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(12) United States Patent (10) Patent No.: US 8,946,121 B2 Stark Et Al

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(12) United States Patent (10) Patent No.: US 8,946,121 B2 Stark Et Al USOO8946 121B2 (12) United States Patent (10) Patent No.: US 8,946,121 B2 Stark et al. (45) Date of Patent: Feb. 3, 2015 (54) ANTIFUNGAL COMPOSITIONS (52) U.S. Cl. CPC .............. A0IN 43/90 (2013.01); A0IN 43/653 (75) Inventors: Jacobus Stark, Echt (NL); Angelique (2013.01); A23L 3/34 (2013.01) De Rijk, Echt (NL) USPC ............... 504/101: 504/100: 514/31; 514/63; 514/266.23: 514/383: 514/384; 426/335; (73) Assignee: DSM IP Assets B.V., Heerlen (NL) 4267532 (58) Field of Classification Search (*) Notice: Subject to any disclaimer, the term of this USPC ......... 504/100, 101: 514/31, 63. 266.23,383, patent is extended or adjusted under 35 514/384; 426/335, 532 U.S.C. 154(b) by 0 days See application file for complete search history. (56) References Cited (21) Appl. No.: 13/985,452 U.S. PATENT DOCUMENTS (22) PCT Filed: Mar. 1, 2012 6,156,362 A * 12/2000 Cirigliano et al. ............ 426,335 7.816,332 B2 * 10/2010 Starket al. ...................... 51431 (86). PCT No.: PCT/EP2012/053509 2005/0226974 A1* 10/2005 Faragher et al. .............. 426,335 S371 (c)(1), FOREIGN PATENT DOCUMENTS (2), (4) Date: Aug. 14, 2013 EP O101102 A2 2, 1984 (87) PCT Pub. No.: WO2012/117051 EP O748588 A1 12, 1996 EP O986965 A1 3, 2000 PCT Pub. Date: Sep. 7, 2012 EP 2036438 A1 3, 2009 WO 2007OO9969 A2 1, 2007 (65) Prior Publication Data OTHER PUBLICATIONS US 2013/0324.403 A1 Dec. 5, 2013 International Search Report for PCT/EP2012/053509, Mailed May 18, 2012. (30) Foreign Application Priority Data * cited by examiner Mar. 3, 2011 (EP) ..................................... 11156773 Primary Examiner — John Pak (74) Attorney, Agent, or Firm — Miles & Stockbridge, PC (51) Int. Cl. AOIN 43/90 (2006.01) (57) ABSTRACT AOIN 43/653 (2006.01) The present invention relates to new antifungal compositions AOIN 55/10 (2006.01) and their use in the treatment of agricultural products. A23L3/34 (2006.01) 12 Claims, No Drawings US 8,946,121 B2 1. 2 ANTIFUNGAL COMPOSITIONS For many decades, the polyene macrollide antimycotic natamycin has been used to prevent fungal growth on food CROSS REFERENCE TO RELATED products such as cheeses and sausages. For instance, in EP 0 APPLICATIONS 748 588 A1 the use of fungal compositions comprising a polyene antifungal agent and an imidazole antifungal agent This application is a S371 National Stage Application of for the treatment of food and agricultural products is PCT/EP2012/053509, filed Mar. 1, 2012, which claims pri described. This natural preservative, which is produced by ority to European Application No. 11156773.1, filed Mar. 3, fermentation using Streptomyces natalensis, is widely used 2011. throughout the world as a food preservative and has a long 10 history of safe use in the food industry. It is very effective BACKGROUND OF THE INVENTION against all known food spoilage fungi. Although natamycin has been applied for many years in e.g. the cheese industry, up 1. Field of the Invention to now development of resistant fungal species has never been The present invention discloses new antimicrobial compo observed. sitions to control plant diseases and to prevent microbial 15 Consequently, it can be concluded that there is a severe spoilage of crops. need for more effective antimicrobial compositions, e.g. anti 2. Description of Related Art fungal compositions, for the treatment of fungal growth in It is estimated that about 25% of the world crop production and on plants and crops. is lost due to microbial spoilage, of which spoilage by fungi is SUMMARY by far the most important cause. Not only from an economical point of view, but also from a humane point of view it is of The present invention solves the problem by providing a great importance to prevent spoilage of food products. After new synergistic antimicrobial, e.g. antifungal, composition all, in many parts of the world people Suffer from hunger. comprising a polyene antifungal compound and at least one Success in combating plant and crop diseases and in reduc 25 antifungal compound from the family of triazole fungicides. ing the damage they cause to yields and quality depends As used herein, the term “synergistic’ means that the com greatly on the timely application of fungicides. The pro bined effect of the antifungal compounds when used in com longed and frequent use of many fungicides such as e.g. bination is greater than their additive effects when used indi benzamidazoles has contributed to reduce their effectiveness vidually. thanks to the development of phenomena of resistance. 