Substituted thiophenecarboxamides and their derivatives as fungicides.

Abstract

The present disclosure relates to substituted thiophenecarboxamide derivatives of formula (I), their use for controlling plant pathogenic microorganisms, and compositions containing them. TIFF2022538262000096.tif39160

Description

[Technical Field]

[0001] The present invention relates to substituted thiophenecarboxamide derivatives, their use for controlling plant pathogenic microorganisms, and compositions containing them. [Background technology]

[0002] WO2004 / 024692 discloses that some heterocyclic carbonylaminocyclopropanecarboxylic acid derivatives can be used as fungicides. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2004 / 024692 Summary of the Invention [Problem to be solved by the invention]

[0004] Although many bactericides have been developed so far, there is still a need to develop new bactericidal compounds to meet the ever-increasing environmental and economic requirements imposed on modern crop protection agents and compositions.This includes, for example, improving the spectrum of action, safety profile, selectivity, application rate, residue formation and favorable formulation ability.It may also be desirable to have new compounds to prevent the emergence of resistance.

[0005] In at least some of these respects, the present invention provides new compounds that offer advantages over known compounds and compositions. [Means for solving the problem]

[0006] The present invention relates to compounds of formula (I) below, and salts, N-oxides and solvates thereof: [ka]

[0007] In the formula, R 1 , R 2 and R 3 is as described herein.

[0008] The present invention relates to compositions comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable carrier.

[0009] The present invention is directed to methods for preparing the compounds of formula (I) and intermediates thereto described herein.

[0010] The present invention relates to a method for controlling plant pathogenic microorganisms, which method comprises applying at least one compound of formula (I) as defined herein or a composition as defined herein to a plant, plant part, seed, fruit or the soil in which the plant is growing.

[0011] definition The term "alkyl" as used herein, for example in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, is to be understood to mean preferably branched and unbranched alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, sec-butyl, pentyl, iso-pentyl, hexyl, heptyl, octyl, nonyl and decyl, and isomers thereof.

[0012] As used herein, the term "haloalkyl" is preferably understood to mean a branched or unbranched alkyl as defined above, wherein one or more hydrogen substituents are replaced by halogen, either the same or different. Particularly preferred are, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl, and isomers thereof.

[0013] As used herein, the term "cycloalkyl" refers to a non-aromatic monocyclic carbon-containing ring having from 3 to 8 carbon atoms. Examples of saturated cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl groups.

[0014] The term "heterocycle" as used herein refers to a 4-, 5-, or 6-membered saturated or partially unsaturated heterocycle containing 1 to 4 heteroatoms independently selected from the group oxygen, nitrogen, and sulfur. If a ring contains multiple oxygen atoms, they are not immediately adjacent.

[0015] The term "halogen" or "Hal" as used herein shall be understood to mean fluorine, chlorine, bromine or iodine.

[0016] The term "halo" within parentheses (eg, "C1-C6-(halo)alkyl") indicates that one or more halogen substituents, which may be the same or different, may be present.

[0017] As used herein, the term "alkenyl" should be understood to mean preferably branched or unbranched alkenyl, such as vinyl, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl, or 2-methyl-prop-1-en-1-yl groups.

[0018] As used herein, the term "alkynyl" should be understood to mean preferably branched or unbranched alkynyl, such as an ethynyl, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl, or but-3-yn-1-yl group.

[0019] As used herein, the term "aryl" refers to an aromatic hydrocarbon ring system containing 6 to 15 carbon atoms, or 6 to 12 carbon atoms, preferably 6 to 10 carbon atoms. The ring system can be a monocyclic or fused polycyclic (e.g., bicyclic or tricyclic) aromatic ring system. Examples of aryl include, but are not limited to, phenyl, azulenyl, naphthyl, and fluorenyl. Furthermore, when the aryl group is substituted with one or more substituents, it is clear that the substituents may be located at any position on the aryl ring. In particular, when the aryl is a phenyl group, the substituents may be located at one or both ortho positions, one or both meta positions, or para positions, or any combination of these positions. This definition also applies to aryl as part of a compound substituent (e.g., aryloxy).

[0020] As used herein, the term "aralkyl" refers to a C1-C6-alkyl substituted by an aryl, as defined herein. Examples of aralkyl include the benzyl group (-CH2-C6H5).

[0021] As used herein, the term "C1-C6", for example in the context of the definition of "C1-C6-alkyl" or "C1-C6-alkoxy", is to be understood to mean a group having a finite number of carbon atoms from 1 to 6, i.e. 1, 2, 3, 4, 5 or 6 carbon atoms.

[0022] As used herein, the term "leaving group" should be understood to mean a group that is released from a compound in a substitution or elimination reaction, e.g., a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy, methanesulfonate, p-toluenesulfonate, and the like. DETAILED DESCRIPTION OF THE INVENTION

[0023] Active ingredient The present invention relates to compounds of formula (I): [ka]

[0024] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; R 1 and R 2 If both are bromine atoms, R 3 is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; R 3 is selected from the group consisting of a hydrogen atom and a C1-C6-alkyl, then R2 is selected from the group consisting of a bromine atom and an iodine atom; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0025] In a preferred embodiment, R 1 is a chlorine atom.

[0026] In another preferred embodiment, R 1 is a bromine atom.

[0027] In another preferred embodiment, R2 is selected from the group consisting of a fluorine atom, a chlorine atom, and a bromine atom.

[0028] In another preferred embodiment, R 1 is R 2 is different.

[0029] In another preferred embodiment, R 1 is a chlorine atom, and R 2 is a bromine atom.

[0030] In another embodiment, R 2 is selected from the group consisting of a bromine atom, a chlorine atom, and a fluorine atom.

[0031] In another embodiment, R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aralkyl and -C-C-alkyl-cyclopropyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0032] In another preferred embodiment, R 1 is a chlorine atom, and R 2 is a bromine atom, and R 3is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aralkyl and -C-C-alkyl-C-C-cyclopropyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0033] Another aspect of the present invention is a compound of formula (I). [ka]

[0034] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-C-C-cycloalkyl; R 1 and R 2 If both are bromine atoms, R 3is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; R 3 is selected from the group consisting of a hydrogen atom and a C1-C6-alkyl, then R2 is selected from the group consisting of a bromine atom and an iodine atom; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0035] In a preferred embodiment of this aspect, R 1 is a chlorine atom, and R 2 is a bromine atom, and R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aralkyl and -C-C-alkyl-C-C-cycloalkyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0036] Another aspect of the invention relates to the use of compounds of formula (I) for controlling phytopathogenic fungi and / or bacteria on plants or plant parts in crop protection. [ka]

[0037] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cycloproyl; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0038] In a preferred embodiment of this aspect, R 1 is a chlorine atom.

[0039] In a preferred embodiment of this aspect, R 1 is a bromine atom.

[0040] In a preferred embodiment of this aspect, R 2 is selected from the group consisting of a fluorine atom, a chlorine atom, and a bromine atom.

[0041] In a preferred embodiment of this aspect, R 1 is R 2 is different from.

[0042] In a preferred embodiment of this aspect, R 1 is a chlorine atom, and R 2 is selected from the group consisting of fluorine atoms and chlorine atoms.

[0043] In a preferred embodiment of this aspect, R 1 is a chlorine atom, and R 2 is a bromine atom.

[0044] In a preferred embodiment of this aspect, R 3is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl)3 and -C-C-alkyl-cyclopropyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0045] In another preferred embodiment of this aspect, R 1 is a chlorine atom, and R 2 is a bromine atom, and R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aralkyl and -C-C-alkyl-C-C-cyclopropyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0046] In another preferred embodiment of this aspect, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, and fluorine atoms; R 3is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0047] In another preferred embodiment of this aspect, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C1-C6-alkyl, C3-C8-cycloalkyl and aralkyl, However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0048] In another preferred embodiment of this aspect, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C1-C6-alkyl, C3-C8-cycloalkyl and aralkyl, However, R 1 is a chlorine atom, R 2 is not a chlorine atom, except that R 1 is a bromine atom, R 2 is not a bromine atom.

[0049] Another aspect of the invention relates to the use of compounds of formula (I) for controlling phytopathogenic fungi and / or bacteria on plants or plant parts in crop protection. [ka]

[0050] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-C-C-cycloalkyl; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0051] In a preferred embodiment of this aspect, R 1 is a chlorine atom, and R 2 is a bromine atom, and R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aralkyl and -C-C-alkyl-C-C-cycloalkyl, preferably selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, most preferably selected from the group consisting of a hydrogen atom and C-C-alkyl.

[0052] In this case, compounds resulting from combinations that a person skilled in the art would consider excluded based on their specialized knowledge because they are contrary to the laws of nature are not included, for example, ring structures having three or more adjacent oxygen atoms are excluded.

[0053] Depending on the nature of the substituents, the compounds of formula (I) can exist in different stereoisomeric forms. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present invention therefore encompasses both pure stereoisomers and any mixtures of these isomers. Where a compound can exist in equilibrium in two or more tautomeric forms, a reference to the compound by a single tautomeric description is intended to include all tautomeric forms.

[0054] Any compound of the present invention may exist in one or more geometric isomeric forms, depending on the number of double bonds in the compound. Geometric isomers, depending on the nature of the substituents around one double bond or ring, may exist in cis (=Z-) or trans (=E-) form. The present invention therefore relates equally to all geometric isomers and all possible mixtures in all proportions.

[0055] The compound of formula (I) may suitably be in its free form, salt form, N-oxide form or solvate form (eg hydrate).

[0056] Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of the free compound and / or of a salt thereof, such as an agrochemically active salt.

[0057] Pesticidal active salts include acid addition salts of inorganic and organic acids and salts of common bases. Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide, sulfuric acid, phosphoric acid, and nitric acid, and acid salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid, and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkyl sulfonic acids (sulfonic acids having linear or branched alkyl groups having 1 to 20 carbon atoms), aryl sulfonic acids, or aryl disulfonic acids (containing aromatic groups, e.g., 1 or more alkyl groups). and the like, such as phenyl and naphthyl having the above sulfonic acid group, alkylphosphonic acids (phosphonic acids having a linear or branched alkyl group having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic groups, e.g., phenyl and naphthyl having one or two phosphonic acid groups), wherein the alkyl and aryl groups may have further substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0058] Solvates of a compound of formula (I) or a salt thereof are stoichiometric compositions of the compound with a solvent.

[0059] The compounds of formula (I) may exist in multiple crystalline and / or amorphous forms, including unsolvated crystalline forms, solvates and hydrates.

[0060] The present invention relates to any of the compounds of formula (I) disclosed in the Tables and their use in crop protection (i.e. for controlling phytopathogenic fungi and / or bacteria on plants or plant parts and / or for controlling nematodes).

[0061] Another aspect of the present invention relates to a composition comprising at least one compound of formula (I) according to the present invention and at least one agriculturally suitable adjuvant.

[0062] Another aspect of the present invention relates to a method for suppressing bacterial and / or fungal diseases and / or for controlling nematodes, which method comprises applying to plants, plant parts, seeds, fruits or the soil in which the plants grow at least one compound of formula (I) according to the present invention or a composition according to the present invention.

[0063] Another aspect of the present invention relates to the use of the compounds according to the invention or the compositions according to the invention for controlling bacterial and / or fungal diseases and / or for controlling nematodes, preferably they are used to control bacterial or fungal diseases.

[0064] Preferably, the compound or composition according to the invention is effective against diseases caused by powdery mildew pathogens such as Podosphaera species (e.g., Podosphaera leucotricha), Sphaerotheca species (e.g., Sphaerotheca fuliginea); diseases caused by rust pathogens such as Uromyces species (e.g., Uromyces appendiculatus); diseases caused by rust pathogens such as Peronospora species (e.g., Peronospora parasitica), Phytophthora species (e.g., Phytophthora infestans); diseases caused by pathogens from the Oomycetes group, such as Pseudoperonospora species (e.g., Pseudoperonospora infestans), Plasmopara species (e.g., Plasmopara viticola), Pseudoperonospora species (e.g., Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (e.g., Pythium ultimum); diseases caused by pathogens from the Oomycetes group, such as Pseudoperonospora species (e.g., Pythium ultimum), Alternaria species (e.g., Alternaria solani), Cercospora species (e.g., Cercospora beticola), beticola), Colletotrichum species (e.g., Colletotrichum lindemuthanium), and Venturia species (e.g., Venturia inaequalis); leaf blotch diseases and leaf wilt diseases caused by Colletotrichum species (e.g., Colletotrichum lindemuthanium), and Venturia species (e.g., Venturia inaequalis);It is used against diseases caused by bacterial pathogens such as Xanthomonas species (e.g., Xanthomonas campestris pv. campestris), Pseudomonas species (e.g., Pseudomonas syringae pv. tomato), Erwinia species (e.g., Erwinia amylovora), Liberibacter species (e.g., Liberibacter Candidatus), and Ralstonia species (e.g., Ralstonia solanacearum);

[0065] According to a further aspect of the present invention, the compound or composition according to the present invention is used as a plant defense activator. A plant defense inducer according to the present invention is a compound or composition that stimulates the plant's own defense system.

[0066] Methods for preparing compounds of formula (I) The present invention relates to a process for preparing compounds of formula (I), which can be prepared by various routes analogous to known methods (see references therein) and by one or more of the following synthetic routes described herein below and in the experimental section:

[0067] Unless otherwise stated, in the following, R 1 , R 2 and R 3 has the same meaning as given above for compounds of formula (I).

[0068] Method 1 Compounds of formula (I) as defined herein may be prepared by Process 1 which comprises reacting a compound of formula (II) or one of its salts with a compound of formula (III) or one of its salts, as depicted by the following reaction scheme: [ka]

[0069] In the formula, U 1 is a halogen atom, a hydroxy group or a C1-C6-alkoxy group.

[0070] U 1When represents a hydroxy group, Method 1 is advantageously carried out in the presence of a condensing agent. Suitable condensing agents include acid halide-forming agents such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, or thionyl chloride; anhydride-forming agents such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC); or phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphine chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbodinium hexafluorophosphate, N,N′-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphine chloride (BOP-Cl), bromo-tripyrrolidinophosphonium hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), and propanephosphonic anhydride (T3P).

[0071] U 1When represents a halogen atom, method 1 is advantageously carried out in the presence of an acid-binding agent. Suitable acid-binding agents for carrying out method 1 are in each case all inorganic and organic bases customary for such reactions. Preferred are alkali metal carbonates such as cesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, and aromatic bases such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N-methylpiperidine, N,N-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), or diazabicycloundecene (DBU), or pyridine.

[0072] U 1 When represents a C1-C6-alkoxy group, Method 1 can be carried out with an excess of the amine component, optionally in the presence of a Lewis acid such as trimethylaluminum.

[0073] Where appropriate, Method 1 may be carried out in the presence of a base and, where appropriate, in the presence of a solvent, preferably under anhydrous conditions.

[0074] The solvent suitable for carrying out Method 1 is not particularly limited. It can be any common inert organic solvent as long as it does not dissolve the compound, react with it, or exhibit specific interactions with it. Preferably, the following solvents are used: optionally halogenated aliphatic, alicyclic, or aromatic hydrocarbons, such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR™ E or ISOPAR™ G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2 -dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; ureas such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, or sulfones such as sulfolane; and mixtures thereof.

[0075] Method 1 can be carried out in an inert atmosphere such as an argon or nitrogen atmosphere. When carrying out Method 1, 1.1 moles or an excess of the compound of formula (III) and 1 to 5 moles of base can be used per mole of the compound of formula (II). Other ratios of reaction components can also be used. Post-treatment is carried out by known methods.

[0076] Compounds of formula (III) are commercially available or can be prepared by known methods.

[0077] U 1 Compounds of formula (II) where U represents a hydroxy group are commercially available or can be purchased from1 represents a C1-C6-alkoxy group, or by various routes analogous to known methods described in Beilstein Journal of Organic Chemistry (2007), 3, No. 23; Justus Liebigs Annalen der Chemie (1937), 532, 236-49; WO2017212010; WO2003024961; Journal of Agricultural and Food Chemistry (2007), 55(18), 7517-7526 and other references therein, or by one or more of the following synthetic routes (such as Method 3, Method 5 or Method 6) described herein below and in the experimental part.

[0078] U 1 Compounds of formula (II) where U is halogen are commercially available or can be prepared by known methods. 1 represents a hydroxy group.

[0079] U 1 Compounds of formula (II) where U represents a C1-C6-alkoxy group are commercially available or can be prepared by known methods or by method 3, method 5 or method 6 from U 1 represents a hydroxy group.

[0080] Method 2 Compounds of formula (I) as defined herein can be prepared by method C1 from compounds of formula (IV) or one of its salts by carrying out a bromination or chlorination reaction as shown in the following reaction scheme: [ka]

[0081] In the formula, U 2 is a hydrogen atom, a chlorine atom, or a bromine atom, and U 3is a hydrogen atom, a chlorine atom, or a bromine atom, provided that U 2 or U 3 At least one of the groups is a hydrogen atom.

[0082] Method 2 can be carried out according to known methods (WO2008109786, WO2007098356).

[0083] Method 2 is carried out in the presence of a brominating or chlorinating agent and, where appropriate, in the presence of a solvent.

[0084] Suitable brominating or chlorinating agents for carrying out Method 2 are not particularly limited, provided that they are used for bromination or chlorination. Examples of brominating agents include bromine, N-bromosuccinimide, and 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione. Examples of chlorinating agents include N-chlorosuccinimide, sulfuryl chloride, and 1,3-dichloro-5,5-dimethyl-2,4-imidazolidinedione.

