CS276621B6 - N-substituted-2,6-dialkylanilides and methods for their preparation - Google Patents

N-substituted-2,6-dialkylanilides and methods for their preparation Download PDF

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CS276621B6
CS276621B6 CS888650A CS865088A CS276621B6 CS 276621 B6 CS276621 B6 CS 276621B6 CS 888650 A CS888650 A CS 888650A CS 865088 A CS865088 A CS 865088A CS 276621 B6 CS276621 B6 CS 276621B6
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furyl
propenoyl
dialkylanilides
ethyl
substituted
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Alzbeta Doc Ing Cs Krutosikova
Vaclav Rndr Csc Konecny
Miloslava Ing Csc Dandarova
Jaroslav Prof Ing Drsc Kovac
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Univ Slovenska Tech
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Abstract

Fungicidne účinné 2,6-dialkylanilidy vzorca I, kde r! je methyl alebo ethyl, R2 je methyl alebo ethyl, R3 je vodík, 2-furfuryl, 5-(3,4-dichlórfenyl)-2-furfuryl, 1-hydroxy- -2-propyl, l-metoxy-2-propyl, 1-metoxykarbonyl-l-etyl a R je chlóracetyl, 3-(2-furyl) propenoyl, 3-(5-nitro-2-furyl)propenoyl, alebo benzoyl. Pripravujú sa pžsobením arylchloridu vzorca III na dialkylanilín vzorca II, kde R , R , R a R majú zhora uvedený význam.Fungicidally active 2,6-dialkylanilides of formula I, where R1 is methyl or ethyl, R2 is methyl or ethyl, R3 is hydrogen, 2-furfuryl, 5-(3,4-dichlorophenyl)-2-furfuryl, 1-hydroxy-2-propyl, 1-methoxy-2-propyl, 1-methoxycarbonyl-1-ethyl and R is chloroacetyl, 3-(2-furyl)propenoyl, 3-(5-nitro-2-furyl)propenoyl, or benzoyl. They are prepared by the action of an aryl chloride of formula III on a dialkylaniline of formula II, where R1, R2, R3 and R4 have the meanings given above.

Description

Vynález sa týká fungicídne účinných N-substituovaných 2,6-dialkylanilidov a sposobu ich přípravy.The invention relates to fungicidally effective N-substituted 2,6-dialkylanilides and the method of their preparation.

Z literatúry sú známe herbicídne účinné halogénacetanilidy Ger Offen 2328340 (1974) , Proc. Northeast. Weed Sci. Soc. 29,9 (1975); Swiss 581607 (1977), Belg. 870067 (1979), Ger Offen 2921509 (1979), Ger Offen 2,837863 (1980), Eur. Pat. Appl. 12158 (1980), Brit. 2043442 (1980), Brit. 2049427 (1980), Brit. 2073173 (1981), US 4317916 (1932).Herbicidally active haloacetanilides are known from the literature: Ger Offen 2328340 (1974), Proc. Northeast. Weed Sci. Soc. 29,9 (1975); Swiss 581607 (1977), Belg. 870067 (1979), Ger Offen 2921509 (1979), Ger Offen 2,837863 (1980), Eur. Pat. Appl. 12158 (1980), Brit. 2043442 (1980), Brit. 2049427 (1980), Brit. 2073173 (1981), US 4317916 (1932).

V uvedenej literatúre sa diskutuje súvislosE medzi herbicídnou účinnostou a chemickou štruktúrou účinnej látky. Medzi tieto zlúčeniny patří metolachlór, ktorý je aktívnou zložkou protitrávového herbicidu DUAL . Štyri stereoizoméry metolachloru boli připravené a ich absolutná konfigurácia bola dokázaná rontgenoštruktúrnou analýzou. Biologická aktivita jednotlivých stereoizomérov je rozdielna a je ovplyvnená konfiguráciou chirálneho centra; S-izoméry sú aktívnejšie ako R-antipódy.The literature discusses the relationship between herbicidal activity and the chemical structure of the active substance. These compounds include metolachlor, which is the active ingredient in the weed killer DUAL. Four stereoisomers of metolachlor have been prepared and their absolute configuration has been proven by X-ray structural analysis. The biological activity of the individual stereoisomers is different and is influenced by the configuration of the chiral center; S-isomers are more active than R-antipodes.

Štúdiom literatúry sa zistilo, že N-substituované-2,6-dialkylanilidy obsahujúce 5-(3,4-dichlórfenyl)-2-furfuryl, 3-(2-furyl)propenoyl a 3-(5-nitro-2-furyl)propenoyl zvyšok neboli doteraz připravené.A literature review revealed that N-substituted-2,6-dialkylanilides containing 5-(3,4-dichlorophenyl)-2-furfuryl, 3-(2-furyl)propenoyl and 3-(5-nitro-2-furyl)propenoyl moieties have not been prepared to date.

Predmetom vynálezu sú N-substituované-2,6-dialkylanilidy vzoreaThe invention relates to N-substituted-2,6-dialkylanilides of the formula

kde R1 je metyl, etyl 2where R 1 is methyl, ethyl 2

R je metyl, etylR is methyl, ethyl

R^ je H; 2-furfuryl, 5-(3,4-dichlórfenyl)-2-furfuryl, l-hydroxy-2-propyl, 1-metoxy-2-propyl, 1-metoxykarbonyl-l-etylR 1 is H; 2-furfuryl, 5-(3,4-dichlorophenyl)-2-furfuryl, 1-hydroxy-2-propyl, 1-methoxy-2-propyl, 1-methoxycarbonyl-1-ethyl

R4 je chlóracetyl, 3-(2-furyl)propenoyl, 3-(5-nitro-2-furyl)propenoyl, benzoyl.R 4 is chloroacetyl, 3-(2-furyl)propenoyl, 3-(5-nitro-2-furyl)propenoyl, benzoyl.

