CS248919B1 - 3,4-Dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones and their preparation - Google Patents
3,4-Dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones and their preparation Download PDFInfo
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- CS248919B1 CS248919B1 CS848714A CS871484A CS248919B1 CS 248919 B1 CS248919 B1 CS 248919B1 CS 848714 A CS848714 A CS 848714A CS 871484 A CS871484 A CS 871484A CS 248919 B1 CS248919 B1 CS 248919B1
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Abstract
Vynález sa týká odboru organickej syntézy i rieši přípravu nových zlúcenín 3,4-dichlór-5-/5-aryl-2-furoyl/oxy-2/5H/-furanónov s fungicídnym účinkom. Podstata spósobu přípravy podlá vynálezu spočiva v tom, že sa pósobí chloridom alebo zmiešaným anhydridom kyseliny 5-aryl-2- -furánkarboxylovej na kyselinu mukochiórovú v benzene alebo toluéne pro teplotách 60 až 80 °C. 3,4-dichlór-5-/5-aryl-2-furoyl/oxy-2- /5H/furanóny sú charakterizované vzorcom Cl Cl o X kde X je 2-NO , 2-C1, 3-MO2, 3-CF3The invention relates to the field of organic synthesis and solves the preparation of new compounds of 3,4-dichloro-5-[5-aryl-2-furoyl/oxy-2/5H]-furanones with a fungicidal effect. The essence of the method of preparation according to the invention lies in the fact that the chloride or mixed anhydride of 5-aryl-2-furancarboxylic acid is treated with mucochioric acid in benzene or toluene at temperatures of 60 to 80 °C. 3,4-dichloro-5-/5-aryl-2-furoyl/oxy-2-/5H/furanones are characterized by the formula Cl Cl o X where X is 2-NO, 2-C1, 3-MO2, 3-CF3
Description
243919 2243919 2
Vynález sa týká 3,4-dichlór-5-/5-aryl-2-furoyl/oxy-2/5H/turanónov a spósobu ich přípra-vy. Vhodnou metodou na leh přípravu je reakcia chloridov alebo zmiešaných anhydridov 5-aryl--2-furánkarboxylových kyselin s kyselinou mukochlórovou.The invention relates to 3,4-dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / turanones and to a process for their preparation. A suitable method for preparing is the reaction of chlorides or mixed 5-aryl-2-furanecarboxylic acid anhydrides with mucochloric acid.
Je známe /čsl. pat. 166140 /19/6//, že 5-aryloxy-3,4-disubstituované 2/5H/furanóny majúdobré fungicídne vlastnosti vhodné najma na potláčanie rastu fytopatogenných húb ako Fusariumnievale, Tilletia tritici, Sclerotinia fructicola, Botrysis cineres.It is known / Czechoslovak. pat. 166140/19/6, that 5-aryloxy-3,4-disubstituted 2 / 5H / furanones possess good fungicidal properties particularly useful for controlling the growth of phytopathogenic fungi such as Fusariumnievale, Tilletia tritici, Sclerotinia fructicola, Botrysis cineres.
Uvedené zlúčeniny /J. Amer. Chern. Soc. 72, 2536 /1950/, US pat. 2786 798 /1957// móžuslúžit ako moridlo semien najma na ochranu raze proti fuzarióze a pšenice proti mazlavejsneti pšeničnej. Čs.patentom /čsl. patent 148592 /1973// je chráněný sposob přípravy acetyle-nických pseudoesterov 3,4-dihalogén-5/211/f uranonov a ich fungicídna účinnost predovšetkýmproti fytopatogenným hubám.Said Compounds / J. Amer. Chern. Soc. 72, 2536 (1950), U.S. Pat. 2786 798/1957 // can be used as a seed dressing especially to protect against the fusariosis and wheat against the common wheat. Čs.patentom / čsl. No. 148592 (1973) is a process for the preparation of acetylene pseudoesters of 3,4-dihalogen-5/211 / uranones and their fungicidal activity, in particular against phytopathogenic fungi.
Ako sa uvádza v dalších patentoch /čsl. patenty: 138821 /19/0/ 149048 /1973/, 170448'/1977// sa ďalšie pseudoestery kyseliny mukochlórovej hodia na potieranie fytopatogennýchhúb.As disclosed in other patents / art. Patents: 138821/19/0/149048 (1973), 170448 '(1977), other pseudoesters of mucochloric acid are useful for controlling phytopathogenic fungi.
