CS269384B1 - Biologically efficient derivatives of 3,4-dihydro-2h-benzopyran and method of their preparation - Google Patents
Biologically efficient derivatives of 3,4-dihydro-2h-benzopyran and method of their preparation Download PDFInfo
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- CS269384B1 CS269384B1 CS884757A CS475788A CS269384B1 CS 269384 B1 CS269384 B1 CS 269384B1 CS 884757 A CS884757 A CS 884757A CS 475788 A CS475788 A CS 475788A CS 269384 B1 CS269384 B1 CS 269384B1
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- Prior art keywords
- dihydro
- benzopyran
- alkoxy
- carbon atoms
- formula
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- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 abstract description 3
- 241000238876 Acari Species 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- -1 3-Bromo-2,2-dimethyl-4-methoxy-6- (1-hydroxypropyl} -3,4-dihydro-2H-benzopyran Chemical compound 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241001007836 Prorhinotermes simplex Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229930191710 precocene Natural products 0.000 description 1
- CPTJXGLQLVPIGP-UHFFFAOYSA-N precocene I Chemical compound C1=CC(C)(C)OC2=CC(OC)=CC=C21 CPTJXGLQLVPIGP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
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 effective derivatives of 3,4-dihydro-2H-benzopyran of formula (I) wherein R @ 1 is hydrogen and R is independently one of these substituents: 1-hydroxyalkyl or alkoxy or alkoxyalkoxy with a maximum of 3 carbon atoms, and R4 is bromo or alkoxy with a maximum of 3 carbon atoms, namely in such a way that R4 denotes bromine, R® represents an alkoxy group and vice versa. Their a pesticidal effect has been tried, for example insects and mites. Another part the solution is a way of preparing the general substances of formula (I), consisting of an unsaturated reaction compounds of formula II, 1 2 wherein R, R are as defined above meaning with alkanol with up to 3 atoms carbon in alkyl and N-bromosuccinimide at 0-5 ° 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.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically efficient derivatives of 3,4-dihydro-2h-benzopyran and method of their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically efficient derivatives of 3,4-dihydro-2h-benzopyran and method of their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS475788A1 CS475788A1 (en) | 1989-09-12 |
| CS269384B1 true CS269384B1 (en) | 1990-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS884757A CS269384B1 (en) | 1988-07-01 | 1988-07-01 | Biologically efficient derivatives of 3,4-dihydro-2h-benzopyran and method of their preparation |
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| Country | Link |
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| CS (1) | CS269384B1 (en) |
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1988
- 1988-07-01 CS CS884757A patent/CS269384B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS475788A1 (en) | 1989-09-12 |
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