Bactericidal composition

Abstract

A fungicidal composition containing a mixture of components (A) and (B) as defined in claim 1, and the use of the composition in agriculture or horticulture for controlling or preventing infection of plants by phytopathogenic microorganisms, preferably fungi.

Description

[Technical Field]

[0001] The present invention relates to novel fungicidal compositions for treating phytopathogenic diseases on useful plants, in particular caused by phytopathogenic fungi, and to a method for controlling such diseases and / or fungi on useful plants. [Background technology]

[0002] Although many fungicidal compounds belonging to various different chemical classes have been or are being developed for use as fungicides in useful plant crops, the crop's resistance and efficacy against certain plant pathogenic fungi often do not meet the demands of agricultural practice. International Publication No. 2018 / 102345 discloses the use of aureobasidin A as an agricultural fungicide for treating, preventing, or controlling fungal infections in plants and seeds. Aureobasidin A is an antifungal cyclic depsipeptide antibacterial agent produced by Aureobasidium pullulans. See, e.g., Takesako et al., The Journal of Antibiotics, 1991, 44, 919-924.

[0003] However, there continues to be a need to find new compositions with superior biological properties for use in controlling or preventing plant infestation by phytopathogenic fungi, such as compositions with a broader spectrum of activity, improved crop resistance, synergistic interactions or enhancing properties, or compositions that exhibit a more rapid onset of action or have longer-lasting residual activity, or that allow for fewer applications and / or reduced rates of compounds and compositions required for effective control of plant pathogens, thereby enabling beneficial resistance management practices, reduced environmental impact, and reduced worker exposure.

[0004] Compositions containing mixtures of different fungicidal compounds with different mechanisms of action can be used to meet some of these needs (e.g., by combining fungicides with different spectra of activity). Summary of the Invention [Means for solving the problem]

[0005] According to the present invention, there is provided a fungicidal composition comprising as active ingredients a mixture of components (A) and (B), wherein component (A) is a compound of formula (I): [ka] (In the formula, R 1 is methyl, ethyl, 1-hydroxyethyl, or 2-hydroxyethyl; A 1 is an α-amino acid residue selected from the group consisting of residues of N-methyl-L-valine (L-MeVal) and L-valine (L-Val); A 2 is an α-amino acid residue selected from the group consisting of L-phenylalanine (L-Phe), ortho-fluoro-L-phenylalanine (Lo-FPhe), meta-fluoro-L-phenylalanine (Lm-FPhe), L-tyrosine (L-Tyr), L-cyclohexylalanine (L-Cha), O-acetyl-L-tyrosine [L-Tyr(Ac)], O-hexanoyl-L-tyrosine [L-Tyr(n-hexanoyl)], O-benzoyl-L-tyrosine [L-Tyr(Bzl)], and persephanine residues; A 3are N-methyl-L-phenylalanine (L-MePhe), L-phenylalanine (L-Phe), β-hydroxy-N-methyl-L-phenylalanine (L-β-OH-MePhe), ortho-fluoro-N-methyl-L-phenylalanine (LoF-MePhe), meta-fluoro-N-methyl-L-phenylalanine (LmF-MePhe), para-fluoro-N-methyl-L-phenylalanine (LpF-MePhe), meta-bromo-N-methyl-L-phenylalanine (Lm-Br-MePhe), para-bromo-N-methyl-L-phenylalanine (LpF-MePhe), Iodo-N-methyl-L-phenylalanine (Lp-Br-MePhe), meta-iodo-N-methyl-L-phenylalanine (LmI-MePhe), para-iodo-N-methyl-L-phenylalanine (LpI-MePhe), 3-phenyl-N-methyl-L-phenylalanine, 4-phenyl-N-methyl-L-phenylalanine, 3-(4-fluorophenyl)-N-methyl-L-phenylalanine, 4-(4-fluorophenyl)-N-methyl-L-phenylalanine, 3-(4-pyridinyl)-N-methyl-L-phenylalanine, 4-( 4-pyridinyl)-N-methyl-L-phenylalanine, 3-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-4-pyridinyl)-N-methyl-L-phenylalanine, 3-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 3-[4-(piperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4-(piperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine [4-(4-methylpiperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, 3-[4-(4-methylpiperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4-(4-methylpiperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, β-oxo-N-methyl-L-phenylalanine (L-β-oxo-MePhe), β-acetoxy-N-methyl-L-phenylalanine (L-β-AcO-MePhe), N-methyl-L-tyrosine (L-MeTyr),an α-amino acid residue selected from the group consisting of residues of O-methyl-N-methyl-L-tyrosine [L-MeTyr(Me)], N-methyl-L-alanine (L-MeAla), N-methyl-L-serine (L-MeSer), N-methyl-D-phenylalanine (D-MePhe), N-methyl-D-alanine (D-MeAla), N-methyl-D-valine (D-MeVal), N-methyl-D-serine (D-MeSer), N-methyl-sarcosine (MeSar), and N-methyl-L-serine (L-MeSer); A 4 is an α-amino acid residue selected from the group consisting of residues of L-proline (L-Pro), L-thioproline (L-SPro), and 4-hydroxy-L-proline (L-4Hyp); A 5 is an α-amino acid residue selected from the group consisting of L-allo-isoleucine (L-AIle), L-leucine (L-Leu), L-norleucine (L-Nle), L-norvaline (L-Nva), and L-valine (L-Val); A 6 is an α-amino acid residue selected from the group consisting of residues of N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAIle), and L-valine (L-Val); A 7 is an α-amino acid residue selected from the group consisting of residues of L-leucine (L-Leu), L-allo-isoleucine (L-AIle) and L-norvaline (L-Nva); A 8 β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), γ-hydroxy-N-methyl-L-valine (L-γ-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDH), 2,3 Val), N-methyl-3,4-didehydro-L-valine (L-MeDH 3,4and N,β-dimethyl-L-aspartic acid (LN,β-MeAsp) residues. or a stereoisomeric cyclic depsipeptide thereof; The component (B) is a respiratory inhibitor: (B.1) Azoxystrobin, cumoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, enestroblin, phenaminestrobin, phenoxystrobin / Flufenoxystrobin, Fluoxastrobin, kresoxim methyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate methyl ester, 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methyl-acetamide, (2E,3Z)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (2E,3Z)-5-[1-(4-chlorophenyl) )pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, pyribencarb, triclopiricarb / chlorozinecarb, famoxadone, fenamidone, 1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, methyltetraprole, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one, 1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one, 1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]-methyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazo Q selected from the group consisting of tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, pyriminostrobin, and bifujunzhi, o with inhibitors of complex III at the site; (B.2) Cyazofamid, amisulbrom, [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate, fenpicoxamide, [(6S,7R,8R)-8-benzyl-3-[[4-methoxy-3-(propanoyloxymethoxy)pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate, Q selected from the group consisting of [5-dioxonan-7-yl]-2-methylpropanoate, furoylpicoxamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl], and (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-1-methyl-2-(o-tolyl)propyl]. i with inhibitors of complex III at the site; (B.3) Benzovindiflupyr, bixafen, fluindapyr, boscalid, carboxin, pyraziflumid, fenfuram, cyclobutrifluram, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide, sedaxane, pyrapropoin, isoflucipram, teklof Thalam, Thifluzamide, 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-tri Methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamidean inhibitor of complex II selected from the group consisting of 1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide; (B.4) Other respiratory inhibitors selected from the group consisting of diflumetrim; tolfenpyrad; fenazaquin; nitrophenyl derivatives: binapacryl, dinobuton, dinocap, fluazinam, meptyldinocap, ferimzone; organometallic compounds: fentin salts, such as fentin acetate, fentin chloride, or fentin hydroxide; ametoctrazine; and silthiofam, A disinfectant composition is provided, selected from the group consisting of:

[0006] Typically, the weight ratio of component (A) to component (B) can be from 100:1 to 1:1000, preferably from 100:1 to 1:500, more preferably from 50:1 to 1:200, and even more preferably from 20:1 to 1:40.

[0007] In some preferred embodiments of the present invention, the weight ratio of component (A) to component (B) may be 1:1, or 1:2, or 2:1, or 4:1, or 8:1, or 16:1, or 1:200, or 1:100, or 1:50, or 1:25, or 1:20, or 1:12.5, or 1:10, or 1:6.2, or 1:5, or 1:2.5.

[0008] According to a second aspect of the present invention, there is provided a method for controlling or preventing phytopathogenic diseases, in particular caused by phytopathogenic fungi, in useful plants or their propagation material, which method comprises applying a composition as defined in the present invention to a useful plant, its habitat or its propagation material. Preferred is a method comprising applying a composition according to the present invention to a useful plant or its habitat, more preferably to a useful plant. Even more preferred is a method comprising applying a composition according to the present invention to propagation material of a useful plant.

[0009] According to a third aspect of the present invention, there is provided the use of a composition comprising component (A) and component (B) as defined in the present invention as a disinfectant.

[0010] It has been discovered that the use of a compound of formula (I) in combination with a compound of component (B) and, optionally, a compound of component (C) can unexpectedly and substantially enhance the effectiveness of the compound of formula (I) against fungi, and vice versa. Also, the use of the compositions of the present invention can be effective against a broader range of such fungi than can be controlled by the individual active ingredients when used alone.

[0011] The benefits conferred by particular fungicidal compositions according to the invention may include, in particular, advantageous levels of biological activity for protecting plants from diseases caused by fungi, or superior properties for use as an active pesticide ingredient (e.g., high biological activity, advantageous activity spectrum, increased safety profile, improved physicochemical properties, or increased biodegradability).

