US 20150.031762A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0031762 A1 Pimentel et al. (43) Pub. Date: Jan. 29, 2015

(54) ANTMICROBAL FORMULATIONS WITH Publication Classification PELARGONCACD (51) Int. C. (71) Applicant: ANITOX CORPORATION, A23L3/3463 (2006.01) LAWRENCEVILLE, GA (US) AOIN35/02 (2006.01) A6IL 2/6 (2006.01) (72) Inventors: Julio Pimentel, Buford, GA (US); Kurt AOIN37/02 (2006.01) Richardson, Maysville, GA (US) (52) U.S. C. CPC ...... A23L3/34635 (2013.01); A0IN37/02 (21) Appl. No.: 14/347,626 (2013.01); A0IN35/02 (2013.01); A61L 2/16 (2013.01); A23 V 2002/00 (2013.01) (22) PCT Fled: Oct. 8, 2012 USPC ...... 514/557 (86) PCT NO.: PCT/US 12/591.69 S371 (c)(1), (57) ABSTRACT (2) Date: Mar. 26, 2014 An antimicrobial composition for extending the shelf-life of Related U.S. Application Data water, feed or feed ingredients, comprising: water, a mixture (60) Provisional application No. 61/549,661, filed on Oct. of CrC18 organic acids, a mixture of CrC24 aldehydes, 5-25 20, 2011. wt.% pelargonic acid, and 5-30 wt.% trans-2-hexenal. US 2015/003 1762 A1 Jan. 29, 2015

ANTMICROBAL FORMULATIONS WITH 0011 Trans-2-hexenal is present in many edible plants PELARGONCACD Such as apples, pears, grapes, , kiwi, tomatoes, olives, etc. The use of plants and plant extracts have been RELATED APPLICATIONS Successful in studies looking for new anti-microbials. For 0001. This application claims priority to U.S. Provisional example, cashew apple was effective against Helicobacter application 6.1/549,661, filed 20 Oct. 2011, hereby incorpo pylori and S. cholerasuis (50-100 ug/ml). The two main com ponents were found to be anacardic acid and trans-2-hexenal. rated by reference. The minimum inhibitory activity and minimum biocidal BACKGROUND OF THE INVENTION activity of trans-2-hexenal were determined to be 400 and 800 ug/ml, respectively (Kubo, J.; Lee, J. R.: Kubo, I. Anti-Heli 0002 1. Field of the Invention cobacter pylori Agents from the Cashew Apple. J. Agric. 0003. An antimicrobial formulation consisting of a mix Food Chem. 1999, v. 47, 533-537: Kubo, I. And K. Fujita, ture of organic acids and aldehydes where Such combination Naturally Occurring Anti-Salmonella Agents. J. Agric. Food resulted in Synergistic response as compared to the addition of Chem. 2001, v. 49, 5750-5754). Kim and Shin found that high levels of the other component. trans-2-hexenal (247 mg/L) was effective against B. cereus, S. 0004 2. Background typhimurium, V parahaemolyticus, L. monocytogenes, S. 0005. The Centers for Disease Control and Prevention aureus and E. coli O157:H7 (Kim, Y. S.; Shin, D. H. Volatile (CDC) estimates that roughly one out of six Americans or 48 Constituents from the Leaves of Callicarpa japonica Thunb. million people are sickened by foodborne illnesses each year. and Their Antibacterial Activities.J. Agric. Food Chem. 2004, Another 128,000 are hospitalized and approximately 3,000 V. 52, 781-787). Nakamura. and Hatanaka (Green-leaf-de die of foodborne disease every year. In a 2011 report the CDC rived C6-aroma compounds with potent antibacterial action estimated that 20,000 cases of Salmonella resulted in hospi that act on both gram-negative and gram-positive bacteria. J. talization, and that 378 of these cases resulted in death. It has Agric. Food Chem. 2002, v. 50 no. 26, 7639-7644) demon also estimated that E. coli O157:H7 causes approximately strated that (3E)-hexenal was effective in controlling Staphy 62,000 cases of food borne disease and approximately 1,800 lococcus aureus, E. coli and Salmonella typhimurium at a food borne illness-related hospitalizations in the United level of 3-30 ug/ml. Trans-2-hexenal completely inhibited States. proliferation of both P. syringae pathovars (570 ug/L of air) 0006. A study by the Pew Charitable Trusts of George and E. coli (930 micrograms/L of air) (Deng, W.; Hamilton town University suggested that food borne illnesses cost the Kemp, T.: Nielsen, M.; Anderson, R.; Collins, G.; Hilder United States S152 billion in health-related expenses each brand, D. Effects of Six-Carbon Aldehydes and Alcohols on year. Bacterial Proliferation. J. Agric. Food Chem. 1993, V. 41. 0007 As the world trends toward more natural and/or 506-510). It was observed that trans-2-hexenal at 250 ug/ml organic antimicrobials, the need to find them has resulted in a was effective at inhibiting the growth of Phoma mycelium great amount of research, as well as increased cost for new (Saniewska, S. and M. Saniewski, 2007. The effect of trans raw materials due to the low commercial availability of these 2-hexenal and trans-2-nonenal on the mycelium growth of new natural/organic products. Phoma narcissi in vitro, Rocz. A R. Pozn. CCCLXXXIII, 0008 Formaldehyde has been use as an antiseptic for Ogrodn. V. 41, 189-193). In a study to control mold in fruits many years. Two patents, U.S. Pat. No. 5,547.987 and U.S. it was found that trans-2-hexenal was not phytotoxic to apri Pat. No. 5,591.467, teach the use of formaldehyde to control cots, but it was phytotoxic for peaches and nectarines at 40 Salmonella in animal feed. These patents do not suggest that uL/L (Neri, F., M. Mari, S. Brigati and P. Bertolini, 2007, a combination of formaldehyde and an organic acid would Fungicidal activity of plant Volatile compounds for control provide a synergistic effect, as described in the present inven ling Monolinia laxa in Stone fruit, Plant Disease V. 91, no. 1, tion. 30-35). Trans-2-hexenal (12.5 LL/L) was effective on con 0009 New antimicrobials have been found in many plants. trolling Penicillium expansium that causes blue mold (Neri, F.; These antimicrobials protect plants from bacterial, fungal, Mari, M.; Menniti, A.; Brigati, S.; Bertolini, P. Control of viral and insect infestation. These antimicrobials, which are Penicillium expansium in pears and apples by trans-2-hexenal components of the plant essential oils, can be acidic, alcohol vapours. Postharvest Biol. and Tech. 2006, V. 41, 101-108. or aldehyde-based chemicals. Neri, F.; Mari, M.; Menniti, A. M.; Brigati, S. Activity of 0010. One of the volatile compound used in this invention trans-2-hexenal against Penicillium expansium in Confer is trans-2-hexenal, which is six-carbon aldehyde with a con ence pears. J. Appl. Micrbiol. 2006, v. 100, 1186-1193). jugated double bond, CHO and MW=98.14. Aldehydes Fallik, E. et. al. (Trans-2-hexenal can stimulate Botrytis are represented by the general formula RCHO, where R is can cinerea growth in vitro and on Strawberries in vivo during be hydrogen oran aromatic, aliphatic or a heterocyclic group. storage, J. ASHS. 1998, v. 123, no. (5, 875-881) and Hamil They are moderately soluble in water and solubility decreases ton-Kemp, et. al. (J. Agric. Food Chem. 1991, V. 39, no. 5, as the molecular weight increases. Unsaturated aliphatic 952-956) suggested that trans-2-hexenal vapors inhibited the aldehydes includes, propenal, trans-2-butenal, 2-methyl-2- germination of Botrytis spores and apple pollen. butenal, 2-methyl-(E)-2-butenal, 2-pentenal, trans-2-hex (0012 US Published Application No. 2007/0087094 sug enal, trans-2-hexen-1-ol, 2-methyl-2-pentanal, 2-isopropyl gests the use of at least two microbiocidally active GRAS propenal, 2-ethyl-2-butenal, 2-ethyl-2-hexenal, (Z)-3- compounds in combination with less than 50% alcohol (iso hexenal, 3,7-dimethyl-6-octenal, 3,7-dimethyl-2,6- propanol or isopropanol/ethanol) as a microbicide. Trans-2- octadienal. (2E)-3,7-dimethyl-2-6-octadienal. (2Z)-3,7- hexenal could be considered one of the GRAS compounds dimethyl-2,6-octadienal, trans-2-nonenal, (2E,6Z)- (Schuer. Process for Improving the Durability of, and/or Sta nonadienal, 10-undecanal, 2-dodecenal, 2.4-hexadienal and bilizing, Microbially Perishable Products. US Published others. Application No. 2007/0087094). Also, Archbold et. al. US 2015/003 1762 A1 Jan. 29, 2015

