Antifungal composition

Abstract

A composition suitable for controlling a disease caused by a plant pathogen, comprising: (A) a compound of formula I [Formula 1] TIFF2024529110000029.tif4797 (in the formula, R 1 is hydrogen or C1-C3 alkylC(=O)-, R 2 is halogen or C1-C3 alkoxyC(=O)-, and R 3 is C1-C3 haloalkyl or C1-C3 haloalkoxy. and (B) at least one compound selected from compounds known for their fungicidal activity, as well as a method for controlling diseases, in particular leaf spot, powdery mildew and blight, on useful plants.

Description

[Technical field]

[0001] The present invention relates to novel fungicidal compositions suitable for controlling diseases caused by plant pathogens, in particular phytopathogenic fungi, and to methods for controlling diseases on useful plants, in particular fruit and vegetables. [Background technology]

[0002] From WO 2016 / 182021 and WO 2020 / 091031, it is known that certain 2-ethylsulfonyl-benzamide derivatives and mixtures containing said 2-ethylsulfonyl-benzamide derivatives have biological activity against phytopathogenic fungi. On the other hand, various fungicidal compounds of different chemical classes are widely known as plant fungicides for application in various crops of cultivated plants. However, the crop tolerance and activity against phytopathogenic plant fungi do not always meet the demands of agricultural practice in many cases and aspects. In particular, pathogens causing leaf spot diseases such as Pyrenophora teres, the pathogen of net blotch disease in barley, as well as pathogens of powdery mildew such as Uncinula necator, pathogens of grape powdery mildew and fungal blight such as Alternaria solani, and pathogens of early blight diseases in various crops are becoming more and more important problems in crop production, causing considerable yield losses. Many common fungicides are not suitable for controlling leaf spot diseases, powdery mildew and fungal blight, or their action against species such as Pyrenophora teres, Uncinula necator and Alternaria solani is unsatisfactory. Summary of the Invention [Means for solving the problem]

[0003] Therefore, in view of the above-mentioned demands of agricultural practice for increased crop tolerance and / or increased activity against phytopathogenic fungi, such as leaf spot, powdery mildew and blight diseases, the present invention provides novel compositions suitable for controlling diseases caused by phytopathogens, comprising: (A) Formula I [ka] (In the formula, R 1 is hydrogen or C 1 ~C 3 alkylC(=O)-, R 2 is halogen or C 1 ~C 3 AlkoxyC(=O)-, and R 3 is C 1 ~C 3 Haloalkyl or C 1 ~C 3 haloalkoxy) and (B) at least one compound selected from the group consisting of cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboctylamine; A novel composition is proposed comprising: DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0004] When an asymmetric carbon atom is present in the compound of formula I, the compound may occur in the form of optical isomers, i.e., enantiomeric or diastereomeric forms. Conformational isomers may also exist as a result of restricted rotation around a single bond. The present invention encompasses all such possible isomeric forms of the compound of formula I and mixtures thereof. Similarly, formula I is intended to include all possible tautomers. The present invention encompasses all possible tautomeric forms of the compound of formula I and racemates, i.e., mixtures of at least two enantiomers in a substantially 50:50 ratio.

[0005] In each case, the compounds of formula I according to the invention are in free form, in an oxidized form, such as an N-oxide, or in the form of a salt, such as an agriculturally usable salt.

[0006] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds. They are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0007] A preferred composition is (A) Formula I [ka] (In the formula, R 1 is hydrogen or acetyl, R 2 is chloro, bromo or methoxycarbonyl, and R 3 is trifluoromethyl or trifluoromethoxy) and (B) at least one compound selected from the group consisting of cyclobutrifluram, cymoxanil, flufenoxadiazamun, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide, and pydiflumetofen; It includes.

[0008] It has been found that the use of component (B) in combination with component (A) surprisingly and significantly increases the effectiveness against the latter fungi, and vice versa. Furthermore, the method of the present invention is effective against a broader spectrum of such fungi than can be inhibited by the active ingredients of the method when used alone in isolation.

[0009] A further aspect of the present invention is a method for controlling diseases caused by plant pathogens on a useful plant or on its propagation material, comprising applying a composition according to the present invention to the useful plant, its locus or its propagation material. A method comprising applying a composition according to the present invention to a useful plant or its locus, more preferably to a useful plant, is preferred. A method comprising applying a composition according to the present invention to the propagation material of a useful plant is further preferred. The present invention covers all stereoisomers and mixtures thereof in all ratios.

