potassium carbonate 12.0 ml of water, then of 7.69 g phenylboronic acid. The mixture is stirred in a stream of argon for 15 min, then add 2,19 g of tetrakis(triphenylphosphine)palladium. The mixture is then stirred at the boil under reflux for 20 hours Then the dark brown mixture is cooled to ambient temperature, then add 100 ml of a saturated aqueous solution of NH4Cl. This mixture is extracted with AcOEt (2×100 ml). The organic phase is dried over Na2SO4, filtered and concentrated in vacuo and p is get 15,26 g of dark brown oil. After purification of the residue via flash chromatography [cartridge with silica gel (20 g, 60 ml) and hexane/ethyl acetate 3:2 (vol.:about.)], 12,23 g get the desired compound as a brown oil.

The desired compound obtained as a brown oil.

1H NMR (400 MHz, CDCl3): δ 7,46 (m, 4H), 7,56 (m, 2H), 8,13 (dd, 1H), cent to 8.85 (dd, 1H).

LC: UV detection: 220 nm; Rt=1,54 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,44, Rfeduct = 0,44.

Example P34: Obtain 3-nitro-2-vinylpyridine-1-oxide are:

In a three-neck round bottom flask of 250 ml, equipped with a thermometer, dropping funnel and a refrigerator are 11.62 g of 3-nitro-2-phenylpyridine dissolved in 58,0 ml of dichloromethane. Then add 13,65 g of the adduct H2O2with urea. When cooled in a bath of ice water for 25 min added dropwise 16,40 ml of anhydride triperoxonane acid (temperature below 12°C). After stirring at 10°C for 45 min the cooling bath removed and the mixture was stirred at ambient temperature for 18 hours Then add 150 ml of water (pH is approximately equal to 1) and the mixture extracted with dichloromethane (3×100 ml). After washing the organic phase with 10% water is astorm sodium sulfite its dried over Na 2SO4. After purification by chromatography through a layer of silica gel (eluent: first dichloromethane, then ethyl acetate) get of 9.45 g of the desired compound as a yellow-green solid (TPL: 116-117°C).

1H NMR (400 MHz, CDCl3): δ 7,42 (m, 3H), 7,50 (m, 3H), of 7.64 (dd, 1H), and 8.50 (dd, 1H).

LC: UV detection: 220 nm; Rt=1,12 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,05, Rfeduct = 0,44.

Example R35: Obtain 6-chloro-3-nitro-2-phenylpyridine:

In a three-neck round bottom flask of 100 ml equipped with a refrigerator, of 5.00 g of 3-nitro-2-vinylpyridine-1-oxide dissolved in 25,0 ml of dry 1,2-dichloroethane. Carefully add phosphorus oxychloride (3,18 ml) (yellow-orange solution). Then this mixture is stirred at the boil under reflux for 17 hours, After cooling the mixture to ambient temperature, add a mixture of ice/water. The mixture is extracted with dichloromethane (2×50 ml). After washing with brine, the organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue via flash chromatography using a cartridge of silica gel (25 g, 150 ml) and a mixture of hexane/ethyl acetate 4:1 (by vol.:about. gives 2,61 g of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 7,46 (m, 4H), 7,56 (m, 2H), 8,10 (d, 1H).

LC: UV detection: 220 nm; Rt=1,78 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,59, Rfeduct = 0,05.

Example R36: Obtain 2-chloro-6-methyl-5-nitronicotinic:

In pathology reaction flask with a volume of 200 ml, provided with a mechanical stirrer, addition funnel, thermometer and a fridge, 10,00 g of 6-methyl-2-oxo-1,2-dihydropyridines-3-carbonitrile (CA registration number: 4241-27-4) is added slowly to 75,0 ml of concentrated sulfuric acid (heat). Under stirring and cooling in a bath of ice water for 10 minutes added dropwise acid mix (freshly prepared from 5.0 ml of concentrated sulfuric and 3.40 ml of fuming nitric acid). The mixture is first allowed to warm to 25°C and then stirred for about at this temperature (in the beginning from time to time cooling in a bath of ice water) for 4 hours the mixture is Then carefully poured into ice and then add water (total volume 250 ml). Precipitation occurs. After filtration, washing with water and drying produce 750 mg of yellow solid which is a mixture of 6-methyl-5-nitro-2-about the co-1,2-dihydropyridines-3-carbonitrile (39%) and amide 6-methyl-5-nitro-2-oxo-1,2-dihydropyridines-3-carboxylic acid (61%). This mixture is directly used in the next stage.

In odnogolosy round bottom flask of 50 ml volume, equipped with a refrigerator, a mixture obtained above are suspended in 3,80 ml of phosphorus oxychloride. This mixture while stirring and refluxed for 23,5 h (dark brown solution). After cooling the mixture to ambient temperature it was concentrated in vacuo at 50°C. the Obtained resinous substance is treated with ice, then an excess of a saturated aqueous solution of sodium bicarbonate. The mixture is extracted with AcOEt (3×20 ml). The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo and receive 600 mg of brown solid. Purification of the residue via flash chromatography using a cartridge with silica gel (20 g, 60 ml) and a mixture of hexane/ethyl acetate 9:1 (by vol.:about.) give 510 mg of the desired compound as a pale yellow solid (TPL: 94-95°C).

1H NMR (400 MHz, CDCl3): δ 2.95 for (s, 3H), at 8.60 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 1:4 (vol.:vol.); Rfthe desired connection = 0,68, Rfeduct = 0.

Example P37: Obtaining 2-(4-chloro-3-triptoreline)-6-methyl-5-nitronicotinic:

In odnogolosy rogadinae flask of 50 ml volume 990 mg of 4-chloro-3-triptoreline dissolved in 5,00 ml of dry dioxane. Then added with stirring at 1.73 ml base Hunya, then of 1.00 g of 2-chloro-6-methyl-5-nitronicotinic and stirring is continued at ambient temperature for 24 h (dark purple suspension). The mixture is then filtered through a layer of silica gel on a disk sintered glass filter and then washed with dichloromethane. The combined organic phase was concentrated in vacuo and get 2,32 g dark purple resinous substance. After purification using chromatography [cartridge with silica gel (50 g, 150 ml), eluent: hexane/ethyl acetate 4:1 (by vol.:about.)] gain of 1.53 g of the desired compound as an orange solid (TPL: 110-111°C).

1H NMR (400 MHz, CDCl3): δ 2,77 (s, 3H), 7,34 (dd, 1H), 7,60 (m, 2H), 8,72 (s, 1H).

LC: UV detection: 220 nm; Rt=2,08 minutes

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 2:1 (by vol.:vol.); Rfthe desired connection = 0,54, Rfeduct = 0,52.

Example R: Obtain 6-methyl-2-(4-methylpentylamino)-5-nitronicotinic:

In the reaction vessel Supelco volume of 8 ml to 0.95 ml of 4-methylpentan-1-ol added to 1.00 g of 2-chloro-6-methyl-5-nitronicotinic. The reaction vessel is closed by a membrane and the mixture is stirred at the boil under reflux (temperature is ur oil bath 130°C). Over the course of the reaction is monitored by thin layer chromatography. After 46 h re-add of 0.53 ml of 4-methylpentan-1-ol and stirring is continued under the same conditions. After heating in the aggregate for 118 h mixture is allowed to warm to ambient temperature. Then volatile components are removed under vacuum at a temperature of 50°C and a gain of 1.08 g of brown oil. After purification using chromatography [cartridge with silica gel (50 g, 100 ml), eluent: hexane/ethyl acetate 95:5 (vol.:about.)], 690 mg of the desired compound obtained as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,93 (d, 6N), of 1.34 (m, 2H), 1,62 (m, 1H), of 1.85 (m, 2H), 2,87 (s, 3H), to 4.52 (t, 2H), 8,59 (s, 1H).

TCX: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 2:1 (by vol.:vol.); Rfthe desired connection = 0,59, Rfeduct = 0,52.

Example R: Obtain 3-bromo-4-methyl-5-nitro-1H-pyridine-2-it:

In a three-neck round bottom flask 1000 ml of 5.00 g of 4-methyl-5-nitro-1H-pyridine-2-she (CA registration number: 21901-41-7) are suspended in 500 ml of water. The mixture with stirring, maintained at a temperature of 40°C, while added dropwise to 1.83 ml of elemental bromine. Stirring is continued at 40°C for another 4 h and Then the mixture is cooled to 10°C. and the precipitate collected fil the management and washed with water (4×). After drying receive of 6.65 g of the desired compound as a beige solid (TPL: 237-240°C).

Example R40: Obtain 3-bromo-2-chloro-4-methyl-5-nitropyridine:

In odnogolosy round bottom flask with a volume of 25 ml to 1,72 ml of phosphorus oxychloride, maintained at a temperature of 5°C, successively added 0,857 ml of quinoline and 3.40 g of 3-bromo-4-methyl-5-nitro-1H-pyridine-2-it. Received the beige suspension is stirred under heating at 120°C, resulting in a get a brown solution. Stirring is continued for 2 hours Then the solution is cooled to ambient temperature and poured into water. The precipitate is collected by filtration, the filter cake washed with water (4×) and dried, yielding 3,15 g of the desired compound as a brown solid (TPL: 60-62°C).

Example R: Obtain 3-bromo-2-(4-chloro-3-triptoreline)-4-methyl-5-nitropyridine:

In a three-neck round bottom flask of 250 ml of 4.00 g of 4-chloro-3-triptoreline dissolved in 80 ml of dry methyl ethyl ketone. Type of 3.85 g of potassium carbonate, then 4,70 g 3-bromo-2-chloro-4-methyl-5-nitropyridine. The obtained brown suspension is heated with stirring at 80°C for 3 hours Then the green suspension is allowed to warm to ambient temperature and then poured into water. A mixture of extras is Giroud with ethyl acetate (3×50 ml). The combined organic phases are washed with brine, dried over sodium sulfate, filtered and the solvent is removed in vacuum. After purification of the crude product using silica gel and a mixture of cyclohexane/ethyl acetate 19:1 (by vol.:about.) get of 7.36 g of the desired compound as a light yellow resinous substance which during curing hardens (TPL: 73-74°C).

Example R42 cable line: Obtain 2-(4-chloro-3-triptoreline)-3,4-dimethyl-5-nitropyridine:

Example P43: obtain the methyl ester of N-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-aminomorpholine acid:

In odnogolosy round bottom flask of 50 ml volume of 3.00 g of 5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-ylamine dissolved in 10 ml of triethylorthoformate. With stirring, a solution is refluxed for 8 hours and Then the reaction mixture is allowed to warm to ambient temperature and the volatiles removed in vacuum at 50°C and get to 3.38 g of the desired compound as a brown oil.

1H NMR (400 MHz, CDCl3): δ 0,91-of 0.94 (d, 6H, CH3), 1,31-of 1.41 (m, 2H, CH2), 1.56 to at 1.73 (m, 1H, CH), of 1.76 and 1.80 (m, 2H, CH2), to 2.35 (s, 3H, CH3), 4,28 (s, 3H, CH3), 4,33 is 4.36 (t, 2H, CH2), 7,26 (s, 1H), of 7.75 (s, 1H).

TLC: Plates: Merck DC-Platten, silica gel F254saturated atmosphere in the chamber to manifest the I, UV detection, eluent: cyclohexane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,73.

Example R: Obtaining N-[5-bromo-2-methyl-6-(4-methylpentylamino)-pyridine-3-yl]-N'-atinformation:

In odnogolosy round bottom flask of 50 ml volume of 540 mg of methyl ester of N-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-aminomorpholine acid dissolved in 6,60 ml of dry dichloromethane. Under stirring at ambient temperature add 214 mg etilamingidrokhlorida and 0.45 ml of base Hunga. Stirring is continued at room temperature for 20 hours and Then the volatile components are removed under vacuum at 50°C. After purification on silica gel (eluent: heptane/ethyl acetate 8:1 (by vol.:about.) with 5% triethylamine) to obtain 530 mg of the desired compound as a brown oil.

1H NMR (400 MHz, CDCl3): δ from 0.88 to 0.89 (d, 6H, CH3),1,22 of 1.28 (t, 3H, CH3) 1,30-of 1.36 (m, 2H, CH2), 1,57 by 1.68 (m, 1H, CH), 1,75-to 1.82 (m, 2H, CH2), 3,32 is 3.40 (broad, 2H, CH2) to 2.35 (s, 3H, CH3), 4,30-4,34 (t, 2H, CH2), 4,34-4,71 (broad, 1H, NH) 7,28 (s, 1H), 7,45 (s, 1H).

TCX: Plates: Merck DC-Platten, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: cyclohexane/ethyl acetate 1:1 (by vol.:about.) + 5% triethylamine; Rfthe desired connection = 0,24.

Example P45: Obtaining N'-[5-bromo-2-methyl-6-(4-methylpentylamino)-pyridine-3-yl]-N,N-diethylpara Idina:

In odnogolosy round bottom flask of 50 ml volume of 540 mg of methyl ester of N-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-aminomorpholine acid dissolved in 6,60 ml of dry dichloromethane. Under stirring at ambient temperature add 0,273 ml diethylamine. Stirring is continued at ambient temperature for 44 hours LC sample shows that in the mixture there is still 40% of the original substance. Re-add diethylamine and stirring is continued for another 24 hours and Then the volatile components are removed under vacuum at 50°C. After purification on silica gel (eluent: heptane/ethyl acetate 8:1 (by vol.:about.) with 5% triethylamine) to obtain 530 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ 0,92-0,0,94 (d, 6H, CH3), a 1.20-1.25 (t, 6H, CH3) 1,31-of 1.39 (m, 2H, CH2), 1,57-to 1.67 (m, 1H, CH), 1,74-to 1.82 (m, 2H, CH2), was 2.34 (s, 3H, CH3) 3,19-3,49 (broad, 4H, CH2), 4,28-4,34 (t, 2H, CH2), 7,30 (s, 1H), was 7.36 (s, 1H).

TLC: Plates: Merck DC-Platten, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: cyclohexane/ethyl acetate 1:1 (by vol.:vol.); Rfthe desired connection = 0,66.

Example P46: Obtain 3-bromo-5-isothiocyanato-6-methyl-2-(4-methylpentylamino)pyridine:

In odnogolosy round bottom flask of 50 ml volume 800 mg 5-bromo-2-meth is l-6-(4-methylpentylamino)pyridine-3-ylamine dissolve 1.00 ml of dry dichloromethane (light yellow solution). Under stirring at a temperature below 5°C (bath with a mixture of ice/water) first dropwise added triethylamine (46.6 ml) then thiophosgene (ClCSCl) (28,5 ml). Stirring is continued at the same temperature for 1.25 hours Then add water (10 ml) and the mixture extracted with diethyl ether (2×10 ml). After washing with brine, the organic phase is dried over sodium sulfate, filtered and concentrated in vacuo and obtain 130 mg of a yellow oil. The substance in this form is used in the next stage.

Example R: Obtain 3-[5-bromo-2-methyl-6-(4-methylpentylamino)pyridine-3-yl]-1-isopropyl-1-methylthymine:

In odnogolosy round bottom flask of 50 ml volume of 920 mg of 3-bromo-5-isothiocyanato-6-methyl-2-(4-methylpentylamino)pyridinoline dissolve 1.00 ml of dry chloroform. When the ambient temperature with stirring, added dropwise to isopropylaniline (20.4 mg). Stirring is continued at the same temperature for 45 minutes Then to the resulting orange solution was added to 5.00 ml of water. The mixture is extracted with diethyl ether (2×10 ml). After washing with brine, the organic phase is dried over sodium sulfate, filtered and concentrated in vacuo and obtain 140 mg of brown oil. Purification of the residue via flash chromatography using a cartridge with silica gel (20 g, 60 ml) and a mixture of hexane/etelaat is 95:5 (vol.:about.) gives 60,0 mg of the desired compound as a yellow oil.

1H NMR (400 MHz, CDCl3): δ to 0.92 (d, 6H), of 1.24 (d, 6H), of 1.34 (m, 2H), and 1.63 (m, 1H), 1,80 (m, 2H), 2,34 (s, 3H), is 3.08 (s, 3H), 4,34 (t, 2H), 5,48 (broad, 1H), 6,70 (broad, 1H), of 7.70 (s, 1H).

LC: UV detection: 220 nm; Rt=2,19 minutes

TLC: Plates: Merck DC-Plates, silica gel F254saturated atmosphere in the chamber for the manifestation, UV detection, eluent: heptane/ethyl acetate 4:1 (by vol.:vol.); Rfthe desired connection = 0,22, Rfeduct = 0,67.

The R48 example: Obtain 5-amino-2-imidazol-1-yl-6-methylnicotinamide:

In the reaction vessel Supelco volume of 8 ml of 200 mg of 2-chloro-6-methyl-5-nitronicotinic (140 mg) is dissolved in dry dioxane (1,00 ml). After you have added 138 mg of imidazole, the mixture was stirred at ambient temperature for 70 hours and Then the suspension is filtered through a layer of silica gel, filtered, the precipitate washed with ethyl acetate and the combined organic phase was concentrated in vacuo and receive 240 mg orange-brown solid. In odnogolosy round bottom flask of 50 ml volume of this solid (240 mg) was dissolved in methanol (1,00 ml). Under stirring and cooling in a bath of ice water are added dropwise 1.00 mol 27% aqueous solution of hydrochloric acid. After removal of the cooling bath add powdered tin (186 mg). Gray-green suspension was stirred at boiling with britishtelecom for at 2.45 PM Then the heating bath is removed and the mixture stirred at ambient temperature overnight. Then the volatile components removed in vacuo and add 20 ml of 4 M aqueous solution of sodium hydroxide. The mixture is extracted with ethyl acetate (3×15 ml). The organic layer is dried over sodium sulfate, filtered and the solvent is removed in vacuum and receive 160 mg orange-brown solid.

MS: ER+ (elektrorazpredelenie): 200 (M+N)+; ER-: 198 (M-N)+

Use the following methods for LC

Method 1

The HP1100 HPLC firm Agilent: device degassing of the solvent, quadratic pump, thermostatted block column and detector diode matrix.

Column: Phenomenex Gemini C18, particle size 3 μm, 110 Angstrom, 30×3 mm,

temperature: 60°C

DDM (detector diode matrix) wavelength range (nm): 200 to 500

Gradient mode of solvent: (the same for all methods)

A = water + 0.05% HCOOH

B = acetonitrile/methanol (4:1, vol/about.) + 0.04% HCOOH

TimeAnd%In%Flow rate (ml/min)
0,0095,05,01,700
2,00 0,0100,01,700
2,800,0100,01,700
2,9095,05,01,700
3,1095,05,01,700

Method 3

The HP1100 HPLC firm Agilent: device degassing of the solvent, tandem pump, thermostatted block column and detector diode matrix.

