DE1118206B - Process for the preparation of fluorinated s-triazine derivatives - Google Patents
Process for the preparation of fluorinated s-triazine derivativesInfo
- Publication number
- DE1118206B DE1118206B DEG29612A DEG0029612A DE1118206B DE 1118206 B DE1118206 B DE 1118206B DE G29612 A DEG29612 A DE G29612A DE G0029612 A DEG0029612 A DE G0029612A DE 1118206 B DE1118206 B DE 1118206B
- Authority
- DE
- Germany
- Prior art keywords
- triazine
- bis
- fluorinated
- fluoride
- fluoro
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon 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
-
- 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
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
G29612IVd/12pG29612IVd / 12p
BEKANNTMACHUNG DER ANMELDUNG UNDAUSGABEDER AUSLEGESCHRIFT: 30. NOVEMBER 1961NOTICE THE REGISTRATION ANDOUTPUTE EDITORIAL: NOVEMBER 30, 1961
Die Erfindung betrifft ein neues, verbessertes und eigenartiges Verfahren zur Herstellung von fluorierten s-Triazinderivaten.The invention relates to a new, improved and unique process for the preparation of fluorinated s-triazine derivatives.
Es ist bekannt, daß man Cyanurchlorid durch Erhitzen mit mindestens 3 Mol Kaliumfluorid oder einem anderen geeigneten Fluorid in Gegenwart einer Antimonverbindung, z. B. Antimonpentoxyd oder Antimonpentachlorid, in Cyanurfluorid überführen kann. Die Umsetzung des Cyanurfluorids mit 1 oder 2 Mol von Hydroxylverbindungen, Mercaptoverbindüngen oder aromatischen Aminen zu 2-substituierten 4,6-Difluor-s-triazinen bzw. 2,4-disubstituierten 6-Fluor-s-triazinen ist ebenfalls bekannt. Ferner ist auch schon die Umsetzung des Cyanurfluorids mit 1 Mol eines aliphatischen Amins zu einem 2-substituierten 4,6-Difluor-s-triazin beschrieben worden. Hingegen ist die Herstellung von 2,4-diaminosubstituierten 6-Fluor-s-triazinen durch Umsetzung von Cyanurfluorid mit 2 Mol eines aliphatischen Amins bisher nicht im einzelnen beschrieben'worden.It is known that cyanuric chloride by heating with at least 3 moles of potassium fluoride or another suitable fluoride in the presence of an antimony compound, e.g. B. antimony pentoxide or Antimony pentachloride, can be converted into cyanuric fluoride. The implementation of the cyanuric fluoride with 1 or 2 moles of hydroxyl compounds, mercapto compounds or aromatic amines to form 2-substituted ones 4,6-Difluoro-s-triazines and 2,4-disubstituted 6-fluoro-s-triazines are also known. Furthermore is even the implementation of cyanuric fluoride with 1 mole of an aliphatic amine to form a 2-substituted one 4,6-difluoro-s-triazine has been described. In contrast, the production of 2,4-diamino-substituted ones 6-fluoro-s-triazines by reacting cyanuric fluoride with 2 moles of an aliphatic amine so far not described in detail.
Überraschenderweise wurde nun gefunden, daß man unter Vermeidung der Herstellung des äußerst unangenehm zu handhabenden Cyanurfluorids zu neuen Verbindungen der allgemeinen Formel Verfahren zur Herstellung von fluorierten s-TriazinderivatenSurprisingly, it has now been found that, while avoiding the production of the extremely unpleasant cyanuric fluoride to be handled to form new compounds of the general formula Process for the preparation of fluorinated s-triazine derivatives
Anmelder: J. R. Geigy A.-G., Basel (Schweiz)Applicant: J. R. Geigy A.-G., Basel (Switzerland)
Vertreter: Dr. F. Zumstein,Representative: Dr. F. Zumstein,
Dipl.-Chem. Dr. rer. nat. E. Assmann.Dipl.-Chem. Dr. rer. nat. E. Assmann.
