DE1220429B - Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines - Google Patents

Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines

Info

Publication number
DE1220429B
DE1220429B DED43437A DED0043437A DE1220429B DE 1220429 B DE1220429 B DE 1220429B DE D43437 A DED43437 A DE D43437A DE D0043437 A DED0043437 A DE D0043437A DE 1220429 B DE1220429 B DE 1220429B
Authority
DE
Germany
Prior art keywords
benzyl
mol
thiadiazines
carboxyalkyl
tetrahydro
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
DED43437A
Other languages
German (de)
Inventor
Dipl-Chem Wolfgang Schade
Dr Alfred Rieche
Dr Anna-Elisabeth Martini
Dr Dieter Martin
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.)
Akademie der Wissenschaften der DDR
Original Assignee
Akademie der Wissenschaften der DDR
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 Akademie der Wissenschaften der DDR filed Critical Akademie der Wissenschaften der DDR
Priority to DED43437A priority Critical patent/DE1220429B/en
Publication of DE1220429B publication Critical patent/DE1220429B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • C07D285/34—1,3,5-Thiadiazines; Hydrogenated 1,3,5-thiadiazines

Description

Verfahren zur Herstellung von 2-Thio-3-benzyl-5-carboxyalkyl-tetrahydro-1 ,3,5-thiadiazinen Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3,5-thiadiazinen der allgemeinen Formel in der n die Zahlen 1 oder 2 bedeutet, das dadurch gekennzeichnet ist, daß man in an sich bekannter Weise Benzylamin mit Schwefelkohlenstoff und einem Alkali- oder Erdalkalihydroxyd umsetzt und anschließend 1 Mol des erhaltenen N-benzyl-dithiocarbamidsauren Salzes mit 2 Mol Formaldehyd, 1 Mol Glycin oder p-Alanin und 1 Mol Säure zur Reaktion bringt.Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3,5-thiadiazines The invention relates to a process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3 , 5-thiadiazines of the general formula in which n denotes the numbers 1 or 2, which is characterized in that benzylamine is reacted in a manner known per se with carbon disulfide and an alkali or alkaline earth metal hydroxide and then 1 mole of the resulting N-benzyl-dithiocarbamic acid salt with 2 moles of formaldehyde, 1 Moles glycine or p-alanine and 1 mole acid reacts.

Diese Verbindungen sind bakteriostatisch und fungistatisch wirksam. These compounds are bacteriostatic and fungistatic.

Verbindungen der allgemeinen Formel in der R und R' voneinander verschiedene, gegebenenfalls substituierte aliphatische, cycloaliphatische araliphatische oder aromatische Reste bedeuten, sind bereits beschrieben.Compounds of the general formula in which R and R 'denote optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radicals which are different from one another have already been described.

Sie werden hergestellt, indem man Dithiocarbamate, deren NH2-Gruppe primär den Substituenten R (bzw. R') trägt, mit mineralsauren Salzen von Aminoverbindungen, die primär den Substituenten R' (bzw. R) tragen, und Formaldehyd umsetzt (österreichische Patentschrift 213 900). They are made by taking dithiocarbamates, their NH2 group primarily carries the substituent R (or R '), with mineral acid salts of amino compounds, which primarily carry the substituent R '(or R) and converts formaldehyde (Austrian Patent 213,900).

Diese Verbindungen sollen sich als Schädlingsbekämpfungsmittel und zur Bekämpfung von Nematoden und Pilzen im Ackerboden eignen. These compounds are said to be useful as pesticides and Suitable for combating nematodes and fungi in arable soil.

Die erfindungsgemäß herstellbaren 2-Thio-3-benzyl-5-carboxyalkyl-tetrahydro- 1 ,3,5-thiadiazine hemmen besonders gut das Wachstum pathogener Hautpilze. Sie sind gut kristalline, farblose, beständige und wenig toxische Verbindungen. In Form ihrer Alkalisalze sind sie gut wasserlöslich. Aus einer Gegenüberstellung geht hervor, daß die Grenzkonzentrationen, bis zu denen das Wachstum pathogener Hautpilze (Mikrosporum gypseum) vollständig gehemmt wird, bei den erfindungsgemäß herstellbaren Verbindungen besonders niedrig sind. The 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3,5-thiadiazines which can be prepared according to the invention inhibit the growth of pathogenic skin fungi particularly well. They are good crystalline, colorless, stable and not very toxic compounds. In the form of their alkali salts, they are readily soluble in water. A comparison shows that the limit concentrations up to which the growth of pathogenic skin fungi (microsporum gypseum) is completely inhibited are particularly low in the case of the compounds which can be prepared according to the invention.

