RU99119226A - 2,4-DIAMINO-1,3,5-TRIAZINES, METHOD FOR THEIR PRODUCTION AND THEIR APPLICATION AS HERBICIDES AND PLANT GROWTH REGULATORS - Google Patents
2,4-DIAMINO-1,3,5-TRIAZINES, METHOD FOR THEIR PRODUCTION AND THEIR APPLICATION AS HERBICIDES AND PLANT GROWTH REGULATORSInfo
- Publication number
- RU99119226A RU99119226A RU99119226/04A RU99119226A RU99119226A RU 99119226 A RU99119226 A RU 99119226A RU 99119226/04 A RU99119226/04 A RU 99119226/04A RU 99119226 A RU99119226 A RU 99119226A RU 99119226 A RU99119226 A RU 99119226A
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- RU
- Russia
- Prior art keywords
- carbon atoms
- group
- alkyl
- residues
- alkoxy
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims 2
- 239000005648 plant growth regulator Substances 0.000 title 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 597
- 125000000217 alkyl group Chemical group 0.000 claims 185
- 125000003545 alkoxy group Chemical group 0.000 claims 73
- -1 cyano, nitro, thiocyanato Chemical group 0.000 claims 44
- 229910052736 halogen Inorganic materials 0.000 claims 43
- 150000002367 halogens Chemical class 0.000 claims 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 41
- 125000004429 atoms Chemical group 0.000 claims 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 229910052757 nitrogen Inorganic materials 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 30
- 125000001188 haloalkyl group Chemical group 0.000 claims 27
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 27
- 229910052760 oxygen Inorganic materials 0.000 claims 27
- 239000001301 oxygen Substances 0.000 claims 27
- 125000005842 heteroatoms Chemical group 0.000 claims 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims 25
- 125000004414 alkyl thio group Chemical group 0.000 claims 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000003342 alkenyl group Chemical group 0.000 claims 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 19
- 125000000304 alkynyl group Chemical group 0.000 claims 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- 125000004122 cyclic group Chemical group 0.000 claims 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 16
- 125000001589 carboacyl group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 239000011780 sodium chloride Substances 0.000 claims 13
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 150000002829 nitrogen Chemical group 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 8
- 125000002837 carbocyclic group Chemical group 0.000 claims 8
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims 8
- 125000000232 haloalkynyl group Chemical group 0.000 claims 8
- 241000196324 Embryophyta Species 0.000 claims 7
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 6
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 6
- 125000002015 acyclic group Chemical group 0.000 claims 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 5
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 230000001105 regulatory Effects 0.000 claims 3
- 125000004354 sulfur functional group Chemical group 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive Effects 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 2
- 230000002363 herbicidal Effects 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 241000208202 Linaceae Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N diguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 1
- 125000006782 halocycloalkylcarbonyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Claims (10)
где R1 означает алкил с 1 - 6 атомами углерода, незамещенный или замещенный одним или несколькими остатками из группы, включающей галоген, гидроксил, циано, нитро, тиоцианато, алкоксил с 1-4 атомами углерода, алкилтио с 1 - 4 атомами углерода, алкилсульфинил с 1 - 4 атомами углерода, алкилсульфонил с 1 - 4 атомами углерода, алкенил с 2 - 4 атомами углерода, алкинил с 2 - 4 атомами углерода, и незамещенным или замещенным фенилом, или незамещенный или замещенный фенил,
R2 и R3 независимо друг от друга означают водород, амино, алкиламино с 1 - 6 атомами углерода или диалкиламино с 1 - 6 атомами углерода в алкильной части, углеводородный остаток или кислородсодержащий углеводородный остаток, каждый с 1 - 10 атомами углерода, предпочтительно с 1 - 6 атомами углерода, или гетероциклический остаток, кислородсодержащий гетероциклический остаток или аминосодержащий гетероциклический остаток, каждый с 3 - 9 атомами кольца и 1 - 3 гетероатомами из группы, включающей азот, кислород и серу, причем каждый из последних пяти остатков незамещен или замещен, или ациловый остаток, или
R2 и R3 вместе с атомом азота группы NR2R3 означают 3 - 6-членный гетероциклический остаток с 1 - 4 гетероатомами, причем кроме атома азота имеющиеся при необходимости дальнейшие гетероатомы выбраны из группы азота, кислорода и серы, и остаток незамещен или замещен;