und Dipl.-Chem. Dr. R. Koenigsberger,and Dipl.-Chem. Dr. R. Koenigsberger,
Patentanwälte, München 2, Bräuhausstr. 4Patent Attorneys, Munich 2, Bräuhausstr. 4th
Beanspruchte Priorität: Schweiz vom 6. Mai 1959 (Nr. 72 981)Claimed priority: Switzerland of May 6, 1959 (No. 72 981)
Dr. Enrico Knüsli, Riehen, Dr. Walter Stambach und Dr. Hans Gysin,Dr. Enrico Knüsli, Riehen, Dr. Walter Stambach and Dr. Hans Gysin,
Basel (Schweiz), sind als Erfinder genannt wordenBasel (Switzerland) have been named as the inventor
N NN N
-n:-n:
worin R1, R2 und R3 Wasserstoff, gleiche oder verschiedene niedermolekulare Alkyl-, Alkenyl- oder Alkoxyalkylreste oder Aralkylreste und R4 einen niedermolekularen Alkyl-, Alkenyl- oder Alkoxyalkylrest oder einen Aralkylrest bedeuten, wobei Alkylreste R1 und R2 bzw. R3 und R4 auch unter sich direkt oder über ein Sauerstoffatom verbunden sein können, gelangen kann, wenn man Verbindungen der allgemeinen Formelwherein R 1 , R 2 and R 3 are hydrogen, identical or different low molecular weight alkyl, alkenyl or alkoxyalkyl radicals or aralkyl radicals and R 4 is a low molecular weight alkyl, alkenyl or alkoxyalkyl radical or an aralkyl radical, where alkyl radicals R 1 and R 2 or R 3 and R 4 can also be connected directly to one another or via an oxygen atom, if one uses compounds of the general formula
ClCl
J \Y \
N NN N
i Ii N—c c—n;i ii N-c c-n;
IIII
R4 worin R1 bis R4 die oben angegebene Bedeutung haben, mit mindestens einem Normaläquivalent eines neutralen Salzes der Fluorwasserstoffsäure in An- oder Abwesenheit von inerten organischen Lösungsmitteln erhitzt. Bei diesem Verfahren wird nicht nur die Belästigung und Vergiftungsgefahr durch das gegenüber Wasser eine viel geringere Beständigkeit als Cyanurchlorid aufweisende Cyanurfluorid vermieden, sondern das neue Verfahren besitzt auch große wirtschaftliche Vorteile, insbesondere deshalb, weil bei der Umsetzung keine fluorwasserstoffbeständigen Apparaturen benötigt werden. Ferner ist beim erfindungsgemäßen Verfahren der Gesamtaufwand an umzusetzenden Fluorsalzen, z. B.R 4 wherein R 1 to R 4 have the meaning given above, heated with at least one normal equivalent of a neutral salt of hydrofluoric acid in the presence or absence of inert organic solvents. This process not only avoids the nuisance and risk of poisoning caused by the cyanuric fluoride, which is much less resistant to water than cyanuric chloride, but the new process also has great economic advantages, in particular because no hydrogen fluoride-resistant equipment is required for the implementation. Furthermore, in the process according to the invention, the total expenditure on fluorine salts to be converted, eg. B.
Kaliumfluorid, auf einen Bruchteil, d. h. auf ein Drittel, verringert.Potassium fluoride, to a fraction, i.e. H. reduced to a third.
Als neutrale Fluoride können z. B. Kaliumfluorid, Natriumfluorid, Ammoniumfluorid, Calciumfluorid,
Zinkfluorid, Antimon(III)-fluorid sowie auch Gemische mehrerer der obigen Salze verwendet werden. Man verwendet
zur Herstellung der Endstoffe ein Normaläquivalent oder einen beliebigen Überschuß an neutralem
Fluorsalz.
Die für den Eintritt der Umsetzung nötige Temperatür kann in weiten Grenzen variieren, z. B. zwischen
100 und 200° C. Der Reaktionsverlauf kann z. B. an Hand von kleinen Proben leicht durch ArgentometrieAs neutral fluorides, for. B. potassium fluoride, sodium fluoride, ammonium fluoride, calcium fluoride, zinc fluoride, antimony (III) fluoride and also mixtures of several of the above salts can be used. A normal equivalent or any excess of neutral fluorine salt is used to prepare the end products.
