Microbicidal pyrazole derivatives

Abstract

A compound of formula (I) - wherein the substituents are as defined in claim 1 - and the agrochemically acceptable salts, or N-oxides of those compounds, which can be used as fungicides.

Description

[0001] This invention relates to pyrazole derivatives that kill microorganisms, for example, as active ingredients, having microbial activity, particularly fungicidal activity. The invention also relates to the preparation of these pyrazole derivatives, to intermediates useful in the preparation of these pyrazole derivatives, to the preparation of these intermediates, to agricultural chemical compositions comprising at least one of these pyrazole derivatives, to the preparation of these compositions, and to the use of these pyrazole derivatives or compositions in agriculture or horticulture for controlling or preventing infection of plants, harvested food crops, seeds, or inanimate materials by plant pathogenic microorganisms, particularly fungi.

[0002] According to a first aspect of the invention, a compound having formula (I) or an agrochemically acceptable salt thereof, or an N-oxide, is provided:

[0003] (I)

[0004] in

[0005] R 1 Selected from hydrogen, C1-C 4- Alkyl, C2-C 4- alkenyl, C2-C4-alkynyl, or C3-C 6- cycloalkyl;

[0006] R 2 Selected from cyano, hydroxy, amino, C1-C4-alkoxy, C3-C6-enoxy, C3-C6-alkynoxy, C3-C6-cycloalkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C1-C4-haloalkylthioalkyl;

[0007] R 3 Selected from hydrogen, halogens, or C1-C4-alkyl groups;

[0008] R 4 Selected from hydrogen, halogen, cyano, or C1-C4-alkyl;

[0009] R 5 and R 6 Independently selected from hydrogen or C1-C4-alkyl;

[0010] A 1 Selected from CR 7 Or N;

[0011] A 2 Selected from CR 8Or N;

[0012] A 3 Selected from CR 9 Or N;

[0013] R 7 R 8 and R 9 It is independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C1-C4-haloalkyl;

[0014] Q is selected from a 6-membered heteroaryl group, wherein any one of the 6-membered heteroaryl groups is selected from...

[0015]

[0016] The interlacing lines represent bonds to the remainder of the molecule; and each of the six heteroaryl groups is unsubstituted or independently selected from R by one or up to a maximum possible number of R groups. 10 Substituents of R, wherein R 10 Independently selected from halogen, hydroxyl, cyano, carboxyl, amino, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-enoxy, C2-C4-alkynoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, trifluoromethanesulfonyloxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, N-C1-C4-alkylamino, N,N-di(C1-C4)-alkylamino, C1-C 4- Alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimide, N-hydroxy-C1-C 4- alkyl-carbonimide, phenyl, 5- or 6-membered heteroaryl, or C3-C 6- The cycloalkyl group, wherein any one of the 5- or 6-membered heteroaryl groups comprises 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl group, and C3-C6-cycloalkyl group is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy; and

[0017] Z 1The group is selected from C1-C4-alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-ynyl.

[0018] Surprisingly, it has been found that compounds of formula (I) have very favorable levels of bioactivity for protecting plants against fungal diseases for practical purposes.

[0019] According to a second aspect of the invention, an agricultural chemical composition comprising an effective amount of the compound of formula (I) according to the invention is provided. This agricultural composition may further comprise at least one additional active ingredient and / or an agriculturally chemically acceptable diluent or carrier.

[0020] According to a third aspect of the invention, a method for controlling or preventing the infection of useful plants by plant pathogenic microorganisms is provided, wherein a fungicide effective amount of a compound of formula (I) according to the invention, or a composition comprising a compound of formula (I), is applied to the plants, parts thereof, or the site thereof.

[0021] According to a fourth aspect of the invention, the use of a compound having formula (I) according to the invention is provided as a fungicide. According to this particular aspect of the invention, this use may exclude methods of treating a human or animal body by surgery or therapy, and diagnostic methods performed on a human or animal body.

[0022] Compounds of formula (I) or intermediates of formula (III) according to the invention having at least one basic center can form, for example, acid addition salts with: strong inorganic acids (such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, phosphoric acid or hydrohalic acid), strong organic carboxylic acids (such as unsubstituted or, for example, halogenated C1-C4-alkylcarboxylic acids, such as acetic acid, such as saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid), or organic sulfonic acids (such as unsubstituted or, for example, halogenated C1-C4-alkylsulfonic acids or arylsulfonic acids, such as methanesulfonic acid or p-toluenesulfonic acid).

[0023] Compounds of formula (I) or intermediate compounds of formula (III) according to the invention having at least one acidic group may, for example, form salts with a base, such as mineral salts, like alkali metal or alkaline earth metal salts, such as sodium, potassium or magnesium salts; or form salts with ammonia or organic amines (such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-alkylamines, such as ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or tri-hydroxyalkylamines, such as monoethanolamine, diethanolamine or triethanolamine).

[0024] The presence of one or more possible asymmetric carbon atoms in compounds of formula (I) according to the invention means that these compounds can exist in chiral isomers (i.e., enantiomers or diastereomers). Furthermore, as a result of restricted rotation around the single bond, transisomers may exist. Formula (I) is intended to include all those possible isomer forms and mixtures thereof. The invention includes all those possible isomer forms and mixtures thereof of compounds of formula (I) according to the invention. Similarly, compounds of formula (I) are intended to include all possible tautomers (including lactam-lactamimide tautomers and keto-enol tautomers) (where present). The invention includes all possible tautomer forms of compounds of formula (I) according to the invention.

[0025] In each case, the compound having formula (I) according to the invention is in a free form, an oxidized form (as an N-oxide), a covalently hydrated form, or a salt form (e.g., an agronomically usable or agrochemically acceptable salt form). The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. For example, they are described in “Heterocyclic N-oxides”, published by A. Albini and S. Pietra in 1991 by CRC Press, Boca Raton. N-oxides can be prepared by reacting a compound having formula (I) with a suitable oxidant (e.g., H₂O₂ / urea adduct) in the presence of an acid anhydride (e.g., trifluoroacetic anhydride). Such oxidations are known from the literature, for example from J. Med. Chem., 1989, 32 (12), 2561-73 or WO2000 / 15615. The compounds of formula (I) according to the invention also include hydrates that can be formed during salt formation.

[0026] As used herein, the term "halogen" or "halogenated" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iodo), preferably fluorine, chlorine, or bromine. This also applies accordingly to halogens combined with other meanings, such as halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated alkoxy, and halogenated cycloalkyl.

[0027] As used in this article, amino refers to the -NH2 group.

[0028] As used in this article, cyano refers to the -CN group.

[0029] As used herein, the term "hydroxyl" or "hydroxyl" refers to the -OH group.

[0030] As used in this article, the term "carboxylic acid" refers to the -COOH group.

[0031] As used in this article, the term "C1-C" n "-alkyl" refers to a saturated straight-chain or branched hydrocarbon group having 1 to n carbon atoms attached via any one of the carbon atoms, such as any of the following groups: methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

[0032] As used in this article, the term "C2-C" n "-Alkenyl" refers to a straight-chain or branched alkenyl chain portion having two to n carbon atoms and one or two double bonds, such as vinyl, prop-1-alkenyl, and but-2-alkenyl.

[0033] As used in this article, the term "C2-C" n "-Alynyl" refers to a straight-chain or branched alkynyl chain portion having two to n carbon atoms and a triple bond, such as ethynyl, prop-2-alkynyl, and but-3-alkynyl.

[0034] As used in this article, the term "C3-C" n "-cycloalkyl" refers to tri(3) to n-membered cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0035] As used in this article, the term "C1-C" n "-alkoxy" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having one (1) to n carbon atoms attached via an oxygen atom, i.e., any one of the following groups, for example: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy. As used herein, the term "C2-C" refers to... n "-Alkenyloxy" refers to a straight or branched alkenyl chain with two (2) to n carbon atoms attached via an oxygen atom (as mentioned above).

[0036] As used in this article, the term "C" 2- C n "-Oyneoxy group" refers to a group with the formula -OR a The group, wherein R a It is C as generally defined above. 2- C n -Alkyne group.

[0037] As used in this article, the term "C1-C" n -alkoxy-C1-C n "-alkyl" refers to a C1-C group as defined above. n -Alkoxy-substituted alkyl C1-C n -alkyl (as defined above). Examples are methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl. This term can be used interchangeably with the term "C1-C". n -alkyl-C1-C n "-alkoxy" is used interchangeably; the term refers to a compound with the formula -R a -OR b The group, wherein R a It is C1-C as defined above. n -alkyl, and R b This refers to C1-C as defined above. n -alkyl.

[0038] As used in this article, the term "C1-C" n -alkoxy-C1-C n "-alkoxy" refers to a compound with the formula -OR a -OR b The group, wherein R a It is C1-C as defined above. n -alkyl, and R b This refers to C1-C as defined above. n -alkyl.

[0039] As used in this article, the term "C1-C" n -alkyl-C1-Cn -alkoxy-C1-C n "-alkoxy" refers to a compound with the formula -R a -OR b -OR c The group, wherein R a It is C1-C as defined above. n -alkyl, and R b and R c This refers to C1-C as defined above. n -alkyl. As used herein, the term "C3-C" refers to... n -cycloalkyl-C1-C n "-alkyl" refers to a compound formed by C3-C2. n - Cycloalkyl-substituted alkyl groups (as mentioned above). Examples are cyclopropylmethyl and cyclopropylethyl. Similarly, the term "C3-C" refers to... n -Halogenated cycloalkyl-C1-C n "-alkyl" refers to an alkyl group substituted with a cycloalkyl group, wherein the cycloalkyl group is substituted by one or more identical or different halogen atoms. Examples are 3,3-difluorobutylmethyl and 1-chlorocyclopropylmethyl.

[0040] As used in this article, the term "C1-C" n "-Halogenated alkyl" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to n carbon atoms attached via any one carbon atom, wherein some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., any one of the following, for example: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl. Similarly, as used herein, the term "C1-C" n "-Haloalkoxy" refers to a C1-C group that is substituted by one or more halogen atoms that may be the same or different. n -alkoxy group.

[0041] As used in this article, the term "C1-C" n -alkylthio" or "C1-C n "-alkylthioalkyl" refers to a C1-C2 bonded by a sulfur atom. n -alkyl. Examples include methylthio, ethylthio, and isopropylthio-.

[0042] As used in this article, the term "C1-C" n -haloalkylthio" or "C1-C n"-halogenated alkyl thioalkyl" refers to a C1-C2 bonded by a sulfur atom. n - Haloalkyl. Examples are, for example, trifluoromethylthioalkyl, difluoromethylthioalkyl, and 2,2-difluoroethylthioalkyl. As used herein, the term "C1-C" refers to... n "-alkylsulfinyl" refers to a C1-C group linked by a sulfur atom through a sulfinyl group (or S(=O)-). n -alkyl.

[0043] As used in this article, the term "C1-C" n "-alkylsulfonyl" refers to a C1-C group connected by a sulfur atom through a sulfonyl group (or S(=O)2-). n -alkyl.

[0044] As used in this article, the term "C1-C" n -alkylsulfonyl-C1-C n "-alkyl" refers to a compound formed by C1-C2. n -alkylsulfonyl-substituted C1-C n -alkyl.

[0045] As used in this article, the term "C1-C" n "-alkylcarbonyl" refers to a C1-C group linked by a carbonyl (C=O) group. n -alkyl.

[0046] As used in this article, the term "C1-C" n "-alkoxycarbonyl" refers to a C1-C group connected by a carbonyl (or C=O) group. n -alkoxy moiety.

[0047] As used in this article, the term "C1-C" n "-alkylaminocarbonyl" refers to a C1-C group linked by a carbonyl (C=O) carbon atom. n -alkylamino (or R a NHC(=O)-), where R a It is C1-C n -alkyl.

[0048] As used in this article, the term "N-C1-C" n- "alkylamino" refers to a compound with the formula -NH-R a The group, wherein R a It is C1-C as defined above. n -alkyl.

[0049] As used in this article, the term "N,N-II (C1-C)" n "-alkyl)amino" refers to a substance with the formula -N(R) a )R aThe groups, wherein each R a They can be the same or different as defined above, C1-C n -alkyl.

[0050] As used in this article, the term "N-C1-C" n -alkoxy-C-C1-C n "-alkyl-carbonimide group" refers to a group having the formula -C(R a )=NO(R b ) groups, wherein R a It is C as generally defined above. 1- C n -alkyl, and R b It is C as generally defined above. 1- C n -alkyl.

[0051] As used herein, the term "N-hydroxy-C-C1-C" n "-alkyl-carbonimide group" refers to a group having the formula -C(R a The group = NOH, where R a It is C as generally defined above. 1- C n -alkyl.

[0052] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic group comprising 1, 2, 3, or 4 heteroatoms independently selected from N, O, or S. Examples of heteroaryl groups include, but are not limited to, furanyl, pyrroleyl, thiopheneyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, or pyridinyl. n -alkyl" or "heteroaryl-C3-C" n "-cycloalkyl" refers to C1-C1 alkyl groups that are substituted with heteroaryl groups. n -alkyl or C3-C n -Cycloalkyl. Heteroaryl-C1-C n -alkyl or heteroaryl-C3-C n -Cycloalkyl groups can be substituted on heteroaryl, alkyl, and / or cycloalkyl groups when appropriate.

[0053] As used herein, the term “control” means reducing the number of pests, eliminating pests and / or preventing further pest damage, thereby reducing damage to plants or plant-derived products.

[0054] As used herein, the term "pest" refers to insects and mollusks found in the storage of agricultural, horticultural, forestry, and plant-derived products (such as fruits, grains, and timber); as well as those pests associated with damage to man-made structures. The term "pest" encompasses all stages of the pest's life cycle.

[0055] As used herein, the term "effective amount" refers to the amount of a compound or its salt that provides the desired effect when applied in a single or multiple applications.

[0056] The effective amount is readily determined by those skilled in the art using known techniques and by observing results obtained under similar conditions. In determining the effective amount, numerous factors are considered, including but not limited to, the type of plant or derivative to be applied; the pest to be controlled and its life cycle; the specific compound applied; the type of application; and other relevant circumstances.

[0057] As used herein, the terms “room temperature” or “RT” or “rt” or “ambient temperature” refer to a temperature of about 15°C to about 35°C. For example, rt can refer to a temperature of about 20°C to about 30°C.

[0058] The following list provides the substituents R of compounds having formula (I) according to the present invention. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 A 1 A 2 A 3 Q and Z 1 The definitions, including preferred definitions, are provided below. For any of these substituents, any definition given below may be combined with any other definition of any substituent given below or elsewhere in this document.

[0059] In one embodiment of the present invention, R 1 Selected from hydrogen, C1-C 4- Alkyl, C2-C 4- Alkenyl, C2-C4-ynyl, or C3-C6 cycloalkyl. In another embodiment of the invention, R 1 It is a C1-C4 alkyl group. Preferably, R 1 It is a C1-C3-alkyl group. More preferably, R 1 It is methyl, ethyl, or isopropyl. Even more preferably, R 1 It is a methyl group.

[0060] In one embodiment of the present invention, R 2 Selected from cyano, hydroxy, amino, C1-C4-alkoxy, C3-C6-enoxy, C3-C6-alkynoxy, C3-C6-cycloalkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C1-C4-haloalkylthioalkyl. Preferably, R 2 It is cyano, hydroxy, C1-C3-alkoxy, C3-C6-cycloalkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, C1-C2-alkylthioalkyl, C1-C2-alkylsulfinyl, or C1-C2-alkylsulfonyl. More preferably, R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl. Even more preferably, R 2 It is a C1-C3-alkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl. Even more preferably, R 2 It is methoxy, ethoxy, methoxymethyl, or methylthioalkyl.

[0061] In one embodiment of the present invention, R 3 Selected from hydrogen, halogen, or C1-C4-alkyl. In another embodiment, R 3 Selected from hydrogen, halogen, or C1-C3-alkyl. Preferably, R 3 It is hydrogen, fluorine, chlorine, or methyl. More preferably, R 3 It is hydrogen or methyl. Even more preferably, R 3 It is hydrogen. In another embodiment, R 3 It is hydrogen or C1-C3-alkyl.

[0062] In one embodiment of the present invention, R 4 Selected from hydrogen, halogen, cyano, or C1-C4-alkyl. Preferably, R 4 It is hydrogen, fluorine, chlorine, cyano, or C1-C3-alkyl. More preferably, R 4 It is hydrogen, fluorine, chlorine, or C1-C3-alkyl. Even more preferably, R 4 It is hydrogen or methyl. In one embodiment, R 4 It is hydrogen. In another embodiment, R 4 It is a methyl group.

[0063] In one embodiment of the present invention, R5 and R 6 Independently selected from hydrogen or C1-C 4- Alkyl group. Preferably, R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl. More preferably, R 5 and R 6 Independently selected from hydrogen or methyl. Even more preferably, R 5 and R 6 It is hydrogen.

[0064] In an embodiment of the present invention, A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N. Preferably, in one embodiment of the invention, A 1 Selected from CR 7 And A 2 and A 3 It is N. Preferably, in another embodiment, A 1 and A 2 It is N; and A 3 Selected from CR 9 Preferably, in another embodiment, A 1 It is N; A 2 It is CR 8 And A 3 It is N. More preferably, A 1 A 2 and A 3 It is N.

[0065] In another embodiment of the invention, A 1 and A 2 It is N, and A 3 It is CR 9 In yet another embodiment of the invention, A 1 It is CR 7 A 2 It is CR 8 And A 3 It is N. In yet another embodiment of the invention, A 1 It is N; A 2 It is CR 8 And A 3 It is CR 9 In yet another embodiment of the invention, A 1 It is CR7 A 2 It is N; and A 3 It is CR 9 .

[0066] In an embodiment of the present invention, R 7 R 8 and R 9 Independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, or C1-C4-haloalkyl. Preferably, R 7 R 8 and R 9 Independently selected from hydrogen, halogen, methyl, or trifluoromethyl. More preferably, R 7 R 8 and R 9 It is hydrogen.

[0067] In one embodiment of the present invention, Q is selected from 6-membered heteroaryl groups, wherein any one of the 6-membered heteroaryl groups is selected from...

[0068]

[0069] The interlacing lines represent bonds to the remainder of the molecule; and each of the six heteroaryl groups is unsubstituted or independently selected from R by one or up to a maximum possible number of R groups. 10 Substituents of R, wherein R 10 Independently selected from halogen, hydroxyl, cyano, carboxyl, amino, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-enoxy, C2-C4-alkynoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, trifluoromethanesulfonyloxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, N-C1-C4-alkylamino, N,N-di(C1-C4)-alkylamino, C1-C 4- Alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimide, N-hydroxy-C1-C 4- alkyl-carbonimide, phenyl, 5- or 6-membered heteroaryl, or C3-C 6-Cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups comprises 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy.

[0070] Preferably, Q is selected from 6-membered heteroaryl groups, wherein any one of the 6-membered heteroaryl groups is selected from...

[0071]

[0072] The interlacing lines represent bonds to the remainder of the molecule; and each of the six heteroaryl groups is unsubstituted or is independently selected from R1 and R2. 10 Substituents of R, wherein R 10 The group is selected from halogen, cyano, amino, C1-C3-alkyl, C1-C3-alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups comprises one heteroatom selected from N, and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by one or two substituents independently selected from halogen, cyano, or C1-C4-alkyl.

[0073] More preferably, Q is selected from 6-membered heteroaryl groups, wherein any one of the 6-membered heteroaryl groups is selected from...

[0074]

[0075] The interlacing lines represent bonds to the remainder of the molecule; and each of the six heteroaryl groups is unsubstituted or is independently selected from R1 and R2. 10 Substituents of R, wherein R 10 It is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl.

[0076] In another embodiment of the invention, Q is selected from...

[0077]

[0078] The interlaced lines represent bonds to the remainder of the molecule; wherein any of the six heteroaryl groups is unsubstituted or is independently selected from R1 and R2. 10 Substituents are substituted, and R is wherein 10As defined above. Preferably, Q is selected from Q1, Q2, Q3, or Q4; wherein Q1, Q2, Q3, and Q4 are unsubstituted or are selected independently by one or two of R. 10 Substituents are substituted, and R is wherein 10 It is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl.

[0079] Preferably, Q is selected from Q1, Q2, or Q3.

[0080]

[0081] The interlaced lines represent bonds to the remainder of the molecule; wherein any of the six heteroaryl groups is unsubstituted or is independently selected from R1 and R2. 10 Substituents are substituted, and R is wherein 10 As defined above. Preferably, Q is selected from Q1, Q2, or Q3; wherein Q1, Q2, and Q3 are unsubstituted or are selected independently by one or two of R. 10 Substituents are substituted, and R is wherein 10 It is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl.

[0082] More preferably, Q is Q1:

[0083] Q1

[0084] The interlaced lines represent bonds to the remainder of the molecule, wherein any of the six heteroaryl groups is unsubstituted or is independently selected from R1 and R2. 10 Substituents are substituted, and R is wherein 10 It is as defined above. Preferably, Q is Q1; wherein Q1 is unsubstituted or is composed of one or two independently selected from R. 10 Substituents are substituted, and R is wherein 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl. More preferably, Q is Q1; wherein Q1 is unsubstituted or is composed of one or two molecules independently selected from R. 10 Substituents are substituted, and R is wherein 10 Selected from halogen, cyano, or amino groups.

[0085] In an embodiment of the present invention, R 10Selected from halogens, hydroxyl groups, cyano groups, carboxyl groups, amino groups, C1-C4-alkyl groups, C1-C4-haloalkyl groups, C1-C4-alkoxy groups, C1-C4-haloalkoxy groups, C2-C4-enoxy groups, C2-C4-alkynoxy groups, C1-C4-alkylthioalkyl groups, C1-C4-alkylsulfinyl groups, C1-C4-alkylsulfonyl groups, trifluoromethylsulfonyloxy groups, C1-C4-alkoxy-C1-C4-alkyl groups, C1-C4-alkoxy-C1-C4-alkoxy groups, N-C1-C4-alkylamino groups, N,N-di(C1-C4)-alkylamino groups, C1-C 4- Alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimide, N-hydroxy-C1-C 4- alkyl-carbonimide, phenyl, 5- or 6-membered heteroaryl, or C3-C 6- The cycloalkyl group, wherein any one of the 5- or 6-membered heteroaryl groups comprises 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl group, and C3-C6-cycloalkyl group is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy. In another embodiment of the invention, R 10 Selected from halogen, hydroxyl, cyano, carboxyl, amino, C1-C3-alkyl, C1-C2-haloalkyl, C1-C3-haloalkoxy, C1-C4-alkoxy, C2-C3-enoxy, C2-C3-alkynoxy, C1-C2-alkylthioalkyl, C1-C2-alkylsulfinyl, C1-C2-alkylsulfonyl, C1-C4-alkoxy-C1-C2-alkyl, C1-C2-alkoxy-C1-C4-alkoxy, C1-C3-alkoxycarbonyl, C1-C2-alkylcarbonyl, N-C1 -C2-alkoxy-C-C1-C2-alkyl-carbonimide, N-hydroxy-C1-C2-alkyl-carbonimide, trifluoromethanesulfonyloxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl comprises one or two heteroatoms individually selected from N and O, and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl is unsubstituted or substituted by one, two, or three substituents independently selected from halogen, cyano, or methyl.

[0086] In a preferred embodiment, R 10Selected from halogens, hydroxyl groups, cyano groups, carboxyl groups, amino groups, C1-C3-alkyl groups, C1-C2-haloalkyl groups, C1-C3-haloalkoxy groups, C1-C4-alkoxy groups, C2-C3-enoxy groups, C2-C3-alkynoxy groups, C1-C2-alkylthioalkyl groups, C1-C2-alkylsulfinyl groups, C1-C2-alkylsulfonyl groups, C1-C2-alkoxy-C1-C2-alkyl, C1-C2-alkoxy-C1-C4-alkoxy, C1-C3-alkoxycarbonyl, C1-C2-alkylcarbonyl, N-C1-C2-alkoxy-C-C1-C2-alkyl-carbonimide, N-hydroxy-C1-C2-alkyl-carbonimide, trifluoromethylsulfonyloxy, phenyl, and 2-cyanobenzene. , 3-cyanophenyl, 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazole-1-yl], [3-(trifluoromethyl)pyrazole-1-yl], (3-cyanopyrazole-1-yl), (4-cyanopyrazole-1-yl), (5-chloropyrazole-1-yl), (4-chloropyrazole-1-yl), (3-chloropyrazole-1-yl), (5-fluoropyrazole-1-yl), (4-fluoropyrazole-1-yl), (3-fluoropyrazole-1-yl), (3,5-dimethylpyrazole-1-yl), (5-methylpyrazole-1-yl), (4-methylpyrazole-1-yl), (3-methylpyrazole-1-yl), pyrazole-1-yl, cyclopropyl, or 1-cyanocyclopropyl.

