DE1298092B - Aryl thiocarbamates - Google Patents
Aryl thiocarbamatesInfo
- Publication number
- DE1298092B DE1298092B DE1962N0021736 DEN0021736A DE1298092B DE 1298092 B DE1298092 B DE 1298092B DE 1962N0021736 DE1962N0021736 DE 1962N0021736 DE N0021736 A DEN0021736 A DE N0021736A DE 1298092 B DE1298092 B DE 1298092B
- Authority
- DE
- Germany
- Prior art keywords
- naphthyl
- compounds
- general formula
- mixture
- nos
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Description
Die Erfindung betrifft neue Arylthiocarbamate der allgemeinen FormelThe invention relates to new aryl thiocarbamates of the general formula
Ar1-N-C-O-Ar2 Ar 1 -NCO-Ar 2
I Il c I Il c
CH3 SCH 3 S
worin Ar1 für einen 1-Naphthyl-, Phenyl-, Tolyl- oder Chlorphenylrest steht und Ar2 einen 2-Naphthyl-, Tolyl-, Chlorphenyl-, Bromphenyl- oder Methoxyphenylrest bedeutet mit der Maßgabe, daß mindestens einer der Reste Ar1 und Ar2 ein Naphthylrest ist. Ferner fällt in den Rahmen der Erfindung ein Verfahren zur Herstellung der vorstehend beschriebenen Arylthiocarbamate, welches dadurch gekennzeichnet ist, daß ein Amin der allgemeinen Formelwherein Ar 1 is a 1-naphthyl, phenyl, tolyl or chlorophenyl radical and Ar 2 is a 2-naphthyl, tolyl, chlorophenyl, bromophenyl or methoxyphenyl radical, with the proviso that at least one of Ar 1 and Ar 2 is naphthyl. The scope of the invention also includes a process for the preparation of the arylthiocarbamates described above, which is characterized in that an amine of the general formula
Ar1-N-HAr 1 -NH
CH3 CH 3
in an sich bekannter Weise mit einem Arylchlorthioformiat der allgemeinen Formelin a manner known per se with an aryl chlorothioformate of the general formula
Cl-C-O-Ar2 Cl-CO-Ar 2
25 Beispiel 1 N-Methyl-N-phenyl^-naphthylthiocarbamat 25 Example 1 N-methyl-N-phenyl ^ -naphthylthiocarbamat
Eine Mischung aus 10,7 g N-Methylanilin und 8,4 g Natriumhydrogencarbonat in 100 ecm Aceton wird bei einer Temperatur von 0 bis 1O0C gerührt, worauf 22,3 g 2-Naphthylchlorthioformiat, welches durch de'n Umsatz von Thiophosgen und 2-Naphthol als orangefarbene Kristalle vom Schmelzpunkt 73 bis 74°C erhalten worden war, in kleinen Anteilen zugefügt wird. Nach Beendigung der Reaktion wird die Mischung 15 Minuten am Rückflußkühler erhitzt, abgekühlt und in etwa 200 ecm kaltes Wasser gegossen, wodurch das Reaktionsprodukt in Form von weißen Kristallen erhalten wird. Die Ausbeute beträgt 26,0 g. Nach der Umkristallisation aus Äthanol werden kristalline, farblose Nadeln vom Schmelzpunkt 131 bis 1320C erhalten. Analysenwerte für C18H1SNOS:A mixture of 10.7 g of N-methylaniline and 8.4 g of sodium hydrogen carbonate in 100 ecm of acetone is stirred at a temperature of 0 to 1O 0 C, whereupon 22.3 g of 2-naphthylchlorothioformate, which by de'n conversion of thiophosgene and 2-naphthol was obtained as orange-colored crystals with a melting point of 73 to 74 ° C, is added in small portions. After the reaction has ended, the mixture is refluxed for 15 minutes, cooled and poured into about 200 ecm of cold water, whereby the reaction product is obtained in the form of white crystals. The yield is 26.0 g. After recrystallization from ethanol, crystalline, colorless needles with a melting point of 131 to 132 ° C. are obtained. Analysis values for C 18 H 1S NOS:
Berechnet N 4,78%; gefunden N 4,51%.Calculated N 4.78%; found N 4.51%.