The temperature required for the implementation to take place can vary within wide limits, e.g. B. between 100 and 200 ° C. The course of the reaction can, for. B. on the hand of small samples easily by argentometry
109 747/546109 747/546
der beim Austausch der Halogenatome freigesetzten Chlorionen verfolgt werden; auf diese Weise können die für jeden speziellen Ausgangsstoff benötigte Reaktionstemperatur und Reaktionsdauer ermittelt werden, welch letztere je nach Reaktionstemperatur zwischen 12 und 100 Stunden betragen kann. Vorzugsweise wird die Umsetzung in geeigneten höhersiedenden, inerten organischen Lösungsmitteln, insbesondere in Dimethylformamid, oder gegebenenfalls auch in Äthylenglykoldiäthyläther oder Diäthylenglykoldiäthyläther durchgeführt; diese Lösungsmittel kann man gegebenenfalls während der Reaktion teilweise oder gänzlich abdestillieren. Man kann die Umsetzung auch in Anwesenheit geeigneter Katalysatoren durchführen.the chlorine ions released when the halogen atoms are exchanged are monitored; this way you can the reaction temperature required for each particular starting material and reaction time can be determined, the latter depending on the reaction temperature between Can be 12 and 100 hours. The reaction is preferably carried out in suitable, relatively high-boiling, inert ones organic solvents, especially in dimethylformamide, or optionally also in ethylene glycol diethyl ether or diethylene glycol diethyl ether carried out; these solvents can optionally be used partially or completely distill off during the reaction. You can also do the implementation in attendance carry out suitable catalysts.
Die erfindungsgemäß erhältlichen substituierten 6-Fluor-s-triazine der allgemeinen Formel I sind vielseitig verwendbare Produkte mit teilweise sehr interessanten biologischen Eigenschaften, die ihre Verwendung z. B. als Mittel zur Hemmung des Pflanzenwachstums ermöglichen.The substituted 6-fluoro-s-triazines of the general formula I obtainable according to the invention are versatile usable products with partly very interesting biological properties that make their use z. B. as a means of inhibiting plant growth.
Als Ausgangsstoffe der allgemeinen Formel II kommen beispielsweise folgende Verbindungen in Frage: 2-Amino-4-äthylamino-, 2,4-Bis-methylarnino-, 2,4-Bisäthylamino-, 2,4-Bis-n-propylamino-, 2,4-Bis-isopropylamino-, 2-n-Propylamino-4-methylamino-, 2-Isopropylamino - 4 - methylamino -, 2 - Isopropylamino 4-äthylamino-, 2,4-Bis-n-butylamino-, 2,4-Bis-isobutylamino-, 2,4-Bis-(y-methoxy-propylamino)-, 2,4-Bis- (γ - isopropoxy - propylamino) -, 2 - (γ - Methoxy - pr opylammo)-4-äthylamino-, 2,4-Bis-allylamino-, 2,4-Bisbenzylamino-, 2-661^13111^10-4^1^^111^10-, 2-Diäthylamino-4-äthylamino-, 2-Diäthylamino-4-isopropylamino-, 2,4-Bis-diäthylamino-, 2,4-Bis-(N-äthylbenzylamino)-, 2,4-Bis-pyrrolidino-, 2,4-Bis-piperidino-, 2-Piperidino-4-äthylamino-, 2,4-Bis-morpholino-, 2-Morpholino-4-isopropylamino- und 2-Morpholino-4-methylamino-6-chlor-s-triazin. The following compounds, for example, can be used as starting materials of the general formula II: 2-amino-4-ethylamino, 2,4-bis-methylamino, 2,4-bisethylamino, 2,4-bis-n-propylamino, 2 , 4-bis-isopropylamino-, 2-n-propylamino-4-methylamino-, 2-isopropylamino - 4 - methylamino -, 2 - isopropylamino, 4-ethylamino, 2,4-bis-n-butylamino, 2,4 -Bis-isobutylamino-, 2,4-bis- (γ-methoxy-propylamino) -, 2,4-bis- (γ- isopropoxy-propylamino) -, 2 - (γ- methoxy-propylammo) -4-ethylamino -, 2,4-bis-allylamino-, 2,4-bisbenzylamino-, 2-661 ^ 13111 ^ 10-4 ^ 1 ^^ 111 ^ 10-, 2-diethylamino-4-ethylamino, 2-diethylamino-4 -isopropylamino-, 2,4-bis-diethylamino-, 2,4-bis- (N-ethylbenzylamino) -, 2,4-bis-pyrrolidino-, 2,4-bis-piperidino-, 2-piperidino-4- ethylamino-, 2,4-bis-morpholino-, 2-morpholino-4-isopropylamino- and 2-morpholino-4-methylamino-6-chloro-s-triazine.
Die nachfolgenden Beispiele sollen die Durchführung des erfindungsgemäßen Verfahrens näher erläutern. Teile bedeuten darin Gewichtsteile, diese verhalten sich zu Volumteilen wie Gramm zu Kubikzentimeter.The following examples are intended to implement explain the method according to the invention in more detail. Parts mean parts by weight, these are related to parts by volume as grams to cubic centimeters.