Column: Phenomenex Gemini C18, particle size 3 μm, 110 Angstrom, 30×3 mm, temp: 60°C, DDM range of wavelengths (nm): 200 to 500.

Gradient mode of solvent: (same as above).

Method 4

The HP1100 HPLC firm Agilent: device degassing of the solvent, tandem pump, thermostatted block column and the detector wavelength.

Column: Phenomenex Gemini C18, particle size 3 μm, 110 Angstrom, 30×3 mm, temp: 60°C.

Gradient mode of solvent: (same as above).

MS. Spectra shoot at the ZMD spectrometer (Micromass, Manchester UK) or ZQ spectrometer (Waters Corp. Milford, MA, USA)equipped with a source of electrocapillary (EEC); the source temperature 80 to 100°C; temperature desolvatation from 200 to 250 is C; the voltage on the cone 30 In; gas velocity on the cone 50 l/h, the speed desolvatation gas at 400 to 600 l/h, mass range: 150 to 1000 Da).

The compounds listed in the following tables, can be obtained similarly. The following examples are intended to illustrate the present invention and are the preferred compounds of formula I and X.

Table R:
The physical characteristics of the compounds of formula I and X:
Connection # PatternsMS/NMR/melting point in °C
R1H NMR (400 MHz, CDCl3): δ 1.18 to to 1.23 (t, 3H, CH3), 2,98 (s, 3H, CH3), 3,25-3,51 (mbr, 2H, CH2), at 6.84-6.89 in (d, 1H), to 7.09 (d, 1H), 7.23 percent (d×d, 1H), 7,35 (d×d, 1H), 7,45 (d, 1H), 7.50 for (sbr, 1H), of 7.75 (d, 1H),
R1H NMR (400 MHz, CDCl3): δ 1,38+1,48 (2d, 3H, CH3), of 2.20 (s, 3H, CH3), 2,30+2,40 (2d, 1H, CH), 2,89+2,98 (2s, 3H, CH3), 4,43+5,38 (2m, 1H, CH), 6,72 (s, 1H), 7,15 (d×d, 1H), 7,38 (d, 1H), 7,42 (d, 1H), 7.62mm (s, 1H), 7,98+8,15 (2s, 1H),
R 1H NMR (500 MHz, CD3CN): δ 2,92 (s, 3H, CH3), of 2.97 (s, 3H, CH3), to 6.88 (d, 1H), 7,13 (d, 1H), 7,32 (d×d, 1H), was 7.36 (d×d, 1H), 7,55 (d, 1H), 7,60 (s, 1H), 7,63 (d, 1H),
Rresin
R1H NMR (400 MHz, CDCl3): δ 1,11-1,17 (2q, M, 4×CH3), 3,20 (s, 6N, 2×CH3), is 3.08-3,20 (m, 2H), between 6.08 (s, 1H), 6,85 (d×d, 1H), 7,14 (s, 1H), 7,28 (d, 1H), 7,37 (d, 1H),
Rresin
Rresin
Rresin

Connection # PatternsMS/NMR/melting point in °C
Rresin
R.10 resin
P.111H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), is 2.30 (s, 3H, CH3), to 3.00 (s, 3H, CH3), 3,28-of 3.53 (m, 2H, CH3), 6,78 (s, 1H), 7,19 (d×d, 1H), 7,39 was 7.45 (m, 3H), 7,54 (s, 1H),
P.12resin
P.131H NMR (400 MHz, CDCl3): δ 1,95 (mbr, 4H, 2×CH2), of 2.28 (s, 3H, CH3), 3,50-3,55 (m, 4H, 2×CH2), 7,17 (d×d, 1H), 7.23 percent (d, 1H), 7,39 (d, 1H), 7,55 (d, 1H), to 7.64 (d, 1H), of 7.75 (s, 1H),
P.14resin
P.15resin
P.161H NMR (400 MHz, CDCl3): δ 2,34 (t, 3, CH3), 3,53 (s, 3H, CH3), of 6.96 (d, 1H), 7.00 the (d×d, 1H), 7,21 (d×d, 1H), 7,38 (d, 1H), 7,45-7,51 (m, 2H), 7.68 per-7,72 (m, 1H), 7,79 (d, 1H), 8,33 (d×d, 1H), 9,11 (s, 1H),

Connection # PatternsMS/NMR/melting point in °C
R.171H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), of 1.30 (s, N, 3×CH3), of 2.28 (s, 3H, CH3), to 3.00 (s, 3H, CH3), of 3.25 to 3.35 (mbr, 2H, CH2), to 6.80 (d×d, 1H), 7,08 for 7.12 (m, 2H), 7,20-7,27 (m, 2H), 7,53 (sbr, 1H), to 7.67 (d, 1H),
R.18resin
R1H NMR (400 MHz, CDCl3): δ 1,19-of 1.24 (t, 3, CH3), of 2.28 (s, 3H, CH3), to 3.00 (s, 3H, CH3), 3,28-of 3.53 (m, 2H, CH3), 7,15-7,26 (m, 2H), 7,40 (d, 1H), 7,46 (d, 1H), 7,55 (sbr, 1H), 7,65 (d, 1H),
R.201H NMR (500 MHz, CD3CN): δ equal to 2.94 (s, 3H, CH3), 2,98 (s, 3H, CH3), of 6.90 (d, 1H), 7,30 (m, 1H), was 7.36-7,40 (2m, 2H), 7,46 (m, 1H), 7,54 (m, 1H), 7.62mm (s, 1H), 7,72 (d, 1H),
R.211H NMR (500 MHz, CD3CN): δ 2,92 (s, 3H, CH3), of 2.97 (s, 3H, CH3in ), 3.75 (s, 3H, OCH3), to 6.75 (d, 1H), 6,91 (d, 2H), 6,98 (d, 2H), 7,30 (d×d, 1H), 7,58 (s, 1H), 7,65 (d, 1H),
R.221H NMR (500 MHz, CD3CN): δ 2,90 (s, 3H, CH3), of 2.97 (s, 3H, CH3), at 6.84 (d, 1H), 7,02 (d, 2H), 7,34 (d, 2H), 7,35 (d×d, 1H), 7,60 (s, 1H), of 7.70 (d, 1H),
R.231H NMR (500 MHz, CD3CN): δ 2,90 (s, 3H, CH3), of 2.97 (s, 3H, CH3), 6.87 in (d, 1H), 7,15-7.23 percent (2m, 4H), 7,35 (d×d, 1H), 7,58 (s, 1H), 7,81 (d, 1H),
R.241H NMR (500 MHz, CD3CN): δ 2,90 (s, 3H, CH3), 2,96 (s, 3H, CH3), 6,93 (d, 1H), 7,21 (t, 1H), 7,38 (d×d, 1H), 7,45 (d, 2H), 7,54 (d, 1H), 7,58 (s, 1H),
R1H NMR (500 MHz, CD3CN): δ of 2.45 (s, 3H, SCH3), of 2.92 (s, 3H, CH3), of 2.97 (s, 3H, CH3), PC 6.82 (d, 1H), 7,02 (d, 2H), 7,28 (d, 2H), 7,35 (d×d, 1H), 7,60 (s, 1H), of 7.70 (d, 1H),

Connection # PatternsMS/NMR/melting point in °C
R.261H NMR (400 MHz, CDCl3): δ of 0.91 (d, 6N), 1,15-of 1.40 (m, m, 5H), to 1.61 (m, 1H), 1,78 (m, 2H), of 2.38 (s, 3H), 3.04 from (broad, 3H), 3.25 to of 3.60 (broad, 2H), 4,30 (t,2H), 7,28 (s, 1H), 7,30-7-50 (broad, 1H),
R.271H NMR (400 MHz, CDCl3): δ 0,88 (d, 6N); of 1.20 (t, 3H), of 1.23 (m, 2H), 1,58 (m, 1H), 1,72 (m, 2H), 2,44 (s, 3H), to 3.02 (s, 3H), 3,15-of 3.60 (broad, 2H), 4,29 (t, 2H), 7,06 (s, 1H), 7,34 (d, 2H), 7,42 (broad, 1H), 7,52 (d, 2H),
R1H NMR (400 MHz, CDCl3): δ of 0.90 (d, 6N), of 1.20 (t, 3H), of 1.33 (m, 2H), 1,60 (m, 1H); to 1.76 (m, 2H), 2,41 (s, 3H), 2,99 (s, 3H), 3,20-3,50 (broad, 1H), 3,35 (broad, 1H), 4,18 (t, 2H), 6,46 (d, 1H), 7,01 (d, 1H), 7,38 (broad, 1H),
R.291H NMR (400 MHz, CDCl3): δ 1,15-1,35 (broad, 3H), of 2.34 (s, 3H), 3,03 (s, 3H), 3.25 to of 3.60 (broad, 2H), 7,16 and 7,19 (dd, 1H), 7,35 (s, 1H), 7,42 (m, 1H), 7,45 (m, 1H), 7,30-of 7.55 (broad, 1H),
RRP HPLC: retention Time of compound: 1,55 min
R.31RP HPLC: retention time of compound: 1,61 min
RRP HPLC: retention time is soedineniya: 1.46 and 1,49 min
R.33RP HPLC: retention time of compound: 1,44 min
R.34RP HPLC: retention time of compound: 1,38 min

Connection # PatternsMS/NMR/melting point in °C
R.35RP HPLC: retention time of compound: 2,19 min
R.36RP HPLC: retention time of compound: 1,11 min
R78-79°C. the intermediate product (formula X)
RRP HPLC: retention time of compound: min 1,35
R.3993-94°C
R.40155-156°C
R142-143°C
R92-93°C
R66-67°C
R91-92°C. the intermediate product (formula X)

Connection # PatternsMS/NMR/melting point in °C
RRP HPLC: retention time of compound: 1,27 min
RRP HPLC: retention time of compound: 1,42 min
RRP HPLC: retention time of compound: 1,45 min
RRP HPLC: retention time of compound: 1,50 min
R72-73°C
R82-83°C
5170-71°C
R81-82°C
RRP HPLC: retention time of compound: 1,43 min
RRP HPLC: retention time of compound: 1,51 min
RRP HPLC: retention time of compound: 2,31 min

Connection # PatternsMS/NMR/temp the temperature of the melting point in °C
RRP HPLC: retention time of compound: 2,27 min
R74-75°C
RRP HPLC: retention time of compound: 1,31 min
RRP HPLC: retention time of compound: 1,40 min
RMS (M+1) 296 intermediate product (formula X)
RRP HPLC: retention time of compound: 1,42 min
RRP HPLC: retention time of compound: 1,36 min
R80-82°C
R RP HPLC: retention time of compound: 1,65 min
RRP HPLC: retention time of compound: 1,41 min

Connection # PatternsMS/NMR/melting point in °C
RRP HPLC: retention time of compound: 1,45 min
RRP HPLC: retention time of compound: 1,20 min
R84-85°C
RRP HPLC: retention time of compound: 1,72 min
RRP HPLC: retention time of compound: 1,32 min
R RP HPLC: retention time of compound: 1,60 min
RRP HPLC: retention time of compound: 1,61 min
RRP HPLC: retention time of compound: 1,33 min
RRP HPLC: retention time of compound: 2,24 min

Connection # PatternsMS/NMR/melting point in °C
RRP HPLC: retention time of compound: 2,10 min
RRP HPLC: retention time of compound: min 1,35
RRP HPLC: retention time of compound: 1,37 min
R/td> 123-125°C
RRP HPLC: retention time of compound: 1,46 min
RRP HPLC: retention time of compound: 1,50 min
RRP HPLC: retention time of compound: 2,22 min
RRP HPLC: retention time of compound: 1,39 min

In table 526 And the sets of values of the variables R1, R2, R5and R6in the compound of formula I.

N
Table a:
Values of R1, R2, R5and R6:
StringR1R2R6R5
A.1.1CH3CH2CH3
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.7CH3CH2CH3N
.1.8 CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
A.1.10CH3CH2CH3N
A.1.11CH3CH2CH3N
A.1.12CH3CH2CH3N
A.1.13CH3 CH2CH3N
A.1.14CH3CH2CH3N
A.1.15CH3CH2CH3N
A.1.16CH3CH2CH3N
A.1.17CH3CH2CH3N

StringR1R2R6R5
A.1.18CH3CH2CH3N
A.1.19CH3CH2CH3N
A.1.20CH3CH2CH3N
A.1.21CH3CH2CH3N
A.1.22CH3CH2CH3N
A.1.23CH3CH2CH3N
A.1.24CH3CH2CH3N
A.1.25 CH3CH2CH3N
A.1.26CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.30CH3CH2CH3 N
A.1.31CH3CH2CH3N
A.1.32CH3CH2CH3N
A.1.33CH3CH2CH3N
A.1.34CH3CH2CH3N
A.1.35CH3CH2CH3N

StringR1R2R6 R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3 CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.50CH3CH2CH3N

StringR1R2R6R5
A.1.51CH3CH2CH3N
A.1.52CH3CH2CH3N
A.1.53CH3CH2CH3N
A.1.54CH3CH2CH3N
A.1.55CH3CH2CH3N
A.1.56CH3CH2CH3N
A.1.57CH3CH2CH3N

StringR1R2R6R5
ACH3 CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.63CH3CH2CH3N
A.1.64CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.68CH3CH2CH3N
ACH3CH2CH3N
A.1.70 CH3CH2CH3N
A.1.71CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3/td> N
ACH3CH2CH3N
A.1.77CH3CH2CH3N
A.1.78CH3CH2CH3N

StringR1R2R6R5
A.1.79CH3CH2CH3N
A.1.80CH3CH2CH3N
A.1.81CH3CH2CH3N
A.1.82CH3CH2CH3N
A.1.83CH3CH2CH3N
A.1.84CH3CH2CH3N
A.1.85CH3CH2CH3N
A.1.86CH3CH2CH3N
A.1.87CH3 CH2CH3N

StringR1R2R6R5
A.1.88CH3CH2CH3N
A.1.89CH3CH2CH3N
A.1.90CH3CH2CH3N
A.1.91CH3CH2CH3N
A.1.92CH3CH2CH3N
A.1.93CH3CH2CH3N
A.1.94CH3CH2CH3N
A.1.95CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.100CH3CH2CH3N
A.1.101CH3CH2CH3N
A.1.102CH3CH2CH3N

StringR1R2R6R5
A.1.103CH3 CH2CH3N
A.1.104CH3CH2CH3N
A.1.105CH3CH2CH3N
A.1.106CH3CH2CH3N
A.1.107CH3CH2CH3N
A.1.108CH3CH2CH3N

StringR1R2 R6R5
A.1.109CH3CH2CH3N
A.1.110CH3CH2CH3N
A.1.111CH3CH2CH3N
A.1.112CH3CH2CH3N
A.1.113CH3CH2CH3N

StringR1R2R6R5
A.1.114CH3CH2CH3N
A.1.115CH3CH2CH3N
A.1.116CH3CH2CH3N
A.1.117CH3CH2CH3N
A.1.118CH3CH2CH3N

StringR1R2R6R5
A.1.119CH3 CH2CH3N
A.1.120CH3CH2CH3N
A.1.121CH3CH2CH3N
A.1.122CH3CH2CH3N
A.1.123CH3CH2CH3N
A.1.124CH3CH2CH3N

StringR1R2 R6R5
A.1.125CH3CH2CH3N
A.1.126CH3CH2CH3N
A.1.127CH3CH2CH3N
A.1.128CH3CH2CH3N
A.1.129CH3CH2CH3N
A.1.130CH3CH2CH3N

StringR1R2R6R5
A.1.131CH3CH2CH3N
A.1.132CH3CH2CH3N
A.1.133CH3CH2CH3N
A.1.134CH3CH2CH3N
A.1.135CH3CH2CH3N
A.1.136CH3CH2SN 3N

StringR1R2R6R5
A.1.137CH3CH2CH3N
A.1.138CH3CH2CH3N
A.1.139CH3CH2CH3N
A.1.140CH3CH2CH3N
A.1.141CH3CH2CH3N
A.1.142CH3CH2CH3N
A.1.143CH3CH2CH3N

StringR1R2R6R5
A.1.144CH3CH2CH3N
A.1.145CH3CH2CH3N
A.1.146CH3CH2CH3N
A.1.147CH3CH2CH3N
A.1.148CH3CH2CH3N
A.1.149CH3CH2CH3N
A.1.150CH3CH2CH3N
A.1.151CH3CH2CH3N

StringR1R2R6R5
A.1.152CH3 CH2CH3N
A.1.153CH3CH2CH3N
A.1.154CH3CH2CH3N
A.1.155CH3CH2CH3N
A.1.156CH3CH2CH3N
A.1.157CH3CH2CH3N
A.1.158CH3CH2CH3N

StringR1R2R6R5
A.1.159CH3CH2CH3N
A.1.160CH3CH2CH3N
A.1.161CH3CH2CH3N
A.1.162CH3CH2CH3N
A.1.163CH3CH2CH3N
A.1.164CH2CH3N
A.1.165CH3CH2CH3N
A.1.166CH3CH2CH3N

StringR1R2R6R5
A.1.167CH3CH2CH3N
A.1.168CH3CH2CH3N
A.1.169CH3CH2CH3 N
A.1.170CH3CH2CH3N
A.1.171CH3CH2CH3N
A.1.172CH3CH2CH3N
A.1.173CH3CH2CH3N

StringR1R2R6R5
A.1.174CH3CH2CH3N
A.1.175CH3CH2CH3N
A.1.176CH3CH2CH3N
A.1.177CH3CH2CH3N
A.1.178CH3CH2CH3N
A.1.179CH3CH2CH3N

StringR1R2R6R5
A.1.180CH2CH3N
A.1.181CH3CH2CH3N
A.1.182CH3CH2CH3N
A.1.183CH3CH2CH3N
A.1.184CH3CH2CH3N
A.1.185CH3CH2CH3N
A.1.186CH3CH2CH3N/td>

StringR1R2R6R5
A.1.187CH3CH2CH3N
A.1.188CH3CH2CH3N
A.1.189CH3CH2CH3N
A.1.190CH3CH2CH3N
A.1.191CH3CH2CH3N
A.1.192CH3CH2CH3N
A.1.193CH3CH2CH3N
A.1.194CH3CH2CH3N

StringR1R2R6R5
A.1.195CH3CH2CH3N
A.1.196CH3CH2CH3N
A.1.197CH2CH3N
A.1.198CH3CH2CH3N
A.1.199CH3CH2CH3N
A.1.200CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3 N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3 CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2 R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2The h 3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A CH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3 N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