[0010] A preferred embodiment of the present invention comprises, as component A), a compound of formula (I), 1 is acetyl, and R 3 is trifluoromethoxy, and most preferably R 1 is acetyl, R 2 is methoxycarbonyl, and R 3 is trifluoromethoxy or R 1 is acetyl, R 2 is bromo, and R 3 is trifluoromethoxy.

[0011] Preferred compounds of formula (I) are Structure Ia: [ka] Methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate (compound A-1.1) by Structure Ib: [ka] N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide (compound A-1.2) by It is.

[0012] A further preferred embodiment of the present invention is represented by a composition comprising as component B) a fungicide selected from cyclobutrifluram, cymoxanil, flufenoxadiazamun, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide and pydiflumetofen.

[0013] Particularly preferred compositions according to the invention comprise, as component (A), a compound selected from methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate (compound A-1.1) and N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide (compound A-1.2), and, as component (B), a compound selected from cyclobutrifluram, cymoxanil, flufenoxadiazamun, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide and pydiflumetofen.

[0014] Compound A-1.1 can be advantageously prepared in a similar manner as outlined in WO 2016 / 182021.

[0015] Compound A-1.2 can be advantageously prepared in a similar manner as outlined in JP 2017 / 226638.

[0016] Component (B) is well known and is referred to above by the so-called "ISO common name" or another "common name" or trade name used in particular cases.

[0017] The following preferred ingredients (B) are included in the Pesticide Manual Online by the British Crop Production Council ("E-pesticide Manual") and in the Compendium of Pesticide Common Names by Alan Wood: cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and seboctylamine.

[0018] Examples of compounds which are particularly suitable as component (B) are the compounds selected from group P below: cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine.

[0019] Throughout this specification, the expression "composition" refers to various mixtures or combinations of components (A) and (B), for example in a single "ready-mix" form, combination spray mixtures consisting of separate formulations of a single active ingredient component such as a "tank mix", and combined use of a single active ingredient when applied sequentially, i.e., one after the other over a reasonably short period of time such as a few hours or days. The order in which components (A) and (B) are applied is not essential to the practice of the invention.

[0020] Further examples of compositions according to the invention comprising three active ingredients are defined as embodiments E1 and E2.

[0021] Preferred embodiment E1: The term "TX1" as used herein means "compound A-1.1 + a compound selected from group P". Preferred examples include the following compositions: cyclobutrifluram + TX1, cymoxanil + TX1, fulveneteram + TX1, flufenoxadiazam + TX1, flumethylsulfolim + TX1, fluoxythioconazole + TX1, isotianil + TX1, methallylpicoxamide + TX1, pydiflumetofen + TX1, pyrimorph + TX1, pyriophenone + TX1, seboctylamin + TX1.

[0022] Preferred embodiment E2: The term "TX2" means "compound A-1.2 + a compound selected from group P". Preferred examples include the following compositions: cyclobutrifluram + TX2, cymoxanil + TX2, fulveneteram + TX2, flufenoxadiazam + TX2, flumethylsulfolim + TX2, fluoxythioconazole + TX2, isotianil + TX2, methallylpicoxamide + TX2, pydiflumetofen + TX2, pyrimorph + TX2, pyriophenone + TX2, sevoctylamin + TX2.

[0023] The embodiments E1 and E2 define compositions according to the invention comprising three active ingredients. In said embodiments, the mixing partner selected from group P must be different from the other mixing partners described. For example, the composition "cyclobutrifluram+TX1" means a composition comprising as active ingredients benzothiostrobin, compound A-1.1+a compound selected from group P. In said composition, the compound selected from group P is different from cyclobutrifluram.

[0024] The following compositions are preferred: A composition comprising (A) compound A-1.1 and (B) a compound selected from group P. An example of such a composition is a composition comprising compound A-1.1 and a first compound from group P, which is cyclobutrifluram.