[0087] More preferably, R 10 Selected from cyano, carboxyl, chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, ethoxy, ethoxy, propoxy, allyloxy, prop-2-acetyloxy, difluoromethyl, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylthioalkyl, methylsulfinyl, methyl-sulfonyl, methoxymethyl, ethoxymethyl, 2-methoxy-ethoxymethyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetyl, propionyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, trifluoromethylsulfonyloxy, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl 2-Methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazole-1-yl], [3-(trifluoromethyl)pyrazole-1-yl], (3-cyanopyrazole-1-yl), (4-cyanopyrazole-1-yl), (5-chloropyrazole-1-yl), (4-chloropyrazole-1-yl), (3-chloropyrazole-1-yl), (5-fluoropyrazole-1-yl), (4-fluoropyrazole-1-yl), (3-fluoropyrazole-1-yl), (3,5-dimethylpyrazole-1-yl), (5-methylpyrazole-1-yl), (4-methylpyrazole-1-yl), (3-methylpyrazole-1-yl), pyrazole-1-yl, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R10 Selected from chlorine, fluorine, bromine, cyano, carboxyl, methyl, trifluoromethyl, methoxy, propoxy, allyloxy, prop-2-acetyloxy, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylthioalkyl, methylsulfinyl, methylsulfonyl, methoxymethyl, 2-methoxy-ethoxymethyl, methoxycarbonyl, acetyl, propionyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, trifluoromethyl-sulfonyloxy, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, [4-( [3-(trifluoromethyl)pyrazole-1-yl], [3-cyanopyrazole-1-yl], (4-cyanopyrazole-1-yl), (5-chloropyrazole-1-yl), (4-chloropyrazole-1-yl), (3-chloropyrazole-1-yl), (5-fluoropyrazole-1-yl), (4-fluoropyrazole-1-yl), (3-fluoropyrazole-1-yl), (3,5-dimethylpyrazole-1-yl), (5-methylpyrazole-1-yl), (4-methylpyrazole-1-yl), (3-methylpyrazole-1-yl), pyrazole-1-yl, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R 10 It is selected from chlorine, fluorine, bromine, methoxy, cyano, amino, carboxyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (5-chloropyrazol-1-yl), (4-chloropyrazol-1-yl), (3-chloropyrazol-1-yl), (5-fluoropyrazol-1-yl), (4-fluoropyrazol-1-yl), (3-fluoropyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl.

[0088] In yet another embodiment of the invention, R 10 The group is selected from halogen, cyano, amino, C1-C3-alkyl, C1-C3-alkoxy, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups comprises one heteroatom selected from N, and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by one or two substituents independently selected from: halogen, cyano, or methyl. More preferably, R 10Selected from chlorine, bromine, methyl, methoxy, cyano, amino, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, (3-cyanopyrazol-1-yl), (4-cyanopyrazol-1-yl), (3,5-dimethylpyrazol-1-yl), (5-methylpyrazol-1-yl), (4-methylpyrazol-1-yl), (3-methylpyrazol-1-yl), pyrazol-1-yl, cyclopropyl, and 1-cyanocyclopropyl. Even more preferably, R 10 Selected from chlorine, bromine, cyano, or amino groups.

[0089] In yet another embodiment of the invention, R 10 The group is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl, wherein any one of the C3-C6-cycloalkyl groups is unsubstituted or substituted by one or two substituents independently selected from halogen, cyano, or methyl. Preferably, R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl. More preferably, R 10 It is selected from cyano, chlorine, bromine, methyl, methoxy or cyclopropyl.

[0090] In one embodiment of the present invention, Z 1 The group is selected from C1-C4-alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-ynyl.

[0091] Preferably, Z 1 The group is selected from C1-C4-alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl; wherein any one of the 5- or 6-membered heteroaryl groups contains one or two heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by one, two, or three substituents independently selected from: halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, C1-C2-alkylthioalkyl, C1-C2-alkylsulfinyl, C1-C2-alkylsulfonyl, or C2-C4-ynyl. More preferably, Z1 The group is selected from C1-C4-alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl; wherein any one of the 5- or 6-membered heteroaryl groups contains one heteroatom selected from N, O, and S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, or C2-C4-alkynyl. Even more preferably, Z 1Selected from 1-methylcyclopropyl, 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluoro-4-pyridyl, 2,3-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluoro-3-pyridyl, 2,4-difluorophenyl, 2,4-difluoropyrimidin-5-yl, 2,5-difluoro-3-pyridyl, 2,5-difluoro-4-pyridyl, 2,5-difluorophenyl, 2,5-difluoropyrimidin-4-yl, 2,6-difluoro-3-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-difluoropyrimidin-4-yl, 2-chlorophenyl, 2-fluoro-3-pyridyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methyl sulfonyl-phenyl, 2-fluoro-4-pyridyl, 2-fluorophenyl, 2-fluoropyrimidin-4-yl, 2-fluoropyrimidin-5-yl, 2-furanyl, 2-methylphenyl, 2-thienyl, 3,4-difluoro-2-pyridyl, 3,4-difluorophenyl, 3,5-difluoro-2-furanyl, 3,5-difluoro-2-pyridyl, 3,5-difluoro-2-thienyl, 3,5-difluoro-4-pyridyl, 3,5-difluorophenyl, 3,5-difluoropyridazin-4-yl, 3,6-difluoro-2-pyridyl, 3,6-difluoropyridazin-4-yl, 3-chlorophenyl, 3-fluoro-2-furanyl, 3-fluoro-2-pyridyl, 3-fluoro-2-thienyl, 3-fluoro-4- -pyridyl, 3-fluorophenyl, 3-fluoropyridazin-4-yl, 3-methoxyphenyl, 3-methylphenyl, 3-thienyl, 4,5-difluoro-2-pyridyl, 4,5-difluoropyridazin-3-yl, 4,5-difluoropyrimidin-2-yl, 4,6-difluoro-2-pyridyl, 4,6-difluoro-3-pyridyl, 4,6-difluoropyridazin-3-yl, 4,6-difluoropyrimidin-2-yl, 4-chlorophenyl, 4-ethynyl-2-fluorophenyl, 4-fluoro-2-methoxyphenyl, 4-fluoro-2-methoxyphenyl, 4-fluoro-3-pyridyl, 4-fluorophenyl, 4-fluoropyridazin-3-yl, 4-fluoropyrimidin-2-yl, 4-fluoropyrimidin-5-yl, 4 -Methylphenyl, 5,6-difluoro-2-pyridyl, 5,6-difluoro-3-pyridyl, 5,6-difluoropyridazin-3-yl, 5,6-difluoropyridazin-4-yl, 5,6-difluoropyrimidin-4-yl, 5-fluoro-2-furanyl, 5-fluoro-2-pyridyl, 5-fluoro-2-thiophenyl, 5-fluoro-3-pyridyl, 5-fluoropyridazin-3-yl, 5-fluoropyridazin-4-yl, 5-fluoropyrimidin-2-yl, 5-fluoropyrimidin-4-yl, 6-fluoro-2-pyridyl, 6-fluoro-3-pyridyl, 6-fluoropyridazin-3-yl, 6-fluoropyridazin-4-yl, 6-fluoropyrimidin-4-yl, cyclobutyl, cyclohexyl, cyclopentyl, cyclopropyl, methyl, or n-propyl. Even more preferably, Z 1It is 1-methylcyclopropyl, cyclobutyl, cyclopropyl, methyl, n-propyl, phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 5-fluoro-2-furanyl, 3,5-difluoro-2-furanyl, 5-fluoro-2-thienyl, 3,5-difluoro-2-thienyl, 2-fluoro-3-pyridyl, 3-fluoro-2-pyridyl, 3-fluoro-4-pyridyl, 4-fluoro-3-pyridyl, 5-fluoro-2-pyridyl, 6-fluoro-3-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, or 4,6-difluoro-3-pyridyl.

[0092] In another embodiment of the invention, Z 1 The group is selected from phenyl, 5-membered or 6-membered heteroaryl; wherein any one of the 5-membered or 6-membered heteroaryl groups contains 1, 2 or 3 heteroatoms individually selected from N, O and S, provided that only one is selected from O or S; and wherein the phenyl and any one of the 5-membered or 6-membered heteroaryl groups are unsubstituted or substituted by 1, 2 or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-alkynyl. Preferably, Z 1 The group is selected from phenyl, or 5- or 6-membered heteroaryl; wherein each of the 5- or 6-membered heteroaryl groups contains one or two heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein the phenyl and each of the 5- or 6-membered heteroaryl groups are unsubstituted or substituted by one, two, or three substituents independently selected from: halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, C1-C2-alkylthioalkyl, C1-C2-alkylsulfinyl, C1-C2-alkylsulfonyl, or C2-C4-alkynyl. More preferably, Z 1 The group is selected from phenyl, or 5- or 6-membered heteroaryl; wherein each of the 5- or 6-membered heteroaryl groups contains one heteroatom selected from N, O, and S; and wherein the phenyl and each of the 5- or 6-membered heteroaryl groups are unsubstituted or substituted by one, two, or three substituents independently selected from: halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, or C2-C4-alkynyl. Even more preferably, Z 1The group is selected from phenyl, thienyl, furanyl, pyridyl, pyridazinyl, or pyrimidinyl; and wherein any one of the phenyl, thienyl, furanyl, pyridyl, pyridazinyl, and pyrimidinyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C1-C2-haloalkoxy, or C2-C4-alkynyl. Even more preferably, Z 1 The group is selected from phenyl, thienyl, furanyl, pyridyl, pyridazinyl, or pyrimidinyl; and wherein any one of the phenyl, thienyl, furanyl, pyridyl, pyridazinyl, and pyrimidinyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: chlorine, fluorine, C1-C2-alkyl, C1-C2-alkoxy, or C2-C4-alkynyl. Even more preferably, Z 1Selected from 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluoro-4-pyridyl, 2,3-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluoro-3-pyridyl, 2,4-difluorophenyl, 2,4-difluoropyrimidin-5-yl, 2,5-difluoro-3-pyridyl, 2,5-difluoro-4-pyridyl, 2,5-difluorophenyl, 2,5-difluoropyrimidin-4-yl, 2,6-difluoro-3-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-difluoropyrimidin-4-yl, 2-chlorophenyl, 2-fluoro-3-pyridyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methyl sulfonyl-phenyl, 2-fluoro-4-pyridyl, 2-fluorophenyl, 2-fluoropyrimidin-4-yl, 2-fluoropyrimidin-5-yl, 2-furanyl, 2-methylphenyl, 2-thienyl, 3,4-difluoro-2-pyridyl, 3,4-difluorophenyl, 3,5-difluoro-2-furanyl, 3,5-difluoro-2-pyridyl, 3,5-difluoro-2-thienyl, 3,5-difluoro-4-pyridyl, 3,5-difluorophenyl, 3,5-difluoropyridazin-4-yl, 3,6-difluoro-2-pyridyl, 3,6-difluoropyridazin-4-yl, 3-chlorophenyl, 3-fluoro-2-furanyl, 3-fluoro-2-pyridyl, 3-fluoro-2-thiazolyl Phenoyl, 3-fluoro-4-pyridyl, 3-fluorophenyl, 3-fluoropyridazin-4-yl, 3-methoxyphenyl, 3-methylphenyl, 3-thienyl, 4,5-difluoro-2-pyridyl, 4,5-difluoropyridazin-3-yl, 4,5-difluoropyrimidin-2-yl, 4,6-difluoro-2-pyridyl, 4,6-difluoro-3-pyridyl, 4,6-difluoropyridazin-3-yl, 4,6-difluoropyrimidin-2-yl, 4-chlorophenyl, 4-ethynyl-2-fluoro-phenyl, 4-fluoro-2-methoxy-phenyl, 4-fluoro-2-methoxy-phenyl, 4-fluoro-3-pyridyl, 4-fluorophenyl, 4-fluoropyridazin-3-yl, 4-fluoropyrimidin -2-yl, 4-fluoropyrimidin-5-yl, 4-methylphenyl, 5,6-difluoro-2-pyridyl, 5,6-difluoro-3-pyridyl, 5,6-difluoropyridazin-3-yl, 5,6-difluoropyridazin-4-yl, 5,6-difluoropyrimidin-4-yl, 5-fluoro-2-furanyl, 5-fluoro-2-pyridyl, 5-fluoro-2-thiophenyl, 5-fluoro-3-pyridyl, 5-fluoropyridazin-3-yl, 5-fluoropyridazin-4-yl, 5-fluoropyrimidin-2-yl, 5-fluoropyrimidin-4-yl, 6-fluoro-2-pyridyl, 6-fluoro-3-pyridyl, 6-fluoropyridazin-3-yl, 6-fluoropyridazin-4-yl, 6-fluoropyrimidin-4-yl.

[0093] In another embodiment of the invention, Z 1The group is selected from phenyl, or 5- or 6-membered heteroaryl; wherein each of the 5- or 6-membered heteroaryl groups contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein the phenyl and each of the 5- or 6-membered heteroaryl groups are unsubstituted or substituted by 1 or 2 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-alkynyl. Preferably, Z 1 The group is selected from phenyl, or 5- or 6-membered heteroaryl; wherein each of the 5- or 6-membered heteroaryl groups contains one heteroatom selected from N, O, and S; and wherein the phenyl and any of the 5- or 6-membered heteroaryl groups are unsubstituted or substituted by one or two substituents independently selected from: chlorine, fluorine, C1-C2-alkyl, C1-C2-alkoxy, or C2-C4-alkynyl. More preferably, Z 1 The aryl group is selected from phenyl, or a 5- or 6-membered heteroaryl group; wherein each of the 5- or 6-membered heteroaryl groups contains one heteroatom selected from N, O, and S; and wherein either the phenyl group or the 5- or 6-membered heteroaryl group is unsubstituted or substituted with one or two substituents independently selected from chlorine or fluorine. Even more preferably, Z 1 Selected from phenyl, 2-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 5-fluoro-2-furanyl, 3,5-difluoro-2-furanyl, 5-fluoro-2-thienyl, 3,5-difluoro-2-thienyl, 2-fluoro-3-pyridyl, 3-fluoro-2-pyridyl, 3-fluoro-4-pyridyl, 4-fluoro-3-pyridyl, 5-fluoro-2-pyridyl, 6-fluoro-3-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, or 4,6-difluoro-3-pyridyl. Even more preferably, Z 1 It is 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

[0094] In another embodiment of the invention, Z 1Selected from phenyl or 6-membered heteroaryl; wherein each of the 6-membered heteroaryl groups contains one heteroatom selected from N; and wherein each of the phenyl and 6-membered heteroaryl groups is unsubstituted or substituted by one or two substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-ynyl. Preferably, Z 1 Selected from phenyl or 6-membered heteroaryl; wherein each of the 6-membered heteroaryl groups contains one heteroatom selected from N; and wherein each of the phenyl and 6-membered heteroaryl groups is unsubstituted or substituted by one or two substituents independently selected from halogens. More preferably, Z 1 Selected from phenyl, 2-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-3-pyridyl, 3-fluoro-2-pyridyl, 3-fluoro-4-pyridyl, 4-fluoro-3-pyridyl, 5-fluoro-2-pyridyl, 6-fluoro-3-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, or 4,6-difluoro-3-pyridyl. Even more preferably, Z 1 It is 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

[0095] In one embodiment of the present invention, the compound having formula (I) can be a compound having formula (IA):

[0096] (IA)

[0097] Where R 1 R 2 R 3 R 4 R 5 R 6 R 10 Q and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from...

[0098]

[0099] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 7 R 8 and R 9It is independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, or C1-C4-haloalkyl.

[0100] Preferably, in compounds having formula (IA), R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, A2, A3, A4, A5, A6, A7, or A8, and R 7 R 8 and R 9 It is independently selected from hydrogen, halogen, methyl, or trifluoromethyl.

[0101] More preferably, in compounds having formula (IA), R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, A2, A3, A4, A5, A6, A7, or A8, and R 7 R 8 and R 9 It is hydrogen.

[0102] In embodiments of the present invention, in compounds having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from...

[0103]

[0104] The crossed lines represent bonds with C (=O) groups, and the arrows represent bonds with Z groups. 1 The bond of the group, and where R 8 and R 9 It is independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, or C1-C4-haloalkyl.

[0105] Preferably, in compounds having formula (IA), R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, A2, or A3, and R 8 and R 9 It is independently selected from hydrogen, halogen, methyl, or trifluoromethyl.

[0106] More preferably, in compounds having formula (IA), R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, A2, or A3, and R 8 and R 9 It is hydrogen.

[0107] In another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 Q, R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from...

[0108]

[0109] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of a group.

[0110] Preferably, in compounds having formula (IA), R 1 R 2 R 3 R 4 R 5 R 6 Q (Q1, Q2, Q3, Q4, and Q5), R 10 and Z 1It is as defined for compounds having formula (I) according to the invention, and A is selected from A1 or A2.

[0111] In yet another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1 or A2; and Q is selected from Q1, Q2, Q3, or Q4.

[0112] In yet another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1 or A2; and Q is selected from Q1, Q2, or Q3.

[0113] In yet another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1 or A2; and Q is Q1.

[0114] In another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, and Q is selected from Q1, Q2, Q3, or Q4.

[0115] In yet another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, and Q is selected from Q1, Q2, or Q3.

[0116] In yet another embodiment of the invention, in a compound having formula (IA), wherein R 1 R 2 R 3 R 4 R 5 R 6 R 10 and Z 1 As defined for compounds of formula (I) according to the invention, A is selected from A1, and Q is Q1.

[0117] Therefore, the present invention makes it possible to obtain compounds having formula (I) having R as defined above in all combinations / permutations. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 Q, A 1 A 2 A 3 and Z 1 .

[0118] Therefore, the present invention makes it possible to obtain compounds having formula (IA) having R as defined above in all combinations / permutations. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 Q, A, and Z 1 .

[0119] Embodiments of the present invention are provided, as listed below.

[0120] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; Q is selected from...

[0121]

[0122] The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is independently selected from R1, Q2, Q3, and Q4. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N; and R is selected from N. 7 R 8 and R 9 It is hydrogen; and R 2 and Z 1 It is as defined for compounds having formula (I) according to the invention.

[0123] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; Q is selected from...

[0124]

[0125] The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is independently selected from R1, Q2, Q3, and Q4. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; A 1Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N; where R 7 R 8 and R 9 It is hydrogen; Z 1 Selected from phenyl, or 5-membered or 6-membered heteroaryl; wherein each of the 5-membered or 6-membered heteroaryl groups contains one heteroatom selected from N, O, and S; and wherein each of the phenyl and 5-membered or 6-membered heteroaryl groups is unsubstituted or substituted by one or two substituents independently selected from: chlorine, fluorine, C1-C2-alkyl, C1-C2-alkoxy, or C2-C4-alkynyl; and R 2 It is as defined for compounds having formula (I) according to the invention.

[0126] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; Q is selected from...

[0127]

[0128] The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is independently selected from R1, Q2, Q3, and Q4. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N; where R 7 R 8and R 9 It is hydrogen; and Z 1 The aryl group is selected from phenyl, or 5-membered or 6-membered heteroaryl; wherein any one of the 5-membered or 6-membered heteroaryl groups contains one heteroatom selected from N, O and S; and wherein the phenyl and any one of the 5-membered or 6-membered heteroaryl groups are unsubstituted or substituted by one or two substituents independently selected from the following: chlorine, fluorine, C1-C2-alkyl, C1-C2-alkoxy, or C2-C4-alkynyl.

[0129] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; Q is selected from...

[0130]

[0131] The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is independently selected from R1, Q2, Q3, and Q4. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N; where R 7 R 8 and R 9 It is hydrogen; and Z 1 It is selected from phenyl or 6-membered heteroaryl; wherein any one of the 6-membered heteroaryl contains one heteroatom selected from N; and wherein either the phenyl or the 6-membered heteroaryl is unsubstituted or substituted by one or two substituents independently selected from halogens.

[0132] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; Q is selected from...

[0133]

[0134] The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is independently selected from R1, Q2, Q3, and Q4. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; where A 1 A 2 and A 3 At least two of them are selected from N; and R is selected from N. 7 R 8 and R 9 It is hydrogen; and Z 1 It is selected from 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

[0135] In embodiments of the present invention, a compound having formula (IA) may be a compound having formula (I-A1), wherein Q is Q1:

[0136] (I-A1)

[0137] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and Z 1It is as defined for compounds having formula (I), and A is as defined for compounds having formula (IA) according to the invention.

[0138] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0139]

[0140] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 8 and R 9 It is hydrogen; Q1 is unsubstituted or selected independently by one or two molecules from R. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and R 2 and Z 1 It is as defined for compounds having formula (I) according to the invention.

[0141] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0142]

[0143] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 8 and R 9 It is hydrogen; Q1 is unsubstituted or selected independently by one or two molecules from R. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and Z1 It is selected from phenyl or 6-membered heteroaryl; wherein any one of the 6-membered heteroaryl contains one heteroatom selected from N; and wherein either the phenyl or the 6-membered heteroaryl is unsubstituted or substituted by one or two substituents independently selected from halogens.

[0144] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0145]

[0146] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 8 and R 9 It is hydrogen; Q1 is unsubstituted or selected independently by one or two molecules from R. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and Z 1 It is selected from 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

[0147] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0148]

[0149] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group; Q1 is unsubstituted or substituted by one or two independently selected R groups. 10 Substituents of R, wherein R 10Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and R 2 and Z 1 It is as defined for compounds having formula (I) according to the invention.

[0150] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0151]

[0152] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 8 and R 9 It is hydrogen; Q1 is unsubstituted or selected independently by one or two molecules from R. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and Z 1 It is selected from phenyl or 6-membered heteroaryl; wherein any one of the 6-membered heteroaryl contains one heteroatom selected from N; and wherein either the phenyl or the 6-membered heteroaryl is unsubstituted or substituted by one or two substituents independently selected from halogens.

[0153] Preferably, in the compound having formula (I) according to the invention, R 1 It is a C1-C3-alkyl group; R 2 It is a C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl; R 3 It is hydrogen or C1-C3-alkyl; R 4 It is hydrogen or methyl; R 5 and R 6 Independently selected from hydrogen or C1-C3-alkyl; A is selected from...

[0154]

[0155] The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups.1 The bond of the group, and where R 8 and R 9 It is hydrogen; Q1 is unsubstituted or selected independently by one or two molecules from R. 10 Substituents of R, wherein R 10 Selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl; and Z 1 It is selected from 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

[0156] The presence of one or more possible asymmetric carbon atoms in any of the compounds of formulas (I), (IA), and (I-A1) according to the invention means that these compounds can exist in chiral isomer form (i.e., enantiomer or diastereomer).

[0157] Preferably, the compound having formula (I) according to the invention is selected from the compounds listed in any one of Tables C-1 to C-56 or the compounds listed in Table P.

[0158] More preferably, the compounds having formula (I) according to the present invention are selected from the compounds listed in Table P.

[0159] More preferably, the compound having formula (I) according to the present invention is selected from N-[2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazole-5-carboxamide, N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl]-1-(2,4-difluorophenyl)triazole-4-methyl Amide, N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl]-1-(3,5-difluoro-2-pyridinyl)triazole-4-carboxamide, or N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl]-2-(2,4-difluorophenyl)tetrazol-5-carboxamide.

[0160] Compounds having formula (I) as defined in any embodiment of the invention can be prepared as shown in schemes 1 to 17 below, wherein, unless otherwise stated, each variable is defined as above in any embodiment of the invention.

[0161] In any of the following schemes 1 to 17, the presence of one or more possible asymmetric carbon atoms in the compound having formula (I) according to the invention means that the compound can exist in chiral isomer form (i.e., enantiomer or diastereomer).

[0162] More specifically, a compound having formula (I) can be produced by a compound having formula (III) or a salt thereof (where R... 1 R 2 R 3 R 4 R 5 R 6 R 10 And Q is as defined above for compounds having formula (I) by means of compounds having formula (II) (where A) 1 A 2 A 3 and Z 1 It is prepared by the reaction as defined above for compounds having formula (I). This reaction is shown in Scheme 1.

[0163]

[0164] Option 1

[0165] In scheme 1, the compound having formula (II) (wherein A) is prepared by a method known to those skilled in the art and described, for example, in Tetrahedron [Tetrahedron] 2005, 61 (46), 10827-10852. 1 A 2 A 3 and Z 1 (As defined above for compounds having formula (I)) activated to form compounds having formula (IIa). For example, compounds having formula (IIa) (where G) 0 (It is a halogen) is formed by treating a compound having formula (II) with, for example, oxalyl chloride or thionyl chloride in the presence of a catalytic amount of N,N-dimethylformamide (DMF) in an inert solvent (such as dichloromethane (DCM) or tetrahydrofuran (THF)) at a temperature between 20°C and 100°C, preferably 25°C. Optionally, it can be formed by treating a compound having formula (III) (wherein R) in the presence of a base (such as triethylamine or pyridine). 1 R 2 R 3 R 4 R 5 R 6(and Q is as defined above for compounds having formula (I)) Treatment of compounds having formula (IIa) yields compounds having formula (I). Alternatively, compounds having formula (I) can be obtained by treating compounds having formula (II) in an inert solvent (e.g., pyridine, DMF, acetonitrile, DCM2, or THF), optionally in the presence of a base (e.g., triethylamine), at a temperature between 30°C and 180°C, with dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), or 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) to obtain activated compounds having formula (IIa) (where G is G). 0 G is as described below (Scheme 2). 01 G 02 or G 03 The compound can be prepared by reacting it with a coupling agent such as propanephosphonic anhydride (T3P) to provide a compound having formula (IIa), wherein G 0 It is as described below G 04 As described, for example, in Synthesis 2013, 45, 1569. Further reaction with an amine (or a salt thereof) of a compound having formula (III) yields a compound having formula (I).

