Salt triazinetrione acids with astragalina activity against plant and tool based on them

 

(57) Abstract:

Salt triazinetrione acids with astragalina activity against plant and tool based on them. The invention relates to the field of chemistry and agriculture. The obtained water-soluble effective poststimulatory with a wide range of actions - derivatives of s-triazine of the General formula:

< / BR>
R - lower alkoxy, di(lower)alkylamino or diphenylamino, R= NH+4, K+, Na+that can be used as postregulation and means for presowing treatment of seeds based on them. The synthesis is performed by the interaction of the corresponding 2-substituted-4,6-bis(4-carboxyphenoxy)-s-triazines with an aqueous solution of the corresponding alkali or ammonia at a molar ratio of 1:2. 2 S. p. f-crystals, 2 tab.

The invention relates to the field of chemistry and agriculture, and in particular to substituted SIMM-triazines as postregulation and means for pre-processing based on them.

Known application of IAA (indelicacy acid) as a stimulant for germination of seeds of fruit and berry crops, consisting of pre-soaking seeds in 0.001% is, 990, S. 11).

Disadvantages of its use are the need of bodrstvovaniya in alcohol (due to poor solubility in water), relatively high cost (1.5 million rubles per kg on 01.12.93), a narrow range recommended for seed treatment and low photoregulatory activity.

It is also known application of Symm-triazinetrione acids as curing adhesive compositions (ed. St. USSR N 836068, B. I., 1981, N 21). The use of such acids as poststimulation unknown.

The purpose of the invention the receiving water soluble, effective poststimulation with a broad spectrum of activity and relatively inexpensive.

This goal is achieved by obtaining new derivatives of s-triazine, namely salts triazinetrione acids (Sebacina-11) General formula:

< / BR>
where R= OCH3N(C2H5)2N(C6H5)2; R=NH+4, K+, Na+; which can be used as postregulation and means for presowing treatment of seeds on the basis of them.

Source triazinetrione acid synthesized by the interaction of 2,4-dichloro-6-substituted-s-triazines with an aqueous-alkaline solution of 4-oksibenzoynoy kislota when the criterion acidification and acid secretion by a known method (Pogosyan, M. Assadourian I. A. Zaplishny Century. N. AWP. chem. W. 1977, T. 30, N 7, S. 597-601).

Synthesis of salts Curaxin-11 were carried out by the interaction of 2-substituted-4,6-bis(4-carboxyphenoxy)-s-triazines with aqueous solutions of the corresponding source of alkali or ammonia at a molar ratio of acid: Osnovnye:2, followed by Visaginas salt, alcohol, or acetone by a known method, at 20oC (E technique. Scientific-technical collection of Materials. M. 1970, vol. 2, S. 76-81).

Example 1. 2-Methoxy [4,6-carboxylations(sodium)] -1,3,5-triazine (Curaxin-11a).

To a suspension of 3.84 g (0.01 mol) of 2-methoxy-4,6-bis(4-carboxyphenoxy)-1,3,5-triazine in 8 ml of water under stirring at a temperature of 20-25oWith added dropwise 3 ml of an aqueous solution containing 0,78 g (0,0195 mol) sodium hydroxide. The mixture is stirred for 1.5 h and filtered. The filtrate, under stirring, slowly added dropwise at 30 to 35 ml of ethanol, and the precipitated residue was filtered, washed with 2x5 ml of ethanol and dried in vacuum at 50-60oC to constant weight. Get 3,82 g (89%) Sebacina-11a in the form of a pale yellow powder, soluble in water and DMF insoluble in other organic solvents.

Analysis for C18H11N3Na2O-); 1580, 1550, 1525, 1500, 1490 c. and cf. (C=C and C=N-t.); 1205, 1150, 1120, 1100, 1090 (COC): 805 SL. (deformation of 1,4-disamis. benzene).

Example 2. 2 Diethylamino [4,6-carboxylations(sodium)]-1,3,5-triazine (Curaxin-11b).

Under conditions analogous to example 1, from 4.2 g (0.01 mol) 2-diethyl-amino-4,6-(4-carboxyphenoxy)-1,3,5-triazine, 0,78 g (0,0195 mol) sodium hydroxide in 15 ml of water, with the only difference that the target salt wikidot plus water filter in 25 ml of acetone, get 4,34 g (94%) Sebacina-11b in the form of a white powder, soluble in water and insoluble in organic solvents.