[0012] As used herein, the term "cyclic depsipeptide" refers to a peptide consisting of consecutive units derived from 2-hydroxy-3-methylalkanoic acid and α-amino acid A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8 and a cyclic peptide consisting of units derived from α-amino acid residues A 8 is the ester group of 2-hydroxy-3-methylalkanoic acid -OCH(CH(CH3)R 1 ) moiety to form -C(=O)OCH(CH(CH3)R 1 ) moiety, and α-amino acid residue A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8are bonded to each other via a peptide bond. The 2-hydroxy-3-methylalkanoic acid can be 2(R)-hydroxy-3(R)-methylpentanoic acid or 2(R)-hydroxy-3-methylbutanoic acid. DETAILED DESCRIPTION OF THE INVENTION

[0013] In a first embodiment of the invention, component (A) is one or more cyclic depsipeptides of formula (IA): [ka] (In the formula, R 1 is methyl or ethyl; X 1 , X 2 and X 3 Each of X is hydrogen, or 1 , X 2 and X 3 is hydrogen, fluorine or hydroxyl, provided that X 1 , X 2 and X 3 is fluorine or hydroxyl; X 4 is CH, S or hydroxymethylene; A 3are N-methyl-L-phenylalanine (L-MePhe), L-phenylalanine (L-Phe), β-hydroxy-N-methyl-L-phenylalanine (L-β-OH-MePhe), ortho-fluoro-N-methyl-L-phenylalanine (LoF-MePhe), meta-fluoro-N-methyl-L-phenylalanine (LmF-MePhe), para-fluoro-N-methyl-L-phenylalanine (LpF-MePhe), meta-bromo-N-methyl-L-phenylalanine (Lm-Br-MePhe), para-bromo-N-methyl-L-phenylalanine (LpF-MePhe), Iodo-N-methyl-L-phenylalanine (Lp-Br-MePhe), meta-iodo-N-methyl-L-phenylalanine (LmI-MePhe), para-iodo-N-methyl-L-phenylalanine (LpI-MePhe), 3-phenyl-N-methyl-L-phenylalanine, 4-phenyl-N-methyl-L-phenylalanine, 3-(4-fluorophenyl)-N-methyl-L-phenylalanine, 4-(4-fluorophenyl)-N-methyl-L-phenylalanine, 3-(4-pyridinyl)-N-methyl-L-phenylalanine, 4-( 4-pyridinyl)-N-methyl-L-phenylalanine, 3-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-4-pyridinyl)-N-methyl-L-phenylalanine, 3-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 3-[4-(piperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4-(piperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine [4-(4-methylpiperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, 3-[4-(4-methylpiperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4-(4-methylpiperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, β-oxo-N-methyl-L-phenylalanine (L-β-oxo-MePhe), β-acetoxy-N-methyl-L-phenylalanine (L-β-AcO-MePhe), N-methyl-L-tyrosine (L-MeTyr),an α-amino acid residue selected from the group consisting of O-methyl-N-methyl-L-tyrosine [L-MeTyr(Me)], N-methyl-L-alanine (L-MeAla), N-methyl-L-serine (L-MeSer), N-methyl-D-phenylalanine (D-MePhe), N-methyl-D-alanine (D-MeAla), N-methyl-D-valine (D-MeVal), N-methyl-D-serine (D-MeSer) and N-methyl-L-serine (L-MeSer) residues; A 5 is an α-amino acid residue selected from the group consisting of L-allo-isoleucine (L-AIle), L-leucine (L-Leu), L-norleucine (L-Nle), L-norvaline (L-Nva) and L-valine (L-Val) residues; A 6 is an α-amino acid residue selected from the group consisting of N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAIle) and L-valine (L-Val) residues; A 7 is an α-amino acid residue selected from the group consisting of L-leucine (L-Leu), L-allo-isoleucine (L-AIle), and L-norvaline (L-Nva) residues; and A 8 β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), γ-hydroxy-N-methyl-L-valine (L-γ-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDH), 2,3 Val), N-methyl-3,4-didehydro-L-valine (L-MeDH 3,4 and N,β-dimethyl-L-aspartic acid (LN,β-MeAsp) residues). Includes.

[0014] Preferably, the compounds of formula (I) according to the present invention are selected from compounds 1.001 to 1.035 listed in Table A (below) or compounds 2.001 to 2.045 listed in Table B (below).

[0015] The following list provides the substituents R for the compounds of formula (I) of the present invention: 1 , A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8 For any one of these substituents, any of the definitions set forth below may be combined with any of the definitions of any other substituents set forth below or elsewhere in this specification.

[0016] Table A: This table discloses 35 compounds of formula (I), wherein R 1 , A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8 are as set forth in Table A below.

[0017] [Table 1-1] [Table 1-2]

[0018] Table B: This table shows the compounds of formula (I) where R 1 is ethyl, and A 1 is L-MeVal, and A 4 is L-Pro, and A 6 is L-MeVal, and A 7 is L-Leu, and A 2 , A3 , A 5 , and A 8 The present invention discloses 45 compounds of the formula (as set forth in Table B below).

[0019] [Table 2-1] [Table 2-2]

[0020] In a first variant of this first embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-A1), hereinafter referred to as aureobasidin A: [ka] or a stereoisomer thereof.

[0021] As used herein, the term "aureobasidin A" refers to a cyclic depsipeptide of formula (I-A1) or a stereoisomer thereof, consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-phenylalanine (L-Phe), N-methyl-L-phenylalanine (L-MePhe), L-proline (L-Pro), L-allo-isoleucine (L-AIle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu), and β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal).

[0022] In a second variant of this first embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-A2), hereinafter referred to as aureobasidin E: [ka] or a stereoisomer thereof.

[0023] As used herein, the term "aureobasidin E" refers to a cyclic depsipeptide of formula (I-A2) consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-phenylalanine (L-Phe), β-hydroxy-N-methyl-L-phenylalanine (L-β-OH-MePhe), L-proline (L-Pro), L-allo-isoleucine (L-AIle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu), and β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), or a stereoisomer thereof.

[0024] In a third variant of this first embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-A3), hereinafter referred to as aureobasidin G: [ka] or a stereoisomer thereof.

[0025] As used herein, the term "aureobasidin G" refers to a cyclic depsipeptide of formula (I-A3) consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-phenylalanine (L-Phe), N-methyl-L-phenylalanine (L-MePhe), L-proline (L-Pro), L-allo-isoleucine (L-AIle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu), and N-methyl-L-valine (L-MeVal), or a stereoisomer thereof.

[0026] In one embodiment of the present invention, component (A) comprises two or more cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0027] In a first variant of this embodiment of the invention, component (A) comprises aureobasidin A and one or more other cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0028] In a second variant of this embodiment of the invention, component (A) comprises aureobasidin E and one or more other cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0029] In a preferred embodiment of the present invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.004 and 1.006 to 1.035 set forth in Table A. Preferably, component (A) comprises aureobasidin A and at least one other cyclic depsipeptide of formula (IA) or stereoisomer thereof selected from the group consisting of aureobasidin E and aureobasidin G.

[0030] In another preferred embodiment of the present invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 2.001 to 2.045 listed in Table B.

[0031] In embodiments where component (A) comprises aureobasidin A and one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof, said component (A) is typically 10% to 99.9% by weight, preferably 20% to 99.9% by weight, more preferably 40% to 99.9% by weight of aureobasidin A; 0.1% to 90% by weight, preferably 0.1% to 80% by weight, more preferably 0.1% to 60% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof Includes.

[0032] In embodiments where component (A) comprises aureobasidin E and one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof, said component (A) is typically 10% to 99.9% by weight, preferably 20% to 99.9% by weight, more preferably 40% to 99.9% by weight of aureobasidin E; 0.1% to 90% by weight, preferably 0.1% to 80% by weight, more preferably 0.1% to 60% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof Includes.

[0033] In one embodiment of the present invention, component (A) is typically: 60% to 99.5% by weight of aureobasidin A; 0.05% to 5% by weight of aureobasidin E; Optionally, 0.1% to 30% by weight of aureobasidin G; Optionally, 0.1% to 10% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof. Includes.

[0034] In a second embodiment of the invention, component (A) is one or more cyclic depsipeptides of formula (IB): [ka] (In the formula, R 1 is methyl or ethyl; X 4 is CH, S or hydroxymethylene; A 5 is an α-amino acid residue selected from the group consisting of L-allo-isoleucine (L-AIle), L-leucine (L-Leu), L-norleucine (L-Nle) and L-valine (L-Val) residues; A 6is an α-amino acid residue selected from the group consisting of N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), L-allo-isoleucine (L-AIle) and N-methyl-L-allo-isoleucine (L-MeAIle) residues; A 7 is an α-amino acid residue selected from the group consisting of L-leucine (L-Leu), L-allo-isoleucine (L-AIle), and L-norvaline (L-Nva) residues; and A 8 are β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), γ-hydroxy-N-methyl-L-valine (L-γ-OH-MeVal), N-methyl-L-valine (L-MeVal), and N-methyl-2,3-didehydro-L-valine (L-MeDH). 2,3 Val), N-methyl-3,4-didehydro-L-valine (L-MeDH 3,4 and N,β-dimethyl-L-aspartic acid (LN,β-MeAsp) residues). or its stereoisomers.

[0035] As used herein, the term "persephanine residue" refers to a group having the formula: [ka] represents the α-amino acid residue of

[0036] In a first variant of this second embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-B1), hereinafter referred to as Persephacin A: [ka] or a stereoisomer thereof.

[0037] As used herein, the term "Persephacin A" refers to a cyclic depsipeptide of formula (I-B1) consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-persephanine, sarcosine (Sar), L-proline (L-Pro), L-allo-isoleucine (L-AIle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu), and β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), or a stereoisomer thereof.

[0038] In a second variant of this second embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-B2), hereinafter referred to as Persephacin B: [ka] or a stereoisomer thereof.

[0039] As used herein, the term "Persephacin B" refers to a cyclic depsipeptide of formula (I-B2) consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-persephanine, sarcosine (Sar), L-proline (L-Pro), L-allo-isoleucine (L-AIle), L-allo-isoleucine (L-AIle), L-leucine (L-Leu), and β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), or a stereoisomer thereof.

[0040] In a third variant of this second embodiment of the invention, component (A) is a cyclic depsipeptide of formula (I-B3), hereinafter referred to as Persephacin C: [ka] or a stereoisomer thereof.

[0041] As used herein, the term "Persephacin C" refers to a cyclic depsipeptide of formula (I-B3) consisting of consecutive units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl-L-valine (L-MeVal), L-persephanine, sarcosine (Sar), L-proline (L-Pro), L-allo-isoleucine (L-AIle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu), and N-methyl-L-valine (L-MeVal), or a stereoisomer thereof.

[0042] In one embodiment according to the invention, component (A) comprises two or more cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof.

[0043] In a variation of this embodiment of the invention, component (A) comprises Persephacin A and one or more other cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof.

[0044] In embodiments where component (A) comprises Persephacin A and one or more other cyclic depsipeptides of formula (IB) or stereoisomers thereof, said component (A) is typically: 10% to 99.9% by weight, preferably 20% to 99.9% by weight, more preferably 40% to 99.9% by weight of Persephacin A; 0.1% to 90% by weight, preferably 0.1% to 80% by weight, more preferably 0.1% to 60% by weight of one or more other cyclic depsipeptides of formula (IB) or stereoisomers thereof Includes.

[0045] In another embodiment of the present invention, component (A) comprises one or more cyclic depsipeptides of formula (IA) or stereoisomers thereof and one or more cyclic depsipeptides of formula (IB) or stereoisomers thereof as defined above.