[0166]

[0167] Option 2

[0168] Compounds having formula (II) can be produced by compounds having formula (IIb) (where A) 1 A 2 A 3 It is N and Z 1 It is as described in equation (I), and R 0(I) is a C1-C4-alkyl group and is prepared by ester hydrolysis. Various conditions can be used, such as aqueous solutions of NaOH or LiOH, and organic-water miscible solvents like THF, dimethoxyethane, methanol, or ethanol. Such ester hydrolysis is well known to those skilled in the art. Compounds having formula (IIb) can also be directly converted to compounds having formula (I) by reacting a compound having formula (III) with a compound having formula (III) in an inert solvent (such as toluene or DCM) in the presence of trimethylaluminum or a trimethylaluminum-DABCO complex. Such reactions have been reported in the literature (see Tetrahedron Lett. [Tetrahedron Letters] 1977, 4171-4174 and Tetrahedron Lett. [Tetrahedron Letters] 2006, 5767-5769 and the references cited therein).

[0169] Compounds having formulas (II) and (IIb) are commercially available or can be synthesized as described below.

[0170] Compounds having formula (III) or salts thereof (where R) 1 R 2 R 3 R 4 R 5 R 6 R 10 And Q is as defined above for compounds having formula (I) and can be obtained by those skilled in the art from nitriles having formula (IV) (where R is...). 1 R 2 R 3 R 4 R 10 Q is prepared by reacting a suitable nucleophile (such as (dimethyl sulfide)boron dihydrogen (BMS)) with a suitable aprotic solvent (such as THF) as defined above for compounds having formula (I), for example as described in J. Org. Chem. 1981, 47, 3153. Alternatively, the Grignard reagent R 5 MgBr or R 6 MgBr (where R) 5 and R 6 As defined above for compounds having formula (I), it can be added sequentially or simultaneously as a nucleophile to compounds having formula (IV) to allow the preparation of more highly substituted amines having formula (III). In inert solvents (such as diethyl ether, tert-butyl methyl ether, or cyclopentyl methyl ether), in Lewis acids (such as Ti(O-) iSuch Grignard addition to nitrile is carried out in the presence of Pr)4) (see Synlett [Synthetic Express] 2007, (4), 652-654) (Scheme 3).

[0171]

[0172] Option 3

[0173] Compounds having formula (IV) (where R) 1 R 2 R 3 R 4 R 10 Q (as defined above for compounds having formula (I)) can be prepared by those skilled in the art according to known methods. More specifically, compounds having formula (IV) and their intermediates can be prepared from compounds having formula (V), as shown in Scheme 4.

[0174]

[0175] Option 4

[0176] For example, compounds having formula (IV) (where R) 1 R 2 R 3 R 4 R 10 Q is as defined above for compounds having formula (I), and R 4 (Not hydrogen) can be produced by those skilled in the art at low temperature using a strong base (such as n-butyllithium or sodium hydride) in an inert solvent (such as THF), followed by the addition of a suitable alkylating agent R. 4 -X 0 (where X) 0 (e.g., iodomethane) will cause compounds having formula (IVa) (where R) 4 It is hydrogen and R 1 R 2 R 3 And Q is prepared by deprotonation as defined above for compounds having formula (I). Compounds having formula (IVa) (where R) 4 It is hydrogen and R 1 R 2 R 3 R 10Q (as defined above for compounds having formula (I)) can be prepared from an alcohol having formula (V) by treatment with cyanotrimethylsilane (TMSCN) in the presence of a base (such as lithium carbonate) in a nonpolar solvent (such as DCM) at a temperature between 0°C and the boiling point of the reaction mixture. Such transformations are well known in the literature under various conditions, for example as described in Org. Lett. [Organic Letters] 2008, 10, 4570 and in references therein (Scheme 4).

[0177] Compounds having formula (V) can be prepared from compounds having formula (VI), specifically from any one of compounds having formulas (VIa), (VIb), (VIc), (VId), or (VIe), as shown in Scheme 5.

[0178]

[0179]

[0180] Option 5

[0181] As shown in Scheme 5, a compound having formula (VII) (where R) will be used. 1 R 2 R 3 R 10 (R10 refers to R) 10a R 10b R 10C and R 10d ) is as defined above for compounds having formula (I), and X 01 (If it is bromine or iodine) is metallized with a suitable reagent such as a turbo Grignard reagent (isopropyl magnesium chloride-lithium chloride complex) or an alkyllithium (such as n-butyllithium) to obtain an intermediate Grignard reagent or alkyllithium reagent (M is MgX). 01 Or lithium). Such metals are inserted into CX. 01 The bonding is well known to those skilled in the art and is typically carried out at temperatures between -78°C and room temperature in an inert solvent such as an ether (e.g., tert-butyl methyl ether or THF, etc.). The solution of the metallized substance (VIIa) is then treated with a compound having formula (VI) (respectively (VIa), (VIb), (VIc), (VId), or (VIe)) to give a compound having formula (V). Similar reactions of these types have been described, for example, in WO 2012 / 102297 and Bio. Med. Chem. Lett. 2017, 27(17), 4044-4050 (X). 01(Br, n-butyllithium) and Angew. Chem. Int. Ed. [Germany's Angewandte Chemie International Edition] 2016, 55(17), 5332-5336; US 2014 / 0349990; WO 2002 / 004424; WO 2021 / 009068 (X 01 It is iodine, a Grignard reagent (isopropyl magnesium chloride-lithium chloride complex). Compounds having formulas (VI) and (VII) are commercially available or readily prepared by methods known to those skilled in the art.

[0182] Further synthesis of compounds having formula (I) involves treating a compound having formula (VIII) with a base (such as sodium hydride or n-butyllithium) in an inert solvent (such as THF), and subsequently with a compound having formula (IX) (where R... 4 It is as described in equation (I), and X 02 Alkylation of leaving groups (such as halogen, methanesulfonate or toluenesulfonate groups) to produce compounds having formula (X) (Scheme 6).

[0183]

[0184] Option 6

[0185] Then, in an inert solvent (such as THF or tert-butyl methyl ether), at a temperature between -78°C and room temperature, the compound having formula (X) (where R) is treated with a strong base (such as sodium hydride) or an alkyl lithium base (such as n-butyllithium). 1 R 2 R 3 and R 4 (As defined above for compounds having formula (I),) followed by the addition of compounds having formula (XI), namely any one of compounds having formula (XIa), (XIb), (XIc), (XId), or (XIe) (where R 10 It is as defined above for compounds having formula (I), and X 03 (Is a leaving group such as a halogen, preferably F, Cl or Br) to obtain a compound having formula (IV) (Scheme 7).

[0186]

[0187]

[0188] Option 7

[0189] As previously described in schemes 1, 2, and 3, a compound having formula (IV) is converted into a compound having formula (I). Those skilled in the art will recognize that the conversion of compound (VIII) into a compound having formula (IV) can be carried out sequentially or in the same reaction vessel, allowing for a simplified conversion of the compound having formula (VIII) into the compound having formula (IV). This is described in more detail in the preparation examples.

[0190] Compounds having formula (Ia) (where R) 1 R 2 R 3 R 5 Q, R 10 A 1 A 2 A 3 and Z 1 As described above for compounds having formula (I), and R 4 and R 6 (Is hydrogen) can also be obtained by, in the presence of a base (such as triethylamine), optionally in an inert solvent (such as ethanol or methanol), using a compound having formula (XII) (where R is hydrogen). 5 (As described above for compounds having formula (I),) the treatment of compounds having formula (VI), namely any one of compounds having formulas (VIa), (VIb), (VIc), (VId), or (VIe), yields compounds having formula (XIII). These compounds can be isolated and converted to compounds having formula (XIV) by treatment with an acid anhydride (such as trifluoroacetic anhydride) in an inert solvent (such as DCM) in the presence of a base (e.g., triethylamine). This reaction is shown in Scheme 8.

[0191]

[0192]

[0193] Option 8

[0194] Those skilled in the art will understand that compounds having formula (VI) can be converted to compounds having formula (XIV) without the separation of intermediates having formula (XIII). Such reactions (known as Henry reactions) are described in detail in the literature, such as Tetrahedron 2001, 57(6), 915-945 and the references cited therein. Compounds having formula (XIV) can be converted to compounds having formula (XV) by treatment in an inert solvent (such as THF) with compounds having formula (VIIa) (see Scheme 5), as is known to those skilled in the art as the Michael reaction of organometallic compounds with nitroolefins (Scheme 9).

[0195]

[0196] Option 9

[0197] Similar Michael addition reactions of organometallic compounds with nitroalkenes have been reported, for example, in Org. Lett. [Organic Letters] 2007, 9, 85-87. The reduction of the nitro group in a compound having formula (XV) to an amine yields a compound having formula (IIIa) (where R...). 1 R 2 R 3 R 5 R 10 Q is as defined above for compounds having formula (I), and R 4 and R 6 (If it is hydrogen) can be achieved by a variety of methods commonly known to those skilled in the art, such as Bechamp reduction, or reduction with hydrogen in the presence of a metal catalyst (Scheme 10).

[0198]

[0199] Option 10

[0200] The compound having formula (IIIa) is converted into the compound having formula (Ia) by the methods described in schemes 1 and 2.

[0201] Some compounds having formula (V) (where R) 2 (C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C1-C4-haloalkoxy, C3-C6-olefin, C3-C6-alkynoxy, C1-C4-haloalkoxy, C3-C6-cycloalkoxy, or C1-C4-alkylthioalkyl) can also be prepared as shown in Scheme 11.

[0202]

[0203]

[0204] Option 11

[0205] As shown in Scheme 11, the Vilsmeier reaction of the compound having formula (XVI) yields the compound having formula (XVIIa), when used with compound HR 2 (where R) 2 When a compound of formula (XVIIb) is treated with a base (such as K2CO3 or sodium tert-butoxide), it yields a compound of formula (XVIIb). The Wilsmeier reaction for obtaining compounds having formula (XVIIb) has been reported (see WO2008059370 and WO 2017004674; Synthesis 2013, 45(23), 3211-3227; Tetrahedron Lett. 2014, 55(33), 4568-4571; Sulfur Lett. 1986, 4(5), 175-83). Compounds having formula (VIII) can be prepared by reacting compounds having formula (XVIIb) with p-toluenesulfonylmethylisocyanate (TOSMIC) in the presence of a base (Scheme 12).

[0206]

[0207] Option 12

[0208] Such TOSMIC reactions have been reported, for example, in Synth. Comm. [Synthetic Communications] 1988, 18(18), 2331-5. Compounds having formula II are commercially available or can be synthesized as described below.

[0209] Compounds having formula (IIb), wherein A 1 A 2 A 3 It is N and Z 1 It is as described in formula (I), that is, a compound having formula (IIba).

[0210] (IIba)

[0211] It can be obtained by reacting the following reaction: a diazonium salt having the formula (XVIII)

[0212] (XVIII)

[0213] Z 1 It is as defined above under Equation I and Y - It is a counter ion, depending on the conditions under which the diazotization step takes place, for example, Cl... - Or BF4 - and compounds having the formula (XIX),

[0214] (XIX)

[0215] Where R 0 It is a C1-C6-alkyl group. This reaction can be catalyzed by various silver salts, with silver acetate being the preferred silver salt, and carried out in various solvents (e.g., THF, DMF, or toluene or mixtures thereof), typically at temperatures between 0°C and 25°C, in the presence of at least one equivalent of a base (e.g., sodium carbonate). These dipolar [3+2] cycloadditions are highly regioselective and are described, for example, in Tetrahedron [Tetrahedron] 2020, 76(14), 131063. Compounds having formula (XVIII) as defined above can be prepared from primary amines having formula (XX) by reacting with a diazotizing agent (e.g., a salt of nitrite, such as sodium nitrite). The solvent can be an aqueous solution of an acid, such as dilute hydrochloric acid or tetrafluoroborate. Counterion Y - The diazotization reaction is defined by the acid used. Diazotization is commonly used in organic synthesis, even on an industrial scale, and is known to those skilled in the art.

[0216] To reduce the risk of decomposition of the intermediate with formula (XVIII), the diazotization and cycloaddition steps can be performed sequentially without the need to separate (XVIII). This variant is also described in Tetrahedron 2020, 76(14), 131063. The chemical process is summarized in scheme 13:

[0217]

[0218] Option 13

[0219] Compounds having formula (XX) are commercially available, as are compounds having formula (XIX) (e.g., R). 0 It is methyl, as is CAS [6832-16-2]).

[0220] Very similarly, compounds having the formula (IIba) (where A)1 A 2 A 3 It is N, and Z 1 (As described in formula (I)) can be achieved by making compounds having formula (XXI):

[0221] (XXI)

[0222] Where R 0 It is a C1-C6-alkyl group and Ar 1 The compound is prepared by reacting a phenyl or p-tolyl compound with a compound having formula (XVIII) in the presence of a base (e.g., pyridine) at a temperature of -50°C to 50°C to produce a compound having formula (IIba). Such reactions have been well precedented in, for example, the following literature: Chem. Comm. 2017, 53(69), 9620-9623; Angew. Chem. Int. Ed. 2017, 56(47), 15044-15048; and J. Am. Chem. Soc. 2016, 138(44), 14609-14615. Compounds having formula (XXI) are prepared as described in the literature cited above and illustrated in the preparation examples of this application.

[0223] Alternatively, compounds having the formula (IIba) (where A) 1 A 2 and A 3 It is N and Z 1 (As defined in formula (I)) can be obtained by coupling with the following: compounds having formula (XXII),

[0224] (XXII)

[0225] Where A 1 A 2 and A 3 It is N, and R 0 As described above, it is related to boric acid derivatives having formula (XXIII).

[0226] (XXIII)

[0227] Z 1It is as defined in Formula I. This Chan-Lam type coupling reaction is typically carried out in a solvent (like dichloromethane), in the presence of a catalytic amount of a copper-based catalyst, at a mild reaction temperature, in the presence of a base (such as potassium carbonate), under atmospheric or oxygen conditions. It should be noted that compounds having formula (XXII) (where A...) 1 A 2 and A 3 (N) exists in the form of tautomerism.

[0228]

[0229] Those skilled in the art will envision that the coupling products of this reaction could be one of the positional isomers or a mixture thereof; however, when the reaction conditions are selected as described in J. Org. Chem. 2014, 79, 6703-6707, the reaction exhibits excellent regioselectivity for compounds having formula (IIba). Those skilled in the art will recognize that this Chan-Lam coupling is a general method for preparing compounds having formula (IIb). Examples are shown in the literature: compounds having formula (IIbb).

[0230] (IIbb)

[0231] Z 1 R 7 and R 0 Compounds having formulas (IIbc) and (IIbd) are as previously defined (see J. Med. Chem. [Journal of Medicinal Chemistry] 2018, 61, 8, 3370-3388 and WO 14 / 041106).

[0232] (IIbc) (IIbd)

[0233] Z 1 R 7 R 8 and R 9 It is as defined under equation (I), and R 0 It is a C1-C6-alkyl group (see WO 15 / 155626, EP 2390252) and compounds having the formula (IIbe).

[0234] (IIbe)

[0235] Z 1 R 7 R 8 and R9 It is as defined under equation (I), and R 0 It is a C1-C6-alkyl group (see J. Med. Chem. 2017, 60(14), 6166-6190, Org. Lett. 2008, 10(8), 1653-1655, and Bio. Med. Chem. Lett. 2009, 19(5), 1451-1456) as a representative example.

[0236] Used to prepare compounds having the formula (IIba) (where A) 1 A 2 and A 3 It is N, and Z 1 Another method (as defined in equation (I)) is shown in scheme 14.

[0237]

[0238] Option 14

[0239] As shown in scheme 14, the sequence begins with the diazotization of a compound having formula (XX) as previously described above, and then with a compound having formula (XXIV) in the presence of a mild base (e.g., sodium acetate) (where R... 0 The diazonium salt is treated with C1-C6 alkyl groups to produce a compound having the formula (XXV). Then, the compound having the formula (XXV) (where Z is C1-C6 alkyl) is treated with ammonia in a miscible organic solvent (e.g., THF or 2-methyltetrahydrofuran) at a temperature between 0°C and 30°C. 1 and R 0 (As previously defined), to obtain a compound having formula (XXVI). Finally, the compound having formula (XXVI) is diazotized with a salt of nitrous acid (e.g., sodium nitrite) in a slightly acidic medium (e.g., aqueous solution of acetic acid or hydrochloric acid) at a temperature between -20°C and 0°C, resulting in the spontaneous cyclization of the formed diazonium salt to a tetrazolium compound having formula (IIba). The sequence of reactions has previously been described in WO 13 / 087805.

[0240] Compounds having formula (IIb) can also be obtained by using compounds having formula (XXII).

[0241] (XXII)

[0242] Using compounds having formula (XXVII)

[0243] (XXVII)

[0244] Z 1 It is as previously described under Equation I and X 0 It is prepared by alkylation of a halogen (preferably chlorine, bromine, or iodine) in an inert aprotic or proton solvent in the presence of a base (e.g., an alkaline earth metal base, such as NaOH, KOH, LiOH, Cs₂CO₃, K₂CO₃, etc.). Such alkylation is well known to those skilled in the art and has been used in this context to prepare compounds having formula (IIb), as described, for example, in WO 14 / 168221; WO 10 / 043000; and WO 14 / 32498. Those skilled in the art will recognize that this can yield mixtures of regioisomeric compounds that can be separated by chromatographic techniques, or pure isomers can be obtained by prudent selection of conditions and additives (e.g., palladium catalysts for so-called Buchwald amination). For Z... 1 In the case of heteroaryl or aryl compounds, the SnAr reaction (with or without copper catalysis) can be used to prepare compounds having formula (IIb) (see, for example, Polyhedron 2019, 165, 22-30; US 2018 / 0170909; Org. Lett. 2022, 24(20), 3620-3625; J. Org. Chem. 2017, 82(14), 7420-7427; Chem. Comm. 2021, 57(57), 7047-7050; ACS Catalysis 2019, 9(12), 10674-10679; Synthesis 2017, 49(23)). 5120-5130; J.Org. Chem. 2019, 84(12), 8160-8167; and references cited therein).

[0245] Further compounds according to the invention can be prepared by derivatization using a key central intermediate in a later stage of synthesis. For example, compounds having formula (I) (where Q is Q1, and R...) 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z1 It is as defined above for compounds having formula (I), and X 04 Halogens, preferably bromine or chlorine, such as compounds having formula (Ia) (hereinafter) allow for additional chemical processes, such as palladium-catalyzed carbonylation, Suzuki reaction, Stille coupling, copper-catalyzed introduction of sulfonyl, haloalkyl and cyano moieties, and SnAr reaction with a variety of nucleophiles.

[0246] (Ia)

[0247] An example of such a reaction is shown in Scheme 15.

[0248]

[0249] Option 15

[0250] As shown in Scheme 15, a compound having formula (I) (where Q is Q1 and R) 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and R 10a The cyano group (i.e., compounds having formula (Ib)) can be obtained from compounds having formula (Ia) by treatment with an inorganic cyanide source (such as CuCN) in an inert solvent (such as DMF or N-methyl-2-pyrrolidone) at a temperature between 0°C and 150°C. Such reactions are well known in the literature, for example in J. Het. Chem. [Organic Heterocyclic Chemistry] 1987, 24(2), 373-6; Liebigs Ann. Chem. [Liebig's Annals of Chemistry] 1994, (10), 1049-53; and Org. Prep. Proc. Int. [International Organic Preparation and Procedures] 1985, 17(6), 391-9. Other methods for introducing the cyano group by substituting the halogen atom are known in the art, for example in Sci. Synth. [Scientific Synthesis] 2004, 19, 173-195.

[0251] Compounds having formula (I) (where Q is Q1 and R) 1 R 2 R 3 R4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and R 10a The compound is a phenyl, a 5- or 6-membered heteroaryl, or a C3-C6-cycloalkyl group, wherein any one of the 5- or 6-membered heteroaryl groups comprises 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, and C1-C4-alkoxy, i.e., a compound having formula (Id) can be prepared by the Suzuki reaction (as shown in Scheme 15), which involves, for example, reacting a compound having formula (Ia) (where X...) 04 It is a leaving group, such as chlorine, bromine or iodine) and a compound having the formula (XXVIIIa) (where Y is a leaving group) and a compound having the formula (XXVIIIa) (where Y is a leaving group) and a leaving group, such as chlorine, bromine or iodine ... b1 It can be a boron-derived functional group, such as, for example, B(OH)2 or B(OR). b1 )2, where R b1 It can be a C1-C4 alkyl group or two groups OR b1 It can form a five-membered ring with boron atoms, such as pinacol boronic acid ester. The reaction is catalyzed by a palladium-based catalyst (e.g., tetra(triphenylphosphine)-palladium or (1,1'-bis(diphenylphosphine)-ferrocene)palladium dichloride-dichloromethane (1:1 complex)) in the presence of a base (like sodium carbonate or cesium fluoride) in a solvent or solvent mixture (e.g., a mixture of 1,2-dimethoxyethane and water, or dioxane and water, or methyl THF and water), preferably under an inert atmosphere. The reaction temperature can preferably range from room temperature to the boiling point of the reaction mixture. Such Suzuki reactions are well known to those skilled in the art and have been reviewed, for example, in J. Organomet. Chem. 1999, 576, 147-168.

[0252] Alternatively, compounds having formula (Ic) can be derived from compounds having formula (XXVIIIb) (where Y... b2It is prepared by the Stieler reaction of a trialkyltin derivative (preferably tri-n-butyltin) with a compound having formula (Ia). Such a Stieler reaction is carried out in the presence of a palladium catalyst (e.g., tetrakis(triphenylphosphine)palladium(O) or (1,1'-bis(diphenylphosphine)-ferrocene)palladium dichloride-dichloromethane (1:1 complex)) in an inert solvent (e.g., DMF, acetonitrile, or dioxane), optionally in the presence of an additive (e.g., cesium fluoride, or lithium chloride), and optionally in the presence of another catalyst (e.g., copper iodide(I)). Such Stieler couplings are well known to those skilled in the art and have been described, for example, in J. Org. Chem. 2005, 70, 8601-8604; J. Org. Chem. 2009, 74, 5599-5602; and Angew. Chem. Int. Ed. 2004, 43, 1132-1136. Numerous compounds having formulas (XXVIIIa) and (XXVIIIb) are commercially available or can be prepared by those skilled in the art.

[0253] Additional compounds that can be obtained from compounds having formula (Ia) are shown in scheme 16.

[0254]

[0255] Option 16

[0256] As shown in Scheme 16, a compound having formula (I) (where Q is Q1 and R) 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and X 04The leaving group, such as chlorine, bromine, or iodine (i.e., compounds having formula (Ia)), can be treated with a compound having formula (XXIX) under Stieler reaction conditions to give a compound having formula (Id). The compound having formula (Id) can be isolated or directly hydrolyzed under aqueous acidic conditions to give a compound having formula (Ie). Such reactions are known in the literature and have been described, for example, in Synthesis 2001, (10), 1551-1555 and Tetrahedron 2001, 57(13), 2507-2514. The compound having formula (XXX) (or its salt) (wherein R is a leaving group, such as chlorine, ethanol, THF, methyl) can be treated with a compound having formula (XXX) (or its salt) in the presence of an inorganic base (such as sodium carbonate or potassium carbonate) or an organic base (such as triethylamine). 13 Treating a compound having formula (Ie) with hydrogen or C1-C4-alkyl can convert the compound having formula (Ie) into a compound having formula (If) (where Q is Q1, and R is...). 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and R 13 (It is hydrogen or C1-C4-alkyl). Many examples of preparations of such oximes are known in the literature (see, for example, Molecules [Molecules] 2019, 24, 2470 and references cited therein), and are well known to those skilled in the art.

[0257] It can be made from a compound having formula (I) (where Q is Q1 and R) 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and X 04 The other compound is prepared by removing a leaving group, such as chlorine, bromine or iodine, i.e., a compound having formula (Ia) (Scheme 17).