[0025] Thus, particularly preferred compositions include those comprising as active ingredients (i) cyclobutrifluram, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and a compound selected from cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and seboctylamine. Further preferred compositions comprise, as active ingredients, (ii) cymoxanil, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and a compound selected from cyclobutrifluram, fluvenetram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and seboxylamine, or (iii) fluvenetram, methyl 2-[acetyl-[2-ethylsulfonyl-4-trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and cyclobutrifluram, cymoxanil, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and seboxylamine. or (iv) a compound selected from flufenoxadiazam, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, cyclobutrifluram, cymoxanil, fulvenetram, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamin, or (v) a compound selected from flufenoxadiazam, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, cyclobutrifluram, cymoxanil, fulvenetram, flufenoxadiazam, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamin, oror (vi) a compound selected from fluoxythioconazole, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, isotianil, methallylpicoxamide, pydiflumetofen, pirimorph, pyriophenone, and sevoctylamine. or (vii) a compound selected from isotianil, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and sebocthylamine, or (viii) a compound selected from methallylpicoxamide, methyl 2-[acetyl-[2-ethylsulfonyl-4- (iii) a compound selected from cyclobutrifluram, cymoxanil, fluvenetram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone and seboctylamine, or (iv) a compound selected from pydiflumetofen, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and cyclobutrifluram, cymoxanil, fluvenetram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone and seboctylamine, or (v) a compound selected from pydiflumetofen, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and cyclobutrifluram, cymoxanil, fluvenetram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone and seboctylamine, a compound selected from fluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pyrimorph, pyriophenone and seboxtylamine, or (x) pyrimorph, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate and cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole,a compound selected from isotianil, methallyl picoxamide, pydiflumetofen, pyriophenone and sebocthylamine, or (xi) pyriophenone, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallyl picoxamide, pydiflumetofen, (xii) a compound selected from sevoctylamine, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pirimorph, and pyriophenone.

[0026] Particularly preferred compositions include, as an active ingredient, (xiii) cyclobutrifluram, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboctylamine, or (xiv) cymoxanil, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cymoxanil, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboctylamine. (xv) a compound selected from fluveneteram, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, cyclobutrifluram, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine, or (xvi) a compound selected from fluveneteram, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, (xvi) flufenoxadiazam, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide and a compound selected from cyclobutrifluram, cymoxanil, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine, or (xvi) flufenoxadiazam, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide and cyclobutrifluram, cymoxanil, fulveneteram, flumethylsulfolim , fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine, or (xvii) flumethylsulfolim, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam ...(xviii) a compound selected from fluoxythioconazole, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and sevoctylamine, or (xix) a compound selected from isotianil, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and sevoctylamine, (xx) methallylpicoxamide, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and sevoctylamine, or (xx) methallylpicoxamide, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, (trifluoromethyl)benzamide and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine, or (xxi) pydiflumetofen, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone and sevoctylamine, or (xxii) a compound selected from pyrimorph, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pyrimorph, pyriophenone and sevoctylamine, or (xxii) a compound selected from pyrimorph, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, cyclobutrifluram, cymoxanil, fulveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide,A compound selected from pydiflumetofen, pyriophenone and seboxylamine, or (xxiii) pyriophenone, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph and seboxylamine. amines, or (xxiv) a composition comprising a compound selected from sevoctylamine, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, and pyriophenone.

[0027] The compositions according to the invention are effective against harmful microorganisms, such as those causing phytopathogenic diseases, in particular phytopathogenic fungi and bacteria.

[0028] The compositions according to the invention are particularly effective against phytopathogenic fungi belonging to the following genera: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula, Pyrenophora); Basidiomycetes (e.g. Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (e.g. Fungi spp., ... imperfecti (also known as Deuteromycetes); e.g., Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Zymoseptoria, Cercospora, Alternaria, Pyricularia, and Schlegelii. Pseudocercosporella; Oomycetes (e.g., Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

[0029] According to the invention, "useful plants" typically include the following plant species: grape vines; cereals such as wheat, barley, rye or oats; beets such as sugar beet or fodder beet; fruits such as pome fruits, drupes or soft fruits, for example apple, pear, plum, peach, almond, cherry, strawberry, raspberry or blackberry; legumes such as beans, lentils, peas or soybeans; oil plants such as rapeseed, canola, poppy, olive, sunflower, coconut, castor bean, cocoa bean or peanut; pumpkin, cucumber plants such as cucumber or melon; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as orange, lemon, grapefruit or mandarin; vegetables such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, cucurbit or paprika; camphor trees such as avocado, cinnamon or camphor; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hop berries; durian; banana; rubber plants; ornamental plants such as grass or flowers, shrubs, broadleaf or evergreen plants, e.g. conifers. This list is not intended to be limiting.

