SU1098934A1 - 4-aminomethyl derivatives of 2-methyl-5-hydroxybenzimidazole having growth stimulating effect - Google Patents

Abstract

.4-aminomethyl derivatives of 2-methyl-5-hydroxybenzimidazole of the general formula CHgB. but. J. If VCH, -N HCl H where A (CH3) 2 —O-O has a growth promoting activity.

Description

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The invention relates to new derivatives of hydroxybenzimidazole, namely, to 4-aminomethyl derivatives of 2-methyl-5-hydroxybenzimidazole of the general formula CHglt N -.snz in HC1, where; (CH3) 2 -O with a growth-promoting activity. 5-Chlorobenzimidazole is known, which has a growth-promoting effect. See on cotton. However, the activity of this compound in relation to the stimulation of the growth of roots and seedlings is small. The purpose of the invention is to search for new compounds in the range of hydroxybenzimidazoles with higher growth-promoting activity. This goal is achieved by the proposed compounds of the general formula I, which have a growth-stimulating effect, which is obtained by the interaction of equivalent amounts of 2-methyl-5-hydroxybenzimidazole and N-alkoxymethyleneamine or N, N-methylenebeneamine upon heating. The compounds of general formula I are a white crystalline substance with a mp. above 200 C, soluble in water and alcohol. Example 1. 2-Metsh1-4-piperidinomethyl-5-hydroxybenzimidazole hydrochloride (BIO-20). To a solution of 0.5 g (0.0038 M) of 2-methcp-5-hydroxybenzimidazole in 3 ml of alcohol is added dropwise 0.49 ml (0.0038 M) of N-methoxymethylpiperidine. The reaction mixture is boiled for 1 , 5 hours, about, they coax and hold for 30 minutes at 0. The crystals entered are separated, washed with ether, and 2-methyl-4-piperidinomethyl-5-hydroxybenzimidazole is obtained. The output of 0.66 g (93%), so g. 217-Z18 with. Found:% C 68.24; 68.12; .-H 7.68; 7.65. Calculated,%: C 68.53; H 7.82. 10 0.5 g of 2-methyl-4-piperidinometh-5-hydroxybenzimidazole is dissolved at boiling in 5 ml of 20% HCl alcohol solution, the solution is cooled, and the precipitated crystals are separated. 2-methyl-4-piperidinomethyl-5-hydroxybenzimidazole hydrochloride is obtained. Yield 0.55 g (96%), so pl. 246-247 C. Found,%: C 50.17; H 6.97. -ngsn about Calculated,%: C 50.00; H 6.91. PMR spectrum: 7.70; 7.61 (d, 1n, 7n), 7, 20; 7.11 (d, 1H, 6H); 4.52 (C, 2H, CH); 3.56 (m); 3.17 (m); 1.91 (m); YUN, 2.92 ppm (C, ZN, CH). Example 2 2-metsh1-4-morpholinomethyl-5-hydroxybenzimidazole hydrochloride (BIO-30). 2-Methyl-4-morpholinomethyl-5-hydroxy; benzimidazole is prepared analogously to example 1 from 0.5 g (0.0038 M) of 2-methyl-5-hydroxybenzimidazole and 0.46 ml (0.0038 M) of N-methoxymethylmorpholine in 3 ml of alcohol. The output of 0.63 g (89%). M.p. 216 217 ° C. . Found,%: C 61731-, 61.29; H 6.90 i 6.88. Calculated,%: C, 61.29; H, 6.70. According to Example 1, 2-methyl-4-morpholinomethyl-5-hydroxybenzimidazole hydrochloride is obtained. M.p. 252-233 Found: C 48.97; H 5.96. C :, 2HS1 1 / 2H, 0. C Vyisleno,%: C 48.75; H 5.98. PMR spectrum: 7.71; 7.62 (d, 1H, 7-H); 7.20-, 7.1.1 (d, 1H, 6-H); 4.62 (C, 2H, CH), 4.09 (m); 3.56 (m, 8H, -N V); 2.87 ppm (С, ЗН, СНз). Example 3. 2-Methyl-4-dimethylaminomethyl-5-hydroxybenzimidazolchlorogirrat (BIO-40). To a solution of 0.74 g (0.005 M) of 2-methyl-5-hydroxybenzimidazole in 5 ml of alcohol, 0.68 ml (0.0005 M) of N, N, N, N-tetramethyndiamine is added dropwise. The mixture is boiled for 45 minutes, the excess solvent is partially distilled. When cooled down sediment. Crystallization from alcohol gives 2-methyl-4-dimethyl-5-hydroxybenzimidazole. The output of 0.67 g (65.4%) of a white crystalline substance. M.p. 210 C. Found,%: C 63.87 63.92; H 7.45} 7.42. C ,, H jON,. Calculated,%: C 64.35; H 7.38. 31 According to Example 1, 2-methyl-A-dimethyl-5-hydroxybenzimidazole hydrochloride is obtained. M.p. 201 s. Found,%: C 48.92, 49.06; H 5.66i 5.62. .2HC1.1 / 2HjO, Calculated,%: C 48.75t H 5.98.

