DE19843334A1 - New organosulfinic acid and organosulfonic acid derivatives useful in medicine against viral, bacterial, fungal and parasiticidal infections and as herbicides, plant fungicides and plant bactericides - Google Patents

Abstract

Hydroxyamino substituted organosulfinic acid and organosulfonic acid derivatives are new. Pharmaceutical preparations containing compounds (I) and a broad range of other pharmaceutically active substances are also new.

Description

The invention relates to organic sulfur compounds and theirs re salts, esters and amides and their use in therapy table and prophylactic treatment of infections Humans and animals caused by viruses, bacteria, fungi and parasites and their use as a fungicide, Bactericide and herbicide in plants. According to the invention the organic sulfur compounds sulfinic acid derivatives and Sulfonic acid derivatives.

There is a strong need to enrich the Be action of humans and animals as well as the protection of plants Provide funds that are not just powerful own, but unlike other medicines or pesticides show reduced side effects or cause less environmental pollution and thus a mean less danger to human health.

The object of the present invention is therefore a substance to provide universal for virus infections, Bacteria, fungi and parasites in humans and animals and as Fungicide, bactericide and herbicide can be used in plants and meets the above conditions.

This task is accomplished in a completely surprising way by the in Claim 1 defined substance group solved. This group of substances shows both an anti-infectious effect against viruses, bacteria,  Fungi, single and multicellular parasites as well as a fungi cidal, bactericidal and herbicidal activity in plants.

The organic sulfur compounds according to the invention correspond to the general formula (I):

wherein R ₃ is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted aralkyl , substituted and unsubstituted alkenyl with up to 26 carbon atoms, substituted and unsubstituted alkynyl with up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, halogen OX ₃ and NX ₄ X ₅ ,
wherein X ₃ is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl with up to 26 carbon atoms, substituted and unsubstituted alkynyl with up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, a silyl, a cation of an organic and inorganic base, in particular a metal of the first, second or third main group of the periodic table, ammonium, substituted ammonium and ammonium compounds derived from ethylenediamine or amino acids,
and X ₄ and X _{5 are the} same or different and are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radical and halogen,
where A is selected from the group consisting of

• a) from an alkylene radical, alkenylene radical, a hydroxyal kylenrest,
• b) from an alkylene amine residue, an alkenylene amine residue, a hydroxyalkylene amine residue, an alkylene imine residue, an alkenylene imine residue and a hydroxyalkylene imine residue, with a nitrogen atom present in the chain which connects the sulfur atom with the nitrogen atom of the group
  connects,
• c) from the ether group (IA)
  where A ₁ and A ₂ , of which A _{II2 can} also be omitted, are the same or different and are selected from the group consisting of alkylene radical, alkenylene radical and hydroxyalkylene radical,
• d) from the keto group (IB)
  wherein A ₃ and A ₄ , one or both of which can also be omitted, are the same or different, are selected from the group consisting of alkylene radical, alkenylene radical and hydroxyalkylene radical, and
• e) and from 5- and 6-membered cyclic, preferably heterocyclic, compounds which, apart from carbon, contain at least one heteroatom as a ring member, the heteroatom being selected from the group consisting of oxygen and nitrogen,
  consists of
  R ₁ are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radical, halogen and OX ₁ ,

where X ₁

are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted ized alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted Cy cloalkyl, substituted and unsubstituted aralkyl, substi exists and unsubstituted heterocyclic radical, and their pharmaceutically acceptable salts, esters and amides and salts of the esters.

Preferred compounds include compounds in which A is an amino group in which the nitrogen atom is not terminated is always present.

Preferred compounds are those of the formula

correspond, wherein R ₁ and X _{3 are} as defined for formula (I), and A is selected from the group consisting of CNC, C = NC, C-N = C, the carbon atoms having a hydroxyl or alkyl group up to 7 carbon atoms can be substituted.

Particularly preferred are compounds in which R ₁ is selected from the group consisting of acetyl and formyl, and X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and residues with 16 or 18 carbon atoms consists.

In particular, the compounds of the formula are also preferred

correspond, where R ₁ is selected from the group consisting of acetyl and formyl, Y and Z are each hydrogen, A _II1 is selected from the group consisting of methylene, ethylene, ethenylene, 2-hydroxypropylene and hydroxyethylene, and X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and residues with 16 or 18 carbon atoms.

The chain -A ₁ -OC (ZY) - preferably consists of one oxygen atom and two or three carbon atoms (not including substituents), particularly preferably two carbon atoms.

Also preferred are the compounds of the formula

correspond, wherein R ₁ is selected from the group consisting of acetyl and formyl, A ₃ is selected from the group consisting of methylene, ethylene, ethenylene, 2-hydroxypropylene, Hy droxymethylene and hydroxyethylene, A ₄ is omitted or methylene and X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl, and radicals having 16 and 18 carbon atoms.

The chain -A ₁ -CO-A ₂ - preferably consists of two to four carbon atoms (not including substituents), particularly preferably three carbon atoms.

In the compounds in which A in formula (I) represents a He terocycle, the amino group and the sulfur atom can be bound to any C atoms of the ring. However, preference is given to compounds in which they are bonded to two carbon atoms which are separated from one another only by a hetero atom. The following compounds are particularly preferred:

where R ₁ is selected from the group consisting of aceayl and formyl, and X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and radicals having 16 and 18 carbon atoms.

Peculiarities of the above definitions and suitable examples for this are given below:

"Acyl" is a substituent derived from an acid, such as of an organic carboxylic acid, carbonic acid, carbamic acid or those corresponding to the individual acids above Thioic acid or imidic acid, or from an organic sulfone acid, these acids each being aliphatic, aromatic and / or heterocyclic groups in the molecule include and Carbamoyl or carbamimidoyl.

Suitable examples of these acyl groups are shown below specified.

Aliphatic acyl groups are acyl radicals derived from an aliphatic acid, which include the following:
Alkanoyl (e.g. formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl etc.);
Alkenoyl (e.g. acryloyl, methacryloyl, crotonoyl etc.);
Alkylthioalkanoyl (e.g. methylthioacetyl, ethylthioacetyl etc.) alkanesulfonyl (e.g. mesyl, ethanesulfonyl, propanesulfonyl etc.);
Alkoxycarbonyl (e.g. methoxycarbonyl, ethoxycarbonyl, propoxy carbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, etc.);
Alkyl carbamoyl (e.g. methyl carbamoyl etc.);
(N-alkyl) thiocarbamoyl (e.g. (N-methyl) thiocarbamoyl etc.);
Alkyl carbamimidoyl (e.g. methyl carbamimidoyl etc.);
Oxalo;
Alkoxalyl (e.g. methoxalyl, ethoxalyl, propoxalyl etc.).

In the above examples of aliphatic acyl groups the aliphatic hydrocarbon part, especially the Al kylgruppe or the alkane radical, optionally one or more suitable have substituents such as amino, halogen (e.g. fluorine, Chlorine, bromine etc.), hydroxy, hydroxyimino, carboxy, alkoxy (e.g. methoxy, ethoxy, propoxy etc.), alkoxycarbonyl, acylami no (e.g. benzyloxycarbonylamino etc.), acyloxy (e.g. acetoxy, Benzoyloxy etc.) and the like; as the preferred aliphatic Acyl radicals with such substituents are e.g. B. with amino, car boxy, amino and carboxy, halogen, acylamino or the like to name substituted alkanoyle.

Aromatic acyl radicals are those acyl radicals which derive from an acid having a substituted or unsubstituted aryl group, where the aryl group can include phenyl, toluyl, xylyl, naphthyl and the like; Suitable examples are given below:
Aroyl (e.g. benzoyl, toluoyl, xyloyl, naphthoyl, phthaloyl etc.);
Aralkanoyl (e.g. phenylacetyl etc.);
Aralkenoyl (e.g. cinnamoyl etc.);
Aryloxyalkanoyl (e.g. phenoxyacetyl etc.);
Arylthioalkanoyl (e.g. phenylthioacetyl etc.);
Arylaminoalkanoyl (e.g. N-phenylglycyl, etc.);
Arenesulfonyl (e.g. benzenesulfonyl, tosyl or toluenesulfonyl, naphthalenesulfonyl, etc.);
Aryloxycarbonyl (e.g. phenoxycarbonyl, naphthyloxycarbonyl, etc.);
Aralkoxycarbonyl (e.g. benzyloxycarbonyl etc.);
Arylcarbamoyl (e.g. phenylcarbamoyl, naphthylcarbamoyl etc.);
Arylglyoxyloyl (e.g. phenylglyoxyloyl etc.).