[0085] Suitable solvents for carrying out Method 2 are not particularly limited. They can be common inert organic solvents as long as they do not dissolve the compound, react with the compound, or exhibit specific interactions with the compound. Suitable solvents can be, for example, the solvents disclosed in connection with Method 1. To carry out Method 2, it may also be advantageous to use an organic acid such as acetic acid or trifluoroacetic acid as a solvent or co-solvent. To carry out Method 2, it may also be advantageous to use a Lewis acid such as zinc(II) chloride as a catalyst.

[0086] Method 3 Compounds of formula (I) as defined herein can be prepared by method 3 from compounds of formula (V) or one of its salts by carrying out a halogenation reaction as shown in the following reaction scheme: [ka]

[0087] Method 3 can be carried out according to known methods (Angewandte Chemie, International Edition, 52(16), 4440-4444; 2013; ACS Catalysis, 6(11), 7839-7843; 2016; Journal of the American Chemical Society, 2017, 139, 888; Angewandte Chemie, International Edition, 2014, 53, 7928; Journal of the American Chemical Society, 2018, 140, 2789; WO2008156879; WO2012114285).

[0088] Method 3 is carried out in the presence of a halogenating agent and, where appropriate, in the presence of a solvent.

[0089] Suitable halogenating agents for carrying out Method 3 are not particularly limited, provided that they are used for halogenation. Examples of brominating agents include bromine, N-bromosuccinimide, and 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione. Examples of chlorinating agents include N-chlorosuccinimide, sulfuryl chloride, and 1,3-dichloro-5,5-dimethyl-2,4-imidazolidinedione. Examples of brominating agents include iodine, N-iodosuccinimide, iodine chloride, and 1,3-diiodo-5,5-dimethyl-2,4-imidazolidinedione. Examples of fluorinating agents include N-fluorobenzenesulfonimide.

[0090] Suitable solvents for carrying out Method 3 are not particularly limited. They can be common inert organic solvents as long as they do not dissolve the compound, react with it, or exhibit specific interactions with it. Suitable solvents can be, for example, some of the solvents disclosed in connection with Method 1. It may also be advantageous to use an organic acid such as acetic acid or trifluoroacetic acid as a solvent or co-solvent for carrying out Method 3. It may also be advantageous to use a Lewis acid such as zinc(II) chloride as a catalyst for carrying out Method 3. It may also be advantageous to use a transition metal catalyst such as a palladium catalyst for carrying out Method 3. It may also be advantageous to use an appropriate organometallic reagent such as n-butyllithium for carrying out Method 3.

[0091] Method 4 The compounds of formula (I) as defined herein may be prepared by Process 4, which comprises carrying out diazotization of a compound of formula (VI) or one of its salts, followed by aromatic substitution to provide a compound of formula (I), as shown in the reaction scheme below. [ka]

[0092] In the formula, U 4 is an amino group, a chlorine atom, or a bromine atom, and U 5 is an amino group, a chlorine atom, or a bromine atom, provided that U 4 or U 5 At least one of the groups is an amino group.

[0093] Method 4 can be carried out according to known methods (The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496 and references cited therein).

[0094] A compound of formula (VI) as defined herein or one of its salts may be prepared by a process comprising deprotecting a compound of formula (VII) or one of its salts, as shown in the following reaction scheme: [ka]

[0095] In the formula, U 6 is a protected amino group, a chlorine atom, or a bromine atom, and U 7 is a protected amino group, a chlorine atom, or a bromine atom, provided that U 6 or U 7 at least one of U is a protected amino group; 4 is an amino group, a chlorine atom, or a bromine atom, and U 5 is an amino group, a chlorine atom, or a bromine atom, provided that U 4 or U 5 At least one of the groups is an amino group.

[0096] Examples of protecting groups for amino groups include benzyl, 4-methoxybenzyl, allyl, unsubstituted or substituted C1-C6-alkylsulfonyl, trifluoromethylsulfonyl, unsubstituted or substituted phenylsulfonyl, unsubstituted or substituted C1-C6-alkoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, allyloxycarbonyl, acetyl or trifluoroacetyl.

[0097] The deprotection method can be carried out according to known methods for removing protecting groups (Greene's Protective Groups in Organic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example, tert-butoxycarbonyl and benzyloxycarbonyl protecting groups can be removed in an acidic medium (e.g., using hydrochloric acid or trifluoroacetic acid). Benzyl protecting groups can be removed hydrogenolytically using hydrogen in the presence of a catalyst (e.g., palladium / activated carbon). Trifluoroacetyl groups can be removed in a basic medium (e.g., using potassium carbonate or lithium hydroxide).

[0098] Compounds of formula (VI) can be prepared from compounds of formula (VIII) or one of its salts, and compounds of formula (VII) can be prepared from compounds of formula (IX) or one of its salts by reaction with compounds of formula (II) under the conditions described in Method 1. [ka]

[0099] In the formula, U 4 , U 5 , U 6 and U 7 is as defined herein, and U 1 is a halogen atom, a hydroxy group or a C1-C6-alkoxy group.

[0100] Compounds of formula (VIII) and compounds of formula (IX) are commercially available or can be prepared by known methods using reaction conditions similar to those disclosed for preparing compounds of formula (II).

[0101] R 3 The compound of formula (I) or one of its salts, wherein R represents a hydrogen atom, can be converted to R by known methods such as basic hydrolysis. 3is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, a 4-, 5- or 6-membered heterocycle, —C1-C6-alkyl-Si(C1-C6-alkyl)3 and —C1-C6-alkyl-cyclopropyl.

[0102] R 3 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, a 4-, 5- or 6-membered heterocycle, —C1-C6-alkyl-Si(C1-C6-alkyl)3 and —C1-C6-alkyl-cyclopropyl, compounds of formula (I) are also suitable when R 3 represents a hydrogen atom or one of its salts, by known methods.

[0103] Method 5 Compounds of formula (I) can be prepared by method 5 from compounds of formula (X) or one of its salts by carrying out a bromination reaction as shown in the reaction scheme below. [ka]

[0104] Method 5 is carried out in the presence of a brominating agent and, where appropriate, in the presence of a solvent.

[0105] The brominating agents suitable for carrying out Method 5 are not particularly limited as long as they are used for bromination. Examples of the brominating agent include N-bromosuccinimide, bromine, and 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione.

[0106] Suitable solvents for carrying out Method 5 are not particularly limited. They may be common inert organic solvents as long as they do not dissolve the compound, react with it, or exhibit specific interactions with it. Suitable solvents may be, for example, the solvents disclosed in connection with Method 2. It may also be advantageous to use an organic acid such as acetic acid or trifluoroacetic acid as a solvent or co-solvent to carry out Method 5. It may also be advantageous to use a Lewis acid such as zinc(II) chloride as a catalyst to carry out Method 5. It may also be advantageous to use an appropriate organometallic reagent such as n-butyllithium to carry out Method 5.

[0107] Method 6 Compounds of formula (I) can also be prepared from compounds of formula (XI) by method 6, as shown in the reaction scheme below. [ka]

[0108] Method 6 can be carried out according to known methods (The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496 and references cited therein).

[0109] Compounds of formula (XI) as defined herein may be prepared by a process which includes deprotecting a compound of formula (XII) by a deprotection reaction, as shown in the following reaction scheme: [ka]

[0110] In the formula, U 8 is a protected amino group.

[0111] Examples of protecting groups for amino groups include benzyl, 4-methoxybenzyl, allyl, unsubstituted or substituted C1-C6-alkylsulfonyl, trifluoromethylsulfonyl, unsubstituted or substituted phenylsulfonyl, unsubstituted or substituted C1-C6-alkoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, allyloxycarbonyl, acetyl or trifluoroacetyl.

[0112] The deprotection method can be carried out according to known methods for removing protecting groups (Greene's Protective Groups in Organic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example, tert-butoxycarbonyl and benzyloxycarbonyl protecting groups can be removed in an acidic medium (e.g., using hydrochloric acid or trifluoroacetic acid). Benzyl protecting groups can be removed hydrogenolytically using hydrogen in the presence of a catalyst (e.g., palladium / activated carbon). Trifluoroacetyl groups can be removed in a basic medium (e.g., using potassium carbonate or lithium hydroxide).

[0113] Compounds of formula (XI) can also be prepared from compounds of formula (XIII) by reaction with compounds of formula (III), and compounds of formula (XII) can be prepared from compounds of formula (XIV) by reaction with compounds of formula (III) under the conditions described in connection with Method 1. [ka]

[0114] In the formula, U 8 is defined herein, and U 1 is a halogen atom, a hydroxy group or a C1-C6-alkoxy group.

[0115] Compounds of formula (XIII) and (XIV) are commercially available or can be prepared by known methods using reaction conditions similar to those disclosed for preparing compounds of formula (II).

[0116] Method 7 Compounds of formula (I) can be prepared by method 7 via a fluorination reaction as shown in the following scheme. [ka]

[0117] The present invention is 1 , R 2 , and R 3 The present invention also relates to this method, wherein the

[0118] Method 7 can be carried out according to known methods (Journal of the American Chemical Society 2011, 133, 11482 and Organic Process Research & Development 2014, 18, 1041).

[0119] The compounds according to the invention can be prepared according to the methods described above. Nevertheless, it will be understood that a person skilled in the art will be able to adapt these methods according to the details of each compound according to the invention that he wishes to synthesize, based on his general knowledge and available publications.

[0120] Intermediates for the preparation of compounds of formula (I) The present invention relates to intermediates for preparing compounds of formula (I).

[0121] Unless otherwise stated, in the following, R 1 , R 2 and R 3 has the same meaning as provided above for compounds of formula (I).

[0122] Compounds of formula (IIa) are provided: [ka]

[0123] In the formula, R 1 , R 2 and R 3 is as defined herein, and U 1a is a hydroxy group or a C1-C6-alkoxy group, However, the compound of formula (IIa) does not include the following:

[0124] Methyl 4,5-dichloro-3-fluorothiophene-2-carboxylate [2166596-88-7], -4,5-dichloro-3-fluorothiophene-2-carboxylic acid [2166596-87-6], -ethyl 4,5-dibromo-3-fluorothiophene-2-carboxylate [2260624-98-2], -4,5-dibromo-3-fluorothiophene-2-carboxylic acid [1628447-64-2], -methyl 4,5-dibromo-3-chlorothiophene-2-carboxylate [1501789-47-4], -4,5-dibromo-3-iodothiophene-2-carboxylic acid [854626-46-3], -4,5-dibromo-3-chlorothiophene-2-carboxylic acid [503308-99-4], -ethyl 4,5-dibromo-3-chlorothiophene-2-carboxylate [503308-98-3], -methyl 4,5-dibromo-3-fluorothiophene-2-carboxylate [395664-58-1], -tert-butyl 3,4,5-tribromothiophene-2-carboxylate [62224-27-5], -ethyl 3,4,5-tribromothiophene-2-carboxylate [54113-44-9], -3,4,5-tribromothiophene-2-carboxylic acid [53317-05-8] and -Methyl 3,4,5-tribromothiophene-2-carboxylate [24647-80-1].

[0125] Compounds of formula (IVa), (IVb) and (IVc) are further aspects of the present invention. [ka]

[0126] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; R 3a represents C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, a 4-, 5- or 6-membered heterocycle, -C1-C6-alkyl-Si(C1-C6-alkyl)3 and -C1-C6-alkyl-cyclopropyl; R 1 and R 2 If each is a chlorine atom, R 3 is a 4-, 5- or 6-membered heterocycle in (IVa) and (IVb); However, the compounds of formulae (IVa) and (IVc) do not represent the following:

[0127] -1-{[(3,4-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid [2140459-54-5], -methyl 1-{[(3-chloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [2188523-33-1] and -Methyl 1-{[(3-bromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [2175467-77-1].

[0128] Compounds of formula (V) are provided: [ka]

[0129] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 3 is selected from the group consisting of a hydrogen atom, C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; R 1 and R 2 are each a chlorine atom, R 3 is a 4-, 5-, or 6-membered heterocycle; However, the compound of formula (V) does not represent the following:

[0130] -1-{[(4,5-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid [726125-69-5], -but-2-yn-1-yl 1-{[(4,5-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [666857-33-6], -Cyclobutyl 1-{[(4,5-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [666857-32-5], -propyl 1-{[(4,5-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [666857-31-4] and -Methyl 1-{[(4,5-dibromo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate [666857-30-3].

[0131] Compounds of formula (VIa) and (VIb) are another aspect of the present invention. [ka]

[0132] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; However, R 1 is a chlorine atom, R 2 is not a chlorine atom.

[0133] Compounds of formula (VIIa) and (VIIb) are provided: [ka]

[0134] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; R 3 is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl; However, R 1 is a chlorine atom, R 2 is not a chlorine atom; V is a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C1-C6-alkoxycarbonyl, an unsubstituted or substituted benzyloxycarbonyl, an allyloxycarbonyl, an acetyl group or a trifluoroacetyl group.

[0135] Compounds of formula (VIIIa) and (VIIIb) are provided: [ka]

[0136] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; U 1a is a hydroxy group or a C1-C6-alkoxy group; However, R 1 is a chlorine atom, R 2 is neither a chlorine atom nor a fluorine atom; However, R 1 is a bromine atom, R 2 is neither a chlorine atom nor a fluorine atom; However, the compound of formula (VIIIb) does not represent the following:

[0137] -Ethyl 4-amino-3,5-dibromothiophene-2-carboxylate [1394375-09-7].

[0138] Compounds of formula (IXa) and (IXb) are provided: [ka]

[0139] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 2 is selected from the group consisting of bromine atoms, chlorine atoms, iodine atoms, and fluorine atoms; V is a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C1-C6-alkoxycarbonyl group, an unsubstituted or substituted benzyloxycarbonyl, an allyloxycarbonyl group, an acetyl group or a trifluoroacetyl group; U 1a is a hydroxy group or a C1-C6-alkoxy group, U 1a is a hydroxy group or a C1-C6-alkoxy group; However, R 1 is a chlorine atom, R 2 is neither a chlorine atom nor a fluorine atom; However, R 1 is a bromine atom, R 2 is neither a chlorine atom nor a fluorine atom.

[0140] Compounds of formula (XI) and (XIIa) are provided: [ka]

[0141] During the ceremony, V is a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C1-C6-alkoxycarbonyl, an unsubstituted or substituted benzyloxycarbonyl, an allyloxycarbonyl, an acetyl group or a trifluoroacetyl group; R 1 is a bromine atom or a chlorine atom; R 3 is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl.

[0142] Compounds of formula (XIIIa) and (XIVa) are provided: [ka]

[0143] During the ceremony, R 1 is a bromine atom or a chlorine atom; V is a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C1-C6-alkoxycarbonyl, an unsubstituted or substituted benzyloxycarbonyl, an allyloxycarbonyl, an acetyl group or a trifluoroacetyl group; U 1a is a hydroxy group or a C1-C6-alkoxy group, However, the compound of formula (XIIIa) -Methyl 3-amino-4,5-dichlorothiophene-2-carboxylate [1621488-35-4] does not represent, However, the compound of formula (XIVa) does not represent the following:

[0144] -3-acetamido-4,5-dichlorothiophene-2-carboxylic acid [2090448-72-7], -methyl 3-acetamido-4,5-dichlorothiophene-2-carboxylate [632356-39-9], and -Methyl 4,5-dichloro-3-[(methoxycarbonyl)amino]thiophene-2-carboxylate [35707-28-9].

[0145] Compounds of formula (XV) are another aspect of the present invention. [ka]

[0146] During the ceremony, R 1 is a bromine atom or a chlorine atom; R 3 is selected from the group consisting of C-C-haloalkyl, C-C-cyanoalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, aryl, heteroaryl, aralkyl, -C-C-alkyl-heteroaryl, a 4-, 5- or 6-membered heterocycle, -C-C-alkyl-Si(C-C-alkyl) and -C-C-alkyl-cyclopropyl.

[0147] Compositions and Formulations The present invention further relates to compositions, in particular compositions for controlling unwanted microorganisms, comprising one or more compounds of formula (I), which compositions are preferably fungicide compositions.

[0148] Such compositions typically comprise one or more compounds of formula (I) and one or more acceptable carriers, especially one or more agriculturally acceptable carriers.

[0149] Carriers are typically inert solid or liquid natural or synthetic organic or inorganic materials. Carriers typically improve the application of compounds to plants, plant parts, or seeds, for example. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock powders such as kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, and synthetic rock powders such as finely divided silica, alumina, and silicates. Examples of solid carriers typically useful for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, synthetic granules of inorganic and organic powders, and granules of organic materials such as paper, sawdust, coconut shells, corn cobs, and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, organic solvents and combinations thereof. Examples of suitable solvents include, for example, aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, paraffins, alkylbenzenes, xylene, toluene, alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes, or methylene chloride), alcohols and polyhydric alcohols (which may be substituted, etherified, and / or esterified; e.g., butanol or glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (e.g., dimethylformamide), lactams (e.g., N-alkylpyrrolidones), and lactones, polar and non-polar organic chemical liquids from the classes of sulfones and sulfoxides (e.g., dimethyl sulfoxide). The carrier can also be a liquefied gas extender, i.e., a liquid that is gaseous at normal temperature and pressure, such as an aerosol propellant, e.g., halohydrocarbons, butane, propane, nitrogen, and carbon dioxide. The amount of carrier will typically range from 1 to 99.99% by weight of the composition, more preferably from 10 to 99.5% by weight, and most preferably from 20 to 99% by weight.

[0150] The composition may further comprise one or more acceptable adjuvants common in formulating compositions (eg, pesticide compositions), such as one or more surfactants.