30 An important group of fungicides are the triazoles. The first DETAILED DESCRIPTION OF A PREFERRED triazole that was introduced was triadimefon. This triazole EMBODIMENT was introduced in 1976 by Bayer (see Kuck et al., 1987). Triadimefon provided curative as well as protective activity, In general, Synergistic activity of two active ingredients low application rates and excellent redistribution in the plant. 35 can be tested in for example the analysis of variance model Additional triazole fungicides were introduced over the next using the treatment interaction stratum (see Slinker, 1998). two decades with improved potency and plant safety (e.g., Relative efficacy can be calculated by means of the following epoxiconazole), a broader effective spectrum (e.g., propi formula: (value of evolution status of untreated control conazole, tebuconazole) or specialized applications (e.g., value of evolution status of composition)/(value of evolution difenoconazole and triticonazole for seed treatment) (see 40 status of untreated control))* 100. An interaction coefficient Kucket al., 1987). Next to their use in protecting agricultural can then be calculated by means of the following formula: products such as harvested fruit or vegetables from phyto ((relative efficacy of combination compound A+compound pathogenic fungi (see EP 2 036 438 A1) or cereals from B)/(relative efficacy of compound A+relative efficacy of com mycotoxin contamination (see WO 2007/009969), triazoles pound B))* 100. An interaction coefficient larger than 100 have been used to protect food products from fungal decay 45 indicates Synergy between the compounds. (see EP 0 101 102 A2). Alternatively, synergy can be calculated as follows: the Triazole fungicides however have not been immune to antifungal activity (in 96) of the individual active ingredients challenges in their development and maintenance. They have can be determined by calculating the reduction in mould well-documented side effects on plants. Application to shoots growth observed on products treated with the active ingredi and roots often reduces elongation and causes leaves to be 50 ents in comparison to the mould growth on products treated Smaller, thicker, and greener. Treated plants may be delayed with a control composition. The expected antifungal activity in senescence, which can impede harvest or improve yields, (E in 96) of the combined antifungal composition comprising depending on the crop (see Buchenauer, 1987). both active ingredients can be calculated according to the A larger concern has been resistance development, since Colby equation (Colby, 1967): E=X+Y-I(XY)/100, triazole fungicides have many of the same properties as the 55 wherein X and Y are the observed antifungal activities (in %) benzimidazoles. Resistance to the triazole fungicides devel of the individual active ingredients X and Y, respectively. If oped first in the powdery mildews and has also been observed the observed antifungal activity (O in %) of the combination on other diseases (see Kucket al., 1987; Buchenauer, 1987: exceeds the expected antifungal activity (E in %) of the com Ma et al., 2002). bination and the synergy factor O/E is thus >1.0, the com Moreover, although the launch of triazole fungicides pro 60 bined application of the active ingredients leads to a syner vided potent, systemic fungicide Solutions for Ascomycete gistic antifungal effect. and Basidiomycete diseases, control of devastating In an embodiment of the invention, the at least one anti Oomycete diseases such as potato late blight and grape fungal compound from the family of triazole fungicides is downy mildew is limited and root rots of established plants selected from the group consisting of amisulbrom, azacona (caused by Phytophthora and Pythium) and systemic downy 65 Zole, bitertanol, bromuconazole, cyproconazole, diclobutra mildews cannot be controlled at all by applying triazole fun Zol, difenoconazole, diniconazole, diniconazole-M, epoxi gicides. conazole, etaconazole, fenbuconazole, fluotrimazole, US 8,946,121 B2 4 fluguinconazole, flusilaZole, flutriafol, furconazole, furcona from about 0.0005 g/l to about 1500 g/l of an antifungal Zole-cis, hexaconazole, huanjunZuo, imibenconazole, compound from the family of triazole fungicides. More pref ipconazole, metconazole, myclobutanil, penconazole, propi erably, the amount is from 0.001 g/l to 1000 g/l. conazole, prothioconazole, quinconazole, Simeconazole, In an embodiment the composition of the present invention tebuconazole, tetraconazole, triaZbutil, triticonazole, uni further comprises at least one additional compound selected conazole and uniconazole-P. In a preferred embodiment the at from the group consisting of a sticking agent, a carrier, a least one antifungal compound from the family of triazole colouring agent, a protective colloid, an adhesive, a herbicide, fungicides is selected from the group consisting of bitertanol, a fertilizer, a thickening agent, a sequestering agent, a thixo cyproconazole, difenoconazole, epoxiconazole,
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