(2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)- aminocephalosporanic - antidote herbicide hormonal action 2.4-dichlorophenoxyacetic acid

 

(57) Abstract:

Describes (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic that exhibits properties of safener to herbicide hormonal action of 2,4-dichlorophenoxyacetic acid in sunflower seedlings. The technical result consists in obtaining the compounds used in agriculture to protect crops from the negative effects of herbicide. table 1.

The invention relates to new biologically active chemical substance of some heterocyclic compounds of the formula I

showing property to weaken the toxic effect of the herbicide hormonal action of 2,4-dichlorophenoxyacetic acid (2,4-D) on seedlings of sunflower. (2-Benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic I is representative of a new conjugated heteroaromatic system.

The prototype property of the connection 1 with antidote activity in relation to 2,4-D is 2-(n-aminobenzoylamino)-5-ethyl-1,3,4-thiadiazole of the formula II (patent No. 2040898. The antidote herbicide hormonal action of 2,4-dichlorophenoxy-acetic acid// the

The present invention is to expand the Arsenal of biologically active substances obtained synthetically, for use in agriculture to protect crops from the negative effects of herbicides.

This is achieved by using the compounds (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic I by treating the germinated seeds antidote.

The invention is illustrated by the following examples:

Example 1. The way to obtain (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic

Synthesis of compounds (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic I are not described in literature.

Compound I was obtained by interaction of 3-azido-2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridine (IV) by the reaction of triphenylphosphine

Azide IV was obtained from 3-amino-2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridine by reaction

The method of obtaining 3-azido-2-benzoyl-6-methyl-4-ethoxymethylene-[2,3-b]pyridine (IV).

1,69 g (0,005 mol) of a substance III (TPL137-C) was dissolved in 12 ml of glacial acetic acid, d is their portions, made a solution of 0.48 g (to 0.007 mol) of sodium nitrite in 2 ml of water. Was stirred for 20 min, then neutralize the excess of nitric acid urea (control ikramullah paper) and added dropwise during 10 min was injected solution and 0.46 g (to 0.007 mol) of sodium azide in 2 ml of water. Continued stirring for one hour. Then the reaction mass was slowly poured into the water with finely crushed ice. The residue azide IV was separated, washed on the filter with cold water until neutral wash water, dried over concentrated sulfuric acid. Yield 74%, Tpl.=115...117S (with decomposition).

Elemental analysis for C17H14N4O2S:

Found, %: C, 60,45; N, 4,19; N, 16,52.

Calculated, %: C, 60,34; N, To 4.17; N, 16,56. Range PMR (DMSO-d6): to 2.65 (3H, s, CH3), of 3.54 (3H, s, och2), to 4.87 (2H, s, och2), 7,41 (1H, s, HPy), 7,45...7,83 (5H, m, HPh), X , cm-1: 2210 (N3), 1625 (C=O).

The way to obtain (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic (I).

The solution to 3.38 g (0.01 mol) 3-azidation-[2,3-b]pyridine IV in 100 ml of benzene was added 2,62 g (0.01 mol) of triphenylphosphine. The reaction mixture was stirred until the termination of allocation of gas bubbles is whether in vacuum, the residue was rubbed out with diethyl ether. The resulting crystals were filtered off, washed with benzene and dried in the air. The product was recrystallized from a mixture of alcohol-dimethylformamide. The total yield 3.2 g (56%).

Elemental analysis for C35H29N2PS:

Found, %: C, 73,38; N, 5,10; N, 4,86.

Calculated, %: C, 73,41; N, 5,10; N, 4,89. Range PMR (DMSO-d6): of 2.53 (3H, s, CH3) and 3.15 (3H, s, och3), 4,96 (2H, s, och2), 6,87-a 7.85 (N, m, NPyCPh), X , cm-1: 1590 (C=O), 1105, 1070 (C-O-C).

Example 2. The study antidote activity (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic to 2,4-D.

Antidote activity (2-benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic to 2,4-D 500 BP BASFI (GR No. 582313-1) was studied in laboratory conditions on seedlings of sunflower varieties VNIIMK-8883. The claimed compound and the prior art (2-(n-aminobenzoylamino)-5-ethyl-1,3,4-thiadiazole) experienced in the form of solutions, the alcohol content in which was 0.2%, the content of the claimed compounds and the prototype was 10-2-10-5% (by weight).

Sprouted sunflower seeds were subjected to exposure to 2,4-D and antidote. H is the further germination was carried out at a temperature of 28C, within 3 days we measured the length of the hypocotyl and roots of sunflower seedlings.

Antidote activity was evaluated by increasing the length of the root and hypocotyl of seedlings in the embodiment, the herbicide + antidote in comparison with herbicide option (standard). In parallel were tested prototype - 2-(n-aminobenzoylamino)-5-ethyl-1,3,4-thiadiazole.

Statistical processing of experimental data carried out using t-student test at the confidence level P=0.95. The test results presented in the table.

As follows from the table, the claimed compound 1 reduces the toxicity of 2,4-D for seedlings of sunflower, surpassing the prototype 2. So, acting in concentrations of 10-2-10-5%, the claimed compound 1 increases the length of the hypocotyl at 14-35%, root - 48-84%, while prototype 2 in the same concentrations increases the length of the hypocotyl 5-9%, root - 23-32% compared to 2,4-D.

Connection 1 in the optimal concentration of 0.001% in the largest extent reduces the toxic effects of 2,4-D on sunflower seedlings, resulting in increasing the length of the hypocotyl 35% of the root - 84% compared to 2,4-D.

Thus, compound 1 exhibits properties is of CIDA 2,4-D in plants and activation of their growth.

(2-Benzoyl-6-methyl-4-ethoxymethylene[2,3-b]pyridinyl-3)-aminocephalosporanic formula I

showing antidote activity to herbicide hormonal action of 2,4-dichlorophenoxyacetic acid in sunflower seedlings.

 

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