In the above examples of aromatic acyl radicals, the aromatic hydrocarbon part (in particular the aryl radical) and / or the aliphatic hydrocarbon part (in particular the alkane radical) can optionally have one or more suitable substituents, such as those which are suitable substituents for the alkyl group or the alkane residue has already been given. In particular and as an example of preferred aromatic acyl radicals with special substituents, arylanoyl substituted with halogen and hydroxy or with halogen and acyloxy and aralkanoyl substituted with hydroxy, hydroxyimino, dihalogenalkanoyloxyimino are also given
Arylthiocarbamoyl (e.g. phenylthiocarbamoyl etc.);
Arylcarbamimidoyl (e.g. phenylcarbamimidoyl etc.).

A heterocyclic acyl radical is understood to mean an acyl radical which comes from an acid with a heterocyclic group; this includes:
Heterocyclic carbonyl, in which the heterocyclic radical is an aromatic or aliphatic 5 to 6-membered heterocycle with at least one heteroatom from the group consisting of nitrogen, oxygen and sulfur (e.g. thiophenyl, fu royl, pyrrole carbonyl, nicotinoyl etc.);
Heterocycle alkanoyl in which the heterocyclic radical is 5- to 6-membered and has at least one heteroatom from the group consisting of nitrogen, oxygen and sulfur (e.g. thiophene yl-acetyl, furylacetyl, imidazolylpropionyl, tetrazolylacetyl, 2- (2- Amino-4-thiazolyl) -2-methoxyiminoacetyl etc.) and the like.

In the above examples of heterocyclic acyl residues the heterocycle and / or the aliphatic hydrocarbon some may have one or more suitable substituents sen, like the same ones that are suitable for alkyl and alkane groups were specified.

"Alkyl" is a straight or branched chain alkyl group with up to 26 carbon atoms, such as methyl, ethyl, propyl, iso propyl, butyl, isobutyl, tert-butyl, pentyl, hexyl and the same.

"Hydroxylalkyl" is a straight or branched chain alkyl rest with up to 26 carbons, the at least one Hy has hydroxyl group, preferably one or two hydroxyl groups pen.

"Alkenyl" includes straight or branched chain alkenyl groups pen with up to 26 carbon atoms, such as. B. vinyl, propenyl  (e.g. 1-propenyl, 2-propenyl), 1-methylpropenyl, 2- Methyl propenyl, butenyl, 2-ethyl propenyl, pentenyl, hexenyl.

"Alkynyl" includes straight or branched chain alkynyl groups pen with up to 26 carbon atoms.

Cycloalkyl preferably represents an optionally substituted C ₃ -C ₇ cycloalkyl; possible substituents include alkyl, alkenyl, alkynyl, alkoxy (e.g. methoxy, ethoxy etc.), halogen (e.g. fluorine, chlorine, bromine etc.), nitro and the like.

Aryl is an aromatic hydrocarbon residue, such as phenyl Naphthyl, etc., which optionally one or more suitable substituents can have ducks, such as alkyl, alkenyl, alkynyl, alkoxy (e.g. methoxy, ethoxy etc.), halogen (e.g. fluorine, chlorine, bromine etc.), nitro and the like.

"Aralkyl" includes mono-, di-, triphenylalkyls such as benzyl, Phenethyl, benzhydryl, trityl and the like, the aro Matic part optionally one or more suitable substituents may have such as alkoxy (e.g. methoxy, ethoxy etc.), halogen (e.g. fluorine, chlorine, bromine, etc.), nitro and the like.

"Alkylene" includes straight or branched chain alkylene groups which have up to 9 carbon atoms and are represented by the formula

- (C _n H _2n ) -

can be represented, in which n is an integer from 1 to 9, such as methylene, ethylene, trimethylene, methylethylene, tetramethylene, 1-methyltrimethylene, 2-ethylethylene, pentamethylene, 2-methyltetramethylene, isopropylethylene, hexamethylene, and the like; preferred alkylene radicals have up to 4 carbon atoms, and radicals with 3 carbon atoms such as, for. B. Trimethylene. The hydrogen atoms can also be replaced by substituents, such as halogen radicals.
"Alkenylene" includes straight or branched chain alkenylene groups with up to 9 carbon atoms, which are represented by the formula

- (C _n H _2n-2 ) -

can be reproduced in which n is an integer of 2 to 9, such as B. vinylene, propenylene (e.g. 1-propenylene, 2- Propenylene), 1-methylpropenylene, 2-methylpropenylene, buteny len, 2-ethylpropenylene, pentenylene, hexenylene and the like; the alkenylene radical can particularly preferably contain up to 5 carbons Have substance atoms and in particular 3 carbon atoms such as e.g. B. 1-propenylene. The hydrogen atoms can also be sub substituents, such as halogen radicals, may be replaced.

"Hydroxyalkylene" may include straight or branched chain alkylene radicals which have up to 9 carbon atoms, where at least one selected carbon atom is substituted by a hydroxy group; these residues can be represented by the formula

- (C _n H _2n-z ) (OH) _z -

are reproduced in which n is an integer from 1 to 9 and z is an integer to which 1 ≦ z ≦ n applies. Too suitable Examples of such hydroxyalkylene groups include Hy droxymethylene, hydroxyethylene (e.g. 1-hydroxyethylene and 2- Hydroxyethylene), hydroxytrimethylene (e.g. 1-hydroxy trimethylene, 2 hydroxytrimethylene and 3-hydroxytrimethylene), Hydroxytetramethylene (e.g. 2-hydroxytetramethylene), 2-hydroxy  2-methyltrimethylene, hydroxypentamethylene (e.g. 2-hydroxy pentamethylene), hydroxyhexamethylene (e.g. 2-hydroxyhexa methylene) and the like. A low is particularly preferred res hydroxyalkylene with up to 4 carbon atoms and esp special one with 3 carbon atoms such. B. 2- Hydroxytrimethylene. The hydrogen atoms can also pass through Substituents such as halogen radicals can be replaced.

"Alkylene amine" includes straight or branched chain alkylene amine groups, which have up to 9 carbon atoms and by the formula

- (C _n H _2n ) -N- (C _m H _2m ) -

can be reproduced in which n and m are the same and ver can be different and are an integer from 0 to 9, for the 1 ≦ n + m ≦ 9 applies, such as methylene amine, ethylene amine, dime ethyleneamine, trimethyleneamine, methyleneethyleneamine, tetramethy lenamine, 1-methyltrimethyleneamine, 2-ethylethyleneamine, ethylene methylene amine, pentamethylene amine, 2-methyltetramethylene amine, Isopropylethylene amine, hexamethylene amine, and the like; be preferred alkylene amine residues have 2 carbon atoms, the end always available. Dimethylene amine is particularly preferred. The Hydrogen atoms can also be substituted by substituents such as halogen residues, be replaced.

"Alkyleneimine" includes straight-chain or branched-chain alkyleneimine groups which have up to 9 carbon atoms and are represented by the formula

- (C _n H _2n-1 ) = N- (C _m H _2m ) - or the formula - (C _n H _2n ) -N = (C _m H _2m-1 ) -

can be reproduced in which n and m are the same and ver can be different and are an integer from 0 to 9, for the 1 ≦ n + m ≦ 9 applies, such as methyleneimine, ethyleneimine, dime  ethyleneimine, trimethyleneimine, methyleneethyleneimine, tetramethy lenimine, 1-methyltrimethyleneimine, 2-ethylethyleneimine, ethylene methyleneimine, pentamethyleneimine, 2-methyltetramethyleneimine, Isopropylethyleneimine, hexamethyleneimine, and the like: be preferred alkyleneimine residues have 2 carbon atoms, the end always available. Dimethyleneimine is particularly preferred. The Hydrogen atoms can also be substituted by substituents such as halogen residues, be replaced.