[0151] The surfactants can be ionic (cationic or anionic) or non-ionic surfactants, such as ionic or non-ionic emulsifiers, foaming agents, dispersing agents, wetting agents and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene and / or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty esters of polyhydric alcohols, and derivatives of compounds containing sulfates, sulfonates, phosphates (e.g., alkylsulfonates, alkyl sulfates, aryl sulfonates), protein hydrolysates, lignosulfite waste liquor, and methylcellulose.Surfactants are typically used when the compound of formula (I) and / or the carrier are insoluble in water and the application is carried out in water. The amount of surfactant, in turn, typically ranges from 5 to 40% by weight of the composition.

[0152] Further examples of adjuvants that are common in formulating agrochemical compositions include water repellents, desiccants, binders (adhesives, tackifiers, fixatives, e.g. carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes, e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, e.g. cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g. low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability), dyes or pigments (e.g. inorganic pigments, e.g. oxidizing agents, iron, titanium dioxide and Prussian blue; organic dyes such as alizarin, azo and metal phthalocyanine dyes), antifoaming agents (e.g. silicone antifoams and magnesium stearate), preservatives (e.g. dichlorophen and benzyl alcohol hemiformal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clay and finely divided silica), spreading agents, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (e.g. micronutrients, e.g. salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrating agents, sequestering agents and complexing agents.

[0153] The choice of adjuvant is related to the intended application form of the compound of formula (I) and / or its physical properties.In addition, adjuvant can be selected to provide the composition with specific properties (technical, physical and / or physiological properties) or the use form produced therefrom.The choice of adjuvant can customize the composition to meet specific needs.

[0154] The compositions may be in any common form, such as solutions (e.g., aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, dusts, pastes, soluble powders, soluble granules, sprayable granules, suspoemulsions, natural and synthetic products impregnated with the compounds of the invention, fertilizers, and even microcapsules in polymeric materials. The compounds of formula (I) may be in suspended, emulsified, or dissolved form.

[0155] The compositions can be provided to the end user as ready-to-use formulations, i.e., they can be applied directly to plants or seeds by suitable equipment, such as spraying or dusting equipment, or they can be provided to the end user in the form of a concentrate that must be diluted, preferably with water, before use.

[0156] Such compositions may be prepared in conventional manner, for example by mixing a compound of formula (I) with one or more suitable auxiliaries as disclosed hereinabove.

[0157] The composition generally comprises 0.01 to 99% by weight, 0.05 to 98% by weight, preferably 0.1 to 95% by weight, more preferably 0.5 to 90% by weight, most preferably 10 to 80% by weight of a compound of formula (I).

[0158] The compounds and compositions containing them can be mixed with other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners, or semiochemicals, to broaden the spectrum of activity or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides, and bactericides are disclosed in the Pesticide Manual, 17th edition.

[0159] The active ingredients specified herein by common name are known and are described, for example, in The Pesticide Manual (16th Ed. British Crop Protection Council) or can be found on the internet (e.g. www.alanwood.net / pesticides).

[0160] Where compound (A) or compound (B) can exist in tautomeric forms, it is understood herein above and below that such compounds also include the corresponding tautomeric forms, where applicable, even if these are not specifically mentioned in each case.

[0161] All listed mixing partners of classes (1) to (15) can, if their functional groups allow, optionally form salts with suitable bases or acids.

[0162] 1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) microbenzyl phosphate, Butanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazole, (1.018) Prothioconazole, (1.019) Pyrisoxazole, (1.020) Spiroxamine, (1.021) Tebuconazole, (1.022) Tetraconazole, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.033)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.035)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.036)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.037)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl) (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl )-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl) )-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2 ,4-Dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1. 050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) Mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2, 4-Triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2- Methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)- 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyl Imidoformamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N -ethyl-N-methylimidoformamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N'-[5 -bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N. -methylimidoformamide, (1.081) Ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl] propyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, (1.087) N-isopropyl-N′-[5-methoxy-2-methyl-4-(2,2, 2-trifluoro-1-hydroxy)-1-phenylethyl)phenyl]-N-methylimidoformamide, (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole.

[0163] 2) Inhibitors of the respiratory chain at complex I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimer enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) Isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumide, (2.021) Sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H -pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) Inpirfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) Fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3 S)-7-Fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide , (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucipram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl) -5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5 -methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoin, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide.

[0164] 3) Inhibitors of the respiratory chain at complex III, such as (3.001) ametoctrazine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.01 2) Fluoxastrobin, (3.013) Kresoxim-methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametstrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxy imino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamide, (3.0 26) Mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) Methyltetraprole, (3.031) Florylpicoxamid.

[0165] 4) Mitosis and cell division inhibitors, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridaclomethyl, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridine-3 -yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6- difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

[0166] 5) Compounds capable of multisite action, such as (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper chloride basic, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5. 015) Metiram, (5.016) Metiram zinc, (5.017) Oxine-copper, (5.018) Propineb, (5.019) Sulfur and sulfur agents, for example calcium polysulfide, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram, (5.023) 6-Ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0167] 6) Compounds capable of inducing host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[0168] 7) Inhibitors of amino acid and / or protein biosynthesis, such as (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0169] 8) Inhibitors of ATP production, for example (8.001) silthiofam.

[0170] 9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0171] 10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0172] 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) tolprocarb.

[0173] 12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0174] 13) Signal transduction inhibitors, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.

[0175] 14) Compounds capable of acting as uncouplers, such as (14.001) fluazinam, (14.002) meptyldinocap.

[0176] 15) (15.001) Abscisic acid, (15.002) Benthazole, (15.003) Bethoxazin, (15.004) Capsimycin, (15.005) Carvone, (15.006) Chinomethionate, (15.007) Kufuraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl aluminum, (15.013) Fosetyl calcium, (15.014) Fosetyl -sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts, (15.025) phosphoric acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriophenone (chlazafenone), (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl- 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}- 1,3-Thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3- [2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate nate, (15.041) Ipflufenoquin, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) Fluoxastrobin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-Phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole- 2-Thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-yn-1-yl{ 6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[( {[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N′-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide), (15.066) (2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl) Quinoline), (15.069) (1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline) (15.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074) methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.075) (N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15.076) N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl (15.077) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.078) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropane-carboxamide, (15.080) N-(2-Fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.082) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-Methoxy-C-methyl-carboxylic acid N-[(Z)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide, (15.086) 4,4-Dimethyl-1-[[4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl]pyrrolidin-2-one, N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.090) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl}-1,. 2,4-Oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole -3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3- on, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15 .106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) Ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.109) N,N-Dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide (15.113) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.119) 3-[2-(1- {[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.120) 9-Fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl Further fungicides selected from the group consisting of ethyl-3,4-dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide and (15.127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide.

[0177] Another aspect of the present invention relates to one or more of the following compound combinations:

[0178] (I.01)+(1.001)、(I.01)+(1.002)、(I.01)+(1.003)、(I.01)+(1.004)、(I.01)+(1.005)、(I.01)+(1.006)、(I.01)+(1.007)、(I.01)+(1.008)、(I.01)+(1.009)、(I.01)+(1.010)、(I.01)+(1.011)、(I.01)+(1.012)、(I.01)+(1.013)、(I.01)+(1.014)、(I.01)+(1.015)、(I.01)+(1.016)、(I.01)+(1.017)、(I.01)+(1.018)、(I.01)+(1.019)、(I.01)+(1.020)、(I.01)+(1.021)、(I.01)+(1.022)、(I.01)+(1.023)、(I.01)+(1.024)、(I.01)+(1.025)、(I.01)+(1.026)、(I.01)+(1.027)、(I.01)+(1.028)、(I.01)+(1.029)、(I.01)+(1.030)、(I.01)+(1.031)、(I.01)+(1.032)、(I.01)+(1.033)、(I.01)+(1.034)、(I.01)+(1.035)、(I.01)+(1.036)、(I.01)+(1.037)、(I.01)+(1.038)、(I.01)+(1.039)、(I.01)+(1.040)、(I.01)+(1.041)、(I.01)+(1.042)、(I.01)+(1.043)、(I.01)+(1.044)、(I.01)+(1.045)、(I.01)+(1.046)、(I.01)+(1.047)、(I.01)+(1.048)、(I.01)+(1.049)、(I.01)+(1.050)、(I.01)+(1.051)、(I.01)+(1.052)、(I.01)+(1.053)、(I.01)+(1.054)、(I.01)+(1.055)、(I.01)+(1.056)、(I.01)+(1.057)、(I.01)+(1.058)、(I.01)+(1.059)、(I.01)+(1.060)、(I.01)+(1.061)、(I.01)+(1.062)、(I.01)+(1.063)、(I.01)+(1.064)、(I.01)+(1.065)、(I.01)+(1.066)、(I.01)+(1.067)、(I.01)+(1.068)、(I.01)+(1.069)、(I.01)+(1.070)、(I.01)+(1.071)、(I.01)+(1.072)、(I.01)+(1.073)、(I.01)+(1.074)、(I.01)+(1.075)、(I.01)+(1.076)、(I.01)+(1.077)、(I.01)+(1.078)、(I.01)+(1.079)、(I.01)+(1.080)、(I.01)+(1.081)、(I.01)+(1.082)、(I.01)+(1.083)、(I.01)+(1.084)、(I.01)+(1.085)、(I.01)+(1.086)、(I.01)+(1.087)、(I.01)+(1.088)、(I.01)+(1.089)、(I.01)+(1.090)、(I.01)+(1.091)、(I.01)+(2.001)、(I.01)+(2.002)、(I.01)+(2.003)、(I.01)+(2.004)、(I.01)+(2.005)、(I.01)+(2.006)、(I.01)+(2.007)、(I.01)+(2.008)、(I.01)+(2.009)、(I.01)+(2.010)、(I.01)+(2.011)、(I.01)+(2.012)、(I.01)+(2.013)、(I.01)+(2.014)、(I.01)+(2.015)、(I.01)+(2.016)、(I.01)+(2.017)、(I.01)+(2.018)、(I.01)+(2.019)、(I.01)+(2.020)、(I.01)+(2.021)、(I.01)+(2.022)、(I.01)+(2.023)、(I.01)+(2.024)、(I.01)+(2.025)、(I.01)+(2.026)、(I.01)+(2.027)、(I.01)+(2.028)、(I.01)+(2.029)、(I.01)+(2.030)、(I.01)+(2.031)、(I.01)+(2.032)、(I.01)+(2.033)、(I.01)+(2.034)、(I.01)+(2.035)、(I.01)+(2.036)、(I.01)+(2.037)、(I.01)+(2.038)、(I.01)+(2.039)、(I.01)+(2.040)、(I.01)+(2.041)、(I.01)+(2.042)、(I.01)+(2.043)、(I.01)+(2.044)、(I.01)+(2.045)、(I.01)+(2.046)、(I.01)+(2.047)、(I.01)+(2.048)、(I.01)+(2.049)、(I.01)+(2.050)、(I.01)+(2.051)、(I.01)+(2.052)、(I.01)+(2.053)、(I.01)+(2.054)、(I.01)+(2.055)、(I.01)+(2.056)、(I.01)+(2.057)、(I.01)+(2.058)、(I.01)+(2.059)、(I.01)+(3.001)、(I.01)+(3.002)、(I.01)+(3.003)、(I.01)+(3.004)、(I.01)+(3.005)、(I.01)+(3.006)、(I.01)+(3.007)、(I.01)+(3.008)、(I.01)+(3.009)、(I.01)+(3.010)、(I.01)+(3.011)、(I.01)+(3.012)、(I.01)+(3.013)、(I.01)+(3.014)、(I.01)+(3.015)、(I.01)+(3.016)、(I.01)+(3.017)、(I.01)+(3.018)、(I.01)+(3.019)、(I.01)+(3.020)、(I.01)+(3.021)、(I.01)+(3.022)、(I.01)+(3.023)、(I.01)+(3.024)、(I.01)+(3.025)、(I.01)+(3.026)、(I.01)+(3.027)、(I.01)+(3.028)、(I.01)+(3.029)、(I.01)+(3.030)、(I.01)+(3.031)、(I.01)+(4.001)、(I.01)+(4.002)、(I.01)+(4.003)、(I.01)+(4.004)、(I.01)+(4.005)、(I.01)+(4.006)、(I.01)+(4.007)、(I.01)+(4.008)、(I.01)+(4.009)、(I.01)+(4.010)、(I.01)+(4.011)、(I.01)+(4.012)、(I.01)+(4.013)、(I.01)+(4.014)、(I.01)+(4.015)、(I.01)+(4.016)、(I.01)+(4.017)、(I.01)+(4.018)、(I.01)+(4.019)、(I.01)+(4.020)、(I.01)+(4.021)、(I.01)+(4.022)、(I.01)+(4.023)、(I.01)+(4.024)、(I.01)+(4.025)、(I.01)+(4.026)、(I.01)+(5.001)、(I.01)+(5.002)、(I.01)+(5.003)、(I.01)+(5.004)、(I.01)+(5.005)、(I.01)+(5.006)、(I.01)+(5.007)、(I.01)+(5.008)、(I.01)+(5.009)、(I.01)+(5.010)、(I.01)+(5.011)、(I.01)+(5.012)、(I.01)+(5.013)、(I.01)+(5.014)、(I.01)+(5.015)、(I.01)+(5.016)、(I.01)+(5.017)、(I.01)+(5.018)、(I.01)+(5.019)、(I.01)+(5.020)、(I.01)+(5.021)、(I.01)+(5.022)、(I.01)+(5.023)、(I.01)+(6.001)、(I.01)+(6.002)、(I.01)+(6.003)、(I.01)+(6.004)、(I.01)+(7.001)、(I.01)+(7.002)、(I.01)+(7.003)、(I.01)+(7.004)、(I.01)+(7.005)、(I.01)+(7.006)、(I.01)+(8.001)、(I.01)+(9.001)、(I.01)+(9.002)、(I.01)+(9.003)、(I.01)+(9.004)、(I.01)+(9.005)、(I.01)+(9.006)、(I.01)+(9.007)、(I.01)+(9.008)、(I.01)+(9.009)、(I.01)+(10.001)、(I.01)+(10.002)、(I.01)+(10.003)、(I.01)+(11.001)、(I.01)+(11.002)、(I.01)+(12.001)、(I.01)+(12.002)、(I.01)+(12.003)、(I.01)+(12.004)、(I.01)+(13.001)、(I.01)+(13.002)、(I.01)+(13.003)、(I.01)+(13.004)、(I.01)+(13.005)、(I.01)+(13.006)、(I.01)+(14.001)、(I.01)+(14.002)、(I.01)+(15.001)、(I.01)+(15.002)、(I.01)+(15.003)、(I.01)+(15.004)、(I.01)+(15.005)、(I.01)+(15.006)、(I.01)+(15.007)、(I.01)+(15.008)、(I.01)+(15.009)、(I.01)+(15.010)、(I.01)+(15.011)、(I.01)+(15.012)、(I.01)+(15.013)、(I.01)+(15.014)、(I.01)+(15.015)、(I.01)+(15.016)、(I.01)+(15.017)、(I.01)+(15.018)、(I.01)+(15.019)、(I.01)+(15.020)、(I.01)+(15.021)、(I.01)+(15.022)、(I.01)+(15.023)、(I.01)+(15.024)、(I.01)+(15.025)、(I.01)+(15.026)、(I.01)+(15.027)、(I.01)+(15.028)、(I.01)+(15.029)、(I.01)+(15.030)、(I.01)+(15.031)、(I.01)+(15.032)、(I.01)+(15.033)、(I.01)+(15.034)、(I.01)+(15.035)、(I.01)+(15.036)、(I.01)+(15.037)、(I.01)+(15.038)、(I.01)+(15.039)、(I.01)+(15.040)、(I.01)+(15.041)、(I.01)+(15.042)、(I.01)+(15.043)、(I.01)+(15.044)、(I.01)+(15.045)、(I.01)+(15.046)、(I.01)+(15.047)、(I.01)+(15.048)、(I.01)+(15.049)、(I.01)+(15.050)、(I.01)+(15.051)、(I.01)+(15.052)、(I.01)+(15.053)、(I.01)+(15.054)、(I.01)+(15.055)、(I.01)+(15.056)、(I.01)+(15.057)、(I.01)+(15.058)、(I.01)+(15.059)、(I.01)+(15.060)、(I.01)+(15.061)、(I.01)+(15.062).(I.01)+(15.063).(I.01)+(15.064).(I.01)+(15.065)、(I.01)+15.066)、(I.01)+(15.067)、(I.01)+(15.068)、(I.01)+(15. 069)、(I.01)+(15.070)、(I.01)+(15.071)、(I.01)+(15.072)、(I.01)+(15.073)、(I.01)+(15.074)、(I.01)+(15.075)、(I.01)+(15.076)、(I.01)、(I.01)+(15.077)、(I.01)+(15.078)、(I.01)+(15.079)、(I.01)+(15.080)、(I.01)+(15.081)、(I.01)+(15.082)、(I.01)+(15.083)、(I.01)+(15.084)、(I.01)+(15.085)、(I.01)+(15.086)、(I.01)+(15.087)、(I.01)+(15.088)、(I.01)+(15.089)、(I.01)+(15.090)、(I.01)+(15.091)、(I.01)+(15.092)、(I.01)+(15.093)、(I.01)+(15.094)、(I.01)+(15.095)、(I.01)+(15.096)、(I.01)+(15.097)、(I.01)+(15.098)、(I.01)+(15.099)、(I.01)+(15.100)、(I.01)+(15.101)、(I.01)+(15.102)、(I.01)+(15.103)、(I.01)+(15.104)、(I.01)+(15.105)、(I.01)+(15.106)、(I.01)+(15.107)、(I.01)+(15.108)、(I.01)+(15.109)、(I.01)+(15.110)、(I.01)+(15.111)、(I.01)+(15.112)、(I.01)+(15.113)、(I.01)+(15.114)、(I.01)+(15.115)、(I.01)+(15.116)、(I.01)+(15.117)、(I.01)+(15.118)、(I.01)+(15.119)、(I.01)+(15.120)、(I.01)+(15.121)、(I.01)+(15.122)、(I.01)+(15.123)、(I.01)+(15.124)、(I.01)+(15.125)、(I.01)+(15.126)、(I.01)+(15.127)。

[0179] In these combinations, the first component is a compound of formula (I) as defined in Table I.1 (e.g., I.01), and the second component is a fungicide selected from Groups 1-15 as defined herein. For example, the combination (I.01)+(1.001) corresponds to a combination comprising compounds I.01 and cyproconazole (1.001) in Table I.1.