N-Methyl-N-(4-chlorphenyl)-2-naphthylthiocarbamat N-methyl-N- (4-chlorophenyl) -2-naphthylthiocarbamate
umgesetzt wird, wobei in diesen Formeln Ar1 und Ar2 die vorstehend angegebenen Bedeutungen besitzen. is reacted, where in these formulas Ar 1 and Ar 2 have the meanings given above.
Die vorstehend angegebene Umsetzung wird in vorteilhafter Weise in einem geeigneten Lösungsmittel, wie beispielsweise Wasser, Äthanol, Methanol, Aceton oder Chloroform, durchgeführt. Als Chlorwasserstoffakzeptoren werden vorzugsweise Alkalihydrogencarbonate, Alkalicarbonate, Alkalihydroxyde, Erdalkalihydroxyde, tertiäre Amine oder das umgesetzte Amin verwendet.The above reaction is advantageously carried out in a suitable solvent, such as water, ethanol, methanol, acetone or chloroform. As hydrogen chloride acceptors are preferably alkali hydrogen carbonates, alkali carbonates, alkali hydroxides, alkaline earth hydroxides, tertiary amines or the converted amine used.
Die Reaktionstemperatur liegt zwischen 0 und 1000C, während eine Reaktionszeit eingehalten wird, die zwischen 10 und 120 Minuten schwankt.The reaction temperature is between 0 and 100 ° C., while a reaction time is maintained which varies between 10 and 120 minutes.
Bei der Verwendung von Wasser als Reaktionsmedium fällt das Endprodukt nach beendeter Umsetzung aus. Wird ein organisches Lösungsmittel eingesetzt, so kann man das Endprodukt nach beendeter Reaktion durch Verdampfen des Lösungsmittels in Form eines festen Rückstandes erhalten. Die Reaktionsprodukte können mit Wasser gewaschen und durch Umkristallisation aus einem geeigneten organischen Lösungsmittel, wie Aceton, Alkohol, Benzol oder Tetrachlorkohlenstoff, gereinigt werden.If water is used as the reaction medium, the end product falls after the reaction has ended the end. If an organic solvent is used, the end product can be used after the end Reaction obtained by evaporating the solvent in the form of a solid residue. The reaction products can be washed with water and recrystallized from a suitable organic solvents such as acetone, alcohol, benzene or carbon tetrachloride will.
Das für das erfindungsgemäße Verfahren eingesetzte Arylchlorthioformiat der vorstehend angegebenen allgemeinen Formel wird durch Umsetzung von Phenol, Naphthol oder einer heterocyclischen Hydroxylverbindung mit Thiophosgen in Gegenwart eines Chlorwasserstoffakzeptors hergestellt.The aryl chlorothioformate used for the process according to the invention of the abovementioned general formula is obtained by reacting phenol, naphthol or a heterocyclic hydroxyl compound made with thiophosgene in the presence of a hydrogen chloride acceptor.
Die erfindungsgemäßen Arylthiocarbamate besitzen eine Aktivität gegenüber Pilzinfektionen der Haut (wie beispielsweise Trichophytia) und sind ferner als Fungizide, beispielsweise zur Behandlung von Reismehltau und Blattmehltau geeignet, wobei sie bekannten ähnlichen Verbindungen, beispielsweise den Verbindungen, die in der deutschen Auslegeschrift 1 067 425 beschrieben werden, überlegen sind, wie aus der weiter unten folgenden Gegenüberstellung hervorgeht.The aryl thiocarbamates according to the invention have an activity against fungal infections of the skin (such as Trichophytia) and are also used as fungicides, for example for the treatment of rice powdery mildew and powdery mildew, using known similar compounds, for example the Compounds that are described in German Auslegeschrift 1 067 425 are superior to how from the comparison below.
