3-amino-9h-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamid showing astragulus and anti-stress activity
The invention relates to organic chemistry and agriculture. Describes 3-Amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamid,
showing astragulus and anti-stress activity. The technical result is obtained a new connection, promising chemistry of biologically active substances obtained synthetically, for use in agriculture as growth regulators and anti-stress drugs. table 2.
The invention relates to the field of agriculture and chemistry of biologically active substances, to a new biologically active compound from a number of condensed heterocyclic compounds of the formula I
exhibiting the properties of activator germination of winter wheat varieties Polovinka.
The specified connection is representative of a new heterocyclic system and its chemical and biological properties in the literature is unknown.
To the closest analogs in the structure of the claimed compounds can be attributed Dibazol - (2-benzyl-benzimidazole) - medical drug with vasodilating, spasmolin the Chemistry of heterocyclic compounds. - M.: Higher school, 1978.-559 S.; Mashkovsky M. D. Medicines. - M.: Medicine. -1987.-576 C.].
As similar properties known gibberellins, are widely used to activate germination. However, gibberellins costly products of microbiological synthesis and inaccessible. Its use causes irrational waste of plastic substances [Muromtsev, S. and other foundations of chemical regulation of growth and productivity of plants. - M.: Agropromizdat.-1987.-S. 33-80].
The present invention is to obtain a new connection, promising chemistry of biologically active substances and expand the Arsenal of biologically active substances obtained synthetically, for use in agriculture as growth regulators and anti-stress drugs.
This is achieved by the synthesis of 3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamide, a new previously undescribed compounds exhibiting the properties of activator germination of winter wheat varieties Polovinka.
Compound I was obtained by reaction of alkylation of amide nitrile malonic acid chloromethylthiazole in the presence of potassium carbonate in DMSO.
The original prophetic is by the following examples.
Obtaining the synthesis of 3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamide
In a flat-bottomed flask was placed 13.8 g (0.1 mol) K2CO3150 ml of dimethyl sulfoxide (DMSO) and heated to 40-50°C was added to 4.2 g (0.05 mol) of the amide of malonic acid nitrile. After 10 minutes from a dropping funnel was bury solution 8,32 g (0.05 mol) of chloromethylthiazole in 20 ml of DMSO within half an hour. The reaction was conducted for 5 hours (TLC control). Then the reaction mixture was poured into cold water, acidified with a solution of 10% hydrochloric acid to pH=6, was filtered light yellow crystals. The yield of compound I was 8.0 g(75%). TPL=165-167°C.
Elemental analysis for C11H10N4(214):
Calculated (%): 61,68, N 4,67, N 26,18, 7,47. Found (%): 61,65, N 4,69, N 26,20, O 7,46.
An NMR spectrum1H (DMSO-d6), (, m D.): the 5.45 (s, 1H, NH); 6,23 (s, 1H, CH); 6,9...to 7.18 (m, 4H, HPh); 7,28 (c,4H, 2NH2).
X , cm-1: 3250, 3500(NH2), 1700 (C=O), 1620, 1600 (C=C).
The study astragalina and anti-stress activity of 3-amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamide
Astragulus and anti-stress activity of the claimed compounds of formula is ormula I and similar in structure Dibazol used in an aqueous solution with a mass fraction of 0.01%, of 0.005%, about 0.001%, of 0.0005% and 0.0001%, similar to properties of gibberellin in the form of an aqueous solution with a mass fraction of 0.001% by pre-sowing seed soaking for 18 hours At quality control taken seeds treated with water. Each sample used for 50 PCs of seeds. Experiment was repeated three times.
Seeds were germinated for 7 days in rolls of filter paper. About activity of the compounds was judged by their effect on seed germination, height of sprouts, length of roots, and their mass and potential productivity. The research results are summarized in tables 1 and 2.
Tests conducted on seeds of winter wheat varieties Polovinka, revealed that all the tested compounds in the concentration range of 0.01 and 0.0001 wt.% exhibit the properties of growth stimulants.
Dibazol in optimal growth stimulating dose of 0.0001 wt.% increases the germination energy by 6%, the length of the cane system 7-days-old seedlings - by 16.3%, the length of roots seedling - 23.2% and their weight - 17.5 and 18.8% respectively in comparison with control (0.1 wt.% an aqueous solution of DMSO).
The claimed connection in optimal growth stimulating concentration of 0.0005 wt.% increases vigor by 6%, the length of Pobierowo the efficiency - 7.8%, compared to control.
In conditions of water stress tested compounds remain active growth and synthetic processes, activating the growth of cane system of seedlings and contributing to the regeneration of roots.
Dibazol in optimal postactivity concentration of 0.0005 wt.% increases the height of the seedlings 32.2%, length of roots - 20.8% and the weight by 35.3 and 21.4% respectively in comparison with control (0.1 wt.% an aqueous solution of DMSO).