Podstata sposobu přípravy N-substituovaných-2,6-dialkylanilidov spočívá v tom, že na N-substituovaný-2,6-dialkylanilín vzorea II /«/ 'The essence of the method for the preparation of N-substituted-2,6-dialkylanilides is that the N-substituted-2,6-dialkylaniline of the formula II /«/ '

kde R , R a R° majú horeuvedený význam sa posobí acylchloridom vzorea IIIwhere R, R and R° have the above meaning is reacted with an acyl chloride of formula III

R4-C1 (III), kde R4 má horeuvedený význam .R 4 -C1 (III), where R 4 has the above meaning.

v benzéne alebo toluéne v přítomnosti uhličitanu sodného pri teplotách 25 až 60 *C.in benzene or toluene in the presence of sodium carbonate at temperatures of 25 to 60 *C.

Výhody sposobu přípravy zlúčenín I podlá vynálezu spočívájú okrem iného y tom, že sa reakcia N-substituovaných-2,6-dialkylanilínov s acylchloridmi uskutečňuje v nenáročných podmienkach v jednom stupni s dobrým výtažkom. ·The advantages of the process for preparing compounds I according to the invention lie, inter alia, in the fact that the reaction of N-substituted-2,6-dialkylanilines with acyl chlorides is carried out under undemanding conditions in one step with good yield.

Niektoré z připravených zlúčenín prejavili antifungálnu aktivitu. Sledováním štandardnou metodou zlúčeniny IV, V, VI a XIX vytvořili sterilnú zónu u Phytoptora infestans, IV, V, VI, XVIII, XXII, XXIII a XXIV u Botrytis cineres, IV, V, VI, VII, XVIII, XXII,Some of the prepared compounds showed antifungal activity. By standard method, compounds IV, V, VI and XIX formed a sterile zone in Phytoptora infestans, IV, V, VI, XVIII, XXII, XXIII and XXIV in Botrytis cineres, IV, V, VI, VII, XVIII, XXII,

XXIII, XXIV u Fusarium nivale (tab. 11).XXIII, XXIV in Fusarium nivale (tab. 11).

Příklad 1Example 1

N-3-(2-Furyl)propenoyl-2,6-dialkylanilidy (I-III).N-3-(2-Furyl)propenoyl-2,6-dialkylanilides (I-III).

K suspenzii 2,6-dialkylanilinu (0,02 mol) a uhličitanu sodného (2,12 g, 0,02 mol) v benzéne (10 ml), sa přidá 3- 2-furylpropénoylchlorid (3,13 g, 0,02 mol) v benzene (15 ml) pri teplote 25 'c. Reakčná zmes se mieša pri laboratórnej teplote eště 1 hodinu. Vylúčený chlorid sodný sa odfiltruje, filtrát sa zahustí vo vákuu a zvyšok sa prekryštalizuje z etanolu. Podobné sa pri použití 3-(5-nitro-2-furyl)propenoyl chloridu připraví N-3-(5-nitro-2-furyl)propénoyl-2,6 -dialkylanilidy (IV-VI). Konstanty zlúčenín I - VI sa uvádzajú v tab. 1 a 6.To a suspension of 2,6-dialkylaniline (0.02 mol) and sodium carbonate (2.12 g, 0.02 mol) in benzene (10 ml), 3-2-furylpropenoyl chloride (3.13 g, 0.02 mol) in benzene (15 ml) was added at 25 °C. The reaction mixture was stirred at room temperature for another 1 hour. The precipitated sodium chloride was filtered off, the filtrate was concentrated in vacuo and the residue was recrystallized from ethanol. Similarly, using 3-(5-nitro-2-furyl)propenoyl chloride, N-3-(5-nitro-2-furyl)propenoyl-2,6 -dialkylanilides (IV-VI) were prepared. The constants of compounds I - VI are given in Tables 1 and 6.

Příklad 2Example 2

N-(2-Furfuryl)-N- 3-(2-furyl)propénoyl-2,6-dialkylanilidy (VII - IX)N-(2-Furfuryl)-N-3-(2-furyl)propenoyl-2,6-dialkylanilides (VII - IX)

K suspenzii N-(2-furfuryl)-2,6-dialkylanilínu ' (0,02 mol) a uhličitanu sodného (2,12 g, 0,02 mol) v toluéne (15 ml) sa přidá 3-(2-furyl)propenoylchlorid (3,13 g, 0,02 mol) v benzéne (15 ml) pri teplote 25 'c. Reakčná zmes sa mieša pri laboratórnej teplote ešte 3 h, přefiltruje sa, po oddestilovaní rozpúštiadel vo vákuu sa prekryštalizuje z etanolu. Podobné sa připravili N-(2-furfuryl)-N- 3-(5-nitró-2-furyl) -propénoyl í -2,6-dialkylanilidy (X - XII). Výtažky, fyzikálně konstanty a spektrálné charakteristiky sú uvedené v tab. 2 a 7.To a suspension of N-(2-furfuryl)-2,6-dialkylaniline (0.02 mol) and sodium carbonate (2.12 g, 0.02 mol) in toluene (15 ml) was added 3-(2-furyl)propenoyl chloride (3.13 g, 0.02 mol) in benzene (15 ml) at 25 °C. The reaction mixture was stirred at room temperature for another 3 h, filtered, and after distilling off the solvents in vacuo, it was recrystallized from ethanol. N-(2-furfuryl)-N-3-(5-nitro-2-furyl)-propenoyl -2,6-dialkylanilides (X - XII) were prepared similarly. The yields, physical constants, and spectral characteristics are given in Tables 2 and 7.

Přiklad 3Example 3

N- [,5-(3,4-dichlórfenyl)-2-furfurylJ -N-chlóracetyl-2-etyl-6-metylanilid (XIII)N-[,5-(3,4-dichlorophenyl)-2-furfuryl]-N-chloroacetyl-2-ethyl-6-methylanilide (XIII)

K suspenzii N- £5-(3,4-dichlórfenyl)-2-furfurylJ -2-etyl-6-metylanilinu (5,4 g) a uhličitanu sodného (3,1 g) v benzéne (15 ml) sa přidá chlóracetylchlorid (1,6 ml) v benzéne (10 ml) pri teplote 10 ’c. Reakčná zmes sa mieša este 4 h pri laboratórnej teplote, přefiltruje sa a zriedi sa etylacetátom. Premyje sa vodou, 10%ným roztokom kyseliny chlorovodíkovéj, vodou, nasýteným roztokom chloridu sodného a vysuší sa síranom sodným. Rozpúštadlá sa oddestilujú vo vákuu a zvyšok sa udržuje vo vákuu (66 Pa) pri teplote 60 *C počas 4 h. Získala sa zlúčenína XIII ako žitý olej.To a suspension of N-£5-(3,4-dichlorophenyl)-2-furfurylJ -2-ethyl-6-methylaniline (5.4 g) and sodium carbonate (3.1 g) in benzene (15 ml) was added chloroacetyl chloride (1.6 ml) in benzene (10 ml) at 10 °C. The reaction mixture was stirred for another 4 h at room temperature, filtered and diluted with ethyl acetate. It was washed with water, 10% hydrochloric acid solution, water, saturated sodium chloride solution and dried over sodium sulfate. The solvents were distilled off in vacuo and the residue was kept in vacuo (66 Pa) at 60 °C for 4 h. Compound XIII was obtained as a white oil.

