DD209814A1 - METHOD FOR PRODUCING SUBSTITUTED N-NITRO-AMIDINO-ISOTHIOSEMICARBAZIDES - Google Patents

Abstract

The present invention relates to a process for the preparation of hitherto unknown substituted N-nitro-amidino-isothiosemicarbaziden. The representatives of this class of substances claim increased interest as potential biocides. As starting materials for the synthesis of various heterocyclic compounds, they also have great importance. The aim of the invention is to allow a simple synthesis of a variety of these interesting compounds. The object is achieved in that N-nitro-amidino-dithiocarbimidesaeurediester with any asymmetrically disubstituted hydrazines in polar solvents, preferably alcohols having 1 to 4C atoms, at 20 degrees C to 120 degrees C to the substituted N-nitro-amidino-isothiosemicarbaziden be implemented.

Description

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Title of the invention

Process for the preparation of substituted N-nitro-amidinoisothiosemicarbazides

Field of application of the invention

The invention relates to a process for the preparation of clay-substituted H-Mtro-ainidino-isothiosemicarbaziden · The biocidal activity of various Thiosemioarbazidderivate is well known · The present substance class is due to the combination of Ieothiosemicarbazidstruktur with the Nitramingruppierung special interest from the plant protection to · Beyond the representatives this class of substances as reactive starting materials for the synthesis of various hetero-cyclic compounds of importance.

Characteristic of the known technical solutions

The class of H-nitro-amidino-isothiosemicarbazide has not previously been described in the patent and technical literature. The numerous methods for the preparation of various representatives of isothiosemicarbazides do not allow a subsequent introduction of the kitro-amidino or nitro group.

Object of the invention

The aim of the invention is to make it possible by means of a suitable process to obtain the hitherto unknown substituted N-amido-isothiosemicarbazides.

By using inexpensive, technically available or easily accessible starting materials, the process is intended to produce a large number of substituted H-nitro-amidino derivatives in a simple manner.

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Isothiosemicarbazlden with any substituent pattern lead «

Explanation of the essence of the invention

The object is achieved in that N-nitro-amidino-dithiocarbimidesäurediester of formula 1, in which E is branched or unbranched, substituted or unsubstituted alkyl radicals having 1 to 4 carbon atoms or · substituted or unsubstituted benzyl radicals, with asymmetrically disubstituted hydra -

p "Z

zinen of formula 2 ₉ in the B and R-, same or different, branched or unbranched, substituted or unsubstituted alkyl radicals or »substituted or unsubstituted benzyl radicals or substituted or unsubstituted phenyl radicals, to the substituted N-nitro-amidino-isothiosemlcarbaziden the Formula J5, ^ ^{11 of} E, E ^fc and R ^y have the meaning above, be implemented »

NH ₂ E ² y ^ Z E ²

^ E ¹ + H ₂ N < ₃ ONNO ** <

^X N «C ^ ^R

The reactions are carried out at temperatures between 20 ^° C. and 120 ^° C. in polar solvents, preferably alcohols having 1 to 4 carbon atoms. The reaction products are already obtained during the reaction as crystalline products in high purity from alcohol or optionally from DMF / ethanol possible *

The advantage of the invention is the simple, direct synthesis in good yields "It leads to a large number of biologically and synthetically interesting compounds using cheap, technically leiht available starting materials,

The invention is illustrated by exemplary embodiments, without being limited to «

embodiment

1 · N ¹ - (H-nitro-ainidino) -Ii ⁴ '-metliyl-H ⁴ --plienyl - S-metlayl-.iso1; LILO

semicarbazide

O ₉ 02 mol of N-nitro-amidino-ditMocarbimidsäuredimethylester be boiled with 0.02 mol of N-methyl-N-phenyl-hydrazine in 40 ml of ethanol until the end of Methylmercaptanentwicklung · The precipitated after cooling the reaction solution crystals are filtered off with suction and to further Purification from DMP / ethanol recrystallized. · Pp .: 164 ^° C. Yield: 41 $> d. Th. (2.3 g)

2 · K- (H-nitro-amidino) -N ^ ", N-dimethyl-S-methylisothiosemi

carbazide

0.02 mol of N-nitro-amidino-dithiocarbimic acid dimethyl ester in 40 ml of ethanol are mixed with 0.02 mol of H, H-dimethylhydrazine and stirred at 60 ^° C. for two hours. After the reaction has subsided, the mixture is refluxed for a further 30 minutes. The solution is concentrated to half the volume and the crystals which precipitate are filtered off with suction. The substance is purified by recrystallization from ethanol · · Pp: 148 ⁰ C. Yield: 71 # _e d Th (3 # 2 g)

Claims (2)

242567 Γ Pat addressed 1 · A process for the preparation of substituted N-nitro-amidino-isothiosemicarbaziden of the formula %, in which R is a substituted or unsubstituted, branched or unbranched alkyl radical having 1 to 4 carbon atoms or * a substituted or unsubstituted benzyl radical stent _f R and R _{9 are} identical or different, represent substituted or unsubstituted, branched or unbranched alkyl radicals or · substituted or unsubstituted benzyl radicals or · substituted or unsubstituted phenyl radicals, characterized in that N-amidino-ditMocarbimidesäurediester of formula J _- , in which R has the above meaning , with asymmetrically substituted hydrazines of the formula 2 in which R and R- * have the above meaning, are reacted * 2 «method according to item 1 ·, characterized in that the reactions at temperatures between 20 ⁰ C and 120 ⁰ C in polar solvents, preferably in alcohols having 1 to 4 carbon atoms, are performed»