DE2459666B2 - DINITRO 2,2'-BITHIOPHENE DERIVATIVES AND AGENTS CONTAINING THEM - Google Patents
DINITRO 2,2'-BITHIOPHENE DERIVATIVES AND AGENTS CONTAINING THEMInfo
- Publication number
- DE2459666B2 DE2459666B2 DE19742459666 DE2459666A DE2459666B2 DE 2459666 B2 DE2459666 B2 DE 2459666B2 DE 19742459666 DE19742459666 DE 19742459666 DE 2459666 A DE2459666 A DE 2459666A DE 2459666 B2 DE2459666 B2 DE 2459666B2
- Authority
- DE
- Germany
- Prior art keywords
- dinitro
- bithiophene
- weight
- agents containing
- derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- OHSJVMQOCWORDQ-UHFFFAOYSA-N 3,4-dinitro-2-thiophen-2-ylthiophene Chemical class [O-][N+](=O)C1=CSC(C=2SC=CC=2)=C1[N+]([O-])=O OHSJVMQOCWORDQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CTJKNUMZOUGBDA-UHFFFAOYSA-N 1-[5-(3,5-dinitrothiophen-2-yl)thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)S1 CTJKNUMZOUGBDA-UHFFFAOYSA-N 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFUGFVOOCPLZSP-UHFFFAOYSA-N 5-(3,5-dinitrothiophen-2-yl)thiophene-2-carbaldehyde Chemical compound S1C([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=CC=C(C=O)S1 LFUGFVOOCPLZSP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- GKGAOTYPISAEEK-UHFFFAOYSA-N 1-(5-thiophen-2-ylthiophen-2-yl)ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=CC=CS1 GKGAOTYPISAEEK-UHFFFAOYSA-N 0.000 description 1
- RCJUMGGYFRTUPZ-UHFFFAOYSA-N 3,4-dinitro-2-thiophen-2-ylthiophene;propan-2-one Chemical class CC(C)=O.[O-][N+](=O)C1=CSC(C=2SC=CC=2)=C1[N+]([O-])=O RCJUMGGYFRTUPZ-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- AHNXQTIZPFQOKU-UHFFFAOYSA-N 5-(5-nitrothiophen-2-yl)thiophene-2-carbaldehyde Chemical compound S1C([N+](=O)[O-])=CC=C1C1=CC=C(C=O)S1 AHNXQTIZPFQOKU-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
thiophen-penvate, ^ Kondensation von Dinitro. η mit Aminoverbindungen ge-thiophene penvate, ^ condensation of dinitro . η with amino compounds
erfinZngsgemäßen Verbindungen sind wirk enr°Tl!:£a sie besitzen selektive antimykouptsächlich gegen Dennatomy-erfinZngsgemäßen connections are more s r ° Tl: £ possess a selective antimykouptsächlich against Dennatomy-
.· T-_:-.v.^«V.«tip Mikrosnorie.. · T -_: -. V. ^ «V.« tip Mikrosnorie.
-CHO -COCH3 -CHO -COCH 3
oderor
Antimy-Antimy
-CH=N-^ V-CH = N- ^ V
2. Antimykotisch wirkendes Mittel, dadurch 25 ü gekennzeichnet, daß es aus einer Verbindung ist nach Anspruch 1 als Wirkstoff und üblichen Trägerstoffen besteht.2. Antifungal agent, thereby 25 u characterized in that it is composed of a compound according to claim 1 as an active ingredient and usual Carriers consists.
B e i s ρ ιB e i s ρ ι
NJ E,ge„-in und Undecytaisaute . v«rhäl,„ismaßig geringNJ E, ge "-in and Undecytaisaute. v "rh AEL" is m Assig low
el 1el 1
Es war bereits bekannt, daß bestimmte Bis- oder Tristhiophene wirksame Mittel zur Bekämpfung von Nematoden sind. Derartige Verbindungen wurden daher bereits für landwirtschaftliche Zwecke eingesetzt (FR-PS 1207036).It was already known that certain bis- or tristhiophene effective agents for combating Are nematodes. Such compounds have therefore already been used for agricultural purposes (FR-PS 1207036).
