Microbicidal pyrazole derivatives

Abstract

Compounds of formula (I) which can be used as fungicides: JPEG2024546927000074.jpg59130, wherein the substituents are as defined in claim 1, and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds are provided.

Description

[Technical field]

[0001] The present invention relates to microbicidal pyrazole derivatives, for example as active ingredients having microbicidal activity, in particular fungicidal and fungicidal activity. The present 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 agrochemical compositions comprising at least one pyrazole derivative, to the preparation of these compositions, and to the use of the pyrazole derivatives or compositions in agriculture or horticulture to control or prevent infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi. Summary of the Invention

[0002] According to a first aspect of the present invention, there is provided a compound of formula (I): [ka] (In the formula, R 1 is selected from the group consisting of hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, and C3-C6 cycloalkyl; R 2 is selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl and C1-C4 alkoxycarbonyl; R 3 is selected from the group consisting of hydrogen, halogen, and C1-C4 alkyl; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, and di(C1-C4 alkylamino)carbonyl; R 5 and R 6is independently selected from the group consisting of hydrogen and C1-C4 alkyl; A 1 , A 2 and A 3 CR 7 , N, N.R. 8 , O and S, with the proviso that A 1 , A 2 and A 3 At least one of is selected from N, O and S, and A 1 , A 2 and A 3 There is only one O or one S. In the formula, R 7 and R 8 is independently selected from the group consisting of hydrogen, C1-C4 alkyl, C2-C4 alkenyl, and C2-C4 alkynyl; Q 1 , Q 2 and Q 3 CR 9 , N, N.R. 10 , O and S, with the proviso that Q 1 , Q 2 and Q 3 At least one of is N, NR 10 , O and S, and Q 1 , Q 2 and Q 3 Of which, NR 10 , there is only one O or one S; In the formula, R 9 and R 10 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, and C2-C4 alkynyl; and Z 1is selected from the group consisting of C1-C4 alkyl, phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl, wherein the 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S, and wherein any of the phenyl, 5- or 6-membered heteroaryl, and C3-C6 cycloalkyl may be optionally substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, and C2-C4 alkynyl. or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof is provided.

[0003] It has now been surprisingly found that the compounds of formula (I) have in fact a highly advantageous level of biological activity for the protection of plants against diseases caused by fungi.

[0004] According to a second aspect of the present invention there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to the present invention, such agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0005] According to a third aspect of the present invention, there is provided a method for controlling or preventing infestation of a useful plant by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound of formula (I) according to the present invention or a composition containing a compound of formula (I) to the plant, its parts or its habitat.

[0006] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) according to the present invention as a bactericide or fungicide. According to this particular aspect of the present invention, the use may not include a method involving the treatment of the human or animal body by surgery or therapy. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

[0008] As used herein, cyano refers to the group --CN.

[0009] As used herein, the terms "hydroxyl" or "hydroxy" refer to an --OH group.

[0010] As used herein, oxo refers to a =O group, e.g., a sulfinyl (-S(O)-) or sulfonyl (-S(O)2-) oxygen.

[0011] As used herein, the term "C1-C4 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having 1-4 carbon atoms, and attached to the remainder of the molecule by a single bond. The terms "C1-C3 alkyl" and "C1-C2 alkyl" should be interpreted similarly. Examples of C1-C4 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1,1-dimethylethyl (t-butyl). A "C1-C4 alkylene" group refers to the corresponding definition of C1-C4 alkyl, except that such group is attached to the remainder of the molecule by two single bonds. Examples of C1-C4 alkylene are -CH2- and -CH2CH2-.

[0012] As used herein, the term "C2-C4 alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond which may be in the (E) or (Z) configuration, having 2 to 4 carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C3-C4 alkenyl" should be interpreted similarly. Examples of C2-C4 alkenyl include, but are not limited to, ethenyl and prop-1-enyl.

[0013] As used herein, the term "C2-C4 alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having 2-4 carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C3-C4 alkynyl" should be interpreted similarly. Examples of C3-C4 alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, propargyl (prop-2-ynyl), but-1-ynyl, and 3-methyl-but-1-ynyl.

[0014] As used in this specification, "C1-C nThe term "haloalkyl" refers to a linear or branched saturated alkyl group (as described above) attached via any of the carbon atoms having 1 to n carbon atoms, in which some or all of the hydrogen atoms of these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., 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, It refers to any one of 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, or nonafluorobutyl. The term "C1-C2 fluoroalkyl" can refer to any one of C1-C2 alkyl groups carrying 1, 2, 3, 4, or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl. n "-haloalkoxy" as used herein refers to any C1-C alkoxy group, each of which is substituted with one or more halo atoms, which may be the same or different. n -refers to an alkoxyl group.

[0015] As used herein, the term "C1-C4 alkoxy" refers to R a is a C1-C4 alkyl group as generally defined above; a It refers to the group O-. The terms "C1-C3 alkoxy" and "C1-C2 alkoxy" should be interpreted similarly. Examples of C1-C4 alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy, and t-butoxy.

[0016] As used herein, the term "C1-C4 alkoxy-C1-C4 alkyl" refers to R b is a C1-C4 alkyl group as generally defined above, and R a is a C1-C4 alkylene group as generally defined above, b -OR a - refers to the group.

[0017] As used herein, the term "C1-C4 alkylcarbonyl" refers to R a is a C1-C4 alkyl group as generally defined above; a Refers to the group.

[0018] As used herein, the term "C1-C4 alkoxycarbonyl" refers to R a is a C1-C4 alkyl group as generally defined above, a Refers to the group.

[0019] As used herein, "NC 1-4 The term "alkylamino" refers to a group of the formula -NH-R a (wherein R a is the C defined above. 1-4 It refers to an alkyl group.

[0020] As used herein, "N,N-diC 1-4 The term "alkylamino" refers to a group of the formula -N(R a )Ra (wherein each R a is the C defined above. 1-4 alkyl groups, which may be the same or different.

[0021] As used herein, the term "C1-C4 alkylaminocarbonyl" refers to R a is a C1-C4 alkyl group as generally defined above, a Refers to the group.

[0022] As used herein, the term "di(C1-C4 alkylamino)carbonyl" refers to each R a are C1-C4 alkyl groups, which may be identical or different, as generally defined above; a (R a ) group.

[0023] As used herein, the term "C2-C4 alkenyloxy" refers to R a is a C2-C4 alkenyl group as generally defined above; a Refers to the group.

[0024] As used herein, the term "C2-C4 alkynyloxy" refers to R a is a C2-C4 alkynyl group as generally defined above; a Refers to the group.

[0025] As used in this specification, "C1-C n -alkylthio" or "C1-C n The term "-alkylsulfanyl" refers to a C1-C alkyl group linked through a sulfur atom. n -refers to an alkyl group.

[0026] As used in this specification, "C1-C nThe term "-alkylsulfinyl" refers to a C1-C alkyl group linked through the sulfur atom of the sulfinyl (or S(=O)-) group. n Refers to an alkyl group.

[0027] As used in this specification, "C1-C n The term "-alkylsulfonyl" refers to a C1-C alkyl group linked through the sulfur atom of the sulfonyl (or S(=O)2-) group. n Refers to an alkyl group.

[0028] As used herein, the term "N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl" refers to R a is a C1-C4 alkyl group as generally defined above, and R b is a C1-C4 alkyl group as generally defined above, a )=NO(R b ) group.

[0029] As used herein, the term "N-hydroxy-C-C1-C4 alkyl-carbonimidoyl" refers to R a is a C1-C4 alkyl group as generally defined above a )=NOH group.

[0030] As used herein, the term "C3-C6 cycloalkyl" refers to a stable monocyclic ring group containing 3-6 carbon atoms, either saturated or partially unsaturated. The terms "C3-C4 cycloalkyl" and "C3-C5 cycloalkyl" should be interpreted accordingly. Examples of C3-C6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopenten-1-yl, cyclopenten-3-yl, and cyclohexen-3-yl.

[0031] As used herein, “C3-C6 cycloalkyl C 1-The term "C4 alkyl" refers to a C3-C6 cycloalkyl ring as defined above that is bonded to the remainder of the molecule by a C1-C4 alkylene group as defined above. 1- Examples of C4 alkyl include, but are not limited to, cyclopropyl-methyl, cyclobutyl-ethyl, and cyclopentyl-methyl.

[0032] Examples of 5- or 6-membered heteroaryl rings containing 1 to 4 heteroatoms independently selected from nitrogen, oxygen and sulfur include, but are not limited to, pyridyl, pyrimidyl, pyrrolyl, pyrazolyl, furyl, thienyl, imidazolyl, isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyrazinyl, pyridazinyl and triazinyl.

[0033] The compounds of formula (I) or intermediate compounds of formula (III) according to the invention having at least one basic centre can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, phosphoric acid or hydrohalic acids, with strong organic carboxylic acids, such as C1-C4 alkane carboxylic acids, which are unsubstituted or substituted, for example by halogen, for example acetic acid, with saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, with hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or with strong organic sulfonic acids, such as C1-C4 alkane- or arylsulfonic acids, which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid.

[0034] The compounds of formula (I) or intermediate compounds of formula (III) according to the invention having at least one acidic group can form salts with bases, for example inorganic salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or can form salts with ammonia or organic amines, such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower-alkylamines, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower-alkylamines, for example mono-, di- or triethanolamine.

[0035] The possible presence of one or more asymmetric carbon atoms in the compounds of formula (I) according to the invention means that the compounds can occur in chiral isomeric forms, i.e. enantiomeric or diastereomeric forms. Atropisomers can also occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all of these possible isomeric forms and mixtures thereof. The invention includes all of these possible isomeric forms and mixtures thereof of the compounds of formula (I) according to the invention. Similarly, the compounds of formula (I) are intended to include all possible tautomers, if any, including lactam-lactim tautomers and keto-enol tautomers. The invention includes all possible tautomeric forms of the compounds of formula (I) according to the invention.

