DE1111641B - Process for the preparation of rhodantriazines - Google Patents

Process for the preparation of rhodantriazines

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Publication number
DE1111641B
DE1111641B DED28588A DED0028588A DE1111641B DE 1111641 B DE1111641 B DE 1111641B DE D28588 A DED28588 A DE D28588A DE D0028588 A DED0028588 A DE D0028588A DE 1111641 B DE1111641 B DE 1111641B
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DE
Germany
Prior art keywords
triazine
cooled
solution
ncs
general formula
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
Application number
DED28588A
Other languages
German (de)
Inventor
Dr Werner Schwarze
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Priority to DED28588A priority Critical patent/DE1111641B/en
Priority to CH7504759A priority patent/CH387645A/en
Priority to FR800515A priority patent/FR1271043A/en
Priority to GB2532459A priority patent/GB930594A/en
Publication of DE1111641B publication Critical patent/DE1111641B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

D 28588 IVb/12pD 28588 IVb / 12p

ANMELDETAG: 24. JULI 1958REGISTRATION DATE: JULY 24, 1958

BEKANNTMACHUNG
DER ANMELDUNG
UNDAUSGABE DER
AUSLEGESCHRIFT: 27. JULI 1961 NOTICE
THE REGISTRATION
AND ISSUE OF
EDITORIAL: JULY 27, 1961

Es ist bekannt, 2-Thiocyano-4,6-diamino-s-triazin dadurch herzustellen, daß man Thiocyansäure mit 2-Chlor-4,6-diamino-s-triazin in Wasser reagieren läßt und das ausgefällte Triazinderivat isoliert. Nach diesem Verfahren lassen sich aber andere Verbindungen dieser Art, bei denen mindestens ein Aminowasserstoff durch eine organische Gruppe ersetzt ist, mit Rhodanwasserstoff in Gegenwart von Wasser nicht umsetzen.It is known that 2-thiocyano-4,6-diamino-s-triazine can be prepared by using thiocyanic acid Reacts 2-chloro-4,6-diamino-s-triazine in water and isolates the precipitated triazine derivative. To However, this process can be used with other compounds of this type in which at least one amino hydrogen is replaced by an organic group, do not react with hydrogen rhodanide in the presence of water.

Es wurde nun überraschenderweise gefunden, daß es möglich ist, Rhodanderivate des s-Triazins der allgemeinen FormelIt has now surprisingly been found that it is possible to use rhodan derivatives of s-triazine in general formula

NCS-C"
NNCS-C "
N

C-X NCS-C
oderCX NCS-C
or

,N N, N N

,N, N

"C"C

C—SCNC-SCN

Verfahren zur Herstellung
von RhodantriazinenMethod of manufacture
of rhodantriazines

Anmelder:
Deutsche Gold- und Silber-ScheideanstaltApplicant:
German gold and silver separator

vormals Roessler,
Frankfurt/M., Weißfrauenstr. 9formerly Roessler,
Frankfurt / M., Weißfrauenstr. 9

Dr. Werner Schwarze, Frankfurt/M.,
ist als Erfinder genannt wordenDr. Werner Schwarze, Frankfurt / M.,
has been named as the inventor

X XX X

herzustellen, wenn man Mercaptotriazine der allgemeinen Formelproduce when using mercaptotriazines of the general formula

