Search

CN-122028793-A - Fungicidal compositions

CN122028793ACN 122028793 ACN122028793 ACN 122028793ACN-122028793-A

Abstract

A fungicidal composition comprising a component A comprising the cyclic depsipeptide aureobasidin A or a stereoisomer thereof, and a component B comprising the bacterial Bacillus amyloliquefaciens. A method of controlling or preventing a phytopathogenic disease or phytopathogenic fungus on a plant or on propagation material thereof, the method comprising applying the composition to the plant, to a locus thereof or to propagation material thereof. The use of the composition as a fungicide.

Inventors

  • WOLF HANNO CHRISTIAN
  • O. Roseller

Assignees

  • 先正达农作物保护股份公司

Dates

Publication Date
20260512
Application Date
20240805
Priority Date
20230808

Claims (13)

  1. 1. A fungicidal composition, which comprises a substrate and a substrate, the fungicidal composition comprises: (i) Component A, wherein said component A comprises a cyclic depsipeptide, wherein said cyclic depsipeptide is aureobasidin A (AbA) or a stereoisomer thereof, and (Ii) Component B, wherein the component B comprises a bacterial bacillus amyloliquefaciens.
  2. 2. The composition of claim 1, wherein component a additionally comprises one or more other cyclic depeptides represented by formula (I): (I), Wherein: r 1 is methyl or ethyl; R 2 is methyl, hydroxymethyl or hydroxyethyl; R 3 is hydrogen or methyl; X 1 、X 2 and X 3 are each hydrogen, or X 1 、X 2 and X 3 are hydrogen, fluorine or hydroxy, provided that only one of X 1 、X 2 and X 3 is fluorine or hydroxy; X 4 is CH 2 , S or hydroxymethylene; A 3 is an alpha-amino acid residue selected from the group consisting of N-methyl-L-phenylalanine (L-MePhe), L-phenylalanine (L-Phe), beta-hydroxy-N-methyl-L-phenylalanine (L-beta-OH-MePhe), o-fluoro-N-methyl-L-phenylalanine (L-o-F-MePhe), m-fluoro-N-methyl-L-phenylalanine (L-m-F-MePhe), p-fluoro-N-methyl-L-phenylalanine (L-p-F-MePhe), m-bromo-N-methyl-L-phenylalanine (L-m-Br-MePhe), p-bromo-N-methyl-L-phenylalanine (L-p-Br-MePhe), m-iodo-N-methyl-L-phenylalanine (L-m-I-MePhe), p-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-pyridyl) -N-methyl-L-phenylalanine, 4- (4-pyridinyl) -N-methyl-L-phenylalanine, 3- (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 ] -N-methyl-L-phenylalanine, 4- [4- (piperazin-1-yl) phenyl ] -N-methyl-L-phenylalanine, 3- [4- (4-methylpiperazin-1-yl) phenyl ] -N-methyl-L-phenylalanine, 4- [4- (4-methylpiperazin-1-yl) phenyl ] -N-methyl-L-phenylalanine, beta-oxo-N-methyl-L-phenylalanine (L-beta-oxo-MePhe), beta-R 4 O-N-methyl-L-phenylalanine (wherein R 4 is a lower acyl group having 1 to 4 carbon atoms) (L-beta-R 3 OMePhe), N-methyl-L-tyrosine (L-MeTyr), O-methyl-N-methyl-L-tyrosine [ L-MeTyr (Me) ], N-methyl-L-alanine (L-MeAla), N-methyl-L-serine (L-MeSer), sarcosine (Sar), N-methyl-D-phenylalanine (D-MePhe), N-methyl-D-alanine (D-MeAla), N-methyl-D-valine (D-MeVal), and N-methyl-D-serine (D-MeSer) residues; A 5 is an alpha-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), L-valine (L-Val) and L-methionine sulfoxide (L-Met (O)); A 6 is an alpha-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 alpha-amino acid residue selected from the group consisting of L-allo-isoleucine (L-AIle), L-leucine (L-Leu) and L-norvaline (L-Nva) residues, and A 8 is an alpha-amino acid residue selected from the group consisting of beta-methyl-L-phenylalanine (L-beta-Phe), beta-hydroxy-N-methyl-L-valine (L-beta-OH-MeVal), gamma-hydroxy-N-methyl-L-valine (L-gamma-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 Val), N-methyl-L-phenylalanine (L-MePhe), beta-hydroxy-N-methyl-L-phenylalanine (L-beta-OH-MePhe), N-methyl-L-threonine (L-MeThr), sarcosine (Sar), and N, beta-dimethyl-L-aspartic acid (L-N, beta-MeAsp).