Es hat sich nun gezeigt, daß bestimmte Dinitrobisthiophen-Derivate selektive antimykotische Aktivität besitzen.It has now been shown that certain dinitrobisthiophene derivatives have selective antifungal activity.
Gegenstand der Erfindung sind Dinitro-2,2'-bi-The invention relates to dinitro-2,2'-bi-
thiophen-Derivate der Formelthiophene derivatives of the formula
worin R1 = NO2, R2 = H bzw. R1 = H, R2 = Nitro und R3 jeweilswherein R 1 = NO 2 , R 2 = H and R 1 = H, R 2 = nitro and R 3, respectively
30 141,6 g 5-Acetyl-2,2'-bithiophen löst man bei einer 30 141.6 g of 5-acetyl-2,2'-bithiophene are dissolved in a
Temperatur von O0C bis -5°C in 1416ml konzentrierter Schwefelsäure (spezifisches Gewicht 1,84), kühlt auf eine Temperatur von -100C ab, tropft ein auf eine Temperatur von — 100C gekühltes Nitriergemisch, bestehend aus 62,8 ml konzentrierter Salpetersäure (spezifisches Gewicht 1,51) und 125,7 ml konzentrierter Schwefelsäure (spezifisches Gewicht 1,84), zu. Die Reaktionsmasse hält man in dem Kühlbad 30 Minuten. Danach gießt man sie unter Rühren langsam auf Eis, filtriert den Niederschlag, wäscht bis zur neutralen Reaktion mit Wasser und trocknet.Temperature of from 0 ° C to -5 ° C in 1416ml concentrated sulfuric acid (specific gravity 1.84), cooled to a temperature of -10 0 C, a dropped to a temperature of - 10 0 C chilled nitrating mixture, consisting of 62, 8 ml of concentrated nitric acid (specific gravity 1.51) and 125.7 ml of concentrated sulfuric acid (specific gravity 1.84), too. The reaction mass is kept in the cooling bath for 30 minutes. It is then slowly poured onto ice with stirring, the precipitate is filtered off, washed with water until it reacts neutral and dried.
Das Nitrierprodukt kristallisiert man aus Dioxan unter Zugabe von Aktivkohle um (für 20 g Produkt werden 100 ml Dioxan verbraucht). Nach dem Abdestillieren des überschüssigen Dioxans erhält man eine erste Fraktion (Ausbeute 30 Gew.-%) als gelbgefärbte Kristalle vom Schmelzpunkt 121 bis 122° C. Nach einer nochmaligen Umkristallisation zunächst aus Dioxan und dann aus Heptan erhält man 100 g reines 5',3' - Dinitro - 5 - azetyl - 2,2' - bithiophen vom Schmelzpunkt 122 bis 122,5 (Ausbeute 75 bis 80 Gew.-%).The nitration product is recrystallized from dioxane with the addition of activated charcoal (for 20 g of product 100 ml of dioxane are consumed). After the excess dioxane has been distilled off, one obtains a first fraction (yield 30% by weight) as yellow-colored crystals with a melting point of 121 to 122 ° C. After another recrystallization, first from dioxane and then from heptane, 100 g are obtained pure 5 ', 3' - dinitro - 5 - acetyl - 2,2 '- bithiophene of melting point 122 to 122.5 (yield 75 to 80% by weight).
NMR-Spektrum: f> H4 7,94 Mio"1, f> H4 8,41 Mio"1, ^H3 7,73MiO"1, Λ CH3 2,78 Mio"1, σ 3,4 = (τ4',3' = 5Hz.Nuclear Magnetic Resonance Spectrum: f> H 4 7.94 million " 1 , f> H 4 8.41 million" 1 , ^ H 3 7.73Mio "1 , Λ CH 3 2.78 million" 1 , σ 3.4 = ( τ4 ', 3' = 5Hz.