Nv ,NN v , N

HS-C C-X HS—C'' C-SHHS-C C-X HS-C "C-SH

oderor

N-N-

,N, N

N,N,

,N, N

mit der etwa äquimolekularen Menge eines Halogencyans in Gegenwart eines Lösungsmittels umsetzt. In diesen Formeln bedeutet X eine SH- oder NH2-Gruppe oder einen gegebenenfalls substituierten, aliphatischen, aromatischen, araliphatischen oder cycloaliphatischen Rest, der als solcher oder über Sauerstoff, Schwefel oder Stickstoff an den Triazinring gebunden ist. Als Lösungsmittel können Wasser, Alkohole, Ketone oder deren Gemische verwendet werden; am zweckmäßigsten arbeitet man mit Wasser. Man suspendiert hierbei die umzusetzende Mercaptoverbindung und gibt gegebenenfalls so viel eines Akzeptors für Halogenwasserstoff zu, daß das entsprechende Alkalisalz gebildet wird. Als ein solcher Akzeptor kann beispielsweise Natronlauge verwendet werden. Die Menge des zuzusetzenden Akzeptors entspricht normalerweise der Anzahl der SH-Gruppen. Im Falle des Trimercaptotriazins werden aber zur Neutralisation nur 2 Mol Alkalihydroxyd benötigt; es reagieren demnach nur zwei SH-Gruppen unter Bildung von 2,4-Dirhodano-6-mercaptotriazin.with the approximately equimolecular amount of a cyanogen halide in the presence of a solvent. In these formulas, X denotes an SH or NH 2 group or an optionally substituted, aliphatic, aromatic, araliphatic or cycloaliphatic radical which is bonded to the triazine ring as such or via oxygen, sulfur or nitrogen. Water, alcohols, ketones or mixtures thereof can be used as solvents; the best way to work is with water. The mercapto compound to be reacted is suspended and, if necessary, enough of an acceptor for hydrogen halide is added so that the corresponding alkali metal salt is formed. Sodium hydroxide solution, for example, can be used as such an acceptor. The amount of acceptor to be added normally corresponds to the number of SH groups. In the case of trimercaptotriazine, however, only 2 moles of alkali metal hydroxide are required for neutralization; accordingly only two SH groups react to form 2,4-dirhodano-6-mercaptotriazine.

Die Umsetzung muß bei einer Temperatur durchgeführt werden, bei welcher das Halogencyan nicht selbst mit dem Lösungsmittel reagieren kann, d. h. zwischen etwa —50 und + 1000C. Zweckmäßig arbeitet man bei niederer Temperatur, am besten zwischen —10 und -MO0C. Es ist aber auch möglich, unter Druck bei höherer Temperatur zu arbeiten.The reaction must be carried out at a temperature at which the cyanogen halide can not react itself with the solvent, that is, between about -50 and + 100 0 C. Conveniently the reaction is carried at low temperature, preferably between -10 and 0 C. -MO But it is also possible to work under pressure at a higher temperature.

Die nach diesem Verfahren hergestellten Verbindungen dienen als Zwischenprodukte für organische Synthesen, sie können aber auch als Fungicide und Herbicide eingesetzt werden.The compounds produced by this process serve as intermediates for organic products Syntheses, but they can also be used as fungicides and herbicides.

Beispiel 1example 1

Man löst 54 g o-Chloranilido-dimercaptotriazin in 500 ml 0,8 η-Natronlauge, kühlt auf 00C ab und gibt allmählich 30 g Chlorcyan hinzu. Die Temperatur steigt während der Umsetzung auf +1O0C.54 g of o-chloroanilido-dimercaptotriazine are dissolved in 500 ml of 0.8 η sodium hydroxide solution, cooled to 0 ° C. and 30 g of cyanogen chloride are gradually added. The temperature rises to + 1O 0 C. during the reaction.

Nach insgesamt 30 Minuten saugt man den entstandenen Niederschlag ab und wäscht ihn gut mit Wasser aus. Nach dem Trocknen im Vakuum erhält man 62 g analysenreines o-Chloranilido-dirhodanotriazin vom Schmelzpunkt 1300C; Ausbeute: 96,8% der Theorie.After a total of 30 minutes, the precipitate formed is filtered off with suction and washed thoroughly with water. After drying in vacuo, 62 g of analytically pure o-Chloranilido-dirhodanotriazin of melting point 130 0 C; Yield: 96.8% of theory.

Beispiel 2Example 2

5,4 g p-Chloranilido-dimercaptotriazin löst man in 200 ml 0,2 η-Natronlauge. Man kühlt auf O0C ab und tropft eine Lösung von 5 g Bromcyan in 50 ml Aceton hinzu. Die Temperatur beträgt danach +20C. Anschließend rührt man noch eine Stunde. Der Niederschlag wird abgesaugt und getrocknet. Schmelzpunkt:5.4 g of p-chloroanilido-dimercaptotriazine are dissolved in 200 ml of 0.2 η sodium hydroxide solution. It is cooled to 0 ° C. and a solution of 5 g of cyanogen bromide in 50 ml of acetone is added dropwise. The temperature is then +2 0 C. Then the mixture is stirred one hour. The precipitate is filtered off with suction and dried. Melting point:

109 649/403109 649/403

192°C; Ausbeute: 5,5 g, entsprechend 86% der Theorie an p-Chloranilido-dirhodanotriazin.192 ° C; Yield: 5.5 g, corresponding to 86% of theory, of p-chloroanilido-dirhodanotriazine.