  3. 3. Composition according to claim 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): (Ic) and Preferably AbG is represented by formula (Id): (Id)。
  4. 4. a composition according to any one of claims 1 to 3, wherein the bacterium is bacillus amyloliquefaciens strain FZB24 or a functional variant thereof, or bacillus bailii strain FZB24 or a functional variant thereof.
  5. 5. Composition according to any one of claims 2 to 4, wherein the component a comprises from 10% to 99.9% by weight, preferably from 20% to 99.9% by weight, more preferably from 40% to 99.9% by weight of aureobasidin a or a stereoisomer thereof and from 0.1% to 90% by weight, preferably from 0.1% to 80% by weight, more preferably from 0.1% to 60% by weight of the one or more other cyclic ester peptides represented by formula (I) or stereoisomers thereof.
  6. 6. The composition according to any one of claims 1 to 5, wherein the weight ratio of component a to component B is 100:1 to 1:5000.
  7. 7. The composition according to any one of claims 1 to 6, further comprising an agriculturally acceptable carrier and/or formulation aid and optionally a surfactant.
  8. 8. A method of controlling or preventing a phytopathogenic disease or phytopathogenic fungus on a plant or on propagation material thereof, the method comprising applying the composition according to any one of claims 1 to 7 to the plant, to a locus thereof or to propagation material thereof.
  9. 9. The method of claim 8, wherein the component a is applied in combination with the component B of 10 g a.i./ha to 1000 g a.i./ha at a ratio of 10 g a.i./ha to 500 g a.i./ha.
  10. 10. The method according to claim 8 or 9, wherein the phytopathogenic fungi are selected from the group consisting of: alternaria, botrytis, cercospora, anthrax, clavularia, fusarium, thermomyces, geotrichum, strychophus, sclerotinia, penicillium, leptosphaeria, phomopsis, leptosphaeria, pseudocercospora, rhizoctonia, septoria, leptosphaeria and Ceratosphaeria, preferably selected from the group consisting of: preferably selected from the group consisting of the group consisting of.
  11. 11. The method according to any one of claims 8 to 10, wherein the plant is a useful plant selected from the group consisting of cereals, fruits and tree nuts, vegetables, field crops, oil crops, feed crops, forest plants, horticultural crops, floral horticulture, greenhouse and nursery plants, propagation material, boiled herbs and spices and herbs, preferably wherein the useful plant is selected from the group consisting of fruits and tree nuts, vegetables, horticultural crops and floral horticulture.
  12. 12. The method according to any one of claims 8 to 11, wherein the plant is a useful plant selected from the group consisting of apple, apricot, cherry, raspberry, grape, cucumber, peanut, tomato, strawberry, citrus and banana.
  13. 13. Use of a composition comprising the components a and B according to any one of claims 1 to 7 as fungicide.