The article is an eye R1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.276CH3CH2CH3N
A.1.277CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A CH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3 N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.306CH3CH2CH3N
A.1.307CH3CH2CH3N

StringR1R2R6R5
A.1.308CH3CH2CH3N
A.1.309CH3CH2CH3N
A.1.310CH3CH2CH3N
A.1.311 CH3CH2CH3N
A.1.312CH3CH2CH3N
A.1.313CH3CH2CH3N
A.1.314CH3CH2CH3N
A.1.315CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3 N
ACH3CH2CH3N
A.1.318CH3CH2CH3N
A.1.319CH3CH2CH3N
A.1.320CH3CH2CH3N
A.1.321CH3CH2CH3N
A.1.322CH3CH2CH3N
A.1.323CH3CH2CH3N
A.1.324CH3CH2CH3N
A.1.325CH3CH2CH3N
A.1.326CH3CH2CH3N
A.1.327CH3CH2CH3N

StringR1R2R6R5
A CH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3
ACH3CH2CH3N
ACH3CH2CH3N
A.1.337CH3CH2CH3N
ACH3CH2CH3N
A.1.339CH3CH2CH3N

StringR1R2R6R5
A.1.340CH3CH2CH3N
A.1.341CH3CH2CH3N
A.1.342CH3CH2CH3N
A.1.343CH3CH2CH3N
A.1.344CH3CH2CH3N
A.1.345CH3CH2CH3N
A.1.346CH3 CH2CH3N
A.1.347CH3CH2CH3N
A.1.348CH3CH2CH3N
A.1.349CH3CH2CH3N
A.1.350CH3CH2CH3N
A.1.351CH3CH2CH3N
A.1.352CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A CH3CH2CH3N
A.1.359CH3CH2CH3N
ACH3CH2CH3N
A.1.361CH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
A.1.363CH3CH2CH3 N
A.1.364CH3CH2CH3N
A.1.365CH3CH2CH3N
A.1.366CH3CH2CH3N
A.1.367CH3CH2CH3N
A.1.368CH3CH2CH3N
A.1.369CH3CH2CH3N
A.1.370CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
A.1.372CH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A CH3CH2CH3N
A.1.376CH3CH2CH3N
A.1.377CH3CH2CH3N
A.1.378CH3CH2CH3N
A.1.379CH3CH2CH3N
A.1.380CH3CH2CH3N
A.1.381CH3CH2CH3N/td>

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.391CH3CH2CH3N

StringR1R2R6R5
A CH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
A.1.398CH3CH2CH3
A.1.399CH3CH2CH3N
A.1.400CH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

is the Troc R1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3 CH2CH3N
ACH3CH2CH3N

StringR1R2R6R5
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N
ACH3CH2CH3N

Table a:
Values of R1, R2, R5and R6(continued):
StringR5
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A
A

StringR5
A
A
A
A
A
A
A
A

StringR5
A
A
A
A
A.1.500
A.1.501
A.1.502
A.1.503

StringR5
A.1.504
A.1.505
A.1.506
A.1.507
A.1.508
A.1.509
A.1.510
A.1.511

StringR5
A.1.512
A.1.513
A.1.514
A.1.515
A.1.516
A.1.517
A.1.518

StringR5
A
A.1.520
A.1.521
A.1.522
A.1.523
A.1.524
A.1.525
A.1.526

The following tables T1-T described the preferred compounds of formula I.

Table 1: this table describes 526 connections T-T1.1.526 formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A. for Example, a particular connection T is a compound of formula T1, in which each of the variables R1, R2, R5and R6in which each variable has a specific value specified in the string A table:

On the same system and all other 511 specific compounds described in table 1, as well as all of the specific compounds listed the tables 2 - T described in the same way.

Table 2: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 3: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 4: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 5: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has a specific value is eat, specified in the corresponding row, respectively, selected from 526 lines A.1.1-A table A.

Table 6: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 7: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 8: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 9: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1 , R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 10: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 11: this table describes 526 connections T-T11.1.526 formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 12: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 13: this table describes 526 connections T-T formula

,

in which to to the each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 14: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 15: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 16: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 17: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 18: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 19: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 20: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 21: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 22: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 23: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 24: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 25: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 26: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 27: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 28: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 29: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 30: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 31: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 32: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 33: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 34: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 35: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 36: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 37: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 38: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 39: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 40: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 41: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 42: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 43: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 44: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 45: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 46: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 47: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 48: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 49: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 50: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 51: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 52: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 53: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 54: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 55: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 56: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 57: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 58: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 59: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 60: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 61: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 62: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 63: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 64: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 65: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 66: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 67: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 68: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 69: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 70: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 71: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 72: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 73: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 74: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 75: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 76: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 77: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 78: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 79: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 80: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 81: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 82: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 83: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 84: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 85: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 86: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 87: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 88: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 89: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 90: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 91: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 92: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 93: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 94: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 95: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 96: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 97: this table describes 526 connections T-T formula

,

where is La of each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 98: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 99: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 100: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 101: this table describes 526 connections T-T formula

,

in which the Oy for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 102: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 103: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 104: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 105: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 106: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 107: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 108: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 109: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 110: this table describes 526 connections T-T110.1.526 formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 111: this table describes 526 connections T111.1.1-T111.1.526 formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 112: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 113: this table describes 526 connections T-T formula

,

in the cat the swarm for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 114: this table describes 526 connections T-T114.1.526 formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 115: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 116: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 117: this table describes 526 connections T-T formula

,

in to the ora for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 118: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 119: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 120: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 121: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 122: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 123: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 124: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 125: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 126: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 127: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 128: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 129: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 130: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 131: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 132: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 133: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 134: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 135: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 136: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 137: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 138: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 139: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 140: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 141: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 142: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 143: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 144: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 145: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 146: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 147: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 148: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 149: this table describes 526 connections T-T formula

,

in to the Torah for each of these specific 526 connections each of the variables R 1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 150: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Table 151: this table describes 526 connections T-T formula

,

in which for each of these specific 526 connections each of the variables R1, R2, R5and R6has specific meaning given in the corresponding line, respectively, selected from 526 lines A.1.1-A table A.

Examples of preparations of compounds of the formula I:

Examples F-1.1 F-1.3: Mulgirigala concentrates

ComponentsF-1.1F-1.2F-1.3
The connection table 1-15125%40%50%
Dodecylbenzyl ulpanat calcium 5%8%6%
Polietilenglikolya simple ether of castor oil (36 moles ethyleneoxide links)5%--
Simple ether tributylphosphorotrithioate (30 moles ethyleneoxide links)-12%4%
Cyclohexanone-15%20%
A mixture of xylenes65%25%20%

From these concentrates by dilution with water it is possible to obtain emulsions of any required concentration.

Example F-2: Emulgirujushchie concentrate

ComponentsF-2
The connection table 1-15110%
Octylphenoxypolyethoxyethanol ether (4-5 moles ethyleneoxide links)3%
Dodecylbenzensulfonate feces is tion 3%
Polyglycidyl ether of castor oil (36 moles ethyleneoxide links)4%
Cyclohexanone30%
A mixture of xylenes50%

From this concentrate by dilution with water it is possible to obtain emulsions of any required concentration.

Examples F-3.1 F-3.4: Solutions

ComponentsF-3.1F-3.2F-3.3F-3.4
The connection table 1-15180%10%5%95%
Onomatology ether of ethylene glycol20%---
Polyethylene glycol with molecular weight 400--70%-
N-Methylpyrrole-2-he- 20%--
Epoxydecane coconut oil--1%5%
Petroleum ether (evaporating temperature range: 160-190°C)--94%-

These solutions are suitable for application in the form of microdroplets.

Examples F-4.1 through F-4.4: Granules

-
ComponentsF-4.1F-4.2F-4.3F-4.4
The connection table 1-1515%10%8%21%
Kaolin94%-79%54%
Highly dispersed silicon dioxide1%-13%7%
Attapulgite90%-18%

A new connection is dissolved in dichloromethane, the solution is spray on a carrier and then the solvent is removed by distillation in vacuum.

Examples F-5.1 F-5.2: Dusty

ComponentsF-5.1F-5.2
The connection table 1-1512%5%
Highly dispersed silicon dioxide1%5%
Talc97%-
Kaolin-90%

Ready-to-use dusty receive a thorough mixing of all components.

Examples F-6.1 F-6.3: Wettable powders

Sodium lignosulphonate
ComponentsF-6.1F-6.2F-6.3
The connection table 1-15125%50%75%
5%5%-
Sodium lauryl sulfate3%-5%
Diisobutyldimethoxysilane sodium-6%10%
Penopolietilenovy ether (7-8 moles ethyleneoxide links)-2%-
Highly dispersed silicic acid5%10%10%
Kaolin62%27%-

All the components are mixed and the mixture is thoroughly ground in a suitable mill and get wettable powders which can be diluted with water to obtain suspensions of the desired concentration.

Example F7: Flowable concentrate for seed treatment

The connection table 1-15140%
Propylenglycol the ü 5%
The copolymer butanol/EA*2%
Tridirectional with 10-20 moles EO2%
1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution)0,5%
Calcium salt of monoazetta5%
Silicone oil (in the form of a 75% emulsion in water)0,2%
Water45,3%
* Propylene oxide/ethylene oxide

The finely ground active ingredient is thoroughly mixed with auxiliary substances and get a suspension concentrate from which by dilution with water can be obtained suspension of any necessary dilution. With such dilute systems of living plants, as well as material for reproduction of plants you can handle and protect from infection by microorganisms by spraying, watering or dipping.

The activity of the compositions proposed in the present invention, it is possible to significantly expand and to change in accordance with prevailing conditions by adding other insecticide, acaricide and/or fungal the active ingredients. A mixture of compounds of the formula I with other insecticide, acaricide and/or fungicide active ingredients may also have additional unexpected benefits in a broad sense can be described as synergistic activity. For example, they may be better tolerated by plants, reduced phytotoxicity, the fact that insects can be destroyed at different stages of development, or they will have the best characteristics during cooking, for example, during the grinding or mixing, during storage or during their application.

Suitable additives to the proposed in the present invention the active ingredients are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, NITROPHENOL derivatives, thiourea, juvenile hormones, formamidine, benzophenone derivatives, urea, derivatives of pyrrole, carbamates, pyrethroids, chlorinated hydrocarbons, allodapini, derivatives of pyridylmethylamine, macrolides, neonicotinoids and preparations of Bacillus thuringiensis.

Preferred are mixtures of compounds of formula I with active ingredients (the abbreviation "TX" means "one compound selected from the group comprising compounds listed in table R, and the connection vpisivaushiesya formulas T1-T, is shown in table 1-151, in the present invention"):

auxiliary substance selected from the group of substances, including mineral oils (alternative name) (628) + TX,

acaricide selected from the group of substances comprising 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (name according to IUPAC nomenclature) (910) + TX, 2,4-dichlorobenzenesulfonic (name according to nomenclature IUPAC/Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (name according to IUPAC nomenclature) (1295) + TX, 4-chlorophenylsulfonyl (name according to IUPAC nomenclature) (981) + TX, abamectin (1) + TX, achiezer (3) + TX, acetarsol [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidation (870) + TX, midflame [CCN] + TX, amidation (872) + TX, Amiton (875) + TX, amitorization (875) + TX, amitraz (24) + TX, aramid (881) + TX, arsenic trioxide (882) + TX, AVI 382 (connecting code) + TX, AZ 60541 (connecting code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (name according to IUPAC nomenclature) (888) + TX, azocyclotin (46) + TX, attout (889) + TX, benomyl (62) + TX, booksafe (alternative name) [CCN] + TX, benoxinate (71) + TX, benzyl benzoate (name according to IUPAC nomenclature) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brianalexat (alternative name) + TX, bromocyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99 + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylparaben (alternative name) + TX, calcium polysulfide (name according to IUPAC nomenclature) (111) + TX, camphechlor (941) + TX, carbanilate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothion (947) + TX, CGA 50'439 (research code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, Chlordimeform (964) + TX, chlorodimethylsilane (964) + TX, chlorfenapyr (130) + TX, florfenicol (968) + TX, chlorfenson (970) + TX, chlorfenson (971) + TX, Chlorfenvinphos (131) + TX, Chlorobenzilate (975) + TX, chlorophorm (977) + TX, chlormethine (978) + TX, chlorpropyl (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX cinerin I (696) + TX, cinerin II (696) + TX, zanarini (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, kurane (1013) + TX, zantout (1020) + TX, titlemotion (CAS Reg. No.: 400882-07-7) + TX, cigalotrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, declivous (alter the provide name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dynactin (alternative name) (653) + TX, Dinex (1089) + TX, Dinex-diclectin (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, directon (1090) + TX dinobuton (1092) + TX, dinolfo (1097) + TX, dinoterb (1098) + TX, dioxathion (1102) + TX, diphenylsulfone (name according to IUPAC nomenclature) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dienen (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, etoac-methyl (1134) + TX, etoxazole (320) + TX, etrimfos (1142) + TX, pensator (1147) + TX, fenazaquin (328) + TX, pinbalance (330) + TX, fanatical (337) + TX, fenpropathrin (342) + TX, feneral (alternative name) + TX, fenpyroximate (345) + TX, Fenton (1157) + TX, pentaphenyl (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, flociprin (360) + TX, fluazuron (1166) + TX, flibanserin (1167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluential (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fermented (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (scientific research code) (1185) + TX, formetanate (405) + TX, formmanager.load (405) + TX, formation (1192) + TX, formparent (1193) + TX, gamma-HCH (430) + TX, gliadin (1205) + TX, the Gulf is Prox (424) + TX, heptenophos (432) + TX, hexadecyltrichlorosilane (name according to nomenclature IUPAC/Chemical Abstracts) (1216) + TX, hexythiazox (441) + TX, logmean (name according to IUPAC nomenclature) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl O-(methoxyaminomethyl)salicylate (name according to IUPAC nomenclature) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, idents (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, Malathion (492) + TX, malaanonan (1254) + TX, mecarbam (502) + TX, mephosfolan (1261) + TX, mesolift (alternative name) [CCN] + TX, methacrifos (1266) + TX, metamidophos (527) + TX, mitigation (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin (alternative name) [CCN] + TX, metafox (1293) + TX, monocrotophos (561) + TX, porpotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (connecting code) + TX, NC-512 (connecting code) + TX, diflouride (1309) + TX, nikkomycin (alternative name) [CCN] + TX, nitrilases (1313) + TX, complex nitrilases:zinc chloride composition 1:1 (1313) + TX, NNI-0101 (connecting code) + TX, NNI-0250 (connecting code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxidation (1324) + TX, oxydisulfoton (1325) + TX, PP'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, mineral oil (al the alternative name) (628) + TX, phenkapton (1330) + TX, pentat (631) + TX, Fort (636) + TX, fosalan (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterphenyl (traditional name) (1347) + TX, polydactyly (alternative name) (653) + TX, prolinol (1350) + TX, profenofos (662) + TX bromacil (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protection (1360) + TX, procoat (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, predatation (701) + TX, pyrimidifen (706) + TX, perimeter (1370) + TX, finalpos (711) + TX histiotus (1381) + TX, R-1492 (research code) (1382) + TX, RA-17 (research code) (1383) + TX, rotenone (722) + TX, Srdan (1389) + TX, sabots (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (connecting code) + TX, sofabed (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (research code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (research code) (757) + TX, Tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TERR (1417) + TX, terban (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetractys (alternative name) (653) + TX, tetrasul (1425) + TX, titanox (alternative name) + TX, dicarboxyl (1431) + TX, thiofanox is (800) + TX, thiometon (801) + TX, teachings (1436) + TX, thuringensis (alternative name) [CCN] + TX, triamides (1441) + TX, triuralin (1443) + TX, triazophos (820) + TX, treasure (alternative name) + TX, trichlorfon (824) + TX, tritanopes (1455) + TX, tinactin (alternative name) (653) + TX, vamidothion (847) + TX, unilibro [CCN] and YI-5302 (a link code) + TX,

algicide selected from the group of substances comprising blocksin [CCN] + TX, dioctanoyl copper (name according to IUPAC nomenclature) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, Dylan (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, hinkleman (714) + TX, heroname (1379) + TX, Simazine (730) + TX, triphenylborane (name according to IUPAC nomenclature) (347) and triphenylborane (name according to IUPAC nomenclature) (347) + TX,

the anthelmintic selected from the group of substances containing abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, amaneciendo (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,

avicide selected from the group of substances comprising chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (name according to IUPAC nomenclature) (23) and strychnine (745) + TX,

bactericide selected from the group of substances comprising 1-hydroxy-1H-pyridine-2-tion (name according to IUPAC nomenclature) (1222) + TX, 4-(cinoxacin-2-ylamino)benzosulfimide (name according to IUPAC nomenclature) (748) + TX, 8-hydroxynonenal (446) + TX, bronopol (97) + TX, dioctanoyl copper (name according to IUPAC nomenclature) (170) + TX, copper hydroxide (name according to IUPAC nomenclature) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodecen (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydralift (alternative name) [CCN] + TX, kasugamycin (483) + TX, cashamericapaydayloan (483) + TX, bis(dimethyldithiocarbamate) Nickel (name according to IUPAC nomenclature) (1308) + TX, nitrapyrin (580) + TX, Actelion (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, hydroxyanisole potassium (446) + TX, pyrobenzol (658) + TX, streptomycin (744) + TX, streptomycinresistant (744) + TX, telital (766) + TX, and thiomersal (alternative name) [CCN] + TX,

biological agent selected from the group of substances comprising Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus bdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subspecies aizawai (scientific name) (51) + TX, Bacillus thuringiensis subspecies israelensis (scientific name) (51) + TX, Bacillus thuringiensis subspecies japonensis (scientific name) (51) + TX, Bacillus thuringiensis subspecies kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subspecies tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla cornea (alternative name) (151) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative title) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H.megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae variety acridum (scientific name) (523) + TX, Metarhizium anisoplae kind anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N.lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua, multicapacity virus nuclear polyhedrosis (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX,

soil sterilizer selected from the group of substances comprising logmean (name according to IUPAC nomenclature) (542) and methyl bromide (537) + TX,

chemical sterilizer selected from the group of substances comprising atlat [CCN] + TX, Benazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimater (alternative name) [CCN] + TX, Hemel [CCN] + TX, hempa [CCN] + TX, metapa [CCN] + TX, matiatia [CCN] + TX, methylfolate [CCN] + TX, Morse [CCN] + TX, perfluro (alternative name) [CCN] + TX, Tepa [CCN] + TX, tihana (viola is rnative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

