CS270350B1 - 3- (2,2-dihalomethananyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] ester as a biologically active substance and its preparation process - Google Patents
3- (2,2-dihalomethananyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] ester as a biologically active substance and its preparation process Download PDFInfo
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Abstract
Předmětem řešeni je nová biologicky účinná látka obecného vzorce I, kde symbol R znáči alkylskupinu s rovným či rozvětveným řetězcem s maximálně 4 atomy uhlíku, symbol X značí halogen /chlor; brom/, symbol R# značí methyl- nebo athylskupinu. Oaji pesticidní účinky byly vyzkoušeny například na hmyzu a roztočích. Dalěi čáeti řeěeni je způeob přípravy látky obecného vzorce I, spočívající v reakci hydroxysloučanlny obecného vzorca XI kde symbol R, R1, X mají výše uvedený význam s organickou kyselinou obecného vzorce III, kde symbol X má výše uvedený význam za přítomnosti katalytického množství 4-dimethylaminopyridinu a ekvimolárního množství dicyklohexylkarbodiimidu při teplotě 10 až 20 °C nebo s chloridem či anhydridem organické kyseliny za přítomnosti ekvimolárního množství bezvodého pyridinu při 20 až 60 °C.The subject of the invention is a new biologically active substance of the general formula I, where the symbol R denotes a straight or branched chain alkyl group with a maximum of 4 carbon atoms, the symbol X denotes a halogen (chlorine; bromine), the symbol R# denotes a methyl or ethyl group. Its pesticidal effects have been tested, for example, on insects and mites. Another part of the invention is a method of preparing a substance of the general formula I, consisting in the reaction of a hydroxy compound of the general formula XI where the symbols R, R1, X have the above-mentioned meaning with an organic acid of the general formula III, where the symbol X has the above-mentioned meaning in the presence of a catalytic amount of 4-dimethylaminopyridine and an equimolar amount of dicyclohexylcarbodiimide at a temperature of 10 to 20 °C or with an organic acid chloride or anhydride in the presence of an equimolar amount of anhydrous pyridine at 20 to 60 °C.
Description
Vynález se týká lC4-/3-alkoxy-3-alkyl-2-halogsnbutoxy/fenyl7-alkylesteru 3-2,2-dihalogensnthenyl/-2,2-dimsthylcyklopropankarboxylová kyseliny jako biologicky účinné látky a způsobu jeho přípravy.The invention relates to 1C4-(3-alkoxy-3-alkyl-2-halogenobutoxy)phenyl-7-alkyl ester of 3-2,2-dihalogenophenenyl-2,2-dimethylcyclopropanecarboxylic acid as a biologically active substance and a method for its preparation.
Podstatou předmětného vynálezu je l-Í4-/3-alkoxy-3-alkyl-2-halogsnbutoxy/fenylJ alkylester 3-/2,2-dihalogonsthenyl/-2,2-dimethylcyklopropankarboxylové kyseliny obecného vzorce IThe subject of the present invention is 1-[4-(3-alkoxy-3-alkyl-2-halogenobutoxy)phenyl] alkyl ester of 3-(2,2-dihalogenostenyl)-2,2-dimethylcyclopropanecarboxylic acid of the general formula I
X2C»CH-CH-CH-C00CH/R/-^^-0CH2CH/X/-/R0/C/R1/CH3 (I), / 3/2 kde R značí alkylekupinu e rovným či rozvětveným řetězcem s maximálně '4 atomy uhlíku, X značí halogen (chlor, brom), R^ značí methyl- nebo ethylekupinu.X 2 C»CH-CH-CH-C00CH/R/-^^-0CH 2 CH/X/-/R0/C/R 1 /CH 3 (I), / 3/2 where R denotes an alkyl group with a straight or branched chain with a maximum of '4 carbon atoms, X denotes a halogen (chlorine, bromine), R^ denotes a methyl or ethyl group.