Die folgenden Beispiele erläutern die Herstellung von erfindungsgemäßen Verbindungen.The following examples illustrate the preparation of compounds according to the invention.
Eine Mischung aus 14,2 g N-Methyl-4-chloranilin und 8,4 g Natriumhydrogencarbonat in 100 ecm Wasser wird bei 0 bis 100C gerührt, worauf 22,3 g des fein pulverisierten 2-Naphthylchlorthioformiats in kleinen Anteilen zugegeben werden. Die Mischung wird nach erfolgter Zugabe 1 Stunde bei 10 bis 15° C gerührt, worauf die ausfallenden Kristalle durch Filtration gesammelt, mit Wasser gewaschen und getrocknet werden. Es werden 31,0 g des Endproduk-A mixture of 14.2 g of N-methyl-4-chloroaniline and 8.4 g of sodium bicarbonate in 100 cc of water is stirred at 0 to 10 0 C, after which 22.3 g of finely pulverized 2-Naphthylchlorthioformiats in small portions was added. After the addition has taken place, the mixture is stirred at 10 to 15 ° C. for 1 hour, whereupon the crystals which precipitate are collected by filtration, washed with water and dried. 31.0 g of the end product are
tes erhalten. Die Ausbeute beträgt 95%. Die Umkristallisation aus Äthanol ergibt kristalline, farblose Nadeln vom Schmelzpunkt 127 bis 128° C. Analytische Daten für Ci8HhCINOS :tes received. The yield is 95%. Recrystallization from ethanol produces crystalline, colorless needles with a melting point of 127 to 128 ° C. Analytical data for Ci 8 HhCINOS:
Berechnet N 4,28%; gefunden N 4,49%. 40 Calculated N 4.28%; found N 4.49%. 40
Beispiel 3 N-Methyl-N-(3-tolyl)-2-naphthylthiocarbamatExample 3 N-Methyl-N- (3-tolyl) -2-naphthylthiocarbamate
Eine Mischung aus 4,0 g N-Methyl-3-toluidin und 2,8 g Natriumhydrogencarbonat in 50 ecm Aceton wird bei 0 bis 100C gerührt, worauf 7,4 g 2-Naphthylchlorthioformiat in geringen Anteilen zugegeben werden. Diese Mischung wird 30 Minuten am Rückflußkühler erhitzt. Die abgekühlte Mischung wird in etwa 150 ecm kaltes Wasser eingegossen. Das Endprodukt wird mit einer Ausbeute von 1,9 g (90%) als weiße Kristalle erhalten. Die Umkristallisation aus Alkohol ergibt kristalline, farblose Nadeln vom Schmelzpunkt 110,5 bis 111,5° C. Analysendaten für C19H17NOS:A mixture of 4.0 g of N-methyl-3-toluidine and 2.8 g of sodium bicarbonate in 50 cc of acetone is stirred at 0 to 10 0 C, after which 7.4 g of 2-Naphthylchlorthioformiat be added in small amounts. This mixture is refluxed for 30 minutes. The cooled mixture is poured into about 150 ecm of cold water. The end product is obtained as white crystals in a yield of 1.9 g (90%). Recrystallization from alcohol gives crystalline, colorless needles with a melting point of 110.5 to 111.5 ° C. Analysis data for C 19 H 17 NOS:
Berechnet N 4,56%; gefunden N 4,10%·Calculated N 4.56%; found N 4.10%
Beispiel 4 N-Methyl-N-(l-naphthyl)-4-chlorphenylthiocarbamatExample 4 N-Methyl-N- (1-naphthyl) -4-chlorophenylthiocarbamate
Eine Mischung von 15,7 g N-Methyl-1-naphthylamin und 8,4 g Natriumhydrogencarbonat in 100 ecm Äthanol wird bei 0 bis 1O0C gerührt, worauf 20,7 g 4-Chlorphenylchlorthioformiat tropfenweise zugefügt werden. Nach Beendigung der Reaktion wird die Reaktionsmischung 30 Minuten bei 45 bis 50°C gerührt, abgekühlt und in etwa 200 ecm kaltes Wasser eingegossen, wodurch das Endprodukt als weißeA mixture of 15.7 g of N-methyl-1-naphthylamine and 8.4 g of sodium bicarbonate in 100 cc of ethanol is stirred at 0 to 1O 0 C, after which 20.7 g of 4-Chlorphenylchlorthioformiat are added dropwise. After the reaction has ended, the reaction mixture is stirred for 30 minutes at 45 to 50 ° C., cooled and poured into about 200 ecm of cold water, whereby the end product is white
Kristalle in einer Ausbeute von 29,5 g erhalten wird. Die Umkristallisation aus Äthanol ergibt kristalline, farblose Nadeln vom Schmelzpunkt 115,5 bis 116,5° C.Crystals are obtained in a yield of 29.5 g. Recrystallization from ethanol gives crystalline, colorless needles with a melting point of 115.5 to 116.5 ° C.
