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WO2025032053A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2025032053A1
WO2025032053A1 PCT/EP2024/072163 EP2024072163W WO2025032053A1 WO 2025032053 A1 WO2025032053 A1 WO 2025032053A1 EP 2024072163 W EP2024072163 W EP 2024072163W WO 2025032053 A1 WO2025032053 A1 WO 2025032053A1
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WIPO (PCT)
Prior art keywords
methyl
phenylalanine
component
aureobasidin
mephe
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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PCT/EP2024/072163
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English (en)
Inventor
Hanno Christian Wolf
Olivier Loiseleur
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Syngenta Crop Protection AG Switzerland
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Syngenta Crop Protection AG Switzerland
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Publication of WO2025032053A1 publication Critical patent/WO2025032053A1/fr
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/30—Microbial fungi; Substances produced thereby or obtained therefrom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the present invention relates to new fungicidal compositions for the control of fungi. Methods of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant or on propagation material thereof are also disclosed.
  • Aureobasidins are a group of antifungal cyclic depsipeptides first isolated from the filamentous fungus Aureobasidium pullulans R106 (EP352092A2, Takesako et al., 1991 , J. Antibiot. 44, 919-924, doi: 10.7164/antibiotics.44.919, Yoshikawa et al., 1993, J. Antibiot. 46, 1347-1354, doi: 10.7164/antibiotics.46.1347, and Awazu et al., 1995, J. Antibiot. 48, 525-527, doi: 10.7164/antibiotics.48.525). Aureobasidins show a wide spectrum of activity against fungi.
  • aureobasidins are disclosed for use in controlling a variety of phytopathogenic fungi on plants and seeds (EP0500264A1 , WO2018102345). Combinations of aureobasidins for the control of phytopathogenic fungi with one or more other active ingredients possessing different modes of action have also been disclosed (WO2021245102A1 , WO2021245103A1 , WO2021245104A1 , WO2021245105A1 , WO2021245106A1).
  • the present invention discloses an unexpected synergistic fungicidal effect of a composition comprising a cyclic depsipeptide represented by formula (I), in particular Aureobasidin A (AbA), and thymol.
  • formula (I) a cyclic depsipeptide represented by formula (I), in particular Aureobasidin A (AbA), and thymol.
  • a method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant or on propagation material thereof comprising applying to the plant, locus thereof, or propagation material thereof, a composition as defined according to the invention.
  • the method comprises applying to the plant or locus thereof a composition according to the invention, more preferably to the plant.
  • the method comprises applying to the propagation material of the plant a composition according to the invention.
  • composition comprising the components A and B as defined according to the invention as a fungicide.
  • compositions of the invention may be effective against a wider spectrum of such fungi than can be combated with the individual active ingredients when used alone.
  • the benefits provided by certain fungicidal compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability).
  • a residue of a chemical species refers to a derivative of a moiety that is present in a particular product. To form the product, at least one atom of the moiety is replaced by a bond to a second moiety, such that the product contains a derivative of a moiety.
  • an amino acid residue in a product may refer to a cyclic peptide described herein having an amino acid incorporated therein through formation of one or more peptide bonds, and such residues may be referred to interchangeably herein as an amino acid or an amino acid residue.
  • cyclic depsipeptide refers to a cyclic peptide consisting, in sequence, of units derived from a 2-hydroxy-3-methylalkanoic acid or a 2-hydroxy-3- hydroxymethylalkanoic acid and from the following a-amino acid residues: a first a-amino acid residue selected from N-methyl-L-valine (L-MeVal) and L-valine (L-Val), a second a-amino acid residue selected from L-phenylalanine (L-Phe), 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), 2-hydroxy-phenylalanine (L-2OH-Phe), 3-hydroxy-phenylalanine (
  • the 2-hydroxy-3-methylalkanoic acid may be 2(R)-hydroxy- 3(R)-methylpentanoic acid, 2(R)-hydroxy-3-methylbutanoic acid, 2,5-dihydroxy-3-methyl-pentanoic acid, 2,4-dihydroxy-3-methyl-pentanoic acid, or D-2-hydroxyisovaleric acid, and preferably may be 2(R)-hydroxy-3(R)-methylpentanoic acid or 2(R)-hydroxy-3-methylbutanoic acid.
  • the 2-hydroxy-3- hydroxymethylalkanoic acid may be 2-hydroxy-3-hydroxymethylpentanoic acid.
  • the component A according to the invention comprises an active ingredient, preferably wherein the active ingredient comprises a fungicide.
  • the cyclic depsipeptide according to the invention is an active ingredient, preferably a fungicide.
  • the component A according to the invention comprises a cyclic depsipeptide represented by formula (I) or a stereoisomer thereof: wherein:
  • R 1 is methyl or ethyl
  • R 2 is methyl, hydroxymethyl, or hydroxyethyl
  • R 3 is hydrogen or methyl; each of X 1 , X 2 , and X 3 is hydrogen, or X 1 , X 2 , and X 3 are hydrogen, fluorine, or hydroxyl, with the proviso that only one of X 1 , X 2 , and X 3 is fluorine or hydroxyl;
  • X 4 is CH2, S, or hydroxymethylene
  • a 3 is an a-amino acid residue selected from: N-methyl-L-phenylalanine (L-MePhe), L- phenylalanine (L-Phe), p-hydroxy-N-methyl-L-phenylalanine (L-p-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), para-bromo-N-methyl-L-phenylalanine (L-p-Br-MePhe), meta-iodo-N-methyl-L-phenylalanine (L-m-l- MePhe), para
  • a 5 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), L- norleucine (L-Nle), L-norvaline (L-Nva), L-valine (L-Val), and L-methioninesulfoxide (L-Met(O)) residues;
  • a 6 is an a-amino acid residue selected from: N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAlle), and L-valine (L-Val) residues;
  • a 7 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), and L-norvaline (L-Nva) residues; and
  • a 8 is an a-amino acid residue selected from: p-methyl-L-phenylalanine (L-p-Phe), p-hydroxy- N-methyl-L-valine (L-p-OH-MeVal), y-hydroxy-N-methyl-L-valine (L-y-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDH2,3Val), N-methyl-3,4-didehydro- L-valine (L-MeDHs.A/al), N-methyl-L-phenylalanine (L-MePhe), p-hydroxy-N-methyl-L-phenylalanine (L-p-OH-MePhe), N-methyl-L-threonine (L-MeThr), sarcosine (Sar), and N,p-dimethyl-L-aspartic acid (L-
  • p-R 4 O-N-methyl-L-phenylalanine is p-acetoxy-N-methyl-L-phenylalanine (L-p- AcO-MePhe).
