Background of the Invention A number of different cheating agents are known and widely used in a number of industries. Cheating agents are compounds containing donor atoms that can combine by coordinate bonding with a single metal ion to form a cyclic structure called a cheating complex or simply a chelate.

The technological importance of chelation derives from the almost universal presence of metal ions in some form either naturally or by intentional addition by man. The use of cheating agents provides a way in which the effect of metal ions can be controlled or manipulated to provide a desired effect. The complexes formed from the interaction of a metal ion and a chelate typically have properties that are significantly different from either of the original ion or cheating agent and thus the behaviour of these species can be modified.

Cheating agents are therefore typically compounds that are effective in forming complexes with metal cations (and therefore also with organic salts) thus preventing them acting as simple hydrated cations. A typical example of a cheating agent is ethylenediamine tetra-acetic acid (EDTA) (1) and derivatives

thereof which form complexes with most M2+ and M3+ species. It has been noted that gluconic acid and other hydroxy acids act similarly.

There are many features of chelation chemistry that are fundamental to most applications that involve the use of cheating compounds.

Firstly chelation provides a mechanism for the control of the concentration of the free form of the metal ions by means of the binding-dissociation equilibria of the cheating agent with the metal ion. Uses such as sequestration which is the suppression of certain properties of a metal without removing it from the system or phase, solubilization which is a process of causing constituents of a phase that are nominally insoluble to dissolve in the medium, and buffering, the effect in which the addition or the removal of an appreciable amount of a metal ion produces only a relatively small change in the concentration of that ion in the solution all depend on the appropriate control of concentration provided by cheating agents. These features or properties all have uses in industrial chemistry.

For example, sequestration of metal ions can be used to control water hardness whereas solubilization is used in dissolving boiler scale, scale in heat exchangers and hardener scale from pipes. In the mining industry solubilization using cheating compounds is used in metal recovery from ores as well as in cleaning up contaminated sites. Buffering by the use of chelation agents is useful in supplying micronutrient metal ions to biological growth systems at controlled

low concentration rates.

Secondly, in certain applications such as in catalysis chemistry cheating ligands have catalytic activity and have been used as catalysts in asymmetric synthesis of pharmaceutical compounds. Finally, chelates themselves have been found to have some use in human treatment. Thus, for example, displacements using cheating agents or chelation include treatment of poisoning by lead and other metals with EDTA (ethylene diamine tetra-acetic acid) whereby the lead is preferentially cheated to the EDTA and able to be removed from the system.

Cheating agents have also in some instances found use as biocides as certain of these compounds have the ability to interfere with intercellular processes thus killing many microorganisms at levels that will be considered non-toxic to humans.

There is therefore a need to provide additional or alternative cheating agents that have low toxicity in mammals. As the breadth of potential uses of cheating agents continues to grow there is a need to provide alternative cheating agents especially those with low toxicity as this increases the potential uses of these compounds.

Summary of the Invention In one aspect the present invention provides compounds of formula (2) or (3):

wherein X is selected from the group consisting of nitrogen, phosphorous, arsenic, antimony and bismuth; each R is independently selected from the group consisting of: (1) substituted or unsubstituted Ci to C20 alkyl ; (2) substituted or unsubstituted C2 to C20 alkenyl ; (3) substituted or unsubstituted C2 to C20 alkynyl ; (4) substituted or unsubstituted C3 to C20 cycloalkyl ; (5) substituted or unsubstituted aryl ; (6) a group of formula-O-R-wherein R : is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C2o alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (7) a group of formula-OR2C02-wherein R2 is substituted or unsubstituted C, to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (8) a group of formula-R3-CO2-wherein R3 is substituted or unsubstituted C, to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (9) a group of formula (-R4-O-) wherein R4 is substituted or unsubstituted Ci to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (10) a group of formula wherein Rs is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; and

(11) a group of formula wherein R6 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; each M is independently selected from the group consisting of carbon silicon, germanium, tin, lead, sulfur, selenium, tellurium or polonium.

N is an integer from 1 to 4, K is an integer and is either 1 or 2, or a pharmaceutical acceptable salt thereof.

In a further aspect the present invention provides methods of cheating a metallic cation involving contacting a solution or suspension containing said metallic cation with a cheating effective amount of a cheating agent of the invention.

In yet an even further aspect the present invention provides a method of solubilising a metallic deposit comprising contacting said deposit with a compound of the invention. The contacting preferably involves contacting the deposit with a solution containing the compound of the invention.

In yet a further aspect still the present invention provides a method of eradication of a microorganism comprising contacting said microorganism with a biocidally effective amount of a compound of the invention.

In yet a further aspect the invention provides a method of treatment of a bacterial infection in a patient in need thereof comprising administering a therapeutical effective amount of a compound of the invention.

The invention also relates to methods of synthesis of the compounds of the invention.

Definitions The following terms are used throughout the specification and have the following meanings unless otherwise specified: "Alkyl"means carbon atom chains having the designated number of carbon atoms which can be either straight chain or branched. Examples of alkyl include, but are not limited to, methyl, ethyl, propyl, butyl, isobutyl, and the like.