-CHO-CHO
-COCH3 -COCH 3
C10H6N2O5S2
Berechnet
gefunden .C 10 H 6 N 2 O 5 S 2
Calculated
found .
(in Gew.-%):(in% by weight):
.. C 40,26; H 2,02; N 9,38;.. C 40.26; H 2.02; N 9.38;
.. C 40,21; H 2,18; N 9,28... C 40.21; H 2.18; N 9.28.
Aus der Mutterlauge erhält man außerdem eine zweite Fraktion von Kristallen vom SchmelzpunktA second fraction of crystals with a melting point is also obtained from the mother liquor
ist. bis 1040C und dann eine dritte Fraktion von Kri-is. to 104 0 C and then a third fraction of crime
Die Erfindung betrifft weiterhin ein antimykotisch f>5 stallen vom Schmelzpunkt 84 bis 96° C. Die zweite wirkendes Mittel, das aus einer Verbindung der oben- und die dritte Fraktion (die Gesamtausbeute beträgt genannten Formel als Wirkstofl und einem üblichen 45 bis 50 Gew.-%) stellen jeweils ein Gemisch von τ™wprstoff besteht. zwei Isomeren von Dinitrobithiophenmethylketon,The invention also relates to an antifungal f> 5 stalls with a melting point of 84 to 96 ° C. The second acting agent obtained from a compound of the above and the third fraction (the total yield is mentioned formula as active ingredient and a customary 45 to 50 wt .-%) each represent a mixture of τ ™ wprstoff consists. two isomers of dinitrobithiophene methyl ketone,
und zwar 5',3'-Dinitro-5-azetyl-2,2'-bithiophennamely 5 ', 3'-dinitro-5-acetyl-2,2'-bithiophene
und 5',3'-Dinitro-5-azetyl-2.2'-bithiophen
NO2 0 and 5 ', 3'-dinitro-5-acetyl-2.2'-bithiophene
NO 2 0
Man erhält 100 g Endprodukt (43 Gew.-%), das ein Gemisch von zwei Isomeren, und zwar 5',3'-Dinitro-5-formyl-2,2'-bithiophen 100 g of end product (43% by weight) are obtained, which is a mixture of two isomers, namely 5 ', 3'-dinitro-5-formyl-2,2'-bithiophene
NO2 NO 2
O2N-/ Vf VcO 2 N- / Vf Vc
und 5',3'-Dinitro-5-formyl-2,2'-bithiophenand 5 ', 3'-dinitro-5-formyl-2,2'-bithiophene
NO2 NO 2
dar. Dabei beträgt das Verhältnis der genannten Isomere in der zweiten Fraktion nach den Angaben des NMR-Spektrums 86,5 Gew.-% : 13,5 Gew.-% und in der dritten 51 Gew.-% : 49 Gew.-%.The ratio of the isomers mentioned in the second fraction, according to the data from the NMR spectrum, is 86.5% by weight: 13.5 % by weight and in the third 51% by weight: 49% by weight .
Die Trennung der genannten Isomere wird durch nochmalige Umkristallisation aus dem Isopropylalkohol vorgenommen.The isomers mentioned are separated by repeated recrystallization from the isopropyl alcohol performed.