Description

Fungicidal compositions The present invention relates to novel fungicidal compositions for controlling fungi. Also disclosed are methods of controlling or preventing phytopathogenic diseases or phytopathogenic fungi on plants or their propagation material. Background Aureobasidin is a group of antifungal cyclic ester peptides isolated for the first time from the filamentous fungus Aureobasidium pullulans (Aureobasidium pullulans) R106 (EP 352092 A2;Takesako et al, 1991, J. Antiboot. J. Antibiotics 44, 919-924, doi 10.7164/antiskitics 44.919; yoshikawa et al, 1993, J. Antiboot. J. Antibiotics 46, 1347-1354, doi 10.7164/antiskitics 46.1347; and Awazu et al, 1995, J. Antiboot. J. Antibiotics 48, 525-527, doi 10.7164/antiskitics 48.525). Aureobasidin exhibits broad spectrum antifungal activity. Furthermore, aureobasidin is disclosed for controlling a variety of phytopathogenic fungi on plants and seeds (EP 0500264 A1, WO 2018102345). Combinations of aureobasidin with one or more other active ingredients having different modes of action for controlling phytopathogenic fungi have also been disclosed (WO 2021245102 A1, WO 2021245103 A1, WO 2021245104 A1, WO 2021245105 A1, WO 2021245106 A1). However, the above fungicides and combinations are not necessarily effective enough and there is a risk of developing resistance. Thus, there remains a need for improved antifungal compositions for controlling phytopathogenic fungi. Disclosure of Invention 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 bacterial bacillus amyloliquefaciens (Bacillus amyloliquefaciens) and/or compounds produced therefrom. According to another aspect of the present invention there is provided a method of controlling or preventing a phytopathogenic disease or phytopathogenic fungus on a plant or on propagation material thereof, the method comprising applying to the plant, its locus or propagation material a composition as defined according to the invention. Preferably, the method comprises applying the composition according to the invention to a plant or locus thereof, more preferably to a plant. Preferably, the method comprises applying the composition according to the invention to propagation material of the plant. According to another aspect of the present invention there is provided the use of a composition comprising components a and B as defined according to the present invention as a fungicide. It has been found that the use of a combination of the bacteria of component B and/or the compounds produced therefrom with the compound of component a having formula (I), which preferably comprises aureobasidin a, surprisingly and significantly enhances the effectiveness of the latter against fungi and vice versa. In addition, the use of the compositions of the present invention is effective against a broader spectrum of such fungi than would be possible if the active ingredients were used alone. The benefits provided by the specific fungicidal compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants from diseases caused by fungi or advantageous properties for use as agrochemical active ingredients (e.g. greater biological activity, advantageous activity profile, increased safety, improved physico-chemical properties or increased biodegradability). As used herein, a residue of a chemical species refers to a derivative of a moiety present in a particular product. To form the product, at least one atom of the moiety is replaced with a bond to the second moiety, such that the product contains a derivative of the moiety. For example, an amino acid residue in a product may refer to a cyclic peptide described herein having an amino acid incorporated therein by formation of one or more peptide bonds, and such residues may be interchangeably referred to herein as amino acids or amino acid residues. As used herein, the term "cyclic ester peptide" refers to a cyclic peptide consisting of units derived from 2-hydroxy-3-methylalkanoic acid or 2-hydroxy-3-hydroxymethylalkanoic acid and units derived from a first a-amino acid residue selected from the group consisting of N-methyl-L-valine (L-MeVal) and L-valine (L-Val) and a second a-amino acid residue selected from the group consisting of L-phenylalanine (L-Phe), o-fluoro-N-methyl-L-phenylalanine (L-o-F-MePhe), m-fluoro-N-methyl-L-phenylalanine (L-m-F-MePhe), para-fluoro-N-methyl-L-phenylalanine (L-p-F-MePhe), 2-hydroxy-phenylalanine (L-2 OH-Phe), 3-hydroxy-phenylalanine (L-3 OH-Phe) and L-tyrosine (L-Tyr), a third alpha-amino acid residue A 3, a fourth alpha-amino acid residue selected from the group consisting of L-proline (L-Pro), L-thioproline (L-SPro) and 4-hydroxy-L-proline (L-4 Hyp), a fifth alpha-amino acid residue A 5, a sixth alpha-amino acid residue A 6, a seventh alpha-amino a