[0258]

[0259] Option 17

[0260] As shown in Scheme 17, a compound having formula (Ia) can be carbonylated to obtain a compound having formula (I), i.e., having R 14 C1-C4-alkyl compounds having the formula (Ig), where Q is Q1 and R 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 This is as defined above for compounds having formula (I). In such alkoxycarbonylation, a compound having formula (Ia) is reacted with carbon monoxide, typically under pressure, in the presence of a metal catalyst such as palladium catalyst (e.g., palladium(II) acetate, [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (Pd(dppf)Cl2), bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) or bis(diphenylphosphine)propane]palladium(II) dichloride (PdCl2(dippp))), optionally in the presence of a phosphine ligand (such as triphenylphosphine or 1,1'-bis(diphenylphosphine)ferrocene), in an alcohol (R 14 OH) (typically methanol or ethanol) (wherein R 14The reaction is carried out in the presence of (C1-C4-alkyl) alkyl groups, optionally in the presence of a co-solvent (e.g., toluene, dioxane, or DMF), and preferably in the presence of a base (e.g., trimethylamine), at a temperature between 20°C and 200°C, preferably between 50°C and 180°C. Such carbonylation reactions are well known to those skilled in the art and are also well known in the literature (see J. Org. Chem. [Journal of Organic Chemistry] 2008, 73, 7102-7107 and the references cited therein). Compounds of this formula (Ig) can be readily saponified to compounds of formula (Ih) under conditions known to those skilled in the art (e.g., at room temperature or up to reflux, in aqueous solutions of sodium hydroxide, potassium hydroxide, or lithium hydroxide in methanol, ethanol, THF, or dioxane). Alternatively, treatment of ester compounds having formula (Ii) with a halide anion (preferably a chloride anion derived from, for example, lithium chloride (or alternatively, sodium chloride or potassium chloride)) in a solvent (such as DMF, N,N-dimethylacetamide, or N-methyl-2-pyrrolidone) can also produce carboxylic acid compounds having formula (Ih). The reaction temperature range for this O-demethylation is preferably from 20°C to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Compounds having formula (Ih) can be converted into amides having formula (I), i.e., compounds having formula (Ii), wherein R... 15 and R 16 Independently, it is hydrogen or C1-C4-alkyl, where Q is Q1, and R 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 This is as defined for compounds having formula (I). Such reactions typically involve activating the carboxyl group, followed by compound R. 15 R 16 NH treatment or the use of coupling agents in the presence of formula R 15 R 16 The NH compounds are treated for direct conversion from acid to amide. These methods have been discussed above in schemes 1 and 2.

[0261] Other compounds having formula (Ii) can be transformed into compounds having formula (I) through the so-called Curtius rearrangement, i.e., compounds having formula (Ij), where R 9 It is an amino group; Q is Q1; and R1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 As defined above for compounds having formula (I). In the Curtes rearrangement, compounds having formula (Ii) are treated with an organo-azide in the presence of a suitable base and optionally in the presence or absence of a Lewis acid in an inert solvent at a temperature between 50°C and 200°C. Examples of organo-azides include TMSN3, sodium azide, diphenylphosphino azide, or toluenesulfonyl azide, and suitable solvents may be toluene, xylene, THF, or acetonitrile. Examples of suitable Lewis acids may include, in particular, Zn(OTf)2. The isocyanates formed in the rearrangement are reacted with water to form carbamates, which are then decarboxylated under the reaction conditions to the corresponding amines having formula (Ij). Alternatively, these reactions may be carried out in an alcohol (e.g., tert-butanol), thereby allowing the isolation of tert-butyl carbamate. These can then be further cleaved in a separate step with an acid (e.g., trifluoroacetic acid) by methods known to those skilled in the art to produce compounds having formula (Ij). Examples of such Coultides reactions have been reported, for example, in Org. Lett. [Organic Letters] 2005, 7, 4107-4110; J. Med. Chem. [Journal of Medicinal Chemistry] 2006, 49(12), 3614-3627; and Tetrahedron [Tetrahedron] 1974, 30, 2151-2157. According to the amidation method described above, a compound having formula (Ij) thus obtained can be amidated to a compound having formula (Ik) by treatment with a compound having formula (XXXI) (where Q is Q1, and R...). 1 R 2 R 3 R 4 R 5 R 6 R 10 A 1 A 2 A 3 and Z 1 It is as defined above for compounds having formula (I), and R 18It is a C1-C4-alkyl group. Those skilled in the art will recognize that this chemical process can be applied to any compound having formula (I), where Q is Q1, Q2, Q3, Q4, or Q5, at any position on the heterocycle having formula Q (i.e., R). 10 When the following group is a leaving group such as a halogen atom.

[0262] A compound having formula (I) as defined in any embodiment of the invention can be converted into another compound as defined in any embodiment of the invention in a manner known per se by replacing one or more substituents of the starting compound in a conventional manner with another substituent according to the invention. Those skilled in the art will also understand that a compound having formula (I) can be further converted into other derivatives having formula (I) by, for example, alkylation, nucleophilic substitution, elimination, C / C bond formation reactions in the presence of a metal catalyst, heteroatom-carbon bond formation in the presence of a metal catalyst, oxidation, and reduction.

[0263] Depending on the chosen reaction conditions and starting materials appropriate to the specific circumstances, it may be possible, for example, to replace only one substituent with another substituent according to the invention in a single reaction step, or to replace multiple substituents with other substituents according to the invention in the same reaction step.

[0264] Salts of compounds having formula (I) can be prepared in ways known per se. Thus, for example, acid addition salts of compounds having formula (I) are obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with a base are obtained by treatment with a suitable base or a suitable ion exchange reagent.

[0265] Salts of compounds having formula (I) can be converted in a manner known per se into other salts of compounds having formula (I), acid addition salts, for example, into other acid addition salts, such as by treating salts of inorganic acids (e.g., hydrochlorides) in a suitable solvent with a suitable metal salt of the acid (e.g., a salt of sodium, barium, or silver, e.g., silver acetate), in which the inorganic salt (e.g., silver chloride) formed is insoluble and thus precipitates out of the reaction mixture.

[0266] Compounds having formula (I) and, where appropriate, their tautomers (in each case, in free form or in salt form) can exist in one of the possible isomers or in mixtures of these isomers, for example, in the form of pure isomers (such as enantiomers and / or diastereomers) or in the form of mixtures of isomers (such as mixtures of enantiomers, e.g., racemic mixtures; mixtures of diastereomers or mixtures of racemic mixtures), depending on the number of asymmetric carbon atoms present in the molecule, the absolute and relative configurations and / or depending on the configuration of the non-aromatic double bonds present in the molecule; the present invention relates to pure isomers and all possible mixtures of isomers, and should be understood in this sense in every context, even in every case where stereochemical details are not specifically mentioned.

[0267] A mixture of diastereomers or racemates of compounds of formula (I) in free or salt form (their acquisition may depend on the selected starting materials and procedures) can be isolated into pure diastereomers or racemates in a known manner, based on the physicochemical differences of these components, for example by fractional crystallization, distillation and / or chromatography.

[0268] Enantiomer mixtures (such as racemates) that can be obtained in a similar manner can be resolved into optical enantiomers by known methods, such as by recrystallization from an optically active solvent; by chromatography on a chiral adsorbent, such as high-performance liquid chromatography (HPLC) on acetylcellulose; by cleavage with a specific immobilized enzyme using suitable microorganisms; by forming a containing compound, such as using a chiral crown ether, in which only one enantiomer is complexed; or by conversion into salts of diastereomers, such as by reacting the basic final product racemate with an optically active acid (such as a carboxylic acid, such as camphoric acid, tartaric acid, or malic acid, or a sulfonic acid, such as camphorsulfonic acid), and the diastereomer mixtures that can be obtained in this manner can be separated, for example by fractional crystallization based on their different solubilities, to obtain diastereomers from which the desired enantiomers can be freed by the action of suitable reagents (such as basic reagents).

[0269] Pure diastereomers or enantiomers can be obtained according to the invention, not only by separating a suitable mixture of isomers, but also by methods of commonly known diastereoselective or enantiomeric synthesis, for example by using starting materials with suitable stereochemistry according to the invention.

[0270] If individual components have different biological activities, it is advantageous to isolate or synthesize biologically more effective isomers in each case, such as enantiomers or diastereomers or mixtures of isomers, such as mixtures of enantiomers or mixtures of diastereomers.

[0271] As an example, compounds having more than one asymmetric carbon atom can exist in diastereomers, which can optionally be separated using, for example, supercritical fluid chromatography (SFC) with a chiral column. Such diastereomers can exhibit different antifungal activity characteristics, but all isomers and diastereomers form part of this invention.

[0272] The compounds of formula (I) of the present invention exhibit at least three asymmetric carbon atoms. The relationship between the enantiomers and diastereomers of the compounds of formula (I) is shown below.

[0273] Those skilled in the art are well aware of the diastereomers and enantiomers of the above having formula (I) (where R) 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 A 1 A 2 A 3 Q and Z 1 (as defined for formula (I)) is within the scope of this invention.

[0274] Compounds having formula (I) have at least two chiral carbon atoms (stereocenters, where the asterisk (…) (The indicator carbon atom) makes four stereoisomers available. These four stereoisomers consist of two sets of enantiomers.

[0275] (I)

[0276] For compounds having formula (I), where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 A 1 A 2 A 3 Q and Z 1 It is as defined for compounds having formula (I), where R 4 It is not hydrogen, and R is present in it. 5and R 6 It is not hydrogen. The relationship between enantiomers and diastereomers is shown below.

[0277]

[0278] Those skilled in the art are well aware of the diastereomers and enantiomers of the above having formula (I) (where R) 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 A 1 A 2 A 3 Q and Z 1 (as defined for formula (I)) is within the scope of this invention.

[0279] Furthermore, those skilled in the art are well aware that the aforementioned diastereomers and enantiomers are suitable for compounds having formula (IA) and formula (I-A1) (wherein R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 Q and Z 1 (As defined for formula (I), and where A is as defined for compounds having formula (IA)) is within the scope of this invention.

[0280] Compounds having formula (I) and, where appropriate, their tautomers (in each case, in free or salt form) can also be obtained as hydrates and / or include other solvents, such as those that can be used to crystallize compounds that exist in solid form.

[0281] As indicated, surprisingly, it has now been found that, for practical purposes, the compounds of formula (I) of the present invention have a very favorable level of bioactivity for protecting plants against diseases caused by fungi.

[0282] Compounds of formula (I) according to the present invention can be used in the agricultural sector and related application fields as active ingredients, for example, for controlling plant pests, or for controlling putrefactive microorganisms or potentially harmful organisms on non-living materials. These novel compounds are characterized by excellent activity at low application rates, good plant tolerance, and environmental safety. They have very useful therapeutic, preventative, and systemic properties and can be used to protect many cultivated plants. Compounds of formula (I) can be used to inhibit or destroy pests appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various useful plant crops, while also protecting, for example, later-growing plant parts from plant pathogenic microorganisms.

[0283] The present invention further relates to a method for controlling or preventing infection of microbially susceptible plants or plant propagation material and / or harvested food crops by treating plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound having formula (I) according to the invention is applied to these plants, parts thereof or the site thereof.

[0284] Compounds having formula (I) according to the invention can also be used as fungicides. As used herein, the term "fungicide" means a compound that controls, alters, or prevents fungal growth. The term "fungicide effective amount" in use means, when used, the amount of such compound or combination of such compounds that can affect fungal growth. Controlling or altering effects include all deviations from natural development, such as killing, inhibiting, etc., and prevention includes the formation of barriers or other defenses within or on the plant to prevent fungal infection.

[0285] It is also possible to use compounds of formula (I) according to the invention as seed dressings for treating plant propagation material (e.g., seeds, fruits, tubers, or grains) or plant cuttings to protect against fungal infections and against plant pathogenic fungi present in the soil. Propagation material can be treated with a composition containing a compound of formula (I) before planting: for example, seed dressing can be applied before sowing. The active compound of formula (I) can also be applied to grains (coating) by impregnating seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when planting the propagation material, for example, by applying it to the furrows of the seeds during sowing. The invention also relates to such methods of treating plant propagation material, and to plant propagation material treated in this way.

[0286] Furthermore, the compounds of formula (I) according to the present invention can be used to control fungi in relevant fields, such as in the protection of industrial materials (including wood and wood-related technical products), in food storage, and in hygiene management.

[0287] In addition, the present invention can also be used to protect non-living materials (e.g., wood, wall panels, and coatings) from fungal invasion.

[0288] The compounds of formula (I) according to the present invention are effective against pathogenic fungi and fungal vectors, as well as plant pathogenic bacteria and viruses. The fungi and fungal vectors that cause these diseases, as well as the plant pathogenic bacteria and viruses, include, for example: *Absidia corymbifera*, *Alternaria* species, *Aphanomyces* species, *Ascochyta* species, *Aspergillus* species (including *Aspergillus flavus*, *Aspergillus fumigatus*, *Aspergillus nidulans*, *Aspergillus niger*, and *Aspergillus terrus*), *Aureobasidium* species (including *Aureobasidium pullulans*), *Blastomyces dermatitidis*, *Blumeria graminis*, *Bremia lactucae*, and *Botryosphaeria* species. *Botrytis* spp. (including *Botrytis dothidea*, *Botrytis obtusa*), *Botrytis* spp. (including *Botrytis cinerea*), *Candida* spp. (including *Candida albicans*, *Candida glabrata*, *Candida krusei*, *Candida lusitaniae*, *Candida parapsilosis*, *Candida tropicalis*), *Cephaloascus fragrans*, *Ceratocystis* spp., *Cercospora* spp. (including *Cercospora arachidicola*), *Cercosporidium personatum*, and *Cladosporium* spp. *Claviceps purpurea*, *Coccidioides immitis*, *Cochliobolus* species, *Colletotrichum* species (including *C. musae*), and *Corynespora* species.(Including *Corynespora cassiicola*), *Cryptococcus neoformans*, *Diaporthe* species (including *Diaporthe miriciae* (also known as *Diaporthe ueckeri* or *Diaporthe ueckerae*)), *Didymella* species, *Drechslera* species, *Elsinoe* species, *Epidermophyton* species, *Erwinia amylovora*, *Erysiphe* species (including *E. cichoracearum*), *Eutypa lata*, *Fusarium* species.) (including *Fusarium culmorum*, *Fusarium graminearum*, *Fusarium langsethiae*, *Fusarium moniliforme*, *Fusarium oxysporum*, *Fusarium proliferatum*, *Fusarium subglutinans*, *Fusarium solani*), *Gaeumannomyces graminis*, *Gibberella fujikuroi*, *Gloeodes pomigena*, *Gloeosporium musarum*, *Glomerella cingulate*, *Guignardia bidwellii*, *Gymnosporangium juniperi-virginianae*, and species of *Helminthosporium*.) spp.), species of the genus *Hemileia* spp., and species of the genus *Histoplasma* spp. (including *Histoplasma capsulatum*).* *Capsulatum*, *Laetisaria fuciformis*, *Leptographium lindbergi*, *Leveillula taurica*, *Lophodermium seditiosum*, *Microdochium nivale*, *Microsporum* spp., *Monilinia* spp., *Mucor* spp., *Mycosphaerella* spp. (including *M. graminicola*, *M. pomi*), *Oncobasidium theobromaeon*, *Ophiostoma piceae*, *Paracoccidioides* spp., and *Penicillium* spp. (including *Penicillium fingernail*). *P. italicum*, *Petriellidium* spp., *Peronosclerospora* spp. (including *Peronosclerospora maydis*, *Peronosclerospora philippinensis*, and *Peronospora sorghi*), *Phaeosphaeria nodorum*, *Phakopsora pachyrhizi*, *Phellinus igniarus*, *Phialophora* spp., *Phomaspp.*, *Phomopsis viticola*, *Phytophthora* spp. (including *P. infestans*), and *Plasmopara*. spp. (including *P. halstedii*, *P. viticola*), species of *Pleospora* spp., and species of *Podosphaera* spp. (including *P. white podosphaera*).* *Lycotricha*, *Polymyxa graminis*, *Polymyxa betae*, *Pseudocercosporella herpotrichoides*, *Pseudomonas* spp., *Pseudoperonospora* spp. (including *P. cubensis*, *P. humuli*), *Pseudopeziza tracheiphila*, *Puccinia* spp. (including *P. hordei*, *P. recondita*, *P. striiformis*, *P. triticina*), *Pyrenopeziza* spp., and *Pyrenophora* spp. spp.), *Pyricularia* spp. (including *P. oryzae*), *Pythium* spp. (including *P. ultimum*), *Ramularia* spp., *Rhizoctonia* spp., *Rhizomucor pusillus*, *Rhizopus arrhizus*, *Rhynchosporium* spp., *Scedosporium* spp. (including *S. apiospermum* and *S. prolificans*), *Schizothyrium pomi*, *Sclerotinia* spp., *Sclerotium* spp., and *Septoria* spp. (including *S. nodorum*, *S. tritici*, *Sphaerotheca macularis*, *Sphaerotheca fusca* (*Sphaerotheca fuliginea*), *Sporothorix* spp., *Stagonospora nodorum*, and *Stemphylium* spp.)* *Stereum hirsutum*, *Thanatephorus cucumeris*, *Thielaviopsis basicola*, *Tilletia* spp., *Trichoderma* spp. (including *T. harzianum*, *T. pseudokoningii*, and *T. viride*), *Trichophyton* spp., *Typhula* spp., *Uncinula necator*, *Urocystis* spp., *Ustilago* spp., *Venturia* spp. (including *V. inaequalis*), *Verticillium* spp., and *Xanthomonas* spp.).

[0289] The compounds of formula (I) according to the present invention can be used, for example, for lawns, ornamental plants such as flowers, shrubs, broad-leaved trees or evergreens such as conifers, and tree injection, pest management, etc.

[0290] Within the scope of this invention, the target crops and / or useful plants to be protected typically include perennial and annual crops, such as berry plants, such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals, such as barley, maize, millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants, such as cotton, flax, hemp, jute, and sisal; field crops, such as sugar beets and forage beets, coffee beans, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea, and tobacco; fruit trees, such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses, such as Bermuda grass, bluegrass, benjamin grass, centipede grass, sedge, and black clover. Wheatgrass, St. Augustine grass, and Zoysia japonica; herbs such as basil, borage, chives, coriander, lavender, Angelica pubescens, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm trees such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cacao, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melons, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and grapevines such as grapes.

[0291] The term "useful plant" should be understood to also include useful plants that have developed tolerance to herbicides (like bromonazine) or herbicide classes (such as HPPD inhibitors, ALS inhibitors, such as flusulfuron, fluprosulfuron, and triflusulfuron, EPSPS (5-enol-acetone-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthase) inhibitors, or PPO (protoporphyrinogen oxidase) inhibitors) through conventional breeding methods or genetic engineering. An example of a crop that has been conditioned to tolerate imidazolinones (e.g., methoxyfenozide) through conventional breeding methods (mutation) is Clearfield® Summer Canola (Canola). Examples of crops that have been conditioned to tolerate herbicides or herbicide classes through genetic engineering include glyphosate-resistant and glufosinate-resistant maize varieties commercially available under the trademarks RoundupReady®, Herculex I®, and LibertyLink®.

[0292] The term "useful plant" should be understood to also include useful plants that have been transformed by the use of recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to come from toxin-producing bacteria, especially those of the genus Bacillus.

[0293] Examples of such plants are: YieldGard® (a maize variety expressing CryIA(b) toxin); YieldGardRootworm® (a maize variety expressing CryIIIB(b1) toxin); YieldGard Plus® (a maize variety expressing both CryIA(b) and CryIIIB(b1) toxins); Starlink® (a maize variety expressing Cry9(c) toxin); Herculex I® (a maize variety expressing CryIF(a2) toxin and the enzyme phosphatidinium N-acetyltransferase (PAT) for acquiring tolerance to the herbicide glufosinate-ammonium); NuCOTN 33B® (a cotton variety expressing CryIA(c) toxin); Bollgard I® (a cotton variety expressing CryIA(c) toxin); Bollgard II® (cotton variety expressing CryIA(c) and CryIIA(b) toxins); VICOT® (cotton variety expressing VIP toxin); NewLeaf® (potato variety expressing CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate resistance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait), and Protecta®.

[0294] The term "crop" should be understood to also include crop plants that have been transformed using recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to originate from toxin-producing bacteria, particularly those of the genus Bacillus.

[0295] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from *Bacillus cereus* or *Bacillus japonicus*; or insecticidal proteins from *Bacillus thuringiensis*, such as δ-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from nematode-parasitic bacteria, such as species of *Photorhabdus* spp. or species of *Xenorhabdus* spp., such as *Photorhabdus luminescens* and *Xenorhabdus*. (nematophilus); toxins produced by animals, such as scorpion venom, spider venom, bee venom, and other insect-specific neurotoxins; toxins produced by fungi, such as streptotoxins; lectins, such as pea lectin, barley lectin, or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitors, serine inhibitors, potato glycoproteins, cystatin, and papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize-RIP, absinthecin, loofah seed toxin, saponin toxin, or cassia root toxin; steroid metabolic enzymes, such as 3-hydroxysteroid oxidase, decidual steroid-UDP-glycosyltransferase, cholesterol oxidase, decidualin inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0296] Furthermore, in the context of this invention, δ-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vip) (e.g., Vip1, Vip2, Vip3, or Vip3A) should be understood to obviously also include mixed toxins, truncated toxins, and modified toxins. Mixed toxins are generated through novel recombination of different combinations of the different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are substituted. In such amino acid substitutions, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, as in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 2003 / 018810).

[0297] Examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-0374753, WO93 / 07278, WO 95 / 34656, EP 0427529, EP 0451878 and WO 03 / 052073.

[0298] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described in, for example, the disclosures mentioned above. CryI type deoxyribonucleic acid and its preparation are known from, for example, WO 95 / 34656, EP 0367474, EP 0401979 and WO 90 / 13651.

[0299] The toxins contained in genetically modified plants make them resistant to harmful insects. These insects can exist in any insect taxonomy but are particularly common in beetles (Coleoptera), dipterans (Diptera), and moths (Lepidoptera).

[0300] Transgenic plants containing one or more genes encoding resistance to insecticides and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (a maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (a maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (a maize variety expressing both Cry1Ab and Cry3Bb1 toxins); Starlink® (a maize variety expressing Cry9C toxin); Herculex I® (a maize variety expressing Cry1Fa2 toxin and the enzyme phosphatidylcholine N-acetyltransferase (PAT) for acquiring tolerance to the herbicide glufosinate); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard® and Agrisure® GT. Advantage (GA21 glyphosate resistance trait), Agrisure® CBAdvantage (Bt11 corn borer (CB) trait), and Protecta®.

[0301] Other examples of such genetically modified crops are:

[0302] 1. Bt11 maize, from Syngenta Seeds SAS, Chemin del 'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. A genetically modified maize variety that expresses a truncated Cry1Ab toxin to resist the European corn borer (corn borer and mealybug). Bt11 maize is also genetically modified to express the PAT enzyme to gain tolerance to the herbicide glufosinate.

[0303] 2. Bt176 maize, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. A genetically modified maize variety that expresses the Cry1Ab toxin transgenically, making it resistant to the European corn borer (corn borer and mealybug). Bt176 maize is also transgenically expressed with PAT enzyme to gain tolerance to the herbicide glufosinate-ammonium.

[0304] 3. MIR604 maize, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. This is a transgenic maize plant resistant to insects by expressing a modified Cry3A toxin. This toxin is modified by inserting a cathepsin-G-protease recognition sequence, Cry3A055. The preparation of this type of transgenic maize plant is described in WO 2003 / 018810.

[0305] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0306] 5. IPC 531 cotton, from Monsanto Europe, 270-272 Teflon Boulevard, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0307] 6.1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, Registry No. C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F to acquire resistance to certain lepidopteran insects and expressing the PAT protein to acquire tolerance to the herbicide glufosinate.

[0308] 7. NK603 × MON 810 maize, from Monsanto Europe, 270-272 Boulevard de Teveren, B 1150 Brussels, Belgium, Registry No. C / GB / 02 / M3 / 03. This hybrid maize variety was created by crossing the genetically modified cultivar NK603 with MON 810, using conventionally bred hybrid maize. NK603 × MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, making it resistant to the herbicide Roundup® (containing glyphosate), and also contains the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. Kurstak, making it resistant to certain lepidopteran insects, including the European corn borer.

[0309] The compounds of formula (I) according to the present invention can be used to control or prevent plant pathogenic diseases, especially plant pathogenic fungi, particularly plant pathogenic fungi on soybean plants. In one embodiment, such soybean plants are genetically modified soybean plants.

[0310] In one embodiment, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants are, but are not limited to, Intacta®, Intacta®2, Intacta® Roundup Ready™ 2 Pro (Intacta®RR2 PRO), Intacta®2 Xtend™, Cultivance, Conkesta soybean, Conkesta Enlist E3™ soybean, Enlist™ soybean, Enlist E3™ soybean, Roundup Ready™ soybean, Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, and Plenish™.