Studium litératúry ukázalo, že 3,4-dichlór-5-/5-aryi-2-furoyi/-oxy-2/5H/furanóny nebolidoteraz připravené.The study of the literature showed that 3,4-dichloro-5- [5-aryl-2-furoyl-oxy-2 / 5H] furanones were not prepared.
Predmetom vynálezu sú 3,4-dichlór-5/5-aryi-2-furoyi/oxy-2/5H/furanóny vzorca jg/-ÍQLcoo -Ϊξί o /1/ kde X je 2-C1, 3-NO^, 3-CF^ a sposob ich přípravyThe present invention relates to 3,4-dichloro-5/5-aryl-2-furoyloxy-2 / 5H / furanones of formula (II) wherein X is 2-C1, 3-NO3, 3 -CF 2 and methods for their preparation
Podstata spósobu přípravy 3,4-dichlór-5-/5-aryl-2-furoyl/oxy-2/5H/furanonov spočíváv tom, že chloridom 5-aryl-2-furánkarboxylovej kyseliny vzorca II /11/The principle of the preparation of 3,4-dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones is that the 5-aryl-2-furanecarboxylic acid chloride of formula II / 11 /
XX
alebo zmiešaným anhydridom vzorca III COOCCF3or a mixed anhydride of formula III COOCCF 3
X /111/ kde X má horeuvedený význam, pósobí na kyselinu mukochlórovú v benzéne alebo toluéne pri teplotách 60 až 80 °C. Výhody spósobu přípravy .zlúčenín I podlá vynálezu spočívajú okrem iného v tom, že sareakcia cnloridov alebo zmiešaných anhydridov 5-aryl-2-furánkarboxylových kyselin s 3,4--dichlór~2/5H/furanónom uskutočňuje v jednom stupni v nenáročných podmienkách s dobrýmvýťažkom, pričom sa získajú zlúčeniny I.X (III) wherein X is as defined above, acts on mucochloric acid in benzene or toluene at temperatures of 60 to 80 ° C. The advantages of the process for the preparation of the compounds I according to the invention are, inter alia, that the reaction of the chlorides or mixed 5-aryl-2-furanecarboxylic acid anhydrides with 3,4-dichloro-2 / 5H / furanone is carried out in one step in low yield conditions with good yield to yield compounds I.
Wasledovné příklady ilustrujú, ale neobmedzujú nové látky a sposob ich přípravy. 3 248919 Příklad 1 3,4-dichlór-5^5-/3-nitrofenyl/-2-furoyloxyJ -2/5H/furanón 3,4-dichlór-5-hydroxy-2-furanón /kys. mukochlórová/ /2,1 g/ v benzene /15 ml7 a chloridkyseliny 5-/3-nitrofenyl pyrosiizovej sa zahrieva pri teplote varu /dokial uniká plynnýHC1/. Po skončení reakcie. sa reakčná zmes ochladí a vykrystalizovaný produkt sa prekryšta-lizuje /z benzenu alebo zmesi etanol-voda/. Příklad 2 3, 4-dichlór-5-Jj5-/3-trif luórmetyl/-2-f uroyloxyj -2/5H/furanón /IV/ 3,4-dichlór-5-hydroxy-2-furanón /kys. mukochlórová/ /2,1 g/ v toluene /10 ml/ a zmiešanýanhydrid kyseliny trifenoioctovej a 5-/3-trifiuormětylfenyl/ pyrosiizovej sa mieša pri la-boratornej teplote 2 h. Po skončení reakcie sa rozpúštadlo vákuove oddestiluje a reakčnýprodukt sa prekryštalizuje /z metanolu/.The following examples illustrate, but do not limit, the novel substances and the methods for their preparation. Example 1 3,4-Dichloro-5- [5- (3-nitrophenyl) -2-furoyloxy] -2 / 5H / furanone 3,4-dichloro-5-hydroxy-2-furanone / acid. mucochloric acid (2.1 g) in benzene (15 ml 7 and 5- [3-nitrophenyl pyrosic acid chloride) is heated at boiling point / until gaseous HCl is removed. After the reaction is complete. the reaction mixture is cooled and the crystallized product is recrystallized (from benzene or ethanol-water). Example 2 3,4-Dichloro-5-η 5 - (3-trifluoromethyl) -2-uroyloxy-2 (5H) furanone (IV) 3,4-dichloro-5-hydroxy-2-furanone / acid. mucochloric acid (2.1 g) in toluene (10 ml) and mixed triphenoxyacetic anhydride and 5- (3-trifluoromethylphenyl) pyrosulphate are stirred at room temperature for 2 hours. After the reaction is complete, the solvent is distilled off under vacuum and the reaction product is recrystallized ( methanol /.
