CS269381B1 - S-succinic acid semi-ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol as biologically active substance and method for its preparation - Google Patents
S-succinic acid semi-ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol as biologically active substance and method for its preparation Download PDFInfo
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- CS269381B1 CS269381B1 CS884754A CS475488A CS269381B1 CS 269381 B1 CS269381 B1 CS 269381B1 CS 884754 A CS884754 A CS 884754A CS 475488 A CS475488 A CS 475488A CS 269381 B1 CS269381 B1 CS 269381B1
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- bromobutoxy
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Abstract
Předmětem řešení je nová biologicky účinná látka obecného vzorce I, kde symbol R1 značí methyl- nebo ethylskupinu, symboly R a RJ značí alkylskupinu s rovným nebo rozvětveným řetězcem s maximálně 3 atomy uhlíku. Jejich pesticidní účinky hyly vyzkoušeny například na hmyzu. Další část řešení je způsob přípravy látek obeoného vzorce I, spočívající v reakci 4- -(3-alkoxy-3-alkyl-2-brombutoxy)fenylalkanclu obecného vzorce II, kde symboly η p 7 R, R a RJ mají význam uvedený výše, s ekvimolárním množstvím anhydridu kyseliny jantarové a bezvodého pyridinu při teplotě 60 až 70 °C.The subject of the solution is a new biologically active substance of the general formula I, where the symbol R1 denotes a methyl or ethyl group, the symbols R and RJ denote a straight or branched chain alkyl group with a maximum of 3 carbon atoms. Their pesticidal effects have been tested, for example, on insects. Another part of the solution is a method of preparing substances of the general formula I, consisting in the reaction of 4- -(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkane of the general formula II, where the symbols η p 7 R, R and RJ have the meaning given above, with an equimolar amount of succinic anhydride and anhydrous pyridine at a temperature of 60 to 70 °C.
Description
Vynález se týká poloesteru kyseliny jantarové s 4-(3-alkoxy-3-alkyl-2-brombutoxy)fenylalkanolem jako biologicky účinné látky a způsobu jeho přípravy.The invention relates to a half-ester of succinic acid with 4-(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkanol as a biologically active substance and a method for its preparation.
Látka, jež je předmětem vynálezu, je příkladem nového typu pesticidu s volnou karboxylovou skupinou. Dosud připravené fyziologicky účinné estery vždy po hydrolýze na sloučeniny s volnou karboxylovou skupinou biologickou aktivitu ztratily.The substance which is the subject of the invention is an example of a new type of pesticide with a free carboxyl group. The physiologically active esters prepared so far have always lost their biological activity after hydrolysis to compounds with a free carboxyl group.
Podstatou vynálezu je poloester kyseliny jantarové s 4-(3-alkoxy-3-alkyl-2-brombutoxy)fenylalkanolem obecného vzorce I’The essence of the invention is a semi-ester of succinic acid with 4-(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkanol of the general formula I'
CH3(R1)C(0R2)-CHBr-CH2-0-^^ -CH(R3)0C0(CH2)2C00H(I),CH 3 (R 1 )C(OR 2 )-CHBr-CH 2 -O-^^ -CH(R 3 )OCO(CH 2 ) 2 COOH(I),
Ί 23 kde R značí methyl- nebo ethylskupinu, R a R značí alkylskupinu s maximálně 3 atomy uhlíku.Ί 23 where R denotes a methyl or ethyl group, R and R denote an alkyl group with a maximum of 3 carbon atoms.
Způsob přípravy poloesteru kyseliny jantarové s 4-(3-alkoxy-3-alkyl-2-brombutoxy)fenylalkanolem obecného vzorce I se vyznačuje tím, že se nechá reagovat 4-(3-alkoxy-3-alkyl-2-brombutoxy)fenylalkanol obecného vzorce IIThe method for preparing a succinic acid half-ester with 4-(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkanol of general formula I is characterized in that 4-(3-alkoxy-3-alkyl-2-bromobutoxy)phenylalkanol of general formula II is reacted
CH^(R1)C(OR^)-CHBr-CH2-O-^^-CH(R^)OH . (II), i kde symboly R , R a R mají výše uvedený význam, s ekvimolárním množstvím anhydridu kyseliny jantarové a bezvodého pyridinu při teplotě 60 až 70 cC, za vzniku poloesteru obecného vzorce I.CH^(R 1 )C(OR^)-CHBr-CH 2 -O-^^-CH(R^)OH . (II), i where the symbols R , R and R have the above meaning, with an equimolar amount of succinic anhydride and anhydrous pyridine at a temperature of 60 to 70 c C, to form a half-ester of general formula I.