"Alkenyl"means carbon atom chains having the designated number of carbon atoms which can either be straight, chain or branched and which contain at least one double bond. The alkenyl compounds may have more than one such double bond and the orientation about each double bond is independently either cis or trans. Examples of alkenyl include, but are not limited to ethenyl, propenyl, butenyl, isobutenyl, pentenyl, hexenyl and the like.

"Alkynyl"means carbon atom chains having the designated number of carbon atoms which can be either straight chained or branched which contain at least one carbon-carbon triple bond.

As used herein the term"aryl"means single, polynucleic conjugated and fused residues of aromatic hydrocarbon or aromatic heterocyclic ring systems. examples of aryl include, but are not limited to phenyl, naphthyl, fluorenyl, pyrinyl, pyridyl, pyrollyl, and the like.

"Pharmaceutically acceptable salts"are base addition salts which can be prepared by addition of a basic compound to the compounds of the invention.

Typical pharmaceutically acceptable salts are sodium, potassium, calcium or zinc salts.

In the specification substituted means that a group may be further substituted by one or more groups selected from alkyl, alkenyl, alkynyl, aryl, fluoro, chloro, bromo, hydroxy, alkoxy, alkenyloxy, aryloxy, acyloxy, amino, alkylamino, dialkylamino, arylamino, thio, alkylthio, arylthio, cyano, nitro, acyl, amido, alkylamido, dialkylamido, carboxyl or two or more substituents may, together with the carbon atoms to which they are attached form a 5 or 6 membered aromatic or non-aromatic ring containing 0,1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur.

Detailed Description of the Invention The cheating agents of the invention are compounds of formula (2) or (3). wherein X is selected from the group consisting of nitrogen, phosphorous, arsenic, antimony and bismuth; (1) substituted or unsubstituted Ci to C20 alkyl ; (2) substituted or unsubstituted C2 to C20 alkenyl ; (3) substituted or unsubstituted C2 to C2o alkynyl ; (4) substituted or unsubstituted C3 to C20 cycloalkyl ;

(5) substituted or unsubstituted aryl ; (6) a group of formula-O-Rr-wherein R1 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (7) a group of formula-OR2CO2-wherein R2 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (8) a group of formula-R3-CO2-wherein R3 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (9) a group of formula (-R4-O-) wherein R4 is substituted or unsubstituted Ci to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (10) a group of formula wherein R5 is substituted or unsubstituted C, to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; and (11) a group of formula wherein R6 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to

C20 cycloalkyl or substituted or unsubstituted aryl ; each M is independently selected from the group consisting of carbon silicon, germanium, tin, lead, sulfur, selenium, tellurium or polonium.

N is an integer from 1 to 4, K is an integer and is either 1 or 2, or a pharmaceutical acceptable salt thereof.

In a preferred embodiment the compounds have the formula (4) or (5) wherein X is selected from the group consisting of nitrogen, phosphorous, arsenic, antimony and bismuth; each R is independently selected from the group consisting of: (1) substituted or unsubstituted Cl to C2o alkyl ; (2) substituted or unsubstituted C2 to C20 alkenyl ; (3) substituted or unsubstituted C2 to C20 alkynyl ; (4) substituted or unsubstituted C3 to C20 cycloalkyl ; (5) substituted or unsubstituted aryl ; (6) a group of formula-O-R,-wherein R, is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ;

(7) a group of formula-OR2CO2-wherein R2 is substituted or unsubstituted Ci to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (8) a group of formula-R3-CO2-wherein R3 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (9) a group of formula (-R4-O-) wherein R4 is substituted or unsubstituted Ci to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (10) a group of formula wherein R5 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; and (11) a group of formula wherein R6 is substituted or unsubstituted C, to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; each M is independently selected from the group consisting of carbon silicon, germanium, tin, lead, sulfur, selenium, tellurium or polonium.

N is an integer from 2 to 4, K is either 1 or 2,

or a pharmaceutical acceptable salt thereof.

There are many preferred substructures of the broad set of compounds of formula (2). Thus these compounds can be present as the free acids or in the partially or fully neutralized salt forms. For clarity a number of the possible forms are shown below : ACIDFORM: PARTIALLY NEUTRALIZED :

FULLY NEUTRALIZED :

wherein Z is a pharmaceutically acceptable cation.

There are also corresponding preferred substructures of the broad set of compounds of formula (3). These compounds can also be present as the free acids or in partially or fully neutralised salt form. These are shown below :

ACID FORM PARTIALLY NEUTRALIZED : FULLY NEUTRALIZED :

wherein Z is a pharmaceutical acceptable cation.

It is noted the structures shown are those in which the 3 substituents on the X atoms are the same. This has been done merely for convenience in representing the structure. Whilst these are the most convenient to synthesize and hence to manufacture there is no requirement for this symmetry in the molecules of the invention.

The component X of the structures of the compounds of the invention is an element selected from the V series of the periodic table of elements. X is thus an element selected from the group consisting of nitrogen, phosphorous, arsenic, antimony or bismuth. It is preferred that X is either nitrogen or phosphorous with nitrogen being particularly preferred.