observed that the use of 2-hexenal at 0.86 or 1.71 mmol (100 the cells, its C.f3-unsaturated aldehyde moiety reacts with or 200 microliters neat compound per 1.1 L container, respec biologically important nucleophilic groups. This aldehyde tively) for 2 weeks as for postharvest fumigation of seedless moiety is known to react with Sulphydryl groups mainly by table grapes showed promise for control of mold (Archbold, 1,4-addition under physiological conditions (Patrignani. F.; D.; Hamilton-Kemp, T.; Clements, A.; Collins, R. Fumigat Lucci, L.; Belletti, N.; Gardini, F. Guerzoni, M. E.; Lanciotti, ing Crimson Seedless Table Grapes with (E)-2-Hexenal R. Effects of sub-lethal concentrations of hexanal and 2-(E)- Reduces Mold during Long-term Postharvest Storage. Hort hexenal on membrane composition and volatile Science. 1999, v. 34, no. (4, 705–707). compounds of Listeria monocytogenes, Staphylococcus 0013 U.S. Pat. No. 5,698,599 suggests a method to inhibit aureus, Salmonella enteritidis and Escherichia coli. Interna mycotoxin production in a foodstuff by treating it with trans tional J. Food Micro. 2008, v. 123, 1-8). 2-hexenal. Trans-2-hexenal completely inhibited the growth 0016. It was suggested that the inhibition of Salmonella of A. flavus, P. notatum, A. alternate, F. Oxysporum, Cla typhimurim and Staphylococcus aureus by trans-2 hexenal is dosporium species, B. subtilis and A. tumerfaciens at a con due to the hydrophobic and hydrogen bonding of its partition centration of 8 ng/L air. When comparing trans-2-hexenal to in the bilayer. The destruction of electron transport sys citralin controlling yeast (10 CFU/bottle) in beverages it was tems and the perturbation of membrane permeability have found that 25 ppm of trans-2-hexenal and thermal treatment also been suggested as modes of action (Gardini. F.; Lanci (56°C. for 20 min) was equivalent to 100-120 ppm citral. In otti, R. Guerzoni, M. E. Effect of trans-2-hexenal on the beverages that were not thermally treated, 35 ppm of trans growth of Aspergillus flavus in relation to its concentration, 2-hexenal was necessary to stabilize them (Belletti, N.; Kam temperature and water activity. Letters in App. Microbiology. dem, S.; Patrignani, F.; Lanciotti, R.; Covelli, A.; Gardini, F. 2001, V. 33, 50-55). The inhibition of P expansum decay may Antimicrobial Activity of Aroma Compounds against Sac be due to damage to fungal membranes of germinating charomyces cerevisiae and Improvement of Microbiological conidia. (Neri. F.; Mari, M.; Menniti, A.; Brigati, S.; Berto Stability of Soft Drinks as Assessed by Logistic Regression. lini, P. Control of Penicillium expansium in pears and apples AEM. 2007, v. 73, no. 17, 5580-5586). Not only has trans-2- by trans-2-hexenal vapours. Postharvest Biol. and Tech. hexenal has been used as antimicrobial but also been observed 2006, v. 41, 101-108; Neri, F.; Mari, M.; Menniti, A. M.: to be effective in the control of insects. Volatiles (i.e. trans-2- Brigati, S. Activity of trans-2-hexenal against Penicillium hexenal) were effective against beetles such as Tibolium cas expansium in Conference pears. J. Appl. Micrbiol. 2006, V. taneum, Rhyzopertha dominica, Sitophilus granaries, Sito 100, 1186-1193). philus Orazyzae and Cryptolestes perrugineus (Hubert, J.; (0017 Studies have been performed to compare trans-2- Munzbergova, Z.; Santino, A. Plant volatile aldehydes as hexenal to similar compounds. Denget. al. showed that unsat natural insecticides against stored-product beetles. Pest urated Volatiles, trans-2-hexenal and trans-2-hexen-1-ol. Manag. Sci. 2008, v. 64, 57-64). U.S. Pat. No. 6,201,026 exhibited a greater inhibitory effect than the saturated vola (Hammond et al. Volatile Aldehydes as Pest Control Agents) tiles, hexanal and 1-hexanol (Deng, W.; Hamilton-Kemp, T.; Suggests of an organic aldehyde of 3 or more carbons for the Nielsen, M.; Anderson, R.; Collins, G.; Hilderbrand, D. control of aphides. Effects of Six-Carbon Aldehydes and Alcohols on Bacterial 0014 Several patents suggest the use of trans-2-hexenal as Proliferation. J. Agric. Food Chem. 1993, v. 41, 506-510). a fragrance or perfume. U.S. Pat. No. 6,596,681 suggests the Trans-2-hexenal was more active than hexanal, nonanal and use of trans-2-hexenal as a fragrance in a wipe for Surface trans-2-octenal againstall ATCC bacterial strains (Bisignano, cleaning. U.S. Pat. No. 6,387.866, U.S. Pat. No. 6,960,350 G.; Lagana, M. G.; Trombetta, D.; Arena, S.; Nostro, A.; and U.S. Pat. No. 7,638,114 suggest the use of essential oil or Uccella, N.; Mazzanti, G.; Saija, A. In vitro antibacterial terpenes (for example trans-2-hexenal) as perfume for anti activity of Some aliphatic aldehydes from Oleo europaea L. microbial products. U.S. Pat. No. 6,479,044 demonstrates an FEMS Microbiology Letters. 2001, V.198.9-13). Others have antibacterial Solution comprising an anionic Surfactant, a found that (E)-2-hexenal had lower minimal fungal-growth polycationic antibacterial and water, where an essential oil is inhibiting concentrations than hexanal, 1-hexanol, (E)-2- added as perfume. This perfume could be a terpene Such as hexen-1-ol, and (Z)-3-hexen-1-ol as determined for several trans-2-hexenal or other type ofterpenes. U.S. Pat. No. 6,323, species of molds, basically aldehydes>ketones-alcohols 171, U.S. Pat. No. 6,121,224 and U.S. Pat. No. 5,911,915 (Andersen, R. A.; Hamilton-Kemp, T.; Hilderbrand, D. F.; demonstrate an antimicrobial purpose microemulsion con McCraken Jr., C. T.; Collins, R. W.; Fleming, P. D. Struc taining a cationic Surfactant where an essential oil is added as ture—Antifungal Activity Relationships among Volatile C a perfume. This perfume can contain various terpenes includ and C. Aliphatic Aldehydes, Ketones, and Alcohols. J. Agric. ing trans-2-hexenal. U.S. Pat. No. 6,960,350 demonstrates an Food Chem. 1994, V. 42, 1563-1568). Hexenal and hexanoic antifungal fragrance where a synergistic effect was found acid were more effective than hexanol in inhibiting salmo when different terpenes were used in combinations (for nella (Kubo. I. And K. Fujita, Naturally Occurring Anti example trans-2-hexenal with benzaldehyde). Salmonella Agents. J. Agric. Food Chem. 2001, V. 49, 5750 0015 The mode of action of trans-2-hexenal is thought to 5754). be alteration of the cell membrane due to a reaction of the 0018 Muroi etal suggested that trans-2-hexenal exhibited unsaturated aldehyde with sulfhydryl or cysteine residues, or broad antimicrobial activity but its biological activity (50 to the formation of Schiffbases with amino groups in peptides 400 g/mL) is usually not potent enough to be considered for and proteins (Deng, W.; Hamilton-Kemp, T.: Nielsen, M.: practical applications (Muroi, H.; Kubo, A.; Kubo, I. Antimi Anderson, R.; Collins, G.; Hilderbrand, D. Effects of Six crobial Activity of Cashew Apple Flavor Compounds. J. Carbon Aldehydes and Alcohols on Bacterial Proliferation.J. Agric. Food Chem. 1993, v. 41, 1106-1109). Studies have Agric. Food Chem. 1993, V. 41, 506-510). Trans-2-hexenal is shown that trans-2-hexenal can potentiate the effectiveness of reported to act as a surfactant but it likely permeates by certain types of antimicrobials. Several patents suggest the passive diffusion across the plasma membrane. Once inside use of potentiators for aminoglycoside antibiotics (U.S. Pat. US 2015/003 1762 A1 Jan. 29, 2015