Podobné sa syntetizovali zldčeniny I a II. Výtažky, t. t., výsledky elementárnej ana-lýzy a hodnoty 1H UMR spektier sú uvedené v tabulkách I a II.Similarly, compounds I and II were synthesized. Extracts, i.e., elemental analysis results and 1H UMR spectra are shown in Tables I and II.
Spektrálné meranie NI-1R spektra boli namerané na 80 MHz spektrofotometri MS 487 C Tesla v hexadeutero-acetone za použitia tetrametylsilná ako vnútorného standardu Chemické posuny sa udávajúv ppm.Spectral measurements of the NI-1R spectrum were measured on an 80 MHz MS 487 C Tesla spectrophotometer in hexadeutero-acetone using tetramethylsilane as internal standard Chemical shifts are reported in ppm.
Tabulka ITable I
Cl ClCl Cl
Zlúč. číslo X Sumárny vzorec MH Vypočítané/nájdené T. t. °C/výtazok/ »c %H %C1 I 2-WOn C, rH_CloUC) 48,94 1,92 19,26 3,80 160 až 162 2 15 7 2 6 /368,1/ 4tí , 92 1,90 19,20 3,62 /75/ II 2-C1 c1^h7ci?oj 50,38 1,97 '29,74 94 až 95 /357,6/ 50,30 1,90 29,72 /70/ III 3-NO2 C, cH_ClnWO>. 48,94 1,92 19,26 3,o0 182 až 183 /368,1/ 48,78 1,90 19,08 3 , / 8 /74/ XV 3-CF3 C16H7F3C12°4 49 , 13 1,80 18 , 12 139 až 141 49,10 1,82 18,04 /80/Bile. No. X Summary Formula MH Calculated / Found T.t ° C / Extract / c% H% C1 I 2-WOn C, rH_CloUC) 48.94 1.92 19.26 3.80 160 to 162 2 15 7 2 6 / 368,1 / 4th, 92 1,90 19,20 3,62 / 75 / II 2-C1 c1 ^ h7i oj 50,38 1,97 '29, 74 94 to 95 / 357,6 / 50, 30 1.90 29.72 / 70 / III 3-NO2 C, cH_ClnWO>. 48.94 1.92 19.26 3, 0 182 to 183 / 368.1 / 48.78 1.90 19.08 3, / 8/74 / XV 3-CF3 C16H7F3C12 ° 4 49, 13 1.80 18 , 12 139-141 49.10 1.82 18.04 / 80 /
Claims (2)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS848714A CS248919B1 (en) | 1984-11-15 | 1984-11-15 | 3,4-Dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones and their preparation |
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| CS848714A CS248919B1 (en) | 1984-11-15 | 1984-11-15 | 3,4-Dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones and their preparation |
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| Publication Number | Publication Date |
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| CS871484A1 CS871484A1 (en) | 1985-10-16 |
| CS248919B1 true CS248919B1 (en) | 1987-03-12 |
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| CS848714A CS248919B1 (en) | 1984-11-15 | 1984-11-15 | 3,4-Dichloro-5- (5-aryl-2-furoyl) oxy-2 / 5H / furanones and their preparation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327059A (en) * | 2014-10-15 | 2015-02-04 | 暨南大学 | Furanone derivative and preparation method and purpose |
| CN106008496A (en) * | 2016-05-31 | 2016-10-12 | 华南农业大学 | S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof |
-
1984
- 1984-11-15 CS CS848714A patent/CS248919B1/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327059A (en) * | 2014-10-15 | 2015-02-04 | 暨南大学 | Furanone derivative and preparation method and purpose |
| CN106008496A (en) * | 2016-05-31 | 2016-10-12 | 华南农业大学 | S-(5-substituted-1, 3, 4-thiadiazole)-(5-substituted phenyl)-2-furancarbothioic acid ester compound, preparation method and application thereof |
| CN106008496B (en) * | 2016-05-31 | 2018-06-19 | 华南农业大学 | S- (5- substitution -1,3,4- thiadiazoles)-(5- substituted-phenyls) -2- furans bamic acid esters compounds and its preparation method and application |
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| Publication number | Publication date |
|---|---|
| CS871484A1 (en) | 1985-10-16 |
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