[0036] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides, in covalently hydrated form or in salt form, for example in agriculturally usable or agrochemically acceptable salt form. N-oxides are the oxidized forms of tertiary amines or of nitrogen-containing aromatic heterocyclic compounds. These are described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton 1991. N-oxides can be prepared by reacting the compounds of formula (I) with a suitable oxidizing agent, for example H2O2 / urea adduct, in the presence of an acid anhydride, for example trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 1989, 32(12), 2561-73 or from WO 2000 / 15615. The compounds of formula (I) according to the invention also include hydrates that may be formed during the salt formation.

[0037] The following list refers to the compounds of formula (I) of the present invention and is intended to illustrate the substituent 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 1 , Q 2 , Q 3 , and Z 1 For any one of these substituents, any of the definitions set forth below may be combined with any of the definitions of any other substituents set forth below or elsewhere in this document.

[0038] In one embodiment of the present invention, R 1 is C1-C4 alkyl. Preferably, R 1 is methyl, ethyl or isopropyl. More preferably, R 1is methyl.

[0039] In an embodiment of the present invention, R 2 is selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl and N-hydroxy-C-C1-C4 alkyl-carbonimidoyl. 2 is selected from the group consisting of hydrogen, halogen, methyl, ethyl, cyclopropyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl and N-hydroxy-C-C1-C2 alkyl-carbonimidoyl. More preferably, R 2 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, cyclopropyl, acetyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3 and -C(CH3)=NOH. Even more preferably, R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

[0040] In one embodiment of the present invention, R 3 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl. More preferably, R 3 is hydrogen.

[0041] In one embodiment of the present invention, R 4 is selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, cyano and C1-C4 alkoxycarbonyl. 4 is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, ethyl, isopropyl, cyano and -COMe. More preferably, R 4 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl and cyano. Even more preferably, R 4 is hydrogen or methyl.

[0042] In one embodiment of the present invention, R 5 and R6 is independently selected from the group consisting of hydrogen, methyl and ethyl. 5 and R 6 is independently selected from the group consisting of hydrogen and methyl. More preferably, R 5 and R 6 is hydrogen.

[0043] In one embodiment of the present invention, A 1 , A 2 and A 3 CR 7 , N, O, and S, with the proviso that A 1 , A 2 and A 3 At least one of is selected from N, O and S, and A 1 , A 2 and A 3 Exactly one of is O or S.

[0044] In one embodiment of the present invention, R 7 is hydrogen or methyl.

[0045] In one embodiment of the present invention, R 8 is hydrogen or methyl.

[0046] In one embodiment of the present invention, Q 1 , Q 2 and Q 3 CR 9 , N, N.R. 10 and S, with the proviso that Q 1 , Q 2 and Q 3 At least one of is N, NR 10 and S, and Q 1 , Q 2 and Q 3 Only one of them is NR 10 Or S.

[0047] In one embodiment of the present invention, R 9is selected from the group consisting of hydrogen, halogen, cyano and C1-C4 alkyl. 9 is selected from the group consisting of hydrogen, chlorine, bromine, cyano and methyl. More preferably, R 9 is hydrogen or chlorine.

[0048] In one embodiment of the present invention, R 10 is hydrogen or C1-C4 alkyl. 10 is hydrogen or methyl.

[0049] In one embodiment of the present invention, Z 1 is selected from the group consisting of 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methylsulfonyl-phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-furyl, 2-thienyl, 3-thienyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-methoxyphenyl, 4-ethynyl-2-fluoro-phenyl, 4-fluoro-2-methoxy-phenyl, cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl, n-propyl and phenyl. Preferably, Z 1 is selected from the group consisting of 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-methylphenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, 4-methylphenyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl and phenyl. More preferably, Z 1is selected from the group consisting of 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, cyclobutyl, cyclohexyl, cyclopentyl and methyl. Even more preferably, Z 1 is selected from the group consisting of 2,4-difluorophenyl, 2-fluorophenyl, 4-fluorophenyl, and phenyl.

[0050] In another embodiment, Z 1 are 1-methylpyrazol-4-yl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3-fluoro-2-pyridyl, 2-fluoro-4-methoxy-phenyl, 2-fluoro-4-methylsulfonyl-phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3,5-difluoro-2-furyl, 3- Fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-methoxyphenyl, 4-ethynyl-2-fluoro-phenyl, 4-fluoro-2-methoxy-phenyl, cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl, n-propyl or phenyl. More preferably, Z 1is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 3,5-difluoro-2-pyridyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-methylphenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, 4-methylphenyl, cyclobutyl, cyclohexyl, cyclopentyl, methyl or phenyl. Even more preferably, Z 1 is selected from 1-methylpyrazol-4-yl, 2,4,6-trifluorophenyl, 3,5-difluoro-2-pyridyl, 2,4-difluorophenyl, 2-fluorophenyl, 2-furyl, 2-methylphenyl, 2-thienyl, 3,4-difluorophenyl, 3-chlorophenyl, 3-thienyl, 4-fluoro-2-methoxy-phenyl, 4-fluorophenyl, cyclobutyl, cyclohexyl, cyclopentyl or phenyl. Even more preferably, Z 1 is selected from the group consisting of methyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylphenyl, 2-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-fluoro-2-methoxy-phenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 3,5-difluoro-2-pyridyl, 2-furyl, 2-thienyl, 3-thienyl and 1-methylpyrazol-4-yl. Even more preferably still, Z 1 is selected from 2,4-difluorophenyl, 3,5-difluoro-2-pyridyl, 2-fluorophenyl, 4-fluorophenyl or phenyl.

[0051] In one embodiment of the invention, the compound of formula (I) is a compound of formula (II): [ka] (In the formula, R 1 , R 2 , R 3, R 4 , R 5 , R 6 , and Z 1 is as defined for the compounds of formula (I) according to the invention, A is A-1 to A-36: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7a , R 7b , R 7c , R 8a , R 8b and R 8c is selected from the group consisting of: independently selected from the group consisting of hydrogen, C1-C4 alkyl, C2-C4 alkenyl, and C2-C4 alkynyl; and Q is Q-1 to Q-22: [ka] (In the formula, R 9a , R 9b and R 9c is independently selected from the group consisting of hydrogen, halogen, cyano, and C1-C4 alkyl; R 10a , R 10b and R 10c is independently selected from the group consisting of hydrogen or C1-C4 alkyl.

[0052] In one embodiment of the present invention, R 7a , R 7b , R 7c , R 8a , R 8b and R 8c is independently hydrogen or methyl.

[0053] In another embodiment of the present invention, R 7a , R 7b , R 7c , R8a , R 8b and R 8c is hydrogen.

[0054] In another embodiment of the present invention, R 7a , R 7b , R 7c , R 8a , R 8b and R 8c is methyl.

[0055] Preferably, in the compound of formula (II), R 7a , R 7b and R 7c is hydrogen, and R 8a , R 8b and R 8c Each of is methyl.

[0056] In one embodiment of the present invention, in the compound of formula (II), A is selected from A-1, A-4, A-6, A-7, A-9, A-10, A-13 and A-15: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7a , R 7b and R 7c are independently hydrogen or methyl. is selected from the group consisting of:

[0057] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-1, A-4, A-6, A-7, A-9, A-10, A-13 and A-15: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7a , R 7b and R 7c is hydrogen) is selected from the group consisting of:

[0058] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-1, A-4, A-9, A-10, A-13 and A-15: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7a , R 7b and R 7c is hydrogen.

[0059] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-1, A-4, A-9 and A-10: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7c is hydrogen) is selected from the group consisting of:

[0060] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-4, A-6, A-7, A-9 and A-10: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7c is hydrogen) is selected from the group consisting of:

[0061] Preferably, in the compound of formula (II), A is selected from the group consisting of A-4, A-6, A-7, A-9 and A-10, and R 7c is hydrogen.

[0062] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-4, A-9 and A-10: [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 (representing a bond to a group).

[0063] Preferably, in the compound of formula (II), A is selected from the group consisting of A-4, A-9 and A-10, and R 7c is hydrogen.

[0064] In another embodiment of the present invention, in the compound of formula (II), A is selected from A-4, A-7 and A-9. [ka] (In the formula, [ka] indicates a bond to a C(=O) group, and the arrow indicates Z 1 indicates a bond to the group, and R 7c is hydrogen.

[0065] More preferably, in the compound of formula (II), A is selected from the group consisting of A-4, A-7 and A-9, and R 7c is hydrogen.

[0066] More preferably, in the compound of formula (II), A is A-9 and R 7c is hydrogen.

[0067] In one embodiment of the present invention, R 9a , R 9b and R 9c is independently selected from the group consisting of hydrogen, chlorine, bromine, cyano, and methyl; and R 10a , R 10b and R 10c is independently hydrogen or methyl.

[0068] In another embodiment of the present invention, R 9a , R 9b and R 9c are independently hydrogen or chlorine, and R 10a , R 10b and R 10c is methyl.

[0069] In one embodiment of the present invention, in the compound of formula (II), Q is selected from Q-1, Q-2, Q-3, Q-7, Q-8, Q-9, Q-10, Q-11 and Q-12: [ka] (In the formula, R 9a , R 9b and R 9c are independently hydrogen or chlorine, and R 10a , R 10b and R 10c is methyl.

[0070] Preferably, in the compound of formula (II), Q is selected from Q-1, Q-2, Q-3, Q-7, Q-8 and Q-9: [ka] (In the formula, R 9a , R 9b and R 9c are independently hydrogen or chlorine, and R 10a , R 10b and R 10c is methyl.

[0071] In one embodiment of the present invention, the compound of formula (II) is a compound of formula (II-A) where A is A-4: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q and Z 1 is as defined for the compound of formula (II) according to the present invention. It could be.