No. 5,663,152), and potentiators for polymyxin antibiotic 0024. Furfural, a cyclic aldehyde, is currently used as fun (U.S. Pat. No. 5,776,919 and U.S. Pat. No. 5,587,358). These gicide and nematicide but there are no reports of its use in potentiators can include indol, anethole, 3-methylindole, combination with an organic acid i.e., nonanoic acid, as dem 2-hydroxy-6-R-benzoic acid or 2-hexenal. A strong synergic onstrated in the present invention. effect was observed when trans-2-eptenal, trans-2-nonenal, 0025. Two aldehydes, n-decanal and nonanal were effec trans-2-decenal and (E.E)-2,4-decadienal were tested tive at controlling fungal growth (Dilantha Fernando, W. G., together (1:1:1:1 ratio) against ATCC and clinically isolated R. Ramaranthnam, A. Krihnamoorthy and S. Savchuck. Iden microbial strains (Bisignano, G.; Lagana, M. G.; Trombetta, tification and use of potential organic antifungal volatiles in D.: Arena, S.; Nostro, A.; Uccella, N.; Mazzanti, G.; Saija, A. biocontrol. Soil Biology and Biochemistry. 2005 v. 37,955 In vitro antibacterial activity of some aliphatic aldehydes 964) from Oleo europaea L. FEMS Microbiology Letters. 2001, V. 0026. The prior art has not suggested or observed that the 198, 9-13). use of aldehydes in combination with organic acids improved 0019 Humans are exposed daily to trans-2-hexenal the antimicrobial activity of either of the components by through consumption of food and beverages. Human expo themselves. It has suggested synergy with the combination of sures to trans-2-hexenal are ~350 ug/kg/day, with 98% essential oils and as potentiators of antibiotics. derived from natural sources and 2% from artificial flavoring. 0027 Commercial mold inhibitors and bactericides are It is unlikely that trans-2-hexenal would be toxic to humans composed of single organic or a mixture of organic acids and since toxic levels in rats are 30 times higher than normal formaldehyde. These acids are primarily propionic, benzoic intake by humans (Stout, M.D.; Bodes, E.; Schoonhoven, R.; acid, , acetic, and formic acid. Organic acids have Upton, P. B.; Travlos, G. S.; Swenberg, J. A. Toxicity, DNA been a major additive to reduce the incidence of food borne Binding, and Cell Proliferation in Male F344 Rats following infections. The mechanism by which small chain fatty acids Short-term Gavage Exposures to Trans-2-Hexenal. Soc. Toxi exert their antimicrobial activity is that undissociated cologic. Pathology Mar. 24 2008, 1533-1601 online). In (RCOOH-non-ionized) acids are lipid permeable and in this another rat Study, feeding trans-2-hexenal at dietary levels of way they can cross the microbial cell wall and dissociate in 0 (control), 260, 640, 1600 or 4000 ppm fed for 13 wk did not the more alkaline interior of the microorganism (RCOOH induce any changes in hematological parameters or organ >RCOO--H) making the cytoplasm unstable for survival. weights. At 4000 ppm there was a reduction in body weight (Van Immerseel, F. J. B. Russell, M. D. Flythe, I. Gantois, L. and intake, but it was not significant (Gaunt, I. F.; Colley, J. Timbermont, F. Pasmans, F. Haesebrouck, and R. Ducatelle. Acute and Short-term Toxicity Studies on trans-2-Hexenal. 2006. The use of organic acids to combat Salmonella in Fd Cosmet. Toxicol. 1971, v. 9, 775-786). poultry: a mechanistic explanation of the efficacy, Avian 0020 Even in fruits, twenty four hours to seven days expo Pathology. V.35, no. 3, 182-188: Paster, N. 1979. A commer Sure of pears and apples to trans-2-hexenal (12.5 LL/L did not cial study of the efficiency of and acid and affect fruit appearance, color, firmness, Soluble solids content calcium propionate as fungistats in poultry feed, Poult. Sci. V. or titratable acidity. In a trained taste panel, no significant 58,572-576). differences in the organoleptic quality of untreated and trans 0028 Pelargonic acid (nonanoic acid) is a naturally occur 2-hexenal treated “Golden Delicious” apples were observed, ring fatty acid. It is an oily, colorless fluid, which at lower while maintenance of off-flavors was perceived in “Bartlett', temperature becomes Solid. It has a faint odor compared to “Abate Fetel” and “Royal Gala' fruit (Neri, F.; Mari, M.: butyric acid and is almost insoluble in water. Pelargonic acid Menniti, A.; Brigati, S.; Bertolini, P. Control of Penicillium has been used as a non-selective . Scythe (57% expansium in pears and apples by trans-2-hexenal vapours. pelargonic acid, 3% related fatty acids and 40% inert mate Postharvest Biol. and Tech. 2006, 41, 101-108; Neri, F.; Mari, rial) is a broad-spectrum post-emergence or burn-down her M.; Menniti, A. M.; Brigati, S. Activity of trans-2-hexenal bicide produced by Mycogen/Dow Chemicals. The herbi against Penicillium expansium in Conference pears. J. Appl. cidal mode of action of pelargonic acid is due first to Micrbiol. 2006, v. 100, 1186-1193). membrane leakage during darkness and daylight and second 0021 Citral and cinnamaldehyde, have been found to be to peroxidation driven by radicals originating during daylight antifungal. The mode of action of these aldehydes is by react by sensitized chlorophyll displaced from the thylakoid mem ing with the sulfur group (—SH) from fungi (Ceylan E and D brane (B. Lederer, T. Fujimori. Y. Tsujino, K. Wakabayashi Fung. Antimicrobial Activity of Spices. J. Rapid Methods in and P Boger, 2004. Phytotoxic activity of middle-chain fatty Microbiology. 2004 v. 12, 1-55). acids II: peroxidation and membrane effects. Pesticide Bio 0022 U.S. Pat. No. 6,750.256 and RE 39543 suggest the chemistry and Physiology 80: 151-156). use of aromatic aldehydes like C-hexylcinnamic aldehyde for 0029 Chadeganipour and Haims (2001) showed that the the control of ant population but does not suggest any syner minimum inhibitory concentration (MIC) of medium chain gistic effect of the aldehyde in combination with a organic fatty acids to prevent growth of M. gypseum was 0.02 mg/ml acid to improve effectiveness or a reduction on the active and for pelargonic acid 0.04 mg/ml on Solid media ingredient or their effectiveness on bacterial control. and 0.075 mg/ml capric acid and 0.05 mg/ml pelargonic in 0023 The essential oil of Coriandrum sativum contains liquid media. These acids were tested independently and not 55.5% of aldehydes which has been effective on preventing as a mixture (Antifungal activities of pelargonic and capric growth of gram positive and gram negative bacteria. These acid on Microsporum gypseum Mycoses V. 44, no 3-4, 109 aldehydes include: n-octanal, nonanal. 2E-hexenal, decanal, 112). N. Hirazawa, et. al. (Antiparasitic effect of medium 2E-decenal, undecenal, dodecanal, 2E-dodecenal, tridecanal, chain fatty acids against ciliated Crptocaryon irritans infes 2E-tridecene-1-aland 3-dodecen-1-all (Matasyoh, J. C., Z. C. tation in the red sea bream Pagrus major; 2001, Aquaculture Maiyo, R. R. Ngure and R. Chepkorir. Chemical Composition v. 198, 219-228) found that nonanoic acid as well as C6 to and Antimicrobial Activity of the Essential Oil of Corian C10 fatty acids were effective in controlling the growth of the drum sativum. Food Chemistry. 2009 v. 113,526-529). parasite C. irritans and that C8, C9 and C19 were the more US 2015/003 1762 A1 Jan. 29, 2015