[0311] Transgenic soybean plants expressing toxins such as insecticidal proteins like delta-endotoxins (e.g., Cry1Ac (Cry1Ac Bt protein)). Therefore, this can include transgenic soybean plants comprising: event MON87701 (disclosed in WO 2009 / 064652), event MON87701 × MON89788 (disclosed in WO 2014 / 170327, e.g., as Intacta RR2PRO). ®Soybeans available for commercial purchase), Event MON87751 (disclosed in WO 2014 / 201235), Event DAS-44406-6 (e.g., as Enlist E3) TM Commercially available, DAS-44406-6, disclosed in WO 2012 / 075426, or event DAS-81419-2 (described in WO 2013 / 016527, for example, as Conkesta) TM Soybeans are commercially available); Event DAS-81419-2 × DAS-44406-6 (e.g., as Conkesta™ Enlist E3™ soybeans are commercially available).

[0312] In addition, such a list of genetically modified events is provided by the U.S. Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on its World Wide Web website at aphis.usda.gov.

[0313] The compounds of formula (I) according to the present invention can be used to control or prevent plant pathogenic diseases, especially plant pathogenic fungi, such as *Alternaria* species on fruits, vegetables and potatoes; *Botrytis cinerea* on strawberries, tomatoes, sunflowers, legumes, vegetables and grapes; *Rhizoctonia solani* on potatoes and vegetables; *Uncaria rhynchophylla* on grapes; *Cladosporium cucumerinum*, *Didymella bryoniae*, powdery mildew fungus and *Glomerella lagenarium* on cucurbits; *Powdery mildew fungus* on cucurbits and *Solanum* crops; *Fusarium* species on cereals; *Leptosphaeria* species on cereals; and *Zymoseptoria* species on cereals.

[0314] Compounds having formula (I) and compositions comprising said compound are suitable for controlling the following fungal diseases on soybeans and genetically modified soybeans (e.g., Bt soybeans): *Alternaria* species (Alternaria leaf spot); *Cercospora* species (Cercospora leaf spot), such as *Cercospora sojina* or *Cercospora kikuchii*; *Anthracnose* species (sexual form: *Glomerella*) (anthracnose), such as *Anthracnose scutellarioides* or *Colletotrichum gloeosporioides*; *Cladosporium multiflorum* (leaf spot); *Dematophora white-striped*. *Rosa necatrix* (sexual form: *Rosellinianecatrix*) (root rot and stem rot); *Rosa necatrix* species, such as *Rosa necatrix* (also known as *Rosa necatrix* or *Rosa necatrix*) (damping-off); *Fusarium* species (sexual form: *Gibberella*) (wilt, root rot, or stem rot), such as *Fusarium tucumaniae* and *Fusarium brasiliense* (each causing sudden death syndrome in soybeans); *Macrophomina phaseolina* (synonym *Macrophomina phaseoli*) (root rot and stem rot); *Microsphaera diffusa* (powdery mildew); *Downy mildew* species (downy mildew), such as *P. manshurica*; *P. manshurica* and *P. manshurica* rust fungi. *Meibomiae* (soybean rust); *Pythium* species, such as *P. phaseoli* (sex form: *Diaporthephaseolorum*); *Pythium* species (damping-off); *Phytophthora* species (wilt, root rot, leaf rot, fruit rot, and stem rot), such as *P. megasperma* (synonym *P. sojae*); *Rhizoctonia* species, such as *Rhizoctonia solani* (root rot and stem rot); *Sclerotium* species (stem rot or white mold); *Synonyx* species, such as *Synonyx bean* (brown spot); *S. rolfsii* (synonym *Athelia rolfsii*); *Rhizoctonia* species (black root rot).

[0315] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

[0316] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0317] The term "plant propagation material" should be understood to refer to the reproductive parts of a plant, such as seeds, which can be used for plant propagation, as well as nutrient materials, such as cuttings or tubers (e.g., potatoes). References may include, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. References may also include germinating plants and young plants that will be transplanted after germination or emergence. These young plants may be protected before transplanting by complete or partial treatment with maceration. Preferably, "plant propagation material" should be understood to mean seeds.

[0318] The compounds of formula (I) according to the invention can be used in their unmodified form, or preferably, in conjunction with adjuvants conventionally used in the field of formulations. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coated pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules, and also capsules, for example, in polymeric forms. The method of application, such as spraying, atomizing, dusting, spreading, smearing, or watering, is selected according to the intended purpose and the prevailing environment for the type of composition. The composition may also contain additional adjuvants, such as stabilizers, defoamers, viscosity modifiers, binders, or thickeners, in conjunction with fertilizers, micronutrient donors, or other formulations used to achieve specific effects.

[0319] Suitable carriers and adjuvants, for example, for agricultural use, can be solid or liquid and are substances useful in formulation techniques, such as natural or recycled minerals, solvents, dispersions, wetting agents, thickeners, binders, or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0320] Suspension concentrates are aqueous formulations in which finely dispersed solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents to enhance activity, as well as antifoamers and crystal growth inhibitors. In use, these concentrates are diluted in water and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0321] Wettable powders are finely dispersed granules that are easily dispersed in water or other liquid carriers. These granules contain active ingredients retained in a solid matrix. Typical solid matrices include bleaching clay, kaolin, silica, and other easily wettable organic or inorganic solids. Wettable powders typically contain 5% to 95% active ingredient plus small amounts of wetting agents, dispersants, or emulsifiers.

[0322] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist entirely of an active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, heavy aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0323] Granular formulations consist of both extrudates and coarser granules, and are typically applied undiluted to the area requiring treatment. Typical carriers used in granular formulations include sand, bleaching clay, attapulgite clay, bentonite, montmorillonite, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesium oxide, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic absorbent active compounds or materials that can be coated with active compounds. Granular formulations typically contain 5% to 25% of the active ingredient, which may include surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions, or vegetable oils; and / or binders such as dextrin, gums, or synthetic resins.

[0324] Dust powder is a free-flowing mixture of active ingredients and finely dispersed solids (such as talc, clay, flour, and other organic and inorganic solids that serve as dispersants and carriers).

[0325] Microcapsules are typically droplets or particles of active ingredient encapsulated within an inert, porous shell that allows the encapsulated material to escape into the environment at a controlled rate. The diameter of the encapsulated droplets typically ranges from 1 to 50 micrometers. The encapsulated liquid typically constitutes 50% to 95% of the capsule's weight and may contain a solvent in addition to the active compound. The encapsulated particles are typically porous particles, with a porous membrane sealing the particle pores, retaining the active species in liquid form within the particle pores. The particle diameter typically ranges from 1 millimeter to 1 centimeter, and preferably from 1 millimeter to 2 millimeters. The particles are formed by extrusion, aggregation, or spheroidization, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and particulate carbon. Shell or membrane materials include natural and synthetic rubbers, fibrous materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0326] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalene, xylene, and other organic solvents, in which the active ingredient is completely dissolved at the desired concentration. Pressurized sprays can also be used, in which the active ingredient is dispersed in a finely dispersed form due to the evaporation of a low-boiling-point dispersant solvent carrier.

[0327] Suitable agricultural adjuvants and carriers useful for formulating the compositions of the present invention among the above-described formulation types are well known to those skilled in the art.

[0328] Suitable liquid carriers include, for example, water, toluene, xylene, naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosin ester, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl... Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol (diproxitol), alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl diacetate, glyceryl monoester Acetates, triacetin, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropylidene acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, stearic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, benzene Phenols, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin wax, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols (such as pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc.), ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone. Water is usually the preferred carrier for diluting the concentrate.

[0329] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, lime, calcium carbonate, bentonite, bleaching clay, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder, and lignin.

[0330] A wide range of surfactants are advantageously used in the liquid and solid compositions, especially those designed to be diluted with a carrier prior to application. These agents are typically used at a concentration of 0.1% to 15% by weight of the formulation. They can be anionic, cationic, nonionic, or polymeric in nature and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates, such as diethanolammonium lauryl sulfate; alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol-epoxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-epoxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium chloride, such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphates.

[0331] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, defoamers, opacifiers, compatibilizers, masking agents, neutralizers and buffers, corrosion inhibitors, dyes, flavor enhancers, spreading agents, penetration enhancers, micronutrients, softeners, lubricants, and fixatives.

[0332] Furthermore, other biocidal active ingredients or compositions may be combined with the compositions of the present invention and used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated or mixed together with the compositions of the present invention, for example, in a spray can. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, and / or plant growth regulators.

[0333] The pesticides referred to in this article by their common names are, for example, known from "The Pesticide Manual", 15th edition, British Crop Protection Council 2009.

[0334] Furthermore, the compositions of the present invention can also be administered in combination with one or more systemically acquired resistance inducers (“SAR” inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer aramid-benzene-S-methyl.

[0335] Compounds of formula (I) according to the invention are generally used in the form of agricultural chemical compositions and can be applied simultaneously or sequentially to the crop area or plant to be treated. For example, these additional compounds may be fertilizers or micronutrient donors or other formulations that affect plant growth. They may also be selective or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these formulations, and, if desired, with additional carriers, surfactants, or application-promoting adjuvants commonly used in the field of formulations.

[0336] The compounds of formula (I) according to the invention can be used in the form of (fungicide) compositions for controlling or protecting against plant pathogenic microorganisms, the compositions comprising at least one compound of formula (I) as an active ingredient or at least one preferred single compound as defined herein (in free form or in the form of an agrochemically available salt) and at least one of the above-described adjuvants.

[0337] Therefore, the present invention provides a composition comprising at least one compound of formula (I) according to the invention, an agriculturally acceptable carrier, and optionally an adjuvant, preferably a fungicidal composition. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I), the composition may also comprise at least one or more bioactive compounds, such as additional fungicidal active ingredients.

[0338] The compound of formula (I) according to the invention may be the sole active ingredient of the composition, or, where appropriate, may be mixed with one or more other active ingredients (such as pest control agents, fungicides, synergists, herbicides, or plant growth regulators). In some cases, the additional active ingredients may produce unexpected synergistic activity.

[0339] Other suitable active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, arsenic-containing fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzoylaniline fungicides, benzimidazole fungicides, benzothiazole fungicides, phytofungicides, bridged biphenyl fungicides, carbamate fungicides, phenyl carbamate fungicides, conazole fungicides, copper fungicides, diformimide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiopentane fungicides, furfural amide fungicides, furfuryl aniline fungicides, acylhydrazine fungicides, imidazole fungicides, mercury fungicides. Fungicides, morpholine fungicides, organophosphate fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, thiophene fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, acanthocarbamate fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazolidinyl fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides.