Zlúčeniny XIV - XVI sa připravili podobné z odpovedajúcich acylchloridov. Po oddestilovaní rozpúštadiel sa vypadnuté pevné látky prekryštalizovali zo zriedeného etanolu. Výtažky a fyzikálně konstanty zlúčenín XIII - XVI sa uvádzajú v tab. 3, ich spektrálné charakteristiky v tab. 8.Compounds XIV - XVI were prepared similarly from the corresponding acyl chlorides. After distilling off the solvents, the precipitated solids were recrystallized from dilute ethanol. The yields and physical constants of compounds XIII - XVI are given in tab. 3, their spectral characteristics in tab. 8.

Příklad 4Example 4

N-(l-Hydroxy-2-propyl)-N- £ 3-(2-furyl)propénoylJ -2,6-dimetylanilid (XVII)N-(1-Hydroxy-2-propyl)-N-3-(2-furyl)propenoyl-2,6-dimethylanilide (XVII)

K suspenzii N-(l-hydroxy-2-propyl)-2,6-dimetylanilínu (0,02 mol) a uhličitanu sod- ného (2,12 g, 0,02 mol) v benzéne (15 ml) sa přidá 3-(2-furyl)propénoylchlorid (3,13 g, 0,02 mol) v benzéne (15 ml) pri teplote 25 C. Reakčná zmes sa mieša pri laboratórnej teplote 5 h, přefiltruje sa, zriedi sa etylacetátom. Premyje sa vodou 10%ným roztokom kyseliny chlorovodíkovéj, vodou a 5%ným roztokom chloridu sodného. Organická vrstva.sa vysuší síranom sodným a rozpúštadlá sa oddestilujú vo vákuu. Surový produkt sa kryštalizuje zo zmesi benzén-hexán 1:1. Podobné sa připravili zlúčeniny XVIII - XXIV, ich výtažky, fyzikálně konstanty a spektrálné charakteristiky sú v tab. 4 a 9. . .To a suspension of N-(1-hydroxy-2-propyl)-2,6-dimethylaniline (0.02 mol) and sodium carbonate (2.12 g, 0.02 mol) in benzene (15 ml) was added 3-(2-furyl)propenoyl chloride (3.13 g, 0.02 mol) in benzene (15 ml) at 25 C. The reaction mixture was stirred at room temperature for 5 h, filtered, diluted with ethyl acetate. It was washed with water, 10% hydrochloric acid solution, water and 5% sodium chloride solution. The organic layer was dried over sodium sulfate and the solvents were distilled off in vacuo. The crude product was crystallized from a 1:1 benzene-hexane mixture. Compounds XVIII - XXIV were prepared similarly, their yields, physical constants and spectral characteristics are in Tables 4 and 9. . .

Příklad 5Example 5

N-(1-metoxykarbonyl)-1-etyl)-N- 3-(2-furyl)propénoyl : 2,6-dimetylanilid (XXV)N-(1-methoxycarbonyl)-1-ethyl)-N-3-(2-furyl)propenoyl : 2,6-dimethylanilide (XXV)

K suspenzii N-(1-metoxykarbonyl-l-etyl)-2,6-dialkylanilinu (0,02 mol) a uhličitanu sodného (2,12 g, 0,02 mol) v benzéne (15 ml) sa přidá 3-(2-furyl)propenoylchlorid (3,13 g, 0,02 mol) v benzéne (15 ml) pri teplote 25 ‘c. Reakčná zmes sa mieša pri laboratorně j teplote 3 h. Ďalší postup ako v příklade 4.To a suspension of N-(1-methoxycarbonyl-1-ethyl)-2,6-dialkylaniline (0.02 mol) and sodium carbonate (2.12 g, 0.02 mol) in benzene (15 ml) was added 3-(2-furyl)propenoyl chloride (3.13 g, 0.02 mol) in benzene (15 ml) at 25 °C. The reaction mixture was stirred at room temperature for 3 h. The further procedure was as in Example 4.

Podobné sa připravili zlúčeniny XXVI - XXIX. Zlúčeniny XXVII - XXIX po oddestilovaní rozpúštiadel vypadli ako pevné látky a krystalizovali sa zo zriedeného etanolu. Výtažky, fyzikálně konstanty a spektrálné charakteristiky sú v tab. 5 a 10.Compounds XXVI - XXIX were prepared similarly. Compounds XXVII - XXIX, after distillation of the solvents, precipitated as solids and crystallized from dilute ethanol. The yields, physical constants and spectral characteristics are in Tab. 5 and 10.

^H-NMR spektrá sa namerali na spektrometr! Tesla BS 487C v hexadeuteroacetóne a hexadeuterodimetylsulfoxide pri 25 ‘c s použitím tetrametylsilánu ako interného standardu. Použité rozpúštadlá u jednotlivých zlúčenín sú uvedené v tabulkách 6 až 10.^H-NMR spectra were measured on a Tesla BS 487C spectrometer in hexadeuteroacetone and hexadeuterodimethylsulfoxide at 25 'c using tetramethylsilane as an internal standard. The solvents used for the individual compounds are listed in Tables 6 to 10.