The R group is independently selected from the group consisting of: (1) substituted or unsubstituted C1 to C20 alkyl ; (2) substituted or unsubstituted C2 to C20 alkenyl ; (3) substituted or unsubstituted C2 to C20 alkynyl ; (4) substituted or unsubstituted C3 to C20 cycloalkyl ; (5) substituted or unsubstituted aryl ; (6) a group of formula-O-Ri-wherein R, is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (7) a group of formula-OR2CO2-wherein R2 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (8) a group of formula-R3-CO2-wherein R3 is substituted or unsubstituted C, to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (9) a group of formula (-R4-O-) wherein R4 is substituted or unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; (10) a group of formula wherein R5 is substituted or unsubstituted Ci to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl ; and (11) a group of formula wherein R6 is substituted or

unsubstituted Cl to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 cycloalkyl or substituted or unsubstituted aryl.

The alkyl group is selected from the group consisting of substituted or unsubstituted straight or branched chain alkyl groups having from 1 to 20 carbon atoms. If R is alkyl it is preferred that it is methyl.

The alkenyl group can be substituted or unsubstituted and can have from 2 to 20 carbon atoms. The alkenyl group may be straight chain or branched and may contain more than one double bond with the orientation about each double bond being either cis or trans. The R group can also be substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, or aryl.

R can also be represented by a group of the formula-O-R1-wherein R1 is a substituted or unsubstituted Cl to C20 alkyl. When it is used in this regard the definition can be the same as the definition of alkyl referred to above. R can also be a group of the formula-O-R2CO2 in which case the linking group between the X moiety and the M moiety is a carboxylate residue. This linking moiety can also contain an aryl group. The R group may also be a group of the formula-Rs-CO2-.

Linking R moieties of formula-R4-O-, and wherein R4, R, and R6 as defined above are also envisaged.

The element M in the compounds of the invention is either a IV series element of the periodic table such as carbon, silicon, germanium, tin and lead or a VI series element in the periodic table such as oxygen, sulfur, selenium, tellurium or polonium. It is preferred that M is sulphur or silicon.

The value of N will depend on the source and nature of the compounds used in the synthesis of the compounds of the invention. It is preferred that N will be either 3 or 4. In particular it is preferred that N is 3 or 4 and K is 1.

In a particularly preferred embodiment M is sulphur and N is 4.

In a further preferred embodiment M is silicon and N is 3.

The compounds of the invention can also be present as the pharmaceutical acceptable salts as indicated in the diagrams above. Examples of pharmaceutical acceptable salts includes the sodium, potassium or calcium salts. The formation of the pharmaceutically acceptable salts is carried out in any of a number of ways well known in the art. In general, however, they are produced by reaction of the free acid form of the compound with base leading to exchange of acidic hydroxyl hydrogens with the base cation. As the compounds of the invention can have between 3 and 6 hydroxyl hydrogens they can be present as the mono-, di-, tri-, tetra-, penta-or hexa-substituted salt. It is particularly preferred that the salt is present as the sodium, potassium or calcium salt.

Particularly preferred compounds within the scope of the compounds of the invention are as follows : 1. Amino Tris Methyl Sulphate

2. Amino Tris Methyl Sulphate Trisodium 3. Amino Tris Methyl Silicate Trisodium

4. Phosphono Tris Methyl Sulphate.

5. Phosphono Tris Methoxy Sulphate 6. Phosphoro Tris Methoxy Sulphate Preferred compounds therefore include : (a) Amino Tris Methyl Sulphate (b) Amino Tris Methyl Sulphate Trisodium (c) Amino Tris Methyl Silicate

(d) Amino Tris Methyl Silicate Trisodium (e) Phosphono Tris Methyl Sulphate Phosphono Tris Methyl Sulphate Trisodium.

(g) Phosphono Tris Methoxy Sulphate (h) Phosphono Tris Methoxy Sulphate Trisodium (i) Phosphoro Tris Methoxy Sulphate (j) Phosphoro Tris Methoxy Sulphate Trisodium.

2. Synthesis of the Compounds of the Invention The compounds of the invention are typically synthesised in a two-step process as broadly shown in Schemes 1 and 2. Each of these steps may involve two or more alternative routes.

Scheme 1 wherein L is a leaving group.

(wherein Y is OH, H or a leaving group).

Scheme 2 wherein L is a leaving group.

(wherein Y is OH, H or a leaving group).

Step1. SynthesisofY-R-MOb The first step involves the monoalkylation of a mineral acid or mineral oxide acid or a derivative thereof to form a monoalkyl mineral acid or monoalkyl mineral acid oxide acid (or derivative thereof). Such a process is typically carried out as shown as shown in Scheme 3. (wheat R-L + MONHK+1 o Y-R-MONHK Scheme 3 The alkyl compound (R) used in the alkylation step of the mineral acid or mineral oxide acid can be any form of alkyl group that is suitably substituted or functionalised (by the L group) so as to provide functionality to allow it to react with the mineral acid. The R group will be chosen to provide the required R group in the finished product. The group R-L can be in the form of an alkyl group, an aldehyde group, an alkanoic acid group, or as an alkyl halide group such as alkyl chloride, alkyl fluoride, alkyl bromide or alkyl iodine. Whilst less effective the alkyl group could also originate from an alkene, an alkane or an alkyne group. It is preferred that the R-L group compound used in the reaction is either an aldehyde

compound or an alkyl chloride compound. Where the compound is an alkyl halide it is preferred that it is the di-halide as this provides functionality for both steps of the process.