  • the component A according to the invention comprises a cyclic depsipeptide represented by formula (la) or a stereoisomer thereof: wherein:
  • R 1 is methyl or ethyl; each of X 1 , X 2 , and X 3 is hydrogen, or X 1 , X 2 , and X 3 are hydrogen, fluorine, or hydroxyl, with the proviso that only one of X 1 , X 2 , and X 3 is fluorine or hydroxyl;
  • X 4 is CH2, S, or hydroxymethylene;
  • a 3 is an a-amino acid residue selected from: N-methyl-L-phenylalanine (L-MePhe), L- phenylalanine (L-Phe), p-hydroxy-N-methyl-L-phenylalanine (L-p-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), para-bromo-N-methyl-L-phenylalanine (L-p-Br-MePhe), meta-iodo-N-methyl-L-phen
  • a 5 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), L- norleucine (L-Nle), L-norvaline (L-Nva), L-valine (L-Val), and L-methioninesulfoxide (L-Met(O)) residues;
  • a 6 is an a-amino acid residue selected from: N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAlle), and L-valine (L-Val) residues;
  • a 7 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), and L-norvaline (L-Nva) residues; and
  • a 8 is an a-amino acid residue selected from: p-methyl-L-phenylalanine (L-p-Phe), p-hydroxy- N-methyl-L-valine (L-p-OH-MeVal), y-hydroxy-N-methyl-L-valine (L-y-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDFL.sVal), N-methyl-3,4-didehydro- L-valine (L-MeDHs.A/al), N-methyl-L-phenylalanine (L-MePhe), p-hydroxy-N-methyl-L-phenylalanine (L-p-OH-MePhe), N-methyl-L-threonine (L-MeThr), sarcosine (Sar), and N,p-dimethyl-L-aspartic acid (L
  • p-R 4 O-N-methyl-L-phenylalanine is p-acetoxy-N-methyl-L-phenylalanine (L-p- AcO-MePhe).
  • the compound of formula (I) according to the invention is selected from a compound 1.001 to 1 .044 listed in Table A (below) or a compound 2.001 to 2.035 listed in Table B (below).
  • Table A Table A
  • Table B Table B
  • the following lists provides definitions, including preferred definitions, for substituents R 1 , R 2 , R 3 , X 1 , X 2 , X 3 , A 3 , X 4 , A 5 , A 6 , A 7 , and A 8 with reference to the compounds of formula (I) of the present invention.
  • any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.
  • Table A This table discloses 44 compounds of formula (I), wherein R 1 , R 2 , R 3 , X 1 , X 2 , X 3 , A 3 , X 4 , A 5 , A 6 , A 7 , and A 8 are as set forth in Table A below. “ID” indicates the (abbreviated) Aureobasidin variant the structure is also known as.
  • Table B This table discloses 35 compounds of formula (I), wherein R 1 is ethyl, R 2 is methyl, R 3 is methyl, X 4 is CH2, A 6 is L-MeVal and A 7 is L-Leu and X 1 , X 2 , X 3 , A 3 , A 5 , and A 8 are as set forth in Table B below.
  • the component A according to the invention comprises a cyclic depsipeptide selected from the group consisting of: Aureobasidin A (AbA), Aureobasidin B (AbB), Aureobasidin C (AbC), Aureobasidin D (AbD), Aureobasidin E (AbE), Aureobasidin F (AbF), Aureobasidin G (AbG), Aureobasidin H (AbH), Aureobasidin I (Abl), Aureobasidin J (AbJ), Aureobasidin K (AbK), Aureobasidin L (AbL), Aureobasidin M (AbM), Aureobasidin N (AbN), Aureobasidin O (AbO), Aureobasidin P (AbP), Aureobasidin Q (AbQ), Aureobasidin R (AbR), Aureobasidin S1 (AbS1), Aureobasidin S2a (AbS2
  • the cyclic depsipeptide is selected from the group consisting of: Aureobasidin A (AbA), Aureobasidin E (AbE), Aureobasidin G (AbG), Aureobasidin D (AbD), and Aureobasidin I (Abl). More preferably, the cyclic depsipeptide is selected from the group consisting of: Aureobasidin A (AbA), Aureobasidin E (AbE), and Aureobasidin G (AbG).
  • the component A according to the invention comprises Aureobasidin A (AbA).
  • the compound of formula (I) according to the invention is Aureobasidin A (AbA) or a stereoisomer thereof, preferably represented by formula (lb):
  • Aureobasidin A represents a cyclic depsipeptide of formula (lb) or a stereoisomer thereof consisting, in sequence, of 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-Alle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu) and p-hydroxy-N-methyl-L- valine (L-p-OH-MeVal).
  • a known stereoisomer of AbA is Aureobasidin T1 (AbT1), a cyclic depsipeptide of formula (lb) or a stereoisomer thereof consisting, in sequence, of units derived from 2(R)-hydroxy-3(S)- methylpentanoic acid ((2R,3S)-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-Alle), N-methyl-L-valine (L- MeVal), L-leucine (L-Leu) and p-hydroxy-N-methyl-L-valine (L-p-OH-MeVal).
  • AbT1 Aureobasidin T1
  • lb cyclic depsipeptide of formula (lb) or a stereoisomer thereof consist
  • the compound of formula (I) according to the invention comprises Aureobasidin E (AbE) or a stereoisomer thereof, preferably represented by formula (Ic):
  • Aureobasidin E represents a cyclic depsipeptide of formula (Ic) or a stereoisomer thereof consisting, in sequence, of units derived from 2(R)-hydroxy-3(R)-methylpentanoic acid ((2R,3R)-Hmp), N-methyl- L-valine (L-MeVal), L-phenylalanine (L-Phe), p-hydroxy-N-methyl-L-phenylalanine (L-p-OH-MePhe), L-proline (L-Pro), L-allo-isoleucine (L-Alle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu) and p- hydroxy-N-methyl-L-valine (L-p-OH-MeVal).
  • the compound of formula (I) according to the invention comprises Aureobasidin G (AbG) or a stereoisomer thereof, preferably represented by formula (Id):
  • Aureobasidin G represents a cyclic depsipeptide of formula (Id) or a stereoisomer thereof consisting, in sequence, of 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-Alle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu) and N-methyl-L-valine (L- MeVal).
  • the compound of formula (I) according to the invention comprises Aureobasidin D
  • Aureobasidin D represents a cyclic depsipeptide of formula (le) or a stereoisomer thereof consisting, in sequence, of 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-Alle), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu) and y-hydroxy-N-methyl-L- valine (L-y-OH-MeVal).
  • the compound of formula (I) according to the invention comprises Aureobasidin I (Abl) or a stereoisomer thereof, preferably represented by formula (If):
  • Aureobasidin I represents a cyclic depsipeptide of formula (If) or a stereoisomer thereof consisting, in sequence, of 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- leucine (L-Leu), N-methyl-L-valine (L-MeVal), L-leucine (L-Leu) and p-hydroxy-N-methyl-L-valine (L-p- OH-MeVal).
  • the component A according to the invention additionally comprises one or more other cyclic depsipeptides represented by formula (I) or a stereoisomer thereof.
  • the component A according to the invention additionally comprises one or more other cyclic depsipeptides represented by formula (la) or a stereoisomer thereof.
  • the component A according to the invention comprises two or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A comprises Aureobasidin A and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A comprises Aureobasidin E and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A comprises Aureobasidin A and Aureobasidin E or Aureobasidin G.