[0072] In a variation of this embodiment of the invention, the compound of formula (II) may be a compound of formula (II-A), wherein Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-7, Q-8, Q-9, Q-10, Q-11 and Q12.

[0073] Preferably, in the compound of formula (II-A) of the present invention, R 1 is C1-C4 alkyl, preferably methyl, ethyl or isopropyl; R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 3 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 4 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, and cyano; R 5 and R 6 is independently selected from the group consisting of hydrogen, methyl and ethyl; and Q and Z1 is as defined for the compound of formula (II) according to the present invention.

[0074] In another embodiment of the present invention, the compound of formula (II) is a compound of formula (II-B) where A is A-9: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7c , Q and Z 1 is as defined for the compound of formula (II) according to the present invention. It could be.

[0075] In a variation of this embodiment of the invention, the compound of formula (II) may be a compound of formula (II-B), wherein Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-7, Q-8, Q-9, Q-10, Q-11 and Q12.

[0076] Preferably, in the compound of formula (II-B) of the present invention, R 1 is C1-C4 alkyl, preferably methyl, ethyl or isopropyl; R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 3 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 4 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, and cyano; R 5 and R 6 is independently selected from the group consisting of hydrogen, methyl and ethyl; R 7c is hydrogen or methyl, and Q and Z 1 is as defined for the compound of formula (II) according to the present invention.

[0077] In another embodiment of the present invention, the compound of formula (II) is A-10, a compound of formula (II-C): [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7c , Q and Z 1 is as defined for the compound of formula (II) according to the present invention. It could be.

[0078] In a variation of this embodiment of the invention, the compound of formula (II) may be a compound of formula (II-C), wherein Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-7, Q-8, Q-9, Q-10, Q-11 and Q-12.

[0079] Preferably, in the compound of formula (II-C) of the present invention, R 1 is C1-C4 alkyl, preferably methyl, ethyl or isopropyl; R 2 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 3 is selected from the group consisting of hydrogen, fluorine, chlorine and methyl; R 4 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, and cyano; R 5 and R 6 is independently selected from the group consisting of hydrogen, methyl and ethyl; R 7c is hydrogen or methyl, and Q and Z 1 is as defined for the compound of formula (II) according to the present invention.

[0080] The presence of one or more possible asymmetric carbon atoms in any of the compounds of formula (I), (II), (II-A), (II-B) and (II-C) according to the present invention means that such compounds may occur in chiral isomeric forms, i.e. in enantiomeric or diastereomeric forms.

[0081] Preferably, the compound of formula (I) according to the present invention is selected from the compounds listed in any one of Tables A-1 to A-78 or the compounds P-1 to P-11 listed in Table T1.

[0082] More preferably, the compounds of formula (I) according to the present invention are selected from compounds P-1 to P-11 listed in Table T1.

[0083] According to a fifth aspect of the present invention, there is provided an intermediate compound of formula (III) or a salt thereof: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q 1 , Q 2 and Q 3 corresponds to the same definition as for the compounds of formula (II) according to the present invention) is provided.

[0084] The intermediate compound of formula (III) is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q 1 , Q 2 and Q 3 have the same definitions and corresponding preferences as in the compounds of formula (II) according to the present invention.

[0085] The presence of one or more possible asymmetric carbon atoms in the compounds of formula (III) according to the invention means that such compounds can occur in chiral isomeric forms, ie in enantiomeric or diastereomeric forms.

[0086] Compounds of formula (I) according to the present invention can be formed as shown in Schemes 1-10 below, where, unless otherwise specified, the definition of each variable is as defined above for compounds of formula (I).

[0087] In any of the following schemes 1 to 10, the possible presence of one or more asymmetric carbon atoms in the compound of formula (I) according to the present invention means that this compound can occur in chiral isomeric forms, i.e. in enantiomeric or diastereomeric forms.

[0088] Compounds defined in any of the embodiments of the present invention can be formed as shown in Schemes 1-10 below, where, unless otherwise specified, the definition of each variable is as defined above in any embodiment of the present invention.

[0089] Compounds of formula (I) may be prepared from compounds of formula (III) by reaction with compounds of formula (II) using dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC) or N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDAC·HCl) together with additives such as 1-hydroxybenzotriazole (HOBt), hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine (HODhbt), N-hydroxysuccinimide (HOSu), 1-hydroxy-7-aza-1H-benzotriazole (HOAt) or 4-(N,N-dimethylamino)pyridine (DMAP). This reaction is shown in Scheme 1. [ka] Scheme 1

[0090] Alternatively, compounds of formula (I) may be prepared by reacting compounds of formula (IIa) with compounds of formula (III) in an inert solvent such as tetrahydrofuran (THF), ethyl acetate, methylene chloride, toluene, and the like, optionally in the presence of an inorganic base, for example aqueous sodium hydroxide or potassium carbonate, or in the presence of an organic base, such as trimethylamine or diisopropylamine. The latter reaction with an organic base may be carried out, optionally, in the presence of a catalyst, such as DMAP. 0 Compounds of formula (IIa), where is a halogen, preferably chlorine, can be prepared from compounds of formula (II) by treatment with a halogenating agent, such as thionyl chloride (SOCl2) or oxalyl chloride (COCl2), in an inert solvent as described above, optionally mediated by the presence of a catalytic amount of N,N-dimethylformamide. This reaction is shown in Scheme 2. [ka] Scheme 2

[0091] The acylation reaction of carboxylic acids, such as compounds of formula (II), with amines, such as compounds of formula (III), is well known to those skilled in the art and is described, for example, in Eur. J. Org. Chem. 2020, 4641-4651, and references cited therein.

[0092] Compounds of formula (II) are commercially available or can be prepared according to or analogously to procedures described in the literature, for example WO 2018 / 019929, Org. Proc. Res. Dev. 2020, 24(2), 228-234, WO 2018 / 019929, Lett. Org. Chem. 2010, 7(7), 502-507, and J. Het Chem. 2015, 52(6), 1823-1833.

[0093] A compound of formula (III) or a salt thereof (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6, Q 1 , Q 2 and Q 3 is as defined above for compounds of formula (I), can be reacted with a nitrile of formula (IV), where R 1 , R 2 , R 3 , R 4 , Q 1 , Q 2 and Q 3 can be prepared by one skilled in the art by reaction of R (as defined above for compounds of formula (I)) with a suitable nucleophile such as (dimethylsulfide)dihydroboron (BMS). The reduction can also be achieved with, for example, sodium borohydride in the presence of a catalyst such as cobalt(II) chloride in an aprotic solvent (see Preparations for further details). Alternatively, the Grignard reagent R 5 MgBr or R 6 MgBr (wherein, R 5 and R 6 As defined above for compounds of formula (I), Ti(O-) can be added sequentially or simultaneously as a nucleophile to compounds of formula (IV) to allow the preparation of more highly substituted amines of formula (III). Such Grignard additions to nitriles can be carried out in inert solvents such as diethyl ether, tert-butyl methyl ether and cyclopentyl methyl ether using Ti(O-) as a nucleophile. i The reaction is carried out in the presence of a Lewis acid such as Pr)4 (see Synlett 2007, (4), 652-654). This reaction is shown in Scheme 3. [ka] Scheme 3

[0094] A compound of formula (IV) 1 , R 2 , R 3 , R 4 , Q 1 , Q 2 and Q3 (wherein R is as defined above for compounds of formula (I)) can be prepared by one skilled in the art according to known methods. More specifically, compounds of formula (IV) and intermediates thereto can be prepared from compounds of formula (V) as shown in Scheme 4. [ka] Scheme 4

[0095] For example, a compound of formula (IV) 1 , R 2 , R 3 , R 4 , Q 1 , Q 2 and Q 3 is as defined above for compounds of formula (I), and R 4 is different from hydrogen) can be prepared by the reaction of a compound of formula (IVa) (wherein R 4 is hydrogen, and R 1 , R 2 , R 3 , Q 1 , Q 2 and Q 3 is defined as above for compounds of formula (I), followed by the addition of a suitable alkylating agent R 4 -X 0 (In the formula, X 0 Compounds of formula (IVa) (wherein R is a halogen) can be prepared by one skilled in the art. 4 is hydrogen, and R 1 , R 2 , R 3 , Q 1 , Q 2 and Q 3(wherein is as defined above for compounds of formula (I)) may be prepared from alcohols of formula (V) by treatment with cyanotrimethylsilane (TMSCN) in the presence of a base such as lithium carbonate, in a non-polar solvent such as dichloromethane, at temperatures between 0° C. and the boiling point of the reaction mixture. Such transformations are well known in the literature under a variety of conditions, for example as described in Org. Lett. 2008, 10, 4570 and references therein. This reaction is shown in Scheme 4.

[0096] The compound of formula (V) can be prepared by reacting a compound of formula (VI) 1 , Q 2 and Q 3 can be prepared from (as defined above for compounds of formula (I)) as shown in Scheme 5. [ka] Scheme 5

[0097] As shown in Scheme 5, a compound of formula (VII), 1 , R 2 and R 3 is as defined above for compounds of formula (I), and X 01 Metallation of the aryl group (where M is bromo or iodo) with a suitable reagent, such as turboGrignard (isopropylmagnesium chloride-lithium chloride complex) or an alkyllithium such as n-butyllithium, gives the intermediate Grignard or alkyllithium reagent (where M is MgX 01 or lithium) is obtained. CX 01 Such metal insertion into the bond is well known to those skilled in the art and is generally carried out in an inert solvent such as an ether, for example tert-butyl methyl ether or tetrahydrofuran, at a temperature generally between −78° C. and room temperature. A solution of the metallated species (VIIa) is then reacted with a compound of formula (VI), where Q 1 , Q 2 and Q 3is as defined above for compounds of formula (I) to give compounds of formula (V). Similar reactions of this type are described, for example, in WO 2012 / 102297 and Bio. Med. Chem. Lett. 2017, 27(17), 4044-4050 (X 01 is Br, n-butyllithium) and Ang. Chem., Int. Ed. 2016, 55(17), 5332-5336, U.S. Patent Application Publication No. 2014 / 0349990, WO 2002 / 004424, WO 2021 / 009068 (X 01 is described in I, Turbo Grignard).