[0340] The following mixtures of compounds having formula (I) and active ingredients are preferred. The abbreviation "TX" refers to a compound selected from compounds having the formula (I), (IA), or (I-A1), or a compound selected from compounds listed in Tables C-1 to C-56 or Table P (hereinafter), and a compound selected from the group consisting of: (4E,10Z)-tetradec-4,10-dienyl acetate + TX; (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX; (E)-6-methylhept-2-en-4-ol + TX; (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX; (E)-tetrate-4-en-1-yl acetate + TX; (S)-bioallethrin + TX; (Z)-dodec-7-en-1-yl acetate + TX; (Z)-hexadec-11-en-1-yl acetate + TX; TX; (Z)-hexadec-11-enal + TX; (Z)-hexadec-13-en-11-yn-1-yl acetate + TX; (Z)-eicos-13-en-10-one + TX; (Z)-tetradec-7-en-1-al + TX; (Z)-tetradec-9-en-1-ol + TX; (Z)-tetradec-9-en-1-yl acetate + TX; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX; 1-(2-chlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)but-2-ol + TX; 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)prop-2-ol + TX; 1-H-hydroxy-1H-pyridine-2-thione + TX; 1-methylcyclopropene + TX; 1-naphthylacetamide + TX; 1-naphthylacetic acid + TX; 2,2-dichlorovinyl-2-ethylsulfinyl ethyl methyl phosphate + TX; 2,4-D + TX; 2,4-DB + TX; 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide + TX; 2-(1,3-dithiopentane-2-yl)phenyl dimethyl carbamate + TX; 2-(2-butoxyethoxy)ethyl piperate + TX; 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenyl methyl carbamate + TX; 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX; 2-(octylthio)-ethanol + TX; 2-bromo-2-bromomethylglutaronitrile + TX; 2-chlorovinyl diethyl phosphate + TX; 2-imidazolinone + TX; 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX;2-Cyanothioylethyl Laurate + TX; 3-(4-Chlorophenyl)-5-methylrhodanine + TX; 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindane-4-yl]pyrazole-4-carboxamide + TX; 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indane-4-yl)-1-methyl-pyrazole-4-carboxamide + TX; 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indane-4-yl)-1-methyl-pyrazole-4-carboxamide + TX; 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX; 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate + TX; 3-phenylphenol + TX; 4,5-Dichlorodithiol-3-one + TX; 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazin-3-carboxylonite + TX; 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazole-3-amine + TX; 4-(quinoxaloline-2-ylamino)benzenesulfonamide + TX; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX; 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX; 4-CPA + TX; 4-Methyl(prop-2-ynyl)amino-3,5-dimethylmethylcarbamate + TX; 4-Methylnon-5-ol and 4-methylnon-5-one + TX; 4-Phenylenol + TX; 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone + TX; 5-amino-1,3,4-thiadiazol-2-thiol + TX; 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine + TX; 5-hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro-1,2,4-triazine-3(2H)-one + TX; 5-methyl-6-thio-1,3,5-thiadiazine-3-ylacetic acid + TX; 8-hydroxyquinoline sulfate + TX; 11-Ethyl-10,12-dioxo-2,5,8-trithia-4,11-diazatricyclo[7.3.0.03,7]dodec-1(9),3,6-trien-6-carboxynitrile + TX; 14-Methyloctadec-1-ene + TX; [(9Z,11E)-tetradec-9,11-dienyl]acetate + TX; [(Z)-dodec-9-enyl]acetate + TX; abamectin + TX; acephate + TX; miticide + TX; acetamiprid + TX; aspartame + TX;Acetaminophen + TX; Aramacin + TX; Aramacin-S-methyl + TX; Flufenoxuron + TX; Cotton Brown Leaf Roller GV + TX; Agrobacterium radiata + TX; Cotton Bollworm + TX; Albendazole + TX; Aldicarb + TX; Propyrethroid + TX; Alpromethazine + TX; Allyl alcohol + TX; Dimethomorph + TX; α-Decidulin + TX; α-Polycarb + TX; Amblyoxadixyl + TX; Azoxystrobin + TX; Cypermethrin + TX; Sulfamethoxam + TX; Phosphamidon + TX; Methion + TX; Indoxam + TX; Ammonium phosphate + TX; Ammonium phosphate oxalate + TX; Amitraz + TX; Neonicotinic acid + TX; Celery Earworm NPV + TX; Pyrimidinol + TX; Dimethomorph + TX TX; Fluphenyladenine + TX; Anthraquinone + TX; Antoxin + TX; Short-spurred aphid wasp + TX; Cotton aphid parasitic wasp + TX; Aphid gall midge + TX; Ethyl chlorpyrifos + TX; Golden nystatin + TX; Alfalfa silver-striped moth NPV + TX; Abamectin B1a + TX; Azaconazole + TX; Azadirachtin A + TX; Pyrazosulfan + TX; Ethyl glutathione + TX; Methyl glutathione + TX; Thiram + TX; Azoxystrobin + TX; Bacillus spheroides (Neide) + TX; Bacillus thuringiensis + TX; Bacillus thuringiensis δ-endotoxin + TX; Bacillus thuringiensis subsp. sarsaparilla + TX; Baculovirus + TX; Pyrethroid + TX; Beauveria bassiana + TX; Benzoyl + TX; Benzoyl-M + TX; Benazepril + TX; Benzothiamethoxam + TX; Prothiocarbamate + TX; Benomyl + TX; Sulfuric acid + TX; Benzothiamethoxam + TX; Benzalkonium chloride + TX; Phytoprofen + TX; Benzothiamethoxam + TX; Benzopyr + TX; β-Cypermethrin + TX; β-Cypermethrin + TX; Benzothiazoxazin + TX; Bifenazate + TX; Bifenazate + TX; Bifenthrin + TX; Acaricide + TX; Bio-allethrin + TX; Bio-cypermethrin + TX; Bio-permethrin + TX; Bio-benzoxystrobin + TX; Diflubenzuron + TX; Bifenthrin + TX; Bifenazate + TX; Bifenazate + TX; Blastcin-S + TX; Borax + TX; Bordeaux mixture + TX; Cypermethrin + TX TX; Bromodiphenyl ether + TX; Bromocypermethrin + TX; Bromofluoromethyl + TX; Bromodifen + TX; Bromophos + TX; Bromophos + TX;Bromothion-ethyl + TX; Fenoxacillin + TX; Dimethoate + TX; Ethylpyrimethanil sulfonate + TX; Thiazide + TX; Buserelin + TX; Busulfan + TX; N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yneylylene + TX; Butyroxon + TX; Specimenthion + TX; Butanoxon + TX; Butyl ester + TX; DEET + TX; Butoxy(polypropylene glycol) + TX; Butanoxon sulfonate + TX; Butylamine + TX; Thiophanate + TX; Calciferol + TX; Calcium phosphate + TX; Calcium polysulfide + TX; Canbendazole + TX; Captan + TX; Captan + TX; Chlorfenapyr + TX; Carbaryl + TX; Carbendazim + TX TX; Carbendazim hydrochloride + TX; Carbofuran + TX; Thiophanate + TX; Carbofuran + TX; Carbofuran + TX; Cyproterenol + TX; Pyridaben + TX; Pyridaben hydrochloride + TX; Cephalexin + TX; Cefotaxime + TX; Ceftriaxone + TX; Ceftiofur + TX; Cestex + TX; Servadine + TX; Acaricide + TX; Chitosan + TX; Chlorpheniramine + TX; Chloralose + TX; Chlorantraniliprole + TX; Chlorfenapyr + TX; Acaricide + TX; Ethephon + TX; Phosphorus + TX; Brofenoxuron + TX; Chlorfenapyr + TX; Tetramethrin + TX; Clofenthion + TX; Difenoconazole + TX; Chlormethrin + TX; Chlormethrin + TX; Chlormequat + TX; Acaricide hydrochloride + TX TX; Chlorpyrifos + TX; Amitraz + TX; Diflubenzuron + TX; Dimethoate + TX; Chlorothalonil + TX; Chlorpyrifos + TX; Chlorpyrifos + TX; Chlorpyrifos-methyl + TX; Chlortetracycline + TX; Chlormethoate + TX; Ethiophanate + TX; Cholecalciferol + TX; Cyclofenac + TX; Common lacewing + TX; Cucurbitacin + TX; Cucurbitacin I + TX; Cucurbitacin II + TX; Cis-jasmone + TX; Cis-resmethrin + TX; Cismethrin + TX; Clenbuterol + TX; Glycyrrhizin + TX; Dichlorvos + TX; Benadryl + TX; Clostridium + TX; Thiamethoxam + TX; Chlorpyrifos (acetamide) + TX; Dodecadienol + TX; Copper acetate + TX; Copper hydroxide + TX; Copper naphthenate + TX; Copper octanoate + TX; Copper oleate + TX; Copper oxide + TX; Copper oxychloride + TX; Copper silicate + TX;Copper sulfate + TX; Copper carbonate (II) + TX; Chlorpyrifos + TX; Coumafene + TX; Rat parathion + TX; Rodenticide + TX; Coumethoxystrobin + TX; Phoxim + TX; Eugenol + TX; Cryolite + TX; Crassula monnieri + TX; Fly attractant + TX; Thiazol + TX; Cuprous oxide (I) + TX; Benzoate + TX; Folic acid + TX; Cyazofamid + TX; Cyprodinium + TX; Cyprodinium + TX; Cyprodinium + TX; Cyprodinium + TX; Cyfluthrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cymoxanil ... TX; Cypermethrin (cis-cypermethrin) + TX; Pyrimethanil + TX; Cyproconazole + TX; Azoxystrobin + TX; Azoxystrobin + TX; Cyromazine + TX; Cyromazine + TX; Cymoxanil + TX; D-methoxystrobin + TX; Siberian parasitic wasp + TX; DAEP + TX; Dazomet + TX; DCPM + TX; Imazalil + TX; Demethylcarbofuran + TX; Delmethrin + TX; Tebufenozide-O + TX; Tebufenozide-S + TX; Demeton-O + TX; Demeton-S + TX; Demeton-S-methyl + TX; Sulfonate + TX; Acaricide + TX; Chlorpyrifos + TX; Diazinon + TX; Dibutyl adipate + TX; Dibutyl phthalate + TX; Dibutyl succinate + TX; Isochlorpyrifos + TX; Dichlorophenoxyacetic acid + TX TX; Antibacterial agent + TX; Dichloronaphthoquinone + TX; 2,4-D propionic acid + TX; Dichlorvos + TX; Sclerotinia + TX; Cyazofamid + TX; Pyridaben + TX; Chlornitramine + TX; Trichlorfon + TX; Dioxac + TX; Phosphate + TX; Desniprochlor + TX; Dicyclopentadiene + TX; Ethiocarb + TX; DEET + TX; Dimethoate + TX; Difenoconazole + TX; Wild ginseng + TX; Thiamethoxam + TX; Flufenoxuron + TX; Diflubenzuron + TX; Flufenoxuron + TX; Pea leafminer wasp + TX; Dimethoate + TX; Tetrafluorometholone + TX; Dimethoate + TX; Sclerotinia + TX; Thiamethoxam + TX; Mefenoxam + TX; Dimethoate + TX; Dimethoate + TX; Permethrin + TX TX; Dimethyl disulfide + TX; Dimethyl phthalate + TX; Difenoconazole + TX; Azoxystrobin + TX;Diclofenac + TX; Tebuconazole + TX; High-efficiency Tebuconazole + TX; Difenoconazole + TX; Difenoconazole + TX; O-difen + TX; Diphenoxyphenanthrene + TX; Difenoconazole + TX; Benzyl + TX; Phosphate + TX; Diphenylamine + TX; Dipyridamole + TX; Nondecane + TX; Disulfiram + TX; Ethiophora + TX; Phosphate + TX; Dithiazoline + TX; Thiamethoxam + TX; Dithiocarbamate + TX; Dodecano-8-en-1-ylacetate + TX; Dodecylmorpholine + TX; Dodecyl + TX; Doxorubicin + TX; Phenoxypropyne + TX; Domipherex + TX; Dolactin + TX; Difenoconazole + TX; DSP + TX; Ectosteroids + TX; Kefensan + TX; Emafenac Benzoate + TX; EMPC + TX; Dextromethorphan + TX; Encarsia formosa + TX; Endothiocyanate + TX; Herbadox + TX; Phoxim + TX; Enoxacin + TX; Enrofloxacin + TX; Insect pathogenic bacteria + TX; Insect pathogenic fungi + TX; Insect pathogenic viruses + TX; EPBP + TX; Flutriafol + TX; Irinoctazine + TX; Aphids + TX; Cypermethrin + TX; Ethiconazole + TX; Thiamethoxam + TX; Ethiocarbamate + TX; Ethiophos + TX; Ethioprine + TX; Ethioprine + TX; Ethioprine + TX; Ethioprine + TX; Ethyl oxychloride + TX; Ethyl formate + TX; Ethylhexane + TX; Ethylpyridinium + TX; Ethyl oxychloride + TX; Ethyl oxychloride + TX; Ethyl oxychloride + TX; Ethyl oxychloride + TX; Chlorpyrifos + TX; TX; Ethylpyrimethanil + TX; Eugenol + TX; Eurax + TX; EXD + TX; Exo-Western Pine Bark Beetle Collective Pheromone + TX; Oxadiazon + TX; Valproic acid + TX; Farnesol and Nerolidol + TX; Fibentol + TX; Imidacloprid + TX; Enoxaflutole + TX; Benzophos + TX; Chlorpyrimethanil + TX; Quinalox + TX; Fenbendazole + TX; Cyproconazole + TX; Fenoxaflutole + TX; Quinoline + TX; Ethylcarb + TX; Pyrimethanil + TX; Mefenoxam + TX; Cyclocarb + TX; Fenitrothion + TX; Butyric acid + TX; Difenoconazole + TX; Benthiocarb + TX; Oxypyrimethanil + TX; Cyanamide + TX; Fenoxycarb + TX; Seed dressing + TX; fenpicoxamid + TX; pyrethroid + TX; cypermethrin + TX; benzyl benzoate + TX; butyl morpholine + TX;Amifenozide + TX; Azoxystrobin + TX; Fosetyl-aluminum + TX; Fenthion + TX; Ethyl Fenthion + TX; Triphenyltin + TX; Triphenyltin Acetate + TX; Triphenyltin Chloride + TX; Triphenyltin Hydroxide + TX; Cypermethrin + TX; Ferrous Sulfate + TX; Azoxystrobin + TX; Ferric Phosphate + TX; Fipronil + TX; Flufenoxuron + TX; Flufenoxuron + TX; Pyridaben + TX; Azoxystrobin + TX; Flufenoxuron + TX; Pyridaben + TX; Flufenoxuron + TX; Pyridaben + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Cypermethrin + TX; Fludioxonil + TX; Biflufenoxuron + TX; Pyrimethanil + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX TX; Trifluthrin + TX; Fluopyram + TX; Flubendiamide + TX; Flusulfanilamide + TX; Flumorph + TX; Fluopyram + TX; Fluopyram + TX; Fluopyram + TX; Fluopyram + TX; Fluoxetine + TX; Fluoxetine + TX; Fluopyram ... TX; Phosphate + TX; Southern pine bark beetle collection pheromone + TX; Wheat bran + TX; Furazolidone + TX; Furazolidone + TX; Furazolidone + TX; Pyrethrum + TX; Furfural + TX; Gibberellin + TX; Glyphosate + TX; Lure-killing agent mixture I + TX; Lure-killing agent mixture II + TX; Lure-killing agent mixture III + TX; Lure-killing agent mixture IV + TX; Biguanidin triacetate + TX; Benzyl ether + TX; Chlorfenapyr + TX; Hexamethonium + TX; Hepten + TX; *Heterotrophic cephalopoda* and *Heterotrophic cephalopoda* + TX; Hexaconazole + TX; Hexadecyl cyclopropanecarboxylate + TX; Flufenoxuron + TX; Hexyl attractant + TX; Hexylamide + TX; Thiamethoxam + TX; Spotted ladybug + TX; Cyclotridium (racemic-(1S,2S)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cycloheptanol) + TX; Fluoridone + TX;Quicklime (calcium hydroxide) + TX; Hymexazol + TX; Quinoline + TX; Icaridin + TX; Hypericin + TX; Imazalil + TX; Imazalil sulfate + TX; Imidazole + TX; Imidacloprid + TX; Biguanidine octylamine + TX; Indoxacarb + TX; Indopyramide + TX; Iodocarb + TX; Succinimidazole + TX; Ifentriconazole + TX; Iprodione + TX; Isopyram (IBP) + TX; Iprodione + TX; Valcarb + TX; Tebufenol + TX; Tebufenol + TX; IPSP + TX; Isamidophos + TX; Chlorpyrifos + TX; Methionine + TX; Iprodione + TX; Iprodione + TX; Iprodione + TX TX; Transplanting agent + TX; Isoprocarb + TX; Isoprothiolane + TX; Pyraclostrobin + TX; Isoprophos + TX; Isothiazine + TX; Isoxazol + TX; Ivermectin + TX; Scarab beetle pheromone + TX; Jasmine I + TX; Jasmine II + TX; Juvenile hormone I + TX; Juvenile hormone II + TX; Juvenile hormone III + TX; Thiamethoxam + TX; Kanamycin + TX; Kasugamycin + TX; Kasugamycin hydrochloride hydrate + TX; Kinetin + TX; Acetaminophen + TX; Azoxystrobin + TX; Bacillus thuringiensis subsp. Kustag + TX; λ-Cypermethrin + TX; Citrus citrus scale parasitic wasp + TX; Parafenoxam + TX; Levamisole + TX; Trimethyldioxane + TX; Acetaminophen + TX; Pesticide for the white armyworm + TX; Lufenuron + TX; Chlorfenapyr + TX; Phosphate + TX; propylphenyl methyl carbamate + TX; Mirid bug + TX; Magnesium phosphide + TX; Malathion + TX; Maleic hydrazine + TX; Propiconazole + TX; Cabbage armyworm NPV + TX; Mancozeb + TX; Mancozeb + TX; Tobramycin + TX; Dimethomorph + TX; Mancozeb + TX; Azoxystrobin + TX; Mebendazole + TX; Phosphate + TX; Tetramethrin + TX; Acetate + TX; Chlorfluazuron + TX; Megacodone + TX; Meloxiconazole + TX; Apimethanil + TX; Azoxystrobin + TX; Cypermethrin + TX; Dithiamethoxam + TX; Mepiquat chloride + TX; Corrosiver + TX; Acaricide + TX TX; sulfoxide + TX; cyfluthrin + TX; metalaxyl + TX; metalaxyl-M + TX; metaldehyde + TX; methylphenidate + TX;Micromethrin-potassium + TX; Micromethrin-sodium + TX; Yellow-stalked flea beetle + TX; Metarhizium anisopliae var. ... TX; Mefenoxam + TX; Zicrolimus + TX; MGK 264 + TX; Milbemycin + TX; Milbexime + TX; Monoclonal + TX; Molentaxel Tartrate + TX; Sterilidine + TX; Moxifloxacin + TX; Insecticidal + TX; Cyproconazole + TX; Mefenoxam + TX; Varicella spp. Combination + TX; N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX; N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide + TX; Sodium Mancozeb + TX; Dibromophos + TX; NC-170 + TX; Namethin + TX; New Pine Sawfly NPV and Red-headed New Pine Sawfly NPV + TX; Nitrosamide-ethanolamine + TX; Nicotine + TX; Nicotine sulfate + TX; Nicotinic acid + TX; Acetaminophen + TX; Niethoxysulfuron + TX; Chlorpyrifos + TX; Cypermethrin + TX; Phthalosporin + TX; Sodium thiosulfate + TX; Nononic acid + TX; Fluorouracil + TX; Polyfluorourea + TX; Fluphenazine + TX; O,O,O',O'-Tetrapropyl dithiophosphate + TX; Octadec-2,13-dien-1-ylacetate + TX; Octadec-2,13-dien-1-ylacetate + TX; Octadec-2,13-dien-1-ylacetate + TX; Octathione + TX; Furazolidone + TX; Oleic acid + TX; Omethoate + TX; Heconazole + TX; Small-flowered bug species + TX; Oxime azoxystrobin + TX; Osthol + TX; Filacon + TX; Oxystrobin + TX TX; oxaloacetate + TX; oxadiazon + TX; octyl acetonide + TX; cyclophosphamide + TX; fluoxetine + pyrrophenone + TX; oxifenezazole + TX; oxendazole + TX;Quinoline copper + TX; Oxadiazon + TX; Oxazol + TX; Oxytetracycline + TX; Phosphine sulfoxide + TX; Isofenphos + TX; Phosphine sulfone + TX; Oxytetracycline + TX; Oxytetracycline dihydrate + TX; Paclobutrazol + TX; Paecilomyces roximate + TX; Paraoxon + TX; Parathion + TX; Methyl parathion + TX; Pabendazole + TX; Isoprothiolane + TX; Tebuconazole + TX; Pendimethoate + TX; Pendimethoate + TX; Pfenoxam + TX; Fluopyram + TX; Pyraclostrobin + TX; Permethrin + TX; Petroleum + TX; pH 60-38 + TX; Cyazofamid + TX; Indomethacin + TX; Phosphate + TX; Rat parathion + TX; Phosphate + TX; Thiophanate + TX; Glyphosate + TX; Isophosphamidon + TX; Chlorpyrifos + TX TX; Phosphamidon + TX; Fipronil + TX; Phosphonic acid + TX; Phosphate + TX; Phoxim + TX; Methyl phoxim + TX; Phenylphthalide + TX; Phytoseione gardica cochinchinensis + TX; Tetraazolidinium + TX; Azoxystrobin + TX; Pimobendan + TX; Warfarin + TX; Piperaldehyde + TX; Piperyl Butyl ether + TX; Synergistic aldehyde + TX; Methamidophos + TX; Piperazine + TX; Methylpyrimidin + TX; Polycarbamate + TX; Naphthyl bacillus + TX; Polyoxin B + TX; Polyoxin D + TX; Potassium ethyl xanthate + TX; Potassium hydroxyquinoline sulfate + TX; Praziquantel + TX; Precipitin I + TX; Precipitin II + TX; Precipitin III + TX; Aminopyrimidin + TX; Thiamethoxam + TX; Prochloraz + TX; Iprodione + TX; Profenofos + TX; Profenofos + TX; Cyclophos + TX; Calcium Cyclophos + TX; Iprodione + TX; Mancozeb + TX; Propamid + TX; Cymoxanil + TX; Propanil + TX; Acetaminophen + TX; Pyrazophos + TX; Propiconazole + TX; Propineb + ​​TX; Propine + TX; Propyrazophos ... TX; Bifenazate + TX; Phoxim + TX; Pyrazinone + TX; Pyrethroid + TX; Pyrethroid I + TX; Pyrethroid II + TX;Pyrethroids (natural products) + TX; Pyrethroids (natural products) + TX; Pyraclostrobin + TX; Pyridaben + TX; Flufenoxuron + TX; Acetaminophen + TX; Pyridaben + TX; Pyridaben + TX; Pyridaben + TX; Pyridaben + TX; Fipronil + TX; Pyrimethanil + TX; Pyridaben ... TX; Ribavirin + TX; Rotenone + TX; Randine (Randine) + TX; Veratrum saba + TX; Benzyl + TX; Onion glycoside + TX; Cymoxanil + TX; Fluoxetine + TX; Silachlor + TX; Synergistic powder + TX; Sesamol + TX; Insect attractant + TX; Flusilazole + TX; Silthiamethoxam + TX; Silomethasone + TX; Silomethasone + TX; Sodium tetrathiocarbonate + TX; Threphalosporin + TX; Sodium dimethoate + TX; Spinosad + TX; Spirodiclofen + TX; Spirodiclofen + TX; Spirodiclofen + TX; Spirodiclofen + TX; Spirodiclofen + TX; Trichodina + TX; Strychnos + TX; Strychnos + TX; Grylloides + TX; Strychnos + TX; Strychnos + TX; Strychnos + TX TX; *Nematodes skeletalus* + TX; *Nematodes skeletalus* species + TX; Streptomycin + TX; Streptomycin sesquisulfate + TX; Fungicide + TX; Sulfodioxonium + TX; Sulfur + TX; Thiophanate + TX; Tar + TX; T-flumethrin + TX; TCMTB + TX; TDE + TX; Tebuconazole + TX; Tebufenozide + TX; Pyridaben + TX; Isobutyloxyquinoline + TX; Butylpyrimidine + TX; Tetrachloronitrobenzene + TX; Flufenoxuron + TX; Heptafluthrin + TX; Dithion + TX; Cypermethrin + TX; Terbuphos + TX; Terbuphos + TX; Insecticidal + TX; Flufenoxuron + TX; Tetradecane-11-en-1-ylacetate + TX; Tetrachlorpyrifos + TX; Pyrethroid + TX; Tetrafluoroethylene + TX; Acaricide + TX; Thiabendazole + TX; Thiamethoxam + TX; Copper thiamethoxam + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thiamethoxam + TX;Thiamethoxam + TX; Thiabenzolam + TX; Thifluzamide + TX; Carbendazim + TX; Cypermethrin + TX; Cypermethrin oxalate + TX; Thiamethoxam + TX; Dimethoate + TX; Methionine + TX; Thiophanate + TX; Thiamethoxam + TX; Acaricide + TX; Carbendazim + TX; Carbendazim-disodium + TX; Thiamethoxam + TX; Thiamethoxam + TX; Tiamulin + TX; Tioxymid + TX; Methyl thiophanate + TX; Azoxystrobin + TX; Trifluralin + TX; Tetrabromopropylate + TX; Permethrin + TX; Tratamide + TX; Triadimefon + TX; Triadimefon + TX; Benzoate + TX; Azoxystrobin + TX; Triazophos + TX; Imidazin + TX TX; Defoliant + TX; Trichlorfon + TX; Heterophosphorus-3 + TX; Phosphorus + TX; Trichogramma species + TX; Trichlorophenazole + TX; Chlorpyrifos + TX; Tricyclazole + TX; Tridemorph + TX; Snailicide + TX; Azoxystrobin + TX; Fluopyram + TX; Cyclofenac + TX; Azoxystrobin + TX; Mediterranean fruit fly attractant + TX; Mediterranean fruit fly attractant A + TX; Mediterranean fruit fly attractant B1 + TX; Mediterranean fruit fly attractant B2 + TX; Mediterranean fruit fly attractant C + TX; Mixed carbendazim + TX; Trichloroisocyanuric acid + TX; Anti-rot ester + TX; Anti-rot ester-ethyl + TX; Entamoxetine + TX; Mefenoxam + TX; Chuangke + TX; Torazom + TX; Western blind mite + TX; Uniconazole + TX; Urethroid + TX; Effectivemycin + TX; Valhalax + TX; Amifenoxam + TX; Mefenoxam + TX; Veratrine + TX; Veratrine + TX; Synergistic alkyne + TX; Verticillium spp. + TX; Ethylene sclerotinib + TX; XMC + TX; Xylenol + TX; Zeazoline + TX; ζ-Cypermethrin + TX; Kasugamycin + TX; Zinc naphthenate + TX; Thiazole zinc + TX; Zineb + ​​TX; Zinc thiocyanate + TX; Zinc thiram + TX; Azoxystrobin + TX; Benzoylamidol + TX; 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by the method described in WO 2019 / 093522) + TX;(2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO 2019 / 093522) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; azoxystrobin (this compound can be prepared by the method described in WO 2014 / 006945) + TX; thiamethoxam (this compound can be prepared by the method described in WO 2011 / 138281) + TX; 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound can be prepared by the method described in WO 2017 / 016915) + TX; 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2021 / 249800) + TX; 1-[2-chloro-4-(difluoromethoxy)phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2021 / 249800) + TX; 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound can be prepared by the method described in WO 2017 / 016915) + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylthiocarboxamide (this compound can be prepared by the method described in WO 2015 / 185485) + TX; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2017 / 178245) + TX; fluopyram + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (this compound can be prepared by WO 2017 / 01691 ... (Prepared by the method described in WO 2015 / 185485) + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (This compound can be prepared by the method described in WO 2018 / 153707) + TX;(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2013 / 092224) + TX; (2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]methyl acetate (this compound can be prepared by the method described in WO2022 / 033906) + TX; (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO 2022 / 033906) + TX; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound can be prepared by the method described in WO 2021 / 249928) + TX; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (this compound can be prepared by the method described in WO 2021 / 249928) + TX; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxynitrile (this compound can be prepared by WO 2021 / 249928) + TX; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxynitrile (this compound can be prepared by WO 2021 / 249928) + TX; (Prepared by the method described in WO 2016 / 156290) +TX; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazolium-4-carboxylonitrile (This compound can be prepared by the method described in WO 2016 / 156290) +TX; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) +TX; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX;5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazole-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[(4-bromo-2-methyl-phenyl)methyl]-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the method described in WO 2021 / 255070) + TX; 3-[3-(3-cyclopropyl-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the method described in WO 2021 / 255070) + TX; N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazol-4-carboxamide (this compound can be prepared by the method described in WO 2022 / 133114) + TX; 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the method described in WO 2022 / 133114) + TX; 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX;1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX; N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate methyl ester (this compound can be prepared by the methods described in WO 2020 / 097012) + TX; N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-3-yl]-2-methyl-phenyl]methyl]carbamate methyl ester (this compound can be prepared by the methods described in WO 2020 / 097012) + TX; N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX; 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO 2019 / 093522) + TX; 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline + TX; 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolinyl)isoquinoline + TX; 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared by the method described in WO 2020 / 256113) + TX; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methyl-propionamide (this compound can be prepared by the method described in WO 2020 / 256113) + TX; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 256113) +TX; 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indane-4-yl)pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; 2-(difluoromethyl)-N-(1,1,3-trimethylindane-4-yl)pyridine-3-carboxamide + TX;(5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) + TX; (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) +TX; 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780, WO 2021 / 255070) +TX; (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be prepared by the methods described in JP 2023078251) +TX; 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide +TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures thereof + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1). 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures thereof + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109509 A1); 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX;Or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO2019105933 A1, WO 2020109509 A1); 2-[(2,6-difluoro-4-pyridinyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO2020109511 A1, WO 2021244952 Prepared by the method described in A1); 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the method described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (this compound can be prepared by the method described in WO 2017 / 055473) + TX; (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387) + TX; (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387) + TX; N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX; N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX; 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1);2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017 / 055473).

[0341] References in parentheses following the active ingredient, such as [3878-19-1], refer to Chemical Abstracts Registry Numbers. The mixtures described above are known. In cases where the active ingredient is included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13th Edition; Editor: CDS TomLin; The British Crop Protection Council], they are described therein by the entry number given in parentheses above for the specific compound; for example, the compound "Abamedin" is described by entry number (1). In cases where "[CCN]" is added above to a specific compound, the compound is included in "Compendium of Pesticide Common Names," which is available on the Internet [A. Wood; Compendium of Pesticide Common Names [Copyright © 1995-2004]; for example, the compound “acetoprole” is described at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0342] Most of the aforementioned active ingredients are referred to above by their so-called “common name,” with the corresponding “ISO common name” or another “common name” used in individual cases. If the name is not a “common name,” the type of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “common name,” “compound name,” or “development code” is used, or if neither of those names nor a “common name” is used, an “alias” is used. “CAS Registry Number” refers to the Chemical Abstracts Registry Number.

[0343] The active ingredient mixtures of compounds selected from those having formula (I), (IA), or (I-A1), or those listed in Tables C-1 to C-56 or Table P (hereinafter), are preferably mixed in ratios of 100:1 to 1:100, especially 50:1 to 1:50, more especially 20:1 to 1:20, even more especially 10:1 to 1:10, and still more especially 5:1 to 1:5. These mixing ratios are by weight.

[0344] The mixture described above can be used in methods for controlling pests, excluding methods of applying a composition containing the mixture described above to pests or their environment, methods of treating humans or animals by surgery or therapy, and diagnostic methods performed on humans or animals.

[0345] A mixture comprising a compound selected from compounds having formula (I), (IA), or (I-A1), or compounds listed in Tables C-1 to C-56 or Table P (hereinafter), and one or more active ingredients as described above, may be applied, for example, as a single "ready-to-use with water" formulation, as a combined spray mixture such as a "bucket mix" consisting of individual formulations of a single active ingredient component, and when applied sequentially, i.e., one after another over a reasonably short period of time (e.g., hours or days). The order in which the compound selected from compounds having formula (I), (IA), or (I-A1), or compounds listed in Tables C-1 to C-56 or Table P (hereinafter), and one or more active ingredients as described above are applied is not important for carrying out the invention.

[0346] The compositions according to the invention may also contain additional solid or liquid adjuvants, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers (e.g., silicone oil), preservatives, viscosity modifiers, binders and / or thickeners, fertilizers, or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides, or herbicides.

[0347] The compositions according to the invention are prepared in a manner known per se, in the absence of adjuvants, for example by grinding, sieving, and / or compressing solid active ingredients; and in the presence of at least one adjuvant, for example by tightly mixing the active ingredient with one or more adjuvants and / or grinding the active ingredient together with one or more adjuvants. These methods for preparing the compositions and the use of the compound (I) for preparing these compositions are also the subject of this invention.

[0348] Another aspect of the invention relates to the use of a compound of formula (I) or a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, or a mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein with other fungicides or insecticides as described above, for the control or prevention of infection of plants (e.g., useful plants, such as crop plants), their reproductive material (e.g., seeds), harvested crops (e.g., harvested food crops), or inanimate materials by insects or by plant pathogenic microorganisms (preferably fungal organisms).

[0349] Another aspect of the invention relates to a method for controlling or preventing the infection of plants (e.g., useful plants, such as crop plants), their propagation material (e.g., seeds), harvested crops (e.g., harvested food crops), or inanimate materials by plant pathogenic microorganisms or putrefactive microorganisms or organisms potentially harmful to humans (especially fungal organisms), the method comprising applying as an active ingredient a compound having formula (I) according to the invention or a preferred individual compound as defined herein to these plants, parts of these plants or their sites, their propagation material, or any part of these inanimate materials.

[0350] Control or prevention means reducing the infestation by insects or plant pathogens or putrefactive microorganisms or potentially harmful organisms (especially fungal organisms) to a level that has been proven to be improved.

[0351] A preferred method for controlling or preventing crop infection by plant pathogenic microorganisms (especially fungal organisms) or insects is foliar application, which includes applying a compound of formula (I) according to the invention, or an agricultural chemical composition containing at least one compound of formula (I). The frequency and ratio of application will depend on the risk of infection by the corresponding pathogen or insect. However, the compound of formula (I) according to the invention can also penetrate the plant through the soil via roots (systemic absorption) by soaking the plant in a liquid formulation or by applying the compound in solid form, such as in granules, to the soil (soil application). In rice crops, such granules can be applied to irrigated paddy fields. The compound of formula (I) can also be applied to seeds (coating) by soaking the seeds or tubers in a liquid formulation of a fungicide or by coating them with a solid formulation.

[0352] Formulations (e.g., compositions containing compounds of formula (I) according to the invention, and (if desired) solid or liquid adjuvants or monomers for encapsulating compounds of formula (I)) can be prepared in a known manner, typically by closely mixing and / or grinding the compound with an adjuvant (e.g., a solvent, a solid carrier, and optionally a surfactant compound).

[0353] Favorable application rates are typically from 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably from 10 g to 1 kg ai / ha, and most preferably from 20 g to 600 g ai / ha. When used as a seed soaking agent, a suitable dosage is 10 mg to 1 g of active substance per kg of seeds.

[0354] As used herein, the term "g ai / ha" refers to the application ratio given in grams [g] of active ingredient [ai] per unit surface area [ha]. The unit hectare (symbol ha) is equal to a hectare with a side length of 100 m (1 hm²). 2 The hectare is a metric unit of area, representing a square area of ​​10,000 square meters or 10,000 square meters. The hectare is a commonly used unit of area in the metric system.

[0355] When the combination of the present invention is used to treat seeds, an application rate of 0.001 to 50 g of the compound having formula (I) per kg of seeds, preferably 0.01 to 10 g per kg of seeds, is generally sufficient.

[0356] Appropriately, compositions comprising compounds having formula (I) according to the invention may be applied preventively (meaning before the development of the disease) or therapeutically (meaning after the development of the disease).

[0357] The compositions of the present invention can be used in any conventional form, such as in the form of double-packaged powders for dry seed treatment (DS), emulsions for seed treatment (ES), flowable concentrates for seed treatment (FS), solutions for seed treatment (LS), water-dispersible powders for seed treatment (WS), capsule suspensions for seed treatment (CF), gels for seed treatment (GF), emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), dispersible oil suspensions (OD), oil suspensions (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulations in combination with agriculturally acceptable adjuvants.

[0358] Such compositions can be produced in conventional ways, for example, by mixing the active ingredient with appropriate formulation inert agents (diluents, solvents, fillers, and optionally other formulation ingredients such as surfactants, biocides, antifreeze agents, adhesives, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations designed for long-term sustained efficacy can also be used. In particular, formulations intended for application in spray form (such as aqueous dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules) may contain surfactants (such as wetting agents and dispersants) and other compounds that provide auxiliary effects, such as condensation products of formaldehyde with naphthalene sulfonates, alkyl aryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0359] The combination and diluent of the present invention are used to apply the seed dressing formulation to seeds in a manner known per se, in a suitable seed dressing formulation form (e.g., an aqueous suspension or dry powder form with good adhesion to seeds). Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in an encapsulated form, such as as a sustained-release capsule or microcapsule.

[0360] Typically, these formulations contain 0.01% to 90% by weight of an active agent, 0% to 20% of an agriculturally acceptable surfactant, and 10% to 99.99% of a solid or liquid formulation inert agent, as well as one or more adjuvants. The active agent is optionally composed of at least a compound of formula (I) according to the invention, together with other active agents (particularly microbicides or preservatives, etc.). Concentrated forms of the composition typically contain between about 2% and 80% by weight, preferably between about 5% and 70% by weight of the active agent. The formulation may be administered in an application form containing, for example, 0.01% to 20% by weight, preferably 0.01% to 5% by weight of the active agent. However, commercial products are preferably formulated as concentrates, and end users typically use diluted formulations.

[0361] However, it is preferable to formulate commercial products as concentrates, and end users will typically use diluted formulations.

[0362] Application rates vary widely and depend on soil properties, application method, crop, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. Generally, compounds can be applied at rates of 1 to 2000 l / ha, especially 10 to 1000 l / ha.

[0363] Preferred formulations may have the following composition (by weight%):

[0364] Emulsifiable concentrate :

[0365] Active ingredient: 1% to 95%, preferably 60% to 90%

[0366] Surfactant: 1% to 30%, preferably 5% to 20%

[0367] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0368] Dust powder :

[0369] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0370] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%.

[0371] Suspension concentrate:

[0372] Active ingredient: 5% to 75%, preferably 10% to 50%

[0373] Water: 94% to 24%, preferably 88% to 30%

[0374] Surfactant: 1% to 40%, preferably 2% to 30%

[0375] wettable powder :

[0376] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0377] Surfactant: 0.5% to 20%, preferably 1% to 15%

[0378] Solid carrier: 5% to 95%, preferably 15% to 90%

[0379] Granules:

[0380] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0381] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0382] The disclosures in this application make it possible to obtain every combination of the embodiments disclosed herein.

[0383] The compounds according to Tables C-1 to C-56 below can be prepared according to the methods described above. The following examples are intended to illustrate the invention and show preferred compounds having formula (I). In any of Tables C-1 to C-56 below, the presence of one or more possible asymmetric carbon atoms in the compounds having formula (I) according to the invention means that these compounds can exist in chiral isomer form (i.e., enantiomer or diastereomer).