TABUÉKA 1TABLE 1

N- £3-(2-Furyl)propenoylJ - a N- [3-(5-nitro-2-furyl)propenoylj-2,6-dialkylanilidyN-[3-(2-Furyl)propenoyl]- and N-[3-(5-nitro-2-furyl)propenoyl]-2,6-dialkylanilides

oabout

-CH=CH-C-NHR2 -CH=CH-C-NHR 2

Zlúč. Compound. R R R1 R 1 R2 R2 Sumárny vz. MH Summary version MH Vypočít./Nájdené % C % Η % N Calculated/Found % C % Η % N T.t. *C Výtažok % M.t. *C Yield % I I H H chh 33 ch3 ch 3 C15H15NO2 C15H15NO2 ​ ​ 74,66 74.66 6,26 6.26 5,80 5.80 184 184 až until 187 187 241,3 241.3 75,01 75.01 6,21 6.21 5,98 5.98 78 78 II II H H ch3 ch 3 C2H5 C2H5 ​ C16H17NO2 C16H17NO2 ​ ​ 75,27 75.27 6,71 6.71 5,49 5.49 201 201 až until 202 202 255,3 255.3 75,39 75.39 6,60 6.60 5,78 5.78 82 82 III III H H C2H5 C2H5 ​ c2h5 c 2 h 5 C17H19NO2 C17H19NO2 ​ ​ 75,82 75.82 7,11 7.11 5,20 5.20 187 187 až until 190 190 269,3 269.3 75,42 75.42 7,18 7.18 5,27 5.27 93 93 IV IV N02 N0 2 chh 33 ch3 ch 3 C15H14N2°4 C15H14N2 ° 4 62,93 62.93 4,92 4.92 9,78 9.78 201 201 až until 202 202 286,3 286.3 62,73 62.73 4,82 4.82 9,58 9.58 97 97 v in N°2 N°2 . ch3 . ch 3 C2H5 C2H5 ​ C16H16N2°4 C 16 H 16 N 2°4 63,99 63.99 5,37 5.37 9,32 9.32 192 192 až until 195 195 300,3 300.3 63,90 63.90 5,27 5.27 9,22 9.22 97 97 VI VI no2 no 2 C2H5 C2H5 ​ C2H5 C2H5 ​ C17H18N2°4 C17H18N2 ° 4 64,97 64.97 5,77 5.77 9,13 9.13 190 190 až until 193 193 314,3 314.3 64,77 64.77 5,67 5.67 9,10 9.10 76 76

TABUÍ.KA 2TABLE 2

N-(2-Furfuryl)-N- £3-(5-R-2-furyl)J propénoyl-2,6-dialkylanilidyN-(2-Furfuryl)-N-3-(5-R-2-furyl)propenoyl-2,6-dialkylanilides

Z1ÚČ . Z1ÚČ . R R R1 R 1 R2 R2 Sumárny vz . MH Summary of the MH Vypočít./Nájdené Calculated/Found T.t. , Výtažo) T.t. , Elevator) ’c k % ’c k % % C %C % Η % H % N %N VII VII H H ch3 ch 3 ch3 ch 3 C20H19NO3 C20H19NO3 ​ ​ 74,74 74.74 5,96 5.96 4,35 4.35 94 až 94 to 95 95 321,4 321.4 74,26 74.26 5,86 5.86 4,32 4.32 80 80 VIII VIII H H ch3 ch 3 C2H5 C2H5 ​ C21H21NO3 C21H21NO3 ​ ​ 75,20 75.20 6,31 6.31 4,18 4.18 100 až 100 to 102 102 335,4 335.4 74,94 74.94 6,18 6.18 4,56 4.56 90 90 IX IX H H C2H5 C2H5 ​ C2H5 C2H5 ​ C22H23NO3 C22H23NO3 ​ ​ 76,63 76.63 6,63 6.63 4,00 4.00 104 až 104 to 106 106 349,4 349.4 75,64 75.64 6,81 6.81 4,11 4.11 78 78 X X no2 no 2 chh 33 ch3 ch 3 C20H18N2°5 C20H18N2 ° 5 65,56 65.56 4,95 4.95 7,64 7.64 151 až 151 to 154 154 366,4 366.4 65,86 65.86 4,97 4.97 7,64 7.64 94 94 XI XI N°2 N°2 ch3 ch 3 C2H5 C2H5 ​ C21H20N2°5 C21H20N2 ° 5 66,31 66.31 5,30 5.30 7,36 7.36 92 až 92 to 96 96 380,4 380.4 66,39 66.39 5,27 5.27 7,30 7.30 96 96 XII XII n°2 No. 2 C2H5 C2H5 ​ C2H5 C2H5 ​ C22H22N2°5 C 22 H 22 N 2°5 67,00 67.00 5,62 5.62 7,10 7.10 100 až 100 to 105 105 394,4 394.4 66,82 66.82 5,48 5.48 7,00 7.00 94 94

N- 1.5-(3,4-dichlórfenyl)-2-furfuryl ] -N-R4-2-etyl-6-metylanilidy (XIII - XVI)N-1,5-(3,4-dichlorophenyl)-2-furfuryl]-NR 4 -2-ethyl-6-methylanilides (XIII - XVI)

TABUÍKA 3TABLE 3

c2h5 c 2 h 5

Zlúč. Compound. R4 R 4 Sumář.vzorec ΜΗ Summary.formula ΜΗ Vypočít./Nájdené Calculated/Found T.t. 'c T.t. 'c % C %C % H % H % Cl % Cl % N %N Výřažok Cut-out % % XIII XIII C1CH2CO C1CH2CO C22H20C13NO2 C22H20C13NO2 ​ ​ ​ 60,51 60.51 4,62 4.62 24,35 24.35 3,20 3.20 žitý olej rye oil 436,7 436.7 60,12 60.12 4,42 4.42 25,82 25.82 3,12 3.12 81 81 XIV XIV Qco What C27H23C12NO2 C27H23C12NO2 ​ ​ ​ 69,83 69.83 4,99 4.99 15,27 15.27 3,07 3.07 122 až 122 to 123 123 o \0' -CH=CHCO o \ 0 ' -CH=CHCO 464,4 464.4 69,63 69.63 4,79 4.79 15,07 15.07 3,18 3.18 76 76 XV XV C27H23C12NO3 C27H23C12NO3 ​ ​ ​ 47,50 47.50 4,83 4.83 14,75 14.75 2,91 2.91 133 až 133 to 135 135 480,4 480.4 67,36 67.36 4,75 4.75 14,62 14.62 2,73 2.73 74 74 XVI XVI °2N~\ J^-CH=CHC0 °2 N ~\ J^-CH=CHC0 Cq^HooC1oNo0c 27 22 225 Cq^H oo C1 o N o 0 c 27 22 225 50,29 50.29 4,22 4.22 13,49 13.49 5,33 5.33 164 až 164 to 167 167 525,4 525.4 50,20 50.20 4,12 4.12 13,33 13.33 5,11 5.11 88 88