Způsob přípravy l-£4-/3-alkoxy-3-alkyl-2-halogenbutoxy/fenylj-alkyleeteru 3-/2,2-dihalogenethyl/-2,2-dimethylcyklopropankarboxylové kyseliny ee vyznačuje tím, že se nechá reagovet hydroxysloučenina obecného vzorce II ।A method for preparing 1-£4-(3-alkoxy-3-alkyl-2-halobutoxy)phenyl)-alkyl ether of 3-(2,2-dihaloethyl)-2,2-dimethylcyclopropanecarboxylic acid, characterized in that a hydroxy compound of general formula II is reacted.
H0CH/R/-(^^-0CH2-CH/X/-/R0/C/r1/CH3 ' (II), kde symboly R, R^a X mají výše uvedený význam, s organickou kyselinou obecného vzorce m ·H0CH/R/-(^^-OCH 2 -CH/X/-/R0/C/r1/CH 3 ' (II), where the symbols R, R^ and X have the above meaning, with an organic acid of the general formula m ·
X-OCH-CH-CH-COOH ' (III), 2 'c/ch3/2 .X-OCH-CH-CH-COOH ' (III), 2 'c/ch 3 / 2 .
kde symbol X má výše uvedený význam, za přítomnosti katalytického množství 4-dimethylaminopyridinu a ekvimolárniho množství dicyklohsxylkarbodiimidu při teplotě 1.0 až 20 °c nebo s chloridem či anhydridem organické kyseliny za přítomnosti ekvimolárniho množství bezvodého pyridinu při 20 až 60 °C. .where the symbol X has the above meaning, in the presence of a catalytic amount of 4-dimethylaminopyridine and an equimolar amount of dicyclohexylcarbodiimide at a temperature of 1.0 to 20 °C or with an organic acid chloride or anhydride in the presence of an equimolar amount of anhydrous pyridine at 20 to 60 °C.
V dalším je vynález blíže objasněn na příkladech provedení, sniž se na tyto výlučně omezuje.In the following, the invention is explained in more detail with reference to exemplary embodiments, but is not limited to these.
. Přiklad '. Example '
0,2 g (1 mmol) 3-(2,2-dichlorethenyl)-2;2-dlmethylcyklopropankarboxylové kyseliny, 0,36 g (1,1 mmol) l-Í4-(3-methoxy-3-methyl-2-brornbutoxy)fenylJ-l-propanolu, 0,2 g (1 mmol) dicyklohexylkarbodiimidu a 0,01 g (0,1 mmol) Ν,Ν-disthylamiriopyridinu bylo rozpuštěno a mícháno v 10 ml bezvodého diethyléteru při 15 až 20 °C po dobu 2 hodin. Po zředění reakční směai dlathyléterem a filtraci bylo éterická vrstva postupně promyta 6%-nim vodným roztokem kyeeliny chlorovodíkové a vodou, vysušena a odpařena. Odparek poskytl po dělení na sloupci silikagelu (slušní činidlo petroléter obsahující až 20 % obj. diethyléteru) 0,31 g (68 %) l-£4-(3-fnethoxy-3-methyl-2-brombutoxy)feny3jpropyleateru.0.2 g (1 mmol) of 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, 0.36 g (1.1 mmol) of 1-[4-(3-methoxy-3-methyl-2-bromobutoxy)phenyl]-1-propanol, 0.2 g (1 mmol) of dicyclohexylcarbodiimide and 0.01 g (0.1 mmol) of N,N-diethylaminopyridine were dissolved and stirred in 10 ml of anhydrous diethyl ether at 15 to 20 °C for 2 hours. After diluting the reaction mixture with diethyl ether and filtering, the ether layer was washed successively with 6% aqueous hydrochloric acid and water, dried and evaporated. The residue, after separation on a silica gel column (a suitable reagent is petroleum ether containing up to 20% by volume of diethyl ether), yielded 0.31 g (68%) of 1-[4-(3-methoxy-3-methyl-2-bromobutoxy)phenyl]propyl ether.