[0046] In a variant of this embodiment of the invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof.

[0047] In another variation of this embodiment of the invention, component (A) comprises aureobasidin A, one or more other cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof, and one or more cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof.

[0048] In another variation of this embodiment of the invention, component (A) comprises at least one other cyclic depsipeptide of formula (IA) or a stereoisomer thereof selected from the group consisting of aureobasidin A, aureobasidin E and aureobasidin G, and one or more cyclic depsipeptides of formula (IB) or a stereoisomer thereof as defined above.

[0049] In another embodiment of the present invention, component (A) is a strain of Aureobasidium pullulans, generally the strain Aureobasidium pullulans R106.

[0050] Without limiting the scope of the present invention, it is understood that one or more cyclic depsipeptides of formula (IA) or stereoisomers thereof as defined above are obtainable from the fermentation broth of a strain of Aureobasidium pullulans, generally the strain Aureobasidium pullulans R106.

[0051] In another embodiment of the present invention, component (A) is a strain or a genetically engineered strain of Sphaceloma coryli.

[0052] Without limiting the scope of the present invention, it is understood that one or more cyclic depsipeptides of formula (IB) or stereoisomers thereof as defined above can be obtained from the fermentation broth of a strain or genetically engineered strain of Sphaceloma coryli.

[0053] As used herein, the term "fermentation broth" refers to the composition obtained from the fermentation process of a bacterial strain.

[0054] In another embodiment of the present invention, component (A) is a fermentation broth comprising two or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.

[0055] In a first variant of this embodiment of the invention, component (A) is a fermentation broth comprising two or more cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0056] In one embodiment of the present invention, component (A) is a fermentation broth comprising aureobasidin A and one or more other cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0057] In another embodiment of the present invention, component (A) is a fermentation broth comprising aureobasidin E and one or more other cyclic depsipeptides of formula (IA) as defined above or stereoisomers thereof.

[0058] In a second variant of this embodiment of the invention, component (A) is a fermentation broth comprising two or more cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof, preferably component (A) is a fermentation broth comprising Persephacin A and one or more other cyclic depsipeptides of formula (IB) as defined above or stereoisomers thereof.

[0059] The component (B) compounds are referred to herein and herein above by the so-called "ISO trivial names" or other "trivial names" used in individual cases or trade names. The component (B) compounds are known and commercially available and / or can be prepared using techniques known in the art and / or reported in the literature.

[0060] In one preferred embodiment according to the present invention, component (B) is a respiratory inhibitor: (B.1) Azoxystrobin, cumoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, enestroblin, phenaminestrobin, phenoxystrobin / Flufenoxystrobin, Fluoxastrobin , kresoximmethyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopiricarb / chlorozinecarb, famoxadone, fenamidone, methyltetraprole, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, and (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, and pyriminostrobin. o with inhibitors of complex III at the site; (B.2) Q selected from the group consisting of cyazofamid, amisulbrom, fenpicoxamid, florylpicoxamid, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl], and (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-1-methyl-2-(o-tolyl)propyl]. i with inhibitors of complex III at the site; (B.3) an inhibitor of Complex II selected from the group consisting of benzovindiflupyr, bixafen, fluindapyr, boscalid, carboxin, pyraziflumide, fenfuram, cyclobutrifluram, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, sedaxane, pyrapropoin, isoflucipram, tecloftalam, thifluzamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide; (B.4) other respiratory inhibitors selected from the group consisting of binapacryl, dinobuton, dinocap, fluazinam, and meptyldinocap; is selected from the group consisting of:

[0061] In a more preferred embodiment according to the present invention, component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide.

[0062] In an even more preferred embodiment according to the present invention, component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, florylpicoxamide, fluopyram, pydiflumetofen, fluazinam, benzovindiflupyr, isoflucipram, and metyltetrapole.

[0063] In a preferred composition according to the invention, component (A) comprises one or more cyclic depsipeptides of formula (IA) as defined above or its stereoisomers, and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, flurylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, The compound is selected from the group consisting of dimethyl-penta-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40.

[0064] In another preferred composition according to the invention, component (A) is aureobasidin A, and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, flurylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy- The compound is selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:1000.

[0065] In another preferred composition according to the present invention, component (A) is aureobasidin A and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy- The compound is selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:500.

[0066] In another preferred composition according to the invention, component (A) is aureobasidin A, and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy the compound selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 50:1 to 1:200.

[0067] In another preferred composition according to the invention, component (A) is aureobasidin A, and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy The compound is selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 20:1 to 1:40.

[0068] In another preferred composition according to the present invention, component (A) is aureobasidin E and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, and the like. -methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:1000.

[0069] In another preferred composition according to the present invention, component (A) is aureobasidin E and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy- The compound is selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:500.

[0070] In another preferred composition according to the present invention, component (A) is aureobasidin E and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy- The compound is selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 50:1 to 1:200.

[0071] In another preferred composition according to the present invention, component (A) is aureobasidin E and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy a compound selected from the group consisting of 2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 20:1 to 1:40.

[0072] In another preferred composition according to the present invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.004 and 1.006 to 1.035 as set forth in Table A, preferably component (A) comprises aureobasidin A and at least one other cyclic depsipeptide of formula (IA) or stereoisomers thereof selected from the group consisting of aureobasidin E and aureobasidin G. and depsipeptide of the formula, and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)-2-propanol] )pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino ]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:1000.

[0073] In another preferred composition according to the invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.004 and 1.006 to 1.035 as set forth in Table A, preferably component (A) comprises aureobasidin A and at least one other cyclic depsipeptide of formula (IA) or stereoisomers thereof selected from the group consisting of aureobasidin E and aureobasidin G. and a cyclic depsipeptide, and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenoxy)-2-methyl-2-propanol, and the like. (1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amido] ... [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:500.

[0074] In another preferred composition according to the invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.004 and 1.006 to 1.035 as set forth in Table A, preferably component (A) comprises aureobasidin A and at least one other cyclic depsipeptide of formula (IA) or stereoisomers thereof selected from the group consisting of aureobasidin E and aureobasidin G. and a cyclic depsipeptide, and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenoxy)-2-methyl-2-propanol, and the like. (1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)azoline, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide ... [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)azoline [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 50:1 to 1:200.

[0075] In another preferred composition according to the invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.004 and 1.006 to 1.035 as set forth in Table A, preferably component (A) comprises aureobasidin A and at least one other cyclic depsipeptide of formula (IA) or stereoisomers thereof selected from the group consisting of aureobasidin E and aureobasidin G. and a cyclic depsipeptide, and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenoxyethanol)-2-yl]-2H-pyrazolinone, and benzophenone. (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl) [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 20:1 to 1:40.

[0076] In another preferred composition according to the invention, component (A) is an Aureobasidium pullulans strain, generally Aureobasidium pullulans strain R106, and component (B) is a respiratory inhibitor: (B.1) Azoxystrobin, cumoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, enestroblin, phenaminestrobin, phenoxystrobin / Flufenoxystrobin, Fluoxastrobin , kresoximmethyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb / chlorozinecarb, famoxadone, fenamidone, methyltetraprole, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide and (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, and pyriminostrobin. o with inhibitors of complex III at the site; (B.2) Q selected from the group consisting of cyazofamid, amisulbrom, fenpicoxamid, florylpicoxamid, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl], and (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-1-methyl-2-(o-tolyl)propyl]. i with inhibitors of complex III at the site; (B.3) an inhibitor of Complex II selected from the group consisting of benzovindiflupyr, bixafen, fluindapyr, boscalid, carboxin, pyraziflumide, fenfuram, cyclobutrifluram, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, sedaxane, pyrapropoin, isoflucipram, tecloftalam, thifluzamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide; (B.4) other respiratory inhibitors selected from the group consisting of binapacryl, dinobuton, dinocap, fluazinam, and meptyldinocap; is a compound selected from the group consisting of The weight ratio of component (A) to component (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40.

[0077] In another preferred composition according to the invention, component (A) is an Aureobasidium pullulans strain, generally Aureobasidium pullulans. pullulans R106 strain, and component (B) is azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, florylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2 and a compound selected from the group consisting of N-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, wherein the weight ratio of component (A) to component (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40.

[0078] In another preferred composition according to the invention, component (A) is a fermentation broth containing one or more cyclic depsipeptides of formula (IA) or its stereoisomers as defined above, and component (B) is a respiratory inhibitor: (B.1) Azoxystrobin, cumoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, enestroblin, phenaminestrobin, phenoxystrobin / Flufenoxystrobin, Fluoxastrobin, kresoximmethyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb / chlorozinecarb, famoxadone, fenamidone, methyltetraprole, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide and (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, and pyriminostrobin. o with inhibitors of complex III at the site; (B.2) Q selected from the group consisting of cyazofamid, amisulbrom, fenpicoxamid, florylpicoxamid, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl], and (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-1-methyl-2-(o-tolyl)propyl]. i with inhibitors of complex III at the site; (B.3) an inhibitor of Complex II selected from the group consisting of benzovindiflupyr, bixafen, fluindapyr, boscalid, carboxin, pyraziflumide, fenfuram, cyclobutrifluram, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, sedaxane, pyrapropoin, isoflucipram, tecloftalam, thifluzamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide; (B.4) other respiratory inhibitors selected from the group consisting of binapacryl, dinobuton, dinocap, fluazinam, and meptyldinocap; is a compound selected from the group consisting of The weight ratio of component (A) to component (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40.

[0079] In another preferred composition according to the invention, component (A) is a fermentation broth comprising aureobasidin A and one or more other cyclic depsipeptides of formula (IA) as defined above or one or more stereoisomers thereof, and component (B) is selected from the group consisting of azoxystrobin, trifloxystrobin, pyraclostrobin, methyltetraprole, fluopyram, pydiflumetofen, isofetamide, fluxapyroxad, penthiopyrad, boscalid, cyclobutrifluram, fluazinam, flurylpicoxamide, fenpicoxamide, isoflucipram, benzovindiflupyr, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, Methoxyimino-N,3-dimethyl-pent-3-enamide, [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl )amino]propanoate, and 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, and the weight ratio of component (A) to component (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40.

[0080] The compositions of the present invention may, in certain circumstances, comprise an additional active ingredient, component (C), different from component (B), wherein component (C) is selected from the group consisting of respiratory inhibitors (B.1), (B.1.1), (B.1.2), (B.1.3), (B.2), (B.3) and (B.4) as defined herein.

[0081] In embodiments of the present invention in which the composition comprises component (A), component (B), and component (C), the weight ratio of component (A) to the sum of component (B) and component (C) can be from 100:1 to 1:1000, more preferably from 100:1 to 1:500, even more preferably from 50:1 to 1:200, and even more preferably from 20:1 to 1:40.

