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WO 2017/009265 Al 19 January 2017 (19.01.2017) P O P C T

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WO 2017/009265 Al 19 January 2017 (19.01.2017) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/009265 Al 19 January 2017 (19.01.2017) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A01N 31/06 (2006.01) A01N 37/04 (2006.01) kind of national protection available): AE, AG, AL, AM, A0 37/00 (2006.01) A01P 1/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A0 37/02 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, PCT/EP2016/066368 KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (22) International Filing Date: MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 8 July 2016 (08.07.2016) PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (25) Filing Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 15 12 135.3 10 July 2015 (10.07.2015) GB GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: IPABC LTD [GB/GB]; The Die-Pat Centre, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, Broad March, Broad March, Daventry, Northamptonshire DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, NN1 1 4HE (GB). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors: SCHWARZ, Ulrich W; Am Weinberg 44, GW, KM, ML, MR, NE, SN, TD, TG). 23858 Rheinfeld (DE). SAILO-LEBEAU, Gracy; 7 Elm- hirst Road, Lutterworth, Leicestershire LEI 7 4PZ (GB). Published: (74) Agent: DEHNS; St Bride's House, 10 Salisbury Square, — with international search report (Art. 21(3)) London, Greater London EC4Y 8JD (GB). © (54) Title: BIODEGRADABLE ANTIMICROBIAL COMPOSITIONS AND USES THEREOF TO COMBAT MICROORGAN - ISMS (57) Abstract: The invention provides a method for combating contamination of a site with a microorganism, said method compris ing contacting the site and/or the microorganism with an antimicrobial aqueous composition comprising a decylglucoside at a con centration of about 2mM to about 40mM and at least one C i to Cs carboxylic acid, or a water-soluble salt thereof, at a concentration of about Ι µΜ to about lOOmM. The invention further provides such compositions, concentrated forms thereof, dry solid forms thereof and methods and kits for preparing such compositions Biodegradable antimicrobial compositions and uses thereof to combat microorganisms. The present invention relates to biodegradable antimicrobial compositions and uses thereof to combat microorganisms. More specifically there is provided a synergistic combination of a specific akylglycoside and low molecular weight carboxylic acids which, when combined in an aqueous formulation, exerts antimicrobial effects at concentrations at which no such activity is observed for the individual components. More specifically said formulations are aqueous compositions which comprise a decylglucoside at a concentration of as little as about 2mM and at least one C to C8 carboxylic acid, or a water-soluble salt thereof, at a concentration of as little as about 1µΜ. The invention therefore provides methods for combating the contamination of a site with a microorganism, particularly large scale industrial, agricultural, institutional and commercial sites, which comprise applying such compositions to such sites. As shown in the Examples, these concentrations of the components of the synergistic combination of the invention are the minimum concentrations having practical antimicrobial effects. Advantageously, the aqueous composition may be provided in a concentrated form which may be diluted with an aqueous diluent to closer to the minimum concentrations at or near the site of application prior to use, thereby minimising the cost and environmental impact of the composition itself and all parts of the production and supply chain. The site to be treated with the compositions of the invention may be in any context, and as such both medical and non-medical uses are provided. Also provided are dry solid, e.g. powder, compositions comprising amounts of a decylglucoside and at least one C to C8 carboxylic acid, or a water-soluble salt thereof, that following contact with a sufficient amount of an aqueous liquid provides the ready to use antimicrobial aqueous compositions of the invention. There is a continuing need to develop antimicrobial compositions that have the least impact on the environment possible. Such compositions must be highly effective so as to minimise the amount of antimicrobial compound (and any diluent or excipients) applied. Even if the diluent used is water, there is now pressure to minimise the use of this natural resource. The antimicrobial compounds (and other ingredients) should also be biodegradable, ideally readily so, and non-hazardous to higher organisms. Moreover, the manufacture of such compounds should involve natural compounds as source materials. From a cost perspective the more effective the composition the less must be used, thereby saving on materials costs and manufacturing and transport costs. The provision of concentrated forms, which may be diluted with an aqueous diluent to form a ready to use composition at or near the site of application prior to use, may further minimise the cost and environmental impact of the composition itself and all parts of the production and supply chain. Similarly ready mixed solid , e.g. powder, forms of the components of the compositions of the invention which may be dissolved in an aqueous diluent at or near the site of application prior to use in order to form a ready to use composition will also be a cost and environmentally effective option. Antimicrobial compositions comprising alkyl glycosides and bactericidally active carboxylic acids have been proposed in US 4920 100 on the basis of the apparent potentiation of the antibacterial effects of the carboxylic acid by the alkyl glycoside. In contrast, it has now been surprisingly found that the combination of a decylglucoside at concentrations at or just above the critical micelle concentration (CMC) of the decylglucoside (about 1.8 to about 2mM or about 300ppm) with extremely low concentrations of a low molecular weight carboxylic acid, e.g. lactic acid and/or citric acid results in a highly effective antimicrobial composition . Such concentrations of low molecular weight carboxylic acid are orders of magnitude lower than those proposed for use or used in US 4920 100. Thus in a first aspect the invention provides a method for combating contamination of a site with a microorganism, said method comprising contacting the site and/or the microorganism with an antimicrobial aqueous composition comprising: (i) a decylglucoside at a concentration of about 2mM to about 40mM, and (ii) at least one C to C8 carboxylic acid, or a water-soluble salt thereof, at a concentration of about 1µ Μ to about 100m M. The decylglucosides are a class of alkyl glycoside containing monomeric glucose as the glycone group and a 10 carbon saturated alkyl chain linked to the glucose residue via a glycosidic bond , e.g. an S-, N-, C-, or O-glycosidic bond . Preferably the decylcoside is decyl β-D-glucopyranoside. For convenience, references herein to the at least one C to C8 carboxylic acid include water-soluble salts thereof unless context dictates otherwise. The at least one C to C carboxylic acid may be a C to C C to C , or C to 8 6, 3 8 3 C6 carboxylic acid. The at least one C to C8 carboxylic acid may be an aliphatic or an aromatic carboxylic acid containing one or more carboxyl groups. Straight-chain or branched , saturated or unsaturated , unsubstituted or mono- or disubstituted acids may be used. The at least one C to C8 carboxylic acid may preferably monocarboxylic or dicarboxylic. Suitable substituents are SR (wherein R = H or C -3 alkyl, e.g. -CH 3), NR2 (wherein R2 is independently H or C -3 alkyl, e.g. -CH 3), CI, Br, N0 2 and OH. Preferably the at least one C to C8 carboxylic acid is an alpha hydroxy acid (AHA), e.g. lactic acid , citric acid, glycolic acid , malic acid, mandelic acid and tartaric acid. The at least one C to C8 carboxylic acid may for example be, e.g. lactic acid, citric acid, glycolic acid, malic acid , mandelic acid , tartaric acid , butyric acid , succinic acid , sorbic acid , isocitric acid, aconitic acid, propane-1 ,2,3- tricarboxylic acid, propionic acid , valeric acid , benzoic acid, oxalic acid or salicylic acid . Lactic acid and citric acid are preferred . If isomeric forms are available, any isomeric form or mixture thereof, e.g. racemic, may be used. In certain embodiments the L(+) isomer only is used, e.g. L(+) lactic acid . Water-soluble salts of the recited carboxylic acids are primarily alkali or alkali earth metal salts, of which the sodium, potassium and calcium salts are preferably used . Preferably the water-soluble salts are non-hazardous to humans and higher organisms, especially in the context of the medical uses of the invention . By "water soluble" it is meant that the salt can be dissolved to the required concentration in the antimicrobial aqueous composition .
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