50 Teile 2,4-Bis-äthylamino-6-chlor-s-triazin werden mit 40 Teilen Kaliumfluorid in 500 Volumteilen Dimethylformamid 96 Stunden unter Rückfluß gekocht. Darauf gießt man das Reaktionsgemisch in 2000 Teile Wasser und nutscht das ausgefallene rohe 2,4-Bisäthylamino-6-fluor-s-triazin ab. Es kann z. B. durch Umkristallisation aus Dioxan gereinigt werden und schmilzt darauf bei 223 bis 224° C50 parts of 2,4-bis-ethylamino-6-chloro-s-triazine are mixed with 40 parts of potassium fluoride in 500 parts by volume of dimethylformamide Boiled under reflux for 96 hours. The reaction mixture is then poured into 2000 parts Water and sucks the precipitated crude 2,4-bisethylamino-6-fluoro-s-triazine away. It can e.g. B. can be purified by recrystallization from dioxane and then melts at 223 to 224 ° C
Aus der wäßrigen Phase fällt beim Versetzen mit Silbernitratlösung die der quantitativen Umsetzung entsprechende Menge Silberchlorid aus. Gewünschtenfalls kann ein Teil des Dimethylformamids im Verlaufe der Reaktion abdestilliert werden, um die aus der wäßrigen Phase zurückzugewinnende Menge zu verringern. The quantitative conversion falls from the aqueous phase when silver nitrate solution is added corresponding amount of silver chloride. If desired, some of the dimethylformamide can be used in the course distilled off the reaction in order to reduce the amount to be recovered from the aqueous phase.
61 Teile 2-Isoproρylamino-4-diäthylamino-6-chlors-triazin werden mit 40 Teilen Kaliumfluorid in 500 Volumteilen Dimethylformamid 96 Stunden unter Rückfluß gekocht. Darauf wird das Lösungsmittel im Vakuum abdestilliert und der in Äther aufgenommene Rückstand mit Wasser gewaschen. Die Rektifikation der Ätherlösung ergibt das gewünschte 2-Isopropylamino-4-diäthylamino-6-fluor-s-triazin, das unter 0,2 mm bei 108 bis IH0C siedet. Beim Abkühlen erstarrt das Produkt und weist einen Schmelzpunkt von 80 bis 84° C auf.61 parts of 2-isopropylamino-4-diethylamino-6-chloros-triazine are refluxed for 96 hours with 40 parts of potassium fluoride in 500 parts by volume of dimethylformamide. The solvent is then distilled off in vacuo and the residue taken up in ether is washed with water. The rectification of the ether solution gives the desired 2-isopropylamino-4-diethylamino-6-fluoro-s-triazine, mm under 0.2 to boiling IH 0 C at 108th The product solidifies on cooling and has a melting point of 80 to 84 ° C.
In analoger Weise erhält man unter Verwendung der entsprechend substituierten 6-Chlor-s-triazine das 2,4-Bis-isopropylamino-6-fluor-s-triazin (F. = 218 bis 2200C), das 2-Isopropylamino-4-methylamino-6-fluors-triazin (F. = 166 bis 1680C), das 2-Isopropylamino-4-äthylamino-6-fluor-s-triazin (F. = 186 bis 1870C)9 das 2,4-Bis-diäthylamino-6-fluor-s-triazin (Kp.0Jl = 104 bis 1060C), das 2-Diäthylamino-4-äthylamino-6-fluor-s-triazin· (Κρ.ο,οβ = 900C), das 2-n-Propylamino-4-methylamino-6-fluor-s-triazin (F. = 180 bis 182° C), das 2-(y-Methoxy-propylamino)-4-äthylamino-6-fluor-s-triazin (F. = 130 bis 132° C), das 2-Morpholino-4-isopropylamino-6-fluor-s-triazin (F. = 130 bis 132° C), das 2,4-Bis-piperidino-6-fiuor-s-triazin (F. = 110 bis 12O0C) und das 2-Benzylamino-4-äthylamino-6-fluor-s-triazin (F. = 184 bis 1860C).Using the correspondingly substituted 6-chloro-s-triazines, 2,4-bis-isopropylamino-6-fluoro-s-triazine (mp = 218 to 220 ° C.), 2-isopropylamino-4, is obtained in an analogous manner methylamino-6-fluoros-triazine (F. = 166 to 168 0 C), the 2-isopropylamino-4-ethylamino-6-fluoro-s-triazine (F. = 186 to 187 0 C) 9 the 2.4 -Bis-diethylamino-6-fluoro-s-triazine ( b.p. 0Jl = 104 to 106 0 C), the 2-diethylamino-4-ethylamino-6-fluoro-s-triazine (Κρ.