[0030] The term "useful plants" is also to be understood as including useful plants which, as a result of conventional breeding or genetic engineering methods, have been rendered resistant to herbicides such as bromoxynil or several 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 or PPO (protoporphyrinogen-oxidase) inhibitors, etc.). An example of a crop which 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 made tolerant to herbicides or to several herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0031] The term "useful plants" shall also be understood to include useful plants which have been transformed by the use of recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as, for example, those known from toxin-producing bacteria, in particular those of the genus Bacillus.

[0032] The term "useful plants" shall also be understood to include useful substances that have been transformed by the use of recombinant DNA techniques so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing 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 transgenic plants are generally known to the person skilled in the art and are described, for example, in the above-mentioned publications.

[0033] The term "locus" of a useful plant as used herein is intended to include the location where the useful plant is growing, the location where the plant propagation material of the useful plant is sown or the location where the plant propagation material of the useful plant is placed in the soil. An example of such a location is a field, where crops are grown.

[0034] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, and vegetative material, such as cuttings or tubers, e.g. potatoes, that can be used for the propagation of plants. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants may be mentioned. Germinated plants and seedlings that are to be transplanted after germination or emergence from the soil may also be mentioned. These seedlings may be protected by a total or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0035] In a further aspect, the present application also relates to a plant propagation material coated with a composition according to the invention.

[0036] The composition of the invention can also be used in the field of protecting storage articles against fungal attack. According to the invention, the term "storage article" is understood to refer to natural materials of plant and / or animal origin as well as their processed forms, which are taken from their natural life cycle and for which long-term protection is desired. Storage articles of plant origin, such as plants or parts thereof, such as stems, leaves, tubers, seeds, fruits or grains, can be protected either in the freshly harvested state or in processed form, such as pre-dried, moistened, crushed, ground, pressed or roasted. Timber also falls within the definition of storage articles, whether in the form of raw logs, such as building timber, electric poles and electrical barriers, or in the form of finished products, such as furniture or objects made from wood. Storage articles of animal origin are animal hides, leather, fur, hair, etc. The composition according to the invention can prevent adverse effects such as decay, discolouration or mould. Preferably, "storage goods" is understood to refer to 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 present invention, "storage goods" is understood to refer to trees.

[0037] Thus, a further aspect of the present invention is a method of protecting a storage article comprising applying to the storage article a composition according to the present invention.

[0038] The composition of the present invention can also be used in the field of protecting industrial products against fungal attack. According to the present invention, the term "industrial products" includes paper; carpets; constructions; cooling and heating systems; wallboards; ventilation and air conditioning systems, etc. Preferably, "industrial products" is understood to refer to wallboards. The composition of the present invention can prevent adverse effects such as corrosion, discoloration or mold.

[0039] The compositions according to the invention are effective against 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, Fusarium arginum ... subglutinans, Gaeumannomyces graminis, Helminthosporium spp., Microdochium nivale, Phoma spp., Pyrenophora graminea, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia cerealis, Sclerotinia spp., Zymoseptoria spp., Sphacelotheca reilliana, Tilletia spp., Typhula incarnata It is furthermore particularly effective against seed-borne and soil-borne diseases such as Urocystis incarnata, Urocystis occulta, Ustilago spp. or Verticillium spp., and is particularly effective against cereals such as wheat, barley, rye or oats; maize; rice; cotton; soybeans; turf; sugar beet; oilseed rape; potatoes;It may be effective against pathogens in peas, lentils or chickpeas; and in sunflowers.

[0040] The composition according to the invention is preferably selected from the group consisting of 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 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 nuts.

[0041] The compositions according to the invention are particularly useful for controlling the following diseases in the following crops: Alternaria spp. in fruit and vegetables and potatoes, Botrytis cinerea in strawberries, tomatoes, sunflowers, legume crops, vegetables and grapes, Rhizoctonia solani in potatoes and vegetables, Uncinula necator in grapes, Blumeria graminis in cereals, Erysiphe cruciferarum in oilseed rape, Microsphaera diffusa in soybeans, Podosphaera leucotricha in apples, Leveillula taurica in onions, Podosphaera xanthii in legumes. xanthii, Erysiphe cichoracearum in legumes, Fusarium spp. in cereals, Pyrenophora teres in barley, Septoria spp. in cereals such as Zymoseptoria tritici, Septoria spp. in oil crops such as Septoria glycines, Mycosphaerella arachidicola in peanut, Cercospora spp. in tomato, legumes, penatus and oil crops or Cercospora sojinae and Cercospora kikuchii in soybean.

