CS269382B1 - Vicinal bromoalkoxyderivatives of aliphaticaromatic ethers with tetrahydrofuran cycle in the molecule as biologically active substance and method of their preparation - Google Patents

Abstract

The subject of the solution are new biologically active substances of the general formula X, where the symbol R^ denotes a straight or branched chain alkyl group with a maximum of 3 carbon atoms, the symbol R denotes a methyl or ethyl group. Their pesticidal effects have been tested, for example, on insects and mites. Another part of the solution is a method of preparing substances of the general formula I, consisting in the reaction of an unsaturated ether of the general formula II, where the symbol R has the above meaning, with N-bromosuccinimide at a temperature of 0 to 5 °C.

Description

The invention relates to vicinal bromo-alkoxy derivatives of aliphatic-aromatic ethers with a tetrahydrofuran ring in the molecule as biologically active substances and a method for their preparation.

The essence of the present invention are vicinal bromo-alkoxy derivatives of aliphatic-aromatic ethers with a tetrahydrofuran ring in the molecule of the general formula I, ci k ₀ JO-(CH ₂ ) ₄ -O-<g)-CH(OR ¹ )-CH(Br)R ² (I), where Ri denotes a straight or branched chain alkyl group with a maximum of 3 carbon atoms, R denotes a methyl or ethyl group.

The biological (pesticidal) effects of substances of general formula I have been tested, for example, on termites, where ecologically unacceptable agents, such as pentachlorophenol and the like, have so far been used to combat these pests on wood.

The method for preparing vicinal bromo-alkoxy derivatives of aliphatic-aromatic ethers with a tetrahydrofuran ring in the molecule of general formula I is characterized in that an unsaturated ether of general formula II ^P^O-(CH ₂ ) ₄ -O-@-CH=CH-R ² (II), where R has the above meaning, is reacted with an alkanol of general formula III

R ¹ OH ' (III), where R ¹ has the above meaning, and N-bromosuccinimide at a temperature of 0 to 5 °C to form the product of general formula I.

The invention is explained in more detail by way of an example of embodiment, without being exclusively limited to this example.

Example

To a solution of 0.3 g (1 mmol) of 1-(2-propenyl)-4-[4-(3-chloro-2-tetrahydrofuryl)oxybutoxy]-benzene in 5 ml of anhydrous methanol was added at 0 to 5 °C in the absence of air humidity 0.3 g (1.7 mmol) of N-bromosuccinimide. After stirring for a quarter of an hour, the reaction mixture was diluted with water and partitioned between diethyl ether and water. The separated and dried ether layer was evaporated to dryness. Chromatography of the residue on a silica gel column with 8% w/w water (eluent petroleum ether containing up to 20% w/v (diethyl ether)) gave 0.3 g (73%) of 1*-(1-methoxy-2-bromopropyl)-4*-£4-(3-chloro-2-tetrahydrofuryl)-oxybutoxyj benzene. ' ____ ¹³ C-»MR spectrum (200 MHz): 20.60 (CH ₃ ), 25.97 and 26.16 (CH _? CH _? ), 33.38 (CH^ J), 52.71 (CHBr), 57.33 (OCHO, 60.31 (C^HCl), 66.35 ^{66.90 67.38 86.73} (CHOCH ₃ ), 108.17 (l ₀ ^H), 114.04, 128.58, 130.16, 158.82 (aromatic nucleus).

MS spectrum; 420/2/4 (M ⁺ ,C ₁₈ H ₂₆ BrC10 ₄ ), 313(C ₁₆ H ₂₂ C10 ₄ ), 299(C ₁₄ H _2O

0 ₂ Br), 237(C ₁₃ H ₁₇ O ₄ ), 164(C ₁₀ H ₁₂ 0 ₂ ), 137(ΟθΗ ₉ Ο ₂ ), 105 (c ₄ h ₆ o).

₂ CS 269 382 Bl

IC spectrum (CC1 ₄ , 3%)? 2,825 (9 _g CH ₃ ), 1,613, 1,586, 1,515 CÍaromatics), 1,474 (JcH,+cT OCH-), 1,176, 1091, 1042 (heterocycle)cm ^-1 .

Biological effects were investigated in termites Prorhinotermes simplex and Coptotermes formosanum, mites Tetranychus urticae and cotton pests Dysdercus cingulatus. For example, 1*-(1-methoxy-2-bromopropyl)-4*-[4-(3-chloro-2-tetrahydrofuryl)oxybutoxy]benzene caused: in Prorhinotermes simplex (0.2 * wt. in acetone): a slowdown in development, resulting in the extinction of colonies (13th day 0/0, 15th day 0/0, 17th day 0/0, where the numerator of the fraction indicates the occurrence of white soldiers in %, and the denominator indicates the occurrence of intercastes in «), in Coptotermes formosanum (0.001 % wt. in acetone, Whatman filter paper No. 1): an 82% reduction in voraciousness, in the mites Tetranychus urticae an acaricidal effect was found in the sense of a reduction in oogenesis and hatchability already at a concentration of 10 ^-4 % vol.

Claims (2)

SUBJECT OF THE INVENTION 1. Vicinal bromo-alkoxy derivatives of aliphatic-aromatic ethers with a tetrahydrofuran ring in the molecule of the general formula I __-Cl <qJ-O-(CH ₂ ) ₄ -O-^ -CH(OR ¹ )-CH(Br)R ² (I), where r} denotes a straight-chain or branched alkyl group with a maximum of 3 carbon atoms, R denotes a methyl or ethyl group, as biologically active substances. 2. A method for preparing compounds according to point 1, of general formula I, characterized in that _an unsaturated ether of _general formula II is reacted with an alkanol of general formula III ^, wherein R has the above-mentioned meaning. R ¹ OH (III), where R ¹ has the above meaning, and N-bromosuccinimide at a temperature of 0 to 5 °C.