  • the component A comprises Aureobasidin A and Aureobasidin D or Aureobasidin I.
  • the component A according to the invention additionally further comprises at least one other cyclic depsipeptide of formula (I) or a stereoisomer thereof selected from the group consisting of Aureobasidin E (AbE) and Aureobasidin G (AbG).
  • the component A according to the invention comprises two or more cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A comprises Aureobasidin A and one or more other cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A comprises Aureobasidin E and one or more other cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A comprises: (i) Aureobasidin A; and (ii) Aureobasidin E or Aureobasidin G.
  • the component A comprises: (i) Aureobasidin A; and (ii) Aureobasidin D or Aureobasidin I.
  • the component A comprises: (i) Aureobasidin A or a stereoisomer thereof; and (ii) Aureobasidin E or a stereoisomer thereof, or Aureobasidin G or a stereoisomer thereof.
  • the component A comprises: (i) Aureobasidin A or a stereoisomer thereof; and (ii) Aureobasidin D or a stereoisomer thereof, or Aureobasidin I or a stereoisomer thereof.
  • the component A according to the invention additionally further comprises at least one other cyclic depsipeptide of formula (I) or a stereoisomer or of formula (la) or a stereoisomer thereof selected from the group consisting of Aureobasidin E (AbE) and Aureobasidin G (AbG).
  • the component A according to the invention comprises Aureobasidin A and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1 .001 to 1 .005 and 1 .007 to 1 .044 as set forth in Table A.
  • the component A comprises Aureobasidin A and at least one other cyclic depsipeptide of formula (la) or a stereoisomer thereof selected from the group consisting of Aureobasidin E and Aureobasidin G.
  • the component A according to the invention 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 2.035 as set forth in Table B.
  • component A comprises a strain of Aureobasidium pullulans, generally a strain of Aureobasidium pullulans R106.
  • one or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above can be obtained from a fermentation broth of a strain of Aureobasidium pullulans, generally a strain of Aureobasidium pullulans R106.
  • fertilization broth refers to a composition obtained from a process of fermentation of a strain.
  • the component A is a fermentation broth comprising two or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A is a fermentation broth comprising two or more cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A is a fermentation broth comprising Aureobasidin A and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof as defined above.
  • the component A is a fermentation broth comprising Aureobasidin E and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof as defined above.
  • the component A is a fermentation broth comprising Aureobasidin A or a stereoisomer thereof.
  • the component A comprises a fermentation broth comprising Aureobasidin A or a stereoisomer thereof.
  • the component A comprises a fermentation broth comprising Aureobasidin A or a stereoisomer thereof and Aureobasidin E or a stereoisomer thereof.
  • the component A comprises a fermentation broth comprising Aureobasidin A or a stereoisomer thereof and Aureobasidin G or a stereoisomer thereof.
  • the component A comprises a fermentation broth comprising Aureobasidin A or a stereoisomer thereof and Aureobasidin D or a stereoisomer thereof.
  • the component A comprises a fermentation broth comprising two or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A comprises a fermentation broth comprising two or more cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A comprises a fermentation broth comprising Aureobasidin A and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof as defined above.
  • the component A further comprises a fermentation broth comprising Aureobasidin E and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof as defined above.
  • the component A of the composition according to the invention may further comprise a fermentation broth comprising one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above.
  • the component A may further comprise a fermentation broth comprising one or more other cyclic depsipeptides of formula (la) or stereoisomers thereof as defined above.
  • the component A may further comprise a fermentation broth comprising Aureobasidin G or a stereoisomer thereof.
  • the component A may further comprise a fermentation broth comprising Aureobasidin E or a stereoisomer thereof.
  • the fungicidal compositions according to the invention comprise a component B, wherein the component B comprises thymol.
  • the component B compounds are referred to herein and above by a so-called "ISO common name” or another "common name” being used in individual cases or a trademark name.
  • the component B compounds are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature.
  • the component B according to the invention comprises an active ingredient, preferably wherein the active ingredient comprises a fungicide.
  • the active ingredient comprises a fungicide.
  • thymol is an active ingredient, preferably a fungicide.
  • Thymol also known as 2-isopropyl-5-methylphenol, is registered under CAS 89-83-8.
  • thymol is represented by formula (II):
  • Thymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, anti-inflammatory, antiviral, antibacterial, and antifungal activities, and was formerly used as an anthelmintic medicine.
  • Thymol is one of the main compounds of thyme essential oil, which is typically obtained from Thymus vulgaris L. or Thymus zygis L. Thymol can also be chemically synthesized. For example, thymol can be produced by the alkylation of m-cresol and propene via the following reaction: CH3C6H4OH + CH2CHCH3 —> ((CH3)2CH)CH3CeH3OH. Thymol is commercially available, for example under the brand names THYMOX®, Guarda®, and MEVALONE® (as a mixture of thymol, geraniol, and eugenol).
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin A or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (I) or stereoisomers thereof.
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin A or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (la) or stereoisomers thereof.
  • component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin A or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (la) or stereoisomers thereof.
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin E or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (I) or stereoisomers thereof.
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin E or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (la) or stereoisomers thereof.
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin G or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (I) or stereoisomers thereof.
  • the composition according to the invention comprises the component A of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin G or a stereoisomer thereof, and of from 0.1 % to 90% by weight, preferably of from 0.1 % to 80% by weight, more preferably of from 0.1 % to 60% by weight of the one or more other cyclic depsipeptides represented by formula (la) or stereoisomers thereof.
  • component (A) typically comprises: from 60% to 99.5% by weight of Aureobasidin A, from 0.05% to 5% by weight of Aureobasidin E, optionally, from 0.1 % to 30% by weight of Aureobasidin G, and optionally, from 0.1 % to 10% by weight of one or more other cyclic depsipeptides of formula (la) or stereoisomers thereof.
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1:5000, preferably of from 100:1 to 1:4000, of from 100:1 to 1:3000, of from 100:1 to 1:2000, of from 100:1 to 1:1000, of from 100:1 to 1:800, of from 100:1 to 1:500, of from 100:1 to 1:200, of from 100:1 to 1:100, of from 100:1 to 1:50, of from 100:1 to 1:20, of from 100:1 to 1:10, of from 50:1 to 1:5000, of from 50:1 to 1:4000, of from 50:1 to 1:3000, of from 50:1 to 1:2000, of from 50:1 to 1 :1000, of from 50:1 to 1 :800, of from 50:1 to 1 :500, of from 50:1 to 1 :200, of from 50:1 to 1:100, of from 50:1 to 1:50, of from 50:1 to 1:20,
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1 :1000, of from 100:1 to 1 :800, of from 100:1 to 1:500, of from 100:1 to 1:200, of from 50:1 to 1:800, of from 50:1 to 1:200, of from 50:1 to 1 :100, of from 50:1 to 1 :20, of from 20:1 to 1 :600, of from 20:1 to 1 :40, of from 20:1 to 1 :20, or of from 10:1 to 1:80.