N- L(l-Hydroxy)resp. l-metoxy-2-propyl] -N- [3-(2-furyl) resp. 3-(5-nitro-2-furyl) propenoylJ -2,6-dialkylanilidy (XVII - XXIV)N-L(1-Hydroxy) or 1-methoxy-2-propyl]-N-[3-(2-furyl) or 3-(5-nitro-2-furyl)propenoyl-2,6-dialkylanilides (XVII - XXIV)

TABUtKA 4TABLE 4

Zlúč . Combine . R R R1 R 1 R2 R2 R5 R5 Sum.vzorec MH Sum.formula MH Vypoč % C Calculate % C ./Nájdené % Η % N ./Found % Η % N T.t. c Výtažok T.t. c Extract XVII XVII H H ch3 ch 3 CH3 CH 3 H H C18H21NO3 C18H21NO3 ​ ​ 72,23 72.23 7,07 7.07 4,68 4.68 77 až 77 to 79 79 299,3 299.3 72,03 72.03 7,12 7.12 4,82 4.82 62 62 XVIII XVIII H H ch3 ch 3 C2H5 C2H5 ​ H H C19H23NO3 C19H23NO3 ​ ​ 72,82 72.82 7,40 7.40 4,59 4.59 82 až 82 to 83 83 313,4 313.4 72,88 72.88 7,21 7.21 4,02 4.02 72 72 XIX XIX N°2 No. 2 ch3 ch 3 CH3 CH 3 H H C18H20N2°5 C18H20N2 ° 5 63,53 63.53 5,92 5.92 8,23 8.23 125 až 125 to 126 126 340,3 340.3 63,56 63.56 5,90 5.90 7,88 7.88 76 76 XX XX H H CH3 CH 3 ch3 ch 3 ch3 ch 3 Ci9 H23N°3 Ci 9 H 2 3 N°3 72,82 72.82 7,40 7.40 4,59 4.59 68 až 68 to 71 71 313,4 313.4 72,48 72.48 7,26 7.26 4,22 4.22 78 78 XXI XXI H H C2 h 5 C 2 hours 5 ch3 ch 3 ch3 ch 3 C20H25NO3 C20H25NO3 ​ ​ 73,37 73.37 7,70 7.70 4,29 4.29 žitý olej rye oil 327,4 327.4 73,15 73.15 7,62 7.62 4,21 4.21 69 69 XXII XXII N°2 N°2 chh 33 chh 33 chh 33 C19H22N2°5 C19H22N2 ° 5 63,67 63.67 6,19 6.19 7,82 7.82 126 až 126 to 128 128 358,4 358.4 63,82 63.82 6,10 6.10 7,78 7.78 96 96 XXIII XXIII N°2 N°2 ch3 ch 3 C2H5 C2H5 ​ CH3 CH 3 C20H24N2°5 C20H24N2 ° 5 64,50 64.50 6,50 6.50 7,52 7.52 92 až 92 to 94 94 372,4 372.4 64,32 64.32 6,40 6.40 7,42 7.42 93 93 XXIV XXIV no2 no 2 C2H5 C2H5 ​ C2H5 C2H5 ​ ch3 ch 3 C21H26N2°5 C21H26N2 ° 5 65,28 65.28 6,78 6.78 7,25 7.25 77 až 77 to 82 82 386,4 386.4 65,08 65.08 6,60 6.60 7,05 7.05 93 93

TABUtKA 5TABLE 5

N-(1-Metoxykarbonyl-l-etyl)-N- L3-(2-furyl resp. 5-nitro-2-furyl)propenoylj -2,6-dimetylanilidy (XXV - XXIX)N-(1-Methoxycarbonyl-1-ethyl)-N-L3-(2-furyl or 5-nitro-2-furyl)propenoyl-2,6-dimethylanilides (XXV - XXIX)

Zlúč. Compound. R R R1 R 1 R2 R2 Sum.vzorec MH Sum.formula MH Vypoč./Nájdené Calculated/Found T.t. 'c VýEažok T.t. 'c Extract % C- % C- 0 % 0% % N %N XXV XXV H H ch3 ch 3 CH3 CH 3 ci9H2iNO4 c i9 H 2i NO 4 69,70 69.70 6,46 6.46 4,27 4.27 žitý visk. olej rye visc. oil 327,4 327.4 69,20 69.20 6,06 6.06 4,68 4.68 76 76 XXVI XXVI H H CH3 CH 3 C2H5 C2H5 ​ C20H23^°4 C20H23 ^ °4 70,36 70.36 6,79 6.79 4,10 4.10 žitý visk. olej rye viscose oil 341,4 341.4 70,06 70.06 7,02 7.02 4,04 4.04 XXVII XXVII no2 no 2 ch3 ch 3 CH3 CH 3 C19H20N2°6 C19H20N2 ° 6 61,28 61.28 5,41 5.41 7,52 7.52 174 až 175 174 to 175 372,4 372.4 61,36 61.36 5,48 5.48 7,70 7.70 95 95 XXVIII XXVIII no2 no 2 ch3 ch 3 C2H5 C2H5 ​ C20H22N2°6 C20H22N2 ° 6 62,17 62.17 5,74 5.74 7,25 7.25 119 až 122 119 to 122 386,4 386.4 62,60 62.60 5,54 5.54 7,17 7.17 84 84 XXIX XXIX N°2 N°2 C2H5 C2H5 ​ C2H5 C2H5 ​ C21H24N2°6 C 21 H 24 N 2°6 63,00 63.00 6,04 6.04 6,99 6.99 132 až 134 132 to 134 400,4 400.4 63,20 63.20 6,40 6.40 7,15 7.15 90 90