potent. It was found that Trichoderma harzianum, a biocon sized that synergistically improve the antimicrobial capacity trol for cacao plants, produces pelargonic acid as one of many of these compounds by the addition of organic acids espe chemicals, which was effective in controlling the germination cially nonanoic acid. and growth of cacao pathogens. (MAneja, T. Gianfagna and P. Hebbar, 2005). SUMMARY OF THE INVENTION 0033. One object of the present invention is to provide a 0030 Several US patents disclose the use of pelargonic composition that synergistically improves the microbicidal acids as fungicides and bactericides: US Published Applica effect of organic acids and aldehydes. tion 2004/026685 discloses a fungicide for agricultural uses 0034. The composition can be a solution comprising of an that is composed of one or more fatty acids and one or more organic acid or a mixture of several organic acids in combi organic acids different from the fatty acid. In the mixture of nation of aldehydes. the organic acids and the fatty acids, the organic acid acts as 0035. The composition can further comprise a volatile a potent synergist for the fatty acid to function as a fungicide. aldehyde resulting from the lipoxygenase pathway. U.S. Pat. No. 5,366,995 discloses a method to eradicate fun 0036. The aldehydes of the composition comprise butyral galand bacterial infections in plants and to enhance the activ dehyde, undecylenic aldehyde, citral, decanal, decenal, 2-4- ity of fungicides and bactericides in plants through the use of decadienal and otheraldehydes from C1 to C24 carbon length fatty acids and their derivatives. This formulation contains or shape. 80% pelargonic acid or its salts for the control of plants fungi. 0037. The organic acids of the composition comprise The fatty acids used are primarily C9 to C18. U.S. Pat. No. organic acids of 1 to 24 carbon chain length, Saturated, unsat 5.342,630 discloses a novel pesticide for plant use containing urated, cyclic or other organic acid. an inorganic salt that enhance the efficacy of C8 to C22 fatty 0038. The effective mixture of the invention comprising 1 acids. One of the examples shows a powdered product with to 70% by volume organic acids, 2% pelargonic acid, 2% capric acid, 80% talc, 10% sodium 0039. The effective mixture of the invention comprising 0 carbonate and 5% potassium carbonate. U.S. Pat. No. 5,093, to 70% by volume pelargonic acid. 124 discloses a fungicide and arthropodice for plants com 0040. The effective mixture of the invention comprising 5 prising of alpha mono carboxylic acids and their salts. Pref to 50% aldehyde. erably the fungicide consists of the C9 to C10 fatty acids, 0041. The effective mixture of the invention comprising 0 partially neutralized by active alkali metal Such as potassium. to 70% by volume water. The mixture described consists of 40% active ingredient dis 0042. The composition is effective against various fungi solved in water and includes 10% pelargonic, 10% capric acid present in feed and major feed ingredients. and 20% coconut fatty acids, all of with are neutralized with 0043. The composition is effective against various bacte potassium hydroxide. U.S. Pat. No. 6,596.763 discloses a ria present in feed and major feed ingredients. method to control skin infection comprised of C6 to C18 fatty 0044) The composition is effective against various bacte acids or their derivatives. U.S. Pat. No. 6,103,768 and U.S. ria and fungi present in water. Pat. No. 6,136,856 discloses the unique utility of fatty acids 0045. The composition is effective against microbes det and derivatives to eradicate existing fungal and bacterial rimental for the production of alcohol from fermentation of infections in plants. This method is not preventive but showed cellulose, starch or Sugars. effectiveness in already established infections. Sharpshooter, a commercially available product, with 80% pelargonic acid, DESCRIPTION OF THE PREFERRED 2% emulsifier and 18% surfactant showed effectiveness EMBODIMENTS against Penicillium and Botrytis spp. U.S. Pat. No. 6,638,978 0046. In this specification and in the claims which follow, discloses an antimicrobial preservative composed of a glyc reference will be made to a number of terms which shall be erol fatty acid , a binary mixture of fatty acids (C6 to defined to have the following meanings. C18) and a second fatty acid (C6 to C18) where the second fatty acid is different from the first fatty acid for preservation Definitions of food. WO 01/97799 discloses the use of medium chain fatty acids as antimicrobials agents. It shows that an increase 0047 A“volume percent of a component is based on the of the pH from 6.5 to 7.5 increased the MIC of the short chain total volume of the formulation or composition in which the fatty acids containing 6-8 carbons chain. component is included. 0048. An organic acid of the composition can comprise 0031) Pelargonic acid is used as a component of a food formic, acetic, propionic, butyric, pelargonic, lactic and other contact surface sanitizing solution in food handling establish C. to C fatty acid or mono-, di-, or triglycerides containing ments. A product from EcoLab consist of 6.49% pelargonic C to C fatty acids. These fatty acids comprising small acid as active ingredient to be use as a sanitizer for all food chain, medium chain, long chain fatty acids or Small chain, contact surfaces (12CFR178.1010 b). The FDA has cleared medium chain, long chain triglycerides. pelargonic acid as a synthetic food flavoring agent (21 CFR 0049. The term “effective amount of a compound means 172.515), as an adjuvant, production aid and sanitizer to be anh amount capable of performing the function of the com used in contact food (12 CFR 178.1010b) and in washing or pound or property for which an effective amount is expressed, to assist in lye peeling of fruits and vegetables (12 CFR Such as a non-toxic but sufficient amount of the compound to 173.315). Pelargonic acid is listed by the USDA under the provide the desired antimicrobial benefits. Thus an appropri USDA list of Authorized Substances, 1990, section 5.14, ate effective amount may be determined by one of ordinary Fruit and Vegetable Washing Compounds. skill in the art using only routine experimentation. 0032. The present invention relates only to the use of some 0050 Formulations can vary not only in the concentration of the aldehydes extracted from plants or chemically synthe of major components i.e. organic acids, but also in the type of US 2015/003 1762 A1 Jan. 29, 2015