[0098] Compounds of formula (VI) and formula (VII) are either commercially available or readily prepared by methods known to those skilled in the art.

[0099] Further synthesis of compounds of formula (I) can be achieved by treating compounds of formula (VIII) with a base such as sodium hydride or n-butyllithium in an inert solvent such as tetrahydrofuran, followed by the formation of compounds of formula (IX), 4 is as described under formula (I), and X 02 is a leaving group such as a halogen, mesylate or tosylate) to give a compound of formula (X). This reaction is shown in Scheme 6. [ka] Scheme 6

[0100] Then, a compound of formula (X), 1 , R 2 , R 3 , and R 4 is as defined above for compounds of formula (I)) with a strong base such as sodium hydride or an alkyl lithium base such as n-butyllithium in an inert solvent such as tetrahydrofuran or tert-butyl methyl ether at a temperature between −78° C. and room temperature, followed by the formation of a compound of formula (XI)1 , Q 2 and Q 3 is as defined above for compounds of formula (I), and X 03 is a leaving group such as a halogen, preferably F, Cl or Br), is added to give compounds of formula (IV). This reaction is shown in Scheme 7. [ka] Scheme 7

[0101] Compounds of formula (IV) are converted to compounds of formula (I) as previously described in Schemes 1, 2 and 3. One skilled in the art will recognize that the conversion of compound (VIII) to compounds of formula (IV) may be carried out sequentially or in the same reaction vessel to provide a streamlined conversion of compounds of formula (VIII) to compounds of formula (IV), as described in further detail in the Preparation Examples.

[0102] A compound of formula (Ia) 1 , R 2 , R 3 , R 5 , Q 1 , Q 2 , Q 3 , A 1 , A 2 , A 3 and Z 1 is as described above for compounds of formula (I), and R 4 and R 6 is hydrogen) can also be prepared by reacting a compound of formula (VI) (wherein Q is hydrogen) in the presence of a base such as triethylamine, optionally in an inert solvent such as ethanol or methanol. 1 , Q 2 and Q 3 is as defined above for compounds of formula (I)) into a compound of formula (XII), 5can be prepared by treatment with an anhydride such as trifluoroacetic anhydride in an inert solvent such as methylene chloride in the presence of a base, for example triethylamine, to give compounds of formula (XIII). This reaction is shown in Scheme 8. [ka] Scheme 8

[0103] Those skilled in the art will appreciate that compounds of formula (VI) may be converted to compounds of formula (XIV) without isolating the intermediate of formula (XIII). Such a reaction, known as the Henry reaction, is well described in the literature, as evidenced by Tetrahedron 2001, 57(6), 915-945 and references cited therein. Compounds of formula (XIV) may be converted to compounds of formula (XV) by treatment with compounds of formula (VIIa) in an inert solvent such as tetrahydrofuran (see Scheme 5). This reaction is shown in Scheme 9. [ka] Scheme 9

[0104] Similar Michael additions of organometallics to nitroalkenes have been reported, for example, in Org. Lett., 2007, 9, 85-87. Reduction of the nitro group of a compound of formula (XV) to an amine to give a compound of formula (IIIa) can be achieved by a number of methods commonly known to those skilled in the art, such as Béchamp reduction or reduction with hydrogen in the presence of a metal catalyst. This reaction is shown in Scheme 10. [ka] Scheme 10

[0105] Compounds of formula (IIIa) are converted to compounds of formula (Ia) by the methods described in Schemes 1 and 2.

[0106] A compound of formula (I) as defined in any of the embodiments of the present invention can be converted in a manner known per se into another compound as defined in any of the embodiments of the present invention by replacing one or more of the substituents of the starting compound with one or more other substituents according to the present invention in a conventional manner.Those skilled in the art will also understand that a compound of formula (I) can be further transformed into further derivatives of formula (I), for example, by alkylation, nucleophilic substitution, elimination, CC bond forming reaction in the presence of a metal catalyst, heteroatom-carbon bond forming in the presence of a metal catalyst, oxidation, and reduction.

[0107] Depending on the reaction conditions and the choice of starting materials suitable in each case, it may, for example, only be possible in one reaction step to replace one substituent with another substituent according to the invention, or several substituents may be replaced with other substituents according to the invention in the same reaction step.

[0108] Salts of compounds of formula (I) can be prepared in a manner known per se: thus, for example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0109] The salts of the compounds of formula (I) can be converted in customary manner, for example into the free compounds I (acid addition salts) by treatment with a suitable basic compound or a suitable ion exchange reagent, and can also be converted into salts with bases, for example by treatment with a suitable acid or a suitable ion exchange reagent.

[0110] Salts of compounds of formula (I) can be converted into other salts (acid addition salts, e.g. other acid addition salts) of compounds of formula (I) in a manner known per se, for example by treating the salt of an inorganic acid, such as hydrochloric acid, with a suitable metal salt of the acid, such as a sodium, barium or silver salt (e.g. silver acetate), in a suitable solvent (in which inorganic salts forming, for example, silver chloride, are insoluble and therefore precipitate from the reaction mixture).

[0111] Depending on the procedure or reaction conditions, compounds of formula (I) having salt-forming properties may be available in the free form or in salt form.

[0112] The compounds of formula (I) and, where appropriate, their tautomers, in each free or salt form, can exist in the form of pure isomers, such as, for example, enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or depending on the configuration of non-aromatic double bonds occurring in the molecule; the invention relates to the pure isomers and also to all possible isomeric mixtures, and is to be understood in this sense above and below, respectively, even if details of the stereochemistry are not specifically stated in each case.

[0113] The compounds of formula (I) of the present invention exhibit two asymmetric carbon atoms. The relationship between the enantiomers and diastereomers of the compounds of formula (I) is shown below. [ka]

[0114] Those skilled in the art will recognize that diastereomers and enantiomers of formula (I) above (wherein 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 1 , Q 2 , Q 3 and Z 1is as defined for formula (I)) is well known within the scope of the present invention.

[0115] Diastereomeric or racemic mixtures of compounds of formula I, in free or salt form, obtained depending on which starting materials and procedures are selected, may be separated in known manner into the pure diastereomers or racemates on the basis of the physical chemical differences of the components, for example by fractional crystallization, distillation and / or chromatography.

[0116] Enantiomeric mixtures, such as racemates, which can be obtained in a similar manner can be resolved into their optical antipodes by known methods, for example by recrystallization from an optically active solvent; by chromatography on chiral adsorbents, for example by high performance liquid chromatography (HPLC) on cellulose acetate using suitable microorganisms; by cleavage by specific immobilized enzymes, via the formation of inclusion compounds, for example with chiral crown ethers, in which only one enantiomer is complexed; or by conversion into diastereomeric salts, for example by reacting the basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixtures which can be obtained thereby, for example by fractional crystallization according to their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example a basic agent.

[0117] Pure diastereomers or enantiomers can be obtained according to the invention not only by separating the appropriate isomeric mixture but also by diastereoselective or enantioselective synthesis, which is generally known in the art, e.g. by carrying out the process according to the invention using starting materials with the appropriate stereochemistry.

[0118] If the individual components have different biological activity, it may be advantageous to isolate or synthesize, in each case, the more biologically effective isomer, e.g., enantiomer or diastereomer, or a mixture of isomers, e.g., a mixture of enantiomers or diastereomers.

[0119] As an example, compounds with two or more asymmetric carbon atoms may exist in diastereoisomeric forms that are optionally separable using, for example, supercritical fluid chromatography (SFC) chromatography with a chiral column. Such diastereomers may exhibit different fungicidal activity profiles, but all isomers and diastereomers form part of the present invention.

[0120] The compounds of formula (I) and, where appropriate, their tautomers may also be available in free or salt form, where appropriate, in the form of hydrates and / or include other solvents, such as those that may have been used for the crystallization of compounds present in solid form.

[0121] As stated above, it has now surprisingly been found that the compounds of formula (I) of the present invention have a highly advantageous level of biological activity for practical purposes in protecting plants against diseases caused by fungi.

[0122] The compounds of formula (I) according to the invention can be used in the agricultural sector and related fields of use, for example as active ingredients for controlling plant pests or non-living materials, for controlling spoilage microorganisms or organisms potentially harmful to humans. The novel compounds are distinguished by their excellent activity at low application rates, their excellent tolerance by plants, and their safety for the environment. They have highly useful curative, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of formula (I) can be used to inhibit or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time also protecting these parts of later-growing plants from, for example, phytopathogenic microorganisms.

[0123] The present invention further relates to a method for controlling or preventing infestation of susceptible plants or plant propagation material and / or harvested food crops by microorganisms by treating the plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound of formula (I) according to the invention is applied to the plant, its part or its habitat.

[0124] The compounds of formula (I) according to the present invention may also be used as fungicides. The term "fungicide" as used herein means a compound that controls, modifies or prevents the growth of fungi. The term "fungicidally effective amount" as used herein means the amount of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. A controlling or modifier effect includes any deviation from natural development such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent infection by fungi.

[0125] As used herein, the term "control" refers to reducing the number of pests, eradicating pests, and / or preventing further damage by pests, thereby reducing damage to plants or plant-derived products.

[0126] The term "prevent" when used in the context of infestation of plants or plant propagation material and / or harvested food crops refers to the avoidance of symptoms resulting from microbial attack or fungal infection (fungal growth).