[0042] However, in addition to the actual synergistic action with respect to fungicidal activity, the compositions according to the invention may also have further surprising advantageous properties.Examples of such advantageous properties that may be mentioned are more advantageous decomposition; improved toxicological and / or ecotoxicological behavior; or improved properties of useful plants, including emergence, crop yield, more developed root system, increased tillers, increased plant height, increased leaf blades, less dead basal leaves, stronger tillers, greener leaf color, less fertilizer required, less seed required, more fruitful tillers, earlier flowering, earlier grain maturation, less plant bursting, increased shoot growth, improved plant vigor and earlier germination.

[0043] Some of the compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.

[0044] The compositions according to the invention make it possible in various useful plants to inhibit or destroy phytopathogenic microorganisms present on the plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) while also protecting subsequently growing plant parts from attack by phytopathogenic microorganisms.

[0045] The compositions according to the invention can be applied to phytopathogenic microorganisms, to useful plants, the locus thereof, their propagation material, stored articles or industrial products threatened by microbial attack.

[0046] The compositions according to the invention can be applied before or after infection of useful plants, their propagation material, stored goods or industrial products with microorganisms.

[0047] The amount of the composition according to the invention to be applied depends on various factors, such as the compound employed; the object of the treatment, e.g. plants, soil or seeds; the type of treatment, e.g. spraying, dusting or seed dressing; the purpose of the treatment, e.g. preventive or curative; the type of fungus to be controlled or the duration of application.

[0048] When applied to useful plants, component (A) is typically applied at a rate of from 5 to 2000 g ai / ha, especially from 10 to 1000 g ai / ha, for example 50, 75, 100 or 200 g ai / ha, typically together with component (B) at a rate of from 1 to 5000 g ai / ha, especially from 2 to 2000 g ai / ha, for example 100, 250, 500, 800, 1000, 1500 g ai / ha.

[0049] In agricultural practice, the rate of application of the compositions according to the invention depends on the type of effect desired and typically ranges from 20 to 4000 g of total composition per hectare.

[0050] When the compositions according to the invention are applied for seed treatment, rates of 0.001 to 50 g of compound of component (A) per kg of seed, preferably 0.01 to 10 g per kg of seed, and 0.001 to 50 g of compound of component (B) per kg of seed, preferably 0.01 to 10 g per kg of seed, are generally sufficient.

[0051] The compositions of the present invention may be in any conventional form, such as, for example, twin packs, dry seed treatment powders (DS), emulsifiable concentrates (ES), flowable concentrates (FS), liquid concentrates (LS), wettable powders (WS), capsule suspensions (CF), gels (GF), emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (E), and the like. They may be used in the form of a water-in-oil emulsion (EO), oil-in-water emulsion (EW), microemulsion (ME), dispersion in oil (OD), oil-miscible flowable (OF), oil-miscible liquid (OL), soluble concentrate (SL), suspension for ultra-low volume application (SU), liquid for ultra-low volume application (UL), technical concentrate (TK), dispersible concentrate (DC), wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0052] Such compositions can be prepared in a conventional manner, for example by mixing the active ingredient with at least one suitable inert formulation auxiliary (e.g. diluent, solvent, filler, and other formulation components such as surfactants, biocides, antifreeze agents, adhesion agents, thickeners, and optionally compounds that provide auxiliary effects). If sustained effectiveness is intended, conventional sustained release formulations can also be used. In particular, formulations to be applied in spray form, such as wettable concentrates (e.g. EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules, can contain surfactants such as wetting agents and dispersants, as well as other compounds that provide auxiliary effects, such as condensation products of formaldehyde and naphthalenesulfonate, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0053] The compositions according to the invention may further comprise a pesticide, such as, for example, a fungicide, an insecticide or a herbicide.

[0054] The seed dressing formulation is applied to the seed in a manner known per se, using the composition according to the invention and a diluent in the form of a suitable seed dressing formulation, for example as an aqueous suspension or in the form of a dry powder with good adhesion to the seed. Such seed dressing formulations are known in the art. The seed dressing formulation may also contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as a sustained release capsule or microcapsule.