aldehydes and water concentration used. This invention can TABLE 1 be modified in several ways by adding or deleting from the formulation the type of organic acid and aldehyde. Interaction of Pelargonic acid and formaldehyde 0051. By the terms “synergistic effect or synergy' of the Formaldehyde Pelargonic acid Salmonella composition is meant to the improved the preservative effect Test Product (%) (%) % reduction when the ingredients are added as a mixture rather than as Control O O O individual components. Formaldehyde O.O2S O 90.8 0052 Composition (s) O.O12S O 59.0 0053 A composition of the present invention comprises O.OO625 O 39.3 O.OO312 O 17.3 an effective amount of organic acids of 1 to 24 carbons chain Pelargonic acid O O.OO2S O and an aldehyde. O O.OO12S O 0054 The composition can comprise 1 to 100% by vol O O.OOO625 O ume organic acids, 0 to 99% by volume , 0 to 99% O O.OOO312 O HCHO: Pelargonic O.O2S O.OO2S 94.2 by volume propionic acid, 0 to 99% lactic acid, 0 to 99% O.O12S O.OO2S 61.0 pelargonic acid. The composition can comprise 0 to 99% O.OO625 O.OO2S 40.7 water. The composition can comprise 0 to 99% of otheralde O.OO312 O.OO2S 26.1 hyde. O.O2S O.OO12S 92.5 O.O12S O.OO12S 52.5 O.OO625 O.OO12S 38.6 Methods O.OO312 O.OO12S 27.8 O.O2S O.OOO625 83.1 0055. The present invention is effective against bacteria O.O12S O.OOO625 54.6 and fungi. O.OO625 O.OOO625 45.4 0056. The present invention is applied to water. O.OO312 O.OOO625 18.6 O.O2S O.OOO312 90.2 0057 The present invention is applied to the raw mate O.O12S O.OOO312 57.6 rial before entering the mixer. O.OO625 O.OOO312 39.7 0058. The present invention is applied to the unmixed O.OO312 O.OOO312 22.7 raw materials in the mixer. 0059. The present invention is applied during the mix ing of the raw ingredients. 0066. A dose response curve was observed with formal 0060. The present invention is applied in liquid form or dehyde and the formaldehyde: pelargonic acid treatments. as a dry product mixed with a carrier. Pelargonic acid at the highest dose tested was not bacteri 0061 The present invention is applied is such a form cidal. Pelargonic acid at 0.00125 and 0.0025% did appear to that provides a uniform and homogeneous distribution increase the effectiveness of formaldehyde. of the mixture throughout the feed. 0062 One of the objectives of the present invention is to Example 2 control the level of microbes in feed and feedstuffs. Several 0067 Formaldehyde and/or pelargonic acid were added to mixtures of organic acids and aldehydes resulted in several test tubes at concentrations shown in Table 2. Solutions were formulations that showed effectiveness against bacteria in vortexed for 10 seconds to ensure mixing. There were three buffer and feed. Other objective of the present invention is to replicate tubes per treatment. A Suspension of Salmonella formulate an antimicrobial with natural occurring com typhimurium (10 cfu/ml, ATCC #14028) was added to three pounds or safe to use compounds. All of the chemicals used in test tubes containing each formulation. The Solutions were the present invention are currently approved for human uses vortexed, incubated at room temperature for 24 hours and as antimicrobials, flavor enhancers and perfumery. plated on SMA (Standard Methods Agar) for 24 hours before 0063. There were unexpected results, i.e. synergism and counting Salmonella colonies. The effectiveness of each for additive effect, when the organic acids and aldehydes were mulation as a percent reduction compared to its control value used. is shown in the following table. 0064. Throughout this application, various publications are referenced. The disclosures of these publications in their entireties are hereby incorporated by reference into this appli TABLE 2 cation in order to more fully describe the state of the art to Interaction of pelargonic acid and formaldehyde which this invention pertains. Formaldehyde Pelargonic acid Salmonella Example 1 Test Product (%) (%) % reduction Control O O O 0065 Formaldehyde and/or pelargonic acid were added to Formaldehyde O.O2S O 88.3 test tubes at concentrations shown in Table 1. Solutions were O.O12S O 50.5 O.OO625 O 41.O vortexed for 10 seconds to ensure mixing. There were three O.OO312 O 17.7 replicate tubes per treatment. A suspension of Salmonella Pelargonic acid O O.O1 100 typhimurium (10 cfu/ml, ATCC #14028) was added to three O O.OOS 96.5 test tubes containing each formulation. The Solutions were O O.OO2S 8.8 vortexed, incubated at room temperature for 24 hours plated O O.OO12S 2.1 HCHO: Pelargonic O.O2S O.O1 100 on SMA (Standard Methods Agar) for 24 hours before count O.O2S O.OOS 98.6 ing Salmonella colonies. The effectiveness of each formula O.O2S O.OO2S 97.2 tion as a percent reduction compared to its control value is O.O2S O.OO12S 91.9 shown in the following table. US 2015/003 1762 A1 Jan. 29, 2015