[0082] In some preferred embodiments of the present invention, the weight ratio of component (A) to the sum of component (B) and component (C) may be 1:1, or 1:2, or 2:1, or 4:1, or 8:1, or 16:1, or 1:200, or 1:100, or 1:50, or 1:25, or 1:20, or 1:12.5, or 1:10, or 1:6.2, or 1:5, or 1:2.5.

[0083] The compound of formula (I) according to the present invention or its stereoisomers can be prepared by methods known to those skilled in the art. The compound of formula (I) can be commercially available or can be prepared using synthetic or semi-synthetic chemistry or fermentation processes. For example, the compound of formula (IA) or its stereoisomers can be prepared by known methods in Takesako et al., The Journal of Antibiotics, 1991, 44, 919-924; Takesako et al., Tetrahedron, 1996, 52, 4327-4346; and Maharani et al., Tetrahedron, 2014, 70, 2351-2358. A fermentation broth containing one or more compounds of formula (IA) or their stereoisomers can be obtained from the fermentation process of a strain of Aureobasidium pullulans, typically Aureobasidium pullulans R106. A fermentation broth containing one or more compounds of formula (IB) or their stereoisomers can be obtained from the fermentation process of a strain of Sphaceloma coryli. The fermentation broth may not require purification. Alternatively, one or more compounds of formula (I) can be isolated and purified from the fermentation broth by, for example, chromatography using adsorbents (e.g., silica and reverse-phase silica gel, optically active adsorbents, resins) or one or more solvents (e.g., partitioning, countercurrent separation, multiphase solvent mixtures) or other chemical means (e.g., crystallization, recrystallization, salt formation, and precipitation) to achieve final purity. The purity of the compound of formula (I) or its stereoisomers may include, but is not limited to, 10% to 20%, 20% to 30%, 30% to 40%, 40% to 50%, 50% to 60%, 60% to 70%, 70% to 80%, 80% to 90%, or 90% to 100%. The purity of the compound of formula (I) or its stereoisomers may be measured by any technique known to those skilled in the art, including NMR, mass spectrometry, liquid chromatography-mass spectrometry (LCMS), high performance liquid chromatography (HPLC), and other analytical means.

[0084] The term "fungicide" as used herein means a compound that controls, modifies, or prevents fungal growth. The term "fungicidally effective amount" means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. A controlling or modifier effect includes any deviation from natural development, such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent infection by the fungus.

[0085] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage, and fruits.

[0086] The term "plant propagation material" means all reproductive parts of a plant, such as seeds or growing parts of a plant, such as cuttings or tubers. This includes not only seeds in the strict sense, but also roots, fruits, tubers, bulbs, rhizomes, and plant parts.

[0087] As used herein, the term "habitat" means the field in which the plants are growing or in which the seeds of the cultivated plants are sown or in which the seeds will be sown in soil, including the soil, seeds and seedlings, and established vegetation.

[0088] Throughout this specification, the expression "composition" refers to various mixtures or combinations of components (A) and (B) (including the embodiments defined above), such as single "ready-mixed" forms, multiple spray mixtures such as "tank mixes" composed of individual blends of single active ingredient components, and combinations of single active ingredients when applied sequentially (i.e., one after the other within a reasonably short time, such as hours or days). The order in which components (A) and (B) are applied is not critical to the operation of the present invention.

[0089] The compositions of the present invention are effective against harmful microorganisms, such as those causing plant pathogenic diseases, and in particular against plant pathogenic fungi and bacteria.

[0090] The compositions of the present invention may be used to control plant diseases caused by a wide range of fungal plant pathogens in the Basidiomycota, Ascomycota, Oomycota and / or Fungi Imperfecti, Blasocladiomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete classes: Oomycete, including: Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; Pythium aphanidermatum; Pythium diseases such as those caused by P. aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum; Peronospora destructor, Peronospora parasitica, Peronospora manshurica, Peronospora tabacina, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora diseases caused by Peronosporales such as C. cubensis, C. albugo, C. albugo, C. sclerophthora, and C. lactucae;and others such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi and Sclerospora graminicola; Ascomycetes, such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solaniPleosporales, such as Septoria solani and Alternaria tomatophila; Capnodiales, such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora beticola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides; Cladosporium carpophyllum carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Gaeumannomyces graminisMagnaporthales such as Magnaporthe grisea, Magnaporthe oryzae, Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-Juglandacearum, and others. Diaporthales, such as C. clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., and Valsa ceratosperma; as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., and Capnodium ramosum. ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp.spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghini blotch, leaf spot, blast or blight and / or rot diseases such as those caused by others such as Gloeotinia sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monilinia laxa, Monilinia fructigena, Monographella albescens, Monosporascus canonvaluscannonballus, Naemacyclus spp., Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phialophora tetraspora, Phyllachora pomigena, Phymatotrichum omnivora omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, Sclerotium spp, Typhula ishikariensis, Seimatosporium mariae, Lepteutypacupressi), Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Chi Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; e.g. Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, apple powdery mildew (Podosphaera leucotricha), Podospaera macularis, Podosphaera pannosa, Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa Powdery mildew diseases such as those caused by Erysiphales, such as Oidiopsis diffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis;For example, Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botrytis tracheiphila, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta fungi, such as those caused by the Botryosphaeriales, for example Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola; anthracnose, for example, those caused by the Glommerelales, for example Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola;Also, for example, Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium brasiliense, Fusarium tucumaniae, Fusarium cuneirostrum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp. cubense, Gerlachia Wilt or blight diseases such as those caused by Hypocreales such as Gibberella nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum and Verticillium theobromae; Basidiomycete, including smut fungi such as those caused by species of the Ustilaginales, e.g., Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae, e.g., Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.Hordei, Puccinia striiformis f.sp.the Pucciniales, such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phakopsora meibomiae, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces visciae-fabieae; Rust fungi, such as those caused by Uredinales such as Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp.), Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia haperplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae, and Tilletia Other decays and diseases such as those caused by caries; Blastocladiomycetes, such as Physoderma maydis; and Diseases caused by Choanephora cucurbitarum; Mucor spp.; Mucoromycetes such as Rhizopus arrhizus, Rhizopus oryzae, Rhizopus stolonifera, Rhizopus nigricans, and other species and genera closely related to those listed above.

[0091] In addition to its fungicidal activity, the composition may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Streptomyces scabies and other related species, as well as certain protozoa.

[0092] The compositions of the present invention are suitable for use in fungi from the Ascomycetes class (e.g., Venturia, Alternaria, Podosphaera, Erysiphe, Magnaporthe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g., Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (e.g., Fungi genus ... imperfecti (also known as Deuteromycetes; e.g., Botrytis, Colletotrichum, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Penicillium, Pyricularia, and and Pseudocercosporella; and Oomycetes (e.g., Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

[0093] Preferably, the composition according to the invention is effective against Alternaria, Ascochyta, Botrytis, Cercospora, Cochliobolus sativus, Colletotrichum, Colletotrichum lagenarium, Corynespora, Erysiphe, Erysiphe cichoracearum, Sphaerotheca fuliginea, Fusarium, Fusarium oxysporum, Gaeumannomyces graminis, graminis, Guignardia, Helminthosporium, Hemileia vastatrix, Magnaporthe, Magnaporthe oryzae, Monilinia, Mycosphaerella, Mycosphaerella arachidis, Phakopsora, Phoma, Phomopsis, Puccinia, Pseudocercosporella, Pseudopezicula, Phragmidium mucronatum mucronatum, Podosphaera, Pyrenophora, Pyrenophora teres, Pyricularia, Pyricularia oryzae, Ramularia, Ramularia collo-cygni, Rhizoctonia, Rhizoctoniasolani, Rhynchosporium secalis, Sclerotinia, Septoria, Septoria tritici, Sphacelotheca reilliana, Tilletia, Urocystis occulta, Uncinula, Ustilago, Venturia, Monilia, and Penicillium.

[0094] The compositions of the present invention may be particularly effective against plant pathogenic fungi selected from the group consisting of Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula, and Venturia.

[0095] The composition of the present invention is effective against Alternaria solani, Alternaria alternata, Alternaria porri, Botrytis cinerea, Botrytis allii, Botrytis squamosa, Cercospora capsici, Colletotrichum lagenarium, Corynespora cassiicola, Guignardia bidwellii, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Penicillium The fungal inhibitor may be particularly effective against plant pathogenic fungi selected from the group consisting of Penicillium digitatum, Penicillium italicum, Penicillium expansum, Phomopsis viticola, Podosphaera leucotricha, Podosphaera xanthii, Pseudopezicula tracheiphila, Septoria tritici, Uncinula necator, and Venturia inaequalis.