The mineral acid or mineral oxide acid compound used in the alkylation reaction may be the partially or fully neutralized mineral or mineral acid or may be a partially halogenated derivative at any of the free hydroxyl groups. It is preferred that the mineral acid or mineral oxide acid is either the free acid or the mono-halogenated derivative.

The reaction of the two components can be carried out either neat or diluted in a suitable non-interfering solvent such as water, ethanol or hexane. The choice of solvent will depend on the nature of the reactive groups as some solvents are not compatible with all reactive groups. The reaction can be carried out by mere admixture of the two components or by stepwise addition of one of the components to the other (either neat or in solution). The mole ratio of alkyl compound to mineral acid or mineral oxide acid is typically of the order of 1: 1 however this may need to be varied slightly in certain circumstances such as where the components are not strongly reactive with each other. The reaction product of this process ie. the alkyl mineral acid or alkyl mineral oxide can be reacted immediately or can then be purified prior to further reaction.

There are two particularly preferred routes to make the group of formula Y-R- (MONHK) namely the aldehyde route and the halogenated organic route.

The Aldehyde route: This route will typically be used to produce most of branched organic compounds as the R in the structure of R- (MONHK).

The synthesis route is shown in Scheme 4: Scheme 4 Examples of typical compounds produced by this route are as follows : This route will produce branched intermediates that are predicted to increase the chelation capability of the final product, due to the complexity of molecular structure which provide more possible bonding site for the cation.

The Halogenated organic route This route will produce most of the straight chain intermediates or alkanoate type of intermediates.

For the synthesis, the procedure is to start with halogenated organic (R-hal) and react it in a two step procedure as shown in Scheme 5.

The synthesis route is: Scheme 5 Example : It is anticipated that the straight chain intermediate in the final product will show better microorganism cell wall penetration due to the structural simplicity compare to the branched intermediates.

Step 2. The synthesis of

The conversion of the alkyl mineral oxide to the compounds of the invention involves reaction of three mole equivalents of the alkyl mineral or alkyl mineral oxide compound with one mol of the hydride, hydroxy or oxyhydroxyl derivative of the desired V series element. Typically the initial source of alkyl group is such that the alkyl mineral oxide is functionalised for this step. When the desired product is the nitrogen derivative the suitable product is ammonia. Such a process is shown in Scheme 6 wherein the hydride is shown reacting. 3 R- (MONHK-l) + XH3 lo X- (R (MONHK-1)) 3 + 3HY 1 (2) Y Scheme 6 As with the previous step the two reactants can be contacted either neat or in a non-interfering solvent. They can be combined in suitable quantity by mere admixture or may be added such that one is slowly added to the other. It will be appreciated that the exact mode of formation of the compounds will depend on the nature of the intended final product.

The binding of the intermediate into V series element can produce some variation in the final product such as alkoxy type or aryloxy type depending on the V series compound used as the V series compound can be the hydride, hydroxyl or oxy-hydroxyl form.

1. Hydride ligand : this reaction will produce tris-alkyl/tris-aryl final product, either straight chain or branched.

The reaction is: /R-MONHK Reflux 8-10 hours XH3 + 3RMONHK-X R-MONHK + 3H2Y Y R-MONHK Scheme 7 Examples of this reaction are shown below : /R-MONHK Reflux 8-10 hours XH3 + 3RMONHK X R-MONHK + 3H2O OH R-MONHK T\'H The reaction is shown in Scheme 8: O-RMONHK Reflux 8-10 hours/ X (OH) 3 + 3RMONHK--X-O-RMONHK + 3H20 OH \p-RMONHK Scheme 8 Examples of this are as follows. O-CH20SO3H Reflux 8-10 hours/ P (OH) 3 + 3HOCH2OSO3H > pXO-CH2OSO3H + 3H20 O-CH2OSO3H 2 3 0 I I xO-CtOSiO2H U Reflux 8-10 hours/ 11 11 As (OH) 3 + 3HO-C---OSiO2H-O = As-O-C--OSiO2H \ ? 0 \O-C tOSiO2H U + 3H20 3. Oxy-hydroxyl ligand : this reaction will produce the oxy type of compound final products since the V series element will have 5 (five) bonding site rather than usual 3 (three) bonding site:

The reaction is shown in Scheme 9: Reflux 8-10 hours/ORMONHK O=X (OH) 3 + 3RMONHK O=X/O-RMONHK + 3H2O OH O-RMONHK N K Scheme 9 Examples are as follows - CH20S03H Reflux 8-10 hours/ O = P (OH) 3 + 3HOCH2OSO3H--O=P-O-CH2OSO3H + 3H2O O-CH20SO3H 0 O-C----OSiO2H J Reflux 8-10 hours/ O = As (OH) 3 + 3HO-C tOSiO2H~O = As-O-C--n--OSiO2H zu \ 11 ii O-CvOSiO2H + 3H20 The formation of one of the preferred compounds of the invention is shown in Scheme 10.