TABLE 2-continued 0071 Pelargonic acid at 10% increases the efficacy of trans-2-hexenal. Interaction of pelargonic acid and formaldehyde Formaldehyde Pelargonic acid Salmonella Example 4 Test Product (%) (%) % reduction O.O12S O.O1 100 0072 Three formulations from study 3 were chosen to test O.O12S O.OOS 100 their effectiveness against Salmonella typhimurium (ATCC O.O12S O.OO2S 62.9 O.O12S O.OO12S 37.8 #14028) in feed. Poultry mash feed was amended with a meat O.OO625 O.O1 100 and bone meal inoculum of Salmonella typhimurium at a level O.OO625 O.OOS 99.6 of 10 cfu/g offeed. Contaminated feed was then treated with O.OO625 O.OO2S 20.8 O.OO625 O.OO12S 38.2 either 0, 1.5 or 2 kg/MT of the formulations listed below. O.OO312 O.O1 100 After 24 hours, 10 g of subsamples of the untreated and O.OO312 O.OOS 97.2 treated feed were suspended in 90 ml Butterfield buffer. Dilu O.OO312 O.OO2S 36.0 tions were plated on XLT-4 agar and incubated at 37°C. for 48 O.OO312 O.OO12S 0.4 hours before counting Salmonella colonies. Additional samples were taken at 7 days after treatment for Salmonella 0068 A dose response curve was observed with formal enumeration. The formulas used are shown in the following dehyde, pelargonic acid and the formaldehyde:pelargonic table. acid treatments. Pelargonic acid at 0.0012.5% and 0.0025% did not have a significant impact on Salmonella reduction. TABLE 5 However, when these levels of pelargonic acid were mixed with formaldehyde, the bactericidal efficacy of formaldehyde CHEMICAL FORMULATIONS (90) was improved. Chemical 1 2 3 Acetic acid 2O 2O 2O Example 3 Propionic acid 50 50 50 Pelargonic acid 5 10 15 0069. Five formulations were prepared for in vitro studies Trans-2-hexenal 25 2O 15 as presented in Table 3. Formulations were added to test tubes at concentrations of 0.01% and 0.05%. Solutions were vor Total 1OO 1OO 1OO texed for 10 seconds to ensure mixing. There were three replicate tubes per treatment. 0073 Results: The following table shows that all formu TABLE 3 lations were effective against Salmonella. Increasing the level of pelargonic acid resulted in similar efficacy as high level of Chemical Composition of Product Formulas (% hexenal. Chemical 1 2 3 4 5 TABLE 6 Acetic acid 2O 2O 2O 2O 2O Propionic acid 50 50 50 50 50 Effect of Chemicals on Salmonella at 1 and 7 Days Post-Treatment Pelargonic acid 5 10 15 2O 25 Trans-2-Hexenal 25 2O 15 10 5 % Reduction % Reduction Treatment Kg/MT at 1 Day at 7 Day TOTAL 1OOO 1OO.O 1OOO 1OOO 1OO.O Control O O O Formula ii.1 1.5 85.0 97.4 2 93.8 98.9 I0070) A suspension of Salmonella typhimurium (10 cfu/ Formula ii.2 1.5 75.6 94.3 ml) was added to three test tubes containing the different 2 98.0 99.6 dilutions of each formulation. The tubes were vortexed, incu Formula i3 1.5 90.6 92.1 bated at room temperature for 24 hours and then the solution 2 91.8 96.6 was plated on SMA (Standard Methods Agar) for 48 hours before counting Salmonella colonies. The effectiveness of each formulation is reported as a percent reduction compared to its control value as is shown in the following table. Example 5 0074 The five formulations used in Example 3 were cho TABLE 4 Sen to test their effectiveness against Salmonella typhimu Percent Saimoneia Reduction rium. Poultry mash feed was amended with a meat and bone meal inoculum of Salmonella typhimurium. Contaminated O.01% O.05% feed was then treated with either 0 or 2 kg/MT of the formu Treatment Dilution Dilution lations. After 24 hours, 10 g of subsamples of the treated feed Formula 1 80.6 100 were suspended in 90 ml Butterfield buffer. Dilutions were Formula 2 73.O 99.5 Formula 3 52.3 97.7 plated on XLT-4 agar and incubated at 37° C. for 48 hours Formula 4 41.4 96.8 before counting Salmonella colonies. Additional samples Formula 5 18.9 93.7 were taken 7 days after treatment for Salmonella enumera tion. The following table shows that all formulations were effective against Salmonella. US 2015/003 1762 A1 Jan. 29, 2015 7