[0180] In some other embodiments, the compound combination corresponds to the above combination in which compound (I.01) is replaced with any one of the compounds listed in Table I.1.

[0181] The compound of formula (I) and the fungicide selected from groups (1) to (15) may be present in a weight ratio ranging from 100:1 to 1:100 (compound of formula (I) : fungicide selected from groups (1) to (15)), or ranging from 50:1 to 1:50, or ranging from 20:1 to 1:20. Further examples of weight ratio ranges include 95:1 to 1:95, 90:1 to 1:90, 85:1 to 1:85, 80:1 to 1:80, 75:1 to 1:75, 70:1 to 1:70, 65:1 to 1:65, 60:1 to 1:60, 55:1 to 1:55, 45:1 to 1:45, 40:1 to 1:40, 35:1 to 1:35, 30:1 to 1:30, 25:1 to 1:25, 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, and the like.

[0182] Additional fungicides selected from groups 1-15 as defined herein may be added to the compound combination.

[0183] The compounds of formula (I) and compositions containing them may be combined with one or more biopesticides.

[0184] Examples of biopesticides that can be combined with the compounds of formula (I) and compositions containing them include:

[0185] (A) an antibacterial agent selected from the group consisting of: (A1) Bacteria, such as (A1.1) Bacillus subtilis, in particular the strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, described in U.S. Pat. No. 6,060,051); (A1.2) Bacillus amyroliquefaciens, in particular the strain D747 (available from Certis, US as Double Nickel™, accession number FERMBP-8234, disclosed in U.S. Pat. No. 7,094,592); (A1.3) Bacillus pumilus, in particular the strain BUF-33 (NRRL accession number 50185); (A1.4) Bacillus subtilis Amyroliquefaciens strain FZB24 (available as Taegro® from Novozymes, US); (A1.5) Paenibacillus strain, accession number NRRLB-50972 or accession number NRRLB-67129, described in International Patent Publication No. WO2016 / 154297; and (A2) Fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of the strain DSM 14940; (A2.2) Aureobasidium pullulans blastospores of the strain DSM 14941; (A2.3) Aureobasidium pullulans, in particular a mixture of blastospores of the strains DSM 14940 and DSM 14941; (B) a fungicide selected from the group consisting of: (B1) Bacteria, such as (B1.1) Bacillus subtilis, in particular the strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, described in U.S. Pat. No. 6,060,051); (B1.2) Bacillus pumilus, in particular the strain QST2808 (available from Bayer CropScience LP, US as SONATA®, accession number NRRLB-30087, described in U.S. Pat. No. 6,245,551); (B1.3) Bacillus pumilus, in particular the strain GB34 (available from Bayer AG, DE as Yield Shield®); (B1.4) Bacillus pumilus (B1.5) Bacillus amyroliquefaciens, particularly strain D747 (available from Certis, US under the trade name Double Nickel, deposit number FERMBP-8234, disclosed in U.S. Pat. No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tec, Taiwan under BIOBAC® WP, registered as a biobactericide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus amyroliquefaciens strain MBI600 (BASF (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) Bacillus subtilis var. amyroliquefaciens strain FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as the fungicides TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5); (B1.10) Bacillus mycoides, isolate J (available from Certis USA as BmJ TGAI or WG); (B1.11) Bacillus licheniformis, specifically strain SB3086 (available from Novozymes as EcoGuard™ Biofungicide and Green Releaf); (B1.12) Paenibacillus strain, accession number NRRLB-50972 or accession number NRRLB-67129, described in International Patent Publication No. WO2016 / 154297.

[0186] In some embodiments, the biopesticide is a Bacillus subtilis or Bacillus Amyroliquefaciens strain that produces a fengycin or plipastatin-type compound, an iturin-type compound, and / or a surfactin-type compound. For background, see the following review article: Ongena, M., et al., "Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol," Trends in Microbiology, Vol. 16, No. 3, March 2008, pp. 115-125.Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, described in U.S. Patent No. 6,060,051), Bacillus Amyroliquefaciens strain D747 (available from Certis, US as Double Nickel™, accession number FERMBP-8234, disclosed in U.S. Patent No. 7,094,592); Bacillus subtilis MBI600 (available from Becker Underwood, US as SUBTILEX™, EPA registration number 71840-8); Bacillus subtilis Y1336 (Bion-Tec, available from Taiwan as BIOBAC® WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277; Bacillus amyroliquefaciens, specifically strain FZB42 (available from ABiTEP, DE as RHIZOVITAL®); and Bacillus subtilis var. amyroliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia, or Syngenta Crop Protection, LLC, Greensboro, North Carolina, as the fungicide TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)).

[0187] (B2) Fungi, for example: (B2.1) Coniothyrium minitans, in particular the strain CON / M / 91-8 (deposit number DSM-9660; for example Contans® from Bayer); (B2.2) Metschnikowia fructicola, in particular the strain NRRLY-30752 (for example Shemer®); (B2.3) Microsphaeropsis ochracea (for example Microx® from Prophyta); (B2.5) Trichoderma spp., for example Trichoderma atroviride atroviride, strain SC1 described in International Patent Application No. PCT / IT2008 / 000196; (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22, / ATCC208479, e.g., PLANTSHIELDT-22G, Rootshield®, and TurfShield from BioWorks, US); (B2.14) Gliocladium roseum, strain 321U from WF Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum (Trichoderma from Isagro) asperellum, strain ICC012; (B2.37) Trichoderma asperellum (from Isagro), strain SKT-1 (e.g., ECO-HOPE® from Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, strain CNCMI-1237 (e.g., Esquive® WP from Agrauxine, FR); (B2.39) Trichoderma atroviride, strain number V08 / 002387; (B2.40) Trichoderma atroviride, strain NMI number V08 / 002388; (B2.41) Trichoderma atroviride, strain NMI number V08 / 002389; (B2.42) Trichoderma atroviride, strain NMI number V08 / 002390; (B2.43) Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC20476 (IMI206040); (B2.45) Trichoderma atroviride atroviride, strain T11 (IMI352941 / CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US); (B2.49) Trichoderma harzianum, in particular strain KD (e.g. Trichoplus (obtained by Becker Underwood) from Biological Control Products, SA); (B2.50) Trichoderma harzianum, strain ITEM908 (e.g. from Koppert Trianum-P; (B2.51) Trichoderma harzianum, strain TH35 e.g., Root-Pro by Mycontrol; (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard 12G by Certis, US); (B2.53) Trichoderma viride, strain TV1 (e.g. Trianum-P by Koppert); (B2.54) Ampelomyces quisqualis, in particular the strain AQ10 (e.g. AQ10® by Intrachem Bio Italia); (B2.56) Aureobasidium pullulans, in particular blastospores of the strain DSM 14940; (B2.57) Aureobasidium pullulans, in particular blastospores of the strain DSM 14941; (B2.58) Aureobasidium pullulans, in particular a mixture of blastospores of the strains DSM 14940 and DSM 14941 (e.g. bio-ferm, (B2.64) Cladosporium cladosporioides, strain H39 (by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g. Prestop® by AgBio Inc., also e.g. Primastop® by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly Verticillium Conidia of strain KV01 (designated B. lecanii) (e.g., Vertalec® by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-16511); (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., BioDerma by AGROBIOSOL DE MEXICO, SA DE CV); (B2.79) Trichoderma harzianum, strain DB 103 (e.g., T-Gro 7456 by Dagutat Biolab); (B2.80) Trichoderma polysporum polysporum, strain IMI206039 (e.g. Binab TF WP from BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum (e.g. Tricovab from Ceplac, Brazil); (B2.83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen® from Botry-Zen Ltd, NZ); (B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 (CBS276.92; e.g. Dutch Trig from Tree Care Innovations); (B2.86) Verticillium chlamydosporium chlamydosporium; (B2.87) A mixture of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC080 (e.g., the product known as BIO-TAM® from Bayer CropScience LP, US).

[0188] Further examples of biopesticides which may be combined with the compounds of formula (I) and compositions containing same are:

[0189] Bacillus cereus, in particular B. cereus strain CNCM I-1562 and Bacillus firmus strain I-1582 (accession number CNCM I-1582), Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), B. thuringiensis subsp. aizawai, in particular, strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematodes)-PR3 (Accession No. ATCC SD-5834), Streptomyces microflavus strain AQ6121 (QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (Accession No. NRRL 30232); Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium spp., in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM 3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular strain IFPC 200613 or strain Apopka 97 (accession number ATCC 20874), and Paecilomyces lilacinus, in particular P. fungi and yeasts selected from the group consisting of: Bacillus lilacinus strain 251 (AGAL 89 / 030550); a virus selected from the group consisting of Adoxophyes orana granulosis virus (GV), codling moth (Cydia pomonella granulosis virus (GV), Helicoverpa armigera nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda mNPV, and Spodoptera littoralis (African cotton leafworm) NPV; Bacteria and fungi that can be added as an "inoculant" to plants or plant parts or plant organs and that, due to their specific properties, enhance plant growth and plant health.

[0190] Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp. spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp.

[0191] Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biopesticides, such as garlic (Allium sativum), wormwood (Artemisia absinthium), azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, American anthelminticum (Chenopodium anthelminticum), chitin, Armour-Zen, Dryopteris filix-mas, horsetail (Equisetum arvense), Fortune Aza, Fungastop, Heads Up (quinoa saponin extract), Pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, ("Requiem® Insecticide"), Rotenone, Ryania / Ryanodine, Comfrey (Symphytum officinale), Tanacetum vulgare, Thymol, Triact 70, TriCon, Nasturtium (Tropaeulum majus), Stinging Nettle (Urtica dioica), Veratrin, Mistletoe (Viscum album), Brassicaceae extracts, especially rapeseed powder or mustard powder.

[0192] Examples of insecticides, acaricides and nematicides which may be mixed with the compounds of formula (I) and compositions containing them are as follows:

[0193] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, e.g., alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, e.g., acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP. , dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, O-(methoxyaminothiophosphoryl) isopropyl salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, Omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion; (2) GABA-gated chloride channel blockers, such as cyclodiene organochlorines, such as chlordane and endosulfan; or phenylpyrazoles (fiproles), such as ethiprole and fipronil; (3) Sodium channel regulators, for example, pyrethroids, for example, acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empe methrin [(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, fenothrin [(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin, and transfluthrin; or DDT; or methoxychlor; (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, for example, neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam; or nicotine; or sulfoxaflor or flupyradifurone; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, e.g., spinetoram and spinosad; (6) glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin, and milbemectin; (7) Juvenile hormone mimetics, for example, juvenile hormone analogs, such as hydroprene, kinoprene, and methoprene; or fenoxycarb; or pyriproxyfen; (8) Various nonspecific (multi-site) inhibitors, such as alkyl halides, e.g., methyl bromide and other alkyl halides, or chloropicrin, or sulfuryl fluoride, or borax, or tartar emetic, or methyl isocyanate generators, e.g., dazomet and metham; (9) Chordotonal modulators, such as pymetrozine or flonicamide; (10) Mite growth inhibitors, such as clofentezine, hexythiazox, and diflobidazine; or etoxazole; (11) Microbial disruptors of insect gut membranes, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, and Bacillus thuringiensis subspecies tenebrionis, tenebrionis), and Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1; or (12) Inhibitors of mitochondrial ATP synthase, for example, ATP disruptors, such as diafenthiuron; or organotin compounds, such as azocyclotin, cyhexatin, and fenbutatin oxide; or propargite; or tetradifon; (13) Uncouplers of oxidative phosphorylation by disrupting the proton gradient, such as chlorfenapyr, DNOC, and sulfluramide; (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocylam, and thiosultap sodium; (15) Chitin biosynthesis inhibitors (type 0), such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron; (16) Chitin biosynthesis inhibitors (type 1), such as buprofezin; (17) Molting disruptors (especially in the order Diptera, i.e., Diptera), e.g., Cyromazine; (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide; (19) Octopamine receptor agonists, such as amitraz; (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon; or acequinocyl; or fluacrypyrim; (21) Mitochondrial complex I electron transport inhibitors, such as those from the group of METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, and tolfenpyrad; or rotenone (Derris); (22) Voltage-dependent sodium channel blockers, such as indoxacarb; or metaflumizone; (23) Acetyl-CoA carboxylase inhibitors, such as tetronic acid derivatives and tetramic acid derivatives, such as spirodiclofen, spiromesifen, and spirotetramat; (24) Mitochondrial complex IV electron transport inhibitors, for example, phosphines, such as aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide; or cyanides, such as calcium cyanide, potassium cyanide, and sodium cyanide; (25) Mitochondrial complex II electron transport inhibitors, for example, β-ketonitrile derivatives such as cyenopyrafen and cyflumetofen, and carboxanilides such as piflubumid; (28) Ryanodine receptor modulators, for example, diamides, such as chlorantraniliprole, cyantraniliprole, and flubendiamide;Further active compounds, such as Afidopiropen, Afoxolaner, Azadirachtin, Benclotiaz, Benzoximate, Bifenazate, Brofuranilide, Bromopropylate, Chinomethionate, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxapride, Cyhalodiamide, Dichloromezothiaz, Dicofol, ε-Metofluthrin, ε-Momfluthrin Momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxamethamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, paichongding, Pyridalyl, Pyrifluquinazone, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Thioxazaphen, Thiofluoximate, Triflumezopyrim, and Iodomethane; and Bacillus firmus. firmus) based preparations (I-1582, BioNeem, Votivo), as well as the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from EP2647626) (CAS-1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-Dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide (known from WO2013 / 050317A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO2013 / 162715A2, WO2013 / 162716A2, US2014 / 0213448A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN101337937A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN103109816A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2012 / 034403A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO2011 / 085575A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN101715774A) (CAS 1232543-85-9; 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from CN103524422A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN102391261A) (CAS 1370358-69-2;6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-Triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US2014 / 0275503A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (known from WO2007040280A1 and WO2007040282A1) (CAS 934001-66-8), and N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide (known from WO2015 / 058021A1 and WO2015 / 058028A1) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN103265527A) (CAS1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (WO2013 / 115391A 1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 066780 A1 and WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO2014 / 187846A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-carbonic acid ethyl ester (known from WO2010 / 066780A1 and WO2011151146A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (DE 363987 7A1, known from WO2012029672A1) (CAS1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from WO2016005276A1) (CAS1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide, (CAS1702305-40-5), 3-endo-3-[2-propionyl]- ... [5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO2011 / 105506A1 and WO2016 / 133011A1) (CAS1332838-17-1).

[0194] Examples of safeners which may be mixed with the compounds of formula (I) and compositions containing them are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0195] Examples of herbicides which may be mixed with the compounds of formula (I) and compositions containing them are:

[0196] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, sulfamine Ammonium acetate, ancymidol, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamid, benazolin-ethyl, benfluralin, benfresate, bensulfuron, bensulfuron-methyl, bensulide, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, viranaphos, viranaphos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil-butylate -potassium, -heptanoate, and -octanoate, busoxinone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim , chlorotoluron, chlortal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, chloransulam, chloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, ciprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, -isooctyl, -potassium and -sodium, Dimron (Dimron), Dalapon, Dazomet, n-decanol, Desmedipham, Desme Torin, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, dif Lufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, etiodin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxyfen-ethyl Xysulfuron, etobenzanide, F-9600, F-5331, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulf flucloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flometuron, flurenol, flurenol-butyl, dimethylammonium and methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, isopropylammonium, diammonium, dimethylammonium, potassium, sodium sodium and -trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl isopropyl phosphoramidothioate, haloxifene, haloxifene-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e., (2,1-(dimethoxyphosphoryl)-ethyl 4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, - Potassium, and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium , -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrisulfuron risulfuron), methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron esters, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-Dichlorophenyl)methanone, nebron, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentanochlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretila Chlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, Pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, li Musulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramezone, tralkoxydim, triaf These include benzophenone, trialate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, and ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, as well as the following compounds: [ka]

[0197] Examples of plant growth regulators include:

[0198] Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium and -mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole 3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0199] Methods and Uses The compounds of formula (I) and compositions containing them have potent microbicidal activity.

[0200] They can be used to control undesirable microorganisms, such as undesirable fungi and bacteria. They can be particularly useful for crop protection (controlling microorganisms that cause plant diseases) or material (e.g., industrial materials, wood, stored goods) protection, as described in more detail herein below. More specifically, the compounds of formula (I) and compositions containing them can be used to protect seeds, germinating seeds, emerging seedlings, plants, plant parts, fruits, harvested products, and / or the soil in which plants grow from undesirable microorganisms.

[0201] As used herein, control or controlling includes protective, curative, and eradication treatments of undesirable microorganisms. The undesirable microorganisms may be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically, plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes, or plant pathogenic fungi. As described in more detail herein below, these plant pathogenic microorganisms are the causative agents of a wide spectrum of plant diseases.