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1 :5000, preferably of from 100:1 to 1 :4000, of from 100:1 to 1:3000, of from 100:1 to 1:2000, of from 100:1 to 1:1000, of from 100:1 to 1:800, of from 100:1 to 1 :500, of from 100:1 to 1 :200, of from 100:1 to 1 :100, of from 100:1 to 1 :50, of from 100:1 to 1 :20, of from 100:1 to 1:10, of from 50:1 to 1 :5000, of from 50:1 to 1 :4000, of from 50:1 to 1 :3000, of from 50:1 to 1 :2000, of from 50:1 to 1 :1000, of from 50:1 to 1 :800, of from 50:1 to 1 :500, of from 50:1 to 1 :200, of from 50:1 to 1 :100, of from 50::1 to
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1:1000, of from 100:1 to 1:800, of from 100:1 to 1 :500, of from 100:1 to 1 :200, of from 50:1 to 1 :800, of from 50:1 to 1 :200, of from 50:1 to 1 :100, of from 50:1 to 1 :20, of from 20:1 to 1 :600, of from 20:1 to 1 :40, of from 20:1 to 1 :20, or of from 10:1 to 1 :80, wherein the component A comprises Aureobasidin A (AbA).
  • AbA Aureobasidin A
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1 :5000, preferably of from 100:1 to 1 :4000, of from 100:1 to 1:3000, of from 100:1 to 1:2000, of from 100:1 to 1:1000, of from 100:1 to 1:800, of from 100:1 to 1 :500, of from 100:1 to 1 :200, of from 100:1 to 1 :100, of from 100:1 to 1 :50, of from 100:1 to 1 :20, of from 100:1 to 1:10, of from 50:1 to 1 :5000, of from 50:1 to 1 :4000, of from 50:1 to 1 :3000, of from 50:1 to 1 :2000, of from 50:1 to 1 :1000, of from 50:1 to 1 :800, of from 50:1 to 1 :500, of from 50:1 to 1 :200, of from 50:1 to 1 :100, of from 50::1 to
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1 :5000, wherein the component A comprises AbA and the component B comprises thymol. More preferably, the weight ratio is of from 100:1 to 1 :2000 or of from 20:1 to 1:500.
  • the composition according to the invention has a weight ratio of the component A to the component B of from 100:1 to 1 :5000, wherein the component A comprises AbA and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1.001 to 1.005 and 1.007 to 1.044 as set forth in Table A, preferably wherein the component A comprises AbA and at least one other cyclic depsipeptide of formula (la) or a stereoisomer thereof selected from the group consisting of AbE and AbG. More preferably, the weight ratio is of from 100:1 to 1 :2000.
  • the composition according to the invention has a weight ratio of the component A to the component B of from 50:1 to 1 :500, wherein the component A comprises AbA and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof selected from the group consisting of compounds 1 .001 to 1 .005 and 1 .007 to 1 .044 as set forth in Table A, preferably wherein the component A comprises AbA and at least one other cyclic depsipeptide of formula (la) or a stereoisomer thereof selected from the group consisting of AbE and AbG. More preferably, the weight ratio is of from 20:1 to 1 :200.
  • the component A of the composition according to the invention is a fermentation broth comprising one or more cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above, and the component B comprises thymol, wherein the weight ratio of the component A to the component B is of from 100:1 to 1 :5000, preferably of from 100:1 to 1 :1000, more preferably from 50:1 to 1 :500, even more preferably from 20:1 to 1 :200.
  • the component A of the composition according to the invention is a fermentation broth comprising AbA and one or more other cyclic depsipeptides of formula (I) or stereoisomers thereof as defined above, and the component B comprises thymol, wherein the weight ratio of the component A to the component B is of from 100:1 to 1 :5000, preferably of from 100:1 to 1 :1000, more preferably from 50:1 to 1 :500, even more preferably from 20:1 to 1 :200.
  • the compounds of formula (I) or stereoisomers thereof according to the invention can be prepared by methods known to the person skilled in the art.
  • the compounds of formula (I) can be either purchased or prepared using synthetic or semi-synthetic chemistry or fermentation processes.
  • the compounds of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof can be prepared by methods known 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 comprising one or more compouds of formula (I) or stereoisomers thereof or formula (la) or stereoisomers thereof can be obtained from a process of fermentation of a strain of Aureobasidium pullulans, generally by a strain of Aureobasidium pullulans R106.
  • the fermentation broth may not require purification.
  • one or more compounds of formula (I) can be isolated from the fermentation broth and purified, e.g.
  • a sorbent e.g., silica and reverse phase silica gels, optically active sorbents, resins
  • solvents e.g., partitioning, counter current separation, mixture of polyphasic solvents
  • other chemical means e.g., crystallization, recrystallizazion, salt formation, and precipitation
  • Purity of the compounds of formula (I) or stereoisomers thereof can include, but is not limited to, a range of from 10% to 20%, or from 20% to 30%, or from 30% to 40%, or from 40% to 50%, or from 50% to 60%, or from 60% to 70%, or from 70% to 80%, or from 80% to 90%, or from 90% to 100%.
  • the purity of the compounds of formula (I) or stereoisomers thereof can be measured by any technique known to the person skilled in the art, including NMR, mass spectrometry, liquid chromatography-mass spectrometry (LCMS), high performance liquid chromathography (HPLC) and other analytical means.
  • NMR nuclear magnetic resonance
  • mass spectrometry mass spectrometry
  • LCMS liquid chromatography-mass spectrometry
  • HPLC high performance liquid chromathography
  • fungicide as used herein means a compound that controls, modifies, or prevents the growth of fungi.
  • fungicidally effective amount means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material denotes all generative parts of a plant, for example seeds or vegetative parts of plants such as cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • composition stands for the various mixtures or combinations of the components A and B (including the above-defined embodiments), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • composition according to the invention is effective against harmful microorganisms, such as microorganisms, that cause phytopathogenic diseases, in particular against phytopathogenic fungi.
  • composition of the invention may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes:
  • Oomycetes 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 diseases such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Peronospora manshurica, Peronospora tabacina, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cub
  • Ascomycetes including blotch, spot, blast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora,
  • Gerlachia nivale Gibberella fujikuroi
  • Gibberella zeae Gibberella zeae
  • Gliocladium spp. Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae;
  • Basidiomycetes including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.
  • Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae
  • rusts for example those caused by Pucciniales such as Cerotelium fici, Chr
  • Puccinia striiformis f.sp. secalis Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi- viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phakopsora meibomiae, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia haperplexans, Corticium invisum, Laetisaria fuciformis, Wait
  • Blastocladiomycetes such as Physoderma maydis
  • Mucoromycetes such as Choanephora cucurbitarum; Mucor spp.; Rhizopus arrhizus, Rhizopus oryzae, Rhizopus stolonifera, Rhizopus nigricans, as well as diseases caused by other species and genera closely related to those listed above.