[0055] In general, the formulations contain 0.01-90% by weight of active agent, 0-20% of agriculturally acceptable surfactants and 10-99.99% of solid or liquid formulation inactive substances and auxiliaries, the active agent being at least the compound of component (A) and the compound of component (B) and optionally other active agents, in particular fungicides or preservatives. The composition in concentrated form generally contains about 2-80%, preferably about 5-70% by weight of active agent. The formulation in application form may contain, for example, 0.01-20% by weight, preferably 0.01-5% by weight of active agent. Commercial products will preferably be formulated as concentrates, while end users will usually utilize diluted formulations.

[0056] Further properties of compositions comprising a compound of formula (I), their methods of application to plants and their rates of use are as described for compositions comprising a compound of formula (I) and further at least one of the above-mentioned components (B). Their application can be before or after infection of the plant or its parts with a fungus. The treatment is preferably carried out before infection. When a compound of formula (I) is used as such, the application rates in the method according to the invention are as described above, for example rates of 5 to 2000 g ai / ha, in particular 10 to 1000 g ai / ha, for example 50, 75, 100 or 200 g ai / ha, are typical. The compound of formula (I) can be applied to the plant once or more than once during the growing season. For use in the method according to the invention, the compound of formula (I) can be converted into the above-mentioned conventional formulations, such as, for example, solutions, emulsifiable concentrates, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose. In each case it should ensure a fine and uniform distribution of the compound of formula (I).

[0057] As used herein, the term "plants" includes fruit and vegetable seedlings, shrubs and crops.

[0058] The following examples are useful for illustrating the present invention, and "active ingredient" refers to a mixture of component (A) and component (B) in a specific mixing ratio. The same formulation can be used for a composition that contains only the compound of formula (I) as the active ingredient. EXAMPLES

[0059] Formulation Examples

[0060] [Table 1]

[0061] The active ingredient is thoroughly mixed with the other formulation ingredients and the mixture is thoroughly ground in a suitable grinding machine to give wettable powders which, when diluted with water, give suspensions of the desired concentration.

[0062] [Table 2]

[0063] The active ingredient is thoroughly mixed with the other formulation ingredients and the mixture is thoroughly ground in a suitable grinding machine to give a powder which can be used directly as a seed treatment.

[0064] emulsifiable concentrate Active ingredient (A):B) = 1:6) 10% Octylphenol polyethylene glycol ether 3% (4-5 moles of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyethylene glycol ether (35 moles of ethylene oxide) 4% Cyclohexanone 30% Xylene Mixture 50%

[0065] Emulsions of any required dilution that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0066] [Table 3]

[0067] Ready-to-use dusts can be obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable grinder. Such powders can also be used for dry seed dressing.

[0068] Extruded Granules %w / w Active ingredient (A):B) = 2:1) 15% Sodium Lignosulfonate 2% Sodium alkylnaphthalene sulfonate 1% Kaolin 82%

[0069] The active ingredient is mixed and ground with the other formulation ingredients, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0070] Suspension concentrate Active ingredient (A):B) = 1:8) 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 moles of ethylene oxide) 6% Sodium Lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0071] The finely divided active ingredient is thoroughly mixed with other formulation ingredients to give a suspension concentrate which can be diluted in water in the desired proportions and used to treat living plants as well as plant propagation material to protect against microbial infestation by spraying, pouring or immersion.

[0072] Flowable concentrates for seed treatment Active ingredient (A):B) = 1:8) 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol ethoxylate (with 10-20 moles of EO) 2% 1,2-Benzisothiazolin-3-one 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0073] The finely divided active ingredient is thoroughly mixed with the other formulation ingredients to give a suspension concentrate which can be further diluted in water for application to seeds, and such dilutions can be used to treat propagation material and protect against microbial infestation by spraying, pouring or immersion.

[0074] Thus, a further aspect of the invention is a method for controlling leaf spot diseases on a plant, comprising applying to the plant, its locus or its propagation material a composition comprising a compound of formula (I).

[0075] Preferred is the method, wherein a plant pathogen attacks the plant and causes diseases such as leaf spot, powdery mildew and blight.

[0076] Preferred is a method which comprises applying a composition comprising a compound of formula (I) to the plant or its locus, preferably to the plant.

[0077] Further preferred is a method comprising applying a composition comprising a compound of formula (I) to the propagation material of the plant.

[0078] The method according to the invention also allows good control of other harmful fungi which often occur in plants, in particular when the compounds of formula (I) are used in combination with at least one of the abovementioned compounds (B).