[0384] Table A This table discloses the 20 substituent definitions G of formula (I).

[0385] (I)

[0386] Where G has the following defined formula :

[0387]

[0388] Table B This table discloses the 14 substituent definitions Q of formula (I).

[0389] (I)

[0390]

[0391] Tables C-1 to C-56 disclose specific compounds of the present invention having formula (I), wherein the Q and G substituents are as defined in Tables A and B.

[0392] Table C-1: This table provides 20 compounds of formula (I) from C-1.01 to C-1.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 and R 6 H is H, Q is Q-1 as defined in Table B, and G is as defined in Table A. For example, compound C-1.01 has the following structure:

[0393] Compound C-1.01

[0394] Table C-2: This table provides 20 compounds of formula (I) from C-2.01 to C-2.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 and R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0395] For example, compound C-2.04 has the following structure:

[0396] Compound C-2.04

[0397] Table C-3: This table provides 20 compounds of formula (I) from C-3.01 to C-3.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0398] Table C-4: This table provides 20 compounds of formula (I) from C-4.01 to C-4.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0399] Table C-5:This table provides 20 compounds of formula (I) from C-5.01 to C-5.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0400] Table C-6: This table provides 20 compounds of formula (I) from C-6.01 to C-6.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-6 as defined in Table B, and G is as defined in Table A.

[0401] Table C-7: This table provides 20 compounds of formula (I) from C-7.01 to C-7.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-7 as defined in Table B, and G is as defined in Table A.

[0402] Table C-8: This table provides 20 compounds of formula (I) from C-8.01 to C-8.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-8 as defined in Table B, and G is as defined in Table A.

[0403] Table C-9: This table provides 20 compounds of formula (I) from C-9.01 to C-9.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-9 as defined in Table B, and G is as defined in Table A. For example, compound C-9.02 has the following structure:

[0404] Compound C-9.02

[0405] Table C-10: This table provides 20 compounds of formula (I) from C-10.01 to C-10.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-10 as defined in Table B, and G is as defined in Table A.

[0406] Table C-11: This table provides 20 compounds of formula (I) from C-11.01 to C-11.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-11 as defined in Table B, and G is as defined in Table A.

[0407] Table C-12: This table provides 20 compounds of formula (I) from C-12.01 to C-12.20, wherein R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-12 as defined in Table B, and G is as defined in Table A.

[0408] Table C-13: This table provides 20 compounds of formula (I) from C-13.01 to C-13.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-13 as defined in Table B, and G is as defined in Table A.

[0409] Table C-14: This table provides 20 compounds of formula (I) from C-14.01 to C-14.20, where R 2 It is OCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-14 as defined in Table B, and G is as defined in Table A.

[0410] Table C-15:This table provides 20 compounds of formula (I) from C-15.01 to C-15.20, wherein R 2 It is OCH3, R 3 R 4 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A. For example, compound C-15.12 has the following structure:

[0411] Compound C-15.12

[0412] Table C-16: This table provides 20 compounds of formula (I) from C-16.01 to C-16.20, where R 2 It is OCH3, R 3 R 4 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0413] Table C-17: This table provides 20 compounds of formula (I) from C-17.01 to C-17.20, where R 5 R 6 It is CH3, R 2 It is OCH3, R 3 and R 4 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A. For example, compound C-17.04 has the following structure:

[0414] Compound C-17.04

[0415] Table C-18: This table provides 20 compounds of formula (I) from C-18.01 to C-18.20, where R 5 R 6 It is CH3, R 2 It is OCH3, R 3 and R 4 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0416] Table C-19: This table provides 20 compounds of formula (I) from C-19.01 to C-19.20, where R 3 It is H, R 4 R 5 R 6 It is CH3, R2 It is OCH3, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0417] Table C-20: This table provides 20 compounds of formula (I) from C-20.01 to C-20.20, where R 3 It is H, R 4 R 5 R 6 It is CH3, R 2 It is OCH3, Q is Q-5 as defined in Table B, and G is as defined in Table A. For example, compound C-20.18 has the following structure:

[0418] Compound C-20.18

[0419] Table C-21: This table provides 20 compounds of formula (I) from C-21.01 to C-21.20, where R 2 It is SCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0420] Table C-22: This table provides 20 compounds of formula (I) from C-22.01 to C-22.20, where R 2 It is SCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0421] Table C-23: This table provides 20 compounds of formula (I) from C-23.01 to C-23.20, where R 2 It is SCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0422] Table C-24: This table provides 20 compounds of formula (I) from C-24.01 to C-24.20, where R 2 It is SCH3, R 4 It is CH3, R 3R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0423] Table C-25: This table provides 20 compounds of formula (I) from C-25.01 to C-25.20, where R 2 It is SO2CH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0424] Table C-26: This table provides 20 compounds of formula (I) from C-26.01 to C-26.20, where R 2 It is SO2CH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0425] Table C-27: This table provides 20 compounds of formula (I) from C-27.01 to C-27.20, where R 2 It is SO2CH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0426] Table C-28: This table provides 20 compounds of formula (I) from C-28.01 to C-28.20, where R 2 It is SO2CH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0427] Table C-29: This table provides 20 compounds of formula (I) from C-29.01 to C-29.20, where R 2 It is NHCH3, R 4 It is CH3, R 3 R 5 R 6H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0428] Table C-30: This table provides 20 compounds of formula (I) from C-30.01 to C-30.20, where R 2 It is NHCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A. For example, compound C-30.14 has the following structure:

[0429] Compound C-30.14

[0430] Table C-31: This table provides 20 compounds of formula (I) from C-31.01 to C-31.20, where R 2 It is NHCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0431] Table C-32: This table provides 20 compounds of formula (I) from C-32.01 to C-32.20, where R 2 It is NHCH3, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0432] Table C-33: This table provides 20 compounds of formula (I) from C-33.01 to C-33.20, where R 2 It is N(CH3)2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0433] Table C-34: This table provides 20 compounds of formula (I) from C-34.01 to C-34.20, where R 2 It is N(CH3)2, R 4 It is CH3, R 3 R5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0434] Table C-35: This table provides 20 compounds of formula (I) from C-35.01 to C-35.20, where R 2 It is N(CH3)2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0435] Table C-36: This table provides 20 compounds of formula (I) from C-36.01 to C-36.20, where R 2 It is N(CH3)2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0436] Table C-37: This table provides 20 compounds of formula (I) from C-37.01 to C-37.20, where R 2 It is OH, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0437] Table C-38: This table provides 20 compounds of formula (I) from C-38.01 to C-38.20, where R 2 It is OH, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0438] Table C-39: This table provides 20 compounds of formula (I) from C-39.01 to C-39.20, where R 2 It is OH, R 4 It is CH3, R 3 R 5 R 6H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0439] Table C-40: This table provides 20 compounds of formula (I) from C-40.01 to C-40.20, wherein R 2 It is OH, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0440] Table C-41: This table provides 20 compounds of formula (I) from C-41.01 to C-41.20, where R 2 It is NH2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0441] Table C-42: This table provides 20 compounds of formula (I) from C-42.01 to C-42.20, where R 2 It is NH2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0442] Table C-43: This table provides 20 compounds of formula (I) from C-43.01 to C-43.20, where R 2 It is NH2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0443] Table C-44: This table provides 20 compounds of formula (I) from C-44.01 to C-44.20, where R 2 It is NH2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0444] Table C-45: This table provides 20 compounds of formula (I) from C-45.01 to C-45.20, wherein R 2 It is CN, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0445] Table C-46: This table provides 20 compounds of formula (I) from C-46.01 to C-46.20, where R 2 It is CN, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0446] Table C-47: This table provides 20 compounds of formula (I) from C-47.01 to C-47.20, where R 2 It is CN, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0447] Table C-48: This table provides 20 compounds of formula (I) from C-48.01 to C-48.20, where R 2 It is CN, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0448] Table C-49: This table provides 20 compounds of formula (I) from C-49.01 to C-49.20, where R 2 It is OCH2CHF2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0449] Table C-50: This table provides 20 compounds of formula (I) from C-50.01 to C-50.20, wherein R2 It is OCH2CHF2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-3 as defined in Table B, and G is as defined in Table A.

[0450] Table C-51: This table provides 20 compounds of formula (I) from C-51.01 to C-51.20, wherein R 2 It is OCH2CHF2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-4 as defined in Table B, and G is as defined in Table A.

[0451] Table C-52: This table provides 20 compounds of formula (I) from C-52.01 to C-52.20, wherein R 2 It is OCH2CHF2, R 4 It is CH3, R 3 R 5 R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A. For example, compound C-52.01 has the following structure:

[0452] Compound C-52.01

[0453] Table C-53: This table provides 20 compounds of formula (I) from C-53.01 to C-53.20, where R 2 It is OCH3, R 3 and R 4 It is CH3, R 5 and R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0454] Table C-54: This table provides 20 compounds of formula (I) from C-54.01 to C-54.20, where R 2 It is OCH3, R 3 and R 4 It is CH3, R 5 and R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A. For example, compound C-54.01 has the following structure:

[0455] Compound C-54.01

[0456] Table C-55: This table provides 20 compounds of formula (I) from C-55.01 to C-55.20, where R 2 It is OCH3, R 3 It is CH3, R 4 R 5 and R 6 H is H, Q is Q-2 as defined in Table B, and G is as defined in Table A.

[0457] Table C-56: This table provides 20 compounds of formula (I) from C-56.01 to C-56.20, where R 2 It is OCH3, R 3 It is CH3, R 4 R 5 and R 6 H is H, Q is Q-5 as defined in Table B, and G is as defined in Table A.

[0458] Example

[0459] The following examples are used to illustrate the invention and are not intended to limit the invention in any way.

[0460] The compounds of the present invention differ from known compounds in that they have greater efficacy at lower application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples, with lower application rates (if necessary), such as 60 ppm, 20 ppm, or 2 ppm.

[0461] Compounds having formula (I) can have many benefits, including, in particular, favorable levels of bioactivity for protecting plants against fungal diseases or superior properties for use as active ingredients in agrochemicals (e.g., higher bioactivity, favorable activity spectrum, increased safety (including improved crop tolerance), improved physicochemical properties, or increased biodegradability).

[0462] Examples of preparations

[0463]

[0464] The combination is thoroughly mixed with these additives and the mixture is thoroughly ground in a suitable grinder to provide a wettable powder that can be diluted with water to obtain a suspension of the desired concentration.

[0465]

[0466] The combination is thoroughly mixed with these adjuvants and the mixture is thoroughly ground in a suitable grinder to provide a powder that can be used directly for seed treatment.

[0467] Emulsifiable concentrate

[0468]

[0469] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting this concentrate with water.

[0470]

[0471] A ready-to-use dust powder is obtained by mixing the mixture with a carrier and grinding the mixture in a suitable grinder. This type... dust Powder can also be used for dry seed dressing.

[0472] Extruder granules

[0473]

[0474] The mixture is then combined with these additives and ground, and the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0475] Coated granules

[0476]

[0477] The finely ground mixture is then uniformly applied in a mixer to kaolin moistened with polyethylene glycol. This process yields dust-free coated granules.

[0478] suspension concentrate

[0479]

[0480] The finely ground combination is tightly mixed with these auxiliary agents to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants along with their propagation material can be treated and protected against microbial infection by spraying, watering, or immersion.

[0481] Flowable concentrate for seed treatment

[0482]

[0483] The finely ground mixture is then tightly combined with these adjuvants to obtain a flowable concentrate, from which solutions of any desired dilution can be obtained by dilution with water. This concentrate can be used directly for seed treatment. Using such dilutions, living plants, along with their propagation material, can be treated and protected against microbial infections through spraying, watering, or immersion.

[0484] Sustained-release capsule suspension

[0485] 28 parts of the mixture were mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water were added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contained 28% of the active ingredient. The median particle size of the capsules was 8-15 micrometers. The resulting formulation was applied to seeds as an aqueous suspension suitable for this purpose.

[0486] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), dispersible oil suspensions (OD), oil suspensions (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0487] abbreviation

[0488]

[0489] Preparation Examples

[0490] The compounds having formula (I) according to the present invention can be prepared using the synthesis techniques described above and below.

[0491] Throughout this specification, temperatures are given in degrees Celsius and "mp" refers to the melting point.

[0492] Recorded on a Bruker 400MHz spectrometer 1 H NMR and19 F NMR measurements, chemical shift relative to TMS ( 1 H) and CFCl3 ( 19 F) Standards are given in ppm. Spectra were measured in deuterated solvents as indicated. Compounds were characterized using any of the following LC-MS methods. Characteristic LC-MS values ​​obtained for each compound are retention time (“Rt”, recorded in minutes) and the measured molecular ion (M+H). + Or (MH) - .

[0493] LC-MS Method A: Spectroscopy was recorded on a Waters mass spectrometer (Acquity QDa mass spectrometer) equipped with an electro-jet source (polarity: positive and negative polarity switching), capillary voltage: 0.8 kV, cone range: 25 V, extractor: V (QDa detector has no extractor voltage), source temperature: 120°C, desolvation temperature: 600°C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 1000 L / h, mass range: 110 to 850 Da, and a Waters Acquity UPLC: quaternary solvent manager, heated column chamber, and diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 µm, 30 x 2.1 mm, Temperature: 40°C, DAD wavelength range (nm): 200 to 400, Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH; Gradient: 0 min 10% B; 0.0-0.2 min 10%-50% B; 0.2-0.6 min 50%-100% B; 0.6-1.3 min 100% B; 1.3-1.4 min 100%-10% B; 1.4-1.6 min 10% B; Flow rate (mL / min): 0.6.

[0494] LC-MS Method B:Spectra were recorded on an Agilent Technologies MSD-IQ mass spectrometer equipped with an electro-ejector source (polarity: positive or negative ion, MS2 scan, capillary voltage: 3.5 kV, fragmentation voltage: 110 V, desolvation temperature: 325°C, gas flow rate: 13 L / min, nebulizer gas: 55 psi, mass range: 110 to 850 Da) and an Agilent 1290 series HPLC: quaternary pump, heated column chamber, and diode array detector. Column: AGILENT POROSHELL 120 EC-C18, 1.9 µm, 50 x 2.1 mm; Temperature: 40°C; DAD wavelength range (nm): 190 to 400; Solvent gradient: A = Water + 5% acetonitrile + 0.1% HCOOH, B = Acetonitrile + 0.1% HCOOH; Gradient: 0–0.5 min 10% B, 90% A; 1.2–1.5 min 95% B, 5% A; 1.8–2.5 min 10% B, 90% A; Flow rate (mL / min): 0.8

[0495] LC-MS Method C: Spectra were recorded on a mass spectrometer (6410 triple quadrupole mass spectrometer) from Agilent Technologies, equipped with an electro-ejector source (polarity: positive or negative ion, MS2 scan, capillary voltage: 4.00 kV, fragmentation voltage: 100 V, desolvation temperature: 350°C, gas flow rate: 11 L / min, nebulizer gas: 45 psi, mass range: 110 to 1000 Da) and an Agilent 1200 Series HPLC: quaternary pump, heated column chamber, and VWD detector. Column: KINETEX EVO C18, 2.6 µm, 50 x 4.6 mm, temperature: 40°C, detector VWD wavelength: 254 nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH; gradient: 0 min 10% B, 90% A; 0.9–1.8 min 100% B; 1.8–2.2 min 100%–10% B; 2.2–2.5 min 10% B; flow rate (mL / min) 1.8.

[0496] Preparation Example-1: N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl]-1- Preparation of (2,4-difluorophenyl)triazole-4-carboxamide (compound P-2, Table P)

[0497] Compound P-2, Table P

[0498] Step 1: Preparation of 5-methoxy-1-methyl-pyrazole-4-carboxaldehyde

[0499]

[0500] Sodium methoxide (18.3 mL, 17.8 g, 82.1 mmol) was added to a solution of 5-chloro-1-methylpyrazol-4-carboxaldehyde (CAS [117007-77-9], 6.25 g, 41.1 mmol) in methanol (62.5 mL) at room temperature under argon atmosphere. The resulting reaction mixture was stirred at 60°C for 6 h, after which LCMS and TLC showed the reaction was complete. The reaction mixture was diluted with water (50 mL) and a saturated aqueous solution of ammonium chloride and extracted with EtOAc (150 mL x 3). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give a crude product. The crude product was adsorbed onto diatomaceous earth and purified by combined flash chromatography (eluting with 30%–60% EtOAC / cyclohexane) to give the title compound.

[0501] 1 H NMR (400 MHz, CDCl3) δ ppm 9.74 (s, 1 H) 7.78 (s, 1 H) 4.30 (s, 3H) 3.67 (s, 3 H)

[0502] Step 2: Preparation of 2-(5-methoxy-1-methyl-pyrazole-4-yl)acetonitrile

[0503]

[0504] A potassium tert-butoxide sample (2.11 g, 18.35 mmol) in 1,2-dimethoxyethane (DME, 200 mL) was cooled to -65°C and treated under argon with p-toluenesulfonyl-methylisocyanate (2.09 g, 10.49 mmol) in DME (5 mL). The reaction mixture was stirred at -65°C to -60°C for about 1–2 hr. At -65°C to -60°C for 1 hr, 5-methoxy-1-methyl-pyrazole-4-carboxaldehyde (1.05 g, 7.5 mmol) in DME (8 mL) was added to this mixture. Stirring was continued at this temperature for 2 hr. Methanol (0.8 mL) was added at -65°C to obtain a clear solution, and the reaction mixture was then heated to 80°C for 2 h. After the reaction was complete (monitored by LCMS and TLC), it was cooled to 0°C and quenched with 5% acetic acid in water (until the pH became slightly acidic), stirred for 5 min, and diluted with EtOAc (50 mL). The aqueous and organic layers were separated, and the aqueous layer was back-extracted with EtOAc (60 mL). The combined organic layers were washed with a brine solution (10 mL), dried over Na2SO4, and concentrated under vacuum. The crude product was adsorbed onto diatomaceous earth and purified using combined flash chromatography (eluting with 20%–50% EtOAc) to obtain the pure title compound as a brown liquid.

[0505] LC-MS (Method A): Retention time 0.19 min, m / z = 152 (M+H). 1 H NMR (400 MHz, CDCl3)δ ppm: 7.32 (s, 1 H); 3.98 (s, 3 H); 3.69 (s, 3 H); 3.52 (s, 2 H).

[0506] Step 3: Preparation of 2-(5-methoxy-1-methyl-pyrazole-4-yl)propionitrile

[0507]

[0508] A solution of potassium tert-butoxide (151 mg, 1.32 mmol) and 2-(5-methoxy-1-methyl-pyrazol-4-yl)acetonitrile (200 mg, 1.32 mmol) in THF (4 mL) was cooled to 0°C, stirred at room temperature, and then treated with iodomethane (210 mg, 1.45 mmol). The reaction mixture was heated to room temperature and stirred at this temperature (monitored by LCMS and TLC). After the reaction was complete, the mixture was diluted with water (20 mL) and a saturated aqueous solution of ammonium chloride (10 mL). The mixture was extracted with EtOAc (60 mL x 3), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum to obtain the crude compound. It was adsorbed onto diatomaceous earth and purified by combined flash chromatography (eluting with 50%–60% EtOAc in cyclohexane) to obtain the pure title compound.

[0509] LCMS (Method A): Retention time: 0.91 min, m\z = 166 (M+H). 1 H NMR (400 MHz, CDCl3): δ ppm 7.34 (s, 1 H); 3.97 (s, 3 H); 3.78-3.84 (m, 1 H); 3.71 (s, 3H); 1.60 - 1.65 (m, 3 H).

[0510] Step 4: Preparation of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propionitrile

[0511]

[0512] A solution of 2-(5-methoxy-1-methyl-pyrazol-4-yl)propionitrile (400 mg, 2.42 mmol) in THF (8 mL) was cooled to -10°C to -15°C and treated with potassium tert-butoxide (277 mg, 2.42 mmol). 2,6-Dichloropyridine (376 mg, 2.54 mmol) in THF (1.5 mL) was added to this solution. The reaction mixture was heated to room temperature and stirred under N2. After the reaction was complete (monitored by LCMS), the mixture was diluted with cold water (10 mL) and extracted with EtOAc (30 mL, x 3). The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum to obtain the crude compound. This crude compound was adsorbed onto diatomaceous earth and purified by combined flash chromatography (eluting with 40%–50% EtOAc in cyclohexane) to obtain the title compound as a yellow gel.

[0513] LC-MS (Method A): Retention time 1.01 min, m / z = 277 (M+H). 1H NMR (400 MHz, CDCl3)δ ppm 7.61 (t, J=7.82 Hz, 1 H) 7.39 (dd, J=7.63, 0.63 Hz, 1 H) 7.26 (s, 1 H)7.19 - 7.23 (m, 1 H) 3.90 (s, 3 H) 3.63 (m, 3 H) 2.03 (s, 3 H)

[0514] Step 6: Preparation of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl-1-amine

[0515]

[0516] At room temperature under nitrogen, a borane dimethyl sulfide complex (3.3 mL, 6.5 mmol) was added to a solution of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propionitrile (0.65 mmol, 360 mg) in THF (2 mL). The resulting reaction mixture was stirred at 60°C for 1 h (monitored by LCMS). After completion, the solution was cooled and then carefully treated with dropwise addition of 6 N HCl (0.44 mL, 2.61 mmol, strong gas escaping!) and stirred at 60°C for 1 h. After cooling to room temperature, it was alkalized to pH 12 with 6 N NaOH and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. This gave the title compound as a yellow oil, which was used in the following steps without further purification.

[0517] LC-MS (Method A): Retention time 0.27 min, m / z = 281 / 283 (M+H)

[0518] Step 7: Preparation of methyl 1-(2,4-difluorophenyl)triazole-4-carboxylate

[0519]

[0520] A solution of 1-azido-2,4-difluorobenzene (0.30 g, 1.8 mmol) in methanol (3.6 mL) was treated sequentially with anhydrous copper(II) sulfate (0.053 g, 0.33 mmol), sodium ascorbate in water (3.6 mL) (0.46 g, 2.3 mmol), and then methyl propionate (0.14 g, 0.14 mL, 1.7 mmol). The slightly reddish reaction mixture was stirred at room temperature for 2 days (monitored by LCMS). The reaction mixture was then concentrated under vacuum, and the residue was adsorbed onto water and EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The crude product was adsorbed onto Isolute and purified by silica gel column chromatography (Rf200) (eluting with cyclohexane / EtOAc) to give the title compound as a white solid.

[0521] LC / MS (Method A); retention time 0.79 min, m / z=240 [M+H]. 1 H NMR (400 MHz, CDCl3)δ ppm 4.02 (s, 3 H) 7.09 - 7.17 (m, 2 H) 7.96 - 8.05 (m, 1 H) 8.59 (d, J=2.57Hz, 1 H)

[0522] Step 8: Preparation of 1-(2,4-difluorophenyl)triazole-4-carboxylic acid

[0523]

[0524] Under argon atmosphere, methyl 1-(2,4-difluorophenyl)triazole-4-carboxylate sample (0.31 g, 1.3 mmol) was dissolved in THF (6.5 mL) and water (3.2 mL) to give a pale brown solution. LiOH·H₂O (0.047 g, 1.9 mmol) was then added and the mixture was stirred at room temperature. After 3 hr, the desired mass and starting material consumption were measured by LC / MS at rt = 0.63 min. The sample was concentrated under vacuum, and the residue was absorbed in water and EtOAc, and the mixture was acidified with 2 N HCl. The organic layer was separated, dried over Na₂SO₄, filtered, and concentrated under vacuum to give the title compound as a white solid.

[0525] LC / MS (Method A): Retention time 0.63 min, m / z = 226 [M+H]. 1H NMR (400 MHz, DMSO) δppm 7.27 - 7.52 (m, 1 H) 7.73 (ddd, J=11.10, 8.71, 2.57 Hz, 1 H) 7.95 (td, J=8.80, 5.87 Hz, 1 H) 9.15 (d, J=1.47 Hz, 1 H) 13.26 - 13.60 (m, 1 H)

[0526] Step 9: N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl]-1-(2,4- Preparation of difluorophenyl)triazole-4-carboxamide (compound P-2, Table P)

[0527] A solution of 1-(2,4-difluorophenyl)triazol-4-carboxylic acid (44 mg, 0.185 mmol) and 2-(6-chloro-2-pyridyl)-2-(5-methoxy-1-methyl-pyrazol-4-yl)propyl-1-amine (130 mg, 0.185 mmol) in EtOAc (4 mL) was treated with DIPEA (98 mg, 0.74 mmol) and 1-propanephosphonic anhydride (300 mg, 0.27 mL, 0.463 mmol) at 0°C, and the reaction mixture was stirred at room temperature (monitored by LCMS). After the reaction was complete, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under vacuum to obtain the crude product. The compound was purified by reversed-phase combined flash chromatography (eluting with 60%-80% water in CH3CN) to obtain the title compound as a white solid.