TABULKA 6 XH NMR dátaa ( ppm; J, Hz) zlúčenín I - VITABLE 6 X H NMR data and (ppm; J, Hz) of compounds I - VI

-CHsCH-C * 9 11 0-CHsCH-C * 9 11 0

Proton JH, H Proton J H, H Zlúčenina Compound I I II II III III IV IV V In VI VI H-3 H-3 6,75dd 6.75dd 6,72dd 6.72dd 6,70dd 6.70dd 7,08d 7.08d 7,06d 7.06d 7,04d 7.04d H-4 H-4 6,59dd 6.59dd 6,54dd 6.54dd 6,55dd 6.55dd 7,58d 7.58d 7,57d 7.57d 7,56d 7.56d H-5 H-5 7,69dd 7.69dd 7,64dd 7.64dd 7,69dd 7.69dd - - - - - - H-6 H-6 7,49d 7.49d 7,44d 7.44d 7,44d 7.44d 7,53d 7.53d 7,52d 7.52d 7,52d 7.52d H-7 H-7 6,81d 6.81d 6,76d 6.76d 6,78d 6.78d 7,08d 7.08d 7,08d 7.08d 7,09d 7.09d pj pj 7,05bs 7.05bs 7,08bs 7.08bs 7,12bs 7.12bs 7,09bs 7.09bs 7,18bs 7.18bs 7,15bs 7.15bs R1 R 1 2,22s 2.22s 2,18s 2.18s 2,60q l,12t 2.60q l.12t 2,22s 2.22s 2,22s 2.22s 2,62q l,12t 2.62q 1.12t R2 R2 2,22s 2.22s 2,60q l,10t 2.60q l.10t 2,60q l,12t 2.60q l.12t 2,22s 2.22s 2,62q l,12t 2.62q 1.12t 2,62q l,12t 2.62q 1.12t NH NH 8,81bs 8.81bs 8,72bs 8.72bs 8,75bs 8.75bs 9,00bs 9.00bs 9,00bs 9.00bs 9,00bs 9.00bs J3,4 J 3.4 3,2 3.2 3,2 3.2 3,2 3.2 3,9 3.9 3,9 3.9 3,9 3.9 J6,7 J 6.7 15,5 15.5 15,5 15.5 15,5 15.5 15,6 15.6 15,6 15.6 15,6 15.6

Merané v hexadeuteroacetóneMeasured in hexadeuteroacetone

TABUtKA 7 1H NMR dátaa ( O', ppm; J, Hz) zlúčenín VII - XIITABLE 7 1 H NMR data and (O', ppm; J, Hz) of compounds VII - XII

Proton Proton Zlúčenina Compound JH, H J H, H VII VII VIII VIII IX IX X X XI XI XII XII H-3 H-3 6,63dd 6.63dd 6,61dd 6.61dd 6,65dd 6.65dd 7,02dd 7.02dd 7,00d 7.00d 7,00a 7.00a H-4 H-4 6,47dd 6.47dd 6,43dd 6.43dd 6,45dd 6.45dd 7,49d 7.49d 7,45d 7.45d 7,47d 7.47d H-5 H-5 7,45dd 7.45dd 7,41dd 7.41dd 7,45dd 7.45dd - - - - - - H-6 H-6 7,49d 7.49d 7,50d 7.50d 7,48d 7.48d 7,56d 7.56d 7,54d 7.54d 7,55d 7.55d H-7 H-7 6,00d 6.00d 6,Old 6,Old 6,Old 6,Old 6,28d 6.28d 6,28d 6.28d 6,30d 6.30d H-3 ' H-3 ' 6,22dd 6.22dd 6,20dd 6.20dd 6,20dd 6.20dd 6,23dd 6.23dd 6,20d 6.20d 6,22dd 6.22dd H-4' H-4' 6,33dd 6.33dd 6,30dd 6.30dd 6,30dd 6.30dd 6,34dd 6.34dd 6,30dd 6.30dd 6,32dd 6.32dd H-5 ' H-5 ' 7,40dd 7.40dd 7,37dd 7.37dd 7,40dd 7.40dd 7,42dd 7.42dd 7,44dd 7.44dd 7,40dd 7.40dd H arom H aroma 7,12bs 7.12bs b b b b 7,19bs 7.19bs b b c c CH2 CH 2 4,85s 4.85s 4,72d 4,82d 4.72d 4.82d 4,85s 4.85s 4,87s 4.87s 4,81d 4,96d 4.81d 4.96d 4,87s 4.87s R1 R 1 1,93s 1.93s 1,90s 1.90s 2,32q l,03t 2.32q 1.03t 1,95s 1.95s 1,95s 1.95s 2,32q l,05t 2.32q 1.05t R2 R2 1,93s 1.93s 2,35q l,03t 2.35q 1.03t 2,32q l,03t 2.32q 1.03t 1,95s 1.95s 2,37q l,10t 2.37q 1.10t 2,32q l,05t 2.32q 1.05t J3,4 J 3.4 3,2 3.2 3,2 3.2 3,2 3.2 3,9 3.9 3,9 3.9 3,9 3.9 J6,7 J 6.7 15,2 15.2 15,2 15.2 15,2 15.2 15,4 15.4 15,5 15.5 15,5 15.5

a Merané v hexadeuteroacetóne; 7,0-7,4 m; c 7,2-7,3 m. a Measured in hexadeuteroacetone; 7.0-7.4 m; c 7.2-7.3 m.