Beispiel 3Example 3

8,9 g Trimercaptotriazin werden in 250 ml 0,4 η-Kalilauge gelöst. Die filtrierte Lösung wird auf O0C abgekühlt, und man leitet bei dieser Temperatur innerhalb von 10 Minuten 6,3 g Chlorcyangas ein. Der dicke, gelbe Niederschlag wird nach einer Stunde abgesaugt, mit Wasser gewaschen und getrocknet.8.9 g of trimercaptotriazine are dissolved in 250 ml of 0.4 η potassium hydroxide solution. The filtered solution is cooled to 0 ° C., and 6.3 g of cyanogen chloride gas is passed in at this temperature over the course of 10 minutes. The thick, yellow precipitate is filtered off with suction after one hour, washed with water and dried.

Auf Grund der C,H,N-Analyse ist die Verbindung Dirhodano-mercaptotriazin; Ausbeute: 10,2 g, entsprechend 78,5% der Theorie; Schmelzpunkt: oberhalb 3500C.Based on the C, H, N analysis, the compound is dirhodano-mercaptotriazine; Yield: 10.2 g, corresponding to 78.5% of theory; Melting point: above 350 ° C.

Beispiel 4Example 4

Man löst 5,4 g Diamino-mercaptotriazin in 100 ml l,6%iger Natronlauge, filtriert, kühlt auf 00C ab und gibt auf einmal 3,0 ml Chlorcyan hinzu. Die Temperatur steigt auf 100C, und es bildet sich ein dicker, weißer Niederschlag. Nach 30 Minuten saugt man ab, wäscht aus und trocknet bei 4O0C im Vakuum.5.4 g of diamino-mercaptotriazine are dissolved in 100 ml of 1.6% strength sodium hydroxide solution, filtered, cooled to 0 ° C. and 3.0 ml of cyanogen chloride are added all at once. The temperature rises to 10 ° C. and a thick, white precipitate forms. After 30 minutes, drained, washed and dried at 4O 0 C under vacuum.

Laut Analyse ist die Verbindung Diamino-rhodanotriazin; Ausbeute: 6,1g, entsprechend 96,1% der Theorie; Schmelzpunkt: oberhalb 3500C.According to analysis, the compound is diamino-rhodanotriazine; Yield: 6.1 g, corresponding to 96.1% of theory; Melting point: above 350 ° C.

Beispiel 5Example 5

Man löst 25,5 g Bis-diäthylamino-mercaptotriazin in 250 ml Aceton und gibt 25 ml 4 n-Natronlauge hinzu, erwärmt kurz und kühlt wieder ab. Bei —5° C gibt man 6 ml Chlorcyan hinzu und rührt bei dieser Temperatur 6 Stunden. Dann dampft man das Aceton im Vakuum ab und nimmt den Rückstand in Methylenchlorid auf. Nach dem Trocknen und Abdampfen des Lösungsmittels verbleiben 27 g Bis-diäthylaminorhodanotriazin. 25.5 g of bis-diethylamino-mercaptotriazine are dissolved in 250 ml of acetone and 25 ml of 4N sodium hydroxide solution are added added, warms up briefly and cools down again. 6 ml of cyanogen chloride are added at -5 ° C. and the mixture is stirred at this point Temperature 6 hours. The acetone is then evaporated off in vacuo and the residue is taken up in methylene chloride on. After drying and evaporation of the solvent, 27 g of bis-diethylaminorhodanotriazine remain.

Farbloses, nicht destillierbares Öl. Ausbeute: 26 g, entsprechend 96% der Theorie.Colorless, non-distillable oil. Yield: 26 g, corresponding to 96% of theory.