[0528] LCMS (Method A) retention time: 1.09; m / z = 488 (M+H). 1 H NMR (400 MHz, CDCl3) δ ppm8.50 (d, J=2.63 Hz, 1 H) 8.18 (t, J=6.30 Hz, 1 H) 7.88-7.94 (dd, J=8.76, 5.75Hz, 1 H) 7.57-7.61 (t, J=7.82 Hz, 1 H) 7.27 (s, 1 H) 7.21-7.23 (d, J=7.75 Hz, 1 H) 7.18-7.16 (d, J=7.75 Hz, 1 H) 7.07-7.12 (t, J=8.60 Hz, 2 H) 4.10 - 4.24(m, 2 H) 3.70 (s, 3 H) 3.59 (s, 3 H) 1.74 (s, 3 H). 19F NMR (377 MHz, CDCl3) δppm -106.38 (s, 1 F) -118.48 (s, 1 F)

[0529] Preparation Example-2: N-[2-(6-cyano-2-pyridyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propane] Preparation of 1,2-(2,4-difluorophenyl)tetrazole-5-carboxamide (Example P-1, Table P)

[0530] Instance P-1, Table P

[0531] Step 1: Preparation of 5-chloro-1,3-dimethyl-pyrazole-4-carboxaldehyde

[0532]

[0533] A solution of 2,5-dimethylpyrazol-3-ol (10 g, 44.6 mmol) and phosphorus oxychloride (V) (21.2 mL) was stirred at 90°C for 1 h. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was concentrated under vacuum and the residue was treated with a saturated aqueous sodium bicarbonate solution (until the pH was alkaline). The aqueous layer was extracted with EtOAc (50 mL x 3), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under vacuum to obtain the crude product. The crude product was purified by a combined flash chromatography method using 20%–30% EtOAc in cyclohexane to obtain 5-chloro-1,3-dimethylpyrazol-4-carboxaldehyde as a white solid.

[0534] LCMS (Method B): Retention time 1.0 min, m / z = 159 (M+H)

[0535] Step 2: Preparation of 5-methoxy-1,3-dimethyl-pyrazole-4-carboxaldehyde

[0536]

[0537] Sodium methoxide (23 mL, 100 mmol) was added to a solution of 5-chloro-1,3-dimethyl-pyrazole-4-carboxaldehyde (8.3 g, 52 mmol) in methanol (83 mL) at room temperature under argon atmosphere. The resulting reaction mixture was stirred at 60°C for 6 h, after which LCMS and TLC showed the reaction was complete. The reaction mixture was diluted with water (50 mL) and a saturated aqueous solution of ammonium chloride and extracted with EtOAc (150 mL x 3). The combined organic layers were dried over Na₂SO₄ and concentrated under vacuum to give a crude product. This crude product was purified by combined flash chromatography with 30%–40% EtOAc in cyclohexane to give the title compound as a white solid.

[0538] LC-MS (Method A): Retention time 0.34 min, m / z = 155 (M+H)

[0539] Step 3: Preparation of 2-(5-methoxy-1,3-dimethyl-pyrazole-4-yl)acetonitrile

[0540]

[0541] A potassium tert-butoxide sample (11 g, 95 mmol) in 1,2-dimethoxyethane (130 mL) was cooled to -65°C and treated under argon with p-toluenesulfonyl-methylisocyanate (11 g, 54 mmol) in DME (5 mL). The reaction mixture was stirred at -65°C to -60°C for about 1 to 2 hours. At -65°C to -60°C, within 1 hour, 5-methoxy-1,3-dimethyl-pyrazole-4-carboxaldehyde (6.3 g, 39 mmol) in DME (5 mL) was added to this mixture. Stirring was continued at this temperature for 2 hours (note: a thick substance was observed). Methanol (4.1 mL) was added at -65°C to give a clear solution. The reaction mixture was then heated to 80°C for 2 hours. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was cooled to 0°C and quenched with 5% acetic acid in water (until the pH became slightly acidic), stirred for 5 min, and diluted with EtOAc (10 mL). The aqueous and organic layers were separated, and the aqueous layer was extracted with EtOAc (60 mL). The combined organic layers were washed with a brine solution (10 mL), dried over Na2SO4, and concentrated under vacuum. The crude compound was purified by a combined flash chromatography using 50%–70% EtOAc in cyclohexane to give the title compound as a brown liquid.

[0542] LC-MS (Method B): Retention time 0.74 min, m / z = 166 (M+H)

[0543] Step 4: Preparation of 2-(5-methoxy-1,3-dimethyl-pyrazole-4-yl)propionitrile

[0544]

[0545] A solution of potassium tert-butoxide (83 mg, 0.72 mmol) and 2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)acetonitrile (100 mg, 0.60 mmol) in DMSO (1 mL) was stirred at room temperature. After 10 min, iodomethane (0.042 mL, 0.66 mmol) was added, and the reaction mixture was stirred at room temperature under nitrogen for 30 min. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was diluted with cold water (20 mL) and a saturated aqueous solution of ammonium chloride and extracted with EtOAc (40 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. The crude compound was purified by combined flash chromatography with 50%–60% EtOAc in cyclohexane to give the title compound as a colorless liquid.

[0546] LC-MS (Method B): Retention time 1.31 min, m / z = 180 (M+H)

[0547] Step 5: Preparation of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propionitrile

[0548]

[0549] A solution of 2-(5-methoxy-1,3-dimethylpyrazol-4-yl)propionitrile (1.5 g, 6.7 mmol) in DMSO (15 mL) and potassium tert-butoxide (1.2 g, 11 mmol) was stirred at room temperature, and after 10 min, 2,6-dichloropyridine (1.1 g, 7.4 mmol) was added dropwise to DMSO (5 mL). The reaction mixture was stirred at room temperature under nitrogen for 30 min. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was diluted with cold water (20 mL) and saturated ammonium chloride and extracted with EtOAc (40 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. The crude product was purified by combined flash chromatography with 50%–70% EtOAc in cyclohexane to give the title compound as a yellow oil.

[0550] LC-MS (Method A): Retention time 1.06 min, m / z = 291 (M+H)

[0551] Step 6: Preparation of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl-1-amine

[0552]

[0553] At room temperature under nitrogen, a borane dimethyl sulfide complex (21 mL, 42.1 mmol) was added to a solution of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propionitrile (1.53 g, 4.21 mmol) in THF (12.6 mL). The resulting reaction mixture was stirred at 70°C for 1 h (monitored by LCMS). After completion, the solution was carefully treated dropwise with 6 N HCl (0.95 mL, 5.75 mmol, strong gas escaping!) and stirred at 60°C for 1 h. After cooling to room temperature, it was basted to pH 12 with 6 N NaOH and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. This gave the title compound as a yellow oil, which was used in the following steps without further purification.

[0554] LC-MS (Method A): Retention time 0.13 min, m / z = 295 (M+H).

[0555] Step 7: N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]amino Preparation of tert-butyl formate

[0556]

[0557] A solution of 2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl-1-amine (1.5 g, 4.3 mmol) in THF (23 mL) and water (15 mL) was stirred at 0°C, and sodium bicarbonate (1.7 g, 19 mmol) and di-tert-butyl dicarbonate (1.1 mL, 4.3 mmol) were added at 0°C. The resulting reaction mixture was stirred at room temperature for 2 h. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was quenched with water, and the aqueous layer was extracted with EtOAc (X3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under vacuum to obtain the crude product. The crude compound was purified by combined flash chromatography using 60%-80% EtOAc in cyclohexane to obtain N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl] tert-butyl carbamate (1.4 g, 74%), which was a yellow oil.

[0558] LCMS (Method A): Retention time 1.11 min, m / z = 395 (M+H)

[0559] Step 8: N-[2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]amino Preparation of tert-butyl carbamate

[0560]

[0561] A solution of N-[2-(6-chloro-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]tert-butyl carbamate (1.4 g, 3.2 mmol) in toluene (7.0 mL) and water (7.0 mL) was stirred at room temperature. Potassium acetate (0.89 g, 8.9 mmol) and potassium ferrocyanide (4.9 g, 13 mmol) were added to this reaction mixture, and the reaction mixture was further degassed with nitrogen for 10 min. Under nitrogen, palladium(II) methanesulfonate (1.4 g, 1.6 mmol) was added, and the reaction mixture was heated at 90°C for 4 hr. After the reaction was complete (monitored by LCMS and TLC), the reaction mixture was quenched with water, and the aqueous layer was extracted with EtOAc (X3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under vacuum to obtain the crude product. The crude compound was purified by combined flash chromatography with 80% EtOAc in cyclohexane to give N-[2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]carbamate (1.0 g, 69%) as a brown oil.

[0562] LCMS (Method B): Retention time 1.76 min, m / z = 386 (M+H)

[0563] Step 9: [2-(6-cyano-2-pyridyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]chlorination Preparation of ammonium

[0564]

[0565] At 0°C, 2 M HCl (1.49 mL, 2.98 mmol) in diethyl ether was added dropwise to a solution of N-[2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]carbamate (320 mg, 0.74 mmol) in diethyl ether (3.2 mL). The reaction mixture was heated to room temperature and stirred at room temperature for 6 h (monitored by LCMS). The reaction mixture was concentrated under vacuum at 30°C to give a yellow solid of [2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]ammonium chloride (290 mg, 96%). The crude product was used as is in the next step.

[0566] LCMS (Method A): Retention time 0.39 min, m / z = 286 (M+H)

[0567] Step 10: Preparation of (2E)-2-(p-Toluenesulfonylhydrazine)ethyl acetate

[0568]

[0569] A solution of 4-methylbenzenesulfonylhydrazine (CAS [1576-35-8], 2 g, 10.73 mmol) in ethanol (40 mL) was treated with ethyl 2-oxoacetate (2.63 g, 12.88 mmol) at room temperature. The reaction mixture was stirred for 1 hr, and the ethanol was removed by vacuum concentration. The resulting residue was diluted with water and extracted with EtOAc. The organic phase was separated, and the solvent was evaporated under vacuum to give ethyl (2E)-2-(p-toluenesulfonylhydrazine)acetate, which was used as is in the next step (step 2).

[0570] LCMS (Method C): Retention time 1.04 min, m / z = 271 [M+H]. 1 H NMR (400 MHz, CDCl3)δ ppm 9.31 (s, 1 H) 7.85 (d, J=8.31 ​​Hz, 2 H) 7.34 (d, J=8.07 Hz, 2 H) 7.23 (s, 1 H) 4.27 (q, J=7.09 Hz, 2 H) 2.44 (s, 3 H) 1.23 - 1.37 (m, 3H).

[0571] Step 11: Preparation of ethyl 2-(2,4-difluorophenyl)tetrazole-5-carboxylate

[0572]

[0573] A 2,4-difluoroaniline sample (1 g, 7.74 mmol) was dissolved in 6 M HCl aqueous solution (deionized water) (6 mL, 36 mmol) and ethanol (5 mL) and cooled to 0°C. Sodium nitrite (0.64 g, 9.29 mmol) was added to this solution, and the resulting reaction mixture was stirred at 0°C for 1 hr, and then added dropwise to a solution of (2E)-2-(p-toluenesulfonylhydrazine)ethyl acetate (2.3 g, 8.51 mmol) in pyridine (20 mL) at -20°C. The reaction mixture was slowly heated to room temperature and then stirred for 5 hr. The resulting reaction mixture was diluted with 1 N HCl, and the aqueous layer was extracted with EtOAc (20 mL x 3). The combined organic layers were dried with Na2SO4 and concentrated under vacuum to obtain a crude product, which was then purified by column chromatography (eluting with 30% EtOAc in hexane) to obtain ethyl 2-(2,4-difluorophenyl)tetrazole-5-carboxylate, which was a slightly red oil.

[0574] LCMS (Method B): [M+H+] not detected; retention time = 1.10 min; 1 H NMR (400 MHz, CDCl3) δppm 7.86 - 7.94 (m, 1 H) 7.11 - 7.21 (m, 2 H) 4.60 (q, J=7.21 Hz, 2 H) 1.51 (t, J=7.13 Hz, 3 H)

[0575] Step 12: Preparation of 2-(2,4-difluorophenyl)tetrazole-5-carboxylic acid

[0576]

[0577] At room temperature, LiOH·H₂O (0.113 mg, 4.72 mmol) was added to a stirred solution of methyl 5-methylisoxazole-3-carboxylate (300 mg, 1.18 mmol) in THF (3 mL) and water (1.5 mL), and the reaction mixture was stirred at room temperature for 30 min. The organic solvent was removed by vacuum concentration, and the aqueous residue was diluted with 2 N HCl and then extracted with EtOAc (3 × 20 mL). The combined organic phases were dried over Na₂SO₄, filtered, and concentrated under vacuum to give a faint red solid, 2-(2,4-difluorophenyl)tetrazolium-5-carboxylic acid.

[0578] LCMS (Method C): Retention time = 0.87–1.11 min, 227 [M+H]; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.10 (td, J=8.69, 5.75 Hz, 1 H) 7.73 - 7.88 (m, 1 H) 7.40 -7.50 (m, 1 H) 3.36 - 3.63 (m, 3 H) 3.07 - 3.35 (m, 3 H) 1.99 (s, 1 H) 1.91 (s, 1 H) 1.24 (s, 1 H)

[0579] Step 13: N-[2-(6-cyano-2-pyridyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]- Preparation of 2-(2,4-difluorophenyl)tetrazole-5-carboxamide (compound P-1, Table P)

[0580] A solution of 2-(2,4-difluorophenyl)tetrazole-5-carboxylic acid (61 mg, 0.21 mmol) and [2-(6-cyano-2-pyridinyl)-2-(5-methoxy-1,3-dimethyl-pyrazol-4-yl)propyl]ammonium chloride (80 mg, 0.19 mmol) in EtOAc (20 mL) was treated with DIPEA (0.15 mL, 0.79 mmol) and 1-propanephosphonic anhydride (379 mg, 0.35 mL, 0.59 mmol) at 0°C, and the reaction mixture was stirred at room temperature (monitored by LCMS). After the reaction was complete, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under vacuum to obtain the crude product. The compound was purified by reversed-phase combined flash chromatography (eluting with 40%-60% water in CH3CN) to obtain the title compound as a colorless solid.

[0581] LCMS (Method A) retention time: 1.02; m / z = 494 (M+H); 1 H NMR (400 MHz, CDCl3) δ ppm8.33-8.36 (br t, J=6.44 Hz, 1 H), 7.89 - 7.94 (m, 1 H), 7.75 - 7.77 (m, 1 H),7.62-7.64 (d, J=7.63 Hz, 1 H), 7.46-7.48 (d, J=8.25 Hz, 1 H), 7.10 - 7.14 (m,2 H), 4.16-4.18 (br d, J=6.63 Hz, 2 H), 3.86 (s, 3 H), 3.67 (s, 3 H), 1.79(s, 3 H),1.65 (s, 3 H)

[0582] 19 F NMR (376 MHz, CDCl3) δ ppm -103.80 (s, 1 F) -114.75 (s, 1 F)

[0583] Examples of synthesized compounds are shown in Table P.

[0584] Table P: Synthesized compounds and their spectral and physicochemical data

[0585]

[0586] Biological examples

[0587] Example B1: Alternaria solani / Tomato / (Early blight)

[0588] Tomato leaf disc cultivar Baby was placed on agar in a multi-well plate (24-well size) and sprayed with a prepared test compound diluted in water. Two days after application, the leaf discs were inoculated with a suspension of fungal spores. The inoculated leaf discs were incubated in a climate chamber under a 12 / 12 h (light / dark) light program, at 23°C / 21°C (day / night) and 80% rh, and the activity of the compounds was assessed as the percentage of disease control compared to untreated leaf discs when an appropriate level of disease damage was observed (5 to 7 days after application). The following compounds gave at least 80% control of Alternaria solanacearum at 200 ppm compared to an untreated control showing extensive disease development under the same conditions: P-1, P-2, P-3, P-4.

[0589] Example B2: Wheat powdery mildew fungus (Blumeria graminis f. sp. tritici) (Erysiphe graminis f. sp. tritici) / wheat / (powdery mildew on wheat)

[0590] Wheat leaf segments of the cultivar Cansler were placed on agar in multi-well plates (24-well size) and sprayed with a prepared test compound diluted in water. One day after application, leaf discs were inoculated by shaking powdery mildew-infected plants over these test plates. The inoculated leaf discs were incubated in a climate chamber at 20°C and 60% RH under a light scheme of 24 h dark followed by 12 h light / 12 h dark, and the activity of the compounds was assessed as the percentage of disease control compared to untreated leaves when an appropriate level of disease damage was observed on untreated test leaf segments (6 to 8 days after application). The following compounds, P-1, P-2, P-3, and P-4, provided at least 80% control against the wheat-specific *Brucella gramineus* at 200 ppm when compared to an untreated control showing extensive disease development under the same conditions.

[0591] Example B3: Phaeosphaeria nodorum (Septoria nodorum) / wheat / (glume spot) blight)

[0592] Wheat leaf cultivar Cansler was placed on agar in a multi-well plate (24-well size) and sprayed with a prepared test compound diluted in water. Two days after application, leaf discs were inoculated with a suspension of fungal spores. The inoculated test leaf discs were incubated in a climate chamber at 20°C and 75% rh under a 12 h light / 12 h dark light scheme, and the activity of the compounds was assessed as the percentage of disease control compared to untreated leaf discs when an appropriate level of disease damage was observed (5 to 7 days after application). The following compounds gave at least 80% control of *Needophyllum glomerulosa* at 200 ppm when compared to an untreated control showing extensive disease development under the same conditions: P-1, P-2, P-3, and P-4.

[0593] Example B4: Pyrenophora teres / Barley / (Net blotch)

[0594] Barley leaf segments of the cultivar Hasso were placed on agar in multi-well plates (24-well size) and sprayed with a prepared test compound diluted in water. Two days after application, the leaf segments were inoculated with a suspension of fungal spores. The inoculated leaf segments were incubated in a climate chamber at 20°C and 65% rh under a 12 h light / 12 h dark light scheme, and the activity of the compounds was assessed as disease control compared to untreated control leaf segments when an appropriate level of disease damage was observed (5 to 7 days after application). The following compounds provided at least 80% control of *Rhizoctonia solani* at 200 ppm compared to untreated controls showing extensive disease development under the same conditions: P-1, P-2, P-3, and P-4.

[0595] Example B5: *Septoria blotch* (wheat spore) / (leaf blight)

[0596] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). Nutrient broth containing fungal conidia was added after a solution of the test compound (DMSO) was placed in a microtiter plate (96-well size). The test plate was incubated at 24°C, and growth inhibition was determined photometrically 4–5 days after application. The following compounds, at 20 ppm, provided at least 80% control of *Cyclocarya granatum* compared to the untreated control, which showed extensive disease development under the same conditions: P-1, P-2, P-3, and P-4.

[0597] Example B6: Botryotinia fuckeliana (Botryotinia fuckeliana) (Gray mold)

[0598] Fungal conidia from frozen storage were directly mixed into nutrient broth (Vogels broth). Nutrient broth containing fungal conidia was added after a solution of the test compound (DMSO) was placed in a microtiter plate (96-well size). The test plate was incubated at 24°C, and growth inhibition was determined photometrically 3 to 4 days after application. The following compounds, at 20 ppm, provided at least 80% control against *Botrytis cinerea* at comparison with an untreated control showing extensive disease development under the same conditions: P-2, P-4.

[0599] Example B7: Mycosphaerella arachidis (Cercospora arachidis) / (Early Leaf Spot) sick)

[0600] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). Nutrient broth containing fungal conidia was added after a solution of the test compound (DMSO) was placed in a microtiter plate (96-well size). The test plate was incubated at 24°C, and growth inhibition was determined photometrically 4–5 days after application. The following compounds, at 20 ppm, provided at least 80% control of *P. arachidica* at the same concentration compared to an untreated control showing extensive disease development under the same conditions: P-2, P-3, and P-4.

Claims

1. A compound having formula (I) or an agrochemically acceptable salt or N-oxide thereof, (I) in R 1 Selected from hydrogen, C1-C 4- Alkyl, C2-C 4- alkenyl, C2-C4-alkynyl, or C3-C 6- cycloalkyl; R 2 Selected from cyano, hydroxy, amino, C1-C4-alkoxy, C3-C6-enoxy, C3-C6-alkynoxy, C3-C6-cycloalkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C1-C4-haloalkylthioalkyl; R 3 Selected from hydrogen, halogens, or C1-C4-alkyl groups; R 4 Selected from hydrogen, halogen, cyano, or C1-C4-alkyl; R 5 and R 6 Independently selected from hydrogen or C1-C4-alkyl; A 1 Selected from CR 7 Or N; A 2 Selected from CR 8 Or N; A 3 Selected from CR 9 Or N; R 7 R 8 and R 9 It is independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C1-C4-haloalkyl; Q is selected from a 6-membered heteroaryl group, wherein any one of the 6-membered heteroaryl groups is selected from... The interlacing lines represent bonds to the remainder of the molecule; and each of the six heteroaryl groups is unsubstituted or independently selected from R by one or up to a maximum possible number of R groups. 10 Substituents, wherein R 10 Independently selected from halogen, hydroxyl, cyano, carboxyl, amino, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-enoxy, C2-C4-alkynoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, trifluoromethanesulfonyloxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, N-C1-C4-alkylamino, N,N-di(C1-C4)-alkylamino, C1-C 4- Alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimide, N-hydroxy-C1-C 4- alkyl-carbonimide, phenyl, 5- or 6-membered heteroaryl, or C3-C 6- The cycloalkyl group, wherein any one of the 5- or 6-membered heteroaryl groups comprises 1, 2, 3, or 4 heteroatoms individually selected from N, O, or S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl group, and C3-C6-cycloalkyl group is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy; and Z 1 The group is selected from C1-C4-alkyl, phenyl, 5- or 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein any one of the 5- or 6-membered heteroaryl groups contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, provided that only one is selected from O or S; and wherein any one of the phenyl, 5- or 6-membered heteroaryl, and C3-C6-cycloalkyl groups is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthioalkyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, or C2-C4-ynyl.

2. The compound according to claim 1, wherein, R 1 It is a C1-C3-alkyl group; and R 5 and R 6 It is hydrogen.

3. The compound according to claim 1 or claim 2, wherein, R 3 It is hydrogen or C1-C3-alkyl; and R 4 It is either hydrogen or methyl.

4. The compound according to any one of claims 1 to 3, wherein, R 2 It is C1-C3-alkoxy, C1-C2-haloalkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl.

5. The compound according to claim 4, wherein, R 2 It is C1-C3-alkoxy, C1-C4-alkoxy-C1-C2-alkyl, or C1-C2-alkylthioalkyl.

6. The compound according to any one of claims 1 to 5, wherein, Q is selected from The interlacing lines represent bonds to the remainder of the molecule; wherein any one of the six heteroaryl groups Q1, Q2, Q3, and Q4 is unsubstituted or is formed by one or two independently selected from R 10 Substituents of R, wherein R 10 It is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl.

7. The compound according to any one of claims 1 to 6, wherein, Q is Q1, where Q1 is unsubstituted or is selected independently from R by one or two factors. 10 Substituents of R, wherein R 10 It is selected from halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, or C3-C6-cycloalkyl.

8. The compound according to any one of claims 1 to 7, wherein, Z 1 The aryl group is selected from phenyl, or 5-membered or 6-membered heteroaryl; wherein any one of the 5-membered or 6-membered heteroaryl groups contains one heteroatom selected from N, O and S; and wherein the phenyl and any one of the 5-membered or 6-membered heteroaryl groups are unsubstituted or substituted by one or two substituents independently selected from the following: chlorine, fluorine, C1-C2-alkyl, C1-C2-alkoxy, or C2-C4-alkynyl.

9. The compound according to claim 8, wherein, Z 1 It is 4-fluorophenyl, 2,4-difluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 2,6-difluoro-3-pyridyl, 3,4-difluoro-2-pyridyl, or 3,5-difluoro-2-pyridyl.

10. The compound having formula (I) according to any one of claims 1 to 9, wherein, The compound having formula (I) is a compound having formula (IA). (I-A) Where R 1 R 2 R 3 R 4 R 5 R 6 R 10 Q and Z 1 It is as defined for compounds having formula (I) according to any one of claims 1 to 9; and A is selected from... The crossed lines represent bonds to C (=O) groups, and the arrows represent bonds to Z groups. 1 The bond of the group, and where R 7 R 8 and R 9 It is independently selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-ynyl, or C1-C4-haloalkyl.

11. The compound according to claim 10, wherein, A is selected from A1 or A2 The crossed lines represent bonds to the C (=O) group, and the arrows represent bonds to the Z group. 1 The bond of a group.

12. An agricultural chemical composition comprising an effective amount of a compound as defined in any one of claims 1 to 11, which has antifungal properties.

13. The agrochemical composition according to claim 12, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

14. A method for controlling or preventing the infection of useful plants by plant pathogenic microorganisms, wherein a fungicide effective amount of a compound as defined in any one of claims 1 to 11 or a composition comprising said compound is applied to said plant, its parts or the site thereof.

15. Use of the compound according to any one of claims 1 to 11 as a fungicide.

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