CS269383B1 - 2-/2-hydroxyethylthio/ethylester of 1-/2,2-dimethyl-6-/2h-benzopyranyl//1-alkyloxycarbonylpropanoic acid as biologically efficient substance and method of its preparation - Google Patents

2-/2-hydroxyethylthio/ethylester of 1-/2,2-dimethyl-6-/2h-benzopyranyl//1-alkyloxycarbonylpropanoic acid as biologically efficient substance and method of its preparation Download PDF

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CS269383B1
CS269383B1 CS884756A CS475688A CS269383B1 CS 269383 B1 CS269383 B1 CS 269383B1 CS 884756 A CS884756 A CS 884756A CS 475688 A CS475688 A CS 475688A CS 269383 B1 CS269383 B1 CS 269383B1
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hydroxyethylthio
acid
benzopyranyl
dimethyl
alkyloxycarbonylpropanoic
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CS884756A
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Czech (cs)
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CS475688A1 (en
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Jitka Ing Csc Kahovcova
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Kahovcova Jitka
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Publication of CS269383B1 publication Critical patent/CS269383B1/en

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Abstract

Předmětem řešení jsou nové biologicky účinné látky obecného vzorce I, kde symbol R značí alkylskupinu s maximálně 3 atomy uhlíku. Jejich pesticidní účinky byly vyzkoušeny například na termitech. Další částí řeáení je způsob přípravy látky obecného vzorce I, spočívající v reakci organické kyseliny obecného vzorce II, kde symbol R má výše uvedený význam, s 2-(2-hydroxyethylthio)- -ethanolem za přítomnosti ekvimolárního množství dicyklohexylkarbodiimidu a katalytického množství N,N-dimethylaminopyridinu při teplotě 10 až 20 °CThe subject of the solution is new biologically the active compounds of the formula I wherein R represents an alkyl group of at most 3 carbon atoms. Their pesticidal effects for example, on termites. Another part of the solution is the method of preparation of formula (I) in the reaction of an organic acid of formula II wherein R is as defined above as defined above, with 2- (2-hydroxyethylthio) - -ethanol in the presence of equimolar amount of dicyclohexylcarbodiimide and catalytic the amount of N, N-dimethylaminopyridine at 10-20 ° C

Description

Vynález se týká 2-(2-hydroxyéthylthio)ethylesteru kyseliny 1-^2,2-dimethyl-6-(2H-benzopyranyl)j-l-alkyloxykarbonylpropanové jako biologicky účinné látky a způsobu její přípravy.The present invention relates to 1- (2,2-dimethyl-6- (2H-benzopyranyl) -1-1-alkyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester as a biologically active substance and to a process for its preparation.

Podstatou vynálezu je 2-(2-hydroxyethylthio)ethylester kyseliny l-f2,2-dimethyl-6-(2H-benzopyranyl)J-1-alkyloxykarbonylpropanové obecného vzorce I ch3 The present invention provides 1- (2,2-dimethyl-6- (2H-benzopyranyl) -1-1-alkyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester of formula I ch 3

CH3 CH 3

R-C I 0C0(CH2)2COOCH2CH2SCH2CH2OH (I).RC I 0C0 (CH 2 ) 2 COOCH 2 CH 2 SCH 2 CH 2 OH (I).

kde R značí alkylskupinu s maximálně 3 atomy uhlíku.wherein R represents an alkyl group having at most 3 carbon atoms.

Biologické účinky (například pesticidní) byly zkoušeny například na termitech, škůdcích na dřevě, kde se dosud používal ekologicky nevhodný pentachlorfenol.Biological effects (for example pesticidal) have been tested, for example, on termites, pests on wood, where ecologically unsuitable pentachlorophenol has hitherto been used.

Způsob přípravy 2-(2-hydroxyethylthio)ethylesteru kyseliny l-f2,2-dimethyl-6-(2H-benzopyranyl)J-l-alkyloxykarbonylpropanové obecného vzorce I se vyznačuje tím, že se nechá reagovat organická kyseliny obecného vzorce IIProcess for the preparation of 1- (2,2-dimethyl-6- (2H-benzopyranyl) -1-1-alkyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester of the formula I is characterized in that the organic acids of the formula II are reacted

OCO(CH2)2COOH kde R má výše uvedený význam, s 2-(2-hydroxyethylthio)ethanolem za přítomnosti ekvimolárního množství dicyklohexylkarbodiimidU a katalytického množství N,N-dimethylaminopyridinu při teplotě 10 až 20 °C, za vzniku produktu obecného vzorce I.OCO (CH 2 ) 2 COOH wherein R is as defined above, with 2- (2-hydroxyethylthio) ethanol in the presence of an equimolar amount of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine at 10 to 20 ° C to give the product of formula I .

Vynález je blíže objasněn na příkladu provedení, aniž se na tento příklad výlučně omezuje.The invention is further elucidated by means of an exemplary embodiment, without being exclusively limited to this example.