Analysendaten für Ci8Hi4CINOS:Analysis data for Ci 8 Hi 4 CINOS:
Berechnet N 4,28%; gefunden N 4,21%. Beispiel 5Calculated N 4.28%; found N 4.21%. Example 5
N-Methyl-N-(l-naphthyl)-naphthylthiocarbamatN-methyl-N- (1-naphthyl) naphthyl thiocarbamate
Eine Mischung von 15,7 g N-Methyl-1-naphthylamin und 5,3 g Natriumcarbonat in 100 ecm Aceton wird auf 0 bis 100C abgekühlt, worauf 22,3 g 2-Naphthylchlorthioformiat in kleinen Anteilen hinzugefügt werden. Die Mischung wird 30 Minuten am Rückfiußkühler erhitzt, abgekühlt und in etwa 200 ecm kaltes Wasser eingegossen, wodurch das Endprodukt 5 als weiße Kristalle in einer Ausbeute von 30,5 g erhalten wird. Die Umkristallisation aus einer Mischung von Alkohol und Aceton ergibt kristalline, farblose Nadeln vom Schmelzpunkt 147° C.A mixture of 15.7 g of N-methyl-1-naphthylamine and 5.3 g of sodium carbonate in 100 cc of acetone is cooled to 0 to 10 0 C, after which 22.3 g of 2-Naphthylchlorthioformiat are added in small portions. The mixture is heated on a reflux condenser for 30 minutes, cooled and poured into about 200 ecm of cold water, whereby the end product 5 is obtained as white crystals in a yield of 30.5 g. Recrystallization from a mixture of alcohol and acetone gives crystalline, colorless needles with a melting point of 147 ° C.
Analysenwerte für C22H17NOS: ίο Berechnet N 4,09%; gefunden N 3,80%.Analysis values for C 22 H 17 NOS: ίο calculated N 4.09%; found N 3.80%.
Die erfindungsgemäßen Verbindungen sind in der nachstehenden Tabelle zusammengefaßt.The compounds according to the invention are summarized in the table below.
Verbindung link
Nr.No.
Ar1 Ar 1
Ar,Ar,
F. (3C)F. ( 3 C)
Formelformula
N-Analyse (%) berechnet gefundenN analysis (%) found calculated
/ V/ V
CH.CH.