"Alkenylene amine" includes straight or branched chain alkenylene amine groups with up to 9 carbon atoms, which are represented by the formulas

- (C _n H _2n-2 ) -N- (C _m H _2m-2 ) -; - (C _o H _2o ) -N- (C _n H _2n-2 ) -; - (C _n H _2n-2 ) -N- (C _o H _2o ) -

can be reproduced in which n and m are the same or ver are different and are an integer from 2 to 9 for which m + n ≦ 9 applies, and o is a number between 0 and 7 and o + n ≦ 9 applies, such as. B. vinylene amine, methylene vinylene amine, divinylene min. Propenylene amine (e.g. 1-propenylene amine, 2-propenylene amine), Methylene propenylene amine, 1-methyl propenylene amine, 2- Methyl propenylene amine, butenylene amine, 2-ethylene propenylene amine, Pentenylene amine, hexenylene amine, vinyl methylene amine and the like chen. The hydrogen atoms can also be replaced by substituents, such as halogen residues.

"Alkenylene imine" includes straight or branched chain alkenylene imine groups with up to 9 carbon atoms, which are represented by the formulas

- (C _n H _2n-3 ) = N- (C _m H _2m-2 ) -; - (C _o H _2o-1 ) = N- (C _m H _2m-2 ) -; - (C _n H _2n-3 ) = N- (C _o H _2o ) -;
- (C _n H _2n-2 ) = N- (C _m H _2m-3 ) -; - (C _o H _2o ) -N = (C _m H _2m-3 ) -; - (C _n H _2n-2 ) -N = (C _o H _2o-1 ) -

can be reproduced in which n and m are the same or ver are different and are an integer from 2 to 9 for which m  + n ≦ 9 applies, and o is a number between 0 and 7 and o + n ≦ 9 applies, such as. B. vinyleneimine, methylene vinyleneimine, ethylene vinylenimine, propenyleneimine (e.g. 1-propenylenimine, 2- Propenylene imine), methylene propenylene imine, 1-methyl propenylene imine, 2-methylpropenyleneimine, butenyleneimine, 2-ethylenepro penylenimine, pentenylenimine, hexenylenimine, vinylemethyleneimine and the same. The hydrogen atoms can also be sub substituents, such as halogen radicals, may be replaced.

"Hydroxyalkylene amine" can include straight or branched chain alkylene radicals which have up to 9 carbon atoms, at least one selected carbon atom being substituted by a hydroxyl group; these residues can be represented by the formula

- (C _n H _2n-z ) (OH) _z -N- (C _m H _2m-y ) (OH) _y

are reproduced in which n and m are the same or different are and are an integer from 0 to 9 for which 1 ≦ n + m ≦ 9 applies, and z upd y are the same or different and one go are a number for which 0 ≦ z ≦ n and 0 ≦ y ≦ m and y + z ≧ 1 applies. Suitable examples of such hydroxyalkylene amine groups include hydroxymethylene amine, hydroxyethylene amine (e.g. 1-hydroxyethylene amine and 2-hydroxyethylene amine), hydroxy trimes ethylene amine (e.g. 1-hydroxytrimethylene, 2-hydroxytrimethylene amine and 3-hydroxytrimethyleneamine), hydroxytetramethyleneamine (e.g. 2-hydroxytetramethylene amine), 2-hydroxy-2-methyltri methylene amine, hydroxypentamethylene amine (e.g. 2-hydroxypenta methylene amine), hydroxyhexamethylene amine (e.g. 2-hydroxyhexa methylene amine), methylene hydroxymethylene amine, methylene hydroxy ethylene amine and the like. A never is particularly preferred deres Hydroxyalkylenamin with 2 carbon atoms and one Nitrogen atom, the two carbon atoms being terminal are. The hydrogen atoms can also be replaced by substituents, such as halogen residues.  

"Hydroxyalkyleneimine" can include straight-chain or branched-chain alkylene radicals which have up to 9 carbon atoms, where at least one selected carbon atom is substituted by a hydroxyl group; these residues can be represented by the formula

- (C _n H _2n-z-1 ) (OH) _z = N- (C _m H _2m-y ) (OH) _y ; - (C _n H _2n-z-1 ) (OH) _z -N = (C _m H _2m-y ) (OH) _y

are reproduced in which n and m are the same or different are and are an integer from 0 to 9 for which 1 ≦ n + m ≦ 9 applies, and z and y are the same or different and one go are a number for which 0 ≦ z ≦ n-1 and 0 ≦ y ≦ m-1 and y + z ≧ 1 applies. Suitable examples of such hydroxyalkylenes Mining groups include hydroxymethyleneimine, hydroxyethyleneimine (e.g. 1-hydroxyethyleneimine and 2-hydroxyethyleneimine), Hy droxytrimethyleneimine (e.g. 1-hydroxytrimethylene, 2-hydroxy trimethyleneimine and 3-hydroxytrimethyleneimine), hydroxytetra methyleneimine (e.g. 2-hydroxytetramethyleneimine), 2-hydroxy-2- methyltrimethyleneimine, hydroxypentamethyleneimine (e.g. 2- Hydroxypentamethyleneimine), hydroxyhexamethyleneimine (e.g. 2- Hydroxyhexamethyleneimine), methylenehydroxymethyleneimine, methy lenhydroxyethyleneimine and the like. Particularly preferred becomes a lower hydroxyalkyleneimine with 2 carbon atoms and a nitrogen atom, the two carbon atoms are terminal. The hydrogen atoms can also be sub substituents, such as halogen radicals, may be replaced.

The radical X ₃ can preferably be chosen such that esters are formed on the sulfono group. Suitable examples of such esters according to the formula (I) include alkyl esters (e.g. methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, isobutyl ester, hexyl ester, etc.);
Aralkyl esters (benzyl esters, phenethyl esters, benzhydryl esters, trityl esters, etc.);
Aryl esters (e.g. phenyl esters, tolyl esters, naphthyl esters, etc.); Aroyl alkyl esters (e.g. phenacyl esters etc.); and silyl esters (e.g., from trialkylhalosilyl, dialkyldihalosilyl, alkyl trihalosilyl, dialkylarylhalosilyl, trialkoxyhalosilyl, dialkylaralkylhalosilyl, dialkoxydihalosilyl, trialkoxyhalosilyl, etc.) and the like.

In the above ester, the alkane and / or arene part can be optional have at least one suitable substituent, such as halo gene, alkoxy, hydroxy, nitro or the like.

The 5- and 6-membered cyclic compounds for which A can be aromatic or aliphatic and sub be substituted, for example by alkyl groups with up to 7 Carbon atoms and hydroxy groups.

The 5- and 6-membered heterocyclic compounds for which A can stand, and besides carbon at least one He Teroatoms contained as ring members can be saturated or unsung be satisfied. Examples are azixan, diazixan, azixin, diazi xin, azolane, diazolane, azole, diazole, oxolane, dioxoles, oxole, Dioxol, oxixan, dioxixan, oxixin and dioxixin. You can ali be phatic or aromatic and by alkyl groups with up to be substituted to 7 carbon atoms and hydroxyl groups.

X ₃ is preferably a metal of the first, second or third main group of the periodic table, ammonium, substituted ammonium, or ammonium compounds which are derived from ethylenediamine or amino acids. That is, the salt compounds of the organosulfur compounds with organic or organic bases (e.g. sodium salt, potassium salt, calcium salt, aluminum salt, ammonium salt, magnesium salt, triethylamine salt, ethanolamine salt, dicyclohexylamine salt, ethylenediamine salt, N, N'-dibenzylethylenediamine salt, etc.) and salts with Amino acids (e.g. arginine salt, aspartic acid salt, glutamic acid salt, etc.) and the like are formed.

R ₃ is particularly preferably an amide radical in which the substituents of the nitrogen independently of one another are hydrogen, a hydroxyl group, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted acyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocyclic radical or halogen.

The compounds according to the formulas (I) to (VIII) in their protonated form as ammonium salt or ganic or inorganic acids, such as hydrochloric acid, bromine hydrochloric acid, sulfuric acid, nitric acid, methanesulfonic acid re, p-toluenesulfonic acid, acetic acid, lactic acid, maleic acid, Fumaric acid, oxalic acid, tartaric acid, benzoic acid, etc. are present.

The compounds of the formulas (I) to (VIII) according to the invention allow, for example, double-containing or chiral groups R ₁ , R ₂ , R ₃ , R ₄ , X ₁ , X ₂ , X ₃ , X ₄ , X ₅ or A to occur spatial isomer too. The use of the compounds according to the invention comprises all spatial isomers both as pure substances and in the form of their mixtures.