[0202] More specifically, the compounds of formula (I) and compositions comprising them can be used as fungicides. In the context of this specification, the term "fungicide" can be used in crop protection to control unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, and / or to control Oomycetes, more preferably Basidiomycetes (which cause rust).

[0203] The present invention also relates to a method for controlling undesirable microorganisms, such as phytopathogenic fungi, oomycetes and bacteria, which method comprises applying at least one compound of formula (I) or at least one composition comprising same to the microorganisms and / or their habitat (to plants, plant parts, seeds, fruits or the soil in which the plants grow).

[0204] Typically, when the compounds and compositions of the present invention are used in a method for curative or protective control of plant pathogenic fungi and / or plant pathogenic oomycetes, an effective and plant-compatible amount is applied to plants, plant parts, fruits, seeds, or the soil or substrate on which the plants grow. Suitable substrates that can be used to cultivate plants include inorganic substrates such as mineral wool, especially stone wool, perlite, sand, or gravel; organic substrates such as peat, pine bark, or sawdust; and petroleum-based substrates such as polymeric foam or plastic beads. An effective and plant-compatible amount means an amount sufficient to control or destroy fungi that are present in or likely to be found in cultivated land, without causing noticeable phytotoxicity symptoms in the crop. Such an amount can vary within a wide range depending on the fungi to be controlled, the type of crop, the stage of crop development, climatic conditions, and the specific compound or composition of the present invention used. This amount can be determined by systematic field testing, which is within the capabilities of those skilled in the art.

[0205] Plants and plant parts The compounds of formula (I) and compositions containing them can be applied to any plant or plant part.

[0206] Plants refer to all plants and plant groups, including desirable and undesirable wild plants or crop plants (such as naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods, or by biotechnology and genetic engineering methods or a combination of these methods, such as genetically modified plants (GMOs or transgenic plants) and plant cultivars that can and cannot be protected by plant breeders' rights.

[0207] Plant parts are understood to mean all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which are leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes, etc. Plant parts also include harvested material and vegetative and reproductive propagation, such as seedlings, tubers, rhizomes, cuttings and seeds.

[0208] Plants that can be treated according to the method of the invention include cotton, flax, grapevines, fruits, vegetables, for example Rosaceae species (for example pome fruits, such as apples and pears, as well as stone fruits, such as apricots, cherry trees, almonds and peaches, and small fruit trees, such as strawberries), Ribesioidae species, Juglandaceae species, Betulaceae species, Anacardiaceae species, Fagaceae species, Moraceae species, Oleaceae species, Actinidaceae species, Lauraceae species, Musaceae species. sp.) (e.g. banana trees and plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g. lemon, orange and grapefruit), Solanaceae sp. (e.g. tomato), Liliaceae sp., Asteraceae sp. (e.g. lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g. cucumber), Alliaceae sp.) (e.g., leek, onion), Papilionaceae sp. (e.g., pea); staple crop plants, e.g., Gramineae sp. (e.g., maize, grass, cereals such as wheat, rye, rice, barley, oats, millet, and triticale), Asteraceae sp. (e.g., sunflower), Brassicaceae sp.) (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radish, and rapeseed, mustard, horseradish, and cress), Fabasae species (e.g., beans, peanuts), Papilionaceae species (e.g., soybean), Solanaceae species (e.g., potato), Chenopodiaceae species (e.g., sugar beet, fodder beet, Swiss chard, beetroot); useful and ornamental plants for gardens and forests; and genetically modified varieties of each of these plants.

[0209] In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods such as crossing or protoplast fusion, and parts thereof, are treated according to the methods of the present invention.

[0210] In some other preferred embodiments, transgenic plants and plant cultivars (genetically modified organisms), obtained by genetic engineering methods, where appropriate in combination with conventional methods, and parts thereof, are treated according to the methods of the present invention. More preferably, plants of plant cultivars that are commercially available or in use are treated according to the present invention. Plant cultivars should be understood to mean plants that have novel properties ("traits") and that have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These can be cultivars, mutants, biotypes or genotypes.

[0211] The method according to the invention can be used for the treatment of genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome.

[0212] The term "heterologous gene" essentially refers to a gene that is provided or assembled outside the plant and that, when introduced into the nuclear, chloroplastic or mitochondrial genome, confers new or improved agronomic or other properties on the transformed plant by expressing a protein or polypeptide of interest or by reducing or silencing other genes present in the plant (for example, using antisense, co-suppression, RNA interference - RNAi - or microRNA - miRNA - technologies). A heterologous gene present in the genome is also called a transgene. A transgene defined by its specific location in the plant genome is called a transformation or transgenic event.

[0213] Plants and plant cultivars which can be treated in the above manner include all plants which possess genetic material that confers on these plants particularly advantageous and useful traits (whether or not obtained by breeding and / or biotechnological means).

[0214] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are resistant to one or more biotic stresses, i.e., that exhibit better protection against harmful animals and microorganisms, such as nematodes, insects, mites, plant pathogens, bacteria, viruses and / or viroids.

[0215] Plants and plant cultivars that can be treated by the methods disclosed above include plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can be, for example, drought, cold exposure, heat exposure, osmotic stress, flooding, elevated soil salt concentrations, increased mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, shade avoidance, and the like.

[0216] Plants and plant cultivars that can be treated by the methods disclosed above include plants characterized by improved harvest characteristics. For example, improved plant physiology, growth, and development, such as water use efficiency, water retention efficiency, improved nitrogen utilization, improved carbon assimilation, improved photosynthesis, increased germination efficiency, and accelerated maturation, can result in increased yield in the plant. Yield can also be affected by improved plant architecture (under stress and non-stress conditions), including, but not limited to, early flowering, controlled flowering for hybrid seed production, seedling vigor, plant size, internode number and spacing, root growth, seed size, fruit size, pod size, number of pods and ears, number of seeds per pod or ear, seed mass, enhanced seed filling, reduced seed dehiscence, reduced reduced pod dehiscence, and lodging resistance. Additional yield-related traits include seed composition, such as carbohydrate content and composition (e.g., cotton or starch), protein content, oil content and composition, nutritional value, reduced non-nutritional compounds, improved processability, and improved storage stability.

[0217] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are hybrids that already express heterosis or hybrid vigor characteristics that result in increased yield, improved vigor, improved health, and resistance to biotic and abiotic stresses.

[0218] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above are herbicide-tolerant plants, i.e., plants that have been made tolerant to one or more selected herbicides. Such plants can be obtained by transformation or by selection of plants containing mutations that confer such herbicide tolerance.

[0219] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include insect-resistant transgenic plants, i.e., plants and plant cultivars that have been made resistant to attack by certain target insects. Such plants can be obtained by transformation or by selection of plants containing mutations that confer such insect resistance.

[0220] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are tolerant to abiotic stresses. Such plants can be obtained by transformation or by selecting plants containing mutations that confer such stress resistance.

[0221] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that exhibit altered yield quantity, quality and / or storage stability and / or altered properties of specific components of the yield.

[0222] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars with altered fiber characteristics, such as cotton plants, etc. Such plants can be obtained by transformation and by selection of plants containing mutations that confer such altered fiber characteristics.

[0223] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars with altered oil profile characteristics, such as rapeseed or related Brassica plants. Such plants can be obtained by transformation or by selection of plants containing mutations that confer such altered oil profile characteristics.

[0224] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars with altered seed shattering characteristics, such as rapeseed or related Brassica plants. Such plants can be obtained by transformation or by selection of plants containing mutations that confer such altered seed shattering characteristics, and include plants with delayed or reduced seed shattering, such as rapeseed plants.

[0225] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars with altered post-translational protein modification patterns, such as tobacco plants.

[0226] Pathogens and diseases The methods disclosed above can be used to control microorganisms, particularly phytopathogenic microorganisms, such as phytopathogenic fungi that cause diseases such as those described below.

[0227] Diseases caused by powdery mildew pathogens, such as Blumeria species (e.g., Blumeria graminis), Podosphaera species (e.g., Podosphaera leucotricha), Sphaerotheca species (e.g., Sphaerotheca fuliginea), and Uncinula species (e.g., Uncinula necator); Diseases caused by rust pathogens, such as Gymnosporangium species (e.g. Gymnosporangium sabinae), Hemileia species (e.g. Hemileia vastatrix), Phakopsora species (e.g. Phakopsora pachyrhizi and Phakopsora meibomiae), Puccinia species (e.g. Puccinia recondita, Puccinia graminis or Puccinia striiformis), striiformis), Uromyces species (e.g., Uromyces appendiculatus); Diseases caused by pathogens of the Oomycetes group, such as Albugo species (e.g., Albugo candida), Bremia species (e.g., Bremia lactucae), Peronospora species (e.g., Peronospora pisi or P. brassicae), Phytophthora species (e.g., Phytophthora infestans), Plasmopara species (e.g., Plasmopara viticola), Pseudoperonospora species (e.g., Pseudoperonospora humilis), humuli or Pseudoperonospora cubensis), Pythium species (e.g., Pythium ultimum); Leaf blotch diseases and leaf wilt diseases caused by, for example, Alternaria species (e.g., Alternaria solani), Cercospora species (e.g., Cercospora beticola), Cladiosporum species (e.g., Cladiosporium cucumerinum), Cochliobolus species (e.g., Cochliobolus sativus (conidiotype: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus miyabeanus), Colletotrichum species (e.g., Colletotrichum lindemuthanium), Cycloconium species (e.g., Cycloconium oleaginum), Diaporthe species (e.g., Diaporthe citri), Elsinoe species (e.g., Elsinoe fawcettii), Gloeosporium species (e.g., Gloeosporium laeticolor), Glomerella species (e.g., Glomerella cingulate), cingulate), Guignardia species (e.g., Guignardia bidwelli), Leptosphaeria species (e.g., Leptosphaeria maculans), Magnaporthe species (e.g., Magnaporthe grisea),grisea), Microdochium species (e.g., Microdochium nivale), Mycosphaerella species (e.g., Mycosphaerella graminicola, Mycosphaerella arachidicola, or Mycosphaerella fijiensis), Phaeosphaeria species (e.g., Phaeosphaeria nodorum), Pyrenophora species (e.g., Pyrenophora teres or Pyrenophora tritici repentis), repentis), Ramularia species (e.g., Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g., Rhynchosporium secalis), Septoria species (e.g., Septoria apii or Septoria lycopersici), Stagonospora species (e.g., Stagonospora nodorum), Typhula species (e.g., Typhula incarnate), Venturia species (e.g., Venturia inaequalis); Root and stem diseases caused by, for example, Corticium species (e.g., Corticium graminearum), Fusarium species (e.g., Fusarium oxysporum), Gaeumannomyces species (e.g., Gaeumannomyces graminis), Plasmodiophora species (e.g., Plasmodiophora brassicae), Rhizoctonia species (e.g., Rhizoctonia solani), Sarocladium species (e.g., Sarocladium oryzae), oryzae), Sclerotium species (e.g., Sclerotium oryzae), Tapesia species (e.g., Tapesia acuformis), Thielaviopsis species (e.g., Thielaviopsis basicola); Diseases of ears and panicles (such as corn cobs) caused by, for example, Alternaria spp. (e.g., Alternaria spp.), Aspergillus spp. (e.g., Aspergillus flavus), Cladosporium spp. (e.g., Cladosporium cladosporioides), Claviceps spp. (e.g., Claviceps purpurea), Fusarium spp. (e.g., Fusarium culmorum), Gibberella spp. (e.g., Gibberella zeae), zeae), Monographella species (e.g., Monographella nivalis), Stagnospora species (e.g., Stagnospora nodorum); Diseases caused by the following smut fungi, such as Sphacelotheca species (e.g. Sphacelotheca reiliana), Tilletia species (e.g. Tilletia caries or Tilletia controversa), Urocystis species (e.g. Urocystis occulta), Ustilago species (e.g. Ustilago nuda); Fruit rot caused by Aspergillus species (e.g., Aspergillus flavus), Botrytis species (e.g., Botrytis cinerea), Penicillium species (e.g., Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g., Rhizopus stolonifer), Sclerotinia species (e.g., Sclerotinia sclerotiorum), Verticilium species (e.g., Verticilium alboatrum); Seed- and soil-borne rot and blight diseases, and seedling diseases caused by, for example, Alternaria species (e.g., Alternaria brassicicola), Aphanomyces species (e.g., Aphanomyces euteiches), Ascochyta species (e.g., Ascochyta lentis), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium herbarum), Cochliobolus species (e.g., Cochliobolus sativus), sativus (conidiotype: Drechslera, Bipolaris synonym: Helminthosporium), Colletotrichum species (e.g., Colletotrichum coccodes), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Macrohomina species (e.g., Macrohomina phaseolina), Microdochium species (e.g., Microdochium nivale), Monographella species (e.g., Monographella nivalis), nivalis), Penicillium species (e.g., Penicillium expansum), Phoma species (e.g., Phoma lingam), Phomopsis species (e.g., Phomopsis sojae),sojae), Phytophthora species (e.g., Phytophthora cactorum), Pyrenophora species (e.g., Pyrenophora graminea), Pyricularia species (e.g., Pyricularia oryzae), Pythium species (e.g., Pythium ultimum), Rhizoctonia species (e.g., Rhizoctonia solani), Rhizopus species (e.g., Rhizopus oryzae), Sclerotium species (e.g., Sclerotium rolfsii), rolfsii), Septoria species (e.g., Septoria nodorum), Typhula species (e.g., Typhula incarnate), Verticillium species (e.g., Verticillium dahlia); Cancer, gall disease and witches' broom caused by, for example, Nectria species (e.g., Nectria galligena); wilt diseases caused by, for example, Monilinia species (e.g., Monilinia laxa); Deformations of leaves, flowers and fruits caused by, for example, Exobasidium species (e.g., Exobasidium vexans), Taphrina species (e.g., Taphrina deformans); Degenerative diseases in wood plants caused by, for example, Esca species (e.g., Phaemoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (e.g., Ganoderma boninense); Flower and seed diseases caused by, for example, Botrytis species (e.g., Botrytis cinerea); Diseases of plant tubers caused by, for example, Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani); Diseases caused by bacterial pathogens such as Xanthomonas species (e.g., Xanthomonas campestris pv. Oryzae), Pseudomonas species (e.g., Pseudomonas syringae pv. Lachrymans), and Erwinia species (e.g., Erwinia amylovora).

[0228] Seed treatment Methods for controlling unwanted microorganisms can be used to protect seeds from plant pathogenic microorganisms such as fungi.

[0229] The term seeds as used herein includes dormant seeds, primed seeds, germinated seeds and seeds with germinated roots and leaves.

[0230] Therefore, the present invention also relates to a method for protecting seeds and / or crops from unwanted microorganisms such as bacteria or fungi, which method comprises treating the seeds with one or more compounds of formula (I) or compositions comprising same. The treatment of seeds with compounds of formula (I) or compositions comprising same not only protects the seeds from phytopathogenic microorganisms, but also the germinating plants, emerged seedlings and emerged plants.

[0231] Seed treatment can be carried out before sowing, at the time of sowing or immediately thereafter.

[0232] When seed treatment is carried out before sowing (for example, so-called seed application), the seed treatment can be carried out as follows: seeds can be placed in a mixer together with a desired amount of the compound of formula (I) and the composition comprising it (either directly or after dilution), and the seeds and the compound of formula (I) and the composition comprising it are mixed until a uniform distribution is achieved on the seed surface.If appropriate, the seeds can then be dried.

[0233] The present invention also relates to seeds treated with one or more compounds of formula (I) or compositions containing the same.As mentioned above, the use of treated seeds can not only protect seeds before and after sowing from undesirable microorganisms such as plant pathogenic fungi, but also protect the germinated plants and young seedlings that germinate from the treated seeds.Most of the damage caused by pests to crop plants is caused by seed infection before sowing or infection after plant germination.This stage is particularly important because the roots and shoots of growing plants are particularly sensitive, and even small damage can lead to plant death.

[0234] The present invention therefore also relates to a method for protecting seeds, germinating plants and emerging seedlings, and more generally for protecting crops against phytopathogenic microorganisms, which method comprises using seeds treated with one or more compounds of formula (I) or a composition comprising same.

[0235] Preferably, the seeds are treated in a stable state that prevents damage during treatment. Generally, the seeds can be treated at any time between harvest and immediately after sowing. Generally, seeds that have been separated from the plant and are free of the cob, husk, petiole, husk, hair, or flesh are used. For example, seeds that have been harvested, cleaned, and dried to a moisture content of less than 15% by weight can be used. Alternatively, seeds that have been dried, for example, treated with water, and then re-dried, or seeds that have been primed, or seeds that have been stored under primed conditions, or germinated seeds, or seeds that have been sown in nursery trays, nursery tape, or nursery paper can be used.

[0236] The amount of the compound of formula (I) or a composition containing it to be applied to seeds is typically such that the germination of the seeds is not impaired or the plants resulting from the seeds are not damaged. This should be ensured, especially when the active ingredient is thought to exhibit phytotoxic effects at a particular application rate. In order to achieve optimal seed and germinating plant protection using the minimum amount of the compound of formula (I) or a composition containing it, the specific phenotype of the transgenic plant should also be taken into consideration when determining the amount of the compound of formula (I) or a composition containing it to be applied to seeds.

[0237] As indicated above, the compound of formula (I) can be applied directly to seeds, i.e., without using other components or dilution, or a composition containing the compound of formula (I) can be applied to seeds. Preferably, the composition is applied to seeds in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, dusts, foams, slurries, or combinations with other seed coating compositions, such as film-forming materials, pelleted materials, fine iron or other metal powders, granules, inactivated seed coating materials, and even ULV formulations. The formulations can be ready-to-use formulations or concentrates that need to be diluted before use.