Scheme 10 3. DISPERSANT CAPABILITY The compounds of the present invention have strong capability to sequester inorganic cations, such as: Ca2+, Mg2+, Fe3+, and organic cation, such as: Quaternary Ammonium Cation, etc. by reaction to form a cheated complex. The compounds are thus useful in that they are able to prevent the interference of these ions with any system which contain ions of this type. The invention therefore provides a method of cheating metal ions in solution.

The following results indicate the cheating ability of the compounds of the invention which demonstrate the ratio as a weight ratio or stoichiometric molar ratio of amino tris methyl sulphate to some in-organics ions, such as Calcium & Magnesium ions.

In this test the dispersant ratio was determined using a gravimetric method by adding the tri-sodium salt of amino tris methyl sulphate at various weights into a CaCO3 suspension, weighing the precipitated solid after stabilization of the resultant suspension and comparing the result obtained to the result of a standard

and ethylene diamine tetra acetic acid-3 sodium (EDTA-3 Na) addition to the similar CaCO3 suspension (EDTA is known to have strong chelation ability).

MATERIALS AND APPARATUS Materials Reagent grade CaCO3 reagent grade EDTA-3 Na, reagent grade MgO, amino tris methyl sulphate trisodium salt.

Apparatus Petridish, Magnetic Stirrer, Glasswares, Electronic Scale Weight, Vacuum Filter Unit, electric Oven, Scanning Electron Microscope.

TEST METHODOLOGY 1. Determination of dispersant ratio: 1 a. Calcium Carbonate test: 0 Add 60 mg of CaCO3 into 1,000 ml of H20 ; make 21 of these suspensions in 1,000 ml glass beakers.

0 Beaker glass 1 will act as standard without any agent addition.

0 Into another 10 (ten) beaker glass, add EDTA-3 Na at various weight from 10 mg to 300 mg.

0 Into another 10 (ten) beaker glass, add amino tris methyl sulphate at various weight from 10 mg to 300 mg.

0 Stir the suspensions for half hour; stabilized for 24 (twenty four) hours time.

0 Separate the crystal after stabilization; dried and measure crystal weight.

1 b. Magnesium Oxide Test: 0 Add 20 mg of MgO into 1,000 ml of H20; make 21 (twenty one) the above suspension into 1,000 ml beaker glass.

0 Repeat methodology as for Calcium Carbonate test.

Table 1. First Calcium Carbonate Test Results No. g gCaCOs gofCaCOs gCaCOs g Mot ratio ligand added precipitated diluted CaCO3 Ca/ligand Added bond T diti Additi n f Amino Tris Methyl Su ! phate Trisodium fAdditio n _I k U 1 0 0.0601 0.0529 0.0072 0 0 2 0.0104 0.0602 0.0496 0.0106 0.0106 4.209423077 3 0.02 0.06 0.041 0.019 0.019 3.9235 4 0.0305 0.06 0.0461 0.0139 0.0139 1.882196721 5 0.041 0.0603 0.0443 0.016 0.016 1.611707317 6 0.0499 0.0602 0.0417 0.0185 0.0185 1.531162325 7 0.0605 0.0602 0.0396 0.0206 0.0206 1.406247934 8 0.0701 0.0602 0.0367 0.0235 0.0235 1.384522111 9 0.0805 0.0601 0.0343 0.0258 0.0258 1.323652174 10 0.0905 0.0605 0.0323 0.0282 0.0282 1.286917127 11 0.1005 0.0604 0.0308 0.0296 0.0296 1.21639801 EDTA 4 Na addition 1 0 0.0601 0.0529 0. 0072 0 0 2 0.01 0.0601 0.0506 0.0095 0.0095 3.9235 3 0.0201 0.06 0.0425 0.0175 0.0175 3.595771144 4 0.0302 0.06 0.0366 0.0234 0.0234 3.200066225 5 0.04 0.0601 0.0373 0.0228 0.0228 2.3541 6 0.0504 0.0601 0.0293 0.0308 0.0308 2.523888889 7 0.0603 0.0603 0.0274 0.0329 0.0329 2.253349917 8 0.0701 0.0603 0.0237 0.0366 0.0366 2.156319544 9 0.0802 0.0602 0.0277 0.0325 0.0325 1.673628429 10 0. 0905 0.0602 0.0209 0.0393 0.0393 1.793469613 11 0. 1005 0.0602 0.0192 0.041 0.041 1.684875622 Table 2. Second Calcium Carbonate test: No. g CaCO3 g of 9 CaCO3 | Mol ratio ligand added precipitated diluted CaCO3 Ca/ligand Added bond Amirio Tris Methyl Sulphate TrisodiumHddition up: Trisbd! Um,,,, i ion.:.... 1 0 0.0601 0.0544 0.0057 0 0 2 0.0104 0.06 0.0496 0.0104 0.0047 1.866442308 3 0.0213 0.0603 0. 046 0.0143 0.0086 1.667511737 4 0.031 0.06 0.0422 0.0178 0.0121 1.612032258 5 0.0401 0.06 0.0413 0.0187 0.013 1.338902743 6 0.051 0.0599 0.0329 0.027 0.0213 1.724882353 7 0.0605 0.0601 0.0379 0.0222 0.0165 1.126363636 8 0.0707 0.0603 0.0348 0.0255 0.0198 1.156633663 9 0.0802 0.06 0.0306 0.0294 0.0237 1.220461347 10 0.0902 0.06 0.0289 0.0311 0.0254 1.162993348 11 0.1004 0.06 0.0258 0.0342 0.0285 1.172360558 Table 3. Third Calcium Carbonate test: No. g of Michems A g MgO Mol ratio ligand CaCO3 precipitated 90 addition bond Mg/ligand Added added g MgO diluted Amino Tris Methyl Sulphate Trisodium\' 1 0 0.0206 0.0132 0.0074 0 2 0.005 0.02 0.0117 0.0083 0.0009 0.7434 3 0.0151 0.0208 0.012 0.0088 0.0014 0.382913907 4 0.0304 0.02 0.0085 0.0115 0.0041 0.557006579 5 0.05 0.0202 0.0089 0.0113 0.0039 0.32214 6 0.0699 0.0203 0.0085 0.0118 0.0044 0.259971388 7 0.0902 0.0205 0.0063 0.0142 0.0068 0.31135255 8 0.1004 0.0204 0.0047 0.0157 0.0083 0.341424303 9 0.1503 0.0203 0.0021 0.0182 0.0108 0.296766467 10 0.2001 0.0204 0.0002 0.0202 0.0128 0.264187906 11 0.25 0.0201-0.0011 0.0212 0.0138 0.227976 EDl\'A 4 Na. addition :.,,. ;.-.. : _ ; 1 0 0.0206 0. 0132 0.0074 0 0 2 0.0051 0.0205 0.0141 0.0064-0. 001-0.809803922 3 0.015 0.0204 0.0124 0.008 0.0006 0.1652 4 0.0308 0.0206 0.0093 0.0113 0.0039 0.522954545 5 0.0505 0.0205 0.0067 0.0138 0.0064 0.523405941 6 0.0705 0.0208 0.0063 0.0145 0.0071 0.415929078 7 0.0902 0.0201 0.0031 0.017 0.0096 0.439556541 8 0.1003 0.0205 0.0024 0.0181 0.0107 0.440588235 9 0.1501 0.0203-0.006 0.0209 0.0135 0.371452365 10 0.2001 0.0203-0.0023 0.0226 0.0152 0.313723138 11 0.2502 0.0205-0.0012 0.0217 0.0143 0.236047162