[0127] It may also be possible to use the compounds of formula (I) according to the invention as dressings for treating plant propagation material, for example seeds such as fruits, tubers or grains or plant cuttings, for protection against fungal infections occurring in the soil as well as against phytopathogenic fungi. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: for example, seeds can be dressed before being sown. The active compounds of formula (I) can also be applied to grains (coating) by impregnating the seeds in a liquid formulation or coating the seeds with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example in the sowing furrow during sowing. The invention also relates to a method for treating such plant propagation material and to the plant propagation material thus treated.

[0128] Furthermore, the compounds of formula (I) according to the present invention can be used for controlling fungi in related fields such as the protection of industrial materials, including wood and wood-based industrial products, food storage and hygiene control.

[0129] In addition, the present invention can be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0130] The compounds of formula (I) according to the invention are effective against, for example, fungi and fungal vectors involved in diseases, as well as phytopathogenic bacteria and viruses, such as, for example: Alternaria spp., including Absidia corymbifera, Alternaria solani, Aphanomyces spp., Ascochyta spp., Aspergillus spp., including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, lactucae, Aureobasidium spp., including B. dothidea, B. obtusa, Botryosphaeria spp., including Botryotinia fuckeliana, Botrytis spp., including Botrytis cinerea, C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Candida spp., including Cephaloascus fragrans spp., Cercospora spp., including Ceratocystis spp., Cercospora arachidicola, Cercospora kikuchii, Cercospora sojina, and Cercosporidium personatum.), Cladosporium spp., including Cladosporium cucumerinum, Claviceps purpurea, and Coccidioides immitis, Cochliobolus spp., Colletotrichum spp., including Colletotrichum musae, Colletotrichum asianum, Corynespora cassiicola, and Cryptococcus neoformans, Diaporthe spp., Didymella spp., including Didymella bryoniae, spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora, Erysiphe spp. including Erysiphe cichoracearum, Eutypa lata, Fusarium culmorum, Fusarium graminearum, Fusarium langsethiae, Fusarium moniliforme, Fusarium oxysporum, Fusarium praliferatum, Fusarium Fusarium spp., including Fusarium proliferatum, Fusarium subglutinans, and Fusarium solani), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Glomerella lagenarium, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum spp., Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including Mycosphaerella graminicola, Mycosphaerella spp. including Mycosphaerella pomi, Oncobasidium theobromaeon theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp., P. maydis, P.maydis, Peronosclerospora spp. including P. philippinensis and P. sorghi, Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara halstegii, halstedii, Plasmopara spp. including Plasmopara viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp. including P. cubensis, P. humuli, Pseudoperonospora spp. including P. humuli, Puccinia spp., including Pseudopeziza tracheiphila, Puccinia hordei, Puccinia recondita, Puccinia striiformis, and Puccinia triticina.), Pyrenopeziza spp., Pyrenophora spp. including Pyrenophora teres, Pyricularia spp. including Pyricularia oryzae, Pythium spp. including P. ultimum, Ramularia spp., Rhizoctonia spp. including Rhizoctonia solani, Rhizomucor pusillus,. Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp., including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., including Sclerotinia sclerotiorum, Sclerotium spp., Septoria spp., including Septoria nodorum, Septoria tritici, Sphaerotheca macularis, macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp., Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride spp.), Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. including Venturia inaequalis, Verticillium spp.), as well as Xanthomonas spp.

[0131] The compounds of formula (I) according to the invention may be used, for example, on turf, ornamental plants such as flowers, shrubs, broadleaf or evergreen trees such as conifers, as well as for trunk injections, pest management and the like.

[0132] Within the scope of the present invention, the target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; and arable plants, such as bermuda grass, strawberry bush, bentgrass, centipede grass, fescue, ryegrass, lawn grass and wild grass. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines, for example grapes.

[0133] The term "useful plants" should also be understood to include useful plants in which resistance to herbicides such as bromoxynil or to a class of herbicides (e.g. HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc.) has been imparted by conventional breeding or genetic engineering methods. An example of a crop in which resistance to imidazolinones, e.g. imazamox, has been imparted by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered resistant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0134] The term "useful plants" should also be understood to include useful plants which have been transformed by recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as the known ones derived from toxin-producing bacteria, especially those belonging to the genus Bacillus.

[0135] Examples of such plants include YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Rootworm® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (cucumber beetle trait) and Protecta®.

[0136] The term "crop plant" should also be understood to include crop plants which have been transformed using recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those belonging to the genus Bacillus.

[0137] Toxins which can be expressed by such transformed plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as d-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from Photorhabdus spp. or Xenorhabdus spp., e.g. Photorhabdus luminescens, Xenorhabdus nematophilus, spp.); toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0138] Furthermore, in the context of the present invention, delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, are also to be understood as being particularly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by a new combination of different domains of these proteins (see, for example, WO 2002 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 2003 / 018810).

[0139] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 1993 / 07278, WO 1995 / 34656, EP 0 427 529, EP 0 451 878 and WO 2003 / 052073.

[0140] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 1995 / 34656, EP 0 367 474, EP 0 401 979 and WO 1990 / 13651.

[0141] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0142] Transgenic plants that contain one or more genes encoding insecticide resistance and expressing one or more toxins are known, some of which are commercially available. Examples of such plants include YieldGard® (a corn variety expressing a Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing a Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing a Cry9C toxin); Herculex I® (a corn variety expressing a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a Cry1Ac toxin); Bollgard I® (a cotton variety expressing a 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); Nature-Gard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0143] Further examples of such transformed crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.Sauveur, France. Genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0144] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.Sauveur, France. A genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of the Cry1Ab toxin. Bt176 maize also achieves tolerance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0145] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transformed maize plants is described in WO 2003 / 018810.

[0146] 4. MON863 maize, registration number C / DE / 02 / 9, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the Cry3Bb1 toxin and confers resistance to certain coleopteran insects.

[0147] 5. IPC531 Cotton made by Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0148] 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain lepidopteran insects, and for expression of the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0149] 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. It consists of a conventional hybrid maize variety by crossing the genetically engineered varieties NK603 and MON810. NK603 x MON810 maize transgenic expresses the protein CP4 EPSPS from the strain CP4 of Agrobacterium sp., which confers resistance to the herbicide Roundup® (containing glyphosate), and also transgenic expresses the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0150] The compounds of formula (I) according to the invention are useful in the prevention and control of phytopathogenic diseases, in particular phytopathogenic fungi, such as, for example, Alternaria solani, Blumeria graminis, Botryotinia fuckeliana, Botrytis cinerea, Cercospora arachidicola, Cercospora kikuchii, Cercospora sojina, Cladosporium cucumerinum, Colletotrichum lagenarium, Corynespora cassiicola, Didymella bryoniae, and the like. bryoniae, Fusarium spp., Glomerella lagenarium, Leptosphaeria spp., Leveillula taurica, Microdochium nivale, Plasmopara viticola, Puccinia recondita, Pyrenophora teres, Pyricularia oryzae, Rhizoctonia solani, Sclerotinia sclerotiorum, Septoria nodorum, Septoria tritici tritici, Sphaerotheca fuliginea, Uncinula necator and Venturia inaequalis.In one embodiment of the invention, the compounds of formula (I) according to the invention are useful for the prevention and control of phytopathogenic diseases, in particular phytopathogenic fungi, such as Septoria tritici, Pyrenophora teres, Puccinia recondita and Blumeria graminis in cereals; Cercospora arachidicola and Sclerotinia sclerotiorum in field crops; Alternaria solani in fruits and vegetables, such as tomatoes and potatoes; Botrytis cinerea in fruits, vegetables and field crops, such as strawberry, tomato, sunflower, legumes and grapes; Glomerella lagenarium in vegetables, such as cucumber. lagenarium; Uncinula necator in vegetables, e.g. grapes; Venturia inaequalis in fruits, e.g. apples; Rhizoctonia solani in vegetables, e.g. potatoes; Cladosporium cucumerinum, Didymella bryoniae and Sphaerotheca fuliginea in vegetables, e.g. cucumber; Leveillula taurica in cucumber and solanaceous vegetables; Fusarium spp. in cereals and vegetables; Leptosphaeria spp. in cereals.

[0151] As used herein, the term "locus" means the field in which a plant is growing or in which the seeds of a cultivated plant have been sown or in which the seeds will be sown in the soil. It includes the soil, the seeds and seedlings, as well as the established vegetation.

[0152] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage and fruits.

[0153] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, which can be used for their propagation, and vegetative bodies, such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts may be mentioned. Also mentioned are sprouted plants and shoots that are to be transplanted after germination or emergence from the soil. These shoots may be protected by a complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0154] The compounds of formula (I) according to the invention can be used in their pure form or, preferably, together with auxiliaries that are conveniently employed in the field of formulation.For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and capsules, for example, in polymeric materials.As well as the type of composition, the application method, such as spraying, misting, dusting, scattering, coating, or pouring, is selected according to the intended purpose and the current situation.The composition may also contain further auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders or adhesives, as well as fertilizers, sources of trace elements, or other compounds for obtaining special effects.

[0155] Suitable carriers and adjuvants, for example for use in agriculture, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0156] Suspension concentrates are aqueous formulations in which fine solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents and may further contain wetting agents to enhance activity, as well as anti-foaming agents and crystal growth inhibitors. In use, these concentrates are diluted in water and usually applied by spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0157] Wettable powders are in the form of fine particles that disperse easily in water or other liquid carriers. These particles contain the active ingredient held in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica and other easily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersing agents or emulsifying agents.

[0158] Emulsifiable concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, high boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and usually applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0159] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area where treatment is required. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, ground corn cobs, ground peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations usually contain 5% to 25% active ingredient, which may include surfactants such as high-boiling aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or spreading agents such as dextrin, glue or synthetic resins.

[0160] Dusts are free-flowing admixtures of the active ingredient and finely divided solids such as talc, clays, powders and other organic and inorganic solids which act as dispersants and carriers.