IC analýza (CC14,5 %) j 1727, 1719(ýc«0 ester.),* 1614( V C»C konj.), 1516, 158Θ, 1614 (Qarorn.), 1391, 1379, 1371 (^CH^cm’1.IC analysis (CC1 4 .5%) j 1727, 1719(ýc«0 ester.),* 1614( VC»C conj.), 1516, 158Θ, 1614 (Qarorn.), 1391, 1379, 1371 (^CH^cm' 1 .
NMR analýza (13C, CDClg,' 200 MHz) 1 9.72(01^0^), 16.96(CH3CH20), 15.08 a 28.40( (CH3)2 C4), 22.47, 24.62( (CH3)2C) , 27.22( |>_C(CH3)2), 29,20 (CHgCHg), 31.91, 32.15( CH - CH), ,NMR analysis ( 13 C, CDCl g ,' 200 MHz) 1 9.72(01^0^), 16.96(CH 3 CH 2 0), 15.08 and 28.40( (CH 3 ) 2 C4), 22.47, 24.62( (CH 3 ) 2 C) , 27.22( |>_C(CH 3 ) 2 ), 29.20 (CHgCHg), 31.91, 32.15(CH - CH), ,
57.46(CH3CH20), 69.01(CHBr); 69.88 (CH^Ó), 78,07(C(CH3)2), 77.18 (CHO), 121.23(001^, 124.98(CH > ČC12), 169.96(0,· O), 114.69,- 127.97; 133.19, 157.93 (arom.C).57.46(CH 3 CH 2 0), 69.01(CHBr); 69.88 (CH^O), 78.07(C(CH 3 ) 2 ), 77.18 (CHO), 121.23(001^, 124.98(CH > ČC1 2 ), 169.96(0,· O), 114.69,- 127.97; 133.19, 157.93 (arom.C).
Biologické účinky, byly zkbušeny na roztoči Tetranychus urticae, u něhož bylo zjištěno ovlivnění oogenezy a lihnivosti. .Biological effects were tested on the spider mite Tetranychus urticae, in which oogenesis and hatchability were found to be affected.
Pro 1-(4-(3-methoxy-3«methyl-2-brombutoxy)fsnylJ-1-propylester 3-(2,2-dichlorethenyl-2,2-dimethylcyklopropankarboxylové kyseliny (koncentrace lo“3 % obj. v acetonu, kontaktní aplikace na fazole)t 10 svilušek nakladlo běhám 96 hodin celkem 3 vajíčka, z nichž po 7 dnech byla 2 mrtvá. Při souběžném pokusu zs stejných experimentálních podmínek nakladlo 10 evilušek na listech fezole ošetřených pouze scetonem po 96 hodinách celkem 85 vajíček, které se po 7 dnech masově lihly. .For 1-(4-(3-methoxy-3-methyl-2-bromobutoxy)phenyl)-1-propyl ester of 3-(2,2-dichloroethenyl-2,2-dimethylcyclopropanecarboxylic acid (concentration 10 % vol. in acetone, contact application on beans), 10 spider mites laid a total of 3 eggs within 96 hours, of which 2 were dead after 7 days. In a parallel experiment with the same experimental conditions, 10 spider mites laid a total of 85 eggs on bean leaves treated with acetone alone after 96 hours, which hatched en masse after 7 days.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884200A CS270350B1 (en) | 1988-06-16 | 1988-06-16 | 3- (2,2-dihalomethananyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] ester as a biologically active substance and its preparation process |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884200A CS270350B1 (en) | 1988-06-16 | 1988-06-16 | 3- (2,2-dihalomethananyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] ester as a biologically active substance and its preparation process |
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| Publication Number | Publication Date |
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| CS420088A1 CS420088A1 (en) | 1989-11-14 |
| CS270350B1 true CS270350B1 (en) | 1990-06-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS884200A CS270350B1 (en) | 1988-06-16 | 1988-06-16 | 3- (2,2-dihalomethananyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] ester as a biologically active substance and its preparation process |
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| CS420088A1 (en) | 1989-11-14 |
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