The results clearly show that the compound of the invention has comparable chelation ability to EDTA. This means that these compounds can be classified as strong cheating agents and thus would be useful at removing metal ions from solution (by chelation) and should be useful at removing metallic scale which builds up in pipes in industrial applications (by solubilising the insoluble materials).

The present invention in the further aspect therefore provides a method of cheating a metallic cation involving contacting a solution or suspension containing said metallic cation with a cheating effective amount of a cheating agent of the invention. In the step of contacting the compound of the invention can be added either directly to the solution containing the metallic cation or it can be added by itself as a solution in a further liquid. The amount of material required to adequately chelate the metallic cation will depend on the amount of metallic cation present. As noted, and as can be seen from the tables above, the compounds of the invention whilst having ability to chelate metallic cations generally chelate in a

1: 1 manner. Accordingly, in order to effectively chelate each mole of metallic cation present typically requires 1 mole of cheating agent to be added.

In yet a further aspect the present invention provides a method of solubilising metallic deposits including contacting said deposit with a compound of the invention. It is preferred that the step of contacting involves contacting the deposit with a solution containing a compound of the invention dissolved therein.

As would be appreciated, when dissolving metallic deposits it is sometimes necessary to use greater than 1 mole equivalents in order to achieve adequate solubilisation. Once again, this can be seen by reference to the tables above. In certain instances, it is also noted that the solubility increases with temperature. It is therefore preferred that said step of dissolving or solubilising a metallic deposit involves contacting said deposit with a heated solution containing a compound of the invention.

4. BIOCIDAL CAPABILITY The compounds of the invention have been found to have significant biocidal capability. Whilst not wishing to be bound by theory it is thought that the capability of the compounds to kill almost any microorganism, i. e., bacteria, algae, fungi, virus, etc. with some level of concentration operates by a mechanism of modifying the microorganism cell wall membrane from semi-permeable to totally permeable thus leading ultimately to cell death. It is though that this mechanism operates for all microorganisms which have a boundary membrane. For the microorganisms which do not have a boundary membrane of this type, the mechanism is though to involve direct reaction between the compounds with genetic material of the microorganism leading to death of the microorganism. The biocidal capability will be demonstrated by the following test data.

TEST PRINCIPLES Antibacterial activity was tested using disk-diffusion method by examining the clear zone of inhibition around the paper disks containing Amino Tris Methyl Sulphate. Growth curve is constructed by examining bacterial culture in broth media.