R4 - водород, аминогруппу, алкиламиногруппу с 1 - 6 атомами углерода, диалкиламиногруппу с 1 - 6 атомами углерода в алкильной части, углеводородный остаток или кислородсодержащий углеводородный остаток, каждый с 1 - 10 атомами углерода, предпочтительно с 1 - 6 атомами углерода, или гетероциклический остаток, кислородсодержащий гетероциклический остаток или аминосодержащий гетероциклический остаток, каждый с 3 - 9 атомами кольца и 1 - 3 гетероатомами из группы, включающей азот, кислород и серу, причем каждый из последних пяти остатков незамещен или замещен, или ациловый остаток;
R5 и R6 независимо друг от друга означают галоген, нитро, циано, тио-цианато или остаток формулы-Х1-А1, где -X1 означает прямую связь или дивалентную группы формулы -О-, -S(О)p-О-, -О-S(О)p-, -СО-, -О-СО-, -СО-О-, -NR'-, -O-NR'-, -NR'-O-, -NR'-CO- или -CO-NR'-, причем в формулах р означает 0, 1 или 2, R' -водород, алкил с 1 - 6 атомами углерода, фенил, бензил, циклоалкил с 3 - 6 атомами углерода или алканоил с 1 - 6 атомами углерода, и А1 - водород или углеводородный остаток или гетероциклический остаток, причем каждый из последних двух остатков незамещен или замещен, или
R5 и R6 вместе означают алкиленовую цепь с 2 - 4 атомами углерода, незамещенную или замещенную одним или несколькими остатками из группы, включающей галоген, алкил с 1 - 4 атомами углерода и оксогруппу;
R7 независимо от других остатков R7 означает галоген, нитро, циано, тиоцианато или остаток формулы -Х2А2, где X2 означает прямую связь или дивалентную группу формулы -О-, -S(О)q-О-, -О-S(О)q-, -СО-, -О-СО-, -СО-О-, -NR"-, -О-NR"-, -NR"-О-, -NR"-CO- или -CO-NR"-, причем в формулах q означает 0, 1 или 2, R" - водород, алкил с 1 - 6 атомами углерода, фенил, циклоалкил с 3 - 6 атомами углерода, и
А1 - водород или углеводородный остаток или гетероциклический остаток, причем каждый из последних двух остатков незамещен или замещен, или два соседних радикала R7 вместе означают приконденсированный цикл с 4 - 6 атомами кольца, который является карбоциклическим или содержит гетероатомы из группы, включающей кислород, серу и азот, и который незамещен или замещен одним или несколькими остатками из группы, включающей галоген, алкил с 1 - 4 атомами углерода и кислород,
Х означает группы формулы -О-, S(О)r-, -NR*- или -N(O)-, причем r означает 0, 1 или 2, R* - водород или алкил с 1 - 4 атомами углерода, и
n - 0, 1, 2, 3, 4 или 5,
за исключением соединений формулы (I) и их солей,
а) где R1 - 1-галогенэтил, 1-галоген-1-метил-этил или 1-галоген-1-метил-пропил, R2, R3, R4, R6 означают каждый водород, R5 - метил, R7 - алкил с 1 - 4 атомами углерода, ОСН3 или фтор, причем в случае если n равняется 2, оба радикала R7 имеют одинаковое значение, n - число 0, 1 или 2, Х - атом кислорода, а также
б) где R1 - алкил с 1 - 10 атомами углерода, незамещенный или замещенный 1 - 4 заместителями из группы, включающей алкоксил с 1 - 4 атомами углерода и гидроксил, R2, R3, R4, R6 означают каждый водород, R5 - метил, R7 независимо от других радикалов R7 означает алкил с 1 - 4 атомами углерода, ОСН3 или галоген, n - число 0, 1, 2, 3 или 4, и X - атом кислорода.1. The compounds of formula (I) and their salts
where R 1 means alkyl with 1 to 6 carbon atoms, unsubstituted or substituted by one or more residues from the group including halogen, hydroxyl, cyano, nitro, thiocyanato, alkoxy with 1-4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, and unsubstituted or substituted phenyl, or unsubstituted or substituted phenyl,
R 2 and R 3 independently of one another denote hydrogen, amino, alkylamino with 1 to 6 carbon atoms or dialkylamino with 1 to 6 carbon atoms in the alkyl part, a hydrocarbon residue or an oxygen-containing hydrocarbon residue, each with 1 to 10 carbon atoms, preferably with 1 to 6 carbon atoms, or a heterocyclic residue, an oxygen-containing heterocyclic residue or an amino-containing heterocyclic residue, each with 3 to 9 ring atoms and 1 to 3 heteroatoms from the group comprising nitrogen, oxygen and sulfur, each of the last five the tissue is unsubstituted or substituted, or the acyl residue, or
R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 means a 3-6-membered heterocyclic residue with 1-4 heteroatoms, and in addition to the nitrogen atom, further heteroatoms are optionally selected from the group of nitrogen, oxygen and sulfur, and the residue is unsubstituted or substituted;
R 4 is hydrogen, an amino group, an alkylamino group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in the alkyl part, a hydrocarbon residue or an oxygen-containing hydrocarbon residue, each with 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or a heterocyclic residue, an oxygen-containing heterocyclic residue or an amino-containing heterocyclic residue, each with 3 to 9 ring atoms and 1 to 3 heteroatoms from the group including nitrogen, oxygen and sulfur, and each of the last five residues is unsubstituted or displacements or acyl residue;
R 5 and R 6 independently of one another denote halogen, nitro, cyano, thio-cyanato or a residue of the formula-X 1 -A 1 , where -X 1 means a direct bond or divalently groups of the formula -O-, -S (O) p -O-, -O-S (O) p -, -CO-, -O-CO-, -CO-O-, -NR'-, -O-NR'-, -NR'-O-, - NR'-CO- or -CO-NR'-, and in formulas p represents 0, 1 or 2, R'-hydrogen, alkyl with 1-6 carbon atoms, phenyl, benzyl, cycloalkyl with 3-6 carbon atoms or alkanoyl with 1 to 6 carbon atoms, and A 1 is hydrogen or a hydrocarbon residue or a heterocyclic residue, each of the last two residues being unsubstituted or substituted, or