[0096] According to the present invention, "useful plants" typically include the following perennial or annual plants: Cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale, tritordeum and cereal grains such as wheat, amaranth, buckwheat, chia, quinoa and canoe; fruits and tree nuts such as grapes (table and wine grapes), almonds, apples, apricots, avocados, bananas, blackberries, blueberries, breadfruit, cacao, cashews, cherimoyas, cherries, chestnuts, amaryllis, citrus fruits (including grapefruit, limes, lemons, oranges, and calamansi), coconuts, coffee, cranberries, currants, dates, feijoas, figs, hazelnuts, gooseberries, guavas, kiwis, lychees, macadamias, mangoes, nectarines, olives, papayas, passion fruit, peaches, pears, pecans, persimmons, pineapples, pistachios, plums (including prunes), pomegranates, quince, raspberries, strawberries, Surinamese cherries, and walnuts; Artichoke, asparagus, beans (snap beans, green beans, dry beans, edible beans), beets (top), broccoli / Italian turnip, Brussels sprouts, cabbage (including Chinese cabbage), carrots, cauliflower, celeriac, celery, chickpeas, chives, chili cabbage (including kale), cucumber, edamame, eggplant, endive, peas (garden peas) Vegetables such as peas, dried peas, table peas, garlic, horseradish, turnip cabbage, leeks, lentils, lettuce, melons, mushrooms (cultivated), mustard and other leafy greens, okra, onion, parsley, parsley, pepper, potato, prickly pear, pumpkin, radish, rhubarb, rutabaga, burdock, spinach, squash (summer and winter squash), sweet corn, sweet potato, Swiss chard, taro, tomato / grape nightshade, turnip and watermelon; agricultural crops such as sugar beets, sugarcane, tobacco, peanuts, and soybeans; Oilseed crops such as rapeseed (canola), mustard, camelina, crambe, sunflower, poppy, sesame and safflower; Forage crops such as alfalfa, clover, cowpea, vetch, sainfoin, lupine, fodder beet, rye, Kentucky bluegrass, fescue, and orchardgrass; Fiber crops such as cotton, flax, hemp, jute and sisal; forest vegetation, including coniferous species such as larch, fir or pine, temperate and tropical hardwoods (e.g. oak, birch, beech, teak or mahogany), as well as dry zone tree species such as eucalyptus; horticultural crops such as hops, maple (maple syrup), tea, rubber plants and turfgrasses (e.g., bentgrass, Kentucky bluegrass, ryegrass, fescue, corngrass, centipedegrass, crested hairgrass, Japanese larvae, St. Augustine grass, lawn grass, moss, timothy grass, and broadleaf grass); Examples include begonias, dahlias, geraniums, balsams, petunias, coleus, marigolds, pansies, snapdragons, saintpaulia, azaleas, chrysanthemums, flower bulbs, hydrangeas, lilies, orchids, poinsettias, roses, astilbes, goldenrods, delphiniums, dianthus, heucheras, hostas, phlox, rudbeckias, salvias, vinca, columbines, hostas, and chrysanthemums (garden floriculture, greenhouse and nursery plants including flowers, broad-leaved or evergreen trees such as chrysanthemum, ivy, ornamental grasses, peonies, delphiniums, gladioli, irises, snapdragons, tulips, eucalyptus, pittosporum, ferns, anthuriums, dieffenbachia, dracaena, figs, philodendrons, spathiphyllum, bromeliads, cacti, palms, balsam firs, spruces, Japanese pine, Fraser fir, noble fir, Scots pine, white pine, magnolia, ash, elm, ornamental cherry, ornamental plum, hawthorn, redbud and rowan berry; Propagation material such as bare seedlings, cuttings, liners, plug seedlings, seeds, tissue culture plantlets and prefinished plants; For example, allspice, Angelica spp., anise, annatto, yellow laurel, basil (all species), bay laurel (cultivated species), bladderwrack (seaweed), Bolivian coriander, borage, calendula (herbal use), candlenut, capers, caraway, cardamom, cassia spice, cinnamon, clary sage, cloves, catnip, chamomile, chervil, chicory, cicely, cilantro, comfrey, coriander, mustard greens, cumin, curry, dill, fennel, fenugreek, Culinary herbs and spices such as fillet (cultivated species), fingerroot, galangal, ginger, hops, horehound, hyssop, lavender, lemon balm, lemon thyme, lovage, mace, mahaleb, marabaltum, marjoram, mint (all species), mugwort, nutmeg, oregano, orris root, paprika, parsley, pepper, rosemary, rue, saffron, sage (all species), savory (all species), wood sorrel, tarragon, thyme, turmeric, vanilla, horseradish, and watercress; and Medicinal herbs such as arum, Artemisia spp., astragalus, Bordeaux, comfrey, coneflower, fenugreek, feverfew, foxglove, ginkgo, ginseng, goat's root, goldenseal, gypsywort, horehound, horsetail, lavender, licorice, marshmallow, mullein, nettle, passionflower, patchouli, peperomia, pokeweed, skullcap, wood sorrel, St. John's wort, senna, sowberry, stevia, tansy, witch hazel, ageratum, wormwood, yarrow, yerba buena, and ylang-ylang.

[0097] This list does not represent any limitation, however, preferably the useful plants may be selected from the group consisting of wheat, barley, rice, soybean, apple, almond, cherry, raspberry, grape, cucumber, peanut, tomato, strawberry, citrus fruits and banana.

[0098] The term "useful plants" should also be understood to include useful plants that have been rendered resistant to herbicides such as bromoxynil or to certain classes of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron, and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, etc.) by conventional breeding or genetic engineering methods. An example of a crop that has been rendered resistant to imidazolinones, such as imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered resistant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant corn varieties available commercially under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0099] The term "useful plants" should also be understood to include useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria. Examples of toxins that may be expressed include delta-endotoxins, vegetative insecticidal proteins (Vips), insecticidal proteins of nematode symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi.

[0100] An example of a crop modified to express a Bacillus thuringiensis toxin is Bt corn KnockOut® (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticide resistance and therefore expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to multiple pests (so-called overlapping transgenic events when created by genetic modification). For example, plants can be herbicide-resistant and simultaneously capable of expressing insecticidal proteins, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0101] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, such as insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as the δ-endotoxins CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c, or vegetative insecticidal proteins (VIPs), such as VIP1, VIP2, VIP3 or VIP3A; or insecticidal proteins from Photorhabdus species, such as Photorhabdus luminescens, Xenorhabdus nematophilus, for example. insecticidal proteins of nematode-symbiotic bacteria such as Xenorhabdus spp. or Xenorhabdus spp.; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, ruffin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0102] In the context of the present invention, delta-endotoxins, such as CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c, or trophic insecticidal proteins (VIP), such as VIP1, VIP2, VIP3 or VIP3A, are understood to also refer in particular to hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by de novo combination of different domains of these proteins (see, for example, WO 02 / 15701). An example of a truncated toxin is the truncated CryIA(b) expressed in Bt11 maize from Syngenta Seed SAS, as described below. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, in the case of CryIIIA055, a cathepsin D-recognition sequence is inserted into the CryIIIA toxin (see WO 03 / 018810).

[0103] Examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0104] Processes for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90 / 13651.

[0105] The toxins contained in the genetically modified plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0106] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants are: YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Rootworm® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); NatureGard® and Protecta®.

[0107] Further examples of such genetically modified crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seed SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically engineered maize (Zea mays) conferring resistance to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated CryIA(b) toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT.

[0108] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seed SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically engineered maize (Zea mays) resistant to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of CryIA(b) toxin. Bt176 maize also transgenicly expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0109] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seed SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance through transgenic expression of a modified CryIIIA toxin. The toxin is Cry3A055 modified by the insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0110] 4. MON863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the CryIIIB(b1) toxin and confers resistance to certain coleopteran insects.

[0111] 5. IPC531 Cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium.

[0112] 6. 1507 corn, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain lepidopteran insects, and for expression of the protein PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0113] 7. NK603 x MON810 corn, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This conventional hybrid corn variety is the result of crossing the genetically engineered varieties NK603 and MON810. NK603 x MON810 corn transgenicly expresses the protein CP4 EPSPS from Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (containing glyphosate), and the CryIA(b) toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0114] The term "useful plants" should also be understood to include useful plants that have been genetically modified using DNA recombinant techniques so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "infection-specific proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and genetically modified plants that are able to synthesize such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0115] Antipathogenic substances that can be expressed by such genetically modified plants include, for example, ion channel blockers, such as sodium and calcium channel blockers, e.g., viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; so-called "infection-specific proteins" (PRPs; see, for example, EP-A-0 392 225); antipathogenic substances produced by microorganisms, such as peptide or heterocyclic antibiotics (see, for example, WO 95 / 33818), or proteins or polypeptide factors involved in plant pathogen defense (the so-called "plant disease resistance genes" described in WO 03 / 000906).

[0116] The compositions of the present invention are particularly effective in controlling or preventing phytopathogenic diseases caused by certain phytopathogenic fungi, in particular powdery mildew, rust, leaf spot, late blight or mold, in cereal grains, fruits and tree nuts, vegetables, field crops, oilseed crops, fodder crops, forest plants, horticultural crops, floriculture, greenhouse and nursery plants, propagation material, culinary herbs and spices, and medicinal plants, as follows: Alternaria solani, preferably in tomatoes.

[0117] Alternaria alternata, preferably in eggplant.

[0118] Alternaria porri, preferably in onions.

[0119] Botrytis cinerea, preferably in tomatoes, peppers, onions, pome fruits, stone fruits, kiwi, blueberries, sugar beets or grapes.

[0120] Botrytis allii, preferably in onions.

[0121] Botrytis squamosa, preferably in onions.

[0122] Cercospora capsici, preferably in peppers.

[0123] Corynespora cassiicola, preferably in tomato.

[0124] Guignardia bidwellii, preferably in grapes.

[0125] Preferably Monilinia fructicola in cherries, peaches, plums, prunes, nectarines or almonds.

[0126] Monilinia fructigena, preferably in cherries, peaches, plums, prunes, nectarines or almonds.

[0127] Monilinia laxa, preferably in cherries, peaches, plums, prunes, nectarines or almonds.

[0128] Phomopsis viticola, preferably in grapes.

[0129] Podosphaera leucotricha, preferably on apples.

[0130] Preferably Podosphaera xanthii, in the Cucurbitaceae family.

[0131] Pseudopezicula tracheiphila, preferably in grapes.

[0132] Uncinula necator, preferably in grapes.

[0133] Preferably, Venturia inaequalis in apples.

[0134] Furthermore, the composition of the present invention is effective against Alternaria spp., Ascochyta spp., Botrytis cinerea, Cercospora spp., Claviceps purpurea, grass spot fungi, Colletotrichum spp., Epicoccum spp., Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Fusarium subglutinans, Fusarium spp. ... subglutinans, Gaeumannomyces graminis, Helminthosporium spp., Microdochium nivale, Phoma spp., Pyrenophora graminea, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia cerealis, Sclerotinia spp., Septoria spp., Sphacelotheca reilliana, Tilletia spp., Typhula incarnata incarnata, Urocystis occulta, Ustilago spp. or Verticillium spp.It is particularly effective against seed-borne and soil-borne diseases such as cereals, wheat, barley, rye, or oats; maize; rice; cotton; soybeans; turf; sugar beet; oilseed rape; potato; peas, lentils, or chickpeas; and sunflower.

[0135] Furthermore, the composition according to the present invention may be effective against Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Mucor piriformis, Penicillium italicum, Penicillium solitum, Penicillium digitatum or Penicillium expansum. expansum), especially against post-harvest diseases of fruit pathogens such as pome fruits, e.g. apple and pear, stone fruits, e.g. peaches and plums, citrus fruits, melons, papayas, kiwi, mango, berries, e.g. strawberries, avocados, pomegranates and bananas, and tree nuts.

[0136] The compositions of the present invention can also be used in crop enhancement, where "crop enhancement" as used herein means improved plant vigor, improved plant quality, improved tolerance to stress factors, and / or improved input use efficiency.

