N-(-alkoxyalkyl)caprolactam with protecting and aerorepublica activity

 

(57) Abstract:

Usage: biological active substances, derivatives of E - caprolactam with protecting and aerorepublica activity. The inventive product is N - a-alkoxyalkyl/caprolactam, the General formula where R is H, CH3. Reagent 1: N-methylacetoacetyl or caprolactam adduct with an aldehyde reagent 2: hexyl alcohol. Reaction conditions: stirring 3 h in an environment of benzene with a catalyst hydrochloric acid, neutralization with soda and distilled in vacuum. N - hexyloxymethyl/caprolactam, BF C14H27NO2exit 41%, so Kip. 131 - 134° /SMM. table 1.

The invention relates to new biologically active compounds, namely N-( -alkoxyalkyl)caprolactam General formula

N - H - OC6H13where R is H, CH3with insect - and aerorepublica activity.

The closest structural analogues of the claimed compounds are N-( -alkoxyalkyl)caprolactam (1-3), which are used as intermediates to obtain tert-N-vinylamides carboxylic acids and N-vinylation.

Functional analogue is diethyltoluamide(DETA) (4), showing insectrepellent action.

Currently, the range of applied repellents effective aerorepublica not available.

The proposed N-( -alkoxyalkyl)caprolactam receive the following way:

N-( -hexyloxymethyl)caprolactam is produced by interaction of N-methylcaprolactam with hexyl alcohol in the presence of catalytic amount of conc. HCl at room temperature; N-( -hexyloxymethyl)caprolactam is produced by interaction of caprolactam with acetaldehyde and hexyl alcohol in the environment of benzene in the presence of conc. H2SO4at room temperature.

P R I m e R 1. Obtaining N-( -hexyloxymethyl)caprolactam.

The mixture 28,64 g (0.2 mole) of N-methylacetoacetate, of 124.8 ml (1 mol) of hexyl alcohol and 0.4 ml of conc. HCl is stirred for 3 h Then the reaction mass is diluted with water, neutralized 2n. NaOH to pH 9, extracted with benzene. The benzene extract was separated, washed with water. The benzene is distilled off. After vacuum distillation of the residue receive 40,83 g (90%) of N-hexyloxymethyl in the form of a colourless liquid with so Kip. 142-148aboutC/4 mm, nD201,4680, d4200,9709.

Found,%: C 68,90; N IS 11.11; N 6,51,13H25NO2.

Calculated,%: C 68,68; N 11,08; N 6,16.

C=Oat 1655 cm-1and simple ester groupC-O-Cwhen 1080-1100 cm-1.

P R I m m e R 2. Obtaining N-( -hexyloxymethyl)caprolactam.

To a solution of 25 g (0,22 mol) of caprolactam, 14.5 g (of 0.33 mole) of acetaldehyde and 33 g (of 0.33 mole) hexyl alcohol in 125 ml of benzene at room temperature and stirring, slowly add 1 ml conc. H2SO4. The mixture is left for 33 hours at the same temperature. Then the reaction mass is washed with a solution of potash, water. After removal of the solvent the residue is distilled in vacuum. Get 22 g (41%) substances with so Kip. 131-134aboutC/3 mm; nD251,4639; d4200,9649.

Found,%: N 5,39.

WITH14H27NO2.

Calculated,%: N 5,80

In the IR spectrum of compound has absorption bands:C=0at 1650 cm-1andC-O-Cwhen 1100-1105 cm-1.

The biological activity of the claimed compounds was studied under laboratory conditions when applying products on cotton diagonal in the amount of 20 g of active substance per 1 m2. As biotests used the mosquitoes Aedes aegypti and fleas Xenopsilla cheopis, field - mosquito natural populations of A. communis, dominant in the Moscow region and party of the studied compounds was expressed by the coefficient of deterring actions (CODE) by the formula 100 (A-B)/A, where a is the number of mosquito landings for 5 min to test the control (untreated) fabric B on the test fabric treated with the drug. In the case of experiments with ticks and fleas: a - the number of fleas or ticks remaining after a certain exposure on a clean (control) sample, B is the same on impregnowana sample.

The CODE was determined after 1 day and after treatment of the fabric and then every 1-2 weeks to decrease the CODE up to 70%.

Acute toxicity to warm-blooded animals was determined by means of a single injection of the drug in the form of oil solution in the stomach to white rats. Statistical data processing was carried out according to the method of Cerberus.

The results of the tests of repellent activity are presented in table. 1 and 2.

Results of the tests show that the claimed compounds have a strong repellent effect on mosquitoes, fleas and ticks. The increased duration of the repellent action can significantly reduce the frequency of treatments, which is economically advantageous for the protection of farm animals from blood-sucking insects.

The level of toxicity of the compounds are toxic substances.

Appl is but a simple and environmentally friendly; all raw materials refers to large-scale products of the chemical industry.

N-( -Alkoxyalkyl)caprolactam General formula

N - H - OC6H13where R is H, CH3< / BR>
where R is H, CH3,

with insect - and aerorepublica activity.

 

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The invention relates to new biologically active compounds, namely N-(-alkoxyalkyl)caprolactam General formula

NH - OR1where R=C3H7when R1=C2H5-C4H9with insectrepellent activity

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SUBSTANCE: the present innovation deals with obtaining N-(2-chloroalkyl)- and N-alkyl-aromatic derivatives of lactams of the following general formula: , where R=H, Cl, R'=(CH2)3, (CH2)5 which could be modifiers of unsaturated carbon-chain caoutchoucs and rubber mixtures based upon them. The suggested method for obtaining the mentioned N-substituted lactams deals with combining N-chlorolactams and allyl benzene, moreover, as N-lactams one should apply either N-chlorobutyrolactam or N-chlorocaprolactam. The process should be carried out at molar ratio of N-chlorolactam to allyl benzene being equal to 1-1.15:1, at availability of a catalyzer as mono-tertiary-butylperoxy-α-methylmethoxyethoxyethyl ether of ethylene glycol taken at the quantity of 0.4-4.0% weight, in the medium of inert solvent, for example, chlorobenzene at 100-125° C for about 15-20 min. The innovation enables to shorten terms of reaction by 20-30 times, simplify the way for obtaining target products and widen the assortment of the obtained compounds, as well.

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EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved methods for synthesis and preparing.

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57 cl, 62 ex

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10 cl, 5 ex, 1 tbl

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15 cl, 3 tbl, 18 ex

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19 cl, 12 ex

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1 ex

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EFFECT: providing a selective ammoximation method.

11 cl, 5 tbl, 6 dwg, 16 ex

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