TABUtKA 8 1H NMR dátaa ( ppm; J, Hz) zlúčenín XIII - XVITABLE 8 1 H NMR data and (ppm; J, Hz) of compounds XIII - XVI

c2h5 c 2 h 5

Proton JH, H Proton J H, H Zlúčenina Compound XVI XVI XIII XIII XIV XIV XV XV II—3 II—3 6,45d 6.45d 6,47d 6.47d 6,40d 6.40d 6,73d 6.73d H-4 H-4 7,02d 7.02d 7,02d 7.02d 6,98d 6.98d 7,30d 7.30d ch2-n ch 2 -n 4,93d 4.93d 4,95bs 4.95bs 4,92d 4.92d 4,92s 4.92s 4,79d 4.79d 4,82d 4.82d chh 33 1,96s 1.96s 2,00s 2.00s 1,92s 1.92s 1,95s 1.95s ch 3-ch2 ch 3 -ch 2 2,37q 2.37q 2,45q 2.45q 2,35q 2.35q 2,35q 2.35q CH3-CH2 CH3 - CH2 l,00t 1.00t 0,95t 0.95t 0,98t 0.98t l,00t 1.00t Η-6 H-6 - - 7,47d 7.47d 6,41d 6.41d H-7 H-7 - - . . 5,90d 5.90d 4,92d 4.92d H-3' H-3' - - 6,78dd 6.78dd 7,38dd 7.38dd H-4' H-4' - - - - 6,50dd 6.50dd 7,92dd 7.92dd H-5' H-5' - - - - 7,61dd 7.61dd - - ch2ci ch 2 ci 3,82s 3.82s - - - - . - . - NH NH - - - - - - - - J3,4 J 3.4 3,2 3.2 3,4 3.4 3,2 3.2 3,5 3.5 J6,7 J 6.7 - - - - 15,2 15.2 15,2 15.2

a Merané v hexadeuterodimetylsulfoxide; H arom : 7,10 - 7,80 m a Measured in hexadeuterodimethylsulfoxide; H arom : 7.10 - 7.80 m

TABULKA 9 ΤΗ NMR dátaa ( C ppm; J, Hz) zlúčenín . XVII - XXIVTABLE 9 Τ Η NMR data and (C ppm; J, Hz) of compounds XVII - XXIV

Proton JH, H Proton J H, H XVII XVII XVIII XVIII Z 1 ú XIX From 1 to XIX č e n i n a a n i n a XX XX XXI XXI XXII XXII XXIII XXIII XXIV XXIV H-3 H-3 6,65dd 6.65dd 6,64dd 6.64dd 6,98d 6.98d 6,61dd 6.61dd 6,61dd 6.61dd 6,98d 6.98d 6,97d 6.97d 6,97d 6.97d H-4 H-4 6,44dd 6.44dd 6,45dd 6.45dd 7,46d 7.46d 6,43dd 6.43dd 6,43dd 6.43dd 7,48d 7.48d 7,46d 7.46d 7,47d 7.47d H-5 H-5 7,43dd 7.43dd 7,46dd 7.46dd - - 7,42dd 7.42dd 7,43dd 7.43dd H-6 H-6 7,45d 7.45d 7,42d 7.42d 7,50d 7.50d 7,43d 7.43d 7,40d 7.40d 7,496 7,496 7,47d 7.47d 7,47d 7.47d H-7 H-7 5,92d 5.92d 5,92d 5.92d 6,20d 6.20d 5,91d 5.91d 5,91d 5.91d 6,20d 6.20d 6,22d 6.22d 6,24d 6.24d JJ arom JJ aroma 7,17bs 7.17bs b b 7,21bs 7.21bs 7,20bs 7.20bs b b 7,22bs 7.22bs b b 7,32bs 7.32bs CH2 CH 2 3,60dd 3.60dd 3,46dd 3.46dd 3,50dd 3.50dd 3,72dd 3.72dd 3,74dd 3.74dd 3,75dd 3.75dd ch2~oh ch 2 ~oh 3,80m 3.80m 3,80m 3.80m 3,90m 3.90m 3,61m 3.61m 3,60m 3.60m CH CH 4,10m 4.10m 4,08m 4.08m 4,10m 4.10m 4,25m 4.25m 4,25m 4.25m 4,25m 4.25m 4,25m 4.25m 4,25m 4.25m OH OH 4,50t 4.50t 4,40t 4.40t 4,27t 4.27t - - - - och3 oh 3 - - - - 3,20s 3.20s 3,22s 3.22s 3,20s 3.20s 3,22s 3.22s 3,21s 3.21s ch3-ch ch 3 -ch l,17d 1,17d l,19d 1,19d l,18d 1,18d l,15d 1.15d l,15d 1.15d l,18d 1,18d l,14d 1,14d l,12d 1,12d R1 R 1 2,22s 2.22s 2,17s 2.17s 2,21 2.21 2,18s 2.18s 2,18s 2.18s 2,20s 2.20s 2,20s 2.20s 2,56q 2.56q l,18t 1.18t R2 R2 2,16s 2.16s 2,63q 2.63q 2,26 2.26 2,22s 2.22s 2,58q 2.58q 2,22s 2.22s 2,75q 2.75q 2,61q 2.61q 1,24 1.24 l,16t 1.16t l,20t 1.20t l,18t 1.18t J3,4 J 3.4 3,3 3.3 3,3 3.3 3,8 3.8 3,3 3.3 3,3 3.3 4,00 4.00 4,00 4.00 4,00 4.00 J6,7 J 6.7 15,1 15.1 15,1 15.1 15,2 15.2 15,2 15.2 15,2 15.2 15,5 15.5 15,5 15.5 15,5 15.5

3. — b3. — b

Merané v hexadeuteroacetone, 7,20 - 7,30 mMeasured in hexadeuteroacetone, 7.20 - 7.30 m

TABUĚKA 10 1H NMR dátaa ppm; J, Hz) zlúčenín XXV - XXIXTABLE 10 1 H NMR data ( ppm; J, Hz) of compounds XXV - XXIX