The organosulfur compounds are especially for therapeutic and prophylactic treatment of infections suitable for humans and animals that are infected by viruses, bacteria, and causing multicellular parasites and fungi.

The compounds are against unicellular parasites (protozoa)  effective, especially against malaria and Sleeping sickness as well as Chagas disease, toxoplasmosis, the amoebic dysentery, the leishmaniasis, the trichomoniasis, the Pneumocystosis, balantidiosis, cryptosporidiosis, Sarcocystosis, Acanthoma, Naeglerosis, Coccidio se, the Giardiosis and the Lambliosis.

They are therefore in particular as malaria prophylaxis and as prophylaxis of sleeping sickness and Chagas disease, toxoplasmosis, amoebic dysentery, leishmaniasis, trichomo niasis, pneumocystosis, balantidiosis, cryptospori diosis, sarcomocystosis, acanteglobe disease, coccidiosis, giardiosis and lambliosis.
The active compounds according to the invention can be used in particular against the following bacteria:
Bacteria of the Propionibacteriaceae family, in particular of the Propionibacterium genus, in particular the Propionibacte rium acnes species,
Bacteria of the Actinomycetaceae family, in particular the Actinomyces gate,
Bacteria of the genus Corynebacterium, in particular the species Corynebacterium, diphteriae and Corynebacterium pseudotubercu losis,
Bacteria of the family Mycobacteriaceae, of the genus Mycobacte rium, in particular the species Mycobacterium leprae, Mycobacte rium tuberculosis, Mycobacterium bovis and Mycobacterium avi um,
Bacteria of the family Chlamydiaceae, in particular the species Chlamydia trachomatis and Chlamydia psittaci,
Bacteria of the genus Listeria, in particular the species Listeria monocytogenes,
Bacteria of the species Erysipelthrix rhusiopathiae, bacteria of the genus Clostridium,
Bacteria of the genus Yersinia, of the species Yersinia pestis, Yersinia pseudotuberculosis, Yersinia enterocolitica and Yer sinia ruckeri,
Bacteria of the family Mycoplasmataceae, the genera My coplasma and Ureaplasma, especially the species Mycoplasma pneu moniae,
Bacteria of the genus Brucella,
Bacteria of the genus Bordetella,
Bacteria of the family Neiseriaceae, in particular of the genera Neisseria and Moraxella, in particular the species Neisseria me ningitides, Neisseria gonorrhoeae and Moraxella bovis,
Bacteria of the Vibrionaceae family, in particular of the Vibrio, Aeromonas, Plesiomonas and Photobacterium genera, in particular the Vibrio cholerae, Vibrio anguillarum and Aeromonas salmonicidas species,
Bacteria of the genus Campylobacter, in particular the species Campylobacter jejuni, Campylobacter coli and Campylobacter fe tus,
Bacteria of the genus Helicobacter, in particular the species Heli cobacter pylori,
Bacteria of the Spirochaetaceae and Leptospiraceae families, in particular of the Treponema, Borrelia and Leptospira genera, in particular Borrelia burgdorferi,
Bacteria of the genus Actinobacillus,
Bacteria of the Legionellaceae family, the genus Legionella,
Bacteria of the family Rickettsiaceae and family Bartonella ceae,
Bacteria of the genera Nocardia and Rhodococcus,
Bacteria of the genus Dermatophilus,
Bacteria of the Pseudomonadaceae family, in particular the Pseudomonas and Xanthomonas species,
Bacteria of the Enterobacteriaceae family, in particular of the genera Escherichia, Klebstella, Proteus, Providencia, Sal monella, Serratia and Shigella,
Bacteria of the Pasteurellaceae family, especially the Gat tung Haemophilus,
Bacteria of the Micrococcaceae family, in particular of the genera Micrococcus and Staphylococcus,
Bacteria of the Streptococcaceae family, especially the Streptococcus and Enterococcus and
Bacteria of the Bacillaceae family, especially the genera Bacillus and Clostridium.

Organic sulfur compounds and their are therefore suitable Derivatives for the treatment of the diphtheria, the acne vulgaris, the Listeriosis, the erysipelas in animals, the gas fire in humans and in animals, para-rage in humans and animals, tuberculosis se in humans and animals, leprosy, and other mycobacteriosis Man and animal, paratuberculosis of animals, plague, mesente rial lymphadenitis and pseudotuberculosis in humans and Animal, cholera, legionnaires' disease, Lyme disease in humans and Animal, leptospirosis in humans and animals, syphilis, campylobac enteritis in humans and animals, Moraxella keratoconjunc tivitis and serositis of animals, brucellosis of animals and Humans, anthrax in humans and animals, actinomycosis in Humans and animals, streptotrichoses, psittacosis / ornithosis Animals, Q fever, Ehrlichiosis.

The use is also useful in Helicobacter eradication therapy for ulcers of the gastrointestinal tract.
A combination with another antibiotic can also be used to treat the above-mentioned diseases. For combination preparations with other anti-infectives, isoniazid, rifampicin, ethambutol, pyrazina mid, streptomycin, protionamide and dapsone are particularly suitable for the treatment of tuberculosis.

The active compounds according to the invention can also be used in particular for infections with the following viruses:
Parvoviridae: Parvoviruses, Dependoviruses, Densoviruses,
Adenoviridae: adenoviruses, mastadenoviruses, aviadenoviruses,
Papovaviridae: papovaviruses, in particular papillomaviruses (so-called wart viruses), polyomaviruses, in particular JC virus, BK virus, and miopapovaviruses,
Herpesviridae: all herpes viruses, in particular herpes simplex viruses, the varicella / zoster viruses, human cytomegalovirus, Epstein-Barr viruses, all human herpes viruses, human herpes virus 6, human herpes virus 7, human herpes virus 8,
Poxviridae: smallpox viruses, orthopox, parapox, molluscum contagiosum virts, aviviruses, capriviruses, leporipox viruses,
all primarily hepatotropic viruses, hepatitis viruses: hepatitis A viruses, hepatitis B viruses, hepatitis C viruses, hepatitis D viruses, hepatitis E viruses, hepatitis F viruses, hepatits G viruses,
Hepadnaviruses: all hepatitis viruses, hepatitis B virus, He patitis D viruses,
Picornaviridae: Picornaviruses, all enteroviruses, all polioviruses, all Coxsackieviruses, all echoviruses, all rhinoviruses, HIV patitis A virus, aphthoviruses,
Calciviridae: hepatitis E viruses,
Reoviridae: reoviruses, orbiviruses, rotaviruses,
Togaviridae: Togaviren, Alphaviren ,, Rubiviren, Pestiviren, Rubellavirus,
Flaviviridae: flaviviruses, TBE virus, hepatitis C virus,
Orthomyxoviridae: all influenza viruses,
Paramyxoviridae: paramyxoviruses, morbillivirus, pneumovirus, measles virus, mumps virus,
Rhabdoviridae: rhabdoviruses, rabies virus, lyssavirus, viscous stomatitis virus,
Coronaviridae: Coronaviruses,
Bunyaviridae: Bunyaviren, Nairovirus, Phlebovirus, Uukuvirus, Hantavirus,
Arenaviridae: arenaviruses, lymphocytic choriomeningitis virus,
Retroviridae: retroviruses, all HTL viruses, human T-cell leu kemia virus, oncornaviruses, spumaviruses, lentiviruses, all HI viruses,
Filoviridae: Marburg and Ebola viruses,
Slow virus infections, prions,
Oncoviruses, leukemia viruses.