the insect pheromone selected from the group of substances comprising (E)-Dec-5-ene-1-ylacetic with (E)-Dec-5-ene-1-I (name according to IUPAC nomenclature) (222) + TX, (E)-tridec-4-EN-1-ylacetic (name according to IUPAC nomenclature) (829) + TX, (E)-6-methylhept-2-EN-4-ol (name according to IUPAC nomenclature) (541) + TX, (E + TX, Z)-tetradeca-4 + TX, 10-Dien-1-ylacetic (name according to IUPAC nomenclature) (779) + TX, (2)-dodec-7-EN-1-ylacetic (name according to IUPAC nomenclature) (285) + TX, (Z)-hexadec-11-enal (name according to IUPAC nomenclature) (436) + TX, (Z)-hexadec-11-EN-1-ylacetic (name according to IUPAC nomenclature) (437) + TX, (Z)-hexadec-13-EN-11-in-1-ylacetic (name according to IUPAC nomenclature) (438) + TX, (Z)-ICOS-13-EN-10-he (name according to IUPAC nomenclature) (448) + TX, (Z)-tetradec-7-EN-1-al (the name in the IUPAC nomenclature) (782) + TX, (Z)-tetradec-9-EN-1-ol (name of the item IUPAC) (783) + TX, (Z)-tetradec-9-EN-1-ylacetic (name according to IUPAC nomenclature) (784) + TX, (7E + TX, 9Z)-dodeca-7 + TX, 9-Dien-1-ylacetic (name according to IUPAC nomenclature) (283) + TX, (9Z + TX, 11TH)-tetradeca-9 + TX, 11-Dien-1-ylacetic (name according to IUPAC nomenclature) (780) + TX, (9Z + TX, 12E)-tetradeca-9 + TX, 12-Dien-1-ylacetic (name according to IUPAC nomenclature) (781) + TX, 14-methyloctane-1-ene (name according to IUPAC nomenclature) (545) + TX, 4-methylnonane-5-ol with 4-methylnonane-anom (name according to IUPAC nomenclature) (544) + TX, alpha multistriatus (alternative name) [CCN] + TX, brevicomis (alternative name) [CCN] + TX, cadrelor (alternative name) [CCN] + TX, Coleman (alternative name) (167) + TX, colour (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-EN-1-ylacetic (name according to IUPAC nomenclature) (286) + TX, dodec-9-EN-1-ylacetic (name according to IUPAC nomenclature) (287) + TX, dodeca-8 + TX, 10-Dien-1-ylacetic (name according to IUPAC nomenclature) (284) + TX, dominikaner (alternative name) [CCN] + TX, ethyl-4-methyloctanoic (name according to IUPAC nomenclature) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossiper (alternative name) (420) + TX, grandeur (421) + TX, grandeur I (alternative name) (421) + TX, grandeur II (alternative name) (421) + TX, grandeur III (alternative name) (421) + TX, grandeur IV (alternative name) (421) + TX, hexalen [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonicus (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, Lalor (alternative name) [CCN] + TX, lepler (alternative name) [CCN] + TX, medlar [CCN] + TX, negatively acid (alternative name) [CCN] + TX, methyleugenol (alternative name) (540) + TX, muscular (563) + TX, octadeca-2 + TX, 13-Dien-1-ilocate the (name according to IUPAC nomenclature) (588) + TX, octadeca-3 + TX, 13-Dien-1-ylacetic (name according to IUPAC nomenclature) (589) + TX, oralor (alternative name) [CCN] + TX, orichalum (alternative name) (317) + TX, Osterman (alternative name) [CCN] + TX, Sigler [CCN] + TX, Ardiden (alternative name) (736) + TX, sulcata (alternative name) [CCN] + TX, tetradec-11-EN-1-ylacetic (the name of the item IUPAC) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1(alternative name) (839) + TX, trimedlure2(alternative name) (839) + TX, trimedlure (alternative name) (839) and trunc-call (alternative name) [CCN] + TX,

repellent for insects selected from the group of substances comprising 2-(octylthio)ethanol (name according to IUPAC nomenclature) (591) + TX, mucoperiosteal (933) + TX, butoxy(polypropyleneglycol) (936) + TX, dibutyltin (name according to IUPAC nomenclature) (1046) + TX, dibutyl phthalate (1047) + TX, dibutylamine (name according to IUPAC nomenclature) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbonate [CCN] + TX, dimethylphthalate [CCN] + TX, ethylhexanediol (1137) + TX, examed [CCN] + TX, methin-butyl (1276) + TX, metilnikotinamid [CCN] + TX, oximat [CCN] and picaridin [CCN] + TX,

insecticide selected from the group of substances including 1 + TX, 1-dichloro-1-nitroethane (name according to nomenclature IUPAC/Chemical Abstracts) (1058) + TX, 1 + TX, 1-dichloro-2 + TX, 2-bis(4-ethylphenyl)ethane (the name in the IUPAC nomenclature) (1056) + TX, 1 + TX, 2-dichloropropane (name according to nomenclature IUPAC/Chemical Abstracts) (1062) + TX, 1 + TX, 2-dichloropropane 1 + TX, 3-dichloropropene (name according to IUPAC nomenclature) (1063) + TX, 1-bromo-2-chlorate (name according to nomenclature IUPAC/Chemical Abstracts) (916) + TX, 2 + t, 2 + TX, 2-trichloro-1-(3 + TX, 4-dichlorophenyl)ethyl acetate (name according to IUPAC nomenclature) (1451) + TX, 2 + TX, 2-dichlorovinyl-2-ethylsulfinylmethyl (name according to IUPAC nomenclature) (1066) + TX, 2-(1 + TX, 3-ditiolan-2-yl)phenyldimethylsilane (name according to nomenclature IUPAC/Chemical Abstracts) (1109) + TX, 2-(2-butoxyethoxy)utilitzant (name according to nomenclature IUPAC/Chemical Abstracts) (935) + TX, 2-(4 + TX, 5-dimethyl-1 + TX, 3-dioxolane-2-yl)fenilmetilketenom (name according to nomenclature IUPAC/Chemical Abstracts) (1084) + TX, 2-(4-chloro-3 + TX, 5-xylulose)ethanol (name according to IUPAC nomenclature) (986) + TX, 2-chlorineresistant (name according to IUPAC nomenclature) (984) + TX, 2-imidazolidone (name according to IUPAC nomenclature) (1225) + TX, 2-isovaleramide-1 + TX, 3-dione (name according to IUPAC nomenclature) (1246) + TX, 2-methyl(prop-2-inyl)aminopenicillanic (name according to IUPAC nomenclature) (1284) + TX, 2-thiocyanatomethylthio (name according to IUPAC nomenclature) (1433) + TX, 3-bromo-1-chlorpro-1-ene (name according to IUPAC nomenclature) (917) + TX, 3-methyl-1-phenylpyrazol-5-ultimatecarpage (name according to IUPAC nomenclature) (1283) + TX, 4-methyl(prop-2-inyl)amino-3 + TX, 5-xylylenediisocyanate (called the e nomenclature IUPAC) (1285) + TX, 5 + TX, 5-dimethyl-3-oxocyclohexa-1-energimiljoradet (name according to IUPAC nomenclature) (1085) + TX, abamectin (1) + TX, acetat (2) + TX, acetamiprid (4) + TX, asation (alternative name) [CCN] + TX, acetarsol [CCN] + TX, acrinathrin (9) + TX, Acrylonitrile (name according to IUPAC nomenclature) (861) + TX, alankar (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, Aldrin (864) + TX, allethrin (17) + TX, allocatedin (alternative name) [CCN] + TX, allistar (866) + TX, alpha-cypermethrin (202) + TX, alpha-Edison (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidation (870) + TX, amidation (872) + TX, aminocarb (873) + TX, Amiton (875) + TX, amitorization (875) + TX, amitraz (24) + TX, anabasine (877) + TX, amidation (883) + TX, AVI 382 (connecting code) + TX, AZ 60541 (connecting code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, attout (889) + TX, Delta-endotoxins of Bacillus thuringiensis (alternative name) (52) + TX, barium fluorosilicate preparation (alternative name) [CCN] + TX, barium polysulfide (name according to nomenclature IUPAC/Chemical Abstracts) (892) + TX, barten [CCN] + TX, Bayer 22/190 (research code) (893) + TX, Bayer 22408 (research code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, S-cyclopentadienyl the Zomer bioallethrin (alternative name) (79) + TX, bioeconomical [CCN] + TX, bioprotein (908) + TX, bioresmethrin (80) + TX, bis(2-chlorotalonil) ether (name according to IUPAC nomenclature) (909) + TX, bistriflate (83) + TX, borax (86) + TX, brianalexat (alternative name) + TX, pumpevents (914) + TX, bromocyclen (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bofenkamp (924) + TX, buprofezin (99) + TX, betacar (926) + TX, butamifos (927) + TX, butocarboxim (103) + TX, Boutonnat (932) + TX, butoxycarboxim (104) + TX, butylparaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (name according to IUPAC nomenclature) (111) + TX, camphechlor (941) + TX, carbanilate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulphide (name according to nomenclature IUPAC/Chemical Abstracts) (945) + TX, carbon tetrachloride (name according to IUPAC nomenclature) (946) + TX, carbophenothion (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, carthagecreated (123) + TX, zevalin (alternative name) (725) + TX, chlorobicyclo (960) + TX, chlordane (128) + TX, Chlordecone (963) + TX, Chlordimeform (964) + TX, chlorodimethylsilane (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, Chlorfenvinphos (131) + TX, chlorfluazuron (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorphoxim (989) + TX, chlorpropham (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + the X, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, zanarini (696) + TX, CIS-resmethrin (alternative name) + TX, resmethrin (80) + TX, claritin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, acetoarsenite copper [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, comitat (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (research code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, zantout (1020) + TX, cyclotron [CCN] + TX, cicloprofen (188) + TX, cyfluthrin (193) + TX, cigalotrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cetiat (alternative name) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT (219) + TX, carbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamides (1044) + TX, diazinon (227) + TX, deception (1050) + TX, dichlofenthion (1051) + TX, dichlorvos (236) + TX, declivous (alternative is name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl-5-methylpyrazole-3-infostat (name according to IUPAC nomenclature) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, demeton (1085) + TX, dimethoate (262) + TX, demetrin (1083) + TX, dimethylene (265) + TX, dimetilan (1086) + TX, Dinex (1089) + TX, Dinex-diclectin (1089) + TX, dynprop (1093) + TX, dinoseb (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, giovanola (1099) + TX, dioxybenzone (1100) + TX, dioxane (1101) + TX, dioxathion (1102) + TX, disulfoton (278) + TX, deticates (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (research code) (1118) + TX, emamectin (291) + TX, amaneciendo (291) + TX, EMRS (1120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1121) + TX, endrin (1122) + TX, ERVR (1123) + TX, EPN (297) + TX, apoptone (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, Etats (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, etoac-methyl (1134) + TX, ethoprophos (312) + TX, ethyl formate (name according to IUPAC nomenclature) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylenedibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, atop nprocs (319) + TX, etrimfos (1142) + TX, EXD (1143) + TX, famphur (323) + TX, fenamiphos (326) + TX, pensator (1147) + TX, fenchlorphos (1148) + TX, fanatical (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, tenoxicam (1153) + TX, fenoxycarb (340) + TX, generatin (1155) + TX, fenpropathrin (342) + TX, feneral (alternative name) + TX, fensulfothion (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (registration No. CAS: 272451-65-7) + TX, flucturion (1168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluential (1169) + TX, flutterin [CCN] + TX, flufenoxuron (370) + TX, flavandiols (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (research code) (1185) + TX, fonofos (1191) + TX, formetanate (405) + TX, formmanager.load (405) + TX, formation (1192) + TX, formparent (1193) + TX, tomatlan (1194) + TX, hasperat (1195) + TX, fosthiazate (408) + TX, fostimon (1196) + TX furathiocarb (412) + TX, pyrethrin (1200) + TX, gamma cigalotrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine (422) + TX, GY-81 (research code) (423) + TX, halftracks (424) + TX, halogenated (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heteropus [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, checkwinner (1223) + TX, Imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, logmean (name according to IUPAC nomenclature) (542) + TX, IPSP for acquiring (1229) + TX, isazofos (1231) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, Isodrin (1235) + TX, isofenphos (1236) + TX, Izolan (1237) + TX, isoprocarb (472) + TX, isopropyl O-(methoxyaminomethyl)salicylate (name according to IUPAC nomenclature) (473) + TX, isoprothiolane (474) + TX, satiat (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, idents (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, CANopen (484) + TX, lambda cigalotrin (198) + TX, arsenate of lead [CCN] + TX, lepeletier (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, liempo (1251) + TX, lufenuron (490) + TX, litigation (1253) + TX, m-cameneletricanude (name according to IUPAC nomenclature) (1014) + TX, magnesium phosphide (name according to IUPAC nomenclature) (640) + TX, Malathion (492) + TX, malaanonan (1254) + TX, makedocs (1255) + TX, mecarbam (502) + TX, macartan (1258) + TX, menazon (1260) + TX, mephosfolan (1261) + TX, chloride mercury (I) (513) + TX, resolvents (1263) + TX, metaflumizone (CCN) + TX, METAM (519) + TX, METAM-potassium (alternative name) (519) + TX, METAM-sodium (519) + TX, methacrifos (1266) + TX, metamidophos (527) + TX, methysulfonylmethane (name according to nomenclature IUPAC/Chemical Abstracts) (1268) +TX, mitigation (529) + TX, methiocarb (530) + TX, metacreation (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methin-butyl (1276) + TX, Metatron (alternative name) (533) + TX, Methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methylisothiocyanate (543) + TX, chloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX metofluthrin [CCN] + TX, metolcarb (550) + TX, methoxamine (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin (alternative name) [CCN] + TX, metafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, porpotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalie (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (name according to nomenclature IUPAC/Chemical Abstracts) (1303) + TX, NC-170 (research code) (1306) + TX, NC-184 (connecting code) + TX, nicotine (578) + TX, nicotinuric (578) + TX, diflouride (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilases (1313) + TX, complex nitrilases:zinc chloride composition 1:1 (1313) + TX, NNI-0101 (connecting code) + TX, NNI-0250 (connecting code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, O-5-dichloro-4-iopener-O-athletesfoot (name according to IUPAC nomenclature) (1057) + TX, O,O-diethyl-O-4-methyl-2-oxo-2H-chromen-7-infostation (name according to IUPAC nomenclature) (1074) + TX, O,O-ITIL-O-6-methyl-2-propylpyrimidine-4-phosphorothioate (name according to IUPAC nomenclature) (1075) + TX, O,O,O',O'-tetrapropylammonium (name according to IUPAC nomenclature) (1424) + TX, oleic acid (name according to IUPAC nomenclature) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxidation (1324) + TX, oxydisulfoton (1325) + TX, PP'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, perfluro (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenolate (name according to IUPAC nomenclature) (623) + TX, permethrin (626) + TX, mineral oils (alternative name) (628) + TX, PH 60-38 (research code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, pentat (631) + TX, Fort (636) + TX fosalan (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, fossiler (1339) + TX, phosphamidon (639) + TX, phosphine (name according to IUPAC nomenclature) (640) + TX, phoxim (642) + TX, facsim-methyl (1340) + TX, perimeters (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, isomers of polychlorobenzene (name according to IUPAC nomenclature) (1346) + TX, polychloroterphenyl (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precoce I (alternative name) [CCN] + TX, precoce II (alternative name) [CCN] + TX, precoce III (alternative name) [CCN] + TX, primitivos (1349) + TX, profenofos (662) + TX, perflutren [CCN] + TX, bromacil (1354) + TX, promecarb (1355) + T is, proppos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, protection (1360) + TX, prothiofos (686) + TX, procoat (1362) + TX, protrient [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, prismatron (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, predatation (701) + TX, pyrimidifen (706) + TX, perimeter (1370) + TX, pyriproxifen (708) + TX, Cassia (alternative name) [CCN] + TX, finalpos (711) + TX, finalpos-methyl (1376) + TX, gination (1380) + TX, histiotus (1381) + TX, R-1492 (research code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (research code) (723) + TX, RU 25475 (research code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, Srdan (1389) + TX, sabots (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (connecting code) + TX, SI-0205 (connecting code) + TX, SI-0404 (connecting code) + TX, SI-0405 (connecting code) + TX, selfloader (728) + TX, SN 72129 (research code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (name according to nomenclature IUPAC/Chemical Abstracts) (1399) + TX, sodium fluorosilicate preparation (1400) + TX, pentachlorophenoxide sodium (623) + TX, selenate sodium (the name but is enclature IUPAC) (1401) + TX, the sodium thiocyanate [CCN] + TX, sofabed (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetramat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfurylchloride (756) + TX, sulprofos (1408) + TX, resin oils (alternative name) (758) + TX, Tau-fluvalinate (398) + TX Casimir (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TERR (1417) + TX, terretris (1418) + TX, terban (alternative name) + TX, terbufos (773) + TX, tetrachlorethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + TX, titanox (alternative name) + TX, thiamethoxam (792) + TX, micropos (1428) + TX, dicarboxyl (1431) + TX, thiocyclam (798) + TX, titillators (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801) + TX, thionazin (1434) + TX, thiosulfat (803) + TX, thiosulfat-sodium (803) + TX, thuringensis (alternative name) [CCN] + TX, tolpinrud (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamides (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, treasure (alternative name) + TX, trichlorfon (824) + TX, trichlormethane-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, tritanopes (1455) + TX, triflumuron (835) + TX, trimeter (840) + TX, triplen (1459) + TX, VA is idation (847) + TX, unilibro [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, HMS (853) + TX, killchar (854) + TX, YI-5302 (a link code) + TX, Zeta-cypermethrin (205) + TX, decamethrin (alternative name) + TX, zinc phosphide (640) + TX, sulprofos (1469) and ZXI 8901 (research code) (858) + TX,

molluscoid selected from the group of substances comprising bis(tributylamine)oxide (name according to IUPAC nomenclature) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, acetoarsenite copper [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, phosphate iron (II) (name according to IUPAC nomenclature) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX niclosamide (576) + TX, nitrosamide-alamin (576) + TX, pentachlorophenol (623) + TX, pentachlorophenoxide sodium (623) + TX, Casimir (1412) + TX, thiodicarb (799) + TX, tributyltinoxide (913) + TX, Trifanov (1454) + TX, trimeter (840) + TX, triphenylborane (name according to IUPAC nomenclature) (347) and triphenylborane (name according to IUPAC nomenclature) (347) + TX,