Beispiel 6Example 6

8,7 g Äthyl-dimercaptotriazin, gelöst in 200 ml 2%iger Natronlauge, ergeben mit 6 ml Chlorcyan bei 00C nach der üblichen Aufarbeitung 8,9 g, entsprechend 79% der Theorie anÄthyl-dirhodanotriazin; gelbes, nicht destillierbares Öl.8.7 g of ethyl-dimercaptotriazin dissolved in 200 ml of 2% sodium hydroxide solution, resulting with 6 ml cyanogen chloride at 0 0 C. after the usual work-up 8.9 g, corresponding to 79% of theory anÄthyl-dirhodanotriazin; yellow, non-distillable oil.

Beispiel 7Example 7

Man löst 20 g Pentachlorphenoxy-dimercaptotriazin in 400 ml 1 %iger Natronlauge, kühlt auf O0C ab und gibt dann 6,7 ml Chlorcyan hinzu. Die Aufarbeitung liefert 19,8 g Pentachlorphenoxy-dirhodanotriazin, entsprechend 86,4% der Theorie; hellgelbes Pulver. Schmelzpunkt: oberhalb 350°C.20 g of pentachlorophenoxy-dimercaptotriazine are dissolved in 400 ml of 1% strength sodium hydroxide solution, cooled to 0 ° C. and then 6.7 ml of cyanogen chloride are added. Work-up gives 19.8 g of pentachlorophenoxy-dirhodanotriazine, corresponding to 86.4% of theory; light yellow powder. Melting point: above 350 ° C.

Beispiel 8Example 8

Lösung von 3,5 g Chlorcyan in 10 ml Aceton hinzu. Nach 10 Minuten wird die Lösung sauer. Man gießt auf Eis, wobei eine Schmiere ausfällt, die schnell durchkristallisiert. Man nutscht ab, trocknet und kristallisiert aus Benzin um. Man erhält 11,1g 2,4-Bisisopropylamino-6-rhodano-s-triazin in Form feiner weißer Nadeln; F. 79 bis 8O0C.Add a solution of 3.5 g of cyanogen chloride in 10 ml of acetone. After 10 minutes the solution becomes acidic. It is poured onto ice, whereupon a smear precipitates, which quickly crystallizes through. You suction off, dry and recrystallize from gasoline. 11.1 g of 2,4-bisisopropylamino-6-rhodano-s-triazine are obtained in the form of fine white needles; F. 79 to 8O 0 C.

Beispiel 10Example 10

ίο Man löst 11,3 g 2-Äthylamino-4-tert.butylamino-6-mercapto-s-triazin in 50 ml 1 n-NaOH-Lösung und erwärmt die Lösung auf 45 0C. Bei dieser Temperatur leitet man in schnellem Strom Chlorcyangas ein, wobei die Mischung schnell sauer wird. Es fällt eine Schmiere aus, die in einem Gemisch von Benzol und Petroäther umkristallisiert wird. Man erhält 10,74 g 2-Äthylamino-4-tert.butylamino-6-rhodano-s-triazin in Form weißer Kristalle; F. 91 bis 920C.ίο Dissolve 11.3 g of 2-ethylamino-4-tert.butylamino-6-mercapto-s-triazine in 50 ml of 1N NaOH solution and heat the solution to 45 ° C. At this temperature, pass in a fast current Cyanogen chloride gas, the mixture quickly becoming acidic. A grease precipitates and is recrystallized in a mixture of benzene and petroleum ether. 10.74 g of 2-ethylamino-4-tert-butylamino-6-rhodano-s-triazine are obtained in the form of white crystals; F. 91 to 92 0 C.

Beispiel 11Example 11

Man suspendiert 15 g 2,4-Bis-äthylamino-6-mercapto-s-triazin in 75 ml Methanol und kühlt auf 0° C ab. Unter Rühren leitet man Chlorcyangas ein, wobei die Temperatur zeitweise auf 100C ansteigt. Die Triazinverbindung wird bald gelöst. Dann gießt man das Gemisch in kaltes Wasser, wobei Kristalle ausfallen, die abgenutscht werden. Man erhält 15,3 g 2,4-Bisäthylamino-6-rhodano-s-triazin; F. 1050C.15 g of 2,4-bis-ethylamino-6-mercapto-s-triazine are suspended in 75 ml of methanol and the mixture is cooled to 0.degree. Cyanogen chloride gas is passed in with stirring, the temperature rising to 10 ° C. at times. The triazine compound will soon be dissolved. The mixture is then poured into cold water, crystals precipitating which are suction filtered. 15.3 g of 2,4-bisethylamino-6-rhodano-s-triazine are obtained; F. 105 0 C.