MATERIALS AND APPARATUS Materials Nutrient broth (Difco), nutrient agar (Difco), distilled water, Amino Tris Methyl Sulphate as test substance, glutaraldehyde, paraformaldehyde, bovine serum albumin (BSA), phosphate buffer pH 7,0.9% NaCI, resin LR white, toluidine blue, sodium citrate trihydrate, 0.1 N sodium hydroxide, uranyl acetate, lead nitrate, paraffin, transparent capsule, glass knives, grid, collodion, gold powder.

Apparatus Incubator, autoclave, Petri dish, Ose applicator, spectrophotometer (B&L), shaking incubator, glasswares, ultramicrotome, knife maker, light microscope, grid pad, transmission electron microscope (Philips), scanning electron microscope (Hitachi).

TEST MICROORGANISMS Staphylococcus aureus ATCC 6538, Escherichia coli ATCC 9637 supplied from Laboratory of Chemotherapy Department of Pharmacy ITB.

METHODS 1. Preparation of bacteria Bacteria were grown in nutrient broth, incubated for 24 hours at 37°C.

2. Preparation of test material Test material was diluted in distilled water in various concentrations. These were used to determine MIC and bacteriostatic/bactericide property.

3. MIC determination Using disk-diffusion method (in Petri dish), MlCs were determined against S. aureus and E. coli. The concentrations of test material were 10,000, 12,500,20,000,25,000,30,000,40,000 and 50,000 ppm. 20 pl of each concentration was impregnated into paper disks.

4. Determination of mode of action (bactericide/bacteriostatic property) Experiment was done in broth media containing test substance with concentration of 5,10 and 20% respectively. The turbidity of culture media was then measured every 30 minutes up to 270 minutes using spectrophotometer.

5. Preparation of microbial cells for electron microscopic examination.

S. aureus and E. coli were grown in liquid media for 24 hours, they then were mixed with Amino Tris Methyl Sulphate Trisodium to make its final concentrations of 0.6,5 and 10%. The systems were then shaking incubated for four hours. Microbial cells were separated and washed, first with 0.9% NaCI then with distilled water. The cells were used for the preparation in electron microscopy.

6. Preparation for electron microscopy (SEM) Bacterial cells were suspended in 4% collodion. The suspensions were then fixated to a plate of metal and coated with gold powder. These were then examined using scanning electron microscope and photographed.

7. Preparation for transmission electron microscope (TEM) a. Microbes prepared in 5) were fixed in 2% formaldehyde and 0.5% glutaraldehyde for two hours at 4°C. b. The systems were washed three times with phosphate buffer pH 7 and pre-embedded in bovine serum albumin (BSA) 1/5, while letting glutaraldehyde to harden at room temperature. c. After being dehydrated in alcohol, resin LR White was then infiltrated. d. Embedding was done in resin LR White followed by polymerization at 60°C for 48 hours. Hard-capsule-like polymerization products were then ready to be sectioned. e. Preparation of semi-thin and ultra-thin sections: Sections from microbial samples were prepared using automatic ultramicrotome. To obtain sections right at the samples, semi-thin sections were prepared and stained with toluidine blue and then examined under light microscope. When the exact sections had been obtained, ultra-thin sections were made and contrasted with uranyl acetate and lead citrate. Dry sections could then be examined using transmission electron microscope.

8. Effect of calcium ion on Amino Tris Methyl Sulphate Trisodium. a. 0.2 g of the test substance was diluted in 100 ml distilled water. 0.05 g calcium carbonate (analytical grade) was then added, and the solution was allowed to stand overnight. The forming precipitate was then separated and prepared for scanning electron microscopy. b. The same procedure in a) was done using 0.4 g Michems A-90 and 0.1 g calcium carbonate.

TEST RESULTS Minimal inhibitory concentration MIC of Amino Tris Methyl Sulphate Trisodium was 10,000 ppm and 12,500 ppm against E.coli and S. aureus respectively. This result is presented in Table 4.

Table 4 Antibacterial activity of Amino Tris Methyl Sulphate Trisodium No. Conc. Zone of inhibition (mm) (ppm) E. coli Average S. aureus Average 1 2, 000-- 2 4, 000 3 6, 000 4 8,000 - - - - - - - - 5 10, 000 7 7 7 7.00---- 6 12, 500 8.5 8. 5 8.5 8.50 7.5 7. 5 7.5 7.50 7 20, 000 9 9 9.3 9.10.13 8.5 8.5 8.5 8.50 8 25, 000 10.5 10.5 10.5 10.50 10 10 10 10.00 9 40, 000 12 12 12 12.00 12 11.9 11.8 11.90.09 10 50, 000 14 14 14 14.00 13.5 13.5 13.5 13.50

Table 5 Bacteriostatic and bactericide properties of Amino Tris Methyl Sulphate Trisodium against E. coli as tested using turbidimetric method Treatment Absorbance of the culture media at minute 0 30 60 90 120 150 180 210 Control 0.062 0.078 0.083 0.087 0.088 0.091 0.096 0.1 3,000 ppm 0.052 0.06 0.066 0.074 0.078 0.08 0.089 0.095 6,000 ppm 0.057 0.068 0.073 0.075 0.077 0.076 0.077 0.081 10,000 0.05 0.052 0.054 0.054 0.057 0.057 0.059 0.061 ppm Table 6 Bacteriostatic and bactericide properties of Amino Tris Methyl Sulphate Trisodium against S. aureus as tested using turbidimetric method