[0137] In the present invention, "improved plant vigor" means a qualitative or quantitative improvement in a particular trait when compared to the same trait in a control plant grown under the same conditions in the absence of the method of the present invention. Such traits include, but are not limited to, early and / or improved germination, improved germination, ability to use fewer seeds, increased root growth, a more developed root system, increased nodulation, increased shoot growth, increased tillers, more vigorous tillers, more productive tillers, increased or improved plant erection, less plant verse (lodging), increased and / or improved plant height, increased plant weight (fresh or dry), larger leaf blades, greener leaf color, increased pigment content, increased photosynthetic activity, earlier flowering, longer panicles, earlier grain set, increased seed, fruit, or pod size, increased number of pods or panicles, increased number of seeds per pod or panicle, increased seed mass, enhanced seed filling, fewer basal leaves, delayed senescence, improved plant vigor, increased amino acid levels in storage tissues, and / or less required inputs (e.g., less required fertilizer, water, and / or labor). Plants with improved vigor can have an increase in any of the foregoing traits, or any combination or two or more of the foregoing traits.

[0138] In the present invention, "improved plant quality" means a qualitative or quantitative improvement in a particular trait when compared to the same trait in a control plant grown under the same conditions in the absence of the method of the present invention. Such traits include, but are not limited to, improved plant appearance, reduced ethylene (reduced production and / or suppressed susceptibility), improved quality of harvested products such as seeds, fruits, leaves, vegetables, etc. (such improved quality may be manifested as improved visual appearance of the harvested product), improved carbohydrate content (e.g., increased sugar and / or starch amounts, improved sugar acid ratios, reduced reducing sugars, increased rate of sugar production), improved protein content, improved oil content and composition, improved nutritional value, reduced anti-nutritional compounds, improved organoleptic properties (e.g., improved taste), and / or improved consumer health benefits (e.g., increased levels of vitamins and antioxidants), improved post-harvest properties (e.g., enhanced shelf life and / or storage stability, easier processability, easier compound extraction), more uniform crop development (e.g., synchronized germination, flowering, and / or fruit set of plants), and / or improved seed quality (e.g., for use in the next growing season). Plants with improved quality may have an increase in any of the traits mentioned above, or in any combination or two or more of the traits mentioned above.

[0139] In the present invention, "improved tolerance to a stress factor" means that a particular trait is qualitatively or quantitatively improved compared to the same trait in a control plant grown under the same conditions in the absence of the method of the present invention. Such traits include, but are not limited to, increased tolerance and / or resistance to abiotic stress factors that cause suboptimal growth conditions, such as drought (e.g., any stress that results in a lack of water in the plant, insufficient water uptake capacity, or reduced water supply to the plant), cold exposure, heat exposure, osmotic stress, UV stress, flooding, increased salt (e.g., in the soil), increased mineral exposure, ozone exposure, high light exposure, and / or limited availability of nutrients (e.g., nitrogen and / or phosphorus nutrients). Plants with improved tolerance to a stress factor can have an increase in any of the aforementioned traits, or any combination or two or more of the aforementioned traits. In the case of drought and nutrient stress, such improved tolerance can result, for example, from more efficient uptake, use, or retention of water and nutrients.

[0140] In the present invention, "improved input use efficiency" means that a plant can grow more efficiently using a given input level compared to the growth of a control plant grown under the same conditions in the absence of the method of the present invention. Specifically, inputs include, but are not limited to, fertilizer (nitrogen, phosphorus, potassium, micronutrients, etc.), light, and water. A plant with improved input use efficiency can have improved use of any of the aforementioned inputs or any combination of two or more of the aforementioned inputs.

[0141] Other crop enhancements of the present invention include reduced plant height or reduced tillering, which are beneficial traits in crops or conditions where it is desirable to have less biomass and fewer tillers.

[0142] Any or all of the above crop enhancements may result in improved crop yields, for example, by improving plant physiology, plant growth and development, and / or plant architecture. In the context of the present invention, "yield" includes, but is not limited to, (i) increased biomass production, grain yield, starch content, oil content, and / or protein content, which may result from (a) an increase in the amount produced by the plant itself, or (b) improved ability to harvest the plant; (ii) improved crop composition (e.g., improved sugar-acid ratio, improved oil composition, increased nutritional value, reduced anti-nutritional compounds, increased consumer health benefits); and / or (iii) increased / facilitated ability to harvest the crop, improved crop processability, and / or better storage stability / shelf life. Increased yield of agricultural plants, where quantitative measurements can be made, means that the yield of a product of the respective plant is increased by a measurable amount over the yield of the same product of a plant produced under the same conditions but without the application of the present invention. According to the present invention, it is preferred that yield is increased by at least 0.5%, more preferably at least 1%, even more preferably at least 2%, and even more preferably at least 4%, preferably 5% or more.

[0143] Any or all of the above crop intensification may result in improved land utilization; that is, land that was previously unavailable or suboptimal for cultivation may become available. For example, plants that exhibit an increased ability to survive drought conditions may become cultivated in areas with suboptimal rainfall, such as perhaps the fringes of deserts or even the desert itself.

[0144] In one aspect of the invention, crop enhancement is achieved in the substantial absence of pressure from pests and / or diseases and / or abiotic stress. According to a further aspect of the invention, improved plant vigor, stress tolerance, quality and / or yield is achieved in the substantial absence of pressure from pests and / or diseases. For example, pests and / or diseases may be controlled by an insecticide treatment applied prior to or simultaneously with the method of the invention. In yet another aspect of the invention, improved plant vigor, stress tolerance, quality and / or yield is achieved in the substantial absence of pressure from pests and / or diseases. In a further embodiment, improved plant vigor, quality and / or yield is achieved in the absence or substantial absence of abiotic stress.

[0145] The composition of the present invention may be used in the field of protecting stored goods from fungal attack. In the present invention, the term "storage goods" is understood to mean natural substances of plant and / or animal origin and their processed forms, derived from their natural life cycle, for which long-term protection is desired. Stored goods of plant origin, such as plants or parts thereof (e.g., stems, leaves, tubers, seeds, fruits, or grains), can be protected in a freshly harvested state or in a processed form, such as pre-dried, moistened, crushed, ground, pressed, or roasted. The definition of stored goods also includes wood in the form of raw wood (e.g., construction timber, electricity transmission towers, and fences) and wood in the form of finished products (e.g., furniture or wooden products). Stored goods of animal origin include leather, leather products, fur, and hair. The composition of the present invention can prevent adverse effects such as decay, discoloration, or mold growth. Preferably, "storage products" is understood to mean natural substances of plant origin and / or their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, soft fruits and citrus fruits and their processed forms. In another preferred embodiment of the invention, "storage products" is understood to mean trees.

[0146] Therefore, a further aspect of the present invention is a method for protecting stored items which comprises applying to the stored items a composition of the present invention.

[0147] The composition of the present invention can also be used in the field of protecting industrial raw materials from fungal attack.In the present invention, the term "industrial raw materials" includes paper; carpets; buildings; cooling and heating systems; wallboards; ventilation and air-conditioning systems, etc.; preferably, "industrial raw materials" is understood to mean wallboards.The composition of the present invention can prevent adverse effects such as decay, discoloration, or mold growth.

[0148] Some compositions of the present invention are systemically active and can be used as foliar, soil and seed treatment fungicides.

[0149] The compositions according to the invention are capable of inhibiting or eliminating phytopathogenic microorganisms occurring in plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different useful plants, while at the same time protecting subsequently growing plant parts from attack by phytopathogenic microorganisms.

[0150] The compositions according to the invention can be applied to phytopathogenic microorganisms, useful plants threatened by microbial attack, their habitats, their propagation material, storage articles or technical materials.

[0151] The compositions according to the invention can be applied before or after the infection of useful plants, their propagation material, storage articles or technical material by microorganisms.

[0152] The compositions of the present invention can also be used in the field of protecting industrial materials from fungal attack. According to the present invention, the term "industrial material" refers to non-living materials prepared for industrial use. For example, industrial materials intended to be protected from fungal attack can be adhesives, glues, paper, cardboard, fabrics, carpets, leather, wood, structures, paints, plastic articles, cooling lubricants, water-based hydraulic fluids, and other materials that may be subject to microbial infestation or degradation. Cooling and heating systems, ventilation and air conditioning systems and components of production plants, such as cooling water circuits that may be damaged by microbial growth, can also be listed as materials to be protected. The compositions of the present invention can prevent adverse effects such as corrosion, discoloration, or mold.

[0153] The amount of the combination of the present invention to be applied will depend on various factors, such as the compound employed; the target of the treatment, e.g., plant, soil, or seed; the type of treatment, e.g., spraying, dusting, or seed dressing; the purpose of the treatment, e.g., prevention or treatment; the type of fungus to be controlled; or the time of application.

[0154] Compositions comprising component (A) in combination with component (B) may be applied, for example, in a single "ready-mixed" form, in multiple spray mixtures such as "tank mixes" composed of individual formulations of a single active ingredient, and sequentially, i.e., in combination with the single active ingredients when applied one after the other within a reasonably short time, such as a few hours or days. The order in which the compound of component (A) and the active ingredient of component (B) are applied is not critical to the operation of the present invention.

[0155] The compositions according to the invention are active ingredients which are useful preventively and / or curatively in the field of pest control, even at low application rates.

[0156] When used on useful plants, component (A) is used at a rate of 10g ai / ha to 500g ai / ha, together with 25g ai / ha to 1000g ai / ha of component (B). In one embodiment of the present invention, when used on useful plants, component (A) is used at a rate of 25g ai / ha to 500g ai / ha, together with 25g ai / ha to 1000g ai / ha of component (B).

[0157] In one preferred embodiment of the present invention, a method for controlling or preventing phytopathogenic diseases, in particular phytopathogenic fungi, on useful plants or their propagation material comprises applying to useful plants, their habitats or their propagation material a composition as defined by the present invention, wherein component (A) is applied at a rate of 10 g ai / ha to 500 g ai / ha together with component (B) at a rate of 25 g ai / ha to 1000 g ai / ha.

[0158] In one embodiment of the present invention, a method for controlling or preventing phytopathogenic diseases, in particular phytopathogenic fungi, on useful plants or their propagation material comprises applying to the useful plants, their habitats or their propagation material a composition as defined by the present invention, wherein component (A) is applied at a rate of 25 g ai / ha to 500 g ai / ha together with component (B) at a rate of 25 g ai / ha to 1000 g ai / ha.

[0159] The method for controlling or preventing plant pathogenic diseases according to the present invention may be particularly effective against plant pathogenic fungi selected from the group consisting of Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula, and Venturia.

[0160] The method for controlling or preventing plant pathogenic diseases according to the present invention includes the steps of: controlling or preventing plant pathogenic diseases of Alternaria solani, Alternaria alternata, Alternaria porri, Botrytis cinerea, Botrytis allii, Botrytis squamosa, Cercospora capsici, Colletotrichum lagenarium, Corynespora cassiicola, Guignardia bidwellii, Monilinia fructicola, Monilinia fructigena, Monilinia axa, and the like. laxa, Penicillium digitatum, Penicillium italicum, Penicillium expansum, Phomopsis viticola, Podosphaera leucotricha, Podosphaera xanthii, Pseudopezicula tracheiphila, Septoria tritici, Uncinula necator, and Venturia inaequalis.