[0238] These formulations are prepared in a known manner, for example by mixing the active ingredient or mixtures thereof with conventional additives, such as conventional thickeners and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

[0239] These formulations are prepared in known manner by mixing the active ingredient or active ingredient combinations with conventional additives, such as conventional thickeners and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

[0240] Useful pigments that may be present in seed dressing formulations are all pigments commonly used for such purposes. Either sparingly water-soluble or water-soluble pigments can be used. Examples include the pigments known as Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1. Useful wetting agents that may be present in seed dressing formulations are all substances that promote wetting and are conventionally used in formulating active pesticide ingredients. Alkyl naphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonate, are preferably used. Useful dispersants and / or emulsifiers that may be present in seed dressing formulations are all nonionic, anionic, and cationic dispersants conventionally used in formulating active pesticide ingredients. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are preferably used. Useful nonionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants include, in particular, lignosulfonates, polyacrylates, and aryl sulfonate / formaldehyde condensates. Antifoaming agents that may be present in seed dressing formulations are all foam-suppressing substances conventionally used in formulating active pesticide ingredients. Silicone antifoams and magnesium stearate are preferred. Preservatives that may be present in seed dressing formulations are all substances that can be used for such purposes in pesticide compositions. Examples include dichlorophen and benzyl alcohol hemiformal. Secondary thickeners that may be present in seed dressing formulations are all substances that can be used for such purposes in pesticide compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clay, and finely divided silica. Adhesives that may be present in the seed dressing formulations are all common binders that can be used in seed dressing products, preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0241] The compounds of formula (I) and compositions containing them are suitable for protecting the seeds of any plant variety used in agriculture, greenhouses, forestry or horticulture.In particular, the seeds are those of cereals (such as wheat, barley, rye, millet, triticale and oats), rapeseed, corn, cotton, soybean, rice, potato, sunflower, common bean, coffee, pea, beet (such as sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onion and lettuce), turf and ornamental plants.Particularly important is the treatment of wheat, soybean, rapeseed, corn and rice seeds.

[0242] The compounds of formula (I) or compositions containing them can be used to treat transgenic seeds, especially seeds of plants that express proteins that act against pests, herbicide damage or abiotic stress, thereby increasing the protective effect. Synergistic effects may occur due to interactions with substances formed by expression.

[0243] nematodes In the context of the present invention, the term "nematodes" includes all species of the phylum Nematoda, and here particularly includes species that act as parasites of plants or fungi (e.g., members of the orders Aphelenchida, Meloidogyne, Tylenchida, etc.) or as parasites of humans and animals (e.g., members of the orders Trichinellida, Tylenchida, Rhabditina, and Spirurida), causing damage in or on these organisms, and also includes other parasitic helminths.

[0244] Nematicides in crop protection, as described herein, are capable of controlling nematodes.

[0245] The term "controlling nematodes" means killing nematodes, or preventing or retarding the development or growth of nematodes, or preventing or retarding the penetration or sap of nematodes into or from plant tissue.

[0246] The efficacy of the compound is determined by comparing the mortality rate of nematodes, gall formation, cyst formation, nematode density per unit volume of soil, nematode density per root, number of nematode eggs per unit volume of soil, and nematode motility between plants or plant parts or treated soil treated with a compound of formula (I) and untreated plants or plant parts or untreated soil (100%). Preferably, a 25-50% reduction is achieved, particularly preferably a 51-79% reduction, and very particularly preferably complete killing or complete prevention of nematode development and growth (80%-100% reduction) is achieved compared to untreated plants, plant parts, or untreated soil. The term "control of nematodes" as used herein also refers to the control of nematode proliferation (cyst and / or egg development). Similarly, the compounds of formula (I) can be used to maintain the health of plants or animals and they can be used therapeutically, prophylactically or systemically to control nematodes.

[0247] Those skilled in the art know how to determine nematode mortality, gall formation, cyst formation, nematode density per unit volume of soil, nematode density per root, number of nematode eggs per unit volume of soil, and nematode motility.

[0248] The use of the compounds of formula (I) can maintain the plants in a healthy state, and also includes reducing damage caused by nematodes and increasing yields.

[0249] In the context of the present invention, the term "nematodes" refers to plant nematodes, including all nematodes that cause damage to plants. Plant nematodes include plant-parasitic nematodes and soil-borne nematodes. Plant-parasitic nematodes may include ectoparasites such as Xiphinema spp., Longidorus spp. and Trichodorus spp.; hemiparasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp. and Scutellonema spp.; non-migratory parasites such as Heterodera spp., Globodera spp. and Meloidogyne spp. spp.); and, furthermore, stem and leaf endoparasites, such as Ditylenchus spp., Aphelenchoides spp. and Hirschmaniella spp. Particularly harmful root-parasitic soil nematodes are, for example, cyst-forming nematodes of the Heterodera or Globodera genera and / or root-knot nematodes of the Meloidogyne genus. Harmful species of these genera include, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida, and Globodera rostochiensis (potato cyst nematode); these species are effectively controlled with the compounds described herein. However, the use of the compounds described herein is in no way limited to these genera or species, and also extends to other nematodes as well.

[0250] Plant nematodes that may be mentioned include, for example, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragariae, as well as stem and leaf endoparasites Aphelenchoides spp., Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus. eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp., Criconemoides ferniae ferniae, Criconemoides onoense, Criconemoides ornatum, and Criconemoides spp.), Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and stem and leaf endoparasites, Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (=Heterodera pallida), Globodera rostochiensis (potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera virginia virginia), as well as the non-migratory cyst-forming parasites Globodera spp., Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus, and Helicotylenchus spp.), Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae, as well as non-migratory cyst-forming nematodes, Heterodera spp.), Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata, and stem and leaf endoparasites, Hirschmaniella spp., Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus paralobustus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola, and ectoparasites, Longidorus spp.), Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi, and non-migratory parasites, Meloidogyne spp., Meloinema spp.), Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres, and Paratrichodorus spp., Paratrichodorus hamatus, Paratylenchus minutus, Paratylenchus projectus, and Paratylenchus spp.), Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae, and migratory endoparasites, Pratylenchus spp.), Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Rad. opholus similis, migratory endoparasites, Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyurum brachyurum, Scutellonema bradys, Scutellonema clathricaudatum, and migratory endoparasites, Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus. sparsus, and ectoparasites, Trichodorus spp.), Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, and Tylenchorhynchus spp., Tylenchulus semipennetrans semipenetrans and hemiparasites, Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and ectoparasites, Xiphinema spp.

[0251] Nematodes which the compounds of formula (I) can be used to control include nematodes of the genus Meloidogyne, such as Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla and Meloidogyne arenaria; nematodes of the genus Ditylenchus, such as Ditylenchus destructor and Ditylenchus dipsaci; nematodes of the genus Pratylenchus, such as Pratylenchus penetrans, Pratylenchus fallax and Pratylenchus coffeae, Pratylenchus loosi, and Pratylenchus vulnus; nematodes of the genus Globodera, for example, the yellow potato cyst nematode (Globodera rostochiensis) and the white potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera, for example, the soybean cyst nematode (Heterodera glycines) and the beet cyst eelworm (Heterodera schachtii); nematodes of the genus Aphelenchoides, for example, the rice root nematode (Aphelenchoides besseyi) and the chrysanthemum nematode (Aphelenchoides ritzemabosi and strawberry nematode (Aphelenchoides fragariae); Nematodes of the genus Aphelenchus, for example the fungivorous nematode (Aphelenchus avenae);Nematodes of the genus Radopholus, such as the burrowing nematode (Radopholus similis); nematodes of the genus Tylenchulus, such as the citrus root nematode (Tylenchulus semipenetrans); nematodes of the genus Rotylenchulus, such as the false nematode (Rotylenchulus reniformis); nematodes living in trees, such as the pinewood nematode (Bursaphelenchus xylophilus) and the red ring nematode (Bursaphelenchus cocophilus); etc.;

[0252] Plants for which the compounds of formula (I) can be used to protect include, for example, cereals (e.g., rice, barley, wheat, rye, oats, maize, etc.), legumes (e.g., soybean, adzuki bean, broad bean, pea, peanut, etc.), fruit trees / fruits (e.g., apple, citrus, pear, grapevine, peach, plum, cherry, walnut, almond, banana, strawberry, etc.), vegetable species (e.g., cabbage, tomato, spinach, broccoli, lettuce, tuna, etc.), and the like. onions, leeks, peppers, etc.), root vegetables (carrots, potatoes, sweet potatoes, radishes, lotus roots, turnips, etc.), plants for industrial use (cotton, hemp, paper mulberry, mitsumata, rapeseed, beets, hops, sugarcane, sugar beets, olives, rubber, palm, coffee, tobacco, tea, etc.), cucurbits (pumpkins, cucumbers, watermelons, melons, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf grasses (mascarene grass, bentgrass, etc.), aromatic plants (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), and flowers (chrysanthemums, roses, orchids, etc.).

[0253] The compounds of formula (I) are particularly suitable for controlling nematodes in coffee, in particular Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp., and also Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp., and Scutellonema spp. spp.).

[0254] The compounds of formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci, and also Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus clenatus. crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Paratrichodorus terresteres, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae, and Meloinema spp.

[0255] The compounds of formula (I) are particularly suitable for controlling nematodes of tomatoes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans, and also Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorus minor, Meloidogyne exigua, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus, and Rotylenchulus reniformis.

[0256] The compounds of formula (I) are particularly suitable for controlling nematodes of Cucurbitaceae plants, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei.

[0257] The compounds of formula (I) are particularly suitable for controlling cotton nematodes, in particular Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

[0258] The compounds of formula (I) are particularly suitable for controlling nematodes in corn, in particular Belonolaimus longicaudatus, Paratrichodorus minor, and also Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannellus, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannellus, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannellus, (Belonolaimus gracilis), Belonolaimus nortoni, (Belonolaimus gracilis), Belonolaimus gracilis ... breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimus galeatusgaleatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus heterocephalus, Criconemella ornata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici tritici, Aphelenchoides arachidis, Scutellonema brachyurum, and Subanguina radiciola.

[0259] The compounds of formula (I) are particularly suitable for controlling soybean nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus, and also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus. neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus galeatus, and Rotylenchulus reniformis.

[0260] The compounds of formula (I) are particularly suitable for controlling nematodes on tobacco, in particular Meloidogyne incognita, Meloidogyne javanica, and also Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchus brunnus. vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp.), Xiphinema americanum, Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp.), and Tetylenchus nicotianae.

[0261] The compounds of formula (I) are particularly suitable for controlling citrus nematodes, in particular Pratylenchus coffeae, and also Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne nigricans ... javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis, and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata, and Tylenchulus semipenetrans.

[0262] The compounds of formula (I) are particularly suitable for controlling nematodes on bananas, in particular Pratylenchus coffeae, Radopholus similis, and also Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp.

[0263] The compounds of formula (I) are particularly suitable for controlling pineapple nematodes, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi, Meloidogyne spp., Rotylenchulus reniformis, and also Longidorus elongatus, Longidorus laevicapitatus, Trichodorus primitivus, Trichodorus minoru. minor), Heterodera spp.), Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoense onoense, and Criconemoides ornatum.

[0264] The compounds of formula (I) are particularly suitable for controlling vine nematodes, in particular Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index, and also Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus. brachyurus, Pratylenchus thornei, and Tylenchulus semipenetrans.

[0265] The compounds of formula (I) are particularly suitable for controlling nematodes of tree crops - pome fruit, in particular Pratylenchus penetrans and also Pratylenchus vulnus, Longidorus elongatus, Meloidogyne incognita and Meloidogyne hapla.

[0266] The compounds of formula (I) are particularly suitable for controlling nematodes of tree crops - stone fruit, in particular: Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax, and also Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri. scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyurum, and Hoplolaimus galeatus.

[0267] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops, sugarcane and rice, in particular Trichodorus spp., Criconemella spp., and also Pratylenchus spp., Paratrichodorus spp., Meloidogyne spp., Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp., Heterodera spp., Xiphinema spp., and Cacopaurus pestis. pestis).

[0268] application The compounds of formula (I) may be applied as such or in the form of, for example, ready-to-use solutions, emulsions, water- or oil-based suspensions, dusts, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcast, suspoemulsion formulations, natural products impregnated with a compound of formula (I), synthetic materials impregnated with a compound of formula (I), fertilizers or microcapsules in polymeric materials.

[0269] Application is carried out in the conventional manner, for example by watering, spraying, spraying, broadcasting, dusting, foaming, spreading-on, etc. The compounds of formula (I) can also be applied by the micro-application method via drip irrigation or drench treatment, by infloor application, or by injecting them into the trunk or stem in the soil. The compounds of formula (I) can also be applied by wound seals, paints, or other wound coverings.

[0270] The effective and plant-compatible amount of a compound of formula (I) applied to a plant, plant part, fruit, seed or soil depends on various factors such as the compound / composition used, the target of treatment (plant, plant part, fruit, seed or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (curative and protective), the type of microorganism, the developmental stage of the microorganism, the susceptibility of the microorganism, the stage of crop growth and the environmental conditions.

[0271] When the compounds of formula (I) are used as fungicides, their application rates can vary within a relatively wide range depending on the type of application. For the treatment of plant parts (e.g., leaves), the application rate can be in the range of 0.1 to 10,000 g / ha, preferably 10 to 1,000 g / ha, and more preferably 50 to 300 g / ha. (When applied by irrigation or dripping, especially when an inert substrate such as rock wool or perlite is used, the application rate can be further reduced.) For seed treatment, the application rate can be in the range of 0.1 to 200 g / 100 kg of seeds, preferably 1 to 150 g / 100 kg of seeds, more preferably 2.5 to 25 g / 100 kg of seeds, and even more preferably 2.5 to 12.5 g / 100 kg of seeds. For soil treatment, the application rate can be in the range of 0.1 to 10,000 g / ha, preferably 1 to 5,000 g / ha.

[0272] These application rates are merely examples and are not intended to limit the scope of the invention.

[0273] material protection The compounds and compositions of the present invention may also be used in the protection of materials, particularly industrial materials against attack and destruction by unwanted microorganisms.

[0274] Additionally, the compounds and compositions of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

[0275] In the context of the present invention, industrial materials are understood to mean inanimate materials manufactured for industrial use. For example, industrial materials to be protected from microbial deterioration or destruction can be adhesives, glues, paper, wallpaper and board / cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants, and other materials that can be infected by or destroyed by microorganisms. Parts of manufacturing plants and buildings that can be damaged by microbial growth, such as cooling water circuits, cooling and heating systems, and exhaust and air conditioning equipment, can also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants, and heat transfer fluids, more preferably wood.

[0276] The compounds and compositions of the present invention can prevent harmful effects such as corrosion, decay, discolouration, bleaching or mould formation.

[0277] In the treatment of wood, the compounds and compositions of the present invention can also be used against fungal diseases that tend to develop on or within the timber.

[0278] Timber refers to all types of wood species and all types of construction products of this wood, such as solid wood, high-density wood, plywood, and veneer. Furthermore, the compounds and compositions of the present invention can be used to protect objects that come into contact with salt water or brackish water, in particular ship hulls, screens, nets, buildings, mooring rigging, and signaling systems, from fouling.

[0279] The compounds and compositions of the present invention can also be used to protect stored goods. "Stored goods" is understood to mean natural substances of plant or animal origin or processed products thereof of natural origin that are desired to be protected for a long period of time. For example, stored goods of plant origin, such as plants or plant parts, for example, stems, leaves, tubers, seeds, fruits, and grains, can be protected either freshly harvested or after processing by (pre)drying, moistening, crushing, grinding, pressing, or roasting. Stored goods also include timber, both in the form of raw timber such as building timber, utility poles, and fences, and in the form of finished products such as furniture. Stored goods of animal origin are, for example, animal hides, leather, fur, and hair. The compounds and compositions of the present invention can prevent adverse effects such as decay, deterioration, discoloration, fading, or mold formation.

[0280] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime molds. The compounds and compositions of the present invention preferably act against fungi, particularly molds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Fungi Imperfecti and Zygomycetes), as well as against slime molds and algae. Examples include microorganisms of the following genera: Alternaria, for example, Alternaria tenuis; Aspergillus, for example, Aspergillus niger; Chaetomium, for example, Chaetomium globosum; Coniophora, for example, Coniophora puetana; Lentinus, for example, Lentinus tigrinus; Penicillium, for example, Penicillium glaucum; Polyporus, for example, Polyporus versicolor. versicolor); Aureobasidium, for example, Aureobasidium pullulans; Sclerophoma, for example, Sclerophoma pityophila; Trichoderma, for example, Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp. spp.), Poria spp., Serpula spp.and Tyromyces species, Cladosporium species, Paecilomyces species, Mucor species, Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida species, and Saccharomyces species, such as Saccharomyces cerevisae.

[0281] Aspects of the present subject matter can be further understood in consideration of the following examples, which should not be construed as limiting the scope of the present subject matter in any way. [Example]

[0282] Manufacturing Example 1 : Ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.03) Phase 1 : Preparation of methyl 3-amino-4,5-dichlorothiophene-2-carboxylate Methyl 3-acetamido-4,5-dichlorothiophene-2-carboxylate (1.35 g, 5.04 mmol) was dissolved in a mixture of 37% (by weight) aqueous hydrochloric acid and 8.2 mL of methanol. The mixture was heated at 75°C for 3 hours. The cooled reaction mixture was treated with 30% (by weight) sodium hydroxide solution at 0°C. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 812 mg (98% pure, 70% yield) of methyl 3-amino-4,5-dichlorothiophene-2-carboxylate as a brown solid, which was used directly in the next step. LogP = 3.11. (M+H) = 226.