[0079] Preferred is the compound of formula (I) [ka] (In the formula, R 1 is hydrogen or acetyl, R 2 is chloro, bromo or methoxycarbonyl, and R 3is trifluoromethyl or trifluoromethoxy) and a method for controlling diseases of oilseeds and cereals, particularly diseases caused by leaf spot diseases, which comprises applying to useful plants, their locus or their propagation material a composition comprising a compound of formula (I)

[0080] In general, the weight ratio of component (A) to component (B) is in the range of 2000:1 to 1:1000. The weight ratio of component (A) to component (B) is preferably 100:1 to 1:100, more preferably 20:1 to 1:50, even more preferably 12:1 to 1:25, even more preferably 10:1 to 1:10, still more preferably 5:1 to 1:15, and most preferably 2:1 to 1:5.

[0081] Surprisingly, it has been found that a certain weight ratio of component (A) and component (B) can result in synergistic activity.Accordingly, a further aspect of the present invention is a composition in which component (A) and component (B) are present in the composition in amounts that result in a synergistic effect.This synergistic activity is evident from the fact that the fungicidal activity of a composition comprising component (A) and component (B) is higher than the sum of the fungicidal activities of component (A) and component (B).

[0082] This synergistic activity expands the scope of action of components (A) and (B) in two ways. Firstly, the application rate of components (A) and (B) is reduced while the action remains equally good, which means that the active ingredient mixture still achieves a high degree of control of plant pathogens even when the two individual components become completely ineffective at such a low application rate range. Secondly, there is a significant expansion of the spectrum of plant pathogens that can be controlled.

[0083] A synergistic effect exists whenever the action of the active ingredient combination is higher than the sum of the actions of the individual ingredients. The expected action E of a given active ingredient combination can be calculated according to the so-called Colby formula as follows (COLBY, SR “Calculating synergistic and antagonistic responses of herbicide combination”. Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient (=ai) per liter of spray mixture X=% effect of active ingredient A) using p ppm of active ingredient Y=% effect of active ingredient B) using q ppm of active ingredient.

[0084] According to Colby, the expected (additive) effect of active ingredients A) + B) using p+q ppm of active ingredients is:

number

[0085] If the actual observed effect (O) is higher than the expected effect (E), the effect of the combination is superadditive, i.e. synergistic. Mathematically speaking, synergy corresponds to a positive value of the difference (OE). In the case of purely additive complementary activities (expected activity), said difference (OE) is zero. A negative value of said difference (OE) represents a decrease in activity compared to the expected activity.

[0086] Biological Examples Alternaria solani (Early blight of tomatoes / potatoes): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of nutrient broth containing fungal spores. Test plates were incubated at 24°C and growth inhibition was determined photometrically after 48 hours.

[0087] [Table 4]

[0088] [Table 5]

[0089] [Table 6]

[0090] Botrytis cinerea (gray mold): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of nutrient broth containing fungal spores. Test plates were incubated at 24°C and growth inhibition was determined photometrically after 72 hours.

[0091] [Table 7]

[0092] [Table 8]

[0093] [Table 9]

[0094] [Table 10]

[0095] [Table 11]

[0096] [Table 12]

[0097] [Table 13]

[0098] [Table 14]

[0099] Glomerella lagenarium syn. Colletotrichum lagenarium (Cucurbitaceae anthracnose): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of nutrient broth containing fungal spores. Test plates were incubated at 24°C and growth inhibition was determined photometrically at 620 nm after 72 hours.

[0100] [Table 15]

[0101] [Table 16]

[0102] Mycosphaerella arachidis syn. Cercospora arachidicola (Brown Leaf Spot of Peanut): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of nutrient broth containing fungal spores. Test plates were incubated at 24°C and inhibition of growth was determined photometrically at 620 nm after 5-6 days.

[0103] [Table 17]

[0104] Sclerotinia sclerotiorum (cotton rot, mildew, etc.): Fungal mycelium fragments prepared from fresh liquid cultures were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) before the addition of nutrient broth containing fungal spores. Test plates were incubated at 24°C and growth inhibition was determined photometrically at 620 nm after 72 hours.