[0161] Preferred is a method for controlling or preventing plant pathogenic diseases, especially those caused by plant pathogenic fungi, which comprises applying a composition according to the invention to useful plants selected from the group consisting of cereal grains, fruits and tree nuts, vegetables, field crops, oilseed crops, fodder crops, forest plants, horticultural crops, floriculture, greenhouse and nursery plants, propagation material, culinary herbs and spices, and medicinal plants.

[0162] Further preferred is a method for controlling or preventing plant pathogenic diseases, particularly those caused by plant pathogenic fungi, which comprises applying the composition of the present invention to useful plants selected from the group consisting of wheat, barley, rice, soybean, apple, almond, cherry, raspberry, grape, cucumber, peanut, tomato, strawberry, citrus fruits and banana.

[0163] In one embodiment of the present invention, the method for controlling or preventing plant pathogenic diseases according to the present invention may be particularly effective against plant pathogenic fungi selected from the group consisting of Alternaria, Cercospora, Colletotrichum, Corynespora, Mycosphaerella, Phakopsora, Phomopsis and Septoria in soybean plants.

[0164] In one embodiment of the present invention, the method for controlling or preventing plant pathogenic diseases according to the present invention may be particularly effective against plant pathogenic fungi selected from the group consisting of Alternaria spp., Cercospora kikuchii, Cercospora sojina, Phakopsora pachyrhizi, and Septoria glycines in soybean plants.

[0165] In one embodiment of the present invention, the method for controlling or preventing plant pathogenic diseases according to the present invention comprises applying to a useful plant, its habitat, or its propagation material a composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) comprises aureobasidin A and component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, florylpicoxamide, fluopyram, pydiflumetofen, fluazinam, benzovindiflupyr, isoflucipram, and methyltetrapole.

[0166] According to one variant of this embodiment of the invention, component (A) comprises aureobasidin A and one or more other cyclic depsipeptides of formula (IA) or its stereoisomers.

[0167] According to another variant of this embodiment of the invention, component (A) comprises aureobasidin A and one or more cyclic depsipeptides of formula (IB) or its stereoisomers.

[0168] The method for controlling or preventing plant pathogenic diseases according to this embodiment of the invention can be particularly effective against plant pathogenic fungi selected from the group consisting of Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula, and Venturia.

[0169] It has been unexpectedly found that the compositions of the present invention can be advantageously used in methods for controlling or preventing plant pathogenic diseases according to this embodiment of the invention, as they exhibit synergistic interactions with a broad spectrum of activity, successfully allowing for the implementation of beneficial resistance management for the effective control of plant pathogens.

[0170] The present invention also provides a fungicidal composition comprising a synergistically effective amount of a combination of components (A) and (B) as described above, together with an agriculturally acceptable carrier and, optionally, a surfactant, in which the weight ratio of (A) to (B) is, as previously described herein, preferably from 100:1 to 1:1000, more preferably from 100:1 to 1:500, even more preferably from 50:1 to 1:200, and even more preferably from 20:1 to 1:40.

[0171] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), (EG), emulsion, water-in-oil (EO), emulsion, oil-in-water (EW), microemulsion (ME), oil dispersion (OD), oil-miscible flowable (OF), oil-miscible liquid (OL), soluble concentrate (SL), ultra-low volume suspension (SU), ultra-low volume liquid (UL), technical concentrate (TK), dispersible concentrate (DC), hydrate (WP), or any technically desirable formulation in combination with agriculturally acceptable adjuvants.

[0172] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with appropriate inert ingredients (diluents, solvents, fillers, and optionally other ingredients). Alternatively, conventional slow-release formulations can be employed when long-lasting efficacy is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain compounds that provide adjuvant effects. In some embodiments, the compositions of the present invention can be prepared by mixing a fermentation broth containing aureobasidin A and one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof with component (B). In some other embodiments, the compositions of the present invention can be prepared by mixing a fermentation broth containing persephacin A and one or more other cyclic depsipeptides of formula (IB) or stereoisomers thereof with component (B).

[0173] The seed dressing formulation is applied to seeds in a manner known per se, using the combination of the present invention and a diluent in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seeds. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[0174] Typically, the formulation contains 0.01 to 90% by weight of the active agent, 0 to 20% by weight of an agriculturally acceptable surfactant, and 10 to 99.99% by weight of solid or liquid inert formulation and formulation adjuvants. The active agent comprises at least a compound of formula (I), component (B), and optionally component (C), together with other active agents, particularly fungicides or preservatives. Concentrated forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application forms of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. While commercial products are preferably formulated as concentrates, end users will typically utilize diluted formulations.

[0175] Surprisingly, it has been found that a certain weight ratio of component (A) to component (B) can result in synergistic activity. Therefore, a further aspect of the present invention is a composition in which component (A) and component (B) are present in a synergistic amount. This synergistic activity is evident from the fact that the fungicidal activity of a composition containing component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and component (B). This synergistic activity extends the range of action of component (A) and component (B) in two ways. First, the application rates of component (A) and component (B) can be reduced while the action remains equally good, which means that even at low application rates where the two individual components are completely ineffective, the active ingredient mixture still achieves a high level of plant pathogen control. Second, the range of plant pathogens that can be controlled is substantially expanded.

[0176] A synergistic effect exists whenever the action of a combination of active ingredients is greater than the sum of the actions of the individual ingredients. The expected activity E for a given combination of active ingredients can be calculated according to the so-called COLBY formula as follows (COLBY, SR "Calculating synergistic and antagonistic responses of herbicide combinations". Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient (=ai) per litre of spray mixture X = % effect of active ingredient (A) using p ppm of active ingredient Y = % effect of the active ingredient (B) using q ppm of active ingredient.

[0177] According to COLBY, the expected (active) effect of active ingredients (A) + (B) using p + q ppm of active ingredients is:

number

[0178] When the actual observed effect (O) is greater than the expected effect (E), the effect of the combination is superadditive, i.e., synergy exists. In mathematical terms, synergy corresponds to a positive value of the difference (OE). In the case of a pure complementary addition of activity (expected activity), the difference (OE) is zero. A negative value of the difference (OE) indicates a loss of activity compared to the expected activity.

[0179] However, apart from the actual synergistic action with regard to fungicidal activity, the compositions of the present invention may also have surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability; improved toxicological and / or biotoxicological behavior; or improved properties of useful plants (germination, crop yield, more developed root system, increased tillers, increased plant height, larger leaf blades, fewer basal leaves, more powerful tillers, greener leaf color, less fertilizer required, less seed required, more productive tillers, earlier flowering, earlier grain production, less plant verse (lodging), increased shoot growth, improved plant vigor, and earlier germination, etc.).

[0180] The following examples are intended to illustrate the present invention and are not intended to limit the invention in any way. [Example]

[0181] Biological Examples The compositions of the present invention are tested for their biological (fungicidal) activity using application rates in which component (A) is applied in an amount of 25 g ai / ha to 1000 g ai / ha, together with 10 g ai / ha to 500 g ai / ha of component (B).

[0182] Compositions of the present invention are tested for their biological (bactericidal) activity as solutions in dimethyl sulfoxide (DMSO) using one or more of the following protocols (Examples 1-1 and 1-2). A standard description of the liquid culture test is provided in Example 1.

[0183] Aureobasidin A and its synthesis are known from Takesako et al., The Journal of Antibiotics, 1991, 44, 919-924. Aureobasidin A is isolated from the fermentation broth by extraction with ethyl acetate, followed by extraction of the ethyl acetate concentrate with a mixture of MeOH:HO (80% by volume) and cyclohexane (20% by volume), and purification by silica gel column chromatography (silica gel, elution with hexane:ethyl acetate), followed by reverse-phase column chromatography (RP18, elution with acetonitrile:HO). As mentioned above, component (B) of the composition is known, commercially available, and / or can be prepared using techniques known in the art and / or reported in the literature.

[0184] Example 1: Liquid medium test in well plates Freshly prepared or cryopreserved fungal mycelium fractions or conidial suspensions from fungal broth are mixed directly with the nutrient broth. A DMSO solution of the test compound (up to 10 mg / mL) is diluted 50-fold with 0.025% Tween 20, and 10 μl of this solution is pipetted into a 96-well microtiter plate. The nutrient broth containing the fungal spore / mycelium fraction is then added to achieve the final concentration of the test compound. The test plate is incubated in the dark at 24°C and 96% relative humidity (rh). Fungal growth inhibition is measured photometrically and visually after 3 to 7 days, depending on the pathogen response system, and the percentage of antifungal activity compared to the untreated test control is calculated.

[0185] Example 1-1: Botrytis cinerea (gray mold) Fungal conidia stored at low temperature were directly mixed into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compositions were placed in microtiter plates (96-well format), and then the nutrient broth containing the fungal conidia was added. The test plates were incubated at 24°C, and growth inhibition was determined photometrically after 72 hours.

[0186] Example 1-2: Alternaria solani (tomato / potato late blight) Fungal conidia stored at low temperature were directly mixed into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compositions were placed in microtiter plates (96-well format), and then the nutrient broth containing the fungal conidia was added. The test plates were incubated at 24°C, and growth inhibition was determined photometrically after 48 hours.