Beispiel 12Example 12

Man suspendiert 15 g 2-Dimethylamino-4-isobutylamino-6-mercapto-s-triazin in 100 ml Aceton. Bei 20° C gibt man unter Rühren 6 g flüssiges Chlorcyan hinzu, wobei die Temperatur bis auf 28 0C ansteigt. Nach 10 Minuten verdünnt man mit Wasser und neutralisiert mit Natriumbicarbonat. In Form eines Öles, das bald kristallisiert, fallen 12,25 g 2-Dimethylamino-4-isobutylamino-6-rhodano-s-triazinaus; F. 1080C.15 g of 2-dimethylamino-4-isobutylamino-6-mercapto-s-triazine are suspended in 100 ml of acetone. At 20 ° C while stirring added 6 g of liquid cyanogen chloride, wherein the temperature to 28 0 C increases. After 10 minutes, it is diluted with water and neutralized with sodium bicarbonate. In the form of an oil, which soon crystallizes, 12.25 g of 2-dimethylamino-4-isobutylamino-6-rhodano-s-triazine precipitate; F. 108 0 C.

Beispiel 13Example 13

Man suspendiert 15 g 2-Methylamino-4-isobutylamino-6-mercapto-s-triazin in 75 ml Isopropanol und kühlt auf 00C ab. Dann gibt man auf einmal 6 g flüssiges Chlorcyan zu, wobei die Temperatur auf 15°C ansteigt und die Triazinverbindung gelöst wird. Nach 10 Minuten gießt man in Wasser, wobei ein Öl ausfällt, das bald kristallisiert. Man erhält 15,3 g 2-Methylamino-4-isobutylamino-6-rhodano-s-triazin; F. 780C.Is suspended 15 g of 2-methylamino-4-isobutylamino-6-mercapto-s-triazine in 75 ml of isopropanol and cooled to 0 0 C. 6 g of liquid cyanogen chloride are then added all at once, the temperature rising to 15 ° C. and the triazine compound being dissolved. After 10 minutes, it is poured into water, an oil precipitating which soon crystallizes. 15.3 g of 2-methylamino-4-isobutylamino-6-rhodano-s-triazine are obtained; F. 78 0 C.

Claims (1)

