CS250585B1 - Mixed ester of succinic acid with 11,alkoxy-10-hydroxy-3,7,11-trimethyl-2,4-dodecadiene acid's alkylester and method of its preparation - Google Patents

Description

The present invention relates to a mixed ester of succinic acid with 1- (2,2-dimethyl-2H-chromen-6-yl) -1-alkanol and an alkyl ester of iralkoxy-10-hydroxy-3,7,11-trimethyl-2, 4-dodecadienes as biologically active substances and processes for their preparation.

Substances which cause developmental deviation in their final effect on insects include the compounds of the invention. Their specificity is that they contain in the molecule a portion responsible for developmental deviation caused by the effect typical of juvenile hormone analogs and a portion responsible for developmental deviation caused by the effect typical for precocene-type analogs.

The present invention provides a mixed succinic ester of 1- (2,2-dimethyl-2H-chromen-6-yl) -1-alkanol and an alkyl ester of 11-alkoxy-10-hydroxy-3,7,11-trimethyl-2,4 - dodecadienes of the general formula I wherein the symbol

R ¹ denotes a straight or branched chain alkyl group having a maximum of 3 carbon atoms R ² denotes an OR ³

CH3 — C — CH3 CH3 CH3 —CH— (CH2) 2 — CH — CH2 — CH = CH — C = = CH — COOR ⁴ where symbols

R ³ and R ⁴ denote a straight or branched chain alkyl group having a maximum of 3 carbon atoms.

The process for preparing the mixed ester of formula I is characterized by reacting the monoester derivative of formula

O-CO-CH 2 CH 2 CO-OH (li)

250583

found:

% C, 70.74;% H, 8.76.

IC analysis (OCl4):

1741, 1729 (in C = O ester), 1651, 1642 (in C = C),

614, 1 494 (arom.),

393, 1375 (5 _with CH 3 cm -1 ⁾ .

(II) where symbol

R ¹ is as defined above with an alcohol of the formula III

OR ³

CH 3 —CH 2, CH 3 CH 3 CH 3

HO — CH— (CH2) 2 — CH — CH2 — CH = CH — C = CH - COOR ⁴ (III) where symbols

R ³ and R ⁴ 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 a temperature of 15-25 ° C.

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

Example 1

Reaction mixture (64 mg (0.2 mmol) of succinic acid monoester with 1- (2,2-dimethyl-2H-chromen-6-yl) -1-propanol, 63 mg (0.2 mmol) of 11-methoxy isopropyl ester) -10-hydroxy-3,7,11-trimethyl-2,4-dodecadiene and 41 mg (0.2 mmol) of dicyclohexylcarbodiimide in 5 mL of anhydrous diethyl ether were stirred at 15-25 ° C in the presence of a catalytic amount of 4-dimethylaminopyridine. After filtering the N, N'-dicyclohexylurea, the filtrate was washed successively with 5% aqueous hydrochloric acid solution, saturated sodium chloride solution, and 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 8 wt% water (eluent petroleum ether containing up to 20 vol% diethyl ether) to give 56 mg (45%) of the reaction product.

for C37H54O8 (m. v. 642):

calculated:

% C, 70.89;% H, 8.68;

Biological effects were observed: in termites:

I. influencing the development of soldiers and white soldiers, the overall slowdown in development.

Prorhinotermes simplex (application to Whatman # 1 chromatography paper, in acetone) was used as the test organism. To monitor the antijuvenile effect, a high degree of developmental determination on the military caste was first induced using the juvenilizing agent methoprene. Influence, ie reduction of the number of soldiers or total prevention of their formation, eventually the emergence of transient individuals between soldiers and larvae called intercaasts is then reported as a fraction, where the numerator indicates the percentage of fully developed white soldiers, the denominator .

Mixed succinic ester with 1- (2,2-dimethyl-2H-chromen-6-yl) -1-propanol and alkyl ester of 11-alkoxy-10-hydroxy-3,7,11-trimethyl-2,4-dodecadienoic acid (0,2% by weight in acetone):

0/0 after 11 days. 0/0 after 13 days,

0/0 after 15 days, 0/0 after 17 days,

0/0 after 19 days, 20/20 after 21 days.

Effect of methoprene (0.1%):

10/0 after 11 days, 30/0 after 13 days,

40/0 after 15 days, 60/0 after 17 days,

80/0 after 19 days, 80/0 after 21 days.

II. antifeedant effect

Coptotermes formosanum (application to Whatman # 2 chromatographic paper, in acetone) was used as the test organism. For 0.1 wt. solution mixed ester of succinic acid of the invention (R ¹ = ethyl, R ³ = methyl, R ⁴ - = isopropyl) in acetone occurs in greed termite reduction of 79% compared to control groups of termites.

Biological effects have also been studied in Pyrrhocoris apterus. Activity was assessed by inhibition of metamorphosis, and is expressed in quantity in micrograms per insect individual, which triggers when topically applied form an intermediate forms: Idso sample mixed ester of succinic acid of the invention (R ¹ - ethyl, R ³ - methyl, R ⁴ - isopropyl j - 1.

Claims (2)

Mixed succinic ester with 1- (2,2-dimethyl-2H-chromen-6-yl) -1-alkanol and alkyl ester of 11-alkoxy-10-hydroxy-3,7,11-trimethyl-2,4-dodecadienoic acid of formula I of petroleum jelly succinic formula I wherein reacting a monoester derivative of the formula II CH ₃ tw ₃ R-CH-Io CH, CH 3. _{-O-CO-CH2-CH2} what QR ' Q ~ C CQ-Q-R (!) (I) where symbol R ¹ denotes a straight or branched chain alkyl group having a maximum of 3 carbon atoms R ² denotes an OR ³ CH3 — C — CH3 CH3 CH3 —CH- (CH2) 2 — CH — CH2 — CH = CH — C == = CH — COOR ⁴ where symbols R ³ , R ⁴ denote a straight or branched chain alkyl group having a maximum of 3 carbon atoms. 2. A method for preparing a mixed ester everywhere R ¹ is as defined above with an alcohol of the formula III OR ³ CH 3 -C 3 CH 3 CH 3 CH 3 HO — OH - (CH2) 2 — CH — CH2 — CH = CH — C = -CH-COOR ⁴ (ΙΠ) where symbols R ³ and R ⁴ 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 a temperature of 15-25 ° C.