SU1074868A1 - Dimethoxy-(4-(2,3,5,6-tetrachloro)pyridyl)isocyanide having growth inhibiting effect - Google Patents

Abstract

Dimethoxy-4-

Description

i

00 9 X) The invention relates to a new chemical compound, specifically to dimethoxy- 4- (2,3,5, 6-tetrachloropyridyl isocyanide of the formula W C / or Hj / 2 Cf possessing growth-inhibiting activity n / , which can be used in agriculture. N, M-dimethyl-n - (2,3,5,6 tetrachloropyridyl) formamidine J | l is known. However, the growth-inhibiting effect of the known compound has not been described. In agricultural practice, the use of trimethyl-2-chloroethylammonium chloride (TUR), which has a growth-inhibiting effect, is known. The toxicity of the known compound to warm-blooded animals is mg / k. The aim of the invention is to expand the arsenal of agents with growth-inhibiting activity. This goal is achieved by a new chemical compound, namely dimethoxy- 4-(2,3,5,6-tetrachloro)pyridyl isocyanide, possessing growth inhibitory activity. The title compound is obtained by the interaction of 2,3,5,6-tetrachloropyridyl-4-imidoyl dichloride with sodium methoxide. Example 1. Dimethoxy-4 (2,3,5,6-tetrachloro)pyridyl isocyanide 1.56 g (5 mmol) of 2,3,5,6-tetrachloropyridyl-4-imidoyl dichloride are dissolved in 30 ml of absolute methanol and 0.6 g of sodium methoxide dissolved in 10 ml of methanol are added. The mixture is stirred for 5 h at room temperature. The alcohol is evaporated in vacuo, the residue is treated with water, extracted with ether, yielding 1.1 g (72%). mp 140-142°C (from aqueous isopropanol). Found, %: C 31.80, H 2.00; N 8.91, CI 6.11 .NjOj Calculated: C 31.58; H 1.97; N 9.21, CI 46.71. The IR spectrum (KBr) contains two characteristic absorption bands, one of which in the region of 1650-1680 cm-1 refers to the stretching vibration of C, the second at 1580 cm-1 corresponds to the skeletal vibrations of the pyridine ring. Example 2. Growth-regulating activity. The growth-regulating activity of the compound was studied on plant seedlings grown in Petri dishes on agar medium using the standard method (T.A. Sergeeva, 1963). Seeds are placed in Petri dishes on solidified agar containing the test substances at a certain concentration. Seed germination occurs in a thermostat at 22-24 ° C for 2 days, and then at room temperature in a fume hood with illumination. After 4 days, seed germination is determined and the length of the roots and stems is measured. Each variant has 5 repetitions (dishes). Each dish contains 10-11 plants. The average length of the roots or stems in each dish is taken into account, and then the arithmetic mean length is calculated for the replicates of the experiment. The control is the experiment with pure agar containing only water. For comparison, TUR and H,N-dimethyl-N- (2,3,5, b-tetrachloropyridyl) formamidine (compound I) were taken into account. Statistical data processing was performed using Sokolov's method. A.V. (1967). The experimental data are presented in Table 1. It was found that compound 1 has high growth-inhibiting activity in relation to mono- and dicotyledonous crops at concentrations of 0.01-0.0001%. In terms of growth-inhibiting action, the proposed compound is superior to TUR in all tested concentrations and compound P- at concentrations of 0.001-0.0001%. Example 3. Biological activity against wheat grass. The growth-regulating activity of the compound was studied on 2-day-old wheat sprouts grown in a thermostat at 23°C, with a stem length of 1.0-1.2 cm and a root length of 2.0-2.5 cm. Vessels with a capacity of 500 ml, closed with gauze soaked in paraffin, were filled with a Knop mixture containing the test substances of varying concentration. The sprouts were placed in pre-made holes in the gauze so that their root system was completely in the solution. The experimental plants were kept at room temperature and additional lighting with fluorescent lamps for 3 days. The growth-regulating activity of the compounds was assessed based on the length of the roots and stems of the plants and was expressed as arithmetic means derived from all replicate experiments. The replication was 3-fold (J jars, 10-11 plants in each jar. The experiment with pure Knop medium was used as a control, for comparison, TUR and compound P. The test results are presented in Table 2. It was found that the proposed compound surpasses TUR and compound 11 in concentrations of 0.01-0.0001% in terms of the level of growth-inhibitory effect on the roots and stems of wheat.

Example 4. Determination of toxicity for warm-blooded animals.

The acute toxicity of compound 1, compound II and TUR was determined on white mice weighing 19-21 g by intramuscular administration of emulsions of the preparations in various concentrations. Dead and surviving animals were counted 24 hours after administration of the preparation. The results were subjected to statistical processing using the Litchfield and Wilcoxon method as modified

Rota (1963). The LDjj value, the dose of a substance causing the death of 50% of animals, served as an indicator of acute toxicity. Studies have shown that the proposed compound

and compound P are classified as low-toxic compounds. Their LDp is U500 Mr/Kr,LDj(, TUR - 398 (384-404) mg/kg.

Thus, the proposed compound - dimethoxy-4-{2,3,5,6-tetrachloro)pyridyl isocyanide - has growth-inhibiting activity and is superior in terms of its level of action to the known compound in terms of structure and purpose.

Table 1

0.01 65

65 67 81 0.001 70 0.0001 85

0.01 46

81 89 97 0.001 72 0.0001 90

UR

1.0

29 98 98

15 0.1

70 0.1

101

0.001 100

101 0.0001 105 . 94

88 83 98

104

87 108

120

500 105

94

70 89 98

107

107 120 120

500 105 109

22 80 92

11 97 96

72

98

102

101

398

95 102

(384404)

92

99 90

90

95 82 07 97 Concentration % Preparation Compound 1 0.01 0.001 0.0001 Compound P 0.01 . 0.001 0.0001 ,,,,M,«B «Mn «w«AH « BB B«v «ta BB « H TUR 0.01 0.001 0.0001

Table 2 Length of plant parts,% RootStem 2364 2373 2274 . 6769 7270 6777 - - ------ - -- .-.-. ,,-..- -..- -.e- i., 8477 8484 8185

Claims (1)

Dimethoxy-[4-(2,3,5,6-tetrachloro)pyridyl] isocyanide of the formula No. ₃ 1 _g N possessing growth inhibitory activity. 1 1074868