nematocide selected from the group of substances comprising AKD-3088 (connecting code) + TX, 1 + TX, 2-dibromo-3-chloropropane (name according to nomenclature IUPAC/Chemical Abstracts) (1045) + TX, 1 + TX, 2-dichloropropane (name according to nomenclature IUPAC/Chemical Abstracts) (1062) + TX, 1 + TX, 2-dichloropropane 1 + TX, 3-dichloropropene (name according to IUPAC nomenclature) (1063) + TX, 1 + TX 3-dichloropropene (233) + TX, 3 + TX, 4-dichlorotetrafiuoroethane 1 + TX, 1-dioxide (name according to nomenclature IUPAC/Chemical Abstracts) (1065) + TX, 3-(4-chlorophenyl)-5-methyladenine (name according to IUPAC nomenclature) (980) + TX, 5-methyl-6-thioxo-1 + TX, 3 + TX, 5-thiadiazine-3-luksusowe acid (name according to IUPAC nomenclature) (1286) + TX, 6-isopentylamine (alternative name) (210) + TX, abamectin (1) + TX, acetarsol [CCN] + TX, alankar (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (connecting code) + TX, banknotes [CCN] + TX, benomyl (62) + TX, butylparaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulphide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamides (1044) + TX, dichlofenthion (1051) + TX, declivous (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, amaneciendo (291) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylenedibromide (316) + TX, fenamiphos (326) + TX, feneral (alternative name) + TX, fensulfothion (1158) + TX, fosthiazate (408) + TX, fostimon (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (research code) (423) + TX, heteropus [CCN] + TX, logmean (name nomenclature IUPAC) (542) + TX, samities (1230)+ TX, isazofos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, macartan (1258) + TX, METAM (519) + TX, METAM-potassium (alternative name) (519) + TX, METAM-sodium (519) + TX, methyl bromide (537) + TX, methylisothiocyanate (543) + TX, milbemycin (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX the composition of Myrothecium verrucaria (alternative name) (565) + TX, NC-184 (connecting code) + TX, oxamyl (602) + TX, Fort (636) + TX, phosphamidon (639) + TX, phosphonates [CCN] + TX, sabots (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terban (alternative name) + TX, terbufos (773) + TX, tetrachloride (name according to IUPAC nomenclature/Chemical Abstracts) (1422) + TX, titanox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, treasure (alternative name) + TX, Xylenol, carbonaceous [CCN] + TX, YI-5302 (a link code) and zeatin (alternative name) (210) + TX,

the nitrification inhibitor selected from the group of substances comprising ethylxanthate potassium [CCN] and nitrapyrin (580) + TX,

activator of plants selected from the group of substances comprising acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, pyrobenzol (658) and the extract of Reynoutria sachalinensis (alternative name) (720) + TX,

a rodenticide selected from the group of substances comprising 2-isovaleramide-1 + TX, 3-dione (trade names is on the nomenclature IUPAC) (1246) + TX, 4-(cinoxacin-2-ylamino)benzosulfimide (name according to IUPAC nomenclature) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, Antu (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bestieee (912) + TX, brodifacoum (89) + TX, bromadiolon (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diazinon (273) + TX, ergocalciferol (301) + TX, flocumaphen (357) + TX, peracetate (379) + TX, fluprofen (1183) + TX, flowproportional (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, logmean (name according to IUPAC nomenclature) (542) + TX, lindane (430) + TX, magnesium phosphide (name according to IUPAC nomenclature) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, VOSClim (1336) + TX, phosphine (name according to IUPAC nomenclature) (640) + TX, phosphorus [CCN] + TX, pinton (1341) + TX, potassium arsenite [CCN] + TX, Pianoro (1371) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, fluoroacetate sodium (735) + TX, strychnine (745) + TX, sulfate thallium [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,

a synergist selected from the group of substances comprising 2-(2-butoxyethoxy)ethylpiperazine (name according to IUPAC nomenclature) (934) + TX, 5-(1 + TX, 3-benzodioxol-5-yl)-3-exerci logex-2-northward (name according to IUPAC nomenclature) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (research code) (498) + TX, MGK 264 (research code) (296) + TX, piperonylbutoxide (649) + TX, pipracil (1343) + TX, an isomer of propyl (1358) + TX, S421 (research code) (724) + TX, sesamex (1393) + TX, sesamolin (1394) and sulfoxide (1406) + TX,

repellent for animals selected from the group of substances containing anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, Dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine (422) + TX, methiocarb (530) + TX, pyridin-4-amine (name according to IUPAC nomenclature) (23) + TX, thiram (804) + TX, trimeter (840) + TX, zinc naphthenate [CCN] and Zir (856) + TX,

virucide selected from the group of substances, including imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,

crickets RAS plants selected from the group of substances, including mercury oxide (II) (512) + TX, Actelion (590) and thiophanate-methyl (802) + TX,

insecticide selected from the group comprising the compounds of formula a-1(A-1) + TX, formula a-2(A-2) + TX, formula a-3(A-3) + TX, formula a-4(A-4) + TX, formula A-5(A-5) + TX, formula A-6(A-6) + TX, f is rmula a-7 (A-7) + TX, formula A-8(A-8) + TX, formula A-9(A-9) + TX, formula A-10(A-10) + TX, formula A-11(A-11) + TX, formula A-12(A-12) + TX, formula A-13(A-13) + TX, formula A-14(A-14) + TX, formula a-15(A-15) + TX, formula A-16(A-16) + TX, formula A-17(A-17) + TX, formula A-18(A-18) + TX, formula A-19(A-19) + TX, formula A-20(A-20) + TX, formula A-21(A-21) + TX, formula A-22(A-22) + TX, formula a-23(A-23) + TX, formula A-24(A-24) + TX, formula A-25(A-25) + TX and formulas A-26(A-26) + TX,

and biologically active compounds selected from the group comprising glyphosate [1071-83-6] and its salts (demoniaca [69254-40-6]) isopropylammonium [38641-94-0], monoammonium [40465-66-5], potassium [70901-20-1], sequentialy [70393-85-0], trimedia[81591-81-3]), glufosinate [52676-47-2] and its salts (such as ammonium [77182-82-2]), azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [116255-48-2] + TX, tsyprokonazolu [94361-06-5] + TX, difenoconazol [119446-68-3] + TX, di is econazole [83657-24-3] + TX, epoxiconazol [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, Fluconazol [136426-54-5] + TX, flusilazol [85509-19-9] + TX, flutriafol [76674-21-0] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, kabekona [86598-92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, perforated [101903-30-4] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pirivenas [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazol [60207-90-1] + TX, semiconical [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancymidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemont [1593-77-7] + TX, fenpropidin [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, mepanipyrim [110235-47-7] + TX, Pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludyoksonil [152641-86-1] + TX, benalaxyl [71626-11-4] + TX, parallaxis [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, furac [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, dibakar [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazol [148-79-8] + TX, chlozolinate [84332-86-5] + TX, diplozoon [24201-58-9] + TX, iprodion [36734-19-7] + TX, mickleton [54864-61-8] + TX, procymidon [32809-16-8] + TX, is vinclozolin [50471-44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fanforum [24691-80-3] + TX, flutolanil [66332-96-5] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, pentopia [183675-82-3] + TX, leflunomid [130000-40-7] + TX, guazatine [108173-90-6] + TX, Dodin [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, AZOXYSTROBIN [131860-33-8] + TX, dimoxystrobin [149961-52-4] + TX, electroboard {Proc. SRC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metamyosyn [133408-50-1] + TX, Trifloxystrobin [141517-21-7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, MANCOZEB [8018-01-7] + TX, MANEB [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071-83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, Zir [137-30-4] + TX, captafol [2425-06-1] + TX, Captan [133-06-2] + TX, dichlofluanid [1085-98-9] + TX, perimed [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanid [731-27-1] + TX, Bordeaux liquid [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-39-1] + TX, marcopper [53988-93-5] + TX, oxidat copper [10380-28-6] + TX, dinocap [131-72-6] + TX, nitrates-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenfos [26087-47-8] + TX, isoprothiolane [50526-35-1] + TX, forgiven [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-8-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [239-01-2] + TX, chloroneb [2675-77-6] + TX, CHLOROTHALONIL [1897-45-6] + TX, cyflufenamid [526409-60-3] + TX, having cymoxanil [57966-95-7] + TX, Dylan [117-80-6] + TX, diclocil [139920-32-4] + TX, declomycin [62865-36-5] + TX, dicloran [99-30-9] + TX, dietphenterm [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (floorf) [211867-47-9] + TX, dithianon [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [135267-57-3] + TX, fenamidone [161326-34-7] + TX, phenoxyl [11585 2-48-7] + TX, fentin [668-34-8] + TX, verison [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, glucolipid [106917-52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminum [39148-24-8] + TX, hymexazol [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (cyazofamid) [120116-88-3] + TX, kasugamycin [6980-18-3] + TX, metasurfaces [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phtalic [27355-22-2] + TX, polixeni [11113-80-7] + TX, provenzal [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazid [189278-12-4] + TX, peregian [57369-32-1] + TX, jenoxifen [124495-18-7] + TX, quintozene [82-68-8] + TX, sulphur (7704-34-9] + TX, tudinal [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamid [374726-62-2] + TX, the compound of formula F-1

,

in which Ra5represents trifluoromethyl or deformity (WO 2004/058723) + TX, the compound of formula F-2

,

in which Ra6means Tr is vermeil or deformity (WO 2004/058723) + TX, racemic compound of formula F-3 (SYN)

,

in which Ra7represents trifluoromethyl or deformity (WO 2004/035589) + TX,

the racemic mixture of the formula F-4 (anti)

,

in which Ra7represents trifluoromethyl or deformity (WO 2004/035589) + TX, the compound of formula F-5

,

which is epimeno mixture of racemic compounds of formula F-3 (SYN) and F-4 (anti), where the ratio of the quantities of racemic compounds of formula F-3 (SYN) to the amount of racemic compounds of formula F-4 (anti) is from 1000:1 to 1:1000, and in which Ra7represents trifluoromethyl or deformity (WO 2004/035589) + TX, the compound of formula F-6

,

in which Ra8represents trifluoromethyl or deformity (WO 2004/035589) + TX,

racemic compound of formula F-7 (TRANS)

,

in which Ra9represents trifluoromethyl or deformity (WO 03/074491) + TX, the racemic compound of formula F-8 (CIS)

,

in which Ra9represents trifluoromethyl or deformity (WO 03/074491) + TX, the compound of formula F-9

,

which is a mixture of racemic compounds of formula F-7 (TRANS) and F-8 (CIS), where the ratio of the number of racemic connected to the I formula F-7 (TRANS) to the amount of racemic compounds of formula F-8 (CIS) is from 2:1 to 100:1; in which Ra9represents trifluoromethyl or deformity (WO 03/074491) + TX,

the compound of formula F-10

,

in which R10represents trifluoromethyl or deformity (WO 2004/058723) + TX, the racemic compound of formula F-11 (trance)

,

in which R11represents trifluoromethyl or deformity (WO 03/074491) + TX, the racemic compound of formula F-12 (CIS)

,

in which R11represents trifluoromethyl or deformity (WO 03/074491) + TX, the compound of formula F-13

,

which is a racemic mixture of the formula F-11 (TRANS) and F-12 (CIS), and in which R11represents trifluoromethyl or deformity (WO 03/074491) + TX, the compound of formula F-14

,

(WO 2004/058723) + TX, the compound of formula F-15

[214706-53-3],

+ TX.

References in square brackets after the active ingredients, for example, [3878-19-1] mean registration number Chemical Abstracts. Compounds of formula a-1-A-26 described in WO 03/015518 or in WO 04/067528. The above components for mixing are known. If the active ingredients are included in the publication "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C.D.S.Tomlin; The British Crop Protection Council], in the present invention are described with indication of all RMS is the part item number for the particular connection; for example, the connection "abamectin" described by indicating the number of positions (1). If the above in the present invention for a particular connection specified "[CCN]", then consider the connection is included in the publication "Compendium of Pesticide Common Names", which can be found on the Internet [.Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the connection acetool" described on the Internet at the address http://www.alanwood.net/pesticides/acetoprole.html.

For most of the active ingredients described above, the present invention provides a so-called "common name"in some cases use their "common name ISO" or other "common name". If the name is not "common name", the feature names used instead for the specific compounds listed in parentheses; in this case, use the name in the IUPAC nomenclature, the name of the item IUPAC/Chemical Abstracts, "chemical name", "traditional name", "connection name" or "research code" or, if neither one of these names and do not use a "common name", then use the expression "alternative name". "CAS Reg. No indicates the registration number Chemical Abstracts.

The mixture of active ingredients compounds of the formula I selected from tables T1-T, the asset is diversified ingredients, as described above, includes a compound selected from tables T1-T, and the active ingredient described above, preferably in a mixing ratio of 100:1 to 1:6000, preferably from 50:1 to 1:50, more preferably in the ratio of 20:1 to 1:20, even more preferably from 10:1 to 1:10, more preferably from 5:1 to 1:5, with particular preference the ratio of 2:1 to 1:2, and the ratio of 4:1 to 2:1 is preferred, primarily the ratio of 1:1 or 5:1 or 5:2 or 5:3 or 5:4 or 4:1 or 4:2 or 4:3 or 3:1 or 3:2 or 2:1 or 1:5 or 2:5 or 3:5 or 4:5 or 1:4, or 2:4 or 3:4 or 1:3 or 2:3 or 1:2 or 1:600 or 1:300 or 1:150 or 1:35 or 2:35, 4:35 or 1:75, or 2:75, 4:75 or 1:6000, or 1:3000 or 1:1500 or 1:350, or 2:350, 4:350, or 1:750, or 2:750, or 4:750. It should be understood that these ratios include, on the one hand, mass ratio, and, on the other hand, the molar ratio.

Mixture comprising the compound of formula I selected from tables T1-T, and one or more active ingredients as described above can be used for example, in one ready-to-use mixture, in the form of a combined mixture for spraying comprising separate preparations of the active ingredients alone, such as tank mixture and apply to combin rowanna application of the active ingredients alone when they are applied consistently, i.e. one after the other in a fairly short period of time, such as belonging to a few hours or days. In the practical implementation of the present invention the procedure for making compounds of formula I selected from tables T1-T, and the active ingredients described above, is not significant.

Biological examples: fungicidal effect

Example-1: Plasmopara viticola: downy mildew of grapevine, helpful study:

Plasmopara viticola (downy mildew of grapevine): Disks vine leaves were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (80,000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated at 6 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample. (0 = not happening destruction Plasmopara viticola, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular the connection R.10 the detection is characteristic activity, more than 50%, with the rate equal to 200 ppm million

Example b-2 Botrytis cinerea (Grey rot, helpful study:

Botrytis cinerea (grey mould): Drives the bean leaves were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (60000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated at 3 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample. (0 = not happening destruction Botrytis cinerea, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular the connection R.29 detects activity that exceeds 50%, at a rate of flow equal to 200 ppm million

Example b-3: Erysiphe graminis f.sp. tritici: powdery mildew of wheat, helpful study:

Erysiphe graminis f.sp. tritici (powdery mildew of wheat): the leaf Segments of wheat were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, 0,025 Tween 20). After drying, the leaf disks were inoculable fungal spores (50 conidia/mm2). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated 7 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample. (0 = not happening destruction Erysiphe graminis f.sp. tritici, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R, R, R.21, R.22, R.26, R, R.29, R, R.35, R, R, R, R, R, R, R, R, R, R, R and R find an activity greater than 50%, with the rate equal to 200 ppm million

Example b-4: Erysiphe graminis f.sp. hordei: powdery mildew of barley, the study cure:

Erysiphe graminis f.sp. hordei (powdery mildew of barley): Segments of barley leaves were placed on agar in advance tablet (24 holes). The leaf disks were inoculable fungal spores (120 conidia/mm2). After 24 h, the leaf disks were sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After an appropriate incubation period of healing fungicidal activity of the compounds was evaluated 7 days after inoculation, as ysanne disease damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample (0 = not happening destruction Erysiphe graminis f.sp. hordei, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R, R, R, R, R, R, r.11, R, R.15, R.16, 17 and R find an activity greater than 50%, with the rate equal to 200 ppm million

Example B-5: Puccinia recondita: Brown rust of wheat, helpful study:

Puccinia recondita (brown rust): the leaf Segments of wheat were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (45,000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was assessed 8 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample (0 = not happening destruction Puccinia recondita, 100% = complete destruction). In this study, the compounds listed in table R, above, find a good active is here. In particular compounds R, P.11, P.26, R, R.29, R.31, R.35, 51, R, R, R, R, R, R, R, R, R, R and R find an activity greater than 50%, with the rate equal to 200 ppm million

Example B-6: Puccinia recondita: Brown rust of wheat research cure:

Description of the study methodology Puccinia recondita (brown rust):

The leaf segments of wheat were placed on agar in advance tablet (24 holes). Then the leaf disks were inoculable spore suspension of fungi (45,000 conidia/ml). One day after inoculation inflicted prepared test solution (2% dimethyl sulfoxide, of 0.025% Tween 20). After an appropriate incubation period of healing fungicidal activity of the compounds was assessed 8 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample (0 = not happening destruction Puccinia recondita, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R.26, R, R.29, R.31, R.35, R.36, R, R, R, R, R, R, R, RR, R, R, R and R find an activity greater than 50%, with the rate equal to 200 ppm million

Example B-7: Phaeosphaeria nodorum: Spotting Koloskova scales wheat,helpful study:

Description of the study methodology Phaeosphaeria nodorum (synonyms Septoria nodorum, Leptosphaeria nodorum, Septoria Koloskova scales wheat (Septoria leaf spot): the leaf Segments of wheat were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (500,000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated 4 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample (0 = not happening destruction of Phaeosphaeria nodorum, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R and R.29 find an activity greater than 50%, with the rate equal to 200 ppm million

Example B-8: Magnaporthe grisea: Pyricularia rice, helpful study:

Description of the study methodology Magnaporthe grisea (synonym Pyricularia oryzae), pyricularia of Fig. The leaf segments were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% Dima is insulted, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (90'000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated 5 days after inoculation, as the disease caused by damage to the discs of leaves, and was calculated as the percentage efficiency compared to untreated infected control sample (0 = not happening destruction Magnaporthe grisea, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R, R and R find an activity greater than 50%, with the rate equal to 200 ppm million

Example B-9: Pyrenophora teres: Net blotch of barley, helpful study:

Description of the study methodology Pyrenophora teres (net blotch): Segments of barley leaves were placed on agar in advance tablet (24 holes) and was sprayed prepared analyzed solutions (2% dimethyl sulfoxide, of 0.025% Tween 20). After drying, the leaf disks were inoculable spore suspension of fungi (25,000 conidia/ml). After an appropriate incubation period of preventive fungicidal activity of the compounds was evaluated 4 days after inoculation, as the disease caused by damage to the discs of leaves, and the upper margin of the Ali, as expressed in percent efficiency compared with untreated infected control sample (0 = not happening destruction Pyrenophora teres, 100% = complete destruction). In this study, the compounds listed in table R, above, finds a good activity. In particular compounds R, R, R, R, R, R, R and R find an activity greater than 50%, with the rate equal to 200 ppm million

1. The way to combat the infestation of useful plants by phytopathogenic microorganisms or warnings, in which the compound of formula I or a composition comprising this compound as an active ingredient, applied to plants, to parts thereof or the place of their growth, in which the compound of formula I is a
,
in which
aa) R1and R2independently of one another denote hydrogen, C1-C7alkyl, C2-C6alkenyl; or
af) or R1or R2does
af1) C1-C6alkoxygroup; or
ah) R1and R2independently of one another denote A group-;
where A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from GRU the dust, including nitrogen, and the 3-10 membered ring system may be mono - or polyamidine
A1) substituents, independently selected from the group comprising halogen, =O, C1-C6alkyl and C1-C6alkoxygroup; or
A3) substituents, independently selected from the group comprising C1-C6alkylsulfonyl; or
aj) R1and R2together form a C2-C6Allenby bridge; or
ak) R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
ba) R3, R4and R7independently from each other represent
ba1) hydrogen, halogen, cyano or nitro-group; or R3, R4and R7independently of one another denote (R51)(R52)(R53Si - or (R51)(R52)(R53)Si-(C1-C6alkyl)-; where R51, R52and R53independently of one another denote C1-C6alkyl;
or R3, R4and R7independently from each other represent
ba2) C1-C6alkylsulfonyl;
or R3, R4and R7independently from each other represent
ba3) C1-C6alkyl, C2-C6alkenyl or C2-C6quinil, or C1-C6alkyl, C2-C6alkenyl or C2-C6quinil, mono - or politeley substituents, independently selected from the group including the non halogen and C 1-C6alkoxygroup;
or R3, R4and R7independently from each other represent
ba5) phenyl, or benzyl or benzyl mono - or politeley substituents, independently selected from the group comprising halogen and C1-C6alkyl; or
bb) R3, R4and R7independently of one another denote A group where the group A is as defined above in section ah);
ca) R5denotes hydrogen, C1-C12alkyl, C2-C12alkenyl or C2-C12quinil, or denotes a C1-C12alkyl or C2-C12alkenyl mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, formyl, C2-C7alkylsulphonyl and C1-C6alkoxygroup; or
cb1) R5represents C2-C12alkylaryl or C2-C12alkoxycarbonyl; or
cc) R5means (R51)(R52)(R53Si - or (R51)(R52)(R53)Si-(C1-C12alkyl)-; or
cd) R5represents C1-C6alkyl-B-C1-C12alkyl-, where the group B denotes a-C(=NOR59)-, where R59denotes hydrogen or C1-C6alkyl; or
cf) R5refers to A-, And-(C1-C6alkyl)-, And-(C2-C6alkenyl)-, And-(C2-C6-quinil)- or-(C3-C8the CEC is alkyl)-; where the group A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine
A1) substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, =O, C1-C6alkyl, C2-C6alkenyl, C1-C6halogenated, C2-C6halogenoalkanes, C1-C6alkoxygroup and C3-C6alkenylacyl; or
A2) substituents, independently selected from the group comprising (C1-C6alkyl)C(=NOR59)-, where R59denotes hydrogen or C1-C6alkyl; or
A3) substituents, independently selected from the group comprising C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or
A4) substituents, independently selected from the group comprising - NR57R58where R57and R58independently of one another denote hydrogen or C1-C6alkyl; or
A5) substituents, independently selected the C group, including C2-C7alkylsulphonyl and C2-C7alkoxycarbonyl; or
A7) substituents, independently selected from the group comprising phenyl, fenoxaprop and benzyl, where phenyl, fenoxaprop and benzyl, in turn, can be mono - or polyamideimide on the phenyl ring by substituents independently selected from the group comprising halogen;
d) R6denotes hydrogen, -SH;
and agronomically acceptable salts / N-oxides of these compounds;
in which, if
R1and R2independently of one another denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6halogenated, C1-C6alkyl, halogen, cyano, a nitro-group, C1-C4alkoxygroup, phenyl, phenyl substituted by halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53independently of one another represent halogen, cyano, C1-C6alkyl, C2-C6alkenyl, C3-C8cycloalkyl, C5-C8cycloalkenyl, C2-C6quinil, C1-C6alkoxygroup, benzyl or phenyl;
R4denotes hydrogen, halogen, phenyl, who imidazolyl, an amino group, a C1-C6alkoxygroup or C1-C6alkyl;
R5refers to a group A, where A denotes a 3 to 10-membered monocarbocyclic or condensed beerbottles ring system which may be aromatic, partially unsaturated or fully saturated, where this is a 3-10-membered ring system may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl, group A should be mono - or polyamidine substituents other than halogen, C1-C6of alkyl, C1-C6halogenoalkane, C1-C6alkoxygroup and C1-C6ancilliary.

2. The method according to claim 1, in which R1and R2independently of one another denote hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl or C3-C6cycloalkyl mono - or politeley substituents, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup; or R1and R2together form a C2-C6Allenby bridge; or R and R2together with the connecting nitrogen atom of form pyrrolidone group.

3. The method according to claim 1, in which R6denotes hydrogen.

4. The method according to claim 1, in which R6refers to-SH.

5. The method according to claim 1, in which R7denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated, halogen or cyano.

6. The method according to claim 1, in which R4denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated, C3-C7cycloalkyl, halogen, cyano, C1-C6alkylsulfonyl, aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group; or aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidinyl group, each of which, in turn, is mono - or polyamidine substituents selected from the group comprising methyl, halogen; or R4denotes phenyl or phenyl which is mono - or preparation of polysubstituted Deputy is mi, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup.

7. The method according to claim 1, in which R3denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated, C2-C6alkenyl, C2-C6quinil, C3-C7cycloalkyl, halogen, three(C1-C4alkyl)silyl, C1-C6alkylsulfonyl, phenyl, aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group; or R3means aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group, mono - or polyamidine substituents, independently selected from the group comprising methyl and halogen, or denotes phenyl, mono - or politeley substituents, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup.

8. The method according to claim 1, in which R5denotes phenyl, phenyl-C1 -C6alkyl, phenyl-C3-C8cycloalkyl or phenyl-C2-C6alkenyl, or phenyl, phenyl-C1-C6alkyl, phenyl-C3-C7cycloalkyl or phenyl-C2-C6alkenyl, mono - or politeley substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, C1-C6alkyl, C1-C6halogenated, C2-C6alkenyl, C2-C6halogenoalkanes, C1-C6alkoxygroup, C3-C6alkenylacyl, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl.

9. The method according to claim 1, in which R5denotes hydrogen, (R51)(R52)(R53)Si-(C1-C12alkyl)-, Tris1-C6alkylsilane, C1-C12alkyl, C3-C12alkenyl, C3-C12quinil, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C12alkyl, C5-C10cycloalkenyl or C1-C6alkoxy-C1-C12alkyl, or R5represents C1-C12alkyl, C3-C12alkenyl, C3-C12quinil or C3-C10cycloalkyl, mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, CHO and C1-C6alkoxygroup.

10. The method according to claim 1, inwhich
R1and R2independently of one another denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6halogenated, C1-C6alkyl, halogen, cyano, a nitro-group, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen, halogen, phenyl, imidazolyl or C1-C6alkyl;
R5represents C1-C12alkyl or A group, where
A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine
substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl.

11. The method according to claim 10, in which the R 3denotes hydrogen, C1-C6alkyl, halogen, cyano, a nitro-group, phenyl or phenyl containing as substituents halogen.

12. The method according to claim 1, in which
R1and R2independently of one another denote C1-C6alkyl, C3-C7cycloalkyl, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6alkyl, C1-C6halogenated, halogen, cyano, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen, halogen or C1-C6alkyl;
R5represents C1-C6alkyl, phenyl or C1-C6alkyl, pyridyl or phenyl or pyridyl mono - or disubstituted by substituents selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl.

13. The method according to item 12, in which
R1and R2independently of one another denote C1-C6alkyl, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1 -C6alkyl, halogen, cyano, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen or C1-C6alkyl;
R5represents C1-C6alkyl, phenyl or pyridyl, or phenyl or pyridyl mono - or disubstituted by substituents selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea.

14. The compound of the formula I
,
in which
aa) R1and R2independently of one another denote hydrogen, C1-C7alkyl or C2-C6alkenyl; or
af) or R1or R2does
af1) C1-C6alkoxygroup; or
ah) R1and R2independently of one another denote A group-;
where A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, and the 3-10 membered ring system may be mono - or polyamidine
A1) substituents, independently selected from the group comprising halogen, =O, C1-C6alkyl and C1-C6alkoxygroup; or
A3) substituents independently chosen is different from the group including C1-C6alkylsulfonyl; or
aj) R1and R2together form a C2-C6Allenby bridge; or
ak) R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
ba) R3, R4and R7independently from each other represent
ba1) hydrogen, halogen, cyano or nitro-group; or R3, R4and R7independently of one another denote (R51)(R52)(R53Si - or (R51)(R52)(R53)Si-(C1-C6alkyl)-; where R51, R52and R53independently of one another denote C1-C6alkyl;
or R3, R4and R7independently from each other represent
ba2) C1-C6alkylsulfonyl;
or R3, R4and R7independently from each other represent
ba3) C1-C6alkyl, C2-C6alkenyl or C2-C6quinil, or C1-C6alkyl, C2-C6alkenyl or C2-C6quinil, mono - or politeley substituents, independently selected from the group comprising halogen and C1-C6alkoxygroup;
or R3, R4and R7independently from each other represent
ba5) phenyl, or benzyl or benzyl mono - or politeley substituents, independently selected from the group comprising halogen and C1-C6alkyl; or
b) R 3, R4and R7independently of one another denote A group where the group A is as defined above in section ah);
ca) R5denotes hydrogen, C2-C12alkenyl or C2-C12quinil, or denotes a C1-C12alkyl or C2-C12alkenyl mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, formyl, C2-C7alkylsulphonyl and C1-C6alkoxygroup; or
cb1) R5represents C2-C12alkylaryl or C2-C12alkoxycarbonyl; or
cc) R5means (R51)(R52)(R53Si - or (R51)(R52)(R53)Si-(C1-C12alkyl)-; or
cd) R5represents C1-C6alkyl-B-C1-C12alkyl-, where the group B denotes a-C(=NOR59)-, where R59denotes hydrogen or C1-C6alkyl; or
cf) R5refers to A-, A-(C1-C6alkyl)-, And-(C2-C6alkenyl)-, And-(C2-C6-quinil)or A-(C3-C8cycloalkyl)-; where group A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and ser is, each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine
A1) substituents, independently selected from the group comprising halogen, cyano, hydroxy-group, =O, C1-C6alkyl, C2-C6alkenyl, C1-C6halogenated, C2-C6halogenoalkanes, C1-C6alkoxygroup and C3-C6alkenylacyl; or
A2) substituents, independently selected from the group comprising (C1-C6alkyl)C(=NOR59)-, where R59denotes hydrogen or C1-C6alkyl; or
A3) substituents, independently selected from the group comprising C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl; or
A4) substituents, independently selected from the group comprising-NR57R58where R57and R58independently of one another denote hydrogen or C1-C6alkyl; or
A5) substituents, independently selected from the group comprising C2-C7alkylsulphonyl and C2-C7alkoxycarbonyl; or
A7) substituents, independently selected from the group comprising phenyl, fenoxaprop and benzyl, where phenyl, fenoxaprop and benzyl, in turn, can be mono - or polyamideimide by phenyl which various ring substituents, independently selected from the group comprising halogen;
d) R6denotes hydrogen;
and agronomically acceptable salts / N-oxides of these compounds;
in which, if R1and R2denotes methyl and each of R3, R4and R7denotes hydrogen, R5may not be 5-chloro-pyrid-3-yl;
in which, if
R1and R2independently of one another denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl, C2-C6quinil, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6halogenated, C1-C6alkyl, halogen, cyano, a nitro-group, C1-C4alkoxygroup, phenyl, phenyl substituted by halogen, (R51)(R52)(R53)Si-(C2-C6quinil)-, where R51, R52and R53independently of one another represent halogen, cyano, C1-C6alkyl, C2-C6alkenyl, C3-C8cycloalkyl, C5-C8cycloalkenyl, C2-C6quinil, C1-C6alkoxygroup, benzyl or phenyl;
R4denotes hydrogen, halogen, phenyl, imidazolyl, an amino group, a C1-C6alkoxygroup or C1-C6alkyl;
R5refers to a group A, where A denotes a 3 to 10-membered MES is carbocyclic or condensed beerbottles ring system, which may be aromatic, partially unsaturated or fully saturated, where this is a 3-10-membered ring system may be mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl, group A should be mono - or polyamidine substituents other than halogen, C1-C6of alkyl, C1-C6halogenoalkane, C1-C6alkoxygroup and C1-C6ancilliary.

15. The compound of formula I through 14, in which R1and R2independently of one another denote hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl or C3-C6cycloalkyl mono - or politeley substituents, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup; or R1and R2together form a C2-C6Allenby bridge; or R1and R2together with the connecting nitrogen atom of form pyrrolidone group.

16. The compound of formula I through 14, in which R7denotes hydrogen, C1-C6-alkyl, C1-C6Gal is penalcol, halogen or cyano.

17. The compound of formula I through 14, in which R4denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated, C3-C7cycloalkyl, halogen, cyano, C1-C6alkylsulfonyl, aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group; or aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidinyl group, each of which, in turn, is mono - or polyamidine substituents selected from the group comprising methyl and halogen; or R4denotes phenyl or phenyl which is mono - or polyamidine substituents, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup.

18. The compound of formula I through 14, in which R3denotes hydrogen, C1-C6-alkyl, C1-C6-halogenated, C2-C6alkenyl, C2-C6 quinil, C3-C7cycloalkyl, halogen, three(C1-C4alkyl)silyl, C1-C6alkylsulfonyl, phenyl, aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group; or R3means aziridinyl group, azetidinone group, pyrazolinone group, pyrazolidine group, pyrrolidone group, pyrolidine group, imidazoline group, imidazolidinyl group, triazolinone group, tetrazolium group, pieperazinove group or piperidino group, mono - or polyamidine substituents, independently selected from the group comprising methyl and halogen, or denotes phenyl, mono - or politeley substituents, independently selected from the group comprising halogen, C1-C6alkyl and C1-C6alkoxygroup.

19. The compound of formula I through 14, in which R5denotes phenyl, phenyl-C1-C6alkyl, phenyl-C3-C8cycloalkyl or phenyl-C2-C6alkenyl, or phenyl, phenyl-C1-C6alkyl, phenyl-C3-C7cycloalkyl or phenyl-C2-C6alkenyl, mono - or politeley substituents, independently is selected from the group including halogen, a cyano, a hydroxy-group, C1-C6alkyl, C1-C6halogenated, C2-C6alkenyl, C2-C6halogenoalkanes, C1-C6alkoxygroup, C3-C6alkenylacyl, C1-C6allylthiourea, C1-C6alkylsulfonyl and C1-C6alkylsulfonyl.

20. The compound of formula I through 14, in which R5denotes hydrogen, (R51)(R52)(R53)Si-(C1-C12alkyl)-, Tris1-C6alkylsilane, C3-C12alkenyl, C3-C12quinil, C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C12alkyl, C5-C10cycloalkenyl or C1-C6alkoxy-C1-C12alkyl, or R5represents C1-C12alkyl, C3-C12alkenyl, C3-C12quinil or C3-C10cycloalkyl, mono - or politeley substituents, independently selected from the group comprising halogen, a hydroxy-group, CHO and C1-C6alkoxygroup.

21. The compound of formula I through 14, in which
R1and R2independently of one another denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C 1-C6halogenated, C1-C6alkyl, halogen, cyano, a nitro-group, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen, halogen, phenyl, imidazolyl or C1-C6alkyl;
R5refers to a group A, where
A denotes a 3 to 10-membered monocyclic or condensed bicyclic ring system which may be aromatic, partially unsaturated or fully saturated and can contain 1 to 4 heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and more than 2 sulfur atoms, and she 3-10-membered ring system may be mono - or polyamidine
substituents, independently selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl.

22. The compound of formula I according to item 21, in which R3denotes hydrogen, C1-C6alkyl, halogen, cyano, a nitro-group, phenyl or phenyl containing as substituents halogen.

23. The compound of formula I through 14, in which
R1and R2independently of one another denote C1-C6Ala is l, C3-C7cycloalkyl, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6alkyl, C1-C6halogenated, halogen, cyano, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen, halogen or C1-C6alkyl;
R5denotes phenyl or C1-C6alkyl, pyridyl or phenyl or pyridyl mono - or disubstituted by substituents selected from the group comprising halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea;
R6denotes hydrogen; and
R7denotes hydrogen or C1-C6alkyl.

24. The compound of formula I according to item 23, in which
R1and R2independently of one another denote C1-C6alkyl, hydrogen or pyridine;
or R1and R2together with the connecting nitrogen atom of form pyrrolidone group;
R3denotes hydrogen, C1-C6alkyl, halogen, cyano, phenyl or phenyl containing as substituents halogen;
R4denotes hydrogen or C1-C6alkyl;
R5denotes phenyl or pyridyl, or phenyl or pyridyl mono - or disubstituted by substituents, select the tion from the group including halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxygroup and C1-C6allylthiourea.

25. The compound of the formula X
,
in which R1, R2, R3, R4, R6and R7are as defined for formula I in claim 1, and
R100denotes halogen or imidazolyl.

26. Composition intended to combat infestation by phytopathogenic microorganisms and their prevention, including the compound of the formula I according to claim 1 and an inert carrier.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and a method of producing 3,3'-[bis-(1,4-phenylene)]bis-1,3,5-dithiazinanes of formula (1): wherein diphenylenediamine (diaminodiphenylmethane, diaminodiphenyl oxide) reacts with N-tert-butyl-1,3,5-dithiazinane in the presence of a Sm(NO3)3·6H2O catalyst in an argon atmosphere in molar ratio diphenylenediamine: N-tert-butyl-1,3,5-dithiazinane:Sm(NO3)3·6H2O=1:2:(0.03-0.07) at about 20°C in an ethanol-chloroform solvent system (1:1, by volume) for 2.5-3.5 hours.