In diesem Falle fallt bei langsamer Abkühlung der Lösung zunächst das 5',3'-Dinitro-5-azetyl-2,2'-bithiophen aus. Entsprechend erhält man im weiteren aus der Mutterlauge eine gewisse Menge des zweiten Isomers, des 5',3'-Dinitro-5-azetyl-2,2'-bithiophens, vom Schmelzpunkt 136 bis 136,5° C mit einer Absorption im UV-Bereich des Spektrums bei l'max = 280 nm - f'max = 10210 und bei A"mox = 376 ntn - rmax = HOlO, mit einer Absorption im IR-Bereich des Spektrums mit ν cm"1; 1663, 1520, 1412, 1365, 1332. 1296, 1262, 1150, 1040, 860, 802, 775, 745, 723.In this case, when the solution is slowly cooled, the 5 ', 3'-dinitro-5-acetyl-2,2'-bithiophene initially precipitates. Correspondingly, a certain amount of the second isomer, the 5 ', 3'-dinitro-5-acetyl-2,2'-bithiophene, with a melting point of 136 to 136.5 ° C. with an absorption in the UV is obtained from the mother liquor. Range of the spectrum at l ' max = 280 nm - f' max = 10210 and at A " mox = 376 ntn - r max = HO10, with an absorption in the IR range of the spectrum with ν cm"1; 1663, 1520, 1412, 1365, 1332, 1296, 1262, 1150, 1040, 860, 802, 775, 745, 723.
NMR-Spektrum: ό H4 = 8,03 Mio"1, ^H4 =•8,48 Mio"1, OH3 7,62Mi0 -1, <i CH3 2,81 Mio"1, „ 3',4' = σ 4',3' = 5 Hz.NMR spectrum: ό H 4 = 8.03 million " 1 , ^ H 4 = • 8.48 million" 1 , OH 3 7.62Mi 0 -1 , <i CH 3 2.81 million " 1 , " 3 ' , 4 '= σ 4', 3 '= 5 Hz.
Ci0H6N2O5S2 (in Gew.-%):Ci 0 H 6 N 2 O 5 S 2 (in% by weight):
Berechnet ... C 40,26; H 2,02, N 9,38;
gefunden .... C 40,40, H 2,12, N 9,40.Calculated ... C 40.26; H 2.02, N 9.38;
found .... C 40.40, H 2.12, N 9.40.
158,4 g 5'-Nitro-5-formyl-2,2'-bithiophen löst man in 1584 ml konzentrierter Schwefelsäure (spezifisches Gewicht 1,84) bei einer Temperatur von 0°C. Der erhaltenen Lösung tropft man ein Nitriergemisch, bestehend aus 60,4 ml konzentrierter Salpetersäure (spezifisches Gewicht 1,348) und 148,5 ml konzentrierter Schwefelsäure (spezifisches Gewicht 1,84), zu, indem man die Temperatur in einem Bereich von 0°C bis -3° C hält. Die Reaktionsmasse hält man noch 30 Minuten in dem Kühlbad, gießt auf Eis, filtriert den Niederschlag ab, wäscht bis zur neutralen Reaktion mit Wasser und trocknet ihn.158.4 g of 5'-nitro-5-formyl-2,2'-bithiophene are dissolved in 1584 ml of concentrated sulfuric acid (specific weight 1.84) at a temperature of 0.degree. A nitration mixture consisting of 60.4 ml of concentrated nitric acid (specific gravity 1.348) and 148.5 ml of concentrated sulfuric acid (specific gravity 1.84) is added dropwise to the resulting solution by keeping the temperature in a range from 0 ° C. to -3 ° C. The reaction mass is kept in the cooling bath for a further 30 minutes, poured onto ice, the precipitate is filtered off, washed with water until it reacts neutral and dried.
Das Nitrierprodukt wird aus einem Gemisch, welches aus 1 Teil Benzol und aus 2 Teilen Hexan bestellt, unter Zugabe von Aktivkohle umkristallisierl.The nitration product is made from a mixture consisting of 1 part of benzene and 2 parts of hexane, recrystallized with the addition of activated charcoal.
O2NO 2 N
darstellt.represents.
Die Trennung der genannten Isomere wird durch Umkristallisationen aus Isopropylalkohol durchgerührt. The isomers mentioned are separated by recrystallizations from isopropyl alcohol.