R 5 and R 6 together represent an alkylene chain with 2 to 4 carbon atoms, unsubstituted or substituted by one or more residues from the group consisting of halogen, alkyl with 1 to 4 carbon atoms and an oxo group;
R 7 independently of other residues R 7 means halogen, nitro, cyano, thiocyanato or a residue of the formula -X 2 A 2 , where X 2 means a direct bond or divalently group of the formula -O-, -S (O) q -O-, - O-S (O) q -, -CO-, -O-CO-, -CO-O-, -NR "-, -O-NR" -, -NR "-O-, -NR" -CO- or -CO-NR "-, and in the formulas, q means 0, 1 or 2, R" is hydrogen, alkyl with 1-6 carbon atoms, phenyl, cycloalkyl with 3-6 carbon atoms, and
A 1 is hydrogen or a hydrocarbon residue or a heterocyclic residue, each of the last two residues is unsubstituted or substituted, or two adjacent radicals R 7 together denote a fused ring with 4-6 ring atoms that is carbocyclic or contains heteroatoms from the group including oxygen, sulfur and nitrogen, and which is unsubstituted or substituted by one or more residues from the group including halogen, alkyl with 1-4 carbon atoms and oxygen,
X means a group of the formula -O-, S (O) r -, -NR * - or -N (O) -, moreover, r means 0, 1 or 2, R * is hydrogen or alkyl with 1 to 4 carbon atoms, and
n is 0, 1, 2, 3, 4 or 5,
with the exception of compounds of formula (I) and their salts,
a) where R 1 is 1-haloethyl, 1-halogen-1-methyl-ethyl or 1-halogen-1-methyl-propyl, R 2 , R 3 , R 4 , R 6 are each hydrogen, R 5 is methyl, R 7 is alkyl with 1-4 carbon atoms, OCH 3 or fluorine, and if n equals 2, both R 7 radicals have the same value, n is the number 0, 1 or 2, X is an oxygen atom, and
b) where R 1 is alkyl with 1 to 10 carbon atoms, unsubstituted or substituted with 1 to 4 substituents from the group consisting of alkoxy with 1 to 4 carbon atoms and hydroxyl, R 2 , R 3 , R 4 , R 6 means each hydrogen, R 5 is methyl, R 7 is independent of other radicals R 7 means alkyl with 1-4 carbon atoms, OCH 3 or halogen, n is the number 0, 1, 2, 3 or 4, and X is an oxygen atom.
при этом гетероциклил в остатках содержит 3 - 9 кольцевых атомов, предпочтительно 3 - 6 кольцевых атомов, в частности 5 или 6 кольцевых атомов, и 1 - 3 гетероатома из группы азота, кислорода и серы.2. The compounds of formula (I) and their salts according to claim 1, characterized in that R 1 is alkyl with 1-4 carbon atoms, which is unsubstituted or substituted by one or more residues from the group comprising halogen, hydroxyl, alkoxy with 1 - 4 carbon atoms, alkylthio with 1-4 carbon atoms, alkylsulfonyl with 4-4 carbon atoms and phenyl, or phenyl, which is unsubstituted or substituted, R 2 and R 3 independently of one another denote hydrogen, amino or alkylamino group with 1 to 4 atoms carbon, dialkylamino with 1 to 4 carbon atoms in the alkyl part, a hydrocarbon residue or a xyrocarbon residue, each with 1-6 carbon atoms, or a heterocyclic residue, an oxyheterocyclic residue or an amino heterocyclic residue, each of the last five residues is unsubstituted or substituted by one or more residues from the group comprising halogen, alkoxyl with 1-4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms, alkylthio group with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkenyloxy with 2 to 4 carbon atoms, alkynyloxyl with 2 to 4 carbon atoms, hydroxyl, ami foot group, acylamino group, mono- and dialkylamino group with 1-4 carbon atoms in the alkyl part, nitro group, carboxyl, cyano group, azido group, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, formyl, carbamoyl, mono- and dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, alkylsulfinyl with 1-4 carbon atoms, haloalkylsulfinyl with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, haloalkylsulfonyl with 1-4 carbon atoms and case of cyclical stop tkov and alkyl having 1 - 4 carbon atoms and haloalkyl with 1 - 4 carbon atoms, or acyl radical, or R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 is 3 - 6 membered heterocyclic radical with 1 - 2 heteroatoms, in addition to the nitrogen atom, if necessary, a further heteroatom is selected from the group of nitrogen, oxygen and sulfur, and the residue is unsubstituted or substituted by one or more residues from the group consisting of halogen, alkyl with 1 to 4 carbon atoms and an oxo group, R 4 is hydrogen, amino group, mono- or dialkylamino group with 1-6 carbon atoms in alkyl In part, a hydrocarbon residue or an oxygen-containing hydrocarbon residue, each with 1-6 carbon atoms, or a heterocyclic residue, an oxygen-containing heterocyclic residue or an amino-containing heterocyclic residue, each of the last five residues is unsubstituted or substituted by one or more residues from the group comprising halogen, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms, alkylthio group with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alke niloxyl with 2 to 4 carbon atoms, alkynyloxy with 2 to 4 carbon atoms, hydroxyl, amino group, acylamino group, mono- and