[0283] Phase 2 Preparation of methyl 3-bromo-4,5-dichlorothiophene-2-carboxylate (compound IIa.03) To a solution of 763 mg (3.41 mmol) of copper(II) bromide and 0.53 mL (90% purity, 3.99 mmol) of tert-butyl nitrite in 10.5 mL of dry acetonitrile was added 600 mg (88% purity, 2.33 mmol) of methyl 3-amino-4,5-dichlorothiophene-2-carboxylate in small portions at 0°C. After gas evolution, the solution was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and acidified with 1 M aqueous hydrochloric acid. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate) to give 563 mg (98% purity, 82% yield) of methyl 3-bromo-4,5-dichlorothiophene-2-carboxylate as a yellow solid. LogP = 3.99. (M+H) = 288.

[0284] Stage 3 Preparation of 3-bromo-4,5-dichlorothiophene-2-carboxylic acid (compound IIa.04) To a solution of 250 mg (0.86 mmol) of methyl 3-bromo-4,5-dichlorothiophene-2-carboxylate in 5 mL of tetrahydrofuran was added 1 mL (1.9 mmol) of 1.9 M aqueous potassium hydroxide solution dropwise. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, water, and saturated aqueous sodium bicarbonate. The organic layer was washed twice with saturated aqueous sodium bicarbonate. The combined aqueous layers were carefully acidified with 37% (by weight) aqueous hydrochloric acid at <0°C and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 219 mg (96% purity, 88% yield) of 3-bromo-4,5-dichlorothiophene-2-carboxylic acid as a white solid. LogP=2.51. (MH)=273.

[0285] Stage 4 Preparation of ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.03) In a 100 mL round-bottom flask under inert atmosphere, a solution of 2.47 g (14.6 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride in 50 mL of dichloromethane was added to a solution of 3.45 g (90% pure, 11.2 mmol) of 3-bromo-4,5-dichlorothiophene-2-carboxylic acid and 8.43 mL (48.3 mmol) of N,N-diisopropylethylamine in 50 mL of dichloromethane. After stirring for 5 minutes, 2.47 mg (14.6 mmol) of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) was added, and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate) to give 3.75 mg (100% purity, 86% yield) of ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate as a beige solid. LogP=3.44. (M+H)=386.

[0286] Manufacturing Example 21-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid (compound I.15) To a solution of 150 mg (0.38 mmol) of ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 2.3 mL of tetrahydrofuran was added dropwise a solution of 19.5 mg (0.81 mmol) of lithium hydroxide in 0.4 mL of water. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and water, carefully acidified to pH 1 with 1 M aqueous hydrochloric acid, and extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 131 mg (100% pure, 94% yield) of 3-bromo-4,5-dichlorothiophene-2-carboxylic acid as a white solid. LogP=2.39. (MH)=358.

[0287] Manufacturing Example 3 : Ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.03) Phase 1: Preparation of 3-amino-4,5-dichlorothiophene-2-carboxylic acid (compound XIIIa.02) To a solution of 200 mg (0.74 mmol) of methyl 3-acetamido-4,5-dichlorothiophene-2-carboxylate in 1.0 mL of methanol was added dropwise a solution of 105 mg (1.86 mmol) of potassium hydroxide in 1.0 mL of water. The reaction mixture was stirred at room temperature for 0.5 hours and then heated at 85°C for 18 hours. The resulting reaction mixture was concentrated under reduced pressure to obtain an aqueous layer, which was carefully acidified to pH 6 with 1 M aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried to afford 112 mg (96% purity, 68% yield) of the title compound as a beige solid. LogP=2.05. (M+H)=212.

[0288] Phase 2 Preparation of ethyl 1-{[(3-amino-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound XI.01) To a solution of 150 mg (0.60 mmol) of 3-amino-4,5-dichlorothiophene-2-carboxylic acid hydrochloride (1:1) and 255 mg (1.50 mmol) of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) in 4.0 mL of dichloromethane was added 0.45 mL (2.59 mmol) of N,N-diisopropylethylamine, followed by a solution of 255 mg (1.50 mmol) of 2-chloro-1,3-dimethylimidazolinium chloride in 2.0 mL of dichloromethane. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative high-performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) to afford 69 mg of the title compound (100% pure, 35% yield) as a white solid. LogP=2.77. (M+H)=323.

[0289] Stage 3 Preparation of ethyl 1-{[(3-bromo-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.03) A solution of ethyl 1-{[(3-amino-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in anhydrous acetonitrile (2 mL) was added dropwise to a solution of 53 mg (0.46 mmol) of copper(II) bromide and 61 μL (90% purity, 0.46 mmol) of tert-butyl nitrite in anhydrous acetonitrile (2 mL) at 0 °C. After gas evolution, the solution was stirred at room temperature for 72 h. The reaction mixture was diluted with dichloromethane and acidified with 1 M aqueous hydrochloric acid. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was first purified by preparative high-performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) and then by preparative supercritical fluid chromatography (gradient CO₂ / ethanol) to afford 30 mg (100% purity, 25% yield) of the title compound as a white solid. LogP = 3.48. (M+H)=386.

[0290] Production Example 4: Ethyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.01) Phase 1: Preparation of ethyl 1-{[(4-bromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound IVa.01) To a solution of 300 mg (1.33 mmol) of 4-bromo-3-fluorothiophene-2-carboxylic acid and 442 mg (2.66 mmol) of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) in 10 mL of dichloromethane was added 1.0 mL (5.73 mmol) of N,N-diisopropylethylamine, followed by a solution of 293 mg (1.73 mmol) of 2-chloro-1,3-dimethylimidazolinium chloride in 1.7 mL of dichloromethane. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate) to afford 315 mg (100% pure, 70% yield) of the title compound as a white solid. LogP=2.39. (M+H)=336.

[0291] Phase 2 Preparation of ethyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound I.01) To a stirred suspension of 100 mg (0.29 mmol) of ethyl 1-{[(4-bromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 1 mL of acetic acid in a microwave vial was added 92 μL (1.78 mmol) of bromine. The vial was sealed, and the reaction mixture was stirred at 70° C. for 2.5 hours. The reaction mixture was cooled to room temperature and added to a stirred solution of ice and sodium thiosulfate. The resulting mixture was extracted twice with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate) to give the title compound as a white solid. LogP=3.13. (M+Na)=436.

[0292] Exemplary Compounds Exemplary compounds according to the invention shown in Tables 1, 2, 3, 4, 5 and 6 were prepared analogously to the examples provided above and / or according to the general descriptions of the methods disclosed herein.

[0293] Table 1 below lists non-limiting examples of compounds according to formula (I). [ka]

[0294] Table 1: [Table 1]

[0295] TIFF0007651482000030.tif213113

[0296] TIFF0007651482000031.tif214113

[0297] TIFF0007651482000032.tif201112

[0298] TIFF0007651482000033.tif210114

[0299] TIFF0007651482000034.tif207113

[0300] TIFF0007651482000035.tif236154

[0301] Exemplary intermediates according to the present invention shown in the table below were prepared analogously to the examples provided above and / or according to the general descriptions of the methods disclosed herein.

[0302] Table 2 below shows non-limiting examples of intermediates according to formula (IIa). [ka]

[0303] Table 2: [Table 2]

[0304] Table 3 below shows non-limiting examples of intermediates according to formulae (IVa), (IVb) and (IVc). [ka]

[0305] Table 3: [Table 3]

[0306] Table 4 below shows non-limiting examples of intermediates according to formula (V). [ka]

[0307] Table 4: [Table 4]

[0308] Table 5 below shows non-limiting examples of intermediates according to formula (XI) and (XIIa). [ka]

[0309] Table 5: [Table 5]

[0310] Table 6 below shows non-limiting examples of intermediates according to formula (XIVa). [ka]

[0311] Table 6: [Table 6]

[0312] In the above table, the determination of LogP values ​​was carried out by HPLC (High Performance Liquid Chromatography) on a reversed phase column according to EEC Directive 79 / 831 Annex V.A8, using the following method:

[0313] [a] The LogP value is determined by LC-UV measurement in the acidic range using 0.1% aqueous formic acid and acetonitrile (linear gradient from 10% acetonitrile to 95% acetonitrile) as eluents.

[0314] [b] The LogP value is determined by LC-UV measurement in the neutral range using 0.001 M aqueous ammonium acetate and acetonitrile (linear gradient from 10% acetonitrile to 95% acetonitrile) as eluents.

[0315] [c] LogP values ​​are determined by LC-UV measurements in the acidic range using 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0316] If multiple LogP values ​​are available within the same method, provide all values ​​and separate them by "+".

[0317] Calibration was performed using linear alkan-2-ones (carbon numbers 3 to 16) with known LogP values ​​(LogP values ​​were determined using retention times with linear interpolation between successive alkanones). max The values ​​were calculated based on the UV spectrum from 200 nm to 400 nm. The lambda max value was determined using the UV spectrum from 200 nm to 400 nm and the peak value of the chromatographic signal.

[0318] NMR peak list Table A shows the NMR data for some of the compounds disclosed in the above table ( 1 H).

[0319] Specific Examples 1 H-NMR data is 1 The 1H-NMR peaks are listed in the form of a list. For each signal peak, the δ value and signal intensity in ppm are given in parentheses. There is a semicolon as a separator between pairs of δ value and signal intensity.

[0320] Thus, an example peak list would be of the form: δ1(Intensity 1);δ2(Intensity 2);...;δ i (strength i );..., δ n (strength n )

[0321] The intensity of sharp signals correlates with the signal height (cm) in the printed example of the NMR spectrum, showing the true relationship of signal intensities. Broad signals can indicate several peaks or signal centers and their relative intensities compared to the most intense signal in the spectrum.

[0322] To calibrate the chemical shifts for the 1H spectrum, the chemical shifts of tetramethylsilane and / or the solvent used, especially in the case of spectra measured in DMSO, are used, and therefore the NMR peak list may, but does not necessarily, include peaks for tetramethylsilane.

[0323] 1 The H-NMR peak list is 1 It is similar to a H-NMR plot and therefore typically contains all peaks listed in a conventional NMR interpretation.

[0324] Furthermore, they are 1 Like the H-NMR print, the signals of the solvent, the signals of the stereoisomers of the target compound (which are also the subject of the present invention) and / or the signals of the peaks of impurities can also be shown.

[0325] To show compound signals in the δ range of the solvent and / or water, the usual peaks of the solvent, e.g., the DMSO peak and the water peak in DMSO-D6, are 1 H-NMR peaks are listed, which usually have high average intensities.

[0326] The peaks of stereoisomers of the target compound and / or peaks of impurities usually have, on average, lower intensities than the peaks of the target compound (eg, having a purity >90%).

[0327] Such stereoisomers and / or impurities may be representative of a particular manufacturing method, and therefore their peaks may help recognize the reproducibility of our manufacturing method through a "by-product fingerprint."

[0328] If necessary, an expert who calculates the peaks of the target compounds by known methods (MestreC, ACD simulation, or even by using empirically evaluated expectation values) can separate the peaks of the target compounds using other intensity filters accordingly. This separation is not possible with conventional methods. 1 This is thought to be similar to the relevant peak selection in H-NMR interpretation.

[0329] Further details on describing NMR data using peak lists can be found in the publication "Citation of NMR Peaklist Data within Patent Applications" of the Research Disclosure Database Number 564025.

[0330] Table A :NMR peak list [Table 7]

[0331] TIFF0007651482000047.tif203170

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[0363] TIFF0007651482000079.tif163170

[0364] Biological Data - Compounds according to formula (I) Example A below demonstrates the induction of defense gene expression in Arabidopsis thaliana by compounds according to Formula (I), specifically stimulation of the salicylic acid pathway. Thus, these compounds may be able to induce host defenses and protect plants against a wide range of pathogens, including bacteria and fungi.

[0365] Examples B, C and D described below demonstrate the direct in vitro cell inactivity of compounds according to formula (I) against various pathogens, including bacteria and fungi, and thus demonstrate the mechanism of action of compounds according to formula (I) as inducers of plant host defense.

[0366] Examples E, F, G, H and I set out below demonstrate the in vivo activity of compounds according to formula (I) in plants by stimulating plant defenses against various pathogens that infect plants, such as bacteria and fungi.

[0367] Examples J, K, L, M and N set out below provide comparative examples of the in vivo activity in plants of compounds prepared according to the teachings of WO2004 / 024692 compared to compounds of formula (I) according to the present invention.

[0368] Example A: Induction of defense gene expression in Arabidopsis thaliana Arabidopsis thaliana reporter plants containing the green fluorescent protein (GFP) coding sequence linked to the salicylic acid-responsive promoter sequence of the PR1 (pathogenesis-related protein I) gene (AT2G14610) were grown for 5 days and then sprayed with compounds. Three days after spraying, plant fluorescence was assessed using a MacroFluo instrument from Leica Microsystems (Wetzlar, Germany). Fluorescence was quantified using Meta-Morph Microscopy Automation & Image Analysis Software (Molecular Devices, Sunnyvale, CA, United States).

[0369] The background fluorescence of mock-treated leaves was set at 1.00. Salicylic acid treatment (300 ppm) resulted in a relative fluorescence value of 2.70, demonstrating the validity of the test system.

[0370] In this test, the following compounds according to the invention: I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.10; I.11; I.12; I.13; I.14; I.15; I.16; I.17; I.18; I.20; I.21; I.22; I.23; I.24; I.25; I.26; I.27; I.28; I.29; I.30; I.31; I.32; I.33; I.34; I.36; I.37; I.38; I.39; I.40; I.41; I.42; I.44; I.45 showed relative fluorescence values ​​of at least greater than 2 at a compound concentration of 300 ppm.

[0371] In this test, the following compounds according to the present invention: I.02; I.03; I.05; I.09; I.10; I.11; I.12; I.13; I.15; I.16; I.17; I.18; I.20; I.23; I.24; I.28; I.29; I.31; I.32; I.33; I.34; I.36; I.37; I.42; I.45 exhibited relative fluorescence values ​​of at least 2 at a compound concentration of 75 ppm. Salicylic acid compounds are major defense hormones against plant pathogens. Since all of the above compounds stimulate the salicylic acid pathway, they are believed to be able to protect plants from a wide range of pathogens.

[0372] Example B: In vitro cell assay of Pseudomonas syringae pv. tomato Solvent: DMSO Medium: LB broth medium (Luria Broth Miller) Sigma Inoculum: Bacterial suspension Test compounds were dissolved in DMSO and the solution was used to prepare a range of concentrations as required. The final concentration of DMSO used in the assay was ≦1%.

[0373] The inoculum was obtained from a bacterial preculture grown in liquid medium and diluted to the desired optical density (OD ).

[0374] Compounds are evaluated for their ability to inhibit bacterial growth in liquid culture assays. Compounds are added to the medium containing bacterial suspension at desired concentrations. After 24 hours of incubation, the efficacy of compounds is determined by spectrophotometric measurement of bacterial growth. Inhibition is determined by comparing the absorbance value of the well containing compound with the absorbance value of the control well without compound.

[0375] In this test, the following compounds according to the invention: I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.10; I.11; I.12; I.13; I.14; I.15; I.16; I.44; I.45 showed no direct activity (less than 30% efficacy) at an active ingredient concentration of 20 ppm.

[0376] Example C: Botrytis cinerea in vitro cell assay Solvent: DMSO Medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), QSP 1 liter Inoculum: spore suspension The disinfectants were dissolved in DMSO and the solution was used to prepare the required concentration range. The final concentration of DMSO used in the assay was ≦1%.

[0377] A spore suspension of B. cinerea was prepared and diluted to the desired spore density.

[0378] Fungicides were evaluated for their ability to inhibit spore germination and mycelial growth in a liquid culture assay. The compound was added to the medium containing the spores at the desired concentration. After 5 days of incubation, the fungal toxicity of the compound was determined by measuring mycelial growth spectrophotometrically. Inhibition of fungal growth was determined by comparing the absorbance values ​​in wells containing the fungicide with those in control wells without the fungicide.

[0379] In this test, the following compounds according to the invention: I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.10; I.11; I.12; I.13; I.14; I.15; I.16; I.44; I.45 showed no direct activity (less than 30% efficacy) at an active ingredient concentration of 20 ppm.

[0380] Example D: Xanthomonas campestris pv. campestris in vitro cell assay Solvent: DMSO Medium: LB broth medium (Luria Broth Miller) Sigma Inoculum: Bacterial suspension Compounds were dissolved in DMSO and the solution was used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ≦1%.

[0381] The inoculum was obtained from a bacterial preculture grown in liquid medium and diluted to the desired optical density (OD ).

[0382] Compounds are evaluated for their ability to inhibit bacterial growth in liquid culture assays.Compounds are added to the medium containing bacterial suspension at desired concentrations.After 24 hours of incubation, the efficacy of compounds is determined by spectrophotometric measurement of bacterial growth.Inhibition is determined by comparing the absorbance value of the well containing compound with the absorbance value of the control well that does not contain active ingredient.

[0383] In this test, the following compounds according to the invention: I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.10; I.11; I.12; I.13; I.14; I.15; I.16; I.44; I.45 showed no direct activity (less than 30% efficacy) at an active ingredient concentration of 20 ppm.

[0384] Example E: In vivo prevention test with Pseudomonas syringae pv. tomato (bacterial spot disease on tomato) The active ingredients to be tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / tween® and diluted with water to obtain the desired active ingredient concentration.