TABLE 7 TABLE 8 Effect of Chemicals on Salmonella at 1 and 7 Days Post-Treatment Evaluating the Synergism of Pelargonic acid and Hexenal on Residual Activity in Treated Feed % Reduction % Reduction Treatment at 24Hours at 7 Days % Reduction Treatment at 13 Days Control O O Formula 1 90.0 96.6 Control O Formula 2 92.6 97.6 Hexenal: pelargonic mixture 93.5 Formula 3 86.1 91.0 (0.25 kgton hexenal) Formula 4 47.3 76.5 0.10 kg?ton hexenal O Formula 5 55.1 66.7 0.25 kg/ton hexenal O 0.50 kg?ton hexenal 77.4 1.00 kg?ton hexenal 87.1 0075 Equal concentration of Pelargonic acid and trans-2- hexenal resulted in similar effectiveness as high levels (25%) 0078. The addition of pelargonic acid (5%) to trans-2- trans-2-hexenal. hexenal resulted in better effectiveness against Salmonella than trans-2-hexenal by itself. Example 6 Example 7 0079. Seven aldehydes (butVraldehyde, citral, unde 0076 FormulaO 1 from Example 3 composedO of 25% trans- cylenic aldehyde, decadienal,y ( cinnamaldehyde,ly yde, decanals and 2-hexenal, 5% pelargonic acid and 70% aqueous organic furfural) were blended with trans-2-hexenal, pelargonic acid, acids was compared to trans-2-hexenal for residual activity in - - - O feed. Poultry mash feed was treated with 0.1, 0.25, 0.5 or 1.0 propionic acid andO acetic acid as presented in Table 9. A 20% kg/ton of hexenal compared to 1 kg/ton of the hexenal: pel (X-1) and a 25% (F18) hexanal: organic acid product were ic acid binati duct (0.25 kg/ton ofh 1). At included as positive controls. Formulations were added to test argon1c ac1d comb1nauon product (U. on Oi nexena), tube at concentration of 0.1%, 0.05%, 0.01% and 0.005%. 1, 6 and 13 days post treatment, feed was contaminated with Solutions were vortexed for 10 seconds to uniformly mix the a meat and bone3. meal inoculum of Salmonella typhimurium solution. There were three replicate tubes per treatment. A at a level of 10 cfu/g of feed. After 24 hours, 10 g of sub- suspension of Salmonella typhimurium (10"4 cfu/ml) was samples of the untreated and treated feed were suspended in added to three test tubes containing the different dilution- of 90 ml Butterfield buffer.O Dilutions were plated onXLT-4 agar each formulation. The solutions were vortexed, incubated at and incubated at 37°C. for 48 hours before counting Salmo room temperature for 24 hours and then plated on XLT-4 agar nella colonies. for 48 hours before counting Salmonella colonies. 0077. The following table compares the impact of pelar- 0080. The effectiveness of each formulation as percent gonic acid on the residual activity of hexenal against Salmo- reduction compared to the control value is shown in the fol nella. lowing tables. TABLE 9 Effect of Butyraldehyde, Hexenal and Pelargonic Acid on Salmonella

FORMULAS F18 X-1 6S 66 67 68 69 70 71 72 73 74

Pelargonic acid 5 10 5 5 5 5 5 10 10 10 10 10 Acetic acid (56%) 20 20 20 20 20 20 25 15 15 15 15 20 2-hexenal 2S 20 20 15 10 5 O 20 15 10 5 O Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 Butyraldehyde S 10 15 20 20 S 10 15 20 20 1OO 100 100 100 100 100 100 100 100 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X-1 65 66 67 68 69 70 71 72 73 74

O.OOS9/o 26.7 212 26.7 9.1 42 O O 9.1 15.2 12 O O O.01% 70.9 52.1 44.8 40.O. 11.5 O O 67.3 38.2 6.7 O O O.05% 1OO 100 100 100 94.5 69.7 O 1 OO 99.4 95.2 77.0 O

TABLE 10 Effect of Citral, Hexenal and Pelargonic Acid on Salmonella

FORMULAS F18 X-1 7S 76 77 78 79 80 81 82 83 84

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 20 20 20 20 20 20 20 20 25 15 15 2-hexenal 2S 20 25 20 10 20 15 10 5 O 20 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 US 2015/003 1762 A1 Jan. 29, 2015

TABLE 10-continued

citral 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 100 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X-1 75 76 77 78 79 8O 81 82 83 84

O.OO5% 26.7 212 23.6 33.9 44.8 43.O 29.1. 19.4 45.5 36.4 37.0 38.2 O.01% 70.9 52.1 70.3 63.O 63.O 77.0 33.3 68.5 60.6 60.6 S3.3 30.9 O.05% 1OO 100 100 100 100 100 90.9 100 100 100 100 94.5

TABLE 11 Effect of Undecylenic, Hexenal and Pelargonic Acid on Salmonella

FORMULAS F18 X-1 95 96 97 98 99 1OO 101 102 103 104

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 2O 2O 2O 2O 2O 2O 2O 2O 25 15 15 2-hexenal 25 2O 25 2O 10 2O 15 10 5 O 2O 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 undecylenic 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 100 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X-1 F95 F96 F97 F98 F99 F100 F101 F102 F1O3 F104

O.OO5% O O 5.9 20.1 29.6 47.2 85.1 16.1. 14.7 21.5 SO.6 29.6 O.01% 38.4 19.S 60.7 S2.6 74.3 79.7 9 O.S 49.2. 69.S. 41.1 S19 62.1 O.05% 1OO 100 99.3 100 100 100 98.6 100 100 100 99.3 89.8

TABLE 12 Effect of Decadienal, Hexenal and Pelargonic Acid on Salmonella

FORMULAS F18 X-1 85 86 87 88 89 90 91 92 93 94

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 2O 2O 2O 2O 2O 2O 2O 2O 25 15 15 2-hexenal 25 2O 25 2O 10 2O 15 10 5 O 2O 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 24 decadieneal 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 100 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X-1 85 86 87 88 89 90 91 92 93 94

O.OO5% O O 74.3 72.9 83.1 70.2 79.7 49.2 81.7 87.8 90S 93.9 O.01% 38.4 19.5 98.0 94.6 93.2 92.6 96.6 91.9 99.3 98.6 99.3 91.2 O.05% 1OO 100 100 100 100 100 100 100 100 100 100 100

