CS269386B1 - ¢ 3,7-Dialkoxy-3,7-dialkyl-2-bromoctyl) - (4-chlorophenyl ether) as a biologically active substance and a process for its preparation - Google Patents

Abstract

The subject of the solution is a new biologically active substance of the general formula I, where the symbol R^ denotes a methyl or ethyl group, the symbol R and RJ denotes a straight or branched alkyl group with a maximum of 3 carbon atoms. Its pesticidal effects were tested, for example, on insects and mites. Furthermore, a method of preparing a substance of the general formula I is presented, consisting in the reaction of an unsaturated ether of the general formula II» where the symbol R » R has the above-mentioned meaning» with an alkanol of the general formula III» where the symbol R^ has the above-mentioned meaning and N-bromosuccinimide at a temperature of 0 to 5 °C.

Description

o I

CS 269 386 Bl

CS 269 386 Bl

₃ CH (R ¹⁾ C (0R ^£) - (CH _{2) 3} -C (R - = 0 ^ 0 ^ -0- / 0 ^ -01 Ί 2 wherein R, is as defined above, with an alkanol of the formula III r ³ -oh wherein R ³ is as defined above, and N-bromosuccinimide at a temperature of 0 to 5 of the product of formula I.

*

The invention is further elucidated on the basis of an exemplary embodiment, without reference to this

The invention relates to (3,7-dialkoxy-3,7-dialkyl-2-bromoctyl) - (4-chlorophenyl ether) as a biologically active substance and to a process for its preparation.

The present invention provides (3,7-dialkoxy-3,7-dialkyl-2-bromoctyl) - (4-chlorophenyl ether) of formula I

CH ₃ (R ¹ ) C (OR ² ) - (CH 2) 3 - (R ³ ) C (OR ³ ) -CHBr-CH 2 -O-R ² -Cl (I), where R 1 is methyl or ethyl, R and R denote a straight-chain or branched alkyl group having a maximum of 3 carbon atoms.

A process for the preparation of (3,7-dialkoxy-3,7-dialkyl-2-bromoctyl) - (4-chlorophenyl ether) of the formula I is characterized in that an unsaturated ether of the formula II is reacted. .

(II), (III), ° C to give the example exclusively limiting.

Example

0.3 g (1.7 mmol) of N-bromosuccinimide was added to a solution of 0.31 g (1 mmol) of (7-ethoxy-3,7-dimethyl-2-octenyl) - (4-chlorophenyl ether) in 5 ml of anhydrous methanol at a temperature of 0 to 5 ° C with constant stirring and in the absence of atmospheric moisture. After stirring for 15 minutes, the reaction mixture was diluted with water and partitioned between diethyl ether and water. The separated dried ether layer was evaporated to dryness. Chromatography of the residue on a silica gel column with 8 wt. water (eluent petroleum ether containing up to 20% by volume of diethyl ether) gave 0.21 g (50%) of 7-ethoxy-3-methoxy-3,7-dimethyl-2-bromooctyl (4- (4-chlorophenyl ether)).

IR / CC1 _4, 5% /: 2833 / \) _with 0CH _3/1 599.1 507.1 495 / \> atomatika /, 1463 / CT _and CH _3/1 389.1 381.1 366 / A _with CH ₃ / cm ^-1 .

MS spectrum: 42o / 2 / 4M + C ^ H ^ OjBrCl /, 405/7/9 / C ₁₈ H ₂₇ O ₃ BrCl / 373/5/7 / C ₁₇ H ₂₃ O ₂ BrCl / 291/3 / 5 / C ₁₁ H ₁₃ O ₂ BrCl /, 247/9 / C ₁₁ H ₂₀ 0Br /, 215/7 / C ₁₀ H ₁₆ Br /, 87/0 ^^ 0 /.

¹³ C-NMR / 200MHz /: 16.15 / ¾ CH ₂ /, 19.39 / ^ C /, 25.56 and 25.71 // _CH3 / C ₂ /, 35.85 / C-CH ₂ CH ₂ CT ₂ /, 36.59 / C -CH ₂ and ₂ CH ₂ /, 40.24 / C-CH ₂ CH ₂ /, 50.00 / CHBr /, 56.32 / CH ₃ ^ ₂ O /, 56.67 / CH ₃ CO ^ ₃ /, 70.17 / ^ 0 /, 74.22 / / CH _3/2 C /. 78.02 / _CH3 C.0CH ₃ /, 116.13,126.00,129.30, 157.03 / aromatic /.

Biological effects were tested on insects and mites. .

Pro (7-ethoxy-3-methoxy-3,7-dimethyl-2-bromooctyl) - (4-chlorophenyl ether):

Pyrrhocoris apterus (topical application): 0.2 ug / of an insect individual caused developmental abnormalities in the form of intermediate forms /

Tenebrio molitor: topically 0.005 ug (insect individual caused morphological inhibition). '_5

Tetranychus urticae: at a concentration of 10% v / v (acetone solution), oogenesis and hatchability on bean leaves were affected.

CS 269 386 Bl

For tenuites Prorhinotermes simplex / 0.2% w / w. solution in acetone /: day 13 0 / 0.17.

i 19. day 0.0 - in the numerator there are% of white soldiers, in the denominator% of intermediate forms of intercast /.

An acaricidal effect (loop trials) has also been found in Varroa jacobsoni mites.

Claims (2)

OBJECT OF THE INVENTION (3,7-Dialkoxy-3,7-dialkyl-2-bromooctyl) - (4-chlorophenyl ether) of formula I CH 2 R 2 JCCOR 2 J-fCH 2 J 2 -H 2 CCOR 2 J-CHBr-CH 2 -O-2-Cl (I), β> 23 where R represents a methyl or ethyl group, R 1 and R 2 represent a straight or branched alkyl group. chain with a maximum of 3 carbon atoms, as a biologically active substance. 2. A process for the preparation of the compounds according to claim 1 of the formula I, characterized in that an unsaturated ether of the formula II is reacted. CH ₃ (R ¹ ) C (OR ² ) - (CH 2) 3 -C (R ¹ ) = CH-CH 2 -O- / Q 1 -C 1 Wherein R 1, R 2 are as defined above, with an alkanol of formula III R ³ -OH (II), (III), wherein R ³ is as defined above, and N-bromosuccinimide at 0 to 5 ° C.