Hemmwerte der erfindungsgemäß herstellbaren Verbindungen R Schmelz- Hemmwerte punkt C6HsCH2 CH2COOH 1520C 1:5000000 C6HsCH2 CH2-CH2-COOH 146"C 1:5000000 Hemmwerte der bekannten Verbindungen R R' Schmelz- Hemmwerte punkt CsH5CH2 C6HsCH2 102"C 1:100000 CH3 CH2-COOH 138"C 1:500000 An Hand eines Beispiels sei das erfindungsgemäße Verfahren näher beschrieben.Inhibition values of the compounds which can be prepared according to the invention R enamel inhibition values Point C6HsCH2 CH2COOH 1520C 1: 5000000 C6HsCH2 CH2-CH2-COOH 146 "C 1: 5000000 Inhibition values of the known compounds RR 'enamel inhibition values Point CsH5CH2 C6HsCH2 102 "C 1: 100,000 CH3 CH2-COOH 138 "C1: 500,000 The method according to the invention will be described in more detail using an example.

Beispiel Zu einer Lösung von lilo Mol Soda in 100 cm3 Wasser wird 1/1o Mol Benzylamin und danach tropfenweise unter Rühren bei Zimmertemperatur 1/1o Mol Schwefelkohlenstoff zugesetzt. Anschließend werden 2/10 Mol Formalin als 250/oige Lösung zugegeben, etwas ausgeschiedenes DI durch Filtration abgetrennt und die klare Lösung mit 1/1o Mol Glycin bzw. p-Alanin, gelöst in 20 cm3 Wasser und 1/1o Mol Salzsäure, versetzt. Nach beendeter Zugabe wird mit verdünnter Salzsäure bis pH 5 angesäuert, 1/2 Stunde nachgerührt, das ausgeschiedene Produkt abgesaugt, mit Wasser gewaschen und aus Alkohol umkristallisiert. Die Ausbeuten betragen durchschnittlich 500/0. Example Becomes a solution of 100 moles of soda in 100 cm3 of water 1/10 mole of benzylamine and then 1/10 dropwise with stirring at room temperature Moles of carbon disulfide added. Then 2/10 moles of formalin are used as 250% Solution added, some DI separated off by filtration and the clear Solution with 1/10 mol glycine or p-alanine, dissolved in 20 cm3 water and 1/10 mol hydrochloric acid, offset. When the addition is complete, it is acidified with dilute hydrochloric acid to pH 5, Stirred for 1/2 hour, filtered off the precipitated product, washed with water and recrystallized from alcohol. The yields are on average 500/0.

Claims (1)

Patentanspruch: Verfahren zur Herstellung von 2-Thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3,5-thiadiazinen der allgemeinen Formel in der n die Zahlen 1 oder 2 bedeutet, d a -durch gekennzeichnet, daß man in an sich bekannter Weise Benzylamin mit Schwefelkohlenstoff und einem Alkali- oder Erdalkalihydroxyd umsetzt und anschließend 1 Mol des erhaltenen N-benzyl-dithiocarbamidsauren Salzes mit 2 Mol Formaldehyd, 1 Mol Glycin oder ß-Alanin und 1 Mol Säure zur Reaktion bringt.Claim: Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1,3,5-thiadiazines of the general formula in which n denotes the numbers 1 or 2, characterized in that, in a manner known per se, benzylamine is reacted with carbon disulfide and an alkali or alkaline earth metal hydroxide and then 1 mol of the resulting N-benzyl-dithiocarbamic acid salt with 2 mol of formaldehyde, 1 Brings mol glycine or ß-alanine and 1 mol acid to the reaction. In Betracht gezogene Druckschriften: Osterreichische Patentschrift Nr. 213 900. Publications considered: Austrian Patent Specification No. 213 900.
DED43437A 1962-03-26 1962-03-26 Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines Pending DE1220429B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED43437A DE1220429B (en) 1962-03-26 1962-03-26 Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED43437A DE1220429B (en) 1962-03-26 1962-03-26 Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines

Publications (1)

Publication Number Publication Date
DE1220429B true DE1220429B (en) 1966-07-07

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Application Number Title Priority Date Filing Date
DED43437A Pending DE1220429B (en) 1962-03-26 1962-03-26 Process for the preparation of 2-thio-3-benzyl-5-carboxyalkyl-tetrahydro-1, 3, 5-thiadiazines

Country Status (1)

Country Link
DE (1) DE1220429B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2410558A1 (en) * 1974-03-06 1975-09-11 Schuelke & Mayr Gmbh TETRAHYDROTHIADIAZINTHIONS, METHOD OF MANUFACTURING THEREOF AND USING THEM AS ANTIMICROBIAL AGENTS

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT213900B (en) * 1957-08-10 1961-03-10 Bayer Ag Process for the preparation of new derivatives of tetrahydrothiamidine thione

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT213900B (en) * 1957-08-10 1961-03-10 Bayer Ag Process for the preparation of new derivatives of tetrahydrothiamidine thione

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2410558A1 (en) * 1974-03-06 1975-09-11 Schuelke & Mayr Gmbh TETRAHYDROTHIADIAZINTHIONS, METHOD OF MANUFACTURING THEREOF AND USING THEM AS ANTIMICROBIAL AGENTS

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