EFFECT: method of obtaining novel compounds which can be used as antimicrobial and antifungual agents, selective sorbents and extractants of precious metals, special reagents for inhibiting bacterial activity in different process media.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method for selective production of 3,3'-[bis-(1,4-phenylene)]bis-1,5,3-dithiazepinanes of formula (1) where R = 4-C6H4-CH2-C6H4-4', 4-C6H4-O-C6H4-4', 4-H3COC6H3-C6H3OCH3-4', where diphenylenediamines (diaminodiphenylmethane, diaminodiphenyl oxide, dimethoxybenzidine) react with 1-oxa-3,6-dithiacycloheptane in the presence of a Sm(NO3)3·6H2O catalyst in an argon atmosphere in molar ratio diphenylenediamine:1-oxa-3,6-dithiacycloheptane:Sm(NO3)3·6H2O=1:2:(0.03-0.07) at about 20°C in an ethanol-chloroform solvent system for 2.5-3.5 hours.

EFFECT: novel method of producing 3,3'-[bis-(1,4-phenylene)]bis-1,5,3-dithiazepinanes, which can be used as antimicrobial, antifungal and anti-inflammatory agents, sorbents and extractants of precious metals and selective complexing agents.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to benzothiazine derivatives represented by general formula (I): 0, where R1 is a hydrogen atom; C1-C6 alkyl; COR5; SO2R5; CO(CH2)mOR6; (CH2)mR6; (CH2)mCONR7R8; (CH2)nNR7R8; (CH2)nOR6; CHR7OR9; (CH2)mR10; m assumes values from 1 to 6; n assumes values from 2 to 6; R2 is phenyl; naphthyl, 1,2,3,4-tetrahydro-naphthalene, biphenyl, phenylpyridine or a benzene ring condensed with a saturated or unsaturated monocyclic heterocycle containing 5-7 atoms and consisting of carbon atoms and 1-4 heteroatoms selected from N, O or S, other than indole, R3 is methyl or ethyl; R4 and R′4 are identical or different and denote a hydrogen atom; a halogen atom; C1-C6 alkyl; NR7R8; SO2Me; as well as stereoisomers, salts and solvates thereof, for therapeutic use and which are capable of inhibiting 11β-HSD1 on an enzymatic and cellular level.

EFFECT: obtaining benzothiazine derivatives.

17 cl, 197 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, namely to method of obtaining 3,3'-[methylenebis(1,4-phenylene)]-, 3,3'-[oxybis(1,4-phenylene)]- and 3,3'-(3,3'-dimethoxybiphenyl-4, 4'-diyl)-bis-1,5,3-dithiazepinanes of general formula (1): R=4-C6H4-CH2-C6H4-4/, 4-C6H4-O-C6H4-4/, 4-H3COC6H3-C6H3OCH3-4/ which consists in the following: arylamines [diaminodiphenylmethane, diaminodiphenyloxide, dimethoxybenzidine] undergo interaction with N-tert-butyl-1,5,3-dithiazepinane in presence of catalyst Sm(NO3)3·6H2O in argon atmosphere with molar ratio arylamine:N-tert-butyl-1,5,3-dithiazeoinane: Sm(NO3)3·6H2O = 10 : 20 : (0.3-0.7) at temperature ~20°C in system of solvents ethanol-chloroform for 2.5-3.5 h.

EFFECT: increased efficiency of applying compound as antibacterial, antifungal and antiviral agents, biologically active complexants, selective sorbents and extractants of precious metals, special reagents for suppressing bacterial vital activity in different technical media.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of general formula I , where R1 is a hydrogen atom, a lower alkyl, CD3, -(CH2)n-CHO, -(CH2)n-O-lower alkyl, -(CH2)n-OH, -(CH2)n-cycloalkyl or is a heterocycloalkyl (where the heterocycloalkyl is a partially unsaturated ring containing up to 6 carbon atoms, at least one of which is substituted with O); R2 is a hydrogen atom, a halogen atom, hydroxy, lower alkyl, di-lower alkyl, -OCH2-O-lower alkyl or lower alkoxy; or the piperidine ring along with R2 forms a spiro-ring selected from 4-aza-spiro[2,5]oct-6-yl; Ar is an aryl or heteroaryl (where the heteroaryl is a cyclic aromatic hydrocarbon radical consisting of one ring and containing 6 ring atoms, and which contains at least one heteroatom selected from N), optionally having one, two or three substitutes selected from a halogen atom, lower alkyl, lower alkyl having as substitutes, a halogen atom, a lower alkoxy having as substitutes, a halogen atom, cycloalkyl, lower alkoxy, S-lower alkyl, heterocycloalkyl (where the heterocycloalkyl is a partially unsaturated ring containing up to 6 carbon atoms, at least one of which is substituted with N), or optionally having as substitutes, phenyl, optionally having R' as substitutes, and R' is a halogen atom, CF3, lower alkyl, lower alkoxy or a lower alkoxy having as substitutes, a halogen atom, or is a heteroaryl (where the heteroaryl is a cyclic aromatic hydrocarbon radical consisting of one ring and containing 6 ring atoms, and which contains at least one heteroatom selected from N and S); R is a lower alkyl, heterocycloalkyl (where the heterocycloalkyl is a partially unsaturated ring containing up to 6 carbon atoms, at least one of which is substituted with O), aryl or heteroaryl (where the heteroaryl is a cyclic aromatic hydrocarbon radical consisting of one ring and containing 6 ring atoms, and which contains at least one heteroatom selected from N), Where the aryl and heteroaryl optionally have as substitutes, one or two R'; n equals 0, 1, 2 or 3; or to a pharmaceutically acceptable acid addition salt, a racemic mixture or a corresponding enantiomer and/or optical isomer of said compound. The invention also relates to pharmaceutical compositions based on a glycine reuptake inhibitor of a compound of formula I.

EFFECT: obtaining novel compounds and a pharmaceutical composition based thereon, which can be used in medicine to treat neurological and psychoneurological disorders.

22 cl, 1 tbl, 128 ex

Cetp inhibitors // 2513107

FIELD: chemistry.

SUBSTANCE: invention relates to compound of formula I, or its pharmaceutically acceptable salt where: X stands for -O-; Z stands for -C(=O)-; Y stands for -(CRR1)-, where R1 is selected from -C1-C2alkyl; R stands for H or -C1-C5alkyl; R5 stands for H; R2 and B each is selected from A1 and A2, where one of R2 and B stands for A1, and the other from R2 and B stands for A2; where A1 has structure (a); A2 is selected from the group, which includes phenyl, pyridyl, pyrazolyl, thienyl, 1,2,4-triazolyl and imodazolyl; A3 is selected from the group including phenyl, thiazolyl and pyrazolyl; A4 is selected from the group, including phenyl, pyridyl, thiazolyl, pyrazolyl, 1,2,4-triazolyl, pyrimidinyl, piperidinyl, pyrrolidinyl and asetidinyl; A2 is optionally substituted with 1-3 substituents, independently selected from halogen atom, -OCH3 and -OCF3 and -C1-C3alkyl, optionally substituted with 1-3 halogen atoms; A3 is substituted with one A4 group and is optionally substituted with 1-2 substituents, independently selected from halogen atom, -OH, -OCH3, -OCF3 and -C1-C3alkyl, optionally substituted with 1-3 halogen atoms; A4 is optionally substituted with 1-3 substituents, independently selected from the group, which includes: (a) -C1-C5alkyl, optionally substituted with 1-3 halogen atoms and optionally substituted with group -OH, (b) -C2-C4alkenyl, optionally substituted with 1-3 halogen atoms, (c) -C(=O)C1-C2alkyl, optionally substituted with 1-3 halogen atoms and optionally substituted with one group selected from -OH, -CO2CH3, -C(=O)CH3, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (d) -C(=O)H, (e) -CO2H, (f) -CO2C1-C4alkyl, optionally substituted with one group, selected from -C(=O)C1-C2alkyl, -OH, -CO2CH3, -CO2H, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (g) -OH, (h) -S(O)xC1-C2alkyl, (i) halogen atom, (j) -CN, (k) -NO2, (l) -C(=O)NR3R4, (m) -OC1-C2alkyleneOC1-C2alkyl, (n) -OC1-C3alkyl, optionally substituted with 1-3 halogen atoms, (o) -C(=O)OC1-C2alkyl, optionally substituted with 1-3 halogen atoms and optionally substituted with one group, selected from -OH, -CO2CH3, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (q) -NR3R4 and (r) -S(O)xNR3R4, on condition that A4 stands for heterocyclic group, attached to A3 by means of ring carbon atom in A4, at least, one substituent in A4 must be selected from Re, where Re is selected from the group including: (a) -C1-C5alkyl, substituted with -OH group and optionally substituted with 1-3 halogen atoms, (b) -C2-C4alkenyl, optionally substituted with 1-3 halogen atoms, (c) -C(=O)C1-C2alkyl, optionally substituted with 1-3 halogen atoms and optionally substituted with one group selected from -OH, -CO2CH3, -C(=O)CH3, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (d) -C(=O)H, (e) -CO2H, (f) -CO2C1-C4alkyl, optionally substituted with one group, selected from -C(=O)C1-C2alkyl, -OH, -CO2CH3, -CO2H, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (g) -OH, (h) -S(O)xC1-C2alkyl, (i) -CN, (j) -NO2, (k) -C(=O)NR3R4, (l) -OC1-C2alkyleneOC1-C2alkyl, (m) -C(=O)C1-C2alkyl, optionally substituted with 1-3 halogen atoms and optionally substituted with one group, selected from -OH, -CO2CH3, -NR3R4 and -OC1-C2alkyleneOC1-C2alkyl, (n) -NR3R4(=O)OC1-C2alkyl, (o) -NR3R4 and (p) -S(O)xNR3R4; p equals 0, 1 or 2; and Ra is selected from halogen atom, -CH3, -CF3, -OCH3 and -OCF3; R3 and R4 each is independently selected from H and CH3; and x equals 0, 1 or 2.

EFFECT: formula (I) compound is applied for medication, which possesses properties of CETP inhibitor, for increase of HDL-C and for reduction of LDL-C Technical result is compounds, inhibiting cholesterol ether transferring protein (CETP).

10 cl, 140 ex

FIELD: chemistry.

SUBSTANCE: invention relates to triazole compounds which are represented by specific chemical formulae and which can be used for preventing or treating diseases in which 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) participates, particularly dementia. It was found that the triazole derivative, in which one of 3rd and 5th positions of the triazole ring accommodates a (di)alkyl methyl or cycloalkyl, each substituted, -O-aryl or heterocyclic group, each of which can be substituted, or (lower alkylene)cycloalkyl, and the other position accommodates an aryl, heterocyclic or cycloalkyl group, each of which can be substituted, or a pharmaceutically acceptable salt thereof, has powerful inhibiting action on 11β-HSD1.

EFFECT: improved properties of the derivatives.

8 cl, 141 tbl, 89 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I) , where is a substituted 5-member heteroaryl ring selected from thienyl, thiazolyl, oxazolyl, pyrrolyl, imidazolyl or pyrazolyl, W is selected from a group comprising N and -C=; M is selected from a group comprising -C(O)N(R1)OR2, -CXCONR1R2 and -C(O)OR1, or M is -C1-C2alkyl-C(O)N(R1)OR2, wherein is , R1 and R2 are independently selected from a group comprising -H, C1-C3-alkyl, C6-aryl, and C1-C3-alkyl-C6-aryl; R is selected from a group comprising H, C1-C3alkyl, halogen, NR1R2, -OR1 and C6aryl; n is an integer from 0 to 1; L and Y are as indicated in the claim; and to compounds of formula (II) , where L2 is selected from a group comprising H, - C0-C3alkyl- C6aryl, -C0-C3alkyl-heteroaryl, where the heteroaryl is pyridyl; -C1-C6alkyl, Y and M are the same as for compounds of formula (I). The invention also relates to a pharmaceutical composition based on compounds (I) and (II), having inhibiting action on histone deacetylase (HDAC), a method of inhibiting and a method of treating a disease which is sensitive to the HDAC inhibitor.

EFFECT: compounds of formula I and II as histone deacetylase inhibitors.

18 cl, 18 dwg, 10 tbl, 19 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to compounds being aspartyl protease inhibitors applicable for treating cardiovascular, neurodegenerative disorders and fungal infection of formula , wherein W represents -C(=O)-; X represents -NH-; U represents -C(R6)(R7)-; R1 represents methyl, R2, R3 and R6 represent H, R4 and R7 represent optionally substituted phenyl, as well as tautomers and pharmaceutically acceptable salts thereof.

EFFECT: there are presented new effective aspartyl protease inhibitors specified in rennin, cathepsin D, BACE-1, for treating cardiovascular diseases, cognitive and neurodegenerative diseases, as well as fungal infections.

67 cl, 1 tbl, 4393 ex

FIELD: chemistry.

SUBSTANCE: invention describes compounds of formula I , where R1 and R2 independently denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl, C2-C6alkynyl, hydrogen or pyridine; or R1 and R2 together with a nitrogen atom which binds them form a pyrroline group; R3 denotes hydrogen, C1-C6halogenalkyl, C1-C6alkyl, halogen, cyano group, nitro group, C1-C4alkoxy group, phenyl, halogen-substituted phenyl, (R51)(R52)(R53)Si-(C2-C6alkynyl)-, where R51, R52, R53 independently denote halogen, cyano group, C1-C6alkyl, C2-C6alkenyl, C3-C8cycloalkyl, C5-C8cycloalkenyl, C2-C6alkynyl, C1-C6alkoxy group, benzyl or phenyl; R4 denotes hydrogen, halogen, phenyl, imidazolyl, amino group, C1-C6alkoxy group or C1-C6alkyl; R5 denotes C1-C12alkyl or a group A, where A denotes a 3-10-member monocyclic or condensed bicyclic ring system which can be aromatic, partially unsaturated or completely saturated, where said 3-10-member ring system can be mono- or polysubstituted with substitutes independently selected from a group comprising halogen, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy group and C1-C6alkylthio group; R6 denotes hydrogen; and R7 denotes hydrogen or C1-C6alkyl and agronomically acceptable salts/metal complexes/metalloid complexes/isomers/structural isomers/stereoisomers. The invention also relates to methods of controlling infection of useful plants by phytopathogenic microorganisms by applying a compound of formula I onto the plants, a part thereof or place where said plants grow, as well as a composition for controlling infection by phytopathogenic microorganisms.

EFFECT: novel compounds which are suitable for use as microbiocides are obtained and described.

7 cl, 48 ex, 151 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formulas I, II, III, IV, V, VIII or to their pharmaceutically acceptable salts, wherein: Z represents , or phenyl; D represents or ; X represents N(R9), O, S, S(=O) or S(O)2; each Y independently represents O or S; G represents or ; the other radical values are described in the patent claim. The invention also refers to pharmaceutical compositions based on the above compounds.

EFFECT: there are prepared new compounds and based compositions which can find application for treating malaria or eliminating or inhibiting the growth of Plasmodium species.

30 cl, 3 tbl, 23 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I) , where is a substituted 5-member heteroaryl ring selected from thienyl, thiazolyl, oxazolyl, pyrrolyl, imidazolyl or pyrazolyl, W is selected from a group comprising N and -C=; M is selected from a group comprising -C(O)N(R1)OR2, -CXCONR1R2 and -C(O)OR1, or M is -C1-C2alkyl-C(O)N(R1)OR2, wherein is , R1 and R2 are independently selected from a group comprising -H, C1-C3-alkyl, C6-aryl, and C1-C3-alkyl-C6-aryl; R is selected from a group comprising H, C1-C3alkyl, halogen, NR1R2, -OR1 and C6aryl; n is an integer from 0 to 1; L and Y are as indicated in the claim; and to compounds of formula (II) , where L2 is selected from a group comprising H, - C0-C3alkyl- C6aryl, -C0-C3alkyl-heteroaryl, where the heteroaryl is pyridyl; -C1-C6alkyl, Y and M are the same as for compounds of formula (I). The invention also relates to a pharmaceutical composition based on compounds (I) and (II), having inhibiting action on histone deacetylase (HDAC), a method of inhibiting and a method of treating a disease which is sensitive to the HDAC inhibitor.

EFFECT: compounds of formula I and II as histone deacetylase inhibitors.

18 cl, 18 dwg, 10 tbl, 19 ex

FIELD: chemistry.

SUBSTANCE: invention describes compounds of formula I , where R1 and R2 independently denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl, C2-C6alkynyl, hydrogen or pyridine; or R1 and R2 together with a nitrogen atom which binds them form a pyrroline group; R3 denotes hydrogen, C1-C6halogenalkyl, C1-C6alkyl, halogen, cyano group, nitro group, C1-C4alkoxy group, phenyl, halogen-substituted phenyl, (R51)(R52)(R53)Si-(C2-C6alkynyl)-, where R51, R52, R53 independently denote halogen, cyano group, C1-C6alkyl, C2-C6alkenyl, C3-C8cycloalkyl, C5-C8cycloalkenyl, C2-C6alkynyl, C1-C6alkoxy group, benzyl or phenyl; R4 denotes hydrogen, halogen, phenyl, imidazolyl, amino group, C1-C6alkoxy group or C1-C6alkyl; R5 denotes C1-C12alkyl or a group A, where A denotes a 3-10-member monocyclic or condensed bicyclic ring system which can be aromatic, partially unsaturated or completely saturated, where said 3-10-member ring system can be mono- or polysubstituted with substitutes independently selected from a group comprising halogen, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy group and C1-C6alkylthio group; R6 denotes hydrogen; and R7 denotes hydrogen or C1-C6alkyl and agronomically acceptable salts/metal complexes/metalloid complexes/isomers/structural isomers/stereoisomers. The invention also relates to methods of controlling infection of useful plants by phytopathogenic microorganisms by applying a compound of formula I onto the plants, a part thereof or place where said plants grow, as well as a composition for controlling infection by phytopathogenic microorganisms.

EFFECT: novel compounds which are suitable for use as microbiocides are obtained and described.

