DE1492287C - Antimicrobial agents - Google Patents
Antimicrobial agentsInfo
- Publication number
- DE1492287C DE1492287C DE1492287C DE 1492287 C DE1492287 C DE 1492287C DE 1492287 C DE1492287 C DE 1492287C
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- parts
- triphenyltin
- antimicrobial agents
- pyridyl
- 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.)
- Expired
Links
- 239000004599 antimicrobial Substances 0.000 title claims description 6
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000003568 thioethers Chemical class 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 244000052616 bacterial pathogens Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 229940095731 Candida albicans Drugs 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 241000901842 Escherichia coli W Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229940076185 Staphylococcus aureus Drugs 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M Triphenyltin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- CXDBXTHJTZQPOJ-UHFFFAOYSA-M [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 Chemical compound [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 CXDBXTHJTZQPOJ-UHFFFAOYSA-M 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2R)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
Die Erfindung betrifft ein antimikrobielles Mittel, das gekennzeichnet ist durch einen Gehalt an Triphenylzinn-[pyridyl-N-oxid-(2)]-sulfid. Dieses besitzt vermutlich die FormelThe invention relates to an antimicrobial agent which is characterized by a content of triphenyltin [pyridyl-N-oxide (2)] sulfide. This probably owns the formula
nung, in der noch eine vollständige Hemmung der Keime erreicht wurde:in which a complete inhibition of the germs was still achieved:
Dabei erfolgt die Herstellung der neuen Verbindung durch Umsetzung von 2-Mercaptopyridin-N-oxid mit einer Verbindung der FormelThe new compound is produced by reacting 2-mercaptopyridine-N-oxide with a compound of the formula
(QH5J3SnX(QH 5 J 3 SnX
wobei X die Hydroxylgruppe oder das Anion einer anorganischen oder organischen Säure bedeutet. Nur beispielsweise sei eine Herstellungsvariante erläutert:where X is the hydroxyl group or the anion of an inorganic or organic acid. Just For example, a manufacturing variant is explained:
36.7 g (0,1 Mol) Triphenylzinnhydroxid und 12,7 g (0,1 Mol) 2-Mercaptopyridin-N-oxid werden unter Rühren in. 200 ecm Benzol gelöst. Nach einiger Zeit wird das Benzol abdestilliert, der zurückbleibende Sirup wird aus Äthanol kristallisiert. Man erhält36.7 g (0.1 mol) of triphenyltin hydroxide and 12.7 g (0.1 mol) of 2-mercaptopyridine-N-oxide are under Stirring dissolved in 200 ecm benzene. After some time, the benzene that remains is distilled off Syrup is crystallized from ethanol. You get
43.8 g (92% der Theorie) Triphenylzinn-[pyridyl- jo N-oxid-(2)]-sulfid vom F. = 1 K) bis 112°C. .43.8 g (92% of theory) triphenyltin [pyridyl- jo N-oxide (2)] sulphide from M. = 1 K) to 112 ° C. .
Die oben angeführte Struktur der neuen Verbindung wird durch die Arbeit von I. R. B e a t t i e und Mitarbeiter in Chem. Ind., 1962, 1429-30, über 5-koordiniertes Zinn sowie durch das UV- und IR-Spektrum nahegelegt. Das UV-Spektrum der neuen Verbindung ist ähnlich, aber nicht identisch mit dem des 2-Mercaptopyridin-N-oxids: Die Elektronenstruktur im Pyridinring hat sich geändert, während dies im Spektrum des Triphenylzinn-[pyridyl-(2)]-suliids nicht der Fall ist. Auch im IR-Spektrum sind lediglich die Banden des Triphenylzinns unverändert, während fast alle Gerüstschwingurigen im 2-Mercaptopyridin-N-oxid mehr oder weniger verschoben sind. Dadurch ist eine Wechselwirkungder N— O-Bindung mit dem Zinn bewiesen.The above structure of the new compound is confirmed by the work of I. R. B e a t t i e and coworkers in Chem. Ind., 1962, 1429-30, about 5-coordinated tin as well as by the UV and IR spectrum suggested. The UV spectrum of the new compound is similar but not identical to that of 2-mercaptopyridine-N-oxide: The electronic structure in the pyridine ring has changed while this is in the spectrum of triphenyltin [pyridyl (2)] sulfide is not the case. Also in the IR spectrum only the bands of the triphenyltin are unchanged, while almost all scaffolding vibrations in 2-mercaptopyridine-N-oxide are more or less shifted. This is an interaction of the N-O bond proved with the tin.