PATENTANSPRÜCHE:PATENT CLAIMS: 1. Verfahren zur Herstellung von Rhodantriazinen der allgemeinen Formel1. Process for the preparation of rhodantriazines of the general formula 5555 Man löst 17,3 g Dimethoxy-mercaptotriazin in einer Lösung von 10,1 g Triäthylamin in 100 ml Wasser, kühlt auf 00C ab und leitet langsam 6,6 g Chlorcyangas ein. Es fällt sofort ein dicker, weißer Niederschlag von Dimethoxy-rhodanotriazin aus; Ausbeute: 18,2 g, entsprechend 91,7% der Theorie; Schmelzpunkt: 88 bis 893C.17.3 g of dimethoxymercaptotriazine are dissolved in a solution of 10.1 g of triethylamine in 100 ml of water, the solution is cooled to 0 ° C. and 6.6 g of cyanogen chloride are slowly passed in. A thick, white precipitate of dimethoxy-rhodanotriazine immediately separates out; Yield: 18.2 g, corresponding to 91.7% of theory; Melting point: 88 to 89 3 C. Beispiel 9Example 9 Man suspendiert 11,3g 2,4-Bis-isopropylamino-6-mercapto-s-triazin in 80 ml 80%igern Aceton und fügt 5,05 g Triäthylamin hinzu. Die Mischung wird auf —50° C abgekühlt. Dann tropft man langsam eine ./■11.3 g of 2,4-bis-isopropylamino-6-mercapto-s-triazine are suspended in 80 ml of 80% acetone and adds 5.05 g of triethylamine. The mixture will be on -50 ° C cooled. Then one slowly drips a ./■ NCS-CNCS-C C-X NCS-CC-X NCS-C CC. C SCNC SCN !! oder!! or /N N/ N N ,N, N
wobei X eine SH- oder NH2-Gruppe oder einen gegebenenfalls substituierten, aliphatischen, aromatischen, araliphatischen oder cycloaliphatischen Rest bedeutet, der als solcher oder über Sauerstoff, Schwefel oder Stickstoff an den Triazinring ge-where X denotes an SH or NH 2 group or an optionally substituted, aliphatic, aromatic, araliphatic or cycloaliphatic radical which as such or via oxygen, sulfur or nitrogen is attached to the triazine ring 5 65 6 bunden ist, dadurch gekennzeichnet, daß man eine gencyans in Gegenwart eines Lösungsmittelsis bound, characterized in that one gencyans in the presence of a solvent Triazinverbindung der allgemeinen Formel umsetzt.Reacts triazine compound of the general formula. jq JnJ 2. Verfahren nach Anspruch 1, dadurch gekenn- /' \ /' \ zeichnet, daß man in Gegenwart eines Halogen-HS—C C—X HS—C C—SH 5 wasserstoffakzeptors arbeitet.jq J J n 2 A method according to claim 1, marked by / '\ /' \ is characterized in that a halogen-HS-C C-X HS-CC-SH 5 operates in the presence of hydrogen acceptor. I !j oder Il 3. Verfahren nach Anspruch 1 oder 2, dadurchI! J or II 3. The method according to claim 1 or 2, characterized Νχ. ,N KL .N gekennzeichnet, daß man bei TemperaturenΝ χ . , N KL .N marked that one at temperatures -c · C zwischen —10 und +10° C arbeitet.- c · C operates between -10 and + 10 ° C. -λ- -X-In Betracht gezogene Druckschriften:-λ- -XI n publications considered: mit der etwa äquimolekularen Menge eines Halo- Schweizerische Patentschrift Nr. 314 915.with the approximately equimolecular amount of a halo Swiss patent specification No. 314 915. © 109 649/403 7.61© 109 649/403 7.61
DED28588A 1958-07-24 1958-07-24 Process for the preparation of rhodantriazines Pending DE1111641B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DED28588A DE1111641B (en) 1958-07-24 1958-07-24 Process for the preparation of rhodantriazines
CH7504759A CH387645A (en) 1958-07-24 1959-06-29 Process for the preparation of rhodantriazines
FR800515A FR1271043A (en) 1958-07-24 1959-07-20 Process for preparing sulfo-cyanic triazines
GB2532459A GB930594A (en) 1958-07-24 1959-07-23 A process for the production of thiocyanogen triazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED28588A DE1111641B (en) 1958-07-24 1958-07-24 Process for the preparation of rhodantriazines

Publications (1)

Publication Number Publication Date
DE1111641B true DE1111641B (en) 1961-07-27

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Family Applications (1)

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DED28588A Pending DE1111641B (en) 1958-07-24 1958-07-24 Process for the preparation of rhodantriazines

Country Status (3)

Country Link
CH (1) CH387645A (en)
DE (1) DE1111641B (en)
GB (1) GB930594A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1217965B (en) * 1965-02-10 1966-06-02 Bayer Ag Process for the preparation of trisubstituted s-triazines
EP0433616A2 (en) * 1989-12-22 1991-06-26 Degussa Aktiengesellschaft Use of heterocyclic thiocyanates as microbicides and agents containing such microbicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH314915A (en) * 1952-06-18 1956-07-15 Ciba Geigy Process for the preparation of 2-thiocyano-4: 6-diamino-s-triazine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH314915A (en) * 1952-06-18 1956-07-15 Ciba Geigy Process for the preparation of 2-thiocyano-4: 6-diamino-s-triazine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1217965B (en) * 1965-02-10 1966-06-02 Bayer Ag Process for the preparation of trisubstituted s-triazines
EP0433616A2 (en) * 1989-12-22 1991-06-26 Degussa Aktiengesellschaft Use of heterocyclic thiocyanates as microbicides and agents containing such microbicides
EP0433616A3 (en) * 1989-12-22 1993-03-03 Degussa Aktiengesellschaft Use of heterocyclic thiocyanates as microbicides and agents containing such microbicides

Also Published As

Publication number Publication date
CH387645A (en) 1965-02-15
GB930594A (en) 1963-07-03

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