C9H4N2O5S2 (in Gew.-%):C 9 H 4 N 2 O 5 S 2 (in% by weight):
Berechnet ... C 38,02, H 1,41, N 9,85.
gefunden .... C 38,14, H 1,38, N 9,97.Calculated ... C 38.02, H 1.41, N 9.85.
found .... C 38.14, H 1.38, N 9.97.
120 g 5\3'-Dinitro-5-formyl-2,2'-bithiophen löst man unter Erhitzen in 600 ml trockenem Benzol auf, gibt 60 g Metaaminobenzoesäure, ebenfalls vorher in 6000 ml trockenem Benzol gelöst, zu. Das Reaktionsgemisch erhitzt man 2 Stunden auf dem siedenden Wasserbad, destilliert das überschüssige Lösungsmittel ab, filtriert den Niederschlag unter Kühlen ab und kristallisiert aus Alkohol um.120 g of 5 \ 3'-dinitro-5-formyl-2,2'-bithiophene are dissolved in 600 ml of dry benzene with heating, add 60 g metaaminobenzoic acid, also previously dissolved in 6000 ml dry benzene. The reaction mixture If the mixture is heated on a boiling water bath for 2 hours, the excess solvent is distilled off off, the precipitate is filtered off with cooling and recrystallized from alcohol.
Man erhält )00g N-(5',3'-Dinitro-2,2'-bithienyliden-5)-metadmirobenzoesäure der Formel00 g of N- (5 ', 3'-dinitro-2,2'-bithienylidene-5) -metadmirobenzoic acid are obtained the formula
NO2 NO 2
die ein kristallines, rotorangefarbenes, in Alkohol, Lanolin und Rizinusöl wenig lösliches, in Dimethylformamid und Dimethylsulfoxid lösliches Pulver vom Schmelzpunkt 195° C darstellt, das sich bei Lichteinwirkung verändert, ist.which is a crystalline, red-orange colored, poorly soluble in alcohol, lanolin and castor oil, in dimethylformamide and dimethyl sulfoxide is a soluble powder with a melting point of 195 ° C, which is formed when exposed to light changed, is.
C16H9N3O6S2 (in Gew.-%):
Berechnet ... N 10,41;
gefunden N 10,56.C 16 H 9 N 3 O 6 S 2 (in% by weight):
Calculated ... N 10.41;
found N 10.56.
IR-Spektrum: cm"
1-NO2 1520, 1335.IR spectrum: cm "
1-NO 2 1520, 1335.
■C=O 1685; rC = N 1614;■ C = O 1685; r C = N 1614;
Claims (1)
1. Dinitro-2^'-bithiophen-Derivate der FormelPatent claims:
1. Dinitro-2 ^ '- bithiophene derivatives of the formula
Xh bekannter Weise durch N.tnerung der ent-Compounds according to the invention can never be used in
As is known, by increasing the
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1977301 | 1973-12-27 | ||
| SU7301977301A SU577207A1 (en) | 1973-12-27 | 1973-12-27 | Antifungal-and antibacterial-active substance |
| SU2005054 | 1974-03-26 | ||
| SU2005053 | 1974-03-26 | ||
| SU7402005054A SU477625A1 (en) | 1974-03-26 | 1974-03-26 | 5-acetyl-5',3'-dinitro-2,2'-bithiophene having anti-fungi action |
| SU7402005053A SU477624A1 (en) | 1974-03-26 | 1974-03-26 | 5'3'-dinitro-2,2'-dithienilidene-5-n-3-carboxyphenyl,having anti-fungi action |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2459666A1 DE2459666A1 (en) | 1975-07-10 |
| DE2459666B2 true DE2459666B2 (en) | 1977-05-26 |
| DE2459666C3 DE2459666C3 (en) | 1978-01-05 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| DE2459666A1 (en) | 1975-07-10 |
| FR2255896A1 (en) | 1975-07-25 |
| GB1478400A (en) | 1977-06-29 |
| FR2255896B1 (en) | 1978-11-24 |
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