PříkladExample

0,13 g (1,1 mmol) 2-(2-Hydroxyethylthio)ethanolu, 0,33 g (1 mmol) 3-{l-f2,2-dimethyl-6-/2H-benzopyranyl/J-l-propyloxykarbonyl propanové kyseliny, 0,2 g (.1 mmol) dicyklchexylkarbodiimidu a 0,01 g (0,1 mmol) Ν,Ν-dimethylaminopyridinu bylo při teplotě 15 až 20 °C v 10 ml bezvodého diethyléteru mícháno po dobu 2 hodin. Po zředění diethyléterem, filtraci a promytí 5%ním roztokem kyseliny chlorovodíkové a vodou byla oddělená éterická vrstva vysušena nad bezvodým síranem sodným, odpařena a dělena na sloupci silikagelu s 8 % hmot, vody /eluční činidlo petroléter obsahující až 20 % cbj. diethyléteru/. Spojením chromatograficky jednotných frakcí bylo po odpaření rozpouštědel získáno 0,19 g /45 %/ 2-/2-hydroxyethylthio/-ethylesteru kyseliny 1-^2,2-dimethyl-6-/2H-benzopyranyl/J-l-propyloxykarbonylpropanové.0.13 g (1.1 mmol) of 2- (2-hydroxyethylthio) ethanol, 0.33 g (1 mmol) of 3- {1- (2,2-dimethyl-6- (2H-benzopyranyl) -1H-propyloxycarbonyl propanoic acid] , 0.2 g (.1 mmol) of dicyclchexylcarbodiimide and 0.01 g (0.1 mmol) of. After dilution with diethyl ether, filtration and washing with 5% hydrochloric acid and water, the separated ether layer was dried over anhydrous sodium sulfate, evaporated and separated on a silica gel column with 8% w / w water / eluent petroleum ether containing up to 20% cbj. diethyl ether. Combining the chromatographically uniform fractions gave, after evaporation of the solvents, 0.19 g (45%) of 1- (2,2-dimethyl-6- (2H-benzopyranyl) -1H-1-propyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester.

MS spektrum: 422/M+,C22H3oO6S/, 407/C21H2706S/, 3O3/C1SH23O4/, 201/014Η1?0/, 185 ’ ’ /c^jHi3°/» 171/c12huo/, io5/c4h9os/ 1H-NMR spektrum: 0.80/t,CH3CH2,J=7.0/, 1.35//CH3/2C,s/, 2.1 - 2.65/M, CH2C00+CH2CH0C0/, 2.65/t,J=7.O,CH2S/, 3.68/t,J=6.O,CH2OH/, 6.56 - 7.17/m,arom.H/.MS spectrum: 422 / M +, C 22 H 3 O S O 6 /, 407 / C 21 H 27 0 6 S /, 3O3 / C 1S H 23 O 4 /, 1 Η 201/0 14? 0/185 '/ c ^ jHi3 ° / »171 / C for 12 h in a /, io5 / C 4 H 9 OS / 1 H-NMR: 0.80 / t, CH 3 CH 2, J = 7.0 /, 1.35 // CH 3/2 C, /, 2.1 to 2.65 / m, CH 2 CH 2 C00 + CH0C0 /, 2.65 / t, J = 7.O, CH 2 s /, 3.68 / t, J = 6th O, CH 2 OH /, 6.56 - 7.17 (m, arom.H).

Biologické účinky byly zkoušeny například u termitu Prorhinotermes simplex /0,2 % váh. v acetonu/: 13. den 0/0, 15. den 0/0, 17. den 0/0, 19. den 0/0, kde v čitateli je uvedeno % bílých vojáků a ve jmenovateli % interkast. Zpomalení přirozeného vývoje vede ve svých důsledcích k zániku celých kolonií.Biological effects have been tested, for example, with the termite Prorhinotermes simplex / 0.2% by weight. in acetone /: 13th day 0/0, 15th day 0/0, 17th day 0/0, 19th day 0/0, where in the numerator the% of white soldiers and in the denominator% intercast. The slowing down of natural development leads in its consequences to the extinction of entire colonies.

Claims (2)

P S E D M Ě T VYNÁLEZUBACKGROUND OF THE INVENTION 1. 2-(2-Hydroxyethylthio)ethylester kyseliny 1-^2,2-dimethyl-6-(2H-benzopyranyl)J-l-alkyioxykarbonylpropanové obecného vzorce I1- (2,2-Dimethyl-6- (2H-benzopyranyl) -1,1-alkyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester of general formula I (I)»(AND)" OCO(CH2)2COOCH2CH2SCH2CH2OH kde R značí alkylskupinu s maximálně 3 atomy uhlíku, jako biologicky účinná látka . .OCO (CH 2 ) 2 COOCH 2 CH 2 SCH 2 CH 2 OH where R represents an alkyl group with a maximum of 3 carbon atoms, as a biologically active substance. . 2. Způsob přípravy 2-(2-hydroxyethylthio)ethylesteru kyseliny l-f2,2-dimethyl-6-(2H-benzopyranyl)]-l-alkyloxykarbonylpropaňové obecného vzorce I, vyznačující se tím, že se nechá reagovat organická kyselina obecného vzorce IIProcess for the preparation of 1- (2,2-dimethyl-6- (2H-benzopyranyl)] - 1-alkyloxycarbonylpropanoic acid 2- (2-hydroxyethylthio) ethyl ester of the general formula I, characterized in that an organic acid of the general formula II is reacted (II), oco(ch2)2cooh kde R má výše uvedený význam, s 2-(2-hydroxyethylthio)ethanolem za přítomnosti ekvimolárního množství dicyklohexylkarbodiimidu a katalytického množství N,Ndimethylaminopyridinu při teplotě 10 až 20 °C.(II), oco (ch 2 ) 2 cooh wherein R is as defined above, with 2- (2-hydroxyethylthio) ethanol in the presence of an equimolar amount of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine at 10 to 20 ° C.
CS884756A 1988-07-01 1988-07-01 2-/2-hydroxyethylthio/ethylester of 1-/2,2-dimethyl-6-/2h-benzopyranyl//1-alkyloxycarbonylpropanoic acid as biologically efficient substance and method of its preparation CS269383B1 (en)

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