ο, οβ = 90 0 C), 2-n-propylamino-4-methylamino-6-fluoro-s-triazine (temperature = 180 to 182 ° C), 2- (γ-methoxypropylamino) -4-ethylamino-6-fluoro -s-triazine (mp = 130 to 132 ° C), the 2-morpholino-4-isopropylamino-6-fluoro-s-triazine (mp = 130 to 132 ° C), the 2,4-bis-piperidino -6-fluor-s-triazine (F. = 110 to 12O 0 C) and the 2-benzylamino-4-ethylamino-6-fluoro-s-triazine (M. = 184 to 186 0 C).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7298159A CH376926A (en) | 1959-05-06 | 1959-05-06 | Process for the preparation of fluorinated s-triazines and their use for inhibiting the growth of plants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1118206B true DE1118206B (en) | 1961-11-30 |
Family
ID=4532261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG29612A Pending DE1118206B (en) | 1959-05-06 | 1960-05-05 | Process for the preparation of fluorinated s-triazine derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH376926A (en) |
| DE (1) | DE1118206B (en) |
| GB (1) | GB950851A (en) |
| NL (1) | NL251221A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464625B (en) * | 2010-11-03 | 2014-07-02 | 中国中化股份有限公司 | Fluorotriazine compound with herbicidal activity and its preparation method |
-
0
- NL NL251221D patent/NL251221A/xx unknown
-
1959
- 1959-05-06 CH CH7298159A patent/CH376926A/en unknown
-
1960
- 1960-05-04 GB GB1570860A patent/GB950851A/en not_active Expired
- 1960-05-05 DE DEG29612A patent/DE1118206B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH376926A (en) | 1964-04-30 |
| GB950851A (en) | 1964-02-26 |
| NL251221A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1229102B (en) | Process for the preparation of monochloro-9-thiabicyclo-2-nonenes and their 9-oxides and 9,9-dioxides | |
| DE1118206B (en) | Process for the preparation of fluorinated s-triazine derivatives | |
| DD140041B1 (en) | METHOD FOR THE PRODUCTION OF LONG-CHAINED N-ALKYLDIMETHYLMORPHOLINES | |
| DE2627223C2 (en) | ||
| DE1300117B (en) | 5-sulfonyl-1,2-dithiol-3-ones | |
| DE1670920A1 (en) | N-Disubstituted 3-amino-1,2-benzisothiazole derivatives | |
| DE941193C (en) | Process for the production of new, bisquaterner phosphonium compounds | |
| DE1670196C3 (en) | Process for the preparation of 1,2-benzisothiazoles | |
| DE919350C (en) | Process for the preparation of poly-bis-thiuram disulfides | |
| AT265286B (en) | Process for the production of new sulfonamides | |
| DE2360248C3 (en) | Process for the preparation of esters of thiol carbamic acids | |
| DE1768003C3 (en) | Process for the preparation of novel chlorosulfenylphenyl isocyanide dichlorides | |
| DE975041C (en) | Process for the preparation of sulfonamide derivatives of pyrimidine | |
| DE721724C (en) | Process for the preparation of asymmetric thiuram monosulfides | |
| DE875048C (en) | Process for the preparation of 3-pyrazolidones | |
| DE1129484B (en) | Process for the simultaneous production of substituted thioamides and thiophosphorus - (- one, -in) acid halides | |
| DE1445008C (en) | Process for the preparation of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxydes. Eliminated from: 1112079 | |
| DE1927529C3 (en) | Process for the preparation of mono- and biscarbodiimides | |
| DE933755C (en) | Process for the preparation of derivatives of tetrahydro-ª † -carboline | |
| DE1101407B (en) | Process for the preparation of sulfonic acid amide-N-sulfenic acid chlorides | |
| DE1222068B (en) | Process for the preparation of trisubstituted 1, 2, 4-triazoles | |
| DE1100030B (en) | Process for the preparation of heterocyclic compounds | |
| DE1063155B (en) | Process for the preparation of thiophosphoric acid esters | |
| DE1793287B2 (en) | METHOD FOR PREPARING N-SUBSTITUTED N-ACYLCARBAMIC ACID HALOGENIDES | |
| DE1088962B (en) | Process for the preparation of N-substituted pyrrolidines, their salts and quaternary ammonium compounds |