Treatment Absorbance of the culture media at minute 0 30 60 90 120 150 180 210 Control 0.054 0.063 0.065 0.072 0.075 0.083 0.092 0.099 3,000 ppm 0.059 0.066 0.072 0.075 0.078 0.082 0.084 0.087 6, 000 ppm 0.06 0.07 0.071 0.072 0. 074 0.074 0.076 0.082 10, 000 0.048 0.052 0.055 0.055 0.055 0.055 0.06 0.062 ppm Table 7 Bacteriostatic and bactericide properties of Amino Tris Methyl Sulphate Trisodium against E. coli as tested using turbidimetric method

Tr. Absorbance of the culture media at minute 0 30 60 90 120 150 180 210 240 270 Control 0.232 0.243 0.249 0.256 0. 261 0.268 0.271 0.273 0.279 0.285 5% 0.222 0.238 0.243 0.237 0.244 0.241 0.241 0.24 0.237 0.231 10% 0. 189 0. 194 0. 196 0. 199 0. 199 0. 195 0. 195 0. 195 0.186 0. 184 20% 0. 171 0. 178 0. 186 0. 194 0. 194 0. 186 0. 186 0.183 0. 176 0. 174 Table 8 Bacteriostatic and bactericide properties of Amino Tris Methyl Sulphate Trisodium against S. aureus as tested using turbidimetric method

Tr. Absorbance of the culture media at minute 0 30 60 90 120 150 180 210 240 270 Control 0.124 0.13 0.14 0.148 0.157 0.164 0.167 0.168 0.173 0.182 5% 0.13 0.141 0.144 0.142 0.145 0.146 0.153 0. 145 0.148 0.147 10% 0.132 0.135 0. 13 0.135 0. 141 0.136 0. 14 0. 142 0.138 0. 135 20% 0.122 0.127 0. 126 0. 131 0.131 0. 131 0.128 0. 127 0. 126 0. 125

The results clearly indicate that the compounds have bactericidal activity.

The compounds can thus be used to destroy bacteria in industrial or other applications. Thus in a further aspect the invention provides a method of eradicating a bacterial species comprising contacting said bacterial species with a biocidally effective amount of a compound of the invention. It is preferred that when used as a biocide the compounds of the invention are used as a dilute solution in water. This allows for their easy application.

The compounds of the invention can also, of course, be used as bacteriocides or biocides in methods of treatment of bacterial infections in humans. This can either be a treatment of bacterial infections of the surface of the body (i. e. as a method treatment of bacterial infections of cuts and abrasions to the skin or,) alternatively, can be administered as an oral pharmaceutical for treatment of bacterial infections in the human body per se. The preferred dosage form is the administration of the compounds as an aqueous solution of the salt.

The compounds of the invention have been found to have low toxicity effects on the human body and can be administered in any of a number of dosage forms to achieve the desired antibacterial effect. In addition, it is noted, that the exact dosage of the material will depend of course on the desired results to be achieved and, in addition, on the extent of the bacterial infection. The greater the bacterial infection, the greater the dosage required. The exact dosage level to be used will need to be determined by the skilled practitioner when assessing the patients medical condition.

The synthesis of a number of compounds of the invention will be demonstrated by the following examples.

Example 1-Synthesis of Amino Tris Methyl Sulphate Trisodium 66g of para formaldehyde was diluted in 65 ml. of water and the resultant slurry heated to 40-50°C. To this slurry was added dropwise 209g of 98% H2SO4.

The rate of addition was controlled to ensure a temperature of 50°C-100°C in the slurry. Upon completion of addition the solution is heated with agitation until a clear solution is achieved.

To this clear solution was added dropwise a solution of 73g NaOH in 70 ml with the rate of addition being controlled so that the temperature of the solution remained at 5010°C. Upon completion of addition the temperature was adjusted to ambient and 40g of a 25% solution of ammonia was added. The solution was then refluxed for 8-12 hours and then cooled to ambient temperature.

Evaporation of the solvent followed by crystallisation results in formation of the desired compound as an off white powder with the following properties MP> 600°C, BP> 1000°C, specific gravity = 2.37, water solubility 49.5%.

Example 2 66 g of p-CH20 (95%) was diluted in 65 cc of distilled water and the resultant slurry heated up to 50°C with agitation. Dropwise addition of 20% g H2SO4 (98%) into the slurry of p-CH20 was achieved through a separating funnel and the slurry temperature maintained at 50°C whilst the slurry was agitated. The slurry will slowly turn into clear solution and agitation continued until all liquid become clear solution. Upon completion of addition 68 g of liquid H3PO3 (85%)/phosphonic acid was added into solution, a reflux apparatus installed, and the solution heated to reflux 8-10 hours. After this time the condenser was removed, the solution boiled for 2 (two) hours to allow evaporation of solvent until 35-40% of volume evaporated. The solution was cooled down to ambient temperature slowly and then further cooled to 10°C by use of an ice water bath.

The resultant suspension was filtered to produce POTMS crystals, the POTMS crystals were then dried in the oven at 70-80°C until the constant crystal weight is achieved.