CS264865B1 - Alkoxy derivatives of aliphatic-aromatic ethers with halogen in the alkoxyalkyl group and the process for their preparation - Google Patents

Abstract

The essence of the solution is alkoxy derivatives of aliphatic-aromatic ethers with halogen in the alkoxyalkyl group of the general formula I R1OCH2CHBrC(CH3)2-O o. (1) where the symbol R1 denotes an alkyl group with a maximum of 5 carbon atoms, R2 denotes an alkyl group with a maximum of 4 carbon atoms, chlorine or an alkoxy group with a maximum of 4 carbon atoms. The preparation method consists in the reaction of an unsaturated ether of the general formula II where the symbol R2 has the above meaning, with an alkanol of the general formula III R1-OH (III) where the symbol R1 has the above meaning and N-bromosuccinimide at 0 to 5 °C. The substances show biological activity.

Description

The invention relates to alkoxy derivatives of aliphatic-aromatic ethers with halogen in alkoxyalkyl as a biologically active substance and to a process for their preparation.

The present invention provides alkoxy derivatives of aliphatic-aromatic ethers with halogen in the alkoxyalkyl group of the general formula (I) - (O ^{) -} (CHCl 2 CH 3) i -O-R ² (I) wherein R ¹ represents an alkyl group having a maximum of 5 carbon atoms;

R is alkyl of up to 4 carbon atoms, chlorine or alkoxy of up to 4 carbon atoms.

The process for preparing a group is characterized by alkoxy derivatives of aliphatic-aromatic ethers with halogen in the alkoxyalkyl group by leaving an unsaturated ether of the general formula IX - ch ₂ = ch - c (ch ₃ ) _{2 -} o (II) wherein R is as defined above with alkanol of formula III

R ¹ -OH (III) wherein R ¹ is as defined above and with N-bromosuccinimide at 0-5 ° C to give the product of formula (I).

In the following, the invention is explained in more detail by way of example without being limited thereto.

Example (1,1-Dimethyl-2-propenyl) - (4-chlorophenyl) ether (0.01 mol) was treated with 0.017 molar amount of N-bromosuccinimide under anhydrous methanol under a dry nitrogen atmosphere. Stir at 0-5 ° C for 15 minutes and then dilute with water and extract with diethyl ether. After drying the ether layer over anhydrous magnesium sulfate and evaporating the solvent, the residue was chromatographed on silica gel with 8 wt. % water (eluent petroleum ether containing up to 10 vol% diethyl ether). Thus, for example, 1.0 g (70%) of (2-bromo-1,1-dimethyl-3-methoxypropyl) - (4-chlorophenyl) ether was obtained.

IC analysis (CCl ₄ , 5%): 2,834 (YCH ₃ in OCH ₃ ), 1,598, 1,584, 1,496 ()) arom.,

466 (ct, CH3), (CH3): 1369, 1384, 1393 cm ^-1 .

SCI S · 2 S 5

MS analysis: 306/8/10 ^<M), (C ^ H ^ BrClop, 128/30 (CGH-LO), 73 (C ₄ H O _g).

In the same way they were prepared:

(2-bromo-1,1-dimethyl-3-methoxypropyl) - (4-ethylphenyl) ether and (2-bromo-1,1-dimethyl-3-methoxypropyl) - (4-methoxyphenyl) ether.

(2-Bromo-1,1-dimethyl-3-methoxypropyl) - (4-ethylphenyl) ether:

IC analysis (CCl ₄ , 5%): 2,834 (1) CH in OCH 3), 1,613, 1,585, 1,516 (V aromatics),

466 _(CT CH _2), 1393, 1384, 1368 (ΰζ (CH _{3) 2)} cm ^_1.

MS analysis: 300/2 (M ⁺ , ^c 14 ^H 21 ^BrO 2 ⁾ , 135 (C 8 H 16 O).

(2-Bromo-1,1-dimethyl-3-methoxypropyl) - (4-methoxyphenyl) ether:

IC analysis (CCl., 5%): 2,985 (CH in OCH,), 2,835 ()H in OCH,), 1,612, rk 35 J n

593, 1514 ([alpha] aromatics), 1393, 1374, 1368 ([mu] _g (CH2) ₂ ) cm.

MS analysis: 302/4 (M ^+, C ₁₃ H ₃ BrO _g), 124 (C ₇ H ₂ O _g).

Biological effects were monitored:

in spider mite Tetranychus urticae. For (2-bromo-1,1-dimethyl-3-methoxypropyl) - (4-ethylphenyl) ether: -2 topical application of 10 vol% (5 µl) to bean leaves: 12 spider mites laid 76 eggs in 96 hours, which was all dead within 7 days and none of them hatched.

_2

For (2-bromo-1,1-dimethyl-3-methoxypropyl) - (4-methoxyphenyl) ether: 10 vol%: 12 spider mites laid 6 eggs in 96 hours, all dead after 7 days (none hatched) .

Claims (2)

SUBJECT OF THE INVENTION 1. Alkoxy derivatives of aliphatic-aromatic ethers with halogen in the alkoxyalkyl group of the general formula I R ¹ OCH ₂ CHBrC _{(CH3) 2} --O - R2 (I) wherein the symbol R represents an alkyl group having up to 5 carbon atoms, R is alkyl of up to 4 carbon atoms, chlorine or alkoxy of up to 4 carbon atoms. 2. A process for the preparation of alkoxy derivatives of aliphatic-aromatic ethers having halogen in the alkoxyalkyl group of general formula (1) according to claim 1, characterized in that the unsaturated ether of general formula (II) is left ch ₂ = ch-c (ch ₃ ) ₂ -o P, (II) wherein R is as defined above with an alkanol of formula III R @ ¹ --OH. (III) wherein R ¹ is as defined above and with N-bromosuccinimide at 0 to 5 ° C to give the product of formula (I).