[0161] Microcapsules are typically droplets or granules of active ingredient enclosed in an inert porous shell that allows the encapsulated material to be released into the environment at a controlled rate. The encapsulated droplets are typically 1-50 microns in diameter. The encapsulated liquid typically constitutes 50-95% of the capsule's weight and may contain a solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule and retains the active species in liquid form within the pores of the granule. The granules are typically in the range of 1 millimeter to 1 centimeter in diameter, preferably 1-2 millimeters. Granules are formed by extrusion, agglomeration or prilling, or are natural. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0162] Other useful formulations for agricultural chemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalenes, xylenes and other organic solvents in which complete dissolution at the desired concentration is achieved. Pressurized sprayers may also be used in which the active ingredient is dispersed in finely divided form as the low boiling dispersant solvent carrier evaporates.

[0163] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0164] Liquid carriers that may be utilized include, for example, water, toluene, xylene, petroleum naphtha oil, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, kutadeca Examples of suitable solvents include ethyl acetate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. For dilution of concentrates, water is the typical carrier of choice.

[0165] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, Kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut hulls, and lignin.

[0166] A wide range of surfactants may be advantageously utilized in both the liquid and solid compositions, particularly those designed to be diluted with a carrier prior to application. These surfactants, when used, typically comprise from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic or polymeric in nature and may be utilized as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzene sulfonate; alkylphenol-alkylene oxide adducts such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryl trimethyl ammonium 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 phosphate esters.

[0167] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray size regulators, pigments, antioxidants, foaming agents, defoamers, light blocking agents, compatibilizers, antifoaming agents, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, trace elements, emollients, lubricants and adhesives.

[0168] In addition, other biocidal active ingredients or compositions may be combined with the compositions of the present invention, 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 together with the compositions of the present invention or may be mixed together, for example, in a spray tank. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0169] Pesticides are referred to herein using their common names as known, for example from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0170] In addition, the compositions of the present invention may also be applied together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0171] The compounds of formula (I) according to the present invention are usually used in the form of agrochemical compositions and can be applied to the crop areas or plants to be treated simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired with further carriers, surfactants or application-promoting adjuvants customarily used in the field of formulations.

[0172] The compounds of formula (I) according to the present specification may be used in the form of a (fungicidal) composition for the control or protection against phytopathogenic microorganisms, comprising at least one compound of formula (I) as active ingredient, or in the form of at least one preferred individual compound as defined herein, in free form or in the form of an agrochemically usable salt, and at least one of the abovementioned auxiliaries.

[0173] The present invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) according to the present invention, an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise, in addition to the compound of formula (I), at least one or more pesticidal active compounds, for example an additional fungicidal or fungicidal active ingredient.

[0174] The compounds of formula (I) according to the present invention may be the sole active ingredient in the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic activity.

[0175] Examples of suitable additional active ingredients are the following: acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, Morpholine fungicides and fungicides, organophosphate fungicides and fungicides, organotin fungicides and fungicides, oxathiin fungicides and fungicides, oxazole fungicides and fungicides, phenylsulfamide fungicides and fungicides, polysulfide fungicides and fungicides, pyrazole fungicides and fungicides, pyridine fungicides and fungicides, pyrimidine fungicides and fungicides, pyrrole fungicides and fungicides, quaternary ammonium fungicides and fungicides, quinoline fungicides and fungicides, quinone fungicides and fungicides, quinoxaline fungicides These include fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0176] Examples of suitable additional active ingredients include the following: petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenous oxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixa. Fen, Brofenvalerate, Bromocyclen, Bromophos, Bromopropylate, Buprofezin, Butocarboxim, Butoxycarboxim, Butylpyridaben, Calcium polysulfide, Camfechlor, Carbanolate, Carbophenothione, Cymiazole, Quinomethionate, Chlorbeneside, Chlordimeform, Chlordimeform hydrochloride, Chlorphenetole, Chlorfenson, Chlorphenesulfide, Chlorobenzilate, Chlormebuform, Chlormethuron, Chloropropylate, Chlorbeneside ... Lorthiofos, cinerin I, cinerin II, cinerins, closantel, coumaphos, crotamiton, crotoxyphos, khuraneb, cyanthoate, DCPM, DDT, demefion, demefion-O, demefion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulfone, dichlofluanid, dichlorvos, dicliphos, dienochlor, dimefox, ginex, ginex-diclexin, Dinocap-4, Dinocap-6, Dinoctone, Dinopentone, Dinosulfone, Dinotervone, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dofenapine, Doramectin, Endothion, Eprinomectin, Ethoate-methyl, Etrimphos, Fenazaflor, Fenbutatin oxide, Fenothiocarb, Fenpyrad, Fenpyroximate, Fenpyrazamine, Fenson, Fentrifanil, Flubenzimine, Flucycloxuron, Fluenethyl, Fluorobenside, FMC 1137, Formetanate, Formetanate hydrochloride, Formoparanate, γ-HCH, Gliodin, Halfenprox, Hexadecyl cyclopropanecarboxylate, Isocarbophos, Jasmolin I,Jasmolin II, Iodofenphos, Lindane, Malonoben, Mecarbam, Mesfolan, Mesulfen, Methacrifos, Methyl bromide, Metolcarb, Mexacarbate, Milbemycin oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Nifluridide, Nikkomycins, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, Omethoate, Oxydeprophos, Oxydi Sulfoton, pp'-DDT, parathion, permethrin, fencapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactins, proclonol, promacyl, propoxur, prothidathion, protoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quinthiophos, R-1492, phosglycine, rotenone, shradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfluramid, sulfotep, sulfur, diflovidazin, tau Fluvalinate, TEPP, Terbam, Tetradifon, Tetrasulf, Thiafenox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringiensin, Triamiphos, Triaratene, Triazophos, Triazuron, Trifenophos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Diclofen, Dichlorophen, Endothal, Fentin, Hydrated lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyl hydroxide Nilstin, crufomate, piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodysin, phenaminosulf, formaldehyde, hydragafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid,Oxytetracycline, hydroxyquinoline potassium sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliaeanisopliae, Neodiprionsertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp.), Typhlodromus occidentalis, Verticillium lecanii, Apholate, Visadil, Busulfan, Dimatif, Hemel, Hempa, Metepa, Methiotepa, Methyl Apholate, Molzide, Penfluron, Tepa, Thiohempa, Thiotepa, Tretamine, Uredepa, (E)-Deca-5-en-1-yl acetate and (E)-Deca-5-en-1-ol, (E)-Trideca-4-en-1-yl acetate, (E) -6-Methylhept-2-en-4-ol, (E,Z)-tetradec-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icos-13-en-10-one, (Z)-Tetradeca-7-en-1-al, (Z)-Tetradeca-9-en-1-ol, (Z)-Tetradeca-9-en-1-yl acetate, (7E,9Z)-Dodeca-7,9-dien-1-yl acetate, (9Z,11E)-Tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-Tetradeca-9,12-dien-1-yl acetate, 14-Methyloctadec-1-ene, 4-Methylnonan-5-ol and 4-Methylnonan-5-one, α-Murtistriatin, Brevicomin, Codrelure, Codremon, Curuleure, Disparuleure, Dodec-8-en-1-yl acetate, Dodec-9-en-1-yl acetate, Dodec-8,10-dien-1-yl acetate, Dominicalure, Ethyl 4-Methyloctanoate. Eugenol, Frontalin, Grandolure, Grandolure I, Grandolure II, Grandolure III, Grandolure IV, Hexalure, Ipsdienol, Ipsenol, Japonilure, Lineatin, Litulure, Loupulure, Medulure, Megatomoic Acid, Methyleugenol, Muscalure, Octadeca-2,13-dien-1-yl Acetate, Octadeca-3,13-dien-1-yl Acetate, Olfular, Orictalure, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl Acetate, Trimedulure, Trimedulure A, Trimedulure ... Medulure B1, Trimedulure B2, Trimedulure C, Trunkol, 2-(octylthio)ethanol, Butopyroneoxyl, Butoxy(polypropylene glycol), Dibutyl adipate, Dibutyl phthalate, Dibutyl succinate, Diethyltoluamide, Dimethylcarbamate, Dimethyl phthalate, Ethyl hexanediol, Hexamide, Methoxybutyl, Methylneodecanamide, Oxamate, Picaridin, 1-Dichloro-1-nitroethane, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-Dichloropropane and 1,3-Dichloropropane chloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovaleryl in Dan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, alixicarb, α-ecdysone, aluminum phosphide, aminocarb,Anabasine, Atidathion, Azamethiphos, Bacillus thuringiensis delta endotoxins, Barium hexafluorosilicate, Barium polysulfide, Bartholin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebazine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, kumitoate, cryolite, CS 708, cyanofenphos, cyanophos, ciclethrin, cithioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethryn, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetilan, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikincarb, IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kereban, kinoprene, lead arsenate, leptophos, lilimphos, ritidathion,m-Cumenyl methyl carbamate, magnesium phosphide, magidox, mecarfone, menazone, mercurous chloride, mesulfenphos, metam, metam potassium, metam sodium, methanesulfonyl fluoride, methoclotophos, methoprene, methotrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, mirex, Naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, paradichlorobenzene, parathion methyl, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, Phenkapton, Phosnichlor, Phosphine, Phoximmethyl, Pyrimetaphos, Polychlorodicyclopentadiene Isomers, Potassium Arsenite, Potassium Thiocyanate, Precocene I, Precocene II, Precocene III, Primidophos, Profluthrin, Promecarb, Prothiophos, Pyrazophos, Pyresmethrin, Cassia, Quinalphos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Kadethrin, Riania, Ryanodine, Sabadila, Shradan, Cebufos, SI-0009, Thiapronil, Sodium Arsenite, Sodium Cyanide, Sodium Fluoride, Sodium Hexafluorosilicate, Sodium Pentachlorophenoxide, Sodium Selenite, Sodium Thiocyanate, Sulcofuron, Sulcofuron Sodium, Sulfuryl Fluoride, Sulprofos, Tar Oil, tazimcarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclophos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap sodium, tralomethrin, transpermethrin, triazamate, trichloromethaphos-3, trichloronate, trimethacarb, tolprocarb, triclopyricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprophos, meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene-1,1-Dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, anicifluprine, benclothiaz, cytokinins, DCIP, furfural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria knotweed sachalinensis) extract, α-chlorohydrin, anthurium, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciriloside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonate, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, berubutin, MGK 264, piperonyl butoxide, piperotal, propyl isomers, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chloroinconazide, mercuric oxide, thiophanate methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazo , fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflurazole Mizole, Triticonazole, Ancymidol, Fenarimol, Nuarimol, Bupirimate, Dimethirimol, Ethyrimol, Dodemorph, Fenpropidin, Fenpropimorph, Spiroxamine, Tridemorph, Cyprodinil, Mepanipyrim, Pyrimethanil, Fenpiclonil, Fludioxonil, Benalaxyl, Furalaxyl, Metalaxyl, R-Metalaxyl, Ofurace, Oxadixyl, Carbendazim, Debacarb, Fuberidazole, Thiabendazole, Chlorhexidine, Lozolinate, Diclozolin, Mycrozolin, Procymidone, Vinclozolin, Boscalid, Carboxin, Fenfuram, Flutolanil, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide, Dodine, Iminoctadine, Azoxystrobin, Dimoxystrobin, Enestrobulin, Phenaminestrobin, Flufenoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Trifloxystrobin, Orysastrobin,, Picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, probineb, zineb, captafol, captan, fluorimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine copper, nitrotar isopropyl, edifenphos, iprobenfos, phosdifen, tolclofos methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, dicloci Met, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, fosetylaluminum, hymexazole, iprovalicarb, cyazofamid, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxins, propamocarb, pyribencarb, Proquinazide, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, fluveneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isotianil, dipimethitron, 6-ethyl-5,7-dioxo-pyrrolo[4 ,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-Dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), lvbenmixianan, diclobenthiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2 -Fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate tert-butyl, pyraziflumide, inpirfluxam, tolprocarb, mefentrifluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl] N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro- phenyl]methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate but-3-ynyl, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate methyl, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-Trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, amethoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]ethyl pyrazole-3-carboxylate (which may be prepared from the methods described in WO 2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]ethyl pyrazole-3-carboxylate (which may be prepared from the methods described in WO 2020 / 056090), N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester (which may be prepared from the method described in WO 2020 / 097012), N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester (which may be prepared from the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (which may be prepared from the methods described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which may be prepared from the methods described in WO 2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, phenamacryl, 5-amino-1,3,4-Thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, flutianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole- 1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproline, enoxastrobin, methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-eno methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds may be prepared from the methods described in WO 2020 / 079111), methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds may be prepared from the methods described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'- [5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5 -Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2015 / 155075); N'-[5-Bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2018 / 228896). N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[( 1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[( 3-Fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl] ]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the method described in WO 2017 / 153380);1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds were prepared by the method described in WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085); N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl) )-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate ethyl, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017 / 029179);2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro -2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylate (4-phenoxyphenyl)methyl (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 2011 N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (which may be prepared from the method described in WO 2018 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the method described in WO 2018 / 153707); N'-( 2-Chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675);(5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds may be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (these compounds may be prepared from the methods described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]ethyl pyrazole-4-carboxylate (these compounds may be prepared from the methods described in WO 2018 / 065414). can be prepared from the methods described in WO 2018 / 158365; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the methods described in WO 2018 / 202428).