TABLE 13 Effect of Cinnamaldehyde, Hexenal and Pelargonic Acid on Salmonella

FORMULAS F18 X-1 1 OS 106 107 108 109 110 111 112 113 114

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 2O 2O 2O 2O 2O 2O 2O 2O 25 15 15 2-hexenal 25 2O 25 2O 10 2O 15 10 5 O 2O 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 cinnamaldehyde 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 100 100 100 100 US 2015/003 1762 A1 Jan. 29, 2015

TABLE 13-continued % Reduction of Salmonella Growth

Concentration F18 X1 F105 F106 F107 F108 F109 F110 F111 F112 F113 F114

O.OO5% S.O.3 29.9 31.O 39.9 26.8 S.9 21.6 31.5 24.7 22.6 37.8 23.1 O.01% 733 SO3 S9.2 62.9 44.6 45.6 18.4 66.O SS.6 57.1 45.6 15.3 O.05% 1OO 100 100 1OO 100 100 84.8 100 1 OO 100 100 90.6

TABLE 1.4 Effect of Decanal, Hexenal and Pelargonic Acid on Salmonella FORMULAS F18 X-1 115 11 6 117 118 119 120 121 122 123 124

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 2O 2O 2O 2O 2O 2O 2O 2O 25 15 15 2-hexenal 25 2O 25 2O 10 2O 15 10 5 O 2O 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 decanal 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 1 OO 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X1 F11S F116 F117 F118 F119 F120 F121 F122 F123 F124

O.OO5% S.O.3 29.9 39.9 47.2 56.6 77.5 88.S 51.9 45.1 70.7 92.7 91.6 O.01% 733 SO3 61.8 89.0 93.7 94.2 94.8 67.6 744 86.9 93.2 94.8 O.05% 1OO 100 100 100 100 100 97.4 100 1 OO 100 100 97.4

TABLE 1.5 Effect of Furfural, Hexenal and Pelargonic Acid on Salmonella FORMULAS F18 X-1 12S 126 127 128 129 130 131 132 133 134

Pelargonic acid 5 10 5 10 5 5 5 5 5 5 10 10 Acetic acid (56%) 20 2O 2O 2O 2O 2O 2O 2O 2O 25 15 15 2-hexenal 25 2O 25 2O 10 2O 15 10 5 O 2O 15 Propionic acid 50 50 50 50 50 50 50 50 50 50 50 50 furfural 5 10 15 2O 2O 5 10 15 2O 2O 1OO 100 100 100 100 100 100 100 1 OO 100 100 100

% Reduction of Salmonella Growth

Concentration F18 X1 F125 F126 F127 F1 28 F129 F 130 F131 F132 F133 F134

O.OO5% 50.3 29.9 33.6 40.4 41.4 34.1 41.4 28.9 29.9 39.3 24.7 47.7 O.01% 733 SO3 63.4 43.5 33.6 34.1 36.7 78.6 41.4 33.1 299 28.9 O.05% 1OO 100 100 97.9 95.8 81.7 O 100 100 90.6 80.1 6.4

0081 Results: 0090 9. At both, 5% and 10% pelargonic acid, cinna I0082) 1. At 5% pelargonic acid, butyraldehyde by itself maldehyde can replace trans-2-hexenal. is not as effective as trans-2-hexenal. 0.091 10. At both, 5% and 10% pelargonic acid, decanal I0083. 2. At 10% pelargonic acid, 20% butyraldehyde can replace trans-2-hexenal. was as effective as 20% trans-2-hexenal. 0092 11. At both, 5% and 10% pelargonic acid, furfural I0084 3. At both, 5% and 10% pelargonic acid, butyral can replace trans-2-hexenal. dehyde can partially replace trans-2-hexenal. 0093. 12. All the formulations tested were as effective I0085 4. At 5% pelargonic acid, citral by itself is not as and in Some instance better than a positive formula with effective as trans-2-hexenal. 25% or 20% trans-2-hexenal or the formic/propionic I0086 5. At 10% pelargonic acid, 20% citral was as formulation. effective as 20% trans-2-hexenal. I0087 6. At both, 5% and 10% pelargonic acid, citral can partially replace trans-2-hexenal. CONCLUSION I0088 7. At both, 5% and 10% pelargonic acid, unde 0094 Pelargonic acid potentiates the efficacy of each indi cylenic aldehyde can replace trans-2-hexenal. vidual aldehyde and aldehyde combination. It will be appar I0089 8. At both, 5% and 10% pelargonic acid, decadi ent to those skilled in the art that variations and modifications enal aldehyde can replace trans-2-hexenal. of the invention can be made without departing from the sprit US 2015/003 1762 A1 Jan. 29, 2015

and scope of the teachings above. It is intended that the 7. A method for extending the shelf-life of water, feed or specification and examples be considered as exemplary only feed ingredients, comprising: and are not restrictive. spray-treating or admixing to water, feed or feed ingredi 1. An antimicrobial composition for extending the shelf ents, an effective amount of a composition comprising: life of water, feed or feed ingredients, comprising: Water, Water, a mixture of C-C organic acids, a mixture of C-Cls organic acids, a mixture of C-C aldehydes, a mixture of C-C aldehydes, 5-25 wt.% pelargonic acid, 5-25 wt.% pelargonic acid, 0-30 wt.% aldehyde. 0-30 wt.% trans-2-hexenal. 2. The composition of claim 1, wherein the mixture of 8. The method of claim 6, wherein the composition is C-C aldehydes contains formaldehyde, trans-2-hexenal, effective against bacteria, viruses, mycoplasmas or fungi furfural, cinnaldehyde, undecylenic, butyraldehyde, 2.4 present in drinking water, feed and feed ingredients. decadienal, decanal, 2-pentenal, 2.4-hexadienal or mixture 9. The method of claim 6, wherein the mixture of C-C, thereof. aldehydes contains formaldehyde. 3. The composition of claim 1, wherein the mixture of 10. The method of claim 6, wherein the mixture of C-Cls C-C aldehydes contains aldehydes other than listed on organic acids contains acetic acid and propionic acid. claim 2. 11. The method of claim 6, comprising 0-20 wt.% form 4. The composition of claim 1, wherein the mixture of aldehyde. C-Cls organic acids contains acetic acid and propionic acid. 12. The method of claim 6, wherein said composition con 5. The composition of claim 1, comprising 0-20 wt.% tains formaldehyde. 5-15 wt.% nonanoic acid, 6. The composition of claim 1, which contains 10-20 wt.% acetic acid, 5-15 wt.% nonanoic acid, 40-50 wt.% propionic acid, 10-20 wt.% acetic acid, 40-50 wt.% propionic acid, 5-30 wt.% trans-2-hexenal, 0-30 wt.% trans-2-hexenal, 5-30 wt.% of other aldehyde 0-30 wt.% of other aldehyde k k k k k