The claimed connection in optimal postactivity concentration of 0.0005 wt.% increases the length of the cane system by 47.5%, length of roots - 41.5% and their mass - 64.7% and 25.0%, respectively, compared to control.
Thus, the claimed connection to its effectiveness is not inferior to similar in structure and properties shows the properties of highly effective stimulator of growth and increases the resistance of seedlings of winter wheat varieties Polovinka to water stress, and therefore, can be used in arid areas to improve seed winter wheat.
3-Amino-N-benzo[d]-pyrrolo-[1,2 a]imidazol-2-carboxamid formula
showing astragulus and anti-stress
using the diamine of General formula
R=2-furyl, 2-thienyl, 2-(1-methyl)pyrrolyl, 3-(1-methyl)indolyl, and aldehydes in the presence of acetate or copper sulfate, characterized in that the interaction takes place by boiling in 50% acetic acid, followed by decomposition of the copper salt, the effect on its suspension in 50% acetic acid sodium thiosulfate in 100With
< / BR>or their pharmaceutically acceptable salts, in which the dotted lines indicate optional double bonds; A is-CR7or N; - - NR1R2, -CR1R2R11, -C(= CR2R12R1, -NHCHR1R2, -ОСHR1R2, -SCHR1R2, -CHR2OR12,
-CHR2SR12, -C(S)R2or-C(O)R2N-ethyl-2,2,2-triptorelin; G is oxygen, sulfur, NH, NH3hydrogen, methoxy, ethoxy, triptoreline, methyl, ethyl, dimethoxy, NH2, NHCH3N(CH3)2or trifluoromethyl; Y Is N; Z is NH, O, S, -N(C1-C2alkyl) or-C(R13R14), where R13and R14independently of one another represent hydrogen, trifluoromethyl or methyl, or one of the elements of R13and R14is cyano and the other is hydrogen or stands; R1- C1-C6alkyl which may be optionally substituted by one or two substituents R8independently from each other selected from the group comprising hydroxy, fluorine, chlorine, bromine, iodine, CF3C1-C4alkoxy, -O-CO-(C1-C4alkyl), where (C1-C2- C1-C12alkyl, aryl or -(C1-C4alkylene)aryl, where aryl is phenyl, naphthyl; R3is methyl, ethyl, fluorine, chlorine, bromine, iodine, cyano, methoxy, OCF3, methylthio, methylsulphonyl, CH2HE or CH2OCH3; R4is hydrogen, C1-C4alkyl, fluorine, chlorine, bromine, iodine, C1-C4alkoxy, triptoreline, -CH2OCH3, -CH2OCH2CH3, -CH2CH2OCH3, -CF3, amino, nitro, -NH(C1-C4alkyl), -N(CH3)2, -NHCOCH3, -NHCONHCH3, hydroxy, -CO(C1-C4alkyl), -Cho, COOH, cyano, or-COO(C1-C4alkyl), where C1-C4the alkyl may be substituted by one Deputy chosen from the group comprising hydroxy, amino, -NHCOCH3, -NH(C1-C2alkyl), -N(C1-C2alkyl)2, fluorine, chlorine, cyano, nitro; R5is phenyl, naphthyl, pyridyl, pyrimidyl, where each of the above groups R5substituted with one to three substituents that are independently from each other selected from fluorine, chlorine, C1-C6the alkyl or C1-C6alkoxyl, or one Deputy chosen from the group comprising hydroxy, iodine, bromine, formyl, cyano, nitro, trifluoromethyl, amino, -(C1-C6these groups of R5may be optionally substituted with one hydroxy-group; R6is hydrogen or C1-C6alkyl; R7is hydrogen, methyl; R11is hydrogen, hydroxy, fluorine or methoxy; R12is hydrogen or C1-C4alkyl, and R16and R17independently of one another represent hydrogen, hydroxy, methyl, ethyl, methoxy or ethoxy, except that both R16and R17cannot both be methoxy or ethoxy; or R16and R17together form oxo (=O) group; provided that if G is an atom of oxygen, sulfur, NH or NCH3he is joined by a double bond to a five-membered ring of the formula III, and further provided that R6is absent when the nitrogen atom to which it is linked, is attached by a double bond to an adjacent carbon atom in the ring
SUBSTANCE: invention describes a method for feeding potato and tomato with 6-benzylaminopurine an aqueous solution taken in the concentration 10-4 M and growing pants up to preparing harvest according to technology accepted for the culture crop. Invention proposes 3-fold treatment of plants for vegetation: at the lateral branching phase, at onset of forming economically value organs and immediately after the growth termination. Method provides the effective enhancing the productivity of the most important vegetable crops - tomato and potato.
EFFECT: improved enhancing method.
6 tbl, 4 ex