SU1372877A1 - N,n,n-trialkyl-n-6,6-dimethyl-bicyclo/3,1,1/-heptene-2-yl-2) methyl ammonium bromides displaying retardant activity - Google Patents

Abstract

The invention relates to polycyclo. ammonium compounds, in particular N, N, H-trialkyl-H- f (6, b-dimethylbicyclo 3, I, O hepten-2-ip-2) methyl ammonium bromides of the total f-ly SNoAbg ki e; A- - Asn,), to; I: (CH2) 5-W-K, K- (CHg), CH3; BUT -. -N® (CH,) j - (CH,) in SI, or,) j, (CH), SI, which exhibit the properties of retardants and can be used in medicine. The goal is to create new more active substances of the indicated class. Synthesis will be carried out from the corresponding amine and alkyl bromide in the medium of boiling f-la: a) 75; 183-185; C ,, H4iBrN; b) 76; 154-157; Ca, H, VgN; c) 68; 159-162; d) 72; 142-145; Cj. New substances exhibit activity at concentrations of 50–200 mg / l, have a better indicator of physiological activity (20.9–26.8 for wheat and 3.5–6.2 for barley), under their action the process of photosynthesis is intensified and C1 € thickening of bley grains and watercress. 4 tab. ethanol at yield, Z; m.p. GrossS (L

Description

The invention relates to quaternary ammonium salts, specifically N, N, N-TpiianKHn-N- (6,6-dimethyl and bicyclic, 1, O-het1tei-2-yl-2) methyl) ammonium Iiibromidam general formula p ,,

 “B

(

(Shz (L 5 (ciss) 2 sip

((CH21BSNzt

or

 1) (CH2) 9CH-i

developing properties of retardants that can be used in agriculture.

ten

3728772

using chromatography in a chloroform-methanol (3: 1) system on a sil- uole. Their structure was confirmed by elemental analysis and IR spectra.

The biological activity of the compound is studied in concentrations of 50; 100 and 200 mg / l in tests on wheat seedlings (variety Luch) and barley (variety Cyclone) and in concentrations of 5; 10 and 25 mg / l in the test for hypocotyl x cress.

A bioassay for cress x cress is performed in Petri dishes, at the bottom of which a layer of sterile cotton 4-6 mm is placed moistened with 20 ml of a solution of the test compound prepared in phosphate buffer (pH 6.0-6.4). On cotton wool, you will see seeds of a press salad (20 seeds per each cup) and thermostatic for 24 hours at 31 ° C. Then pour Knopp nutrient solution (5 ml in each cup), open cups are transferred to

1G

20

The purpose of the invention is to provide you with 25 cuvettes of water.

new quadruple ammonium salts exhibiting enhanced retardant properties.

The invention is illustrated by examples.

Example 1, A mixture consisting of 2.0 g (0.011 mol) N, N-dimethyl-N-pinenylamine, 5.9 g (0.03 mol) of 1 - octyl bromide in 18 ml of dry ethanol is heated in reverse refrigerator for 7 hours. The solution is evaporated in vacuo. The residue is triturated in ether and filtered. The remaining powder is recrystallized from acetone with additions of ether. 3.15 g (76Z) of white salt II are obtained.

Examples 2 and 3. Analogously to Example I, but replacing methyl octy by 5.4 g (0.03 mol) of 1-heptyl bromide or 6.6 g (0.03 mol) of decyl bromide, 2.6 g (68%) of compound III and 3.2 g (72%) of compound IV.

EXAMPLE 4 Analogously to Example I, but using 2.0 g (0.009 mol) of N-pinylpn-peridine and 4.8 g (0.025 mol) of octylbromide as the starting material, 2.7 g (75 g %) salt crystals I.

Data analysis and characterization

The target products are listed in Table. gg. The activities of the CAS reference standard for these compounds are hygroscopic, easily soluble in water, crystalline compounds. Their individuality is confirmed by the fine grains, respectively, by 39–56% and 16–30%.

In the test for hypocotyl x watercress 5t, azan substances inhibit growth

5 cuvettes with water

shelving with illumination and temperature of 26-28 C.

0

five

which are placed on 6-8 thousand lux On the I0-th day

after the experiment was established, the length of the hypocotyl in ten medium plants from each cup was measured. Repetition is twofold (20 plants). Visually assess the intensity of color and the thickness of the stems compared with the control.

Tests on wheat and barley seedlings are carried out similarly to the previous one, with the only difference that the cups with the seeds of wheat or barley are thermostated at 29 ° C and the results of the experiment are recorded on the 5th day after the experiment was started. The experiments were carried out in comparison with the standards — known retardants: chlorocholin chloride (CCC) and 1,1-dimethyl hydrazide of amber acid — 5 (preparation of alar, or DUC). As a control, take water.

The average sprout length (or hypocotyl) is indicated as a 95% confidence interval calculated using Student's constant. The results are shown in table 2, 3 and 4 ..

As can be seen from the tables, the substance is inhibited by the growth of wheat seedlings by 44- 67%, and barley by 32-62%, which is higher

0

0

the activity of the CCC standard at these concentrations, respectively, by 39–56% and 16–30%.

In the test for hypocotyl x watercress 5t, azan substances inhibit growth

3

by 24-88%, which also exceeds the activity of standards: CCC by 14-69% and DYAK by 6-33%.

Ie table 4, it is clear that the foot compounds are more active than the CAS standard: on poganitsa 20.9-26.8 times, on barley 3.5-6.2 times and on watercress 11.1-48, 8 times. They are also more active than DYAK on the cress 2.3-10 times.

At the same time, in comparison with the analogue in structure, the new compounds exhibit increased activity in lower concentrations (50–200 mg / l versus 100–400 for known ones), have a greater indicator of physiological activity: 20.9-26.8 versus 3, 2-10.0 dp known (for wheat)), 3.5-6.2 against 1.5-2.2 for known (for barley).

The effect of the substances obtained leaves the plants acquire a dark green color, indicating the intensification of photosynthesis. In this case, the stalks of the plants thicken.

372877 .4

Claims (1)

Invention Formula M, N, N-Trialk1sh-N- | (6,6-dimethyl-5 bicyclo 3, I, 1-hepten-2-yl-2) metsh ammonium bromides of the general formula CH2AVG ten Where A- -NO (CHzVCH (.сНг) 7СНз (CH2) BSNZ 20 or (ъ} r (СН2) 9СНз 25 Proactive properties of retardants. The action of aat vta sovdigvpiy pas sprouted n with com "" chme log On seedlings shkppi 5,6 "0,1 61,7", 410.1. 4c, “6, tiO, l 46.1 6.0 t 0.1 W.S I2.4t0, l 93.0 13,340,1 iOO, 0О 8.2 10.5 66.1-83.8 On barley seedlings The effect of unsupported compounds on gnlokoti 1sress from the lat 19,740,752,0 9.6 iO, 425.3 I4,5tl, 038.3 I9.5iO, 451.5 32,510,785,8 25, 766.2 37, l T blno "2 I3,3t0, l GOO.O O 6.0-7.3 47, fr-57; 9 Table 3 100.0 37,9tl, l 100.0 Table 4 C and KVE teli physiological akhtnanosti (K,) tested in the next in sravveyi e-analogues