PMR spectrum: 7.70; 7.61i (d, 1H,

7-H); 7.20} 7.11 (d, 1H, 6-H), 4.62 Table. 1 presents the data of the CU (C, 2H, CHj); 2.98 (С 6К, 4-Н (СНз) 2), Yurennye of 4 replications of experience.

2,88 м.Д. (C, ZN, CHj). Results indicate that.

The synthesized compounds have tested that the 5-hydroxybenzimidazole derivatives under laboratory conditions have a pronounced stimulatory effect of plant growth stimulators. Their effect on root growth (the length of which by control in experiments is 136% of the feed grain length, grown control plants) and hypocotina water. maize seedlings of maize (up to 139%),

Example 4. Corn seeds also to increase their phytomass

Sterling varieties pickle 0.01% 7do 223%). Activity stimulus data

formalin solution for 10 min, 20tor higher than that of derivatives. 5 (6) is then placed in a humid chamber, chlorobenzimidazole by 15-20%. Mostly they germinate at 26 ° C in the darkest stimulating effect

Within 48 hours. Corn seedlings, when exposed to seedlings of 2-day-old age, spread out 5-hydroxybenEimidazoles in concentrated paraffin concentrates with holes for 25% 1-0.1 mg / l. In these options

roots. The lids are placed on the vessels, and additional zapolzapolnenny solutions of derivatives are produced.

Table 0989344 5-hydroxybenzimndazole at concentrations of 100-0.01 mg / l. Further plant growth occurs when artificial. illumination under conditions of a 14-hour light day at 23 C. On the 7th-5th day, the main morphophysiological parameters were measured.

20 10067,7111.2

1089,2108 4

1116,0102.9

0.1122 5 91.3

0,01121.3 80.9

30 10064,5105,4

10,136.3126.1

198.3. 68.2

0,1134,5107

0,01117,5104

40 10053,6121,6

1082,6129 0

119.1 105.7

99.0 108.8

82.7

93.8 198.8 157.3

90.0 138.4 217.5 179.3

Growth,% of control

Concentrated

Lorn

mg / l

Hypocotics;

2ft, 3

138.5

121.2 107.4 122.5 104.0 The study of longitudinal sections of the root tips at the border of the zones of stretching and differentiation allows us to trace the influence of stimulating solutions of preparations of 5-hydroxybenzimidazole derivatives on the growth of the roots of sprouts. In each embodiment, lengths of 100 cells are measured. Stimulant Concentration, mg / l BIO-201 BIO-300,1 BIO-400,1 The spectrophotometric analysis of acetone extracts of pigments from the first 2 leaves of seedlings was carried out. sprouting on solutions of BIO-20 Stimulus TORContent cfl

0.718

Control 0,899 BIO-20

Continued table. one

Phytomass,% of control

Roots I of the Aerial Part

223.3 136.8 132.1

2.63

0,292 0,996

3.27 0.275 1.17 The data presented in table. 2, indicate the stimulating effect of the tested drugs on the growth of cell expansion in the root. The greatest stimulating effect is observed in the case of treating the roots of maize seedlings with a solution of BIO-20 at a concentration of 1 mg / l - 146.8% relative to the control. J Table 2 The length of the cells at the root,% to control 146.8 122.0 125.9 (results are averaged from 3 replications). The content of chlorophyll d and 6 are given in table. 3. Table 3 of chlorophyll, mg / g wet weight 5 | 01 + 5y / B

The results show that an increase in the total amount of chlorophyll occurs due to an increase in the amount of chlorophyll sk in the test samples compared to the control samples. j

Example 5 .. Seeds of millet (variety Podolskoye 24/273), 15 years old, partially germinated.

germinated in a thermostat in the dark in Petri dishes on 100 gat. on a plate on filter paper in solutions of 5-hydroxybenzim1azhazol derivatives (10 ml of solution in each plate).

On Day A, an analysis of the number of germinated seeds is carried out (Table 4). The repetition of the experiment is 4 times,

Table 4

Claims (2)

, 4-aminomethyl derivatives 2-methyl-5-hydroxybenzimidazole of the general formula -o about with growth-promoting activity. WITH 00 WITH with one