[0177] The compounds of the present invention may also be used in combination with anthelmintics. Such anthelmintics include compounds selected from the macrocyclic lactone class of compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP 0357460, EP 0444964 and EP 0594291. Further anthelmintics include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Pat. No. 5,015,630, WO 9415944 and WO 9522552. Further anthelmintics include benzimidazoles, such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of this class. Further anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Further anthelmintics include flukeicides, such as triclabendazole and clorsulon, and cestocidal drugs, such as praziquantel and epsiprantel.

[0178] The compounds of the invention may also be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintics, and antiparasitic oxazolines, such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 and German Patent No. 19,520,936.

[0179] The compounds of the invention may also be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 9615121, and also in combination with anthelmintic effective cyclic depsipeptides such as those described in WO 9611945, WO 9319053, WO 9325543, EP 0626375, EP 0382173, WO 9419334, EP 0382173 and EP 0503538.

[0180] The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0181] The compounds of the present invention may also be used in combination with terpene alkaloids, such as those described in WO 95 / 19363 or WO 04 / 72086, especially the compounds disclosed therein.

[0182] Other examples of such biologically active compounds with which the compounds of the present invention may be used in combination include, but are not limited to, the following: Organophosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Cadusafos, Chlorethoxyphos, Chlorpyrifos, Chlorfenvinphos, Chlormephos, Demeton, Demeton-S-methyl, Demeton-S-methylsulfone, Diarifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Ethoprophos, Etrimphos, Famfur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonophos, Formothion, Fosthiazate, Heptenophos, Isazophos, Isothioate, Isoxathion, Malathion, Methacryloside phos, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, paraoxon, parathion, parathion methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos methyl, profenofos, propafos, proetamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion.

[0183] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

[0184] Pyrethroids: acrinathrin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate 5-benzyl-3-furylmethyl, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin , deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, zeta-cypermethrin.

[0185] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) Ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) Juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.

[0186] Other antiparasitic drugs: Acequinocyl, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis thuringiensis), bensultap, bifenazate, binapropionate, bromopropylate, BTG-504, BTG-505, camfechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclodene, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzin, flufenprox, fluproxifen, halof Enprox, hydramethylnon, IKI-220, Kanemite, NC-196, Nimgard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, belbutin, bertalec, YI-5301.

[0187] Biological agents: Bacillus thuringiensis subspecies aizawai, kurstaki, Bacillus thuringiensis delta-endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0188] Bactericides: Chlortetracycline, oxytetracycline, streptomycin.

[0189] Other biological agents: enrofloxacin, febantel, penetamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