  • compositions according to the invention are particularly effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Alternaria, Podosphaera, Erysiphe, Magnaporthe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (also known as Deuteromycetes; e.g.
  • Ascomycetes e.g. Venturia, Alternaria, Podosphaera, Erysiphe, Magnaporthe, Monilinia, Mycosphaerella, Uncinula
  • Basidiomycetes e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia
  • Botrytis Colletotrichum, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Penicillium, Pyricularia and Pseudocercosporella); Oomycetes (e.g. Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).
  • compositions according to the invention may be effective against phytopathogenic fungi selected from the group consisting of Alternaria, Ascochyta, Botrytis, Cercospora, Cochliobolus sativus, Colletotrichum, Colletotrichum lagenarium, Corynespora, Erysiphe, Erysiphe cichoracearum, Sphaerotheca fuliginea, Fusarium, Fusarium oxysporum, Gaumannomyces graminis, Guignardia, Helminthosporium, Hemileia vastatrix, Magnaporthe, Magnaporthe oryzae, Monilinia, Mycosphaerella, Mycosphaerella arachidis, Phakopsora, Phoma, Phomopsis, Puccinia, Pseudocercosporella, Pseudopezicula, Phragmidium mucronatum, Podosphaera, Py
  • compositions of the present invention may be particularly effective against phytopathogenic fungi selected from the group consisting of Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Fusarium, Guignardia, Magnaporthe, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Rhizoctonia, Septoria, Uncinula and Venturia, more preferably selected from the group consisting of: Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula and Venturia, preferably selected from the group consisting of: Alternaria, Bot
  • compositions of the present invention may be effective especially against phytopathogenic fungi selected from the group consisting of Alternaria solani, Alternaria alternata, Alternaria porri, Botrytis cinerea, Botrytis aim, Botrytis squamosa, Cercospora capsici, Colletotrichum lagenarium, Corynespora cassiicola, Fusarium oxysporum, Guignardia bidwellii, Magnaporthe oryzae, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Penicillium digitatum, Penicillium italicum, Penicillium expansum, Phomopsis viticola, Podosphaera leucotricha, Podosphaera xanthii, Pseudopezicula tracheiphila, Rhizoctonia solani, Septoria tritici, Uncinula necator and Venturia inaequalis,
  • “useful plants” typically comprise the following perennial or annual plants: grains such as cereals, e.g. barley, maize (corn), millet, oats, rice, rye, sorghum, triticale, tritordeum and wheat, amaranth, buckwheat, chia, quinoa, and canihua; fruits and tree nuts such as grape vine (table and wine grapes), almond, apple, apricot, avocado, banana, blackberry, blueberry, breadfruit, cacao, cashew, cherimoya, cherry, chestnut (for nuts), chokeberry, citrus (including grapefruit, lime, lemon, orange, calamansi), coconut, coffee, cranberry, currant, date, feijoa fruit, fig, filbert (hazelnut), gooseberry, guava, kiwi, litchi, macadamia, mango, nectarine, olive, papaya, passion fruit, peach, pear, pecan, pers
  • crops
  • larch, fir, or pine temperate and tropical hardwoods e.g. oak, birch, beech, teak, or mahogany, and tree species in arid zones, e.g. eucalyptus tree; horticulture crops such as hops, maple (maple syrup), tea, natural rubber plants and turfgrass e.g. bentgrass, kentucky bluegrass, ryegrass, Fescues, bermudagrass, centipede grass, crested hairgrass, kikuyugrass, st.
  • horticulture crops such as hops, maple (maple syrup), tea, natural rubber plants and turfgrass e.g. bentgrass, kentucky bluegrass, ryegrass, Fescues, bermudagrass, centipede grass, crested hairgrass, kikuyugrass, st.
  • the useful plant may be selected from the group consisting of wheat, barley, rice, soybean, apples, almonds, cherries, raspberries, grapes, cucumbers, peanuts, tomatoes, strawberries, citrus and bananas.
  • the useful plant may be selected from the group consisting of: apples, almonds, cherries, raspberries, grapes, cucumbers, peanuts, tomatoes, strawberries, citrus, and bananas.
  • the useful plant may be selected from: fruits and tree nuts, vegetables, horticulture crops, and floriculture.
  • useful plants is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol- pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • ALS inhibitors for example primisulfuron, prosulfuron and trifloxysulfuron
  • EPSPS 5-enol- pyrovyl-shikimate-3-phosphate-synthase
  • GS glutamine synthetase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® , Herculex I® and LibertyLink®.
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria.
  • toxins which can be expressed include 6-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
  • compositions according to the present invention are particularly effective to control or prevent phytopathogenic diseases, especially powdery mildews, rusts, leaf spot, early blights or molds, caused by certain phytopathogenic fungi on grains, fruits and tree nuts, vegetables, field crops, oil seed crops, forage crops, forest plants, horticulture crops, floriculture, greenhouse and nursery plants, propagative materials, culinary herbs and spices, and medicinal herbs, such as: Altemaria solani, preferably on tomatoes.
  • Alternaria alternata preferably on aubergines.
  • Alternaria porri preferably on onions.
  • Botrytis cinerea preferably on tomatoes, peppers, onions, pomes, stone fruits, kiwi, blueberry, sugar beet or grapes.
  • Botrytis aim, preferably on onions.
  • Botrytis squamosa preferably on onions.
  • Cercospora capsici preferably on peppers.
  • Corynespora cassiicola preferably on tomatoes.
  • Guignardia bidwellii preferably on grapes.
  • Monilinia fructicola preferably on cherries, peaches, plums, prunes, nectarines or almonds.
  • Monilinia fructigena preferably on cherries, peaches, plums, prunes, nectarines or almonds.
  • Monilinia laxa preferably on cherries, peaches, plums, prunes, nectarines or almonds.
  • Phomopsis viticola preferably on grapes.
  • Podosphaera leucotricha preferably on apples.
  • Podosphaera xanthii preferably on cucurbits.
  • Pseudopezicula tracheiphila preferably on grapes.
  • Uncinula necator preferably on grapes.
  • Venturia inaequalis preferably on apples.
  • compositions according to the present invention are furthermore particularly effective against seedborne and soilborne diseases, such as Alternaria spp., Ascochyta spp., Botrytis cinerea, Cercospora spp., Claviceps purpurea, Cochliobolus sativus, Colletotrichum spp., Epicoccum spp., Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Fusarium subglutinans, Gaumannomyces graminis, Helminthosporium spp., Microdochium nivale, Phoma spp., Pyrenophora graminea, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia cerealis, Sclerotinia spp., Septoria spp., Sphacelotheca reilliana, T
  • Verticillium spp. in particular against pathogens of cereals, such as wheat, barley, rye or oats; maize; rice; cotton; soybean; turf; sugarbeet; oil seed rape; potatoes; pulse crops, such as peas, lentils or chickpea; and sunflower.