Vynález je blíže objasněn na příkladu provedení, aniž se na tento příklad výlučně omezuje.The invention is explained in more detail by way of an example of embodiment, without being exclusively limited to this example.
PříkladExample
Směs 0,33 g (0,001 mol) 1-^4-(3-methoxy-3-methyl-2-brombutoxy)feny 1J -1-propanolu, 0,1 g anhydridu kyseliny jantarové a 87 mg bezvodého pyridinu byla zahřívána 7 hodin na 60 °C a potom byla ponechána stát přes noc. 'A mixture of 0.33 g (0.001 mol) of 1-[4-(3-methoxy-3-methyl-2-bromobutoxy)phenyl]-1-propanol, 0.1 g of succinic anhydride and 87 mg of anhydrous pyridine was heated at 60°C for 7 hours and then allowed to stand overnight.
Reakčni směs byla dělena sloupcovou chromatografií na silikagelu s 8 % hmot, vody (eluční činidlo petroléter obsahující až 75 % obj. diethyléteru). Bylo získáno 0,23 g (63 produktu.The reaction mixture was separated by column chromatography on silica gel with 8% w/w water (eluent petroleum ether containing up to 75% v/v diethyl ether). 0.23 g (63) of product was obtained.
IC spektrum (CC14, 5 %); 3535,28OO-33OO,26OO,268O(.) OH),2830(0 CH3 v 0CH3), 1767, 1739,1724,1712(0 C=O),1614,1588,1519( í aromatika),1383, 1371(J sCH3)cm-1.IC spectrum (CC1 4 , 5%); 3535,28OO-33OO,26OO,268O(.) OH),2830(0 CH 3 in 0CH 3 ), 1767, 1739,1724,1712(0 C=O),1614,1588,1519( í aromatics),1383, 1371(J with CH 3 )cm -1 .
13C-NMR spektrum:200MHz: 9.91(CH3CH2),22.16 a 23.77((0^)^00) .29.16(CH3CH,) .29.06 (CH2C00),28.90(H0C0CH2),49.92(CHBr),58.79(OCg,),69.73 (OCH,),76.24(0(¾^).77.66(CH-(g ),114.65(g)^)),127.98 «g)^),132.92(g) £-),157.91(g) £-0),171.42(000),177.71 (COOH). 13 C-NMR spectrum: 200MHz: 9.91(CH 3 CH 2 ),22.16 and 23.77((0^)^00) .29.16(CH 3 CH,) .29.06 (CH 2 C00),28.90(H0C0CH 2 ),49.92(CHBr),58.79(OCg,),69.73 (OCH,),76.24(0(¾^).77.66(CH-(g ),114.65(g)^)),127.98 «g)^),132.92(g) £-),157.91(g) £-0),171.42(000),177.71 (COOH).
Biologická účinnost byla zkoušena například na masařce Sarcophaga bullata, kdy se nakladená vajíčka téměř se 100%ní účinností nevylíhla (látka I, R1 = R2 = CH3, R^ = = C^^), aplikovaná dávka 5.10”^ mg v acetonu, dále potom na Tenbrio molitor, jehož morfogeneza byla potlačena již v koncentraci 10-2 mg.Biological efficacy was tested, for example, on the Sarcophaga bullata beetle, where the laid eggs did not hatch with almost 100% efficiency (substance I, R 1 = R 2 = CH 3 , R^ = = C^^), applied dose of 5.10”^ mg in acetone, then on Tenbrio molitor, whose morphogenesis was suppressed already at a concentration of 10 -2 mg.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884754A CS269381B1 (en) | 1988-07-01 | 1988-07-01 | S-succinic acid semi-ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol as biologically active substance and method for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884754A CS269381B1 (en) | 1988-07-01 | 1988-07-01 | S-succinic acid semi-ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol as biologically active substance and method for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS475488A1 CS475488A1 (en) | 1989-09-12 |
| CS269381B1 true CS269381B1 (en) | 1990-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS884754A CS269381B1 (en) | 1988-07-01 | 1988-07-01 | S-succinic acid semi-ester with 4- (3-alkoxy-3-alkyl-2-bromobutoxy) phenylalkanol as biologically active substance and method for its preparation |
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| CS (1) | CS269381B1 (en) |
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1988
- 1988-07-01 CS CS884754A patent/CS269381B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS475488A1 (en) | 1989-09-12 |
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