dialkylamino group with 1 to 4 carbon atoms in the alkyl part, nitro group, carboxyl, cyano group, azido group, alkoxycarbonyl with 1 to 4 atoms carbon in the alkoxy part, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, formyl, carbamoyl, mono- and dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, alkylsulfinyl with 1-4 carbon atoms, haloalkylsulfinyl with 1-4 carbon atoms, alkylsulfonyl with 1 to 4 atoms and carbon, haloalkylsulfonyl with 1-4 carbon atoms, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxyl and, in the case of cyclic residues, and alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, or acyl residue R 5 and R 6 independently of one another means halogen, nitro, cyano, thiocyanato or a residue of the formula —X 1 -A 1 , where X 1 means a direct bond or divalently groups of the formula —O—, —S—, —CO—, —O — CO -, -CO-O-, -NR'-, -NR'-CO- or -CO-NR'-, and in the formulas R 'is hydrogen or alkyl with 1-6 carbon atoms, and where A 1 is hydrogen or acyclic cue hydrocarbon residue with 1 to 6 carbon atoms, cyclic hydrocarbon residue with 3 to 6 carbon atoms or a heterocyclic residue with 3 to 6 ring atoms and 1 to 3 heteroatoms from the group including nitrogen, oxygen and sulfur, each of the last three residues is unsubstituted or substituted by one or more residues from the group comprising halogen, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio group with 1-4 carbon atoms, alkenyl with 2-4 carbon atoms, alkynyl with 2-4 atoms carbon, alkenyloxy with 2 - 4 carbon atoms, alkynyloxy with 2-4 carbon atoms, hydroxyl, amino group, acylamino group, mono- and dialkylamino group with 1-4 carbon atoms in the alkyl part, cycloalkylamino group with 3-6 carbon atoms, nitro group, carboxyl, cyano group, azido group, unsubstituted or substituted heterocyclyl, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, formyl, carbamoyl, mono- and dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, unsubstituted or substituted phenylcarbonyl alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, haloalkylsulfonyl with 1 to 4 carbon atoms and, in the case of cyclic residues, and alkyl with 1 to 4 carbon atoms and haloalkyl with 1 to 4 carbon atoms, or R 5 and R 6 together mean an alkylene chain with 2 to 4 carbon atoms, unsubstituted or substituted by one or more residues from the group comprising halogen, alkyl with 1 to 4 atoms carbon and oxog Upp, (R 7 ) n n means residues R 7 that, if n = 2, 3, 4 or 5, are the same or different, and R 7 means halogen, nitro, cyano, thiocyanato or a residue of the formula -X 2 A 2 , where X 2 means a direct bond or divalent group of the formula -O-, -S (O) q -, -S (O) q -O-, -OS (O) q -, -CO-, -O-CO-, -CO-O-, -NR "-, -O-NR" -, -NR "-O-, -NR" -CO- or -CO-NR "-, moreover, in the formulas q - 0, 1, 2, and R "is hydrogen, alkyl with 1-6 carbon atoms, phenyl or cycloalkyl with 3-6 carbon atoms, and where A 2 is hydrogen or alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, alkynyl with 2 - 6 carbon atoms, cycloalkyl with 3 - 6 carbon atoms, cyclo 3-6 carbon atoms, phenyl or heteroaryl, each of the last seven residues is unsubstituted or substituted by one or more residues from the group comprising halogen, hydroxyl, nitro, cyano, amino, acylamino, aminocarbonyl, mono- and dialkylamino with 1 to 4 carbon atoms in the alkyl part, mono- and dialkylamino-carbonyl with 1 to 4 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, cycloalkoxy with 3 to 6 carbon atoms, alkoxyl with 1 to 6 carbon atoms, alkylthio group with 1 to 6 carbon atoms, 1-6 carbon atoms, alkylcarbonyl 1-6 carbon atoms, alkoxycarbonyl 1-6 carbon atoms, alkylcarbonyloxy 1-6 carbon atoms, cycloalkylcarbonyl 3-6 carbon atoms, phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyl, phenylcarbonyl, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyl, phenylcarbonyl, phenoxycarbonyl heterocyclylalkyl with 1 to 6 carbon atoms in the alkyl part, and, in the case of cyclic residues, and alkyl with 1 to 6 carbon atoms, each of the last 20 residues unsubstituted or substituted by one or more residues from the group consisting of halogen, hydroxyl, amino, di alkylamino with 1-4 carbon atoms in the alkyl part, nitro, cyano, alkoxy with 1-4 carbon atoms, alkylthio group with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms and, in the case of cyclic residues, and alkyl with 1 to 4 carbon atoms and haloalkyl with 1-4 carbon atoms, or two adjacent residues R 7 together mean a fused ring with 4 to 6 ring atoms, which is carbocyclic or contains 1 to 3 heteroatoms from the group including oxygen, sulfur and nitrogen and which unsubstituted or substituted by one or several residues from the group including halogen, alkyl with 1-4 carbon atoms and an oxo group, X is a group of the formula -O-, -S (O) r - or -NR * -, where r is 0, 1 or 2, and R * is hydrogen or alkyl with 1 to 4 carbon atoms, and n is 0, 1, 2, 3, 4, or 5,
while the heterocyclyl in the residues contains 3 to 9 ring atoms, preferably 3 to 6 ring atoms, in particular 5 or 6 ring atoms, and 1 to 3 heteroatoms from the nitrogen, oxygen and sulfur groups.