  • compositions according to the present invention are furthermore particularly effective against post harvest diseases such as Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Mucor piriformis, Penicilium italicum, Penicilium solitum, Penicillium digitatum or Penicillium expansum in particular against pathogens of fruits, such as pomefruits, for example apples and pears, stone fruits, for example peaches and plums, citrus, melons, papaya, kiwi, mango, berries, for example strawberries, avocados, pomegranates and bananas, and nuts.
  • post harvest diseases such as Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilinia fructigena,
  • the invention further provides a use of a composition comprising the components A and B as defined according to the invention as a fungicide.
  • the use is non-therapeutic.
  • compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.
  • compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.
  • compositions according to the invention can be applied to the phytopathogenic microorganisms, the useful plants, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.
  • compositions according to the invention may be applied before or after infection of the useful plants, the propagation material thereof, storage goods or technical materials by the microorganisms.
  • the amount of a combination of the invention to be applied will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of fungi to be controlled or the application time.
  • compositions comprising component A in combination with the component B can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • compositions according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application.
  • the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 2000 g a.i./ha of the component B.
  • the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 1500 g a.i./ha, 5 g a.i./ha to 1000 g a.i./ha, 5 g a.i./ha to 500 g a.i./ha, 5 g a.i./ha to 250 g a.i./ha, 5 g a.i./ha to 100 g a.i./ha, 5 g a.i./ha to 50 g a.i./ha, 10 g a.i./ha to 2000 g a.i./ha, 10 g a.i./ha to 1500 g a.i./ha, 10 g a.i./ha to 1000 g a.i./ha, 10 g a.i./ha to 500 g a.i./ha
  • the component A is applied at a rate of from 25 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 2000 g a.i./ha of the component B.
  • the component A is applied at a rate of from 25 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 1500 g a.i./ha, 5 g a.i./ha to 1000 g a.i./ha, 5 g a.i./ha to 500 g a.i./ha, 5 g a.i./ha to 250 g a.i./ha, 5 g a.i./ha to 100 g a.i./ha, 5 g a.i./ha to 50 g a.i./ha, 10 g a.i./ha to 2000 g a.i./ha, 10 g a.i./ha to 1500 g a.i./ha, 10 g a.i./ha to 1000 g a.i./ha, 10 g a.i./ha to 500 g a.i./ha
  • the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 2000 g a.i./ha of the component B, wherein the component A comprises AbA.
  • the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 5 g a.i./ha to 1500 g a.i./ha, 5 g a.i./ha to 1000 g a.i./ha, 5 g a.i./ha to 500 g a.i./ha, 5 g a.i./ha to 250 g a.i./ha, 5 g a.i./ha to 100 g a.i./ha, 5 g a.i./ha to 50 g a.i./ha, 10 g a.i./ha to 2000 g a.i./ha, 10 g a.i./ha to 1500 g a.i./ha, 10 g a.i./ha to 1000 g a.i./ha, 10 g a.i./ha to 500 g a.i./ha
  • the component A when applied to a plant according to the invention, preferably a useful plant, is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 10 g a.i./ha to 2000 g a.i./ha or 20 g a.i/ha to 500 g a.i./ha of the component B.
  • the component A when applied to the plant, preferably the useful plant, is applied at a rate of from 25 g a.i./ha to 500 g a.i./ha in association with 10 g a.i./ha to 2000 g a.i./ha or 20 g a.i/ha to 500 g a.i./ha of the component B.
  • the method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant, preferably a useful plant, or on propagation material thereof comprises applying to the plant, the locus thereof or propagation material thereof, a composition as defined according to the invention, wherein the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 10 g a.i./ha to 2000 g a.i./ha or 20 g a.i/ha to 500 g a.i./ha of the component B.
  • the method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant, preferably a useful plant, or on propagation material thereof comprises applying to the plant, the locus thereof or propagation material thereof, a composition as defined according to the invention, wherein the component A is applied at a rate of from 25 g a.i./ha to 500 g a.i./ha in association with 10 g a.i./ha to 2000 g a.i./ha or 20 g a.i/ha to 500 g a.i./ha of the component B.
  • the component A is applied at a rate of at least 0.001 ppm association with at least 0.01 ppm of the component B.
  • the component A is applied at a rate of at least 0.001 ppm association with at least 0.04 ppm of the component B.
  • the component A is applied at a rate of at least 0.001 ppm association with at least 0.0781 ppm of the component B.
  • the component A is applied at a rate of at least 0.0063 ppm association with at least 0.001 ppm of the component B.
  • the component A is applied at a rate of from 0.001 ppm to 1 ppm in association with 0.01 ppm to 50 ppm of the component B.
  • the component A is applied at a rate of from 0.001 ppm to 1 ppm in association with 0.05 ppm to 10 ppm of the component B.
  • the method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi according to the invention may be particularly effective against phytopathogenic fungi selected from the group consisting of: Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Fusarium, Guignardia, Magnaporthe, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Rhizoctonia, Septoria, Uncinula, and Venturia, more preferably selected from the group consisting of: Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Guignardia, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Septoria, Uncinula and Vent
  • the method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi according to the invention may be effective especially against phytopathogenic fungi selected from the group consisting of: Alternaria solani, Alternaria alternata, Alternaria porri, Botrytis cinerea, Botrytis aim, Botrytis squamosa, Cercospora capsici, Colletotrichum lagenarium, Corynespora cassiicola, Fusarium oxysporum, Guignardia bidwellii, Magnaporthe oryzae, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Penicillium digitatum, Penicillium italicum, Penicillium expansum, Phomopsis viticola, Podosphaera leucotricha, Podosphaera xanthii, Pseudopezicula tracheiphila, Rhizoctonia solani, Septoria tritici,
  • a method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi, preferably phytopathogenic fungi, according to the invention which comprises applying a composition according to the invention to useful plants selected from the group consisting of: fruits and tree nuts, vegetables, horticulture crops, and floriculture.
  • phytopathogenic diseases or phytopathogenic fungi preferably phytopathogenic fungi
  • the invention which comprises applying a composition according to the invention to useful plants selected from the group consisting of wheat, barley, rice, soybean, apples, almonds, cherries, raspberries, grapes, cucumbers, peanuts, tomatoes, strawberries, citrus and bananas.
  • a method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi, preferably phytopathogenic fungi, according to the invention which comprises applying a composition according to the invention to useful plants selected from the group consisting of: apples, almonds, cherries, raspberries, grapes, cucumbers, peanuts, tomatoes, strawberries, citrus, and bananas.
  • a preferred composition according to the invention comprises the component A comprising Aureobasidin A and the component B comprising thymol.
  • the weight ratio of Aureobasidin A to thymol is of from 1 : 1.24 to 1 : 124.
  • the weight ratio of Aureobasidin A to thymol is of from 1 : 6.2 to 1 : 18.6.
  • the weight ratio of Aureobasidin A to thymol is of from 1 : 11 .2 to 1 : 13.6.
  • the weight ratio of Aureobasidin A to thymol is about 1 : about 12.4, preferably 1 : 12.4.
  • a preferred method according to the invention comprises a method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant or on propagation material thereof, the method comprising applying to the plant, locus thereof, or propagation material thereof, a composition according to the invention, wherein the component A comprises Aureobasidin A and the component B comprises thymol.