7 cl, 48 ex, 151 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formula

and

possessing the protein kinase inhibitor property, their pharmaceutically acceptable salts, solvates and hydrates, as well as to the use thereof and a based pharmaceutical composition. In general formula (1) X1 represents N, CRt1; X2 represents N, CRt2, X3 represents N, CRt3, X4 represents N, CH and wherein X1, X2, X3 and X4 are independently specified; Rt1 represents -H, halogen, -COOH, -CH3, -CH2CH3, -OH, -OCH3, -OCH2CH3, -CN, -CH3OH; Rt2 represents -H, halogen, -CH3, -CH2CH3, -OH, -OCH3, -OCH2CH3, -CN, CH2OH, -NH2; Rt3 represents -H, -S(O)rR4, halogen, -CN, -COOH, -CONH2, -COOCH3, -COOCH2CH3; the cycle A represents phenyl or a 6-member heteroaryl cycle, wherein heteroaryl contains 1-2 heteroatoms specified in N optionally substituted by 1-4 groups R'; the cycle B represents phenyl or a 5- or 6-member heteroaryl cycle, wherein heteroaryl contains 1-2 heteroatoms specified in N, S optionally substituted by 1-5 groups Rb; Ra and Rb are independently specified and represent -H, halogen, -CN, -R6, -OR4, -NR4R5, -C(O)YR4, -S(O)rR4, -SO2NR4R5, -NR4SO2NR4R5 wherein Y is independently specified and represents a chemical bond, -O-, -S-, -NR3-; L1 represents NR3C(O) or C(O)NR3; R3, R4 and R5 are independently specified and represent H, C1-C6-alkyl, and also the group NR4 R5 may represent a 5- or 6-member saturated or aromatic cycle; in each case R6 is independently specified and represents C1-C6-alkyl optionally substituted by C1-C6- alkyl or 5-6 merous heterocyclyl which may be substituted by C1-C6-alkyl; r is equal to 0; In general formula (II) Z represents CH; X, represents CRt1; X2 represents CRt2, X3 represents CRt3 X4 represents CH and wherein X1, X2, X3 and X4 are independently specified; Rt1 represents -H; Rt2 represents -H, -F; Rt3 represents -H, -F; the cycle A represents phenyl or 6-member heteroaryl cycle wherein heteroaryl contains 1-2 heteroatoms specified in N optionally substituted by 1-4 groups R3; the cycle B represents phenyl or a 5- or 6-member heteroaryl cycle wherein heteroaryl contains 1-2 heteroatoms specified in N, S optionally substituted by 1-5 groups Rb, Ra and Rb are independently specified and represent -H, halogen, -CN, -R6, -OR4, -NR4R5, -C(O)YR4, -S(O)rR4, -SO2NR4R5 wherein Y is independently specified and represents a chemical bond, -NR3-; L represents NR3C(O) or C(O)NR3; R4 and R5 are independently specified and represent H, C1-C6-alkyl, also the group NR4R3 may represent a 6-member saturated cycle; in each case R6 is independently specified and represents, C1-C6-alkyl optionally substituted by C1-C6-alkyl or 5-6 member heterocyclyl which may be substituted by C1-C6-alkyl; r is equal to 0; m is equal to 1; p is equal to 1.2.

EFFECT: preparing the compounds possessing the protein kinase inhibitor property.

16 cl, 5 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: there are described new benzimidazole derivatives of general formula I wherein: R1 = CN, halogen or C(=O)CH3; R2 means methyl or H; R3=H or halogen; R4 and R5 independently mean methyl or ethyl, or R4 and R5 together with a carbon atom whereto attached form C3-6cycloalkyl or 5-6-member heterocycloalkyl; R6 and R7 independently mean H, halogen, methyl or ethyl; or their pharmaceutically acceptable salts, pharmaceutical compositions containing these compounds, and their application in therapy.

EFFECT: compounds may be used in treating osteoarthritis, chronic tendinitis, pelvic pain and peripheral neuropathy, gastroesophageal reflux disease, irritable bowel syndrome and overactive bladder.

39 cl, 34 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel azoles of general formula 1A and 1B and pharmaceutically acceptable salts thereof, having activity on hepatitis C and hepatitis GBV-C virus. Said compounds have NS5A viral protein ligand properties and can be used as active components for a pharmaceutical composition and a medicinal agent for treating diseases caused by said viruses. In general formula 1A and 1B, the solid lines accompanied by dotted lines denote a single or double bond, wherein if one of them is a single bond, the other is a double bond; X and Y optionally assume different values and denote a nitrogen, oxygen or sulphur atom or a NH group; R1 and R2 optionally denote identical radicals 2.1-2.20, in which the asterisk (*) indicates site of the bond to azole fragments. Said fragments and values of A and B are given in the claim.

EFFECT: more value of the compounds.

10 cl, 1 tbl, 16 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: this invention relates to new compounds with formula (I) possessing the properties of mGLuR2 antagonists, to their obtainment methods, their application for production of medicines for prevention and treatment of disorders wherein mGLuR2 plays the activation role (in particular - central nervous system disorders). In formula (I) either any of X and Y represents N while the other represents CH or each of X and Y represents N; A represents aryl representing phenyl or 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur, the heteroaryl selected from among amidazolyl, [1,2,4] oxadiazolyl, pyrrolyl, 1H-pyrazolyl, pyridinyl, [1,2,4] triazolyl, tiazolyl and pyrimidinyl, each of them substitutable by C1-6-alkyl; B represents H, cyano or represents a possibly substituted aryl selected from among phenyl or possibly substituted by 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur where the substitutes are selected from the group consisting of nitro, C1-6-alkyl, possibly substituted hydroxy, NRaRb where Ra and Rb independently represent H, C1-6-alkyl etc. R1 represents H, a halogen atom, C1-6-alkyl, possibly substituted hydroxy, C1-6-alcoxy, C1-6-halogenoalkyl, C3-6-cycloalkyl represents H cyano, a halogen atom, C1-6-halogenoalkyl, C1-6-alcoxy, C1-6-halogenoalcoxi-, C1-6-alkyl or C3-6-cycloalkyl R3 represents a halogen atom, H, C1-6-alcoxy, C1-6-halogenoalkyl, C1-6-alkyl, C3-6-cycloalkyl, C1-6-halogenoalcoxy R4 reprsents H or halogeno.

EFFECT: creation of new compounds of formula (I) possessing mGLuR2 antagonist properties.

104 cl, 465 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel benzimidazole derivatives of formula

and pharmaceutically acceptable salts and esters thereof, where R1 denotes C1-10alkyl, lower alkoxy group-lower alkyl, lower alkoxy group-carbonyl-lower alkyl, C3-6cycloalkyl, C3-6cycloalkyl-lower alkyl, phenyl, phenyl-lower alkyl, di(phenyl)-lower alkyl, heterocyclyl, such as piperidinyl, tetrahydropyranyl, 2-oxo-pyrrolidinyl-lower alkyl, where the cycloalkyl, phenyl or heterocyclyl group is optionally substituted with 1-2 substitutes independently selected from a group comprising lower alkyl, lower alkoxy group, lower alkoxy group-carbonyl, morpholinyl, formylamino group and halogen; R2 denotes hydrogen or lower alkyl; R3 denotes lower alkyl, C3-6cycloalkyl, partially unsaturated cyclohexyl, phenyl, phenyl-lower alkyl, pyridinyl, benzodioxolyl, tetrahydropyranyl, where the phenyl group is optionally substituted with 1-2 substitutes independently selected from a group comprising a halogen, lower alkyl, lower alkoxy group, fluoro-lower alkyl, fluoro-lower alkoxy group, N(lower alkyl)2; R4 denotes: a) heteroaryl which is an aromatic 5-6-member monocyclic ring or a 9-10-member bicyclic ring containing 1 or 2 heteroatoms selected from nitrogen, oxygen and/or sulphur, which is optionally substituted with 1-2 substitutes independently selected from a group comprising lower alkyl, phenyl, lower alkoxy group, -N(lower alkyl)2, oxo group, NH2, halogen, cyano group and morpholinyl; b) unsubstituted naphthyl, naphthyl or phenyl, which are substituted with 1-3 substitutes independently selected from a group comprising halogen, hydroxy group, NH2, CN, hydroxy-lower alkyl, lower alkoxy group, lower alkyl-carbonyl, lower alkoxy group-carbonyl, sulphamoyl, di-lower alkyl-sulphamoyl, lower alkyl-sulphonyl, thiophenyl, pyrazolyl, thiadiazolyl, imidazolyl, triazolyl, tetrazolyl, 2-oxopyrrolidinyl, lower alkyl, fluoro-lower alkyl, fluoro-lower alkoxy group, N(lower alkyl)2, carbamoyl, lower alkenyl, benzoyl, phenoxy group and phenyl which is optionally substituted with 1-2 substitutes independently selected from halogen and fluoro-lower alkyl; or c) if R3 denotes cycloalkyl and R1 denotes cycloalkyl, then R4 can also denote phenyl; R5, R6, R7 and R8 independently denote H, halogen, lower alkoxy group or lower alkyl, or R6 and R7, which are bonded to each other, form a 6-member aromatic carbocyclic ring together with carbon atoms to which they are bonded; provided that the compound of formula (I) is not selected from a group comprising butylamide 2-[2-(2-chlorophenyl)benzoimidazol-1-yl]-4-methylpentanoic acid and 2-(2-benzo[1,3]dioxol-5-ylbenzoimidazol-1-yl)-N-benzyl-butyric acid amide. The invention also relates to a pharmaceutical composition based on the formula I compound.

EFFECT: novel benzimidazole derivatives which are useful as farnesoid X receptor antagonists are obtained.

30 cl, 379 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to organic electroluminescent devices based on compounds of formula

where Y, Z is selected from N, P, P=O, C=O, O, S, S=O and SO2; Ar1, Ar2, Ar3 are selected from benzene, naphthaline, anthracene, phenanthrene, pyridine, pyrene or thiophene, optionally substituted with R1; Ar4, Ar5, Ar6, Ar7 are selected from benzene, naphthaline, anthracene, phenanthrene, pyridine, pyrene, thiophene, triphenylamine, diphenyl-1-naphthylamine, diphenyl-2-naphthylamine, phenyldi(1-naphthyl)amine, phenyldi(2-naphthyl)amine or spirobifluorene, optionally substituted with R1; E is a single bond, N(R1), O, S or C(R1)2; R1 denotes H, F, CN, alkyl, where the CH2 can be substituted with -R2C=CR2 -, -C=C-, -O- or -S-, and H can be substituted with F, optionally substituted aryl or heteroaryl, where R1 can form a ring with each other; R2 denotes H, aliphatic or aromatic hydrocarbon; X1, X4, X2, X3 are selected from C(R1)2, C=O, C=NR1, O, S, S=O, SO2, N(R1), P(R1), P(=O)R1, C(R1)2-C(R1)2, C(R1)2-C(R1)2-C(R1)2, C(R1)2-O and C(R1)2-O-C(R1)2; n, o, p, q, r and t are equal to 0 or 1; s = 1.

EFFECT: obtaining novel compounds - emission layer dopants, and novel electroluminescent devices based on said compounds which emit a blue colour.

18 cl, 91 ex, 6 tbl

Organic compounds // 2411239

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula I, in which R1 denotes alkyl or cycloalkyl; R2 denotes phenyl-C1-C7-alkyl, di-(phenyl)- C1-C7-alkyl, naphthyl- C1-C7-alkyl, phenyl, naphthyl, pyridyl-C1-C7-alkyl, indolyl- C1-C7-alkyl, 1H-indazolyl- C1-C7-alkyl, quinolyl C1-C7-alkyl, isoquinolyl- C1-C7-alkyl, 1,2,3,4-tetrahydro-1,4-benzoxazinyl- C1-C7-alkyl, 2H-1,4-benzoxazin-3(4H)-onyl-C1-C7-alkyl, 9-xanthenyl-C1-C7-alkyl, 1-benzothiophenyl-C1-C7-alkyl, pyridyl, indolyl, 1H-indazolyl, quinolyl, isoquinolyl, 1,2,3,4-tetrahydro-1,4-benzoxazonyl, 2H-1,4-benzoxazin-3(4H)-onyl, 9-xanthenyl, 1-benzothiophenyl, 4H-benzo[1,4]thiazin-3-only, 3,4-dihydro-1H-quinolin-2-onyl or 3H-benzoxazol-2-onyl, where each phenyl, naphthyl, pyridyl, indolyl, 1H-indazolyl, quinolyl, isoquinolyl, 1,2,3,4-tetrahydro-1,4-benzoxazonyl, 2H-1,4-benzoxazin-3(4H)-onyl, 1-benzothiophenyl, 4H-benzo[1,4]thiazin-3-only, 3,4-dihydro-1H-quinolin-2-onyl or 3H-benzoxazol-2-onyl are unsubstituted or contain one or up to 3 substitutes independently selected from a group comprising C1-C7-alkyl, hydroxy-C1-C7-alkyl, C1-C7-alkoxy- C1-C7-alkyl, C1-C7-alkoxy- C1-C7-alkoxy-C1-C7-alkoxy- C1-C7-alkyl, C1-C7-alkanoyloxy- C1-C7-alkyl, amino- C1-C7-alkyl, C1-C7-alkoxy- C1-C7-alkylamino- C1-C7-alkyl, C1-C7-alkanoylamino- C1-C7-alkyl, C1-C7-alkylsulphonylamino- C1-C7-alkyl, carboxy- C1-C7-alkyl, C1-C7-alkoxycarbonyl- C1-C7-alkyl, halogen, hydroxy group, C1-C7-alkoxy group, C1-C7-alkoxy- C1-C7-alkoxy group, amino- C1-C7-alkoxy group, N-C1-C7-alkanoylamino-C1-C7-alkoxy group, carbamoyl- C1-C7-alkoxy group, N-C1-C7-alkylcarbamoyl-C1-C7-alkoxy group, C1-C7-alkanoyl, C1-C7-alkoxy-C1-C7-alkanoyl, C1-C7-alkoxy- C1-C7-alkanoyl, carboxyl, carbamoyl and N-C1-C7-alkoxy-C1-C7-alkylcarbamoyl; W denotes a fragment selected from residues of formulae IA, IB and IC, where () indicates the position in which the fragment W is bonded to the carbon atom in position 4 of the piperidine ring in formula I, and where X1, X2, X3, X4 and X5 are independently selected from a group containing carbon and oxygen, where X4 in formula IB and X1 in formula IC can assume one of these values or can be additionally selected from a group comprising S and O, where carbon and nitrogen ring atoms can include a number of hydrogen atoms or substitutes R3 or R4 if contained, taking into account limitations given below, required to bring the number of bonds of the carbon ring atom to 4 and 3 for the nitrogen ring atom; provided that in formula IA at least 2, preferably at least 3 of the atoms X1-X5 denote carbon and in formulae IB and IC at least one of X1-X4 denotes carbon, preferably 2 of the atoms X1-X4 denote carbon; y equals 0 or 1; z equals 0 or 1; R3, which can be bonded with any of the atoms X1, X2, X3 and X4, denotes hydrogen or a C1-C7-alkyloxy-C1-C7-alkyloxy group, phenyloxy-C1-C7-alkyl, phenyl, pyridinyl, phenyl- C1-C7-alkoxy group, phenyloxy group, phenyloxy-C1-C7-alkoxy group, pyridyl-C1-C7-alkoxy group, tetrahydropyranyloxy group, 2H,3H-1,4-benzodioxynyl-C1-C7-alkoxy group, phenylaminocarbonyl or phenylcarbonylamino group, where each phenyl or pyridyl is unsubstituted or contains one or up to 3 substitutes, preferably 1 or 2 substitutes independently selected from a group comprising C1-C7-alkyl, hydroxy group, C1-C7-alkoxy group, phenyl-C1-C7-alkoxy group, where phenyl is unsubstituted or substituted with a C1-C7-alkoxy group and/or halogen; carboxy- C1-C7-alkyloxy group, N-mono- or N,N-di-(C1-C7-alkyl)aminocarbonyl-C1-C7-alkyloxy group, halogen, amino group, N-mono- or N,N-di-(C1-C7-alkyl)amino group, C1-C7-alkanoylamino group, morpholino-C1-C7-alkoxy group, thiomorpholino-C1-C7-alkoxy group, pyridyl-C1-C7-alkoxy group, pyrazolyl, 4- C1-C7-alkylpiperidin-1-yl, tetrazolyl, carboxyl, N-mono- or N,N-di-(C1-C7-alkylamino)carbonyl or cyano group; or denotes 2-oxo-3-phenyltetrahydropyrazolidin-1-yl, oxetidin-3-yl-C1-C7-alkyloxy group, 3-C1-C7-alkyloxetidin-3-yl- C1-C7-alkyloxy group or 2-oxotetrahydrofuran-4-yl- C1-C7-alkyloxy group; provided that if R3 denotes hydrogen, then y and z are equal to 0; R4, if contained, denotes a hydroxy group, halogen or C1-C7-alkoxy group; T denotes carbonyl; and R11 denotes hydrogen, or pharmaceutically acceptable salts thereof. The invention also relates to use of formula I compounds, a pharmaceutical composition, as well as a method of treating diseases.

EFFECT: obtaining novel biologically active compounds having activity towards rennin.

11 cl, 338 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention describes compounds of formula I , where R1 and R2 independently denote hydrogen, C3-C7cycloalkyl, C1-C6alkyl, C2-C6alkynyl, hydrogen or pyridine; or R1 and R2 together with a nitrogen atom which binds them form a pyrroline group; R3 denotes hydrogen, C1-C6halogenalkyl, C1-C6alkyl, halogen, cyano group, nitro group, C1-C4alkoxy group, phenyl, halogen-substituted phenyl, (R51)(R52)(R53)Si-(C2-C6alkynyl)-, where R51, R52, R53 independently denote halogen, cyano group, C1-C6alkyl, C2-C6alkenyl, C3-C8cycloalkyl, C5-C8cycloalkenyl, C2-C6alkynyl, C1-C6alkoxy group, benzyl or phenyl; R4 denotes hydrogen, halogen, phenyl, imidazolyl, amino group, C1-C6alkoxy group or C1-C6alkyl; R5 denotes C1-C12alkyl or a group A, where A denotes a 3-10-member monocyclic or condensed bicyclic ring system which can be aromatic, partially unsaturated or completely saturated, where said 3-10-member ring system can be mono- or polysubstituted with substitutes independently selected from a group comprising halogen, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy group and C1-C6alkylthio group; R6 denotes hydrogen; and R7 denotes hydrogen or C1-C6alkyl and agronomically acceptable salts/metal complexes/metalloid complexes/isomers/structural isomers/stereoisomers. The invention also relates to methods of controlling infection of useful plants by phytopathogenic microorganisms by applying a compound of formula I onto the plants, a part thereof or place where said plants grow, as well as a composition for controlling infection by phytopathogenic microorganisms.

EFFECT: novel compounds which are suitable for use as microbiocides are obtained and described.

7 cl, 48 ex, 151 tbl

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