при этом гетероциклил в остатках содержит 3 - 9 кольцевых атомов и 1 - 3 гетероатома из группы азота, кислорода и серы.3. The compounds of formula (I) and their salts according to claim 1 or 2, characterized in that R 1 - alkyl with 1 to 4 carbon atoms, which is unsubstituted or substituted by one or more residues from the group including halogen, hydroxyl, alkoxyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms and phenyl, or phenyl, which is unsubstituted or substituted by one or more residues from the group including halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms, alkylthio group with 1 to 4 carbon atoms Erode, nitro, cyano, alkylcarbonyl with 1 - 2 carbon atoms in the alkyl moiety, formyl, carbamoyl, mono- and dialkylaminocarbonyl with 1 - 2 carbon atoms in the alkyl part and alkylsulfonyl with 1 - 4 carbon atoms, R 2 and R 3 independently from each other means hydrogen, amino group, formyl, aminocarbonyl, alkyl with 1-4 carbon atoms, cyanoalkyl with 1-4 carbon atoms, alkylamino group with 1-4 carbon atoms, dialkylamino group with 1-4 carbon atoms in the alkyl part, haloalkyl with 1 - 4 carbon atoms, hydroxyalkyl with 1 to 4 carbon atoms, alko xyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, haloalkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2-6 carbon atoms, haloalkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, haloalkynyl with 2 to 6 carbon atoms, alkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, cycloalkylaminoalkyl with 3 - 6 carbon atoms in the cycloalkyl part and 1 to 4 atom amides of carbon in the alkyl part, cycloalkyl with 3-6 carbon atoms, heterocyclylalkyl with 3-6 carbon atoms in the heterocyclic part and 1-4 carbon atoms in the alkyl part, with the cyclic groups in the last three residues unsubstituted or substituted by one or several residues from the group containing alkyl with 1-4 carbon atoms, halogen and cyano group, or alkanolamine group with 1-6 carbon atoms, N-alkanoyl-N-alkylamino group with 1-6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, alkanoyl amino alkyl from 1 - 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, N-alkanoyl-N-alkylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in each alkyl part, phenyl, phenoxy, phenylcarbonyl, phenyl hydroxycarbonyl, phenylcarbonylalkyl with 1-4 carbon atoms, alkoxycarbonylalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, alkylaminocarbonylalkyl with 1-4 carbon atoms in each alkyl part, alkylcarbonyl with 1-4 carbon atoms in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, phenoxyalkyl with 1-4 carbon atoms, phenylalkyl with 1-4 carbon atoms, heterocyclyl, a heterocyclylamino group, a heterocyclyloxy group, a heterocyclyl thio group, or one of the 21 last residues that is substituted in the acyclic part or cyclic part by one or more residues from the group consisting of halogen, nitro, cyano, alkoxy of 1-4 carbon atoms, alkyl thio group with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, alkylcarbonyl with 1-4 carbon atoms and, in the case of cyclic residues, and alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, or R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 means a 3-6-membered heterocyclic residue with 1 to 2 heteroatoms, and besides the nitrogen atom, a further heteroatom, if necessary, is selected from the group of nitrogen, oxygen and sulfur, and the residue is unsubstituted or substituted by one or more residues from the group comprising halogen, alk sludge with 1-4 carbon atoms and oxo group, R 4 - hydrogen, amino group, formyl, aminocarbonyl, alkyl with 1-4 carbon atoms, cyanoalkyl with 1-4 carbon atoms, alkylamino group with 1-4 carbon atoms, dialkylamino group with 1-4 carbon atoms in the alkyl part, haloalkyl with 1 to 4 carbon atoms, hydroxyalkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, haloalkoxyalkyl with 1 to 4 carbon atoms in alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2 to 6 atom amides of carbon, haloalkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, haloalkynyl with 2-6 carbon atoms, alkylaminoalkyl with 1-4 carbon atoms in each alkyl part, dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part , cycloalkylaminoalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, heterocyclylalkyl with 3 to 6 carbon atoms in the heterocyclyl part and 1 to 4 carbon atoms in the alkyl part, and cyclic groups in the last three x residues are unsubstituted or substituted by one or more residues from the group comprising alkyl with 1-4 carbon atoms, halogen and cyano group, or alkanolamine group with 1-6 carbon atoms, N-alkanoyl-N-alkylamino group with 1-6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, alkanoylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, N-alkanoyl-N-alkylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in each alkyl part, phenyl, phenoxy, enylcarbonyl, phenoxycarbonyl, phenylcarbonylalkyl with 1-4 carbon atoms, alkoxycarbonylalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, alkylaminocarbonylalkyl with 1-4 carbon atoms in each alkyl part, alkylcarbonyl with 1-4 carbon atoms carbon in the alkyl part, alkoxycarbonyl with 1-4 carbon atoms in the alkoxy part, alkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, phenoxy alkyl with 1-4 carbon atoms, phenylalkyl 1 to 4 carbon atoms, heterocyclyl, heterocyclylamino group, heterocyclyloxy, heterocyclylthio group, or one of the 21 last residues that is substituted in the acyclic part or, preferably, in the cyclic part, by one or more residues from the group consisting of halogen, nitro, cyano, alkyl, alkyl, alkyl. 