The organic sulfur compounds according to the invention are therefore suitable for combating the following viral infections:

Eradication of papilloma viruses to prevent tumors, especially caused by tumors of the genital organs due to papilloma viruses in humans, eradication of JC viruses and BK viruses, eradication of herpes viruses, eradication of human Herpes viruses 8 for the treatment of Kaposi's sarcoma, eradication of cytomegalovirus before transplantation, eradication of Eppstein-Barr viruses before transplantation and for the prevention of Eppstein-Barr virus-associated tumors, eradication of Hepa titis viruses for the treatment of chronic liver diseases and for the prevention of liver tumors and cirrhosis, Eradi cation of Coxsackieviruses in cardiomyopathies, eradication of Coxsackieviruses in Diabetes Mellitus Patients, Eradikati on immunodeficiency viruses in humans and animals, treatment of Concomitant infections in AIDS patients, treatment of inflammation viral genesis of the respiratory tract (laryngeal papillo me, hyberplasia, rhinitis, pharyngitis, bronchitis, pneumoni en), the sensory organs (keratoconjunctivitis), the nervous system stems (poliomyelitis, meningoencephalitis, encephalitis, suba kute sclerosing panencephalitis, SSPE, progressive multi focal leukoencephalopathy, lymphocytic choriomeningitis), of the gastrointestinal tract (stomatitis, gingivostomatitis, oesopha gitis, gastritis, gastroenteritis, diarrhea), the Liver and biliary system (hepatitis, cholangitis, hepato cellular carcinoma), of the lymphatic tissue (mononucleosis, Lymphadenitis), the hematopoietic system, the sex organs (mumps orchitis), the skin (warts, dermatitis, herpes  labialis, cold sores, herpes zoster, shingles), the Mucous membranes (papillomas, conjunctive apapillomas, hyperplasias, Dysplasia), the cardiovascular system (arteritis, myocardi tis, endocarditis, pericarditis), the kidney-urinary system, of the genital organs (anogenital lesions, warts, genital warts, acute condylomas, dysplasias, papillomas, cervix dysplasia, condylomata acuminata, epidermodysplasia verruci formis), the organs of movement (myositis, myalgia), treatment foot-and-mouth disease of the two-toed ungulates, Colorado Tick fever, dengue syndrome, hemorrhagic fie bers, early summer meningoencephalitis (TBE) and yellow feverish.

The compounds described, i. H. the organic sulfur Compounds of formula (I) to (VIII) and esters and amides the same on the sulfono or sulfino group and salts, Esters and amides thereof are highly cytotoxic Efficacy against single and multicellular parasites, esp especially against the pathogens of malaria and sleep illness. Accordingly, the compounds of the invention useful for the treatment of infectious diseases, the through viruses, bacteria, parasites and fungi in humans and Animal caused. The connections are also for the Use to prevent diseases caused by viruses, Bak terie, parasites and fungi are caused, in particular as malaria prophylaxis and as sleeping sickness prophylaxis ge is suitable.

The organosulfur compounds according to the invention generally include pharmaceutically acceptable salts, ami de, ester, a salt of such an ester, or compound gene, the compounds of the invention when applied as metabolic products or breakdown products, also called "prodrugs", can be administered in ir in a suitable manner analogous to known anti-infectious  active agents (mixed with a non-toxic pharma acceptable carrier).

Pharmaceutically acceptable salts of the compounds include Salts which the compounds of the formulas (1) according to the invention, to (VIII) in their protonated form as an ammonium salt African or organic acids, such as hydrochloric acid, sulfuric acid, Citric acid, maleic acid, fumaric acid, tartaric acid, p- Toluenesulfonic acid.

The salts which are formed by suitable selection of X ₃ , such as sodium salt, potassium salt, calcium salt, ammonium salt, ethanolamine salt, triethylamine salt, dicyclohexylamine salt and salts of an amino acid such as arginine salt, aspartic acid salt, glutamic acid salt, are also pharmaceutically particularly suitable.

The activity of the substances is in a test system Right. This system is based on the measurement of inhibition the growth of bacteria, parasites, viruses, fungi or Plants in vitro. To this end, test procedures are used in part used, which are known to the expert.

For example, to determine antimalaria activity Inhibition of the growth of malaria parasites in blood cultures certainly.

The determination of the antibacterial activity is based on Mes inhibition of bacteria growth on nutrient media and in Liquid cultures.

The determination of the antiviral activity is based on inhibition the formation of viral elements in cell cultures.

The determination of the fungicidal activity is based on inhibition  the growth of fungi on nutrient media and in liquid cultures.

Some of the microorganisms that can be examined can only be examined in animal models. Here we will then apply the appropriate models.

Substances that are effective in in vitro measurement systems show, further investigated in in vivo models. The antiparasitic, antiviral, fungicidal or antibacterial Activity is further evaluated in the corresponding animal models iert.

The screening for herbicidal activity is carried out using Algensy systems and measurement of isoprene emissions from plants under Standard conditions determined.

The pharmaceutically active agents can be in the form of pharma deutical preparations in dosage units the. This means that the preparation in the form of individual parts le, z. B. tablets, dragees, capsules, pills, suppositories and ampoules are present, the active ingredient content of which is a fraction or a multiple of a single dose. Thu Sation units can, for. B. 1, 2, 3 or 4 single doses or Contain 1/2, 1/3 or 1/4 of a single dose. A single do sis preferably contains the amount of active ingredient that is present in a Application is administered and usually an entire, a half or a third or a quarter of a day dose corresponds.

Taking non-toxic, inert pharmaceutically acceptable drugs materials are solid, semi-solid or liquid diluents tel, fillers and formulation auxiliaries of all kinds stand.

The preferred pharmaceutical preparations are tablets,  Coated tablets, capsules, pills, granules, suppositories, solutions, Suspensions and emulsions, pastes, ointments, gels, creams, lo tion, powder and sprays called. Tablets, coated tablets, capsules, Pills and granules can be the active ingredient or ingredients in addition to the contain conventional carriers, such as (a) filling and stretching tel, e.g. B. starches, milk sugar, cane sugar, glucose, mannitol and silica, (b) binders, e.g. B. Carboxymethyl cellulo se, alginates, gelatin, polyvinylpyrrolidone, (c) damp means, e.g. B. glycerin, (d) disintegrant, e.g. B. agar, Calcium carbonate and sodium carbonate, (e) solution retarders, e.g. B. Paraffin and (f) absorption accelerators, e.g. B. quaternary re ammonium compounds, (g) wetting agents, e.g. B. cetyl alcohol, Glycerol monostearate, (h) adsorbent, e.g. B. kaolin and. Bentonite and (i) lubricants, e.g. B. talc, calcium and Ma magnesium stearate and solid polyethylene glycols or mixtures of substances listed under (a) to (i).

The tablets, dragees, capsules, pills and granules can with the usual, optionally containing opacifiers tendency coatings and covers and so together be set that they only or be the active ingredients preferably in a certain part of the intestinal tract If necessary, deliver with a delay, with z. B. Polymer substances and waxes can be used.

The active ingredient (s) can optionally be combined with an or several of the above-mentioned carriers also in microver encapsulated form.

Suppositories can besides the active ingredient (s) the usual Chen water-soluble or water-insoluble carriers hold, e.g. B. polyethylene glycols, fats, e.g. B. cocoa fat and higher esters (e.g. C14 alcohol with C16 fatty acid) or Gemi of these substances.  

Ointments, pastes; Creams and gels can next to the or Active substances contain the usual carriers, e.g. B. tieri vegetable and vegetable fats, waxes, paraffins, starch, tra gant, cellulose derivatives, polyethylene glycols, silicones, bento nite, silica, talc and zinc oxide or mixtures of these Fabrics.

Powders and sprays can in addition to the active ingredient (s) Lichen carriers included, for. B. milk sugar, talc, Kie silica, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays can also be used union blowing agents, e.g. B. chlorofluorocarbons, ent hold.

Solutions and emulsions can be added to the active ingredient (s) the usual carriers such as solvents, solubilizers and emulsifiers, e.g. B. water, ethyl alcohol, isopropyl alcohol, Ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, Pro pylene glycol, 1,3-butylene glycol, dimethylformamide, oils, esp special cottonseed oil, peanut oil, corn oil, olive oil, Castor oil and sesame oil, glycerin, glycerin formal, tetrahydro furfuryl alcohol, polyethylene glycols and fatty acid esters of Contain sorbitans or mixtures of these substances.

The solutions and emulsions can be used for parenteral administration are also available in sterile and blood isotonic form.

Suspensions can besides the active ingredient (s) the usual Chen carriers such as liquid diluents, e.g. B. What water, ethyl alcohol, propylene glycol, suspending agents, e.g. B. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and Sorbitan esters, microcrystalline cellulose, aluminum metal hydroxide, bentonite, agar and tragacanth or mixtures of these Contain substances.  