Die neue Verbindung weist eine gute bakterizide und fungizide Wirksamkeit bei geringer Toxizilät auf, besonders hervorzuheben ist ihre gute Wirksamkeit gegen Ilautpilze, beispielsweise gegen Epi- 5" dermophyton.The new compound exhibits good bactericidal and fungicidal effectiveness with low toxicity on, especially to be emphasized is their good effectiveness against Ilaut fungi, for example against Epi- 5 " dermophyton.
Das erfindungsgemäß hergestellte Triphenylzinn-[pyridyI-N-oxid-(2)]-sulfid (I) ist der in der belgischen Patentschrift 590 498 beschriebenen Verbindung Bis-(2-pyridyl)-I-oxyd)-disulfid (If) hinsichtlich der antimikrowellen Wirkung überlegen, wie sich aus den nachstehenden Versuchen ergibt.The triphenyltin [pyridyl-N-oxide- (2)] sulfide prepared according to the invention (I) is the compound described in Belgian patent 590 498 bis (2-pyridyl) -I-oxide) disulfide (If) regarding the anti-microwave effect, consider how from the the following experiments.
Die Verbindungen wurden vergleichend im Reihenverdünnungstest geprüft. Angegeben ist die Verdün-The compounds were tested for comparison in the serial dilution test. The specified is the thinner
IOIO
1
Γ
1
1
11
1
Γ
1
1
1
1 Million
50000
100 000
1 Million
100 0001 million
1 million
50000
100,000
1 million
100,000
SG 511 Staphylococcus aureus
SG 511
Escherichia coli
ATCC 9637
Candida albicans St 8 ...
Epidermophyton K. W.
Aspergillus niger Streptococcus aronson, ..
Escherichia coli
ATCC 9637
Candida albicans St 8 ...
Epidermophyton KW
Aspergillus niger
100000
5 000
100 000
100 000
100000100,000
100,000
5,000
100,000
100,000
100,000
15 Aus der Tabelle ist ersichtlich, daß die erfindungsgemäi3 hergestellte Verbindung sowohl bei grampositiven als auch bei gramnegativen Keimen eine ganz erheblich bessere Wirkung besitzt und auch Hautpilze stärker gehemmt werden. 15 From the table it can be seen that in both gram-positive as well as Gram-negative germs erfindungsgemäi3 the prepared compound has a significantly better effect and skin fungi are more inhibited.
Die neuen antimikrobiellen Mittel enthalten neben dem Wirkstoff noch einen der üblichen festen oder flüssigen Trägerstoffe und gegebenenfalls noch oberflächenwirksame Stoffe, Dispergier- und Haftmittel. Die Verarbeitung des Wirkstoffes zu antimikrobiellen Mitteln erfolgt auf übliche Weise. Die nachstehenden Beispiele erläutern die Verarbeitung der neuen Verbindung zu antimikrobiellen Mitteln.In addition to the active ingredient, the new antimicrobial agents also contain one of the usual solid or liquid carriers and optionally also surface-active substances, dispersants and adhesives. The processing of the active ingredient into antimicrobial agents takes place in the usual way. The following Examples illustrate the processing of the new compound into antimicrobial agents.
EmulsionskonzentratEmulsion concentrate
20 Teile Triphenylzinn-[pyridyl-N-oxid-(2)]-sulfid werden unter Rühren in ein Gemisch aus 70 Teilen Xylol und 5 Teilen Butanon-2 eingetragen und anschließend mit 5 Teilen Nonylphenolpolyglykoläther versetzt.20 parts of triphenyltin [pyridyl-N-oxide (2)] sulfide are added to a mixture of 70 parts with stirring Entered xylene and 5 parts of butanone-2 and then with 5 parts of nonylphenol polyglycol ether offset.
Beispiel 2
SuspensionspulverExample 2
Suspension powder
50 Teile Triphenylzinn-[pyridyI-N-oxid-(2)]-sulfid werden mit 5 Teilen wasserfreiem Natriumsulfat und 35 Teilen Koalin vermengt und anschließend mit50 parts of triphenyltin [pyridyI-N-oxide (2)] sulfide are mixed with 5 parts of anhydrous sodium sulfate and 35 parts Koalin mixed and then with
9 Teilen Natriumligninsulfonat und einem Teil Natriumtetrapropylenbenzolsulfonat versetzt.9 parts of sodium lignosulfonate and one part of sodium tetrapropylene benzene sulfonate offset.
Beispiel 3
StäubemittelExample 3
Dust
IO Teile Triphenylzinn-[pyridyl-N-oxid-(2)]-sulfid,IO parts of triphenyltin [pyridyl-N-oxide (2)] sulfide,
10 Teile Kieselgur, 25 Teile Tonmehl und 55 Teile Talkum werden gemischt und fein gemahlen.10 parts of kieselguhr, 25 parts of powdered clay and 55 parts of talc are mixed and finely ground.
Claims (1)
Family
ID=
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