Amides tetrachloroquinone acid

 

(57) Abstract:

The invention relates to new biologically active compounds that can be used as plant growth regulators. The inventive new amide derivatives tetrachloroquinone acid containing at N - atom of the amide group as Deputy unsubstituted or substituted methyl group, pyridyl or pyrimidyl. Compounds stimulate the germination and yield of wheat. table 2.

The invention relates to new biologically active compounds, specifically to N-(pyridyl-2)-(I) and N-(4,6-dimethylpyrimidin-2)-tetrachloroquinone(II) General formula:

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which can be used as plant growth regulators.

These compounds, method of their production, properties and application are not described in literature.

It is known the use of amides pyridineboronic acids as postregulation (U.S. patent N 4347075, 1982). In the patent above patterns and examples of syntheses similar to the claimed compounds, but there are no specific examples of methods for biological use.

As an analogue of the claimed compounds on structual, N. C. Climer. Physico-chemical properties of pesticides. M. "Chemistry", 1976, S. 198).

Compared with the claimed compounds nicotinic acid has a narrower range of applications.

The aim of the present invention is to find new compounds, amide derivatives tetrachloroquinone acids having high astragalina activity. This goal is achieved by the synthesis and use of heterocyclic amides tetrachloroquinone acid reactions

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where X=CH, N;

Y=H, CH3, Z-H.

The original acid chloride THNK synthesized by the known method of U.S. Pat. USA N 3766195, 1973; 2-amino-4,6-dimethylpyrimidin by the method of: Scars L. C. Bychkov A., Synthetic chemical-pharmaceutical preparations. M. "Medicine", 1971, S. 136.

Below are examples of synthesis of these compounds.

Example 1. Synthesis of N-(pyridyl-2)tetrachloroquinone (I, X=CH, Y, Z= H).

To the mixture and 2.79 g (0,010 m) of the acid chloride THINK, 0,94 g (0,010 m) ortho-aminopyridine in 46 ml of anhydrous dioxane is added dropwise 2 ml of 0.014 m) of triethylamine in 10 ml of dioxane is heated at 50oC 6 h under stirring, the precipitate is filtered off, washed with water, obtain 1.22 g of yellow Kristallnacht (I), the yield of 53.7% So pl. 281 282oC (dioxane). Sparingly soluble in dimethylformamide, dimethylsulfoxide, is poorly soluble in dioxane, acetone, insoluble in water, heptane.

Found, C 39,46; H 1,60; N 12,16; Cl 43,07.

Calculated C 39,17; H 1,48; N 12,46; Cl 42,14.

X cm-1: C=C, C=N 1600, 1620, C=O 1700, C-H 3050, N-H 3120 (vaseline oil, ghri).

Example 2. Synthesis of N-(4,6-dimethylpyrimidin-2)tetrachloroquinone (II, X=N; Y, Z=CH3).

To a mixture of 2.46 g (0,020 m) 2-amino-4,6-dimethylpyrimidine and 5.58 g (0,020 m) of the acid chloride THINK in 60 ml of chloroform was added dropwise 2 ml of 0.025 m) of pyridine in 20 ml of chloroform. Heated with stirring at 60oC for 2 h, the Reaction mass is evaporated, the residue was washed with water and heptane. Get 6,56 g of a beige powder, the yield of 89.6% of So pl. 175 177oC (CH3COOH-H2O). Soluble in dimethylformamide, dimethylsulfoxide, acetic acid, insoluble in water, heptane.

Found, C 38,70; H 2,70; N 15,34; Cl To 39.34.

Calculated C To 39.34; H 2,18; N 15,30; Cl 38,80.

X cm-1C=C, C=N 1560, 1610; C=O, C=N 1670, 1690; C-H 2930; N-H 3150 (vaseline oil, ghri).

Below are examples confirming the activity of the claimed compounds.

Example 3. Wheat seeds, cucumbers within 8 h zamac the s diameter 25 cm Each option was presented with 4 replications. Accounting efficiency was determined by germination, growth energy of seeds, weight and length of the plants 3 weeks after sowing. The results are shown in table. 1. The data table. 1 show that the substances have astragalina activity.

Example 4. Wheat seeds were soaked in an aqueous solution of the inventive substances for 8 h at a concentration of 1 mg/L. Then the seeds were sown in experimental plots measuring 2 m2. Sowing was conducted in early may, the cleaning in the middle of September. During the vegetation was conducted phenological observations. Repeated 4 times. Soil plots podzolized Chernozem soil with relatively high humus content of 8.6 to 8.8% heavy mechanical composition. pH 5.2. The results are given in table.2. The data table.2 show that the drugs increase the yield of crops.

Thus, the tests have shown that the claimed compounds have astragalina activity. This effect in increasing the germination, growth energy of seeds, increasing yields.

Amides tetrachloroquinone acid of formula I:

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where X is CH, N:

From hydrogen, methyl,

manifesting stimulating R is

 

Same patents:

The invention relates to compounds of the formula

(I)

where R1represents hydrogen, lower alkyl, lower alkenyl, lower quinil, aryl lower alkyl, cycloalkyl lower alkyl, lower alkoxy lower alkyl, hydroxy lower alkyl, amino lower alkyl, mono - or di-lower alkyl, amino lower alkyl, formyl, lower alkylsulphonyl, amino lower alkylsulphonyl, lower alkoxycarbonyl, mono - or di-aryl-substituted lower alkyl, arylcarbamoyl lower alkyl, aryloxy lower alkyl, or lower alkylene

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X represents O or S;

W represents hydrogen, halogen, hydroxy, lower alkoxy, aryl lower alkoxy, nitro, trifluoromethyl or

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where R3represents hydrogen, lower alkyl or aryl lower alkyl, and R4represents lower alkyl or aryl lower alkyl; or alternatively the groupas a whole represents the

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R5is hydrogen, lower alkyl, aryl or aryl lower alkyl; and

Z predepression

The invention relates to organic chemistry, in particular to a method of obtaining an individual stereoisomers of 4-diprosone glutamic acid of General formula

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ALK is a lower alkyl

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