The formulation forms mentioned can also contain colorants, Preservatives as well as smell and taste-improved Additives, e.g. B. peppermint oil and eucalyptus oil and sweeteners, e.g. B. saccharin.

The active ingredients of the formulas (I) to (VIII) should be listed in the above listed pharmaceutical preparations, preferably in a concentration of about 0.1 to 99.5% by weight, preferably from about 0.5 to 95% by weight of the total mixture.

In addition to the compounds, the pharmaceutical preparations can gene of formulas (I) to (VIII) also other pharmaceutical Contain active ingredients.

The compounds can be used with previously described substances with antibacterial, antiviral, antimyctoic and antipa rasitic properties. These include in particular compounds that have already been used in therapy or are still being used. For this purpose, special substances are particularly suitable, which are listed in the Red List or in Simon / Stille, Antibiotic Therapy in Clinic and Practice, 9th Edition 1998 Schattauer Verlag, or at
http: /www.customs.treas.gov/imp- exp / rulings / harmoniz / hrm129.html listed on the Internet. In particular, the derivatives with penicillins, benzylpenicillin (Penicillin G), phenoxypenicillins, isoxazolylpenicil line, aminopenicillins, ampicillin, amoxixillin, bacampicil lin, carboxypenicillin, ticarcillin, temocillin, acyalaminope nicilline, aplocillinillin, azlocillin, azlocillin, azlocillin Group, cefuroxime group, cefoxitin group, cefoxitin, cefotetan, cefmetazole, latamoxef, flomoxef, cefotaxim group, cefozidim, ceftazidim group, ceftazidim, cefpirom, cefepim, other cephalefulphalineporine, cefalefalosporin, cefalefosaline, cefalefosaline, cefalefosaline, cefalefosaline, cefalefosaline, cefalefosalone, cefalefosaline, , Cefprozil, new oral cephalosporins with a broader spectrum, Cefixim, Cefpodoxim-Proxetil, Cefuroxim-Axetil, Cefetamet, Cefotiam-Hexetil, Cefdinir, Ceftibuten, others β-lactam antibiotics, Carbapenem, Biipenemamemon, Amapenemememil / Cil β-lactamase inhibitor, clavulanic acid / amoxicillin, clavulanic acid / ticarcillin, Sulbac tam / ampicillin, tazobactam / pipe racillin, tetracyclines, tracyclin Oxyte, Rolitetraxyxlin, doxycycline, minocycline, Chloram phenicol, aminoglycosides, gentamicin, tobramycin, netilmicin, amikacin, Spectinomyxin, macrolides, erythromycin, Cla rithromycin, roxithromycin, azithromycin, dirithromycin, Spi ramycin, josamycin, lincosamides, clindamycin, Fusidic acid, glycopeptide antibiotics, vancomycin, tecoplanin, pristi namycin derivatives, fosfomycin, antimicrobial folic acid antagonists, sulfonamides, co-trimoxazole, trimethoprim, other dia minopyrimidine-sulfonamide combinations, nitrofurone (nitrofyronone) , Norfloxacin, ciprofloxacin, ofloxacin, sparfloxacin, enoxacin, fleroxacin, pefloxacin, lomefloxacin, Bay Y3118, nitroimidazole, antimyco bacterial agents, isoniazid, rifampicin, rifabutin, ethantcinamidonolone, ethantcinamidonolone Local antibiotics, bacitracin, ty rothricin, polymyxins, neomycin, kanamycin, paromomycin, M upi rocin, antiviral agents, acyclovir, ganciclovir, azidothymi din, didanosine, zalcitabine, thiacytidine, stavudine, ribavirin, idoxuridine, trifluridine, foscarnet, amantadine, interferons, tibol derivatives, proteinase inhibitors, poly, nytinotherininin, antimine, antimine Natamycin, Azole, Azole for septic therapy, Miconazole, Ketoconazole, Itraconazole, Fluconazole, UK-109.496, Azole for topical use, Clotrimazole, Eco nazol, Isoconazole, Oxiconazole, Bifonazole, Flucytosine, Griseo fuloxat, Nolifinoxin, Caminopin Terbinafine, Amorolfine, Anttpchinone, Betulinic acid, Semianthraquinone, Xanthones, Naphtoquinone, Aryamino Alcohols, Quinine, Quinidines, Mefloquine, Halofantrine, Chloroquine, Amodiaquine, Acridine, Ben zonaphthyridine, Mepacrine, Pyronaridone, Prozone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Sulfonaridone, Pro Chlorprogua nil, diaminopyrimidines, pyrimethamine, primaquine, aminoquinolines, WR 238,605, tetracycline, doxycycline, clindamycin, norfloa acin, ciprofloxaci n, ofloxacin, artemisinin, dihydroartemisi nin, 10b artemether, arteether, atresunate, atovaquone, sura min. Melarsoprol, nifurtmox, stibogluconate sodium, pentami din, amphotericin B, metronidazole, clioquinol, mebendazole, niclosamide; Praziquantel, pyrantel, tiabendazole, diethylcarbamazine, ivermectin, bithionol, oxamniquin, metrifonate, piperazin, embonate.

Furthermore, the organic sulfur compounds in the pharmaceutical agents in combination with sulfonamide, sulfa doxin, artemisinin, atovaquone, quinine, chloroquine, hydroxy chloroquine, mefloquine, halofantrine, pyrimethamine, armesin, Te tracycline, doxycycline, proguanil, metronidazole, praziquantil, Niclosamide, mebendazole, pyrantel, tiabendazole, diethylcarba zin, piperazine, pyrivinum, metrifonate, oxamniquin, bithionol or suramin or more of these substances.

The manufacture of the pharmaceutical accessories listed above Horse riding is done in the usual way according to known methods, e.g. B. by mixing the active ingredient or ingredients with the or Carriers.

The preparations mentioned can be used in humans and animals the oral, rectal, parenteral (intravenous, intramuscular, sub cutaneous), intracisternal, intravaginal, intraperitoneal, local (Powder, ointment, drops) and for the treatment of infections in Cavities, body cavities are applied. As a suitable addition Preparations come with injection solutions, solutions and suspensions NEN for oral therapy, gels, infusion formulations, emul ions, ointments or drops. For local therapy ophthalmic and dermatological formulations, Silver and other salts, ear drops, eye ointments, powder  or solutions are used. In animals, the intake also in suitable form via the feed or drinking water take place. Gels, powders, powders, tablets, Prolonged-release tablets, premixes, concentrates, granules, pellets, Tablets, boluses, capsules, aerosols, sprays, inhalants Humans and animals can be used. Furthermore, the inventions compounds according to the invention in other carrier materials such as Example plastics, (plastic chains for local therapy), Collagen or bone cement can be incorporated.

In general, it has been in both human and of veterinary medicine has been shown to be advantageous Active substances of the formulas (I) and (VIII) in total amounts of about 0.05 to about 600, preferably 0.5 to 200 mg / kg body weight weight each 24 hours, possibly in the form of several individual ga ben to give the desired results. A single dose preferably contains the active ingredient (s) in amounts of about 1 to about 200, in particular 1 to 60 mg / kg Body weight. However, it may be necessary from the ge named doses vary, depending on the type and body weight of the patient to be treated, the type and severity of the disease, the type of preparation and the application of the drug and the period or interval within which the administration takes place.

So in some cases it may be sufficient with less than the above amount of active ingredient to get by while in at whose cases exceeded the amount of active ingredient mentioned above must become. The determination of the optima required in each case len dosage and type of application of the active ingredients can by the specialist on the basis of his specialist knowledge.

The compounds of the invention can in the usual Kon concentrations and preparations in animals together with the Feed or with feed preparations or with drinking water  are given.

Furthermore, the compounds according to the invention can be outstanding used as bactericides, fungicides and herbicides in plants be set.

In principle, the person skilled in the art knows which synthetic route he uses to choose for the production of the substances according to the invention Has.

example Synthesis of HC (= O) -N (OH) -CH ₂ CH ₂ CH ₂ -SO ₃ H N-hydroxylamino propanesulfonic acid a

1 equivalent of a 50% solution of hydroxylamine in water is mixed with an equivalent of γ-sulton in acetonitrile and Maintained at 37 ° C for 24 h. Then the solution is concentrated under Achievement of a white-beige raw product, which from a Ge can be recrystallized from methanol and ethanol.