Analysis for C21H18N4Na2O6:

Calculated C 53,9; H 3,9; N 12,0;

Found, C Of 53.7; H 3,7; N 12,2.

X, n, cm-1(group): 1645-1625 ush.CL. (COO-); 1595, 1560, 1530, 1500 S. and Ms. (C= C and C= N-t. ); 1230, 1200, 1165, 1135, 1065 (COC); 803 SL. (deformats. fluctuations 1,4-disubstituted benzene).

Other examples of synthesis, outputs, and properties of the synthesized salts of Covaccine-11 are presented in table. 1.

The salts triazinetrione acids (Kovaciny-11) is used as a means for presowing treatment of seeds with different crops, as poststimulatory. When preparing aqueous solutions of salts of the concentration of the p indolyl-acetic acid (IAA) concentration of 0.001 wt. which was prepared previously podesteria IAA in ethanol. As control was used the option of soaking seeds in distilled water.

The use of Covaccine-11 as a means for presowing treatment of seeds with different crops, the concentration and properties of the seedlings are illustrated by the examples presented in table. 2. The seeds were germinated in Petri dishes on constantly moist filter paper at 20-21oC for 25 days; corresponding measurements of root length and seedling conducted after 5 and 10 days, and the number of germinated seeds judged germination.

From the data table. 2 shows that all the proposed salt are growth-stimulating activity. In the case of seeds of cucumber (examples 10-26) presowing cultivation of seeds Covaccine-11 at concentrations of 0.01 and 0.0001 wt. by the slight improvement in germination compared to the control (100% instead of 97,3% ) provides an increase in the length of 10-day-old seedlings and roots (17,0-33% and 2-11,9% respectively), while poorly soluble in water IAA at concentrations an order of magnitude higher (i.e., at a higher flow rate) stimulates these indicators only at 10.0 and 1.0%, respectively.

If samajist in comparison with the control (100% instead of 97,3%) provides an increase in the root length of 10-day-old seedlings 2.2-87% while the IAA germination of seeds of melons do not stimulate.

In the case of rice seeds (examples 44-60) pre-treatment with Sebacina in conc. of 0.01 and 0.0001 wt. provides increased germination (80-92% instead of 79%) and an increase in the length of 10-day-old seedlings and roots (3.9-12.9% and 3.3% and 19.4% respectively), while the IAA even at concentrations much higher these parameters does not improve.

In the case of oats (examples 61-78) pre-treatment with Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. provides improved germination in comparison with control (11-32% instead of 9%) and increases the length of the 10-day-old seedlings and roots (7.7-78% and 17.7-94.3%), while the IAA even at concentrations much higher on these parameters has no effect.

In the case of seeds eggplant (examples 79-95) pre-treatment with Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. provides improved germination in comparison with control (68-76,7% instead of 66%) and increases the length of the 10-day-old seedlings and roots (8.4-37,8% and 4.3 is 25.2%, respectively), while the IAA on the length of the root is generally not affected, and the length of the seedlings at a concentration of 0.001 wt. increases only by 3.7%

In the case of pea seeds (examples 96-110) processing Sebacina-11 at a concentration of from 0.01 to 0.0001 wt. virtually no effect on Park the IAA on this parameter have little influence.

Thus, the proposed connection and means for presowing treatment of seeds are more effective than their counterparts on the structure and use and allow you to get available and soluble in water postregulatory, and seed treatment of their aqueous solutions can improve the germination of seeds and to increase the length of shoots and roots of various crops.

1. Salt triazinetrione acids of General formula

< / BR>
where R is lower alkoxy, di(lower)alkylamino or diphenylamino;

R' K+, Na+or NH4+,

with astragalina activity against plants.

2. Growth stimulating agent for pre-treatment of seeds, comprising the active substance and water, characterized in that the active substance it contains a connection on p. 1, where R is methoxy, diethylamino or diphenylamino, R' K+, Na+, NH4+, in the following ratio, wt.

Active substance 0,0001 0,001

Water The Rest

 

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