[0105] [Table 18]

Claims

1. A composition suitable for controlling diseases caused by plant pathogens, comprising: (A) Formula I: 【Chemical 1】 (In the formula, R 1 is hydrogen or C 1 ~C 3 alkylC(=O)-, and R 2 is a halogen or C 1 ~C 3 alkoxyC(═O)—, and R 3 is C 1 ~C 3 Haloalkyl or C 1 ~C 3 haloalkoxy) or an agriculturally acceptable salt or N-oxide thereof; (B) at least one compound selected from cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine, or a combination thereof; A composition comprising:

2. In the compound of formula (I) or an agriculturally acceptable salt or N-oxide thereof, R 1 is hydrogen or acetyl, and R 2 is chloro, bromo or methoxycarbonyl, and R 3 The composition of claim 1 , wherein is trifluoromethyl or trifluoromethoxy.

3. In the compound of formula (I) or an agriculturally acceptable salt or N-oxide thereof, R 1 is acetyl, and R 3 The composition of claim 1 or 2, wherein is trifluoromethoxy.

4. Component (A) has the structure I.a: 【Chemistry 2】 and / or methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate according to structure I.b: 【Chemistry 3】 3. The composition according to claim 1 or 2, comprising a compound selected from N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide according to the formula (I) or an agriculturally acceptable salt or N-oxide thereof.

5. 3. The composition according to claim 1, comprising as component (B) a fungicide selected from cyclobutrifluram, cymoxanil, flufenoxadiazamun, flumethylsulfolim, fluoxytioconazole, methallylpicoxamide and pydiflumetofen.

6. 3. The composition according to claim 1, wherein the weight ratio of component (A) to component (B) is in the range of 2000:1 to 1:1000.

7. As an active ingredient, (i) a compound selected from cyclobutrifluram, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (ii) a compound selected from cymoxanil, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (iii) a compound selected from fulveneteram, methyl 2-[acetyl-[2-ethylsulfonyl-4-trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (iv) flufenoxadiazam, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (v) a compound selected from flumethylsulfolim, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (vi) a compound selected from fluoxythioconazole, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine, or (vii) a compound selected from isotianil, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine, or (viii) a compound selected from methallyl picoxamide, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine, or (ix) pydiflumetofen, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and a compound selected from cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pyrimorph, pyriophenone, and seboxylamine; (x) a compound selected from pyrimorph, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyriophenone, and seboxylamine; (xi) a compound selected from pyriophenone, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, and seboxylamine, or (xii) compounds selected from seboxylamine, methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, and pyriophenone; 3. The composition of claim 1 or 2, comprising:

8. As an active ingredient, (xiii) a compound selected from cyclobutrifluram, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (xiv) cymoxanil, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine. (xv) a compound selected from fulveneteram, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (xvi) flufenoxadiazam, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine. (xvii) a compound selected from flumethylsulfolim, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (xviii) a compound selected from fluoxythioconazole, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (xix) a compound selected from isotianil, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, methallylpicoxamide, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine; (xx) methallyl picoxamide, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, pydiflumetofen, pyrimorph, pyriophenone, and seboxylamine. (xxi) pydiflumetofen, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pyrimorph, pyriophenone, and seboxylamine. (xxii) pyrimorph, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and a compound selected from cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyriophenone, and seboxylamine. (xxiii) a compound selected from pyriophenone, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, fluveneteram, flufenoxadiazam, flumethylsulfolim, fluoxytioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, and seboxylamine, or (xxiv) compounds selected from seboxylamine, N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, and cyclobutrifluram, cymoxanil, flubeneteram, flufenoxadiazam, flumethylsulfolim, fluoxythioconazole, isotianil, methallylpicoxamide, pydiflumetofen, pyrimorph, and pyriophenone; 3. The composition of claim 1 or 2, comprising:

9. 3. A composition according to claim 1 or 2, comprising one or more further pesticides, preferably one or more further fungicides, insecticides or herbicides.

10. A method for controlling diseases caused by plant pathogens on useful plants or their propagation material, comprising applying to said useful plants, their locus or their propagation material a composition according to claim 1 or 2.

11. 11. The method of claim 10, wherein the plant pathogen attacks plants and causes diseases, in particular leaf spot, powdery mildew and blight.

12. 11. The method of claim 10, comprising applying component (A) at a rate of 5 to 2000 g ai / ha together with 1 to 5000 g ai / ha of component (B).

13. 11. The method of claim 10, wherein when used to treat seeds, the method comprises applying 0.001 to 50 g of the compound of component (A) per kg of seed and 0.001 to 50 g of the compound of component (B) per kg of seed.

14. 3. A coated plant propagation material, wherein the coating comprises a composition according to claim 1 or 2.

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