N-formyl-N-hydroxylamino-propanesulfonic acid b

2 ml of formic acid are added dropwise to 4 ml of acetic anhydride at 0 ° C. leaves 10 min at the same temperature and 15 min at room temperature stir, cool again to 0 ° C and drip 0.02 mol des inner salt a, dissolved in a little formic acid at 0 ° C. After stirring for 1 hour at room temperature, the solution becomes un ter reduced pressure, the product in 50 ml of methanol dissolved, heated to 60 ° C and with a mixture of Etha nol / isopropanol added. A white solid precipitates out redissolved in methanol and from ethanol, among others Adding isopropanol that can be recrystallized.

Claims (20)

1. Organic sulfur compounds of the general formula (I)
wherein R ₃ is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted Aralkyl, substituted and unsubstituted alkenyl having up to 26 carbon atoms, substituted and unsubstituted alkynyl having up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, halogen OX ₃ and NX ₄ X ₅ ,
wherein X ₃ is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl with up to 26 carbon atoms, substituted and unsubstituted alkynyl with up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, a silyl, a cation of an organic and inorganic base, in particular a metal of the first, second or third main group of the periodic table, ammonium, substituted ammonium and ammonium compounds derived from ethylenediamine or amino acids,
and X ₄ and X _{5 are the} same or different and are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radical and halogen,
where A is selected from the group consisting of

• a) from an alkylene radical, alkenylene radical, a hydroxyalkylene radical,
• b) from an alkylene amine residue, an alkenylene amine residue, a hydroxyalkylene amine residue, an alkylene imine residue, an alkenylene imine residue and a hydroxyalkylene imine residue, with a nitrogen atom present in the chain which connects the sulfur atom with the nitrogen atom of the group
  connects,
• c) from the ether group (IA)
  where A ₁ and A ₂ , of which A _{II2 can} also be omitted, are the same or different and are selected from the group consisting of alkylene radical, alkenylene radical and hydroxyalkylene radical,
• d) from the keto group (IB)
  wherein A ₃ and A ₄ , one or both of which can also be omitted, are the same or different, are selected from the group consisting of alkylene radical, alkenylene radical and hydroxyalkylene radical, and
• e) and from 5- and 6-membered cyclic, preferably heterocyclic, compounds which contain at least one heteroatom as the ring member in addition to carbon, the heteroatom being selected from the group consisting of oxygen and nitrogen,