[0385] Tomato seedlings were treated by spraying with the active ingredient prepared as described above, control plants were treated with the aqueous solution of acetone / dimethyl sulfoxide / tween® only.

[0386] After 72 hours, plants were contaminated by spraying the leaves with an aqueous bacterial suspension of Pseudomonas syringae pv. tomato. The contaminated tomato plants were then incubated in a saturated atmosphere of 22°C daytime / 20°C nighttime at -70% relative humidity for 4 days, followed by 1 or 2 days at 22°C daytime / 20°C nighttime at 70-80% relative humidity.

[0387] The test was evaluated 5 or 6 days after inoculation, 0% means an efficacy corresponding to that of the control plants, 100% means that no disease damage was observed.

[0388] In this test, the following compound according to the invention: I.01 showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm.

[0389] In this test, the following compounds according to the invention: I.02; I.09 showed an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm.

[0390] In this test, the following compounds according to the invention: I.07; I.09; I.11; I.12; I.15; I.26 showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm.

[0391] In this test, the following compounds according to the invention: I.03; I.16; I.21; I.22; I.25; I.33; I.37; I.45 showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm.

[0392] In this test, the following compounds according to the invention: I.10; I.17; I.23; I.24; I.40 showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm.

[0393] In this test, the following compounds according to the invention: I.03; I.09; I.25; I.33; I.39; I.43 showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm.

[0394] In this test, the following compounds according to the invention: I.01; I.12; I.14; I.20; I.34; I.36; I.45 showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm.

[0395] In this test, the following compounds according to the invention: I.10; I.11; I.15; I.16; I.17; I.18; I.21; I.22 showed an efficacy of 90% to 100% at an active ingredient concentration of 125 ppm.

[0396] Example F: In vivo preventive testing with Peronospora parasitica (crucifer downy mildew) The active ingredients to be tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / tween® and diluted with water to obtain the desired active ingredient concentration.

[0397] Young cabbage plants were treated by spraying with the active ingredient prepared as described above, control plants were treated with the aqueous acetone / dimethyl sulfoxide / tween® solution only.

[0398] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Peronospora parasitica spores. The contaminated cabbage plants were incubated at 20°C and 100% relative humidity for 5 days.

[0399] The test was evaluated 5 days after inoculation, 0% meaning an efficacy corresponding to that of the control plants, 100% meaning that no disease damage was observed.

[0400] In this test, the following compounds according to the invention: I.01; I.04; I.26 showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm.

[0401] In this test, the following compounds according to the invention: I.10; I.14; I.17; I.33 showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm.

[0402] In this test, the following compounds according to the invention: I.02; I.09; I.13; I.15; I.23; I.28 showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm.

[0403] In this test, the following compound according to the invention: I.03 showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm.

[0404] In this test, the following compounds according to the invention: I.12; I.31; I.35; I.44 showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm.

[0405] In this test, the following compounds according to the invention: I.02; I.09; I.10; I.13; I.14; I.15; I.16; I.17; I.23; I.26; I.28; I.29; I.30; I.33; I.38; I.40; I.42 showed an efficacy of 90% to 100% at an active ingredient concentration of 125 ppm.

[0406] Example G: In vivo prevention studies with Uromyces appendiculatus (bean rust) The active ingredients to be tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / tween® and diluted with water to obtain the desired active ingredient concentration.

[0407] Young bean plants were treated by spraying with the active ingredient prepared as described above, control plants were treated with the aqueous acetone / dimethyl sulfoxide / tween® solution only.

[0408] After 72 hours, plants were contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants were incubated at 20°C and 100% relative humidity for 24 hours, then at 20°C and 70-80% relative humidity for 9 days.

[0409] The test was evaluated 10 days after inoculation, 0% meaning an efficacy corresponding to that of the control plants, 100% meaning that no disease damage was observed.

[0410] In this test, the following compounds according to the invention: I.03; I.05 showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm.

[0411] In this test, the following compound according to the invention: I.09 showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm.

[0412] In this test, the following compounds according to the invention: I.01; I.02 showed an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm.

[0413] Example H: In vivo preventive testing with Colletotrichum lindemuthianum (pea anthracnose) The active ingredients to be tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / tween® and diluted with water to obtain the desired active ingredient concentration.

[0414] Young bean plants were treated by spraying with the active ingredient prepared as described above, control plants were treated with the aqueous acetone / dimethyl sulfoxide / tween® solution only.

[0415] After 72 hours, plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores. The contaminated bean plants were incubated at 20°C and 100% relative humidity for 24 hours, then at 20°C and 90% relative humidity for 5 days.

[0416] The test was evaluated 6 days after inoculation, 0% meaning an efficacy corresponding to that of the control plants, 100% meaning that no disease damage was observed.

[0417] In this test, the following compound according to the invention: I.04 showed an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm.

[0418] In this test, the following compound according to the invention: I.09 showed an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm.

[0419] In this test, the following compounds according to the invention: I.02; I.03 showed an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm.

[0420] In this test, the following compounds according to the invention: I.04; I.10; I.31; I.42 showed an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm.

[0421] In this test, the following compounds according to the invention: I.14; I.15; I.33 showed an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm.

[0422] In this test, the following compounds according to the invention: I.02; I.13 showed an efficacy of 90% to 100% at an active ingredient concentration of 31 ppm.

[0423] Example I: In vivo prevention test with Xanthomonas campestris pv. campestris (black spot disease on cabbage) The active ingredients to be tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / tween® and diluted with water to obtain the desired active ingredient concentration.

[0424] Cabbage seedlings were treated by spraying with the active ingredient prepared as described above, control plants were treated with the aqueous acetone / dimethyl sulfoxide / tween® solution only.

[0425] After 72 hours, the plants were contaminated by spraying the leaves with an aqueous bacterial suspension of Xanthomonas campestris pv. campestris. The contaminated cabbage plants were incubated at 27°C and 95% relative humidity for 8 or 10 days.

[0426] The test was evaluated 8 or 10 days after inoculation, 0% means an efficacy corresponding to that of the control plants, 100% means that no disease damage was observed.

[0427] In this test, the following compounds according to the invention: I.02; I.03; I.15; I.31; I.38; I.44 showed an efficacy of 70% to 79% at an active ingredient concentration of 125 ppm.

[0428] In this test, the following compounds according to the invention: I.23; I.30; I.45 showed an efficacy of 80% to 89% at an active ingredient concentration of 125 ppm.

[0429] In this test, the following compounds according to the invention: I.10; I.12; I.14; I.17; I.24; I.25; I.26; I.29; I.33; I.34; I.36; I.42 showed an efficacy of 90% to 100% at an active ingredient concentration of 125 ppm.

[0430] Example J: Comparative Example Compound CMP1 was tested in an in vivo preventative test against Pseudomonas syringae pv. tomato (bacterial spot disease on tomato) under the same conditions as described in Example E.

[0431] Compound CMP1 was prepared as described in WO2004 / 024692.

[0432] The results are shown in the table below. [Table 8]

[0433] Compounds of formula (I) of the present invention have been found to exhibit better efficacy than the structurally related compound CMP1 when tested at a concentration of 500 ppm.

[0434] More specifically, compound I.02 was found to be at least 90% effective at a concentration of 500 ppm, while CMP1 was found to be less than 10% effective at the same concentration.

[0435] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP1 when tested at a concentration of 125 ppm.

[0436] More specifically, compound I.14 was found to be at least 80% effective at a concentration of 125 ppm, while CMP1 was found to be less than 10% effective at the same concentration.

[0437] Compound CMP2 was tested in an in vivo preventative test against Pseudomonas syringae pv. tomato (bacterial spot disease on tomato) under the same conditions as described in Example E.

[0438] Compound CMP2 was prepared as described in WO2004 / 024692.

[0439] The results are shown in the table below. [Table 9]

[0440] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP2 when tested at a concentration of 125 ppm.

[0441] More specifically, compounds I.01, I.43 and I.09 were found to be at least 70% effective at a concentration of 125 ppm, while CMP2 was found to be less than 10% effective at the same concentration.

[0442] Compound CMP3 was tested in an in vivo preventative test against Pseudomonas syringae pv. tomato (bacterial spot disease on tomato) under the same conditions as described in Example E.

[0443] Compound CMP3 was prepared as described in WO2004 / 024692.

[0444] The results are shown in the table below. [Table 10]

[0445] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP3 when tested at a concentration of 31 ppm.

[0446] More specifically, compounds I.07, I.10, I.11 and I.16 were found to be at least 70% effective at a concentration of 31 ppm, while CMP3 was found to be less than 10% effective at the same concentration.

[0447] Example K: Comparative Example Compound CMP2 was tested in an in vivo preventative test against Peronospora parasitica (crucifer downy mildew) under the same conditions as described in Example F.

[0448] Compound CMP2 was prepared as described in WO2004 / 024692.

[0449] The results are shown in the table below. [Table 11]

[0450] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP2 when tested at a concentration of 31 ppm.

[0451] More specifically, compounds I.01 and I.09 were found to be at least 70% effective at a concentration of 31 ppm, while CMP2 was found to be less than 10% effective at the same concentration.

[0452] Compound CMP3 was tested in an in vivo preventative test against Peronospora parasitica (crucifer downy mildew) under the same conditions as described in Example F.

[0453] Compound CMP3 was prepared as described in WO2004 / 024692.

[0454] The results are shown in the table below. [Table 12]

[0455] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP3 when tested at a concentration of 125 ppm.

[0456] More specifically, compounds I.10 and I.16 were found to be at least 90% effective at a concentration of 125 ppm, whereas CMP3 was found to be less than 40% effective at the same concentration.

[0457] Example L: Comparative Example Under the same conditions as described in Example H, Colletotrichum lindemuthianum (anthracnose on beans) The compound CMP1 was tested in an in vivo prophylactic study against

[0458] Compound CMP1 was prepared as described in WO2004 / 024692.

[0459] The results are shown in the table below. [Table 13]

[0460] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP1 when tested at a concentration of 31 ppm.

[0461] More specifically, compounds I.02, I.13 and I.14 were found to be at least 80% effective at a concentration of 31 ppm, whereas CMP1 was found to be less than 30% effective at the same concentration.

[0462] Under the same conditions as described in Example I, Colletotrichum lindemuthianum (anthracnose on beans) The compound CMP2 was tested in an in vivo prophylactic study against

[0463] Compound CMP2 was prepared as described in WO2004 / 024692.

[0464] The results are shown in the table below. [Table 14]

[0465] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP2 when tested at a concentration of 500 ppm.

[0466] More specifically, compound I.09 was found to be at least 80% effective at a concentration of 500 ppm, while CMP2 was found to be less than 10% effective at the same concentration.

[0467] Under the same conditions as described in Example I, Colletotrichum lindemuthianum (anthracnose on beans) The compound CMP5 was tested in an in vivo prophylactic study against

[0468] Compound CMP5 was prepared as described in WO2004 / 024692.

[0469] The results are shown in the table below. [Table 15]

[0470] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP5 when tested at a concentration of 31 ppm.

[0471] More specifically, compound I.42 was found to be at least 70% effective at a concentration of 31 ppm, while CMP5 was found to be no more than 30% effective at the same concentration.

[0472] Example M: ​​Comparative Example Under the same conditions as described in Example I, Xanthomonas campestris pv. campestris (black spot of cabbage) The compound CMP1 was tested in an in vivo prophylactic study against

[0473] Compound CMP1 was prepared as described in WO2004 / 024692.

[0474] The results are shown in the table below. [Table 16]

[0475] The compound of formula (I) of the present invention was found to exhibit better efficacy than the structurally related compound CMP1 when tested at a concentration of 31 ppm.

[0476] More specifically, compound I.14 was found to be at least 80% effective at a concentration of 31 ppm, while CMP1 was found to be less than 10% effective at the same concentration.

Claims

1. A compound of formula (I): [In the formula, R １ is a bromine atom or a chlorine atom; R ２ is selected from the group consisting of a bromine atom, a chlorine atom, an iodine atom, and a fluorine atom; R ３ is a hydrogen atom, C １ -C ６ -Alkyl, C １ -C ６ -Haloalkyl, C １ -C ６ -cyanoalkyl, C ２ -C ６ -Alkenyl, C ２ -C ６ -Alkynyl, C ３ -C ８ -cycloalkyl, aryl, heteroaryl, aralkyl, -C １ -C ６ -alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C １ -C ６ -Alkyl-Si(C １ -C ６ -alkyl) ３ and -C １ -C ６ -alkyl-cyclopropyl, R １ and R ２ When both are bromine atoms, R ３ is C １ -C ６ -Haloalkyl, C １ -C ６ -cyanoalkyl, C ２ -C ６ -Alkenyl, C ２ -C ６ -Alkynyl, C ３ -C ８ -cycloalkyl, aryl, heteroaryl, aralkyl, -C １ -C ６ -alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C １ -C ６ -Alkyl-Si(C １ -C ６ -alkyl) ３ and -C １ -C ６ -alkyl-cyclopropyl, R ３ is a hydrogen atom and C １ -C ６ - alkyl, R ２ is selected from the group consisting of bromine and iodine atoms; However, R １ is a chlorine atom, R ２ is not a chlorine atom.

2. R １ The compound according to claim 1 , wherein is a chlorine atom.

3. R １ The compound according to claim 1 , wherein is a bromine atom.

4. R ２ The compound according to any one of claims 1 to 3, wherein is selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.

5. R １ R ２ The compound according to any one of claims 1 to 4, which is different from

6. R １ is a chlorine atom, R ２ The compound according to claim 1 , wherein is a bromine atom.

7. R ３ is a hydrogen atom, C １ -C ６ -Alkyl, C １ -C ６ -Haloalkyl, C １ -C ６ -cyanoalkyl, C ２ -C ６ -Alkenyl, C ２ -C ６ -Alkynyl, C ３ -C ８ -cycloalkyl, aralkyl and -C １ -C ６ 7. The compound according to any one of claims 1 to 6, wherein the compound is selected from the group consisting of: -alkyl-cyclopropyl.

8. The use of the compounds of formula (I) for controlling phytopathogenic fungi and / or bacteria on plants or plant parts in crop protection. [In the formula, R １ is a bromine atom or a chlorine atom; R ２ is selected from the group consisting of a bromine atom, a chlorine atom, an iodine atom, and a fluorine atom; R ３ is a hydrogen atom, C １ -C ６ -Alkyl, C １ -C ６ -Haloalkyl, C １ -C ６ -cyanoalkyl, C ２ -C ６ -Alkenyl, C ２ -C ６ -Alkynyl, C ３ -C ８ -cycloalkyl, aryl, heteroaryl, aralkyl, -C １ -C ６ -alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C １ -C ６ -Alkyl-Si(C １ -C ６ -alkyl) ３ and -C １ -C ６ -alkyl-cyclopropyl; However, R １ is a chlorine atom, R ２ is not a chlorine atom.

9. R １ The use according to claim 8, wherein is a chlorine atom.

10. R １ The use according to claim 8, wherein is a bromine atom.

11. R ２ The use according to any one of claims 8 to 10, wherein is selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom.

12. R １ R ２ The use according to any one of claims 8 to 11, which is different from

13. R １ is a chlorine atom, R ２ The use according to claim 8, wherein is selected from the group consisting of fluorine atoms and chlorine atoms.

14. R １ is a chlorine atom, R ２ The use according to claim 8, wherein is a bromine atom.

15. R ３ is a hydrogen atom, C １ -C ６ -Alkyl, C １ -C ６ -Haloalkyl, C １ -C ６ -cyanoalkyl, C ２ -C ６ -Alkenyl, C ２ -C ６ -Alkynyl, C ３ -C ８ -cycloalkyl, aryl, heteroaryl, aralkyl, -C １ -C ６ -alkyl-heteroaryl, 4-, 5- or 6-membered heterocycle, -C １ -C ６ -Alkyl-Si(C １ -C ６ -alkyl) ３ and -C １ -C ６ The use according to any one of claims 8 to 14, wherein the aryl group is selected from the group consisting of -alkyl-cyclopropyl.

16. 2. A process for preparing a compound of formula (I) according to claim 1, comprising reacting a compound of formula (II) or a salt thereof with a compound of formula (III) or a salt thereof to provide said compound of formula (I). [In the formula, R １ , R ２ and R ３ is as claimed in claim 1; U １ is a halogen atom, a hydroxyl group or C １ -C ６ -alkoxy group.]

17. 2. A process for the preparation of a compound of formula (I) according to claim 1, comprising the step of brominating or chlorinating a compound of formula (IV) or a salt thereof to provide a compound of formula (I): [In the formula, R １ , R ２ and R ３ is as claimed in claim 1; U ２ is a hydrogen atom, a chlorine atom or a bromine atom; U ３ is a hydrogen atom, a chlorine atom or a bromine atom; However, U ２ Or U ３ At least one of is a hydrogen atom.

18. 2. A process for the preparation of a compound of formula (I) according to claim 1, comprising the step of halogenating a compound of formula (I) to provide a compound of formula (I): [In the formula, R １ , R ２ and R ３ is as defined in claim 1.

19. 2. A process for the preparation of a compound of formula (I) according to claim 1, comprising the steps of diazotisation of a compound of formula (VI) or a salt thereof, followed by aromatic substitution to provide a compound of formula (I): [In the formula, R １ , R ２ and R ３ is as claimed in claim 1; U ４ is an amino group, a chlorine atom or a bromine atom; U ５ is an amino group, a chlorine atom or a bromine atom; However, U ４ Or U ５ At least one of the groups is an amino group.

20. A composition comprising at least one compound of formula (I) according to any one of claims 1 to 7 and at least one agriculturally suitable carrier.

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