  • Aureobasidin A is applied at a rate of from 0.003 ppm to 0.0125 ppm in association with 0.0391 ppm to 0.1562 ppm of thymol.
  • Aureobasidin A is applied at a rate of from 0.0063 ppm to 0.05 ppmin association with 0.0781 ppm to 1 .25 ppm of thymol.
  • Aureobasidin A is applied at a rate of from 0.0063 ppm to 0.025 ppm in association with 0.00781 ppm to 0.6248 ppm of thymol.
  • Aureobasidin A is applied at a rate of about 0.0063 ppm in association with about 0.0781 ppm of thymol.
  • the phytopathogenic fungi is Botrytis cinerea.
  • the composition according to the invention comprises an agriculturally acceptable carrier and/or formulation adjuvant, and optionally, a surfactant.
  • the invention also provides fungicidal compositions comprising a combination of the components A and B as mentioned above in a synergistically effective amount, together with an agriculturally acceptable carrier and, optionally, a surfactant.
  • the weight ratio of the component A to the component B is preferably from 100:1 to 1 :5000, more preferably from 100:1 to 1 :1000, even more preferably from 50:1 to 1 :500, still more preferably from 20:1 to 1 :200 as described hereinbefore.
  • compositions wherein the component A and the component B are present in the composition in amounts producing a synergistic effect.
  • This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising the component A and the component B is greater than the sum of the fungicidal activities of the component A and the component B.
  • This synergistic activity extends the range of action of the component A and the component B in two ways.
  • X % action by active ingredient (A) using p ppm of active ingredient
  • Y % action by active ingredient (B) using q ppm of active ingredient.
  • synergism corresponds to a positive value for the difference of (O-E).
  • expected activity said difference (O-E) is zero.
  • a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
  • compositions according to the invention can also have further surprising advantageous properties.
  • advantageous properties are: more advantageuos degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination.
  • the composition according to the invention is preferably in a synergistically effective amount.
  • the component A and the component B of the composition according to the invention are each in an amount which results in in a synergistic effect, preferably a synergistic fungicidal effect.
  • the composition according to the invention has a weight ratio of the component A and the component B in a synergistically effective amount.
  • thymol advantageously provides more than an additive fungicidal effect when combined with a cyclic depsipeptide represented by formula (I), in particular AbA.
  • formula (I) cyclic depsipeptide represented by formula (I)
  • compositions according to the invention are tested fortheir biological (fungicidal) activity as dimethylsulfoxide (DMSO) solutions using one or more of the following protocols (Example 1-1).
  • DMSO dimethylsulfoxide
  • Aureobasidin A and its synthesis are known from Takesako et al., The Journal of Antibiotics, 1991 , 44, 919-924.
  • Aureobasidin A is separated from the fermentation broth by extraction with ethyl acetate, followed by extraction of the ethyl acetate concentrate with a mixture of MeOH:H2O (80% by volume) and cyclohexane (20% by volume), and purified by silica gel column chromatography (silica- gel, elution with hexane:ethyl acetate) followed by reverse phase column chromatography (RP18, elution with acetonitrile:H20).
  • thymol is known and commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature.
  • Example 1-1 Botrytis cinerea (Botryotinia fuckeliana gray mould)
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogel’s). After placing a (DMSO) solution or (water) suspension of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically and visually after 72 hrs.
  • Table 1 Fungicidal activity of a composition of Aureobasidin A and thymol against Botrytis cinerea as described in Example 1-1 above.
  • Embodiment 1 A fungicidal composition comprising:
  • a component A wherein the component A comprises a cyclic depsipeptide, wherein the cyclic depsipeptide is Aureobasidin A (AbA) or a stereoisomer thereof, preferably wherein AbA is represented by formula (lb):
  • Embodiment 2 The composition of embodiment 1 , wherein the component A additionally comprises one or more other cyclic depsipeptides represented by formula (I) or a stereoisomer thereof: wherein:
  • R 1 is methyl or ethyl
  • R 2 is methyl, hydroxymethyl, or hydroxyethyl
  • R 3 is hydrogen or methyl
  • each of X 1 , X 2 , and X 3 is hydrogen, or X 1 , X 2 , and X 3 are hydrogen, fluorine, or hydroxyl, with the proviso that only one of X 1 , X 2 , and X 3 is fluorine or hydroxyl;
  • X 4 is CH2, S, or hydroxymethylene;
  • a 3 is an a-amino acid residue selected from: N-methyl-L-phenylalanine (L-MePhe), L- phenylalanine (L-Phe), p-hydroxy-N-methyl-L-phenylalanine (L-p-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), para-bromo-N-methyl-L-phenylalanine (L-p-Br-MePhe), meta-iodo-N-methyl-L-phen
  • a 5 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), L- norleucine (L-Nle), L-norvaline (L-Nva), L-valine (L-Val), and L-methioninesulfoxide (L-Met(O)) residues;
  • a 6 is an a-amino acid residue selected from: N-methyl-L-valine (L-MeVal), N-methyl-L-leucine (L-MeLeu), N-methyl-L-allo-isoleucine (L-MeAlle), and L-valine (L-Val) residues;
  • a 7 is an a-amino acid residue selected from: L-allo-isoleucine (L-Alle), L-leucine (L-Leu), and L-norvaline (L-Nva) residues; and
  • a 8 is an a-amino acid residue selected from: p-methyl-L-phenylalanine (L-p-Phe), p-hydroxy- N-methyl-L-valine (L-p-OH-MeVal), y-hydroxy-N-methyl-L-valine (L-y-OH-MeVal), N-methyl-L-valine (L-MeVal), L-valine (L-Val), N-methyl-2,3-didehydro-L-valine (L-MeDFL.sVal), N-methyl-3,4-didehydro- L-valine (L-MeDHs.A/al), N-methyl-L-phenylalanine (L-MePhe), p-hydroxy-N-methyl-L-phenylalanine (L-p-OH-MePhe), N-methyl-L-threonine (L-MeThr), sarcosine (Sar), and N,p-dimethyl-L-aspartic acid (L
  • Embodiment 3 The composition of embodiment 1 or 2, wherein the component A further comprises at least one other cyclic depsipeptide of formula (I) or a stereoisomer thereof selected from the group consisting of Aureobasidin E (AbE) and Aureobasidin G (AbG), preferably wherein AbE is represented by formula (Ic):
  • AbG is represented by formula (Id):
  • Embodiment 4 The composition of embodiment 2 or 3, wherein the component A comprises of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin A or a stereoisomer thereof, and of from 0.1% to 90% by weight, preferably of from 0.1% to 80% by weight, more preferably of from 0.1% to 60% by weight of the one or more other cyclic depsipeptides represented by formula (I) or stereoisomers thereof.