consists of
R ₁ are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radical, halogen and OX ₁ ,
wherein X ₁ are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted Cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radical,
and their pharmaceutically acceptable salts, esters and amides and salts of the esters. 2. Compounds according to claim 1, characterized in that they have the formula
correspond with
R ₁ and X _{3 are} as defined for formula (I), and A is selected from the group consisting of CNC, C = NC, CN = C,
wherein the carbon atoms can be substituted with a hydroxyl or alkyl group with up to 7 carbon atoms. 3. Compounds according to claim 2, characterized in that R ₁ is selected from the group consisting of acetyl and formyl, and X ₃ is selected from the group consisting of water, sodium, potassium, methyl, ethyl and residues 16 or 18 carbon atoms. 4. A compound according to claim 3, characterized in that
R ₁ = acyl. 5. Use according to claim 7, characterized in that
X ₃ group is selected, the ammonium and metals of the first and second main group of the periodic table, preferably sodium, potassium, calcium or magnesium, ammonium compounds derived from ethylenediamine or amino acids, preferably ethanolamine, ethylenediamine, N, N-dibenzylethylenediamine and arginine. 6. Connection according to one of claims 1 to 4, characterized in that
A preferably forms a three-membered chain between the nitrogen atom and the sulfur atom. 7. Compounds according to any one of claims 1 to 5, characterized in that they have the formula
correspond with
R ₁ is selected from the group consisting of acetyl and formyl,
Y and Z each represent hydrogen,
A ₁ is selected from the group consisting of methylene, ethylene, ethenylene, 2-hydroxypropylene and hydroxyethylene, and
X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and residues with 16 or 18 carbon atoms. 8. Compounds according to claim 1, characterized in that they have the formula
correspond with
R ₁ is selected from the group consisting of acetyl and formyl,
A ₃ is selected from the group consisting of methylene, ethylene, ethenylene, 2-hydroxypropylene, hydroxymethylene and hydroxyethylene,
A ₄ is eliminated or is methylene, and
X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and residues with 16 or 18 carbon atoms. 9. Compounds according to claim 1, characterized in that A is a heterocyclic compound in which the amino group and the sulfur atom are bound to two carbon atoms, which only are separated from each other by a heteroatom. 10. Compounds according to claim 9, characterized in that the organic sulfur compound is selected from the group consisting of compounds of the formulas
consists of
R ₁ is selected from the group consisting of acetyl and formyl, and
X ₃ is selected from the group consisting of hydrogen, sodium, potassium, methyl, ethyl and residues with 16 or 18 carbon atoms. 11. Compounds according to any one of claims 1 to 10, characterized in that R _{3 is} NX ₄ X ₅ , where X ₄ and X _{5 have} the same meaning as in formula (I). 12. Pharmaceutical preparation, characterized by an effective content of at least one organo sulfur together according to one of claims 1 to 11 with a pharmaceutically acceptable carrier. 13. Pharmaceutical preparation according to claim 12, characterized by at least one other active pharmaceutical ingredient.   14. Pharmaceutical preparation according to claim 13, characterized by one or more components of the group consisting of sulfo namid, sulfadoxine, artemisinin, atovaquone, quinine, chloro quin, hydroxychloroquine, mefloquine, halofantrine, pyrimetha min. Armesin, Tetracycline, Doxycycline, Proguanil, Metroni dazol, praziquantil, niclosamide, mebendazole, pyrantel, tia bendazole, diethylcarbazine, piperazine, pyrivinum, metrifo nat, oxamniquin, bithionol and suramin. 15. Pharmaceutical preparation according to claim 13, characterized by one or more components of the group consisting of peni cilline, benzylpenicillin (Penicillin G), phenoxypenicilli ne, isoxazolylpenicillins, aminopenicillins, ampicillins, Amoxixillin, bacampicillin, carboxypenicillin, ticarcillin, Temocillin, Acyalaminopenicilline, Azlocillin, Mezlocillin, Piperacillin, Apalcillin, Mecillinam, Cephalosporine, Cefa zolin group, cefuroxime group, cefoxitin group, cefoxi tin, cefotetan, cefmetazole, latamoxef, flomoxef, cefotaxime Guppe, cefozidim, ceftazidim group, ceftazidim, cefpirom, Cefepime, other cephalosporins, cefsulodin, cefoperazone, Oralcephalosporins of the cefalexin group, Loracarbef, Cef prozil, new oral cephalosporins with an expanded spectrum, Cefixime, cefpodoxime proxetil, cefuroxime axetil, cefetamet, Cefotiam hexetil, cefdinir, ceftibutene, other β-lactam Antibiotics, carbapenem, imipenem / cilastatin, meropenem, Biapenem, aztreonam, β-lactamase inhibitor, clavulanic acid right / amoxicillin, clavulanic acid / ticarcillin, Sulbac tam / ampicillin, tazobactam / piperacillin, tetracycline, Oxytetracycline, rolitetraxyxlin, doxycycline, minocycline, Chloramphenicol, aminoglycosides, gentamicin, tobramycin, Netilmicin, amikacin, spectinomyxin, macrolides, Erythromycin, clarithromycin, roxithromycin, azithromycin,  Dirithromycin, Spiramycin, Josamycin, Lincosamide, Clin damycin, fusidic acid, glycopeptide antibiotics, vancomycin, Tecoplanin, pristinamycin derivatives, fosfomycin, antimicro biological folic acid antagonists, sulfonamides, co-trimoxazole, Trimethoprim, other diaminopyrimidine sulfonamide Combinations, nitrofurans, nitrofurantoin, nitrofurazone, Gyrase inhibitors (quinolones), norfloxacin, ciprofloxacin, Ofloxacin, sparfloxacin, enoxacin, fleroxacin, pefloxacin, Lomefloxacin, Bay Y3118, nitroimidazole, antifungal le agent, isoniazid, rifampicin, rifabutin, ethambutol, Pyrazinamide, streptomycin, capreomycin, prothionamide, teri zidon, dapsone, clofazimin, local antibiotics, bacitracin, Tyrothricin, polymyxins, neomycin, kanamycin, paromomycin, Mupirocin, antiviral, acyclovir, ganciclovir, azi dothymidine, didanosine, zalcitabine, thiacytidine, stavudine, Ribavirin, idoxuridine, trifluridine, foscarnet, amantadine, Interferons, tibol derivatives, proteinase inhibitors, an. timykotika, polyene, amphothericin B, nystatin, natamycin, Azoles, Azoles for septic therapy, Miconazole, Ketocona zol, itraconazole, fluconazole, UK-109,496, azoles for local Application, clotrimazole, econazole, isoconazole, oxiconazole, Bifonazole, flucytosine, griseofulvin, ciclopiroxolamine, Tolnaftat, Naftifin, Terbinafin, Amorolfin, Antrachinone, Betulinic acid, semianthraquinones, xanthones, naphtoquinones, Aryamino alcohols, quinine, quinidines, mefloquine, halofan trin, chloroquine, amodiaquine, acridine, benzonaphthyridine, Mepacrine, pyronaridine, dapsone, sulfonamides, sulfadoxine, Sulfalene, Trimethoprim, Proguanil, Chlorproguanil, Dia minopyrimidines, pyrimethamine, primaquine, aminoquinolines, WR 238, 605, tetracycline, doxycycline, clindamycin, norfloxacin, Ciprofloxacin, ofloxacin, artemisinin, dihydroartemisinin, 10b artemether, Arteether, Atrtesunat, Atovaquon, Suramin, Melarsoprol, nifurtmox, stibogluconate sodium, pentamidine, Amphotericin B, metronidazole, clioquinol, mebendazole, Niclosamide, praziquantel, pyrantel, tiabendazole, die  thylcarbamazin, ivermectin, bithionol, oxamniquin, metrifo nat, piperazine, embonate. 16. Use of organic sulfur compounds according to one of claims 1 to 11 for the treatment of infectious pro eat in humans and animals caused by viruses, bacteria, Fungi or parasites are caused and as a fungicide, Bactericide or herbicide on plants. 17. Use according to claim 16 for the treatment of infections, caused by bacteria, viruses, fungi or one or multicellular parasites. 18. Use according to claim 17 for the treatment of infections, which are caused by bacteria that come from the group pe are selected from bacteria of the Propioni family bacteriaceae, especially of the genus Propionibacterium, especially the species Propionibacterium acnes, bacteria of the Family Actinomycetaceae, especially the genus Acti nomyces, bacteria of the genus Corynebacterium, in particular re the species Corynebacterium diphteriae and Corynebacterium pseudotuberculosis, bacteria of the family Mycobacteriaceae, the genus Mycobacterium, especially the species Mycobac terium leprae, Mycobacterium tuberculosis, Mycobacterium bovis and Mycobacterium avium, family bacteria Chlamydiaceae, especially the species Chlamydia trachoma tis and Chlamydia psittaci, bacteria of the genus Listeria, especially the species Listeria monocytogenes, bacteria of the Type Erysipelthrix rhusiopathiae, bacteria of the genus Clostridium, bacteria of the genus Yersinia, of the species Yersinia päptis, Yersinia pseudotuberculosis, Yersinia enterocolitica and Yersinia ruckeri, bacteria of the family Mycoplasmataceae, of the genera Mycoplasma and Ureaplasma, especially the species Mycoplasma pneumoniae, bacteria of the Genus Brucella, bacteria of the genus Bordetella, bacteria  of the Neiseriaceae family, especially of the genera Neisseria and Moraxella, especially the Neisseria species meningitides, Neisseria gonorrhoeae and Moraxella bovis, Bacteria of the Vibrionaceae family, especially the Gat Vibrio, Aeromonas, Plesiomonas and Photobacterium, especially the species Vibrio cholerae, Vibrio anguillarum and Aeromonas salmonicidas, bacteria of the Campy genus lobacter, especially the Campylobacter jejuni species, Campylobacter coli and Campylobacter fetus, bacteria of the Genus Helicobacter, in particular the species Helicobacter py lori, bacteria of the Spirochaetaceae and Lep families tospiraceae, especially the genera Treponema, Borrelia and Leptospira, especially Borrelia burgdorferi, bacteri en of the genus Actinobacillus, bacteria of the Legio family nellaceae, of the genus Legionella, bacteria of the family Rickettsiaceae and family Bartonellaceae, bacteria of the Genera Nocardia and Rhodococcus, bacteria of the genus Dermatophilus, bacteria of the family Pseudomonadaceae, ins particular of the genera Pseudomonas and Xanthomonas, bacteria Enterobacteriaceae family, especially the Gat Escherichia, Klebstella, Proteus, Providencia, Sal monella, Serratia and Shigella, bacteria of the Pa family steurellaceae, especially of the genus Haemophilus, Bakte of the Micrococcaceae family, especially of the genera Micrococcus and Staphylococcus, family bacteria Streptococcaceae, especially the genera Streptococcus and Enterococcus and bacteria of the Bacillaceae family, in particular of the genera Bacillus and Clostridium be stands, and in the Helicobacter eradication therapy Ulcers of the gastrointestinal tract. 19. Use according to claim 17 for the treatment of infections, that are caused by viruses that come from the group selected from viruses of the genus Parvoviridae, especially parvoviruses, dependoviruses, densoviruses, viruses  of the genus Adenoviridae, especially adenoviruses, mastade noviruses, aviadenoviruses, viruses of the genus Papovaviridae, especially papovaviruses, especially papillomaviruses (see above) wart viruses), polyoma viruses, in particular JC virus, BK virus, and miopapovaviruses, viruses of the genus Herpesviri dae, especially herpes simplex viruses, the varicella len / zoster viruses, human cytomegalovirus, Epstein Barr viruses, human herpes virus 6, human herpes virus 7, human herpes virus 8, viruses of the genus Poxviridae, esp special smallpox viruses, orthopox, parapox, molluscum Contagiosum virus, aviviruses, capriviruses, leporipox viruses, primarily hepatotropic viruses, especially hepatitis viruses such as Hepatitis A viruses, hepatitis B viruses, hepatitis C viruses, Hepatitis D viruses, hepatitis E viruses, hepatitis F viruses, Hepatits G viruses, hepadnaviruses, especially all He patitis viruses, such as hepatitis B virus, hepatitis D viruses, Vi of the genus Picornaviridae, especially Picornaviruses, all enteroviruses, all polioviruses, all coxsackieviruses, al le echoviruses, all rhinoviruses, hepatitis A virus, aphthovi ren, viruses of the genus Calciviridae, especially hepati tis-E viruses, viruses of the genus Reoviridae, in particular Reoviruses, orbiviruses, rotaviruses, viruses of the Togaviri genus dae, especially Togaviruses, Alphaviruses, Rubiviruses, Pesti viruses, rubella virus, viruses of the genus Flaviviridae, esp special flaviviruses, TBE virus, hepatitis C virus, viruses of the genus Orthomyxoviridae, especially influenza viruses, Viruses of the genus Paramyxoviridae, especially Paramyxovi ren, morbillivirus, pneumovirus, measles virus, mumps virus, Viruses of the genus Rhabdoviridae, especially rhabdoviruses, Rabies virus, Lyssavirus, viscous stomatitis virus, viruses the genus Coronaviridae, especially coronaviruses, viruses the genus Bunyaviridae, especially Bunyaviren, Nairovi rus, phlebovirus, uukuvirus, hantavirus, viruses of the genus Arenaviridae, especially arenaviruses, lymphocytic cho riomeningitis virus, viruses of the genus Retroviridae, esp  special retroviruses, all HTL viruses, human T-cell Leukä mie virus, oncornaviruses, spuma viruses, lentiviruses, all HI- Viruses, viruses of the genus Filoviridae, especially Marburg and Ebola virus, slow viruses, prions, onkoviruses and Leukä mie viruses exist. 20. Use according to claim 17 for prevention and treatment infections caused by unicellular parasites, näm pathogens of malaria, sleeping sickness, Chagas Disease, toxoplasmosis, amoebic dysentery, leishma niosen, trichomoniasis, pneumocystosis, balanti diose, cryptosporidiosis, sarcomocystosis, acantha Möbose, Naeglerose, Coccidiosis, Giardiosis and the lambliosis.