CH3 CH 3
ClCl
ClCl
OCH3 OCH 3
BrBr
104 bis 105104 to 105
105 bis 106105 to 106
141 bis 142141 to 142
124 bis 125124 to 125
108 bis 109108 to 109
115,5 bis 116115.5 to 116
107 bis 108107 to 108
141 bis 142141 to 142
C19H17NOSC 19 H 17 NOS
C19H17NOSC 19 H 17 NOS
C19H17NOSC 19 H 17 NOS
C18H14ClNOSC 18 H 14 ClNOS
C18H14ClNOSC 18 H 14 ClNOS
C18H14ClNOSC 18 H 14 ClNOS
C19H17NO2SC 19 H 17 NO 2 S
C18H14BrNOSC 18 H 14 BrNOS
C22H17NOSC 22 H 17 NOS
C18H15NOSC 18 H 15 NOS
4,564.56
4,564.56
4,564.56
4,284.28
4,284.28
4,284.28
4,344.34
3,763.76
4,074.07
4,774.77
4,304.30
4,454.45
4,264.26
3,953.95
3,903.90
4,214.21
3,933.93
3,503.50
3,803.80
4,514.51
Fortsetzungcontinuation
Verbindung Nr.link No.
Ar1 Ar 1
Ar2 Ar 2
F. (C)F. (C)
Formelformula
N-Analyse'(%)
berechnet gefundenN analysis' (%)
calculated found
CH,CH,
110 bis110 to
118 bis118 to
127 bis127 to
110,5 bis 111,5110.5 to 111.5
117 bis117 to
110 bis C18H1XlNOS110 to C 18 H 1 XINOS
C1=H1XlNOSC 1 = H 1 XINOS
C18H1XlNOSC 18 H 1 XINOS
C19H17NOSC 19 H 17 NOS
C19H17NOSC 19 H 17 NOS
C19H17NOSC 19 H 17 NOS
4,284.28
4,284.28
4,284.28
4,564.56
4,564.56
4,564.56
4,234.23
4,104.10
4,494.49
4,104.10
4,354.35
4,304.30
Die erfindungsgemäßen Arylthiocarbamate sind den in der deutschen Auslegeschrift 1 067 425 beschriebenen Thiocarbamidsäure-O-arylestern auf den vorstehend angegebenen Anwendungsgebieten überlegen, wie aus den nachstehenden Ausführungen hervorgeht:The aryl thiocarbamates according to the invention are those described in German Auslegeschrift 1,067,425 Thiocarbamic acid O-aryl esters are superior in the fields of application given above, as can be seen from the following statements:
Es wurden Vergleichsversuche unter Verwendung von repräsentativen Vertretern der erfindungsgemäßen Verbindungen im Vergleich zu den wirksamsten, aus der deutschen Auslegeschrift 1 067 425 bekannten Verbindungen der FormelnThere were comparative experiments using representative representatives of the invention Compounds in comparison to the most effective ones known from German Auslegeschrift 1,067,425 Connections of the formulas
4040
CH2-NH-C-OCH 2 -NH-CO
(CH2), — NHC — O —<( ■(CH 2 ), - NHC - O - <(■
/ V-(CH2J2-NHC-O-^/ V- (CH 2 J 2 -NHC-O- ^
OCH,OCH,
4545
""
6060
hinsichtlich der fungiziden Aktivität sowohl in vitro als auch in vivo durchgeführt. Außerdem wurden viele andere konstitutionell und wirkungsmäßig ahn-in terms of fungicidal activity both in vitro as well as in vivo. In addition, many others were constitutionally and effectively
65 liehe vergleichbare bekannte Verbindungen hinsichtlich ihrer Aktivität auf dem erwähnten Gebiet untersucht. 65 borrowed comparable known compounds with regard to investigated their activity in the field mentioned.
Bei dem Aktivitätstest in vitro ließ man Lösungen der zu untersuchenden Verbindungen auf eine Suspension einer Kultur von Trichophyton mentagrophytes, Species interdigitale, einwirken. Aus den Versuchsergebnissen geht hervor, daß lediglich die erfindungsgemäßen Verbindungen eine zufriedenstellende Anti-Trichophyton-Aktivität aufwiesen.In the in vitro activity test, solutions of the compounds to be examined were left on a suspension a culture of Trichophyton mentagrophytes, Species interdigitale. From the test results it can be seen that only the invention Compounds exhibited satisfactory anti-Trichophyton activity.
