CS269384B1 - Biologically active derivatives of 3,4-dihydro-2H-benzopyran and a process for their preparation - Google Patents
Biologically active derivatives of 3,4-dihydro-2H-benzopyran and a process for their preparation Download PDFInfo
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Abstract
předmětem řešení jsou nové biologicky účinné deriváty 3,4-dihydro-2H-benzopyranu obecného vzorce I, kde symbol R^ a R značí nezávisle na sobě jeden z těchto substituentú: 1-hydroxyalkylskupinu či alkoxyskupinu nebo alkoxyalkoxyskupinu s maximálně 3 atomy uhlíku, symboly a R4 značí brom nebo alkoxyskupinu s maximálně 3 atomy uhlíku, a to takovým způsobem, že značí-li R4 brom, R® značí alkoxyskupinu a naopak. Jejich pesticidní účinek byl vyzkoušen například na hmyzu a roztočích. Další částí řešení je způsob přípravy látek obecného vzorce I, spočívající v reakci nenasycené sloučeniny obecného vzorce II, 1 2 kde symboly R , R mají výše uvedený význam s alkanolem s maximálně 3 atomy uhlíku v alkylskupině a N-bromsukcinimidera při teplotě 0 až 5 °C.The subject of the solution are new biologically active derivatives of 3,4-dihydro-2H-benzopyran of the general formula I, where the symbols R^ and R independently denote one of the following substituents: a 1-hydroxyalkyl group or an alkoxy group or an alkoxyalkoxy group with a maximum of 3 carbon atoms, the symbols and R4 denote bromine or an alkoxy group with a maximum of 3 carbon atoms, in such a way that if R4 denotes bromine, R® denotes an alkoxy group and vice versa. Their pesticidal effect was tested, for example, on insects and mites. Another part of the solution is a method of preparing substances of the general formula I, consisting in the reaction of an unsaturated compound of the general formula II, 1 2 where the symbols R , R have the above-mentioned meaning with an alkanol with a maximum of 3 carbon atoms in the alkyl group and N-bromosuccinimide at a temperature of 0 to 5 °C.
Description
Vynález se týká biologicky účinných derivátů 3,4-dihydro-2H-benzopyranu a způsobu jejich přípravy.The invention relates to biologically active 3,4-dihydro-2H-benzopyran derivatives and to a process for their preparation.
Látky, Jež Jsou předmětem vynálezu představují ekologicky vhodnější variantu prekocenových, biologicky účinných sloučenin.The substances which are the subject of the invention represent a more environmentally friendly variant of precocene, biologically active compounds.
Podstatou vynálezu jsou biologicky účinné deriváty 3,4-dihydro-2H-benzopyranu obecného vzorce IThe invention relates to biologically active 3,4-dihydro-2H-benzopyran derivatives of the formula I.
(I), ?(I),?
kde R a R značí nezávisle na sobě jeden z těchto substituentů: 1-hydroxyalkylsku3 4 plnu či alkoxyskupinu nebo alkoxyalkoxyskupinu s maximálně 3 atomy uhlíku, R a R značí brom nebo alkoxyskupinu s maximálně 3 atomy uhlíku, a to takovým způsobem, že značí-li R^ brom, R·^ značí alkoxyskupinu a naopak.wherein R 1 and R 2 independently represent one of the following substituents: 1-hydroxyalkyl3 4 full or alkoxy or alkoxyalkoxy having at most 3 carbon atoms, R 1 and R 2 represent bromo or alkoxy having at most 3 carbon atoms, in such a way that when R 1 is bromo, R 2 is alkoxy and vice versa.
Způsob přípravy biologicky účinných derivátů 3,4-dihydro-2H-benzopyranu obecného vzorce X se vyznačuje tím,že se nechá reagovat nenasycená sloučenina obecného vzorce IIA process for the preparation of biologically active 3,4-dihydro-2H-benzopyran derivatives of the general formula X is characterized in that an unsaturated compound of the general formula II is reacted.
(II),(II),
2 kde R , R mají výše uvedený význam, s alkanolem s maximálně 3 atomy uhlíku v alkylskupině a N-bromsukcinimidem při teplotě 0 až 5 °C, za vzniku látky obecného vzorce I.2 wherein R 1, R 2 are as defined above, with an alkanol having at most 3 carbon atoms in the alkyl group and N-bromosuccinimide at a temperature of 0 to 5 ° C, to give a compound of formula I.
Vynález je blíže objasněn na příkladu provedení, aniž by se na tento příklad výlučně omezoval.The invention is further elucidated by means of an exemplary embodiment, without being limited exclusively to this example.
