RU1148303C - Dimethylphosphate of dimethyl-bis-(oxiethyl)ammonium processing growth-controlling activity - Google Patents

Description

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The invention relates to CHEMISTRY of phosphorus compounds, in particular to new dimethylphosphoric dimethyl-6is- {hydroxyethyl) ammonium of the formula I

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SNGSHGON a. CH HAPPY

which has growth regulating activity and can be used in agriculture:

It is known to use, as plant growth regulators, orthylphosphonic acid (etrel), kinetin and chlorocholinchloride (CCC).

Closest to the described compound in structure and purpose is dimethylphosphate M M-dimeti piperidini (dipiphos); However, this compound does not exhibit insufficient growth regulating activity.

An object of the invention is to increase the activity of plant growth regulators.

The goal is achieved by the compound of formula I, the growth-regulating activity of which is higher than that of the known compounds.

A compound of formula I is prepared by reacting methyldiethylamine with trimethylphosphate in an organic solvent.

The structure of compound I was confirmed by elemental analysis and IR spectroscopy. In the IR spectra, absorption bands characteristic of OH-valence vibrations (3400-3350 cm and for the phosphorus group vibrations (1180

CMV

PRI me R 1. Obtaining dimethyl phosphate dimethyl bis oxyethyl) ammonia.

A mixture of 11.9 g (0.1 mol) of 14-methanol 1 ethanolamine and 14.0 g (0.1 mol) of trimethyl phosphate was left for two days at 20 ° C in benzene, the reaction mixture was separated, the lower layer was separated, washed with benzene get 20 gs of Union I. Yield 77%; ps 1.4720.

Found%: C 36.85; 36.79; H 8.15; 8.21: N, 5.63; 5.65; P, 14.58.111.72.

C8H22N06P.

Calculated,%; C 37.06; H 8.55: N 5.40; P 11.94.

Example 2. Tests on seedlings of wheat and barley.

Wheat and barley seeds are germinated for two days in an incubator at 24 ° C on

important filter paper. Identical seedlings are planted in the openings of vinyl plastic covers on vessels with tap water with a volume of 300 ml,

10-12 plants per vessel, two vessels per option. After 4 days, the water in the vessels is replaced by a solution of mineral salts of Ca (MO3) 2 1.33 g / l, KH2P04 0.33 g / l, 7H2 0.17

G / l containing the test substance in a given concentration. Control - a solution of mineral salts without preparation.

Wheat and barley seedlings are grown for 18 days at a temperature of 24–25 ° C, illumination of 6–8 thousand, lux, daylight length of 18 hours. At the end of the specified period, each plant measures the distance from the base of the stalks to the base of the first leaf and from the base first sheet to the base

second sheet. At the same time, the total wet weight of the aerial part and the roots in each vessel is determined. The results of the experiment are given in table 1.

Example 3. Tests on plants

arabidopsis.

Arabidopsis is grown in test tubes on a sterile agarized nutrient medium containing 0.7% agar, KyOz 1 g / l, Ca (0.5 g / l, AHGRO 0.15 g / l. MgS047N200, 15 g / l, ethylenediamitraacetic acid 0.035 g / l, FeSO4 0.07 g / l, microelements and the test sample at a given concentration Growth mode 18 hours of light day, lighting 7-8 thousand

lux, temperature 24-25 ° С. In each tube, 7 ml of agar medium was added; after Hardening, 1 seed of Arabidopsis was placed on the surface of the agar. The tubes are incubated for 2 days at 4 ° C and then transferred

on the light of the installation. Accounting is carried out 30 days after the start of the experiment. The length of the root system and the stem of each plant, the total wet weight of the aboveground Mass per variant are determined. At the beginning of flowering, the number of flowering plants per variant is taken into account each day. The repeatability is 12-fold; counting is carried out on the five most uniform plants. The results are shown in table.2.

PRI me R 4. Tests on lettuce seeds.

Lettuce seeds are placed in Petri dishes and filters moistened with a solution of the test substance. Cups are placed in

thermostat at 30 ° C; after two days, the number of germinated seeds is counted. The repetition is 4%. In this test, the ability of the drug to stimulate seed germination under conditions is shown.

thermo-induced rest. The test results are shown in Table 8.

PRI me R 5. Tests on wheat seedlings - test for increasing drought tolerance.

Wheat seeds are germinated in thermostat at 24 ° С for two days. Identical wheat seedlings are placed in rolls of filter paper, immersed with the lower end in the solutions of the tested preparations, and grown for eight days under illumination of 5-6 thousand; lux, temperature 24-25 ° С. The first leaves of the seedlings are cut, placed in cuvettes loosely closed with glass and set for drying in a thermostat for 24 hours at 24 ° C. Before and after drying, the leaves are weighed to determine the amount of evaporated water. After year-drying, the leaves are placed for 2 hours in distilled water. The electrical conductivity of distilled water determines the release of electrolytes by wheat leaf cells. Isolation: electrolytes are an indicator of damage to cell membranes as a result of neutralization. Decreased ejekUrolit yield compared to coytrol (cultivation on water without a drug) CBMfleTeftbCTByet on increased cell resistance to resistance to resistance;

Chlorocholine chloride is used in the hetalonime dyr test. 1 Test results are applicable. 4. ;.:; AND;;;; ,; . at.

It should be noted that the known growth regulators in the type of action are different from the declared unity and etrel and dipiphos are retardites, i.e. their growth is shown to be more active in shortening the stalk. The most sensitive to them are monocotyledons; as can be seen from the table. 1. In low concentrations, an incentive is observed for the growth of the superficial part of i-Roots, and in a high test for wheat seedlings

inhibition and even toxic effects. The dicotyledonous plant Arabidopsis is less sensitive to dipiphos, and the retardant effect of etrel is accompanied by root inhibition and a significant developmental delay (see table 2).

The claimed compound is also a retardant, the action of which is strongly manifested on wheat (although inferior

standard) and does not appear on barley and arabidopsis. However, the main manifestation of the growth-regulating properties of the proposed compound lies in the stimulating effect on the growth of the aerial part and especially root system. In this regard, the test compound is superior to etrel and dipiphos wa of all three plant species, and the stimulating activity is manifested in the entire concentration range, not

change toxic effect at high concentrations.

The test on lettuce seeds gives an additional characteristic of the biological properties of the test compound.

In the stimulation test, it, like etrel and dipiphos, reaches the kinetin level for which this test is specific.

The claimed compound also has

the ability to increase the resistance of wheat plants to dehydration and on the level of the CCC standard.

(56) U.S. Patent No. 3B12217, CL. 260-924,

published. 1974.

Muller S.O. Kunettn and Klnetln like compaunds. Moderrx Methoden der Pflahzenanalyse. 1963, Berlin, Springer Verlag, s. 198.

Melnikov N.N. and other chemical plant protection products. M ;; Chemie, 1980, p. 118,

Table 1

Continuation of table 1

 The difference compared with the control is significant.

Tests on Drabidopsys plants

Tests on lettuce seeds

Table 14 a 2

Table 3 Test for increasing drought tolerance of wheat seedlings

Continuation of table 3

Table 4