  • the component A comprises of from 10% to 99.9% by weight, preferably of from 20% to 99.9% by weight, more preferably of from 40% to 99.9% by weight of Aureobasidin A or a stereoisomer thereof, and of from 0.1% to 90% by weight, preferably of from 0.1% to 80% by weight, more preferably of from 0.1% to 60% by weight of the one or more other cyclic depsipeptides represented by formula (I) or stereoisomers thereof.
  • Embodiment 5 The composition of any one of embodiments 1 to 4, wherein the weight ratio of the component A to the component B is of from 100:1 to 1 :5000.
  • Embodiment 6 The composition of any one of embodiments 1 to 5, further comprising an agriculturally acceptable carrier and/or formulation adjuvant, and optionally, a surfactant.
  • Embodiment 7 A method of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on a plant or on propagation material thereof, the method comprising applying to the plant, locus thereof, or propagation material thereof, a composition of any one of embodiments 1 to 6.
  • Embodiment 8 The method of embodiment 7, wherein the component A is applied at a rate of from 10 g a.i./ha to 500 g a.i./ha in association with 10 g a.i./ha to 1000 g a.i./ha of the component B.
  • Embodiment 9 The method of embodiment 7 or 8, wherein the phytopathogenic fungi are selected from the group consisting of: Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Fusarium, Guignardia, Magnaporthe, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicula, Rhizoctonia, Septoria, Uncinula, and Venturia, preferably Botrytis.
  • the phytopathogenic fungi are selected from the group consisting of: Alternaria, Botrytis, Cercospora, Colletotrichum, Corynespora, Fusarium, Guignardia, Magnaporthe, Mycosphaerella, Monilinia, Penicillium, Phakopsora, Phomopsis, Podosphaera, Pseudopezicul
  • Embodiment 10 The method of any one of embodiments 7 to 9, wherein the plant is a useful plant selected from: grains, fruits and tree nuts, vegetables, field crops, oil seed crops, forage crops, forest plants, horticulture crops, floriculture, greenhouse and nursery plants, propagative materials, culinary herbs and spices, and medicinal herbs, preferably wherein the useful plant is selected from: fruits and tree nuts, vegetables, horticulture crops, and floriculture.
  • the plant is a useful plant selected from: grains, fruits and tree nuts, vegetables, field crops, oil seed crops, forage crops, forest plants, horticulture crops, floriculture, greenhouse and nursery plants, propagative materials, culinary herbs and spices, and medicinal herbs, preferably wherein the useful plant is selected from: fruits and tree nuts, vegetables, horticulture crops, and floriculture.
  • Embodiment 11 The method of any one of embodiments 7 to 10, wherein the plant is a useful plant selected from the group consisting of: apples, almonds, cherries, raspberries, grapes, cucumbers, peanuts, tomatoes, strawberries, citrus, and bananas.
  • Embodiment 12 Use of the composition comprising the components A and B of any one of embodiments 1 to 6 as a fungicide.

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Abstract

L'invention concerne une composition fongicide comprenant un composant A comprenant un depsipeptide cyclique auréobasidine A ou un stéréoisomère de celui-ci, et un composant B comprenant du thymol. L'invention concerne un procédé pour lutter contre ou prévenir des maladies phytopathogènes ou de champignons phytopathogènes sur une plante ou sur un matériau de propagation de celle-ci, le procédé comprenant l'application de la composition sur la plante, son locus ou son matériau de propagation. L'invention concerne également l'utilisation de la composition en tant que fongicide.
PCT/EP2024/072163 2023-08-08 2024-08-05 Compositions fongicides Pending WO2025032053A1 (fr)

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Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0352092A2 (fr) 1988-07-19 1990-01-24 Takara Shuzo Co. Ltd. Antibiotique R106
EP0500264A1 (fr) 1991-02-19 1992-08-26 Takara Shuzo Co. Ltd. Fongicides agricoles et horticoles
WO2018102345A1 (fr) 2016-11-30 2018-06-07 Agrobiologics Llc Utilisation de l'auréobasidine antifongique en agriculture
US10820597B2 (en) * 2011-03-18 2020-11-03 Biofungitek, S.L. Phytosanitary composition comprising essential oils that potentiate antifungal activity
WO2021245100A1 (fr) * 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245105A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245104A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245102A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245103A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245106A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2022140638A1 (fr) * 2020-12-22 2022-06-30 Agrospheres, Inc. Compositions et procédés d'élimination de champignons
WO2023089007A1 (fr) * 2021-11-19 2023-05-25 Syngenta Crop Protection Ag Compositions fongicides

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0352092A2 (fr) 1988-07-19 1990-01-24 Takara Shuzo Co. Ltd. Antibiotique R106
EP0500264A1 (fr) 1991-02-19 1992-08-26 Takara Shuzo Co. Ltd. Fongicides agricoles et horticoles
US10820597B2 (en) * 2011-03-18 2020-11-03 Biofungitek, S.L. Phytosanitary composition comprising essential oils that potentiate antifungal activity
WO2018102345A1 (fr) 2016-11-30 2018-06-07 Agrobiologics Llc Utilisation de l'auréobasidine antifongique en agriculture
WO2021245100A1 (fr) * 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245105A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245104A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245102A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245103A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245106A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2022140638A1 (fr) * 2020-12-22 2022-06-30 Agrospheres, Inc. Compositions et procédés d'élimination de champignons
WO2023089007A1 (fr) * 2021-11-19 2023-05-25 Syngenta Crop Protection Ag Compositions fongicides

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
AWAZU ET AL., J. ANTIBIOT., vol. 48, 1995, pages 525 - 527
COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combination", WEEDS, vol. 15, 1967, pages 20 - 22, XP001112961
HOU HUIYU ET AL: "Effects of Origanum vulgare essential oil and its two main components, carvacrol and thymol, on the plant pathogen Botrytis cinerea", vol. 8, 14 August 2020 (2020-08-14), pages e9626, XP093118236, ISSN: 2167-8359, Retrieved from the Internet <URL:https://peerj.com/articles/9626.html> DOI: 10.7717/peerj.9626 *
MAHARANI ET AL., TETRAHEDRON, vol. 70, 2014, pages 2351 - 2358
TAKESAKO ET AL., J. ANTIBIOT, vol. 44, 1991, pages 919 - 924
TAKESAKO ET AL., TETRAHEDRON, vol. 52, 1996, pages 4327 - 4346
TAKESAKO ET AL., THE JOURNAL OF ANTIBIOTICS, vol. 44, no. 89-83-8, 1991, pages 919 - 924
YANG KANG ET AL: "Mechanism of thymol inhibiting Botrytis cinerea: PAO-H2O2 system", CHINESE JOURNAL OF APPLIED ECOLOGY., 1 July 2020 (2020-07-01), China, pages 2441 - 2448, XP093118249, Retrieved from the Internet <URL:https://kns.cnki.net/kcms/detail/detail.aspx?doi=10.13287/j.1001-9332.202007.031> [retrieved on 20240111], DOI: 10.13287/j.1001-9332.202007.031 *
YOSHIKAWA ET AL., J. ANTIBIOT., vol. 46, 1993, pages 1347 - 1354

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