[0187] result The results of the above tests are shown in Tables 1 to 17. These data show that synergistic fungicidal activity is observed in combination with the other active ingredients of component (B) against Botrytis cinerea and Alternaria solani at certain weight ratios. According to COLBY, mathematically, the synergism factor SF corresponds to O / E. In agricultural practice, an SF of 1.1 or greater indicates a significant improvement over the purely complementary addition of activity (assumed activity), while an SF of 0.9 or less in practical application routines indicates a loss of activity compared to the assumed activity. Another aspect of the present invention may be as follows. [1] A fungicidal composition containing a mixture of components (A) and (B) as an active ingredient, wherein component (A) is a compound represented by formula (I-A1): [ka] or a stereoisomeric cyclic depsipeptide thereof; Component (B) is a respiratory inhibitor: (B.1) Cumoxystrobin, Cumoxystrobin, Dimoxystrobin, Enoxastrobin, Enestrobulin, Phenaminestrobin, Fenoxystrobin / Flufenoxystrobin, Flufenoxystrobin, Kresoximmethyl, Mandestrobin, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametstrobin, Pyraoxystrobin, Tri Floxystrobin, (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoic acid methyl ester, 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, (2E,3Z)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (2E,3Z)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3- Enamide, pyribencarb, triclopiricarb / chlorozinecarb, famoxadone, fenamidone, 1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, methyltetraprole, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one, 1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one, 1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]-methyl]phenyl]-4-methyl-tetrazol-5-one, 1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl] Q selected from the group consisting of 1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, pyriminostrobin, and bifujunci, o with inhibitors of complex III at the site; (B.2) Cyazofamid, amisulbrom, [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate, fenpicoxamide, [(6S,7R,8R)-8-benzyl-3-[[4-methoxy-3-(propanoyloxymethoxy)pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate, Q selected from the group consisting of [5-dioxonan-7-yl]-2-methylpropanoate, furoylpicoxamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl], and (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [(1S)-1-methyl-2-(o-tolyl)propyl]. i with inhibitors of complex III at the site; (B.3) Benzovindiflupyr, bixafen, fluindapyr, boscalid, carboxin, pyraziflumid, fenfuram, cyclobutrifluram, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide, sedaxane, pyrapropoin, isoflucipram, teklof Thalam, Thifluzamide, 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-tri Methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamidean inhibitor of complex II selected from the group consisting of 1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide; (B.4) other respiratory inhibitors selected from the group consisting of diflumetrim; tolfenpyrad; fenazaquin; nitrophenyl derivatives: binapacryl, dinobuton, dinocap, fluazinam, meptyldinocap, ferimzone; organometallic compounds: fentin salts, such as fentin acetate, fentin chloride or fentin hydroxide; ametoctrazine; and silthiofam, A disinfectant composition selected from the group consisting of: [2] The composition according to [1], wherein the weight ratio of (A) to (B) is 100:1 to 1:1000, preferably 100:1 to 1:500, more preferably 50:1 to 1:200, and even more preferably 20:1 to 1:40. [3] Component (A) is one or more other cyclic depsipeptides of formula (IA):

change

change

[10] A method for controlling or preventing plant pathogenic diseases, particularly plant pathogenic fungi, on useful plants or their propagation materials, the method comprising applying to the useful plant, its habitat, or its propagation materials a composition containing a mixture of components (A) and (B) as active ingredients, wherein component (A) comprises aureobasidin A, and component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, florylpicoxamide, fluopyram, pydiflumetofen, fluazinam, benzovindiflupyr, isoflucipram, and methyltetrapole.

[11] The method according to [9] or

[10] , wherein the component (A) is used at a rate of 10 g ai / ha to 500 g ai / ha together with the component (B) at a rate of 25 g ai / ha to 1000 g ai / ha.

[12] The method according to any one of [9] to

[11] above, wherein the plant pathogenic fungus is selected from the group consisting of Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula, and Venturia.

[13] The method according to any one of [9] to

[12] , wherein the useful plants are selected from cereal grains, fruits and tree nuts, vegetables, field crops, oilseed crops, fodder crops, forest plants, horticultural crops, floriculture, greenhouse and nursery plants, propagation materials, culinary herbs and spices, and medicinal plants.

[14] The method according to any one of [9] to

[13] above, wherein the method controls or prevents a plant pathogenic fungus selected from the group consisting of Alternaria, Cercospora, Colletotrichum, Corynespora, Mycosphaerella, Phakopsora, Phomopsis, and Septoria in a soybean plant.

[15] Use of a composition containing the component (A) and the component (B) described in any one of [1] to [8] above as a disinfectant.

[0188]

Table 3

[0189]

Table 4

[0190]

Table 5

[0191]

Table 6

[0192]

Table 7

[0193]

Table 8

[0194]

Table 9

[0195]

Table 10

[0196]

Table 11

[0197]

Table 12

[0198]

Table 13

[0199]

Table 14

[0200]

Table 15

[0201] Table 16

[0202]

Table 17

[0203]

Table 18

[0204]

Table 19

Claims

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound represented by formula (I-A1): 【Chemical 1】 or a stereoisomeric cyclic depsipeptide thereof; A fungicidal composition, wherein component (B) is a respiratory inhibitor selected from the group consisting of azoxystrobin, trifloxystrobin, florylpicoxamide, fluopyram, pydiflumetofen, fluazinam, benzovindiflupyr, isoflucipram, and methyltetrapole.

2. 10. The composition of claim 1, wherein the weight ratio of (A) to (B) is from 100:1 to 1:1000.

3. Component (A) may be one or more other cyclic depsipeptides of formula (IA): 【Chemistry 2】 (In the formula, R 1 is methyl or ethyl; X 1 , X 2 and X 3 Each of X is hydrogen, or 1 , X 2 and X 3 is hydrogen, fluorine or hydroxyl, provided that X 1 , X 2 and X 3 is fluorine or hydroxyl; X 4 is CH, S or hydroxymethylene; A 3 are N-methyl-L-phenylalanine (L-MePhe), L-phenylalanine (L-Phe), β-hydroxy-N-methyl-L-phenylalanine (L-β-OH-MePhe), ortho-fluoro-N-methyl-L-phenylalanine (L-o-F-MePhe), meta-fluoro-N-methyl-L-phenylalanine (L-m-F-MePhe), para-fluoro-N-methyl-L-phenylalanine (L-p-F-MePhe), meta-bromo-N-methyl-L-phenylalanine (L-m-Br-MePhe), and para-bromo -N-methyl-L-phenylalanine (L-p-Br-MePhe), meta-iodo-N-methyl-L-phenylalanine (L-m-I-MePhe), para-iodo-N-methyl-L-phenylalanine (L-p-I-MePhe), 3-phenyl-N-methyl-L-phenylalanine, 4-phenyl-N-methyl-L-phenylalanine, 3-(4-fluorophenyl)-N-methyl-L-phenylalanine, 4-(4-fluorophenyl)-N-methyl-L-phenylalanine, 3-(4-pyridinyl)-N-methyl-L-phenylalanine 4-(4-pyridinyl)-N-methyl-L-phenylalanine, 3-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(1-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-4-pyridinyl)-N-methyl-L-phenylalanine, 3-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 4-(2-chloro-5-pyridinyl)-N-methyl-L-phenylalanine, 3-[4-(piperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4- (piperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, 3-[4-(4-methylpiperazin-1-yl)phenyl]phenyl-N-methyl-L-phenylalanine, 4-[4-(4-methylpiperazin-1-yl)phen-1-yl]phenyl-N-methyl-L-phenylalanine, β-oxo-N-methyl-L-phenylalanine (L-β-oxo-MePhe), β-acetoxy-N-methyl-L-phenylalanine (L-β-AcO-MePhe), N-methyl-L-tyrosine (L-MeTyr),an α-amino acid residue selected from the group consisting of O-methyl-N-methyl-L-tyrosine [L-MeTyr(Me)], N-methyl-L-alanine (L-MeAla), N-methyl-L-serine (L-MeSer), N-methyl-D-phenylalanine (D-MePhe), N-methyl-D-alanine (D-MeAla), N-methyl-D-valine (D-MeVal), N-methyl-D-serine (D-MeSer) and N-methyl-L-serine (L-MeSer) residues; A 5 is an α-amino acid residue selected from the group consisting of L-allo-isoleucine (L-AIle), L-leucine (L-Leu), L-norleucine (L-Nle), L-norvaline (L-Nva), and L-valine (L-Val) residues; A 6 is an α-amino acid residue selected from the group consisting of N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAIle) and L-valine (L-Val) residues; A 7 is an α-amino acid residue selected from the group consisting of L-leucine (L-Leu), L-allo-isoleucine (L-AIle), and L-norvaline (L-Nva) residues; and A 8 β-hydroxy-N-methyl-L-valine (L-β-OH-MeVal), γ-hydroxy-N-methyl-L-valine (L-γ-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDH), 2,3 Val), N-methyl-3,4-didehydro-L-valine (L-MeDH 3,4 and N,β-dimethyl-L-aspartic acid (L-N,β-MeAsp) residues). The composition of claim 1 or claim 2, further comprising:

4. The composition according to any one of claims 1 to 3, wherein component (A) further comprises at least one other cyclic depsipeptide of formula (IA) or a stereoisomer thereof selected from the group consisting of aureobasidin E and aureobasidin G.

5. Component (A) is 10% to 99.9% by weight of a cyclic depsipeptide of formula (I-A1) or a stereoisomer thereof; 0.1% to 90% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof The composition of any one of claims 1 to 4, comprising:

6. Component (A) is 20% to 99.9% by weight of a cyclic depsipeptide of formula (I-A1) or a stereoisomer thereof; 0.1% to 80% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof; The composition of any one of claims 1 to 4, comprising:

7. Component (A) is 40% to 99.9% by weight of a cyclic depsipeptide of formula (I-A1) or a stereoisomer thereof; 0.1% to 60% by weight of one or more other cyclic depsipeptides of formula (IA) or stereoisomers thereof; The composition of any one of claims 1 to 4, comprising:

8. A composition according to any one of claims 1 to 7, further comprising an agriculturally acceptable carrier and / or formulation adjuvant, and optionally a surfactant.

9. A method for controlling or preventing phytopathogenic diseases in useful plants or their propagation material, the method comprising applying to said useful plants, their habitats or their propagation material a composition according to any one of claims 1 to 8.

10. A method for controlling or preventing plant pathogenic diseases in a useful plant or its propagation material, the method comprising applying to the useful plant, its habitat, or its propagation material a composition containing a mixture of components (A) and (B) as active ingredients, wherein component (A) comprises aureobasidin A, and component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, florylpicoxamide, fluopyram, pydiflumetofen, fluazinam, benzovindiflupyr, isoflucipram, and methyltetrapole.

11. 11. The method of claim 9 or claim 10, wherein component (A) is used at a rate of 10 g a.i. / ha to 500 g a.i. / ha, together with component (B) at 25 g a.i. / ha to 1000 g a.i. / ha.

12. The plant pathogenic fungi include Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, and the like.

12. The method according to any one of claims 9 to 11, wherein the fungus is selected from the group consisting of Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula and Venturia.

13. 13. The method according to any one of claims 9 to 12, wherein the useful plants are selected from cereal grains, fruits and tree nuts, vegetables, field crops, oilseed crops, fodder crops, forest plants, horticultural crops, floriculture, greenhouse and nursery plants, propagation material, culinary herbs and spices, and medicinal plants.

14. 14. The method of any one of claims 9 to 13, wherein the method controls or prevents plant pathogenic fungi selected from the group consisting of Alternaria, Cercospora, Colletotrichum, Corynespora, Mycosphaerella, Phakopsora, Phomopsis and Septoria in soybean plants.

15. Use of a composition comprising component (A) and component (B) according to any one of claims 1 to 8 as a disinfectant.

Images