[0190] The following mixtures of compounds of formula (I) with active ingredients are preferred: The abbreviation "TX" means one compound selected from the group consisting of compounds of formula (I), (II), (II-A), (II-B) and (II-C) or compounds as represented in Tables A-1 to A-78 or in Table T1 (below): Petroleum + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenyl phenylsulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, aramite + TX, arsenic oxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + TX, ammonium Benzyl benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromocyclen + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butylpyridaben + TX, calcium polysulfide + TX, camfechlor + TX, carbanolate + TX, carbophenothione + TX, cymiazole + TX, chinomethionate + TX, chlorbencide + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorphenetole + TX, chlorfenson + TX, Chlorphenesulfide + TX, chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, closantel + TX, coumaphos + TX, crotamiton + TX, crotoxphos + TX, khuflaneb + ​​TX, cyanthoate + TX, DCPM + TX, DDT + TX, demefion + TX, demefion-O + TX, demefion-S + TX, demeton-methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton Ton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicliphos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX,Endothion + TX, Eprinomectin + TX, Ethoate-methyl + TX, Etrimphos + TX, Fenazaflor + TX, Fenbutatin oxide + TX, Fenothiocarb + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubenzimine + TX, Flucycloxuron + TX, Fluenethyl + TX, Fluorobenside + TX, FMC 1137+TX, Formetanate+TX, Formetanate hydrochloride+TX, Formoparanate+TX, γ-HCH+TX, Gliodin+TX, Halfenprox+TX, Hexadecyl cyclopropanecarboxylate+TX, Isocarbophos+TX, Jasmolin I+TX, Jasmolin II+TX, Iodofenphos+TX, Lindane+TX, Malonoben+TX, Mecarbam+TX, Mesfolan+TX, Mesulfen+TX, Methacrifos+TX, Bromide Methyl + TX, metolcarb + TX, mexacarbate + TX, milbemycin oxime + TX, mipafox + TX, monocrotophos + TX, morphothion + TX, moxidectin + TX, naled + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifluridide + TX, nikkomycins + TX, nitrilacarb + TX, nitrilacarb 1:1 chloride Zinc complex + TX, omethoate + TX, oxydeprophos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, fenkapton + TX, phosalone + TX, phospholan + TX, phosphamidon + TX, polychloroterpenes + TX, polynactins + TX, proclonol + TX, promacyl + TX, propoxur + TX, protidathion + TX, protoate + TX, pyrethrin I + TX, pyrethri II+TX, pyrethrins+TX, pyridaphenthion+TX, pyrimitate+TX, quinalphos+TX, quinthiophos+TX, R-1492+TX, phosglycine+TX, rotenone+TX, shradan+TX, cebufos+TX, selamectin+TX, sofamido+TX, SSI-121+TX, sulfiram+TX, sulfuramide+TX, sulfotep+TX, sulfur+TX, diflovidazin+TX, taufluvalinate+TX, TEPP+TX,Terbam+TX, Tetradifon+TX, Tetrasul+TX, Thiafenox+TX, Thiocarboxim+TX, Thiofanox+TX, Thiometon+TX, Thioquinox+TX, Thuringiensin+TX, Triamiphos+TX, Triarat+TX, Triazophos+TX, Triazuron+TX, Trifenophos+TX, Trinactin+TX, Vamidothion+TX, Vaniliprole+TX, Bethoxazin+TX, Copper dioctanoate+TX, Copper sulfate+TX, Sibutrin+TX, Dicloron+TX, Dichlorophen+TX, Endothal+TX, Fentin+TX, Slaked lime+TX, Nabam+TX, Quinoclamine+TX, Quinonamide+TX, Simazine+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Crufomate+TX, Piperazine+TX, Thiophanate+TX, Chloralose+TX , Fenthion + TX, Pyridin-4-amine + TX, Strychnine + TX, 1-Hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-Hydroxyquinoline sulfate + TX, Bronopol + TX, Copper hydroxide + TX, Cresol + TX, Dipyrithione + TX, Dodizin + TX, Fenaminosulf + TX, Formaldehyde + TX, Hydragafen + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Nickel bis(dimethyldithiocarbamate) + TX, Nitrapyrin + TX, Octilinone + TX, Oxolinic acid + TX, Oxytetracycline + TX, Hydroxyquinoline sulfate potassium + TX, Probenazole + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Tecloftalam + TX, Thiomersal + TX, Adoxophyes orana GV+TX, Agrobacterium radiobacter+TX, Amblyseius spp.+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Autographa californica NPV+TX, Bacillus sphaericus Neide+TX, Beauveria bronniartii NPV+TX, brongniartii+TX, Chrysoperla carnea+TX, Cryptolaemus montrouzieri+TX, Cydia pomonella GV+TX, Dacnusa sibirica+TX, Diglyphus isaea+TX, Encarsia formosa+TX, Eretmocerus eremicus+TX, Heterorhabditis bacteriophora and H. megidis+TX, Hippodamia convergens+TX, Leptomastix dactylopii+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var.acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Neodiprionsertifer NPV and N.lecontei NPV+TX, Orius spp.+TX, Paecilomyces fumosoroseus+TX, Phytoseiulus persimilis+TX, Steinernema bibionis+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glacerai glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.+TX, Trichogramma spp.)+TX, Typhlodromus occidentalis+TX, Verticillium lecanii+TX, Apholate+TX, Visadil+TX, Busulfan+TX, Zimatif+TX, Hemel+TX, Hempa+TX, Metepa+TX, Methiotepa+TX, Methyl Apholate+TX, Molzide+TX, Penfluron+TX, Tepa+TX, Thiohempa+TX, Thiotepa+TX, Tretamine+TX, Uredep+TX, (E)-Deca-5-en-1-yl and (E)-Deca-5-en-1-ol Acetate+TX, Acetate (E) -Trideca-4-en-1-yl + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en-1 0-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene 4-Methylnonan-5-ol and 4-methylnonan-5-one + TX, α-multistriatin + TX, brevicomin + TX, codrelure + TX, codremon + TX, curuleure + TX, disparleure + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8 + TX, 10-dien-1-yl acetate + TX, dominicalure + TX, ethyl 4-methyloctanoate + TX,. Eugenol + TX, Frontalin + TX, Grand Lua + TX, Grand Lua I + TX, Grand Lua II + TX, Grand Lua III + TX, Grand Lua IV + TX, Hexalua + TX, Ipsdienol + TX, Ipsenol + TX, Japonilua + TX, Lineatin + TX, Littleua + TX, Looplua + TX, Medulua + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalua + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfular + TX, Orictal A+TX, Ostramon+TX, Sigurua+TX, Soldidin+TX, Sulcatol+TX, Tetradec-11-en-1-yl acetate+TX, Trimedrure+TX, Trimedrure A+TX, Trimedrure B1+TX, Trimedrure B2+TX, Trimedrure C+TX, Trunkol+TX, 2-(octylthio)ethanol+TX, Butopyroneoxyl+TX, Butoxy(polypropylene glycol)+TX, Dibutyl adipate+TX, Dibutyl phthalate+TX, Dibutyl succinate+TX, Diethyltoluamide+TX, Dimethylcarbamate+TX, Phthal ... Dimethyl ether + TX, Ethyl hexanediol + TX, Hexamide + TX, Methoxybutyl + TX, Methyl neodecane amide + TX, Oxamate + TX, Picaridin + TX, 1-Dichloro-1-nitroethane + TX, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-Dichloropropane and 1,3-Dichloropropene + TX, 1-Bromo-2-chloroethane + TX, 2,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-Dichlorovinyl 2-Ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyldiethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-thiocyanatoethyl laurate + TX,3-Bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixicarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis δ endotoxins + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408+TX, β-cyfluthrin+TX, β-cypermethrin+TX, bioethanomethrin+TX, biopermethrin+TX, bis(2-chloroethyl)ether+TX, borax+TX, bromfenvinphos+TX, bromo-DDT+TX, bufencarb+TX, butacarb+TX, butathiophos+TX, butonate+TX, calcium arsenate+TX, calcium cyanide+TX, carbon disulfide+TX, tetrahydrofuran Carbon chloride + TX, Cartap hydrochloride + TX, Cevadine + TX, Chlorbicyclen + TX, Chlordane + TX, Chlordecone + TX, Chloroform + TX, Chloropicrin + TX, Chlorphoxime + TX, Chlorprazophos + TX, cis-resmethrin + TX, Cismethrin + TX, Clocitrin + TX, Copper acetoarsenite + TX, Copper arsenate + TX, Copper oleate + TX, Cumitoate + TX, Cryolite + TX, CS 708+TX, Cyanofenphos+TX, Cyanophos+TX, Cicrethrin+TX, Sithioate+TX, d-Tetramethrin+TX, DAEP+TX, Dazomet+TX, Decarbofuran+TX, Diamidaphos+TX, Dikapton+TX, Diclofenthion+TX, Dicresyl+TX, Dicyclanil+TX, Dieldrin+TX, Diethyl 5-methylpyrazol-3-yl phosphate+TX, Dirol+TX, Dimefluthrin+TX, Dimethane+TX, Dimethryn+TX, Dimethylvinphos+TX, Dimethyllan+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX,Diofenolan + TX, Dioxabenzophos + TX, Dicyclophos + TX, DSP + TX, Ecdysterone + TX, EI 1642+TX, EMPC+TX, EPBP+TX, Ethaphos+TX, Ethiofencarb+TX, Ethyl formate+TX, Ethylene dibromide+TX, Ethylene dichloride+TX, Ethylene oxide+TX, EXD+TX, Fenchlorphos+TX, Fenetacarb+TX, Fenitrothion+TX, Fenoxacrim+TX, Fenpyritrin+TX, Fensulfothion+TX, Fenthion-ethyl+TX, Flucofuron+TX, Fosmetilan+TX, Fospirate+TX, Hostietane+TX, Furathiocarb+TX, Frethrin+TX, Guazatine+TX, Guazatine acetate+TX, Sodium tetrathiocarbonate+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterofos+TX, HHDN+TX, Hydrogen cyanide+TX, Hikincarb+TX, IPSP+TX, Isazophos+TX, Isobenzan+ TX, Isodrin + TX, Isofenphos + TX, Isolane + TX, Isoprothiolane + TX, Isoxathion + TX, Juvenile hormone I + TX, Juvenile hormone II + TX, Juvenile hormone III + TX, Kerevan + TX, Kinoprene + TX, Lead arsenate + TX, Leptophos + TX, Lilimphos + TX, Ritidathion + TX, m-Cumenyl methyl carbamate + TX, Magnesium phosphide + TX, Magidox + TX, Mecarfone + TX, Menazone + TX, Mercurous chloride + TX, Mesulfenphos + TX, Metam + TX, Metam potassium + TX, Metam sodium + TX, Methanesulfonyl fluoride + TX, Metoclotophos + TX, Methoprene + TX, Methotrin + TX, Methoxychlor + TX, Methyl isothiocyanate + TX, Methyl chloroform + TX, Methylene chloride + TX, Methoxadiazone + TX, Mylex + TX, Naphthalophos + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nicotine sulfate + TX, Nithiazine + TX, Nornicotine + TX, Ethylphosphonothioate O-5-dichloro-4-iodophenyl O-ethyl + TX, O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate O,O-diethyl + TX, O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate O,O-diethyl + TX, Dithiopyrophosphate O,O,O',O'-Tetrapropyl+TX, Oleic acid+TX, Paradichlorobenzene+TX, Parathion methyl+TX, Pentachlorophenol+TX, Pentachlorophenyl laurate+TX, PH 60-38+TX, Fenkapton+TX, Phosnichlor+TX, Phosphine+TX, Phoxim methyl+TX, Pyrimetaphos+TX, Polychlorodicyclopentadiene isomers+TX, Potassium arsenite+TX, Potassium thiocyanate+TX, Precocene I+TX, Precocene II+TX, Precocene III+TX, Primidophos+TX, Profluthrin+TX, Promecarb+TX, Prothiophos+TX, Pyrazophos+TX, Pyresmethrin+TX, Cassia+TX, Quinalphos methyl+TX, Quinothione+ TX, Lafoxanide+TX, Resmethrin+TX, Rotenone+TX, Cadetrin+TX, Riania+TX, Ryanodine+TX, Sabadila+TX, Schraderdan+TX, Cebufos+TX, SI-0009+TX, Tiapronil+TX, Sodium arsenite+TX, Sodium cyanide+TX, Sodium fluoride+TX, Sodium hexafluorosilicate+TX, Sodium pentachlorophenoxide+TX, Sodium selenate+TX, Sodium thiocyanate+TX, Sulcofuron+TX, Sulcofuron Sodium+TX, Sulfuryl Fluoride+TX, Sulprofos+TX, Tar Oil+TX, Thazimcarb+TX, TDE+TX, Tebupirimfos+TX, Temephos+TX, Terallethrin+TX, Tetrachloroethane+TX, Cyclofos+TX, Thiocyclam+TX, Thiocyclam Hydrogen Oxalate+TX, Thionazine+TX, Thiosultap+TX, Thiosultap Sodium+TX, Tralomethrin+TX, Transpermethrin+TX, Triazamate+TX, Trichloromethaphos-3+TX, Trichlorone acetamide + TX, trimethacarb + TX, tolprocarb + TX, triclopyricarb + TX, triplen + TX, veratridine + TX, veratrine + TX, XMC + TX, zetamethrin + TX, zinc phosphide + TX, zolaