CS271357B1 - Mixed ester of succinic acid with 4-(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkanol and 3 beta,5-dihydroxy-5 alpha-cholestane-6-on as biologically active substance and method of its preparation - Google Patents

Abstract

The object of the solution are the new biologically effective substances of the general formula I, where the symbol R<1> stands for methyl group or ethyl group, the symbols R<2> and R<3> stand for alkyl group with a straight or branched chain with a maximum of 3 atoms of carbon. Their pesticide effects were tested e.g. on insects. The next part of the solution is the process of the preparation of substances of the general formula I that is based upon the reaction of monoester derivate of the general formula II, where the symbols R<1>, R<2>, R<3> have the above mentioned meaning at a presence of an equimolar quantity of dicyclohexylcarbodiimide and catalytic quantity of 4-dimethylaminopyridine in a medium of non-aqueous diethyl ether at a temperature of 15 to 25 degrees C with 3 β, 5 - dihydroxy-5 α -cholestane-on.<IMAGE>

Description

The invention relates to a mixed ester of succinic acid with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol and 3β, 5-dihydroxy-5Z-cholestan-6-one as a biologically active substance and a process for its preparation. The compounds of the invention exemplify another new type of pesticide in which a terpenoid and steroid component is contained in the molecule. The present invention provides a mixed succinic ester with 4- (3-alkoxy-2-alkyl-2-bromobutoxy) phenylalkanol and 3 (3,5-dihydroxy-5) -cholestan-6-one of formula I

OH 0

Wherein R is methyl or ethyl, R and R are alkyl having at most 3 carbon atoms.

A process for preparing a mixed succinic ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylaicanol and 3 [b, 5-dihydroxy-5 ° (-cholestan-6-one) of formula I is characterized in that and reacting the monoester derivative of the formula II

_CH3 / R ¹ / C / ^OR2 / -CHBr-CH2-0 - (^> - CH / R ³ / OCO / CH2 / ₂ COOH / II /,

Wherein R, R and R are as defined above in the presence of an equimolar amount of dicyclohexylcarbodiimide and a catalytic amount of 4-dimethylaminopyridine in anhydrous diethyl ether at 15-25 ° C with 3 (h, 5-dihydroxy-5oL-cholestan-6-one).

The invention is illustrated in more detail by way of example without being limited thereto.

Example

Reaction mixture of 70 mg (0.2 mmol) of monoesters of succinic acid with 4- (3-methoxy-3-methyl-2-bromobutoxy) phenylalkanol, 84 mg (0.2 mmol) of 3 / 3,5-dihydroxy-5 5- cholestan-6-one and 41 mg (0.2 mmol) of dicyclohexylcarbodiimide in 5 ml of anhydrous diethyl ether were stirred at 15-25 ° C for 2 hours in the presence of a catalytic amount of 4-dimethylaminopyridine, then allowed to stand overnight. After Ν, Ν-dicyclohexylurea was filtered off, the filtrate was washed successively with 5% aqueous hydrochloric acid, saturated sodium chloride solution. The ether layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was separated by column chromatography on silica gel with 8¾ wt. water (eluent petroleum ether containing up to 50¾ vol. diethyl ether). 37 mg (25%) of the reaction product was obtained. IR spectrum / CHCl-β 5¾;

3610.3440 (? 0Н). 1745, 1730, 1714 Л / СхО /, 1576,1526,1615 Льготаtika /, 1392,1303,1368 / ^ CI ^ / cm ^-1 .

¹³ C-NMR spectrum. 9.02

17.70 (CR-jCH), 20.45 (CH ₃ CH ₃ CH ₂ ), 11.10 (CH ₃₎ - | - | /, 12.97 / _CH3

/,

/, 21.13 and 21.92 / / СИ, / COCH, /, 2x21.65!

EN 271 357 Bl / / СН _3/2 С /, 23.6.3 / / 26.94 / / СН _3/2 С /.

24.45 / д ^ П _г / 27.11 (CH-jCHjOU),

3.20 /

28.18 (COCH ₂ ), 2S.94 (COCH ₂ CH ₂ ),

29.63 /

38.72 / /, 42.10 / / »32.9 ° /, 39.55

О ₂ /,

Сб /, 49.07 (СПВг), 54.59 / [—CH ₂ ], 55.34 /].

58.36 / ОСН ₃ /, 65.36 /

О-С0 /, 68.81 / 0СН ₂ /, 75.13 / 0н _3/2 СОСН ₃ / 76.27 /> П3.65 / / 126.91

Тн / л-СН /, 132.23 / £ 5) ^{-0 /} > 156.87 / ^^ 2-0 /, 168.76 / СОО /, О “ ^с

Ол

171.26 / С0 / * 12.-35.

The biological activity of the compounds according to the invention has been tested, for example, on the Sarcophaga bullata. Oviposition was nelíhla was almost 100% efficiency for example compound I, wherein R ¹ = CH 3, R ² = CH ^, 0 = C2H _third Applied dose of 10 mg in acetone.

Claims (2)

Mixed succinic ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol and 3?, 5-dihydroxy-5 (Z-cholestan-6-one of formula I) I _______ / Т /, в CS 271 357 Bl Wherein R is methyl or ethyl, R and R are straight or branched chain alkyl of up to 3 carbon atoms, as a biologically active agent. 12 3 2. A process for the preparation of a mixed succinic ester of the formula I wherein R, R and R are as defined above, characterized in that the monoester derivative of the formula II is reacted. CFT ₃ (R ¹ / C / OR ² ) -CHBr-CH ² -O-CH 2 R ³ OCO CH ₂ COOU / II), - < 123 wherein R, R and R are as defined above, in the presence of an equimolar amount of dicyclohexylcarbodiimide and a catalytic amount of 4-dimethylaminopyridine in anhydrous diethyl ether at 15 to 25 ° C with 5-dihydroxy-5-cholestan-6-one.