4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio group with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, alkylcarbonyl with 1-4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms and, in the case of cyclic residues, and alkyl with 1 to 4 carbon atoms and haloalkyl with 1 to 4 carbon atoms, R 5 and R 6 independently of one another denote hydrogen, halogen, hydroxyl, amino, nitro, formyl , aminocarbonyl, carboxyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, cyanoalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylamino group with 1-4 carbon atoms, dialkylamino group with 1-4 carbon atoms in alkyl parts, haloalkyl with 1-4 carbon atoms, hydroxyalkyl with 1-4 carbon atoms Ordine, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, haloalkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, an alkylthio group with 1 to 4 carbon atoms, halo alkylthio group with 1-4 carbon atoms, alkenyl with 2-6 carbon atoms, haloalkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, haloalkynyl with 2-6 carbon atoms, alkylaminoalkyl with 1-4 carbon atoms in each alkyl part, dialkylaminoalkyl with 1 to 4 carbon atoms in each th alkyl part, cycloalkylaminoalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, heterocyclylalkyl with 1 to 4 carbon atoms in the alkyl part and 3 to 6 ring members, and cyclic groups in the last three residues are unsubstituted or substituted by one or more residues from the group comprising alkyl with 1-4 carbon atoms, halogen and cyano group, or alkanoylamino group with 1-6 carbon atoms, N-alkanoyl-N-alkylamino group with 1-6 atoms carbon in alkanoyl parts and 1 to 4 carbon atoms in the alkyl part, alkanoylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, N-alkanoyl-N-alkylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 - 4 carbon atoms in each alkyl part, phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonylalkyl with 1-4 carbon atoms, alkoxycarbonylalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, alkylaminocarbonylalkyl with 1-4 atoms carbon in each alkyl part, and lkylcarbonyl with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms, alkylaminocarbonyl with 1-4 carbon atoms, dialkylaminocarbonyl with 1-4 carbon atoms in the alkyl part, phenoxy alkyl with 1-4 carbon atoms, phenylalkyl with 1-4 carbon atoms , heterocyclyl, heterocyclylamino group, heterocyclyloxy, heterocyclylthio group or one of the 21 last residues that is substituted in the acyclic or cyclic part by one or more residues from the group consisting of halogen, nitro, cyano, alkoxy with 1 to 4 atoms carbonate, alkylthio group with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, alkylcarbonyl with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms and, in the case of cyclic residues, and alkyl with 1-4 carbon atoms and haloalkyl with 1 to 4 carbon atoms, or R 5 and R 6 together mean an alkylene chain with 2 to 4 carbon atoms, which is unsubstituted or substituted by one or more residues from the group containing halogen, alkyl with 1 to 4 carbon atoms and an oxo group, (R 7) n n means the residues R 7 which, if n = 2, 3, 4 or 5 identical or once ichny, and R 7 is halogen, hydroxyl, amino, nitro, formyl, aminocarbonylalkyl with 1 - 4 carbon atoms, carboxyl, cyano, thiocyanato group or an alkyl group having 1 - 6 carbon atoms, alkoxy having 1 - 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, cycloalkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 - 4 carbon atoms in the alkyl part, cycloalkylalkenyl with 3 to 6 carbon atoms in c the clooyl part and 1 to 4 carbon atoms in the alkenyl part, cycloalkylalkynyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkynyl part, alkylcarbonyl with 1 to 6 carbon atoms, cycloalkoxyl with 3 to 6 carbon atoms, cycloalkylcarbonyl with 3 to 6 carbon atoms, alkoxycarbonyl with 1 to 6 carbon atoms, alkylcarbonyloxy with 1 to 6 carbon atoms, alkylcarbonylalkyl with 1 to 6 carbon atoms in each alkyl part, alkoxycarbonylalkyl with 1 to 6 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part and alkylcarbonyloxyalkyl with 1 to 6 carbon atoms in each alkyl part, cycloalkoxyalkyl with 1 to 6 carbon atoms in the cycloalkoxy part and 1 to 4 carbon atoms in the alkyl part, cycloalkylcarbonylalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part, monoalkylamino group with 1-6 carbon atoms, dialkylamino group with 1-4 carbon atoms in the alkyl part, alkanoylamino group with 1-6 carbon atoms, N-alkanoyl-N-alkylamino group with 1-6 carbon atoms in the alkanoyl part and 1 - 4 carbon atoms in a the acid part, alkanolamine alkyl with 1-6 carbon atoms in the alkanoyl part and 1-4 carbon atoms in the alkyl part or N-alkanoyl-N-alkylaminoalkyl with 1-6 carbon atoms