N-(-alkoxyalkyl)caprolactam with insectrepellent activity

 

(57) Abstract:

Usage: biologically active substances, derivatives of E-caprolactam with insectrepellent activity. The inventive product - N - a - alkoxyalkyl/caprolactam General formula , where R=C3H7when R1= C2H5C3H7C4H9. Reagent 1: - caprolactam, reagent 2: oil aldehyde reagent 3: ethanol, propanol or butanol. Reaction conditions: mixing of reagents in the environment of benzene with sulfuric acid as catalyst at room temperature, exposure of the reaction mass 33 h and neutralized with soda. Distillation in vacuum. N/ a-ethoxymethyl/caprolactam, BF C12H23O2the yield is 50%, so Kip. 106 - 108°C SMM. 3 table.

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

N - H - OR1where R=C3H7when R1=C2H5-C4H9with insectrepellent activity.

The closest structural analogues of the claimed compounds are N-( -alkoxyalkyl)caprolactam (1,2), which are used as intermediates to obtain tert-N-vinyl is), showing insectrepellent action.

The goal is to find new substances exhibiting insectrepellent activity of long duration.

N-( -Alkoxyalkyl)caprolactam produced by interaction of caprolactam with oily aldehyde and the corresponding alcohols in the presence of conc. H2SO4at room temperature.

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

To a solution of 25 g (0,22 mol) of caprolactam, of 23.8 g (of 0.33 mole) of butyric aldehyde and 15.2 g (of 0.33 mole) of ethanol and 125 ml of benzene at room temperature and stirring, slowly add 1 ml conc. H2S4. A mixture of 33 h 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 to 23.4 g (50%) substances with so Kip. 106-108aboutC/3 mm; n2D51.4630; d2400.9782 .

Found, %: N 6,28.

C12H23NO2.

Calculated, %: N 6,57.

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

Similarly receive the remaining connections (see tab. 1)drugs on cotton diagonal in the amount of 40 g of active substance per 1 m2. As biotests used mosquito edes aegyti and fleas nsilla cheois field - mosquito natural populations of A. mmunis dominant in Moscow and Tyumen regions. Reference taken is known repellent DEATH metal. The effectiveness of the compounds expressed by the factor 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 fleas: a - the number of fleas remaining specific exposure on a clean (control) sample, B is the same on impregnowana sample. The CODE is determined after 1 day after treatment of the fabric and then every 1-2 weeks to achieve 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. 2 and 3.

Results of the tests show that the claimed compounds have a strong repellent effect. The increase in the length of the OTP is selskohozyaistvennyh animals from blood-sucking insects.

The claimed compounds are promising for practical use due to the fact that the retrieval method is simple and clean. All raw materials refers to large-scale products of the chemical industry.

N-( -Alkoxyalkyl)caprolactam General formula

N - H - OR1< / BR>
where R is C3H7when R1- C2H5-C4H9,

with insectrepellent activity.

 

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