Da die Wirksamkeit in vitro jedoch noch nichts darüber aussagt, ob diese Verbindungen auch in vivo wirksam sind, wurden die erfindungsgemäßen Verbindungen und die bekannten Vergleichsverbindungen einem Aktivitätstest in vivo unterworfen, der auf der Haut lebender Meerschweinchen durchgeführt wurde. Als Testfungus wurde in diesem Versuch Trichophyton mentagrophytes, Species esteroides, verwendet. Die zu untersuchenden Verbindungen wurden in Form einer 2%igen Lösung bei der Behandlung einer auf dem Rücken von Meerschweinchen künstlich hervorgerufenen Oberflächentrichophytose getestet. Dabei zeigt sich, daß nur die erfindungsgemäßen Verbindungen auf die künstlich erzeugte Dermatomycose der Meerschweinchen eine hohe Wirksamkeit besaßen, während die bereits bekannten VerbindungenHowever, since the effectiveness in vitro does not say anything about whether these compounds are also in vivo are effective, the compounds according to the invention and the known comparative compounds subjected to an in vivo activity test carried out on the skin of live guinea pigs. Trichophyton mentagrophytes, Species esteroides, was used as the test fungus in this experiment. the Compounds to be examined were in the form of a 2% solution in the treatment of a Artificially induced surface trichophytosis in the back of guinea pigs was tested. Included it turns out that only the compounds according to the invention affect artificially produced dermatomycosis the guinea pigs were highly effective, while the already known compounds
der Formel Ar1-NH-C-OAr2 of the formula Ar 1 -NH-C-OAr 2
nur mäßig wirksam oder unwirksam waren und schwere Hautreizungen hervorriefen und die aus der deutschen Auslegeschrift 1 067 425 bekannten Verbindungen völlig unwirksam waren.were only moderately effective or ineffective and caused severe skin irritation and those from the German Auslegeschrift 1,067,425 known compounds were completely ineffective.
Claims (2)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2136061 | 1961-06-21 | ||
| JP3033561 | 1961-08-25 | ||
| JP1356062 | 1962-04-09 | ||
| JP1438462 | 1962-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1298092B true DE1298092B (en) | 1969-06-26 |
Family
ID=26196271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962N0021736 Pending DE1298092B (en) | 1961-06-21 | 1962-06-22 | Aryl thiocarbamates |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1298092B (en) |
| FR (1) | FR1337797A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090263A1 (en) * | 1982-03-17 | 1983-10-05 | Tosoh Corporation | Carbamate derivatives, process for producing the same and herbicides comprising the compounds as an effective component |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA731497B (en) * | 1972-03-20 | 1973-12-19 | Erba Carlo Spa | Thiocarbamic acid derivatives and process for their preparation |
| JPS523829A (en) * | 1975-06-11 | 1977-01-12 | Nippon Kayaku Co Ltd | Germicides for agriculture and gardening |
| US4554012A (en) * | 1982-06-10 | 1985-11-19 | Toyo Soda Manufacturing Co., Ltd. | Aryl N-alkyl-N-(pyridyl or pyrimidyl) carbamate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067425B (en) * | 1959-10-22 | Deutsche Akademie der Wissenschaften zu Berlin, Berlin-Adlershof | Process for the production of bactericidal, fungicidal and virustatic thiocarbamic acid O-aryl esters |
-
1962
- 1962-06-21 FR FR901533A patent/FR1337797A/en not_active Expired
- 1962-06-22 DE DE1962N0021736 patent/DE1298092B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067425B (en) * | 1959-10-22 | Deutsche Akademie der Wissenschaften zu Berlin, Berlin-Adlershof | Process for the production of bactericidal, fungicidal and virustatic thiocarbamic acid O-aryl esters |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090263A1 (en) * | 1982-03-17 | 1983-10-05 | Tosoh Corporation | Carbamate derivatives, process for producing the same and herbicides comprising the compounds as an effective component |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1337797A (en) | 1963-09-20 |
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