in the alkanoyl part and 1-4 carbon atoms in each alkyl part, each of the last 26 residues in the acyclic part or in the cyclic part is replaced by one or more residues from the group including halogen, nitro, amino, aminoalkyl with 1-4 carbon atoms, mono- and dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part , hydroxyl, qi nogroup, alkoxy with 1-4 carbon atoms, alkylthio group with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylcarbonyl with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms and, in the case of cyclic residues, and alkyl with 1 - 4 carbon atoms and haloalkyl with 1 - 4 carbon atoms, or phenyl, phenoxy, phenylthio, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenylsulfonyl, phenoxyalkyl with 1 - 6 carbon atoms, fenilkarbonilalkil with 1 - 6 carbon atoms, feniloksikarbonilalkil 1 - 6 carbon atoms, phenylcarbonyl textiles with 1-4 carbon atoms, phenylalkyl with 1-6 carbon atoms, phenylalkenyl with 1-6 carbon atoms, phenylalkynyl with 1-6 carbon atoms, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylsulfonyl, cycloalkyls, heterocyclics, heterocyclylthio, heterocyclylsulfonyl, heterocyclics, heterocyclyl, heterocyclyl one of the last 20 residues, which is substituted by one or several residues from the group including halogen, hydroxyl, nitro, cyano, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkylthio group with 1-6 carbon atoms, alkyls lfonil with 1 - 4 carbon atoms, haloalkyl with 1 - 6 carbon atoms and haloalkoxy with 1 - 6 carbon atoms, or two adjacent residues R 7 together represent prikondensirovanny ring having 4 - 6 ring atoms which is carbocyclic or contains 1 - 3 heteroatoms from the group comprising oxygen, sulfur and nitrogen, and which is unsubstituted or substituted by one or more residues from the group including halogen, alkyl with 1-4 carbon atoms and an oxo group, X is a group of the formula -O-, -S- or -NR * -, where R * is hydrogen or alkyl with 1-4 carbon atoms, and n is 0, 1, 2, 3, 4, or 5,
while heterocyclyl in the residues contains 3 to 9 ring atoms and 1 to 3 heteroatoms from the nitrogen, oxygen and sulfur groups.
при этом гетероциклил в остатках содержит 3 - 9 кольцевых атомов и 1 - 3 гетероатома из группы азота, кислорода и серы.4. The compounds of formula (I) and their salts according to one of claims 1 to 3, characterized in that R 1 is alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, hydroxyalkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part or benzyl, R 2 and R 3 independently of each other mean hydrogen, amino group, formyl, alkyl with 1-4 carbon atoms, alkoxyalkyl with 1 - 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms , alkylaminoalkyl with 1-4 carbon atoms in each alkyl part, dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part or phenyl, phenylalkyl with 1-4 carbon atoms or phenoxycarbonyl or one of the last three residues, which in the phenyl part is mono- three times substituted by residues from the group consisting of halogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms and alkoxycarbonyl with 1-4 carbon atoms, or R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 mean 3 - 6-membered heterocyclic residue with 1 to 2 heteroatoms, etc. than the addition to the nitrogen atom is available if necessary a further heteroatom selected from nitrogen and oxygen, and the residue is unsubstituted or substituted by one or more radicals from the group consisting of halogen, alkyl having 1 - 4 carbon atoms and an oxo group, R 4 - hydrogen, amino, formyl, alkyl with 1-4 carbon atoms, dialkylamino group with 1-4 carbon atoms in the alkyl part, alkoxyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, alkenyl with 2-6 carbon atoms, alkynyl with 2 - 6 carbon atoms, dialkylamino kil with 1-4 carbon atoms in each alkyl part, phenyl, phenoxyalkyl with 1-4 carbon atoms, phenylalkyl with 1-4 carbon atoms, phenoxycarbonyl, phenylaminocarbonyl or one of the last five residues, which in the phenyl part is mono-up to three times substituted by residues from the group comprising alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms and alkoxycarbonyl with 1-4 carbon atoms, R 5 and R 6 independently of one another denote hydrogen, alkyl with 1-4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in alk xyl part and 1 to 4 carbon atoms in the alkyl part, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, phenyl, phenoxyalkyl with 1 to 4 carbon atoms, phenylalkyl with 1-4 carbon atoms, phenoxycarbonyl, phenylaminocarbonyl or one of the last three residues, which in the phenyl part is mono-to three-fold substituted by residues from the group including halogen, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms and alkoxycarbonyl with 1 to 4 carbon atoms, or R 5 and R 6 in place means an alkylene chain with 2 to 4 carbon atoms, unsubstituted or substituted by one or more residues from the group consisting of halogen, alkyl with 1 to 4 carbon atoms and an oxo group, (R 7 ) n n means R 7 residues, which, if n = 2, 3, 4 or 5 are the same or different, and R 7 means halogen, hydroxyl, amino group, nitro group, formyl, aminocarbonyl, carboxyl, cyano group, thiocyanato