Proton JH,H Proton J H,H Zlúčenina Compound XXIX XXIX XXV XXV XXVI XXVI XXVII XXVII XXVIII XXVIII H-3 H-3 6,64dd 6.64dd 6,65dd 6.65dd 7,Old 7,Old 7,00d 7.00d 7,00d 7.00d H-4 H-4 6,43dd 6.43dd 6,45dd 6.45dd 7,49d 7.49d 7,47d 7.47d 7,48d 7.48d H-5. H-5. 7,41dd 7.41dd 7,46dd 7.46dd - - - - - - H-6 H-6 7,44d 7.44d 7,40d 7.40d 7,48d 7.48d 7,47d 7.47d 7,47 7.47 H-7 H-7 5,99d 5.99d 5,87d 5.87d 6,24d 6.24d 6,26d 6.26d 6,27 6.27 H arom H aroma 7,22bs 7.22bs 7,10-7,30 7.10-7.30 7,25bs 7.25bs 7,10-7,30 7.10-7.30 7,20-7,40 7.20-7.40 CH-CH3 CH-CH 3 4,52q 4.52q 4,54q 4.54q 4,53q 4.53q 4,56q 4.56q 4,53q 4.53q 4,18q 4.18q 4,50q 4.50q COOCH3 COOCH 3 3,70s 3.70s 3,71s 3.71s 3,78s 3.78s 3,72s 3.72s 3,72s 3.72s CH3-CH CH3 - CH l,05d 1.05d l,04d 1.04d l,05d 1.05d l,06d 1.06d l,00d 1.00d l,00d 1.00d l,03d 1.03d R1 R 1 2,42s 2.42s 2,41s 2.41s 2,41s 2.41s 2,41s 2.41s 2,50q 2.50q 2,12s 2.12s 2,13s 2.13s l,17t 1.17t R2 R2 2,15s 2.15s 2,91-2,52 2.91-2.52 2,16s 2.16s 2,92-2,52 2.92-2.52 2,91q 2.91q 1,19;1,15 1.19;1.15 l,20;l,17 1.20;1.17 l,20t 1.20t J3,4 J 3.4 3,2 3.2 3,2 3.2 3,9 3.9 3,9 3.9 3,9 3.9 J6,7 J 6.7 15,2 15.2 15,2 15.2 15,4 15.4 15,4 15.4 15,5 15.5

a Merané v hexadeuteroacetóne a Measured in hexadeuteroacetone

Antifungálna aktivita zlúčenín podia vynálezu bola testovaná štardardnou difúznou metodou na agarových platniach (0 100 mm) na spory húb: Alternariaalternata, Fusarium nivale, Botrytis cinerea a Phytophtora infestans. Očinok sa prejayil vytvořenímsterilnej inhibičnej zóny (0 v mm), v kontrole nebola vytvořená žiadna zóna. Použitá končentrácia skúmaných látok 1 % acetonový roztok, tj. 100 ug účinnej látky na misku.The antifungal activity of the compounds according to the invention was tested by the standard diffusion method on agar plates (0 100 mm) for fungal spores: Alternaria alternata, Fusarium nivale, Botrytis cinerea and Phytophtora infestans. The effect was demonstrated by the formation of a sterile inhibition zone (0 in mm), in the control no zone was formed. The concentration of the investigated substances used was 1% acetone solution, i.e. 100 μg of active substance per plate.

TABULKA 11TABLE 11

Výsledky testov fungicídnej účinnosti zlúčenín I - XXIXTest results of fungicidal efficacy of compounds I - XXIX

Zlúčenina Compound 0 = Priemer zóny mm 0 0 = Zone diameter mm 0 Alternaria alternate Alternaria alternata Fusarium nivale Fusarium nivale Botrytis cinerea Botrytis cinerea Phytophtora infestans Phytophthora infestans I I 44 44 II II 48 48 III III 52 52 IV IV 46 46 58 58 6060 v in 42 42 . 48 . 48 48 48 58 58 VI VI 46 46 50 50 60 60 VII VII 44 44 VIII VIII 50 50 IX IX 58 58 X X 60 60 XI XI 46 46 XII XII 56 56 XIII XIII 50 50 XIV XIV 52 52 XV XV 58 58 XVI XVI 60 60 XVII XVII 58 58 XVIII XVIII 42 42 58 58 XIX XIX 60 60 XX XX 54 54 XXI XXI 58 : 58 : XXII XXII 56 56 52 52 XXIII XXIII 58 58 48 48 XXIV XXIV 54 54 50 50 40 40 XXV XXV 42 42 XXVI XXVI 48 48 XXVII XXVII 52 52 XXVIII XXVIII 56 56 XXIX XXIX 58 58

Claims (2)

CS 276621 B6 14 PATENTOVÉ NÁROKY 1. N-substituované-2,6-dialkylanilidy vzorca I co kde R3 je metyl, etyl2 R je metyl, etyl R3 je H, 2-furfuryl, 5-(3,4-dichlórfenyl)-2-furfuryl, l-hydroxy-2-propyl, 1-metoxy--2-propyl, 1-metoxýkarbonyl-l-etyl R4 je chlóracetyl, 3-(2-furyl)propenoyl, 3-(5-nitro-2-furyl)propenoyl, benzoyl.CLAIMS 1. N-substituted-2,6-dialkylanilides of formula I wherein R3 is methyl, ethyl2R is methyl, ethyl R3 is H, 2-furfuryl, 5- (3,4-dichlorophenyl) -2 -furfuryl, 1-hydroxy-2-propyl, 1-methoxy-2-propyl, 1-methoxycarbonyl-1-ethyl R4 is chloroacetyl, 3- (2-furyl) propenoyl, 3- (5-nitro-2-furyl) propenoyl, benzoyl. 2. SpAosob přípravy N-substituovaných-2,6-dialkylanilidov podlá bodu 1, vyznačený tým,že sa posobí na N-substitovaný 2,6-dialkylanilín vzorca II SJNH R1 Rr (II) 12 3 kde R , R a R máju uvedený význam,arylchloridom vzorca III R4-C1 (III), 4 kde R má horeuvedený význam, v nepolárnom rozpúštadle například v benzéne alebo toluéne v přítomnosti uhličitanu sod-ného pri teplotách 25 až 60 *Č.2. A process for the preparation of N-substituted-2,6-dialkylanilides according to claim 1, characterized in that it is N-substituted 2,6-dialkylaniline of formula II SJNH R1 Rr (II) 12 3 wherein R, R and R are as defined above is an aryl chloride of formula III R4-C1 (III) 4 wherein R is as defined above, in a non-polar solvent such as benzene or toluene in the presence of sodium carbonate at temperatures of 25-60 ° C.
CS888650A 1988-12-22 1988-12-22 N-substituted-2,6-dialkylanilides and methods for their preparation CS276621B6 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10016418B2 (en) * 2010-11-05 2018-07-10 Seaomyx, Inc. Compounds useful as modulators of TRPM8

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10016418B2 (en) * 2010-11-05 2018-07-10 Seaomyx, Inc. Compounds useful as modulators of TRPM8
US10953007B2 (en) 2010-11-05 2021-03-23 Firmenich Incorporated Compounds useful as modulators of TRPM8

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