Příklad 1Example 1
K roztoku 0,19 g (1 mmol) 2,2-dimethyl-7-methoxy-2H-ben.zopyranu v 5 ml bezvodého methanolu bylo při teplotě 0 až 5 °C přidáno za míchání a za nepřístupu vzdušné vlhkosti 0,2 g (1,7 mmol) N-bromsukcinimidu. Reakční směs byla pak ještě míchána 15 minut. Po zředění vodou a extrakci diethyléterem byla oddělená a vysušená éterická vrstva odpařena. Odparek poskytl po dělení na sloupci silikagelu s 8 % hmot, vody (eluční činidlo: petroléter obsahující až 50 % obj. diethyléteru) 0,2 g (67 %) 3-brom-2,2dimethyl-4,7-dimethoxy-3,4-dihydro-2H-benzopyranu.To a solution of 0.19 g (1 mmol) of 2,2-dimethyl-7-methoxy-2H-benzopyran in 5 mL of anhydrous methanol at 0-5 ° C was added 0.2 g with stirring and in the absence of atmospheric humidity. (1.7 mmol) of N-bromosuccinimide. The reaction mixture was then stirred for another 15 minutes. After dilution with water and extraction with diethyl ether, the separated and dried ether layer was evaporated. The residue was separated on a silica gel column with 8% by weight of water (eluent: petroleum ether containing up to 50% by volume of diethyl ether) to give 0.2 g (67%) of 3-bromo-2,2-dimethyl-4,7-dimethoxy-3. 4-dihydro-2H-benzopyran.
IC spektrum (CC1., 5 «) : 2830(J CH, v OCH,), 1613,1581,1489(aromatika), 1444(ď CH,IC spectrum (CCl., 5 «): 2830 (J CH, in OCH 3), 1613, 1581, 1489 (aromatics), 1444 (J CH,
J J η S J v OCH,), 1387,1372( ď „CH,)cm . X),/ 1JC-NMR spektrum: 22.97 a 27.31 ((CH3)2C), 55.24 ( <^OHBr), 55.99 (OCH3),JJ η SJ v OCH,), 1387,1372 (ď „CH,) cm. X), / 1J C-NMR spectrum: 22.97 and 27.31 ((CH 3 ) 2 C), 55.24 (<1 OHBr), 55.99 (OCH 3 ),
56.16 (CH3O-@), 78.19 (C(CH3)2), 78.69 (CHOCH,), 101.3656.16 (CH 3 O- @), 78.19 (C (CH 3 ) 2 ), 78.69 (CHOCH 3), 101.36
108.52 (ChSO’ 112'76 ((Op» 129.38 ( l^t), 153.84 ( 160.84 (CH3O-£gp.108.52 ( ChSO ' 112 ' 76 ( (Op »129.38 (l ^ t)), 153.84 (160.84 (CH 3 O- £ gp.
Příklad 2Example 2
Stejným způsobem byl připraven 3-brom-2,2-dimethyl-4-methoxy-6-(l-hydroxypropyl}3,4-dihydro-2H-benzopyran. MS spektrum: 328/330 M+, O^H^BrOj).3-Bromo-2,2-dimethyl-4-methoxy-6- (1-hydroxypropyl} -3,4-dihydro-2H-benzopyran was prepared in the same manner. MS spectrum: 328/330 M + , O 2 H 2 BrO 3). .
Biologická účinnost látek podle vynálezu byla zkoušena například na termitech Prorhinotermes simplex (insekticidní účinek u 0,2 % váh. v acetonu, vznik interkast u 0,2 % váh. za přídavku 0,1 % váh. juvenilizačního metoprénu v acetonu: 14.den 10/10 v čitateli % bílých vojáků, ve jmenovateli % interkast.The biological activity of the substances according to the invention was tested, for example, on the termites Prorhinotermes simplex (insecticidal effect at 0.2% by weight in acetone, intercalation at 0.2% by weight with the addition of 0.1% by weight of juvenile metoprene in acetone: day 14 10/10 in the numerator% of white soldiers, in the denominator% intercast.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically active derivatives of 3,4-dihydro-2H-benzopyran and a process for their preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically active derivatives of 3,4-dihydro-2H-benzopyran and a process for their preparation |
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| Publication Number | Publication Date |
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| CS475788A1 CS475788A1 (en) | 1989-09-12 |
| CS269384B1 true CS269384B1 (en) | 1990-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically active derivatives of 3,4-dihydro-2H-benzopyran and a process for their preparation |
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1988
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| CS475788A1 (en) | 1989-09-12 |
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