group, alkyl with 1-6 carbon atoms, alkoxyl with 1-4 atoms carbon, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, hydroxyalkyl with 1 - 4 carbon atoms, hydroxyalkoxy with 1-4 carbon atoms, alkoxyalkyl with 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, alkoxyalkoxy with 1-4 carbon atoms in each alkoxy part, 1-4 halogen alkoxyalkyl carbon in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, haloalkoxyalkoxy with 1-4 carbon atoms in each alkoxy part, cycloalkyl with 3-6 carbon atoms, halocycloalkyl with 3-6 carbon atoms, alkenyl with 2-6 carbon atoms, haloalkenyl with 2 to 6 carbon atoms yes, alkynyl with 2-6 carbon atoms, haloalkynyl with 2-6 carbon atoms, alkylcarbonyl with 1-4 carbon atoms, haloalkylcarbonyl with 1-4 carbon atoms, cycloalkyloxy with 3-6 carbon atoms, halo-cycloalkyloxy with 3-6 carbon atoms, cycloalkylcarbonyl with 3-6 carbon atoms, halo-cycloalkylcarbonyl with 3-6 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms, haloalkoxycarbonyl with 1-4 carbon atoms, alkylcarbonyloxyl with 1-4 carbon atoms, haloalkylcarbonyloxyl with 1-4 carbonyl atoms and carbonyl atoms with 1-4 carbon atoms, haloalkylcarbonyloxycarbonyl with 1-4 carbon atoms with 1-4 carbon atoms, haloalkylcarbonyloxycarbonyl with 1-4 carbon atoms with 1-4 carbon atoms, haloalkylcarbonyloxycarbonyl with 1-4 carbon atoms with 1-4 carbon atoms, haloalkylcarbonyloxycarbonyl with 1-4 carbon atoms and carbon atoms of 1-4 carbon atoms, haloalkylcarbonylcarboxylic carbonyl with 1-4 carbon atoms with 1-4 carbon atoms 1 to 4 atoms carbon in each alkyl part, alkoxycarbonylalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkylcarbonyloxyalkyl with 1 to 4 carbon atoms in each alkyl part, alkylthio group with 1 to 4 carbon atoms, alkyl alkyl group with 1 - 4 carbon atoms, alkylamino group with 1-4 carbon atoms, dialkylamino group with 1-4 carbon atoms in the alkyl part, alkanolamine group with 1-6 carbon atoms, N-alkanoyl-N-alkylamino group with 1-6 carbon atoms in the alkanoyl part and 1 - 4 carbon atoms in alk the flax part, alkanoyl amino alkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in the alkyl part, N-alkanoyl-N-alkylaminoalkyl with 1 to 6 carbon atoms in the alkanoyl part and 1 to 4 carbon atoms in each alkyl part, or phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy alkyl with 1-4 carbon atoms, phenylcarbonylalkyl with 1-4 carbon atoms, phenylalkyl with 1-4 carbon atoms, phenylalkenyl with 2-6 carbon atoms, phenylalkynyl with 2-6 atom, carbon, heterocyclyl, heterocyclyloxy, heterocycly thio group, heterocyclylamino group, heterocyclylalkyl with 1-6 carbon atoms, or one of the last 15 residues, which is substituted in the cyclic part by one or more residues from the group including halogen, hydroxyl, nitro, alkyl with 1-4 carbon atoms, alkoxy with 1 - 4 carbon atoms, alkylthio group with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms and haloalkoxy with 1-4 carbon atoms, or two adjacent R 7 together denote a fused ring with 4-6 ring atoms, which is carbocyclic or contains heteroatoms from the group comprising oxygen, sulfur and nitrogen, and which is unsubstituted or substituted by one or more residues from the group including halogen, alkyl with 1 to 4 carbon atoms and an oxo group, X is a group of the formula -O- or -NR * -, where R * is hydrogen or methyl, and n is 0, 1, 2, 3, 4, or 5,
while heterocyclyl in the residues contains 3 to 9 ring atoms and 1 to 3 heteroatoms from the nitrogen, oxygen and sulfur groups.
R1-Fu
где Fu означает функциональную группу, имеющуюся у остатков, таких, как сложный эфир карбоновой кислоты, ортоэфир карбоновой кислоты, хлорид карбоновой кислоты, амид карбоновой кислоты, ангидрид карбоновой кислоты и трифторметил,
подвергают взаимодействию с бигуанидином формулы (III) или его кислотно-аддитивной солью
или б) соединение формулы (IV)
где Z1 представляет собой заменяемый остаток или удаляемую группу, подвергают взаимодействию с пригодным амином формулы (V) или его кислотно-аддитивной солью
причем указанные в формулах (II), (III), (IV) и (V) остатки R1 до R7 и X, а также n имеют указанное в формуле (I) значение.7. The method of obtaining compounds of General formula (I) and their salts according to one of paragraphs.1 to 6, characterized in that a) a compound of formula (II)
R 1 -Fu
where Fu means a functional group present in residues such as carboxylic ester, ortho ester of carboxylic acid, carboxylic acid chloride, carboxylic acid amide, carboxylic anhydride, and trifluoromethyl,
subjected to interaction with biguanidine formula (III) or its acid additive salt
or b) the compound of formula (IV)
where Z 1 is a replaceable residue or a removable group, is subjected to interaction with a suitable amine of the formula (V) or its acid additive salt
moreover, residues R 1 to R 7 and X, as well as n, indicated in formulas (II), (III), (IV) and (V), as well as n, have the meaning indicated in formula (I)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19704922.2 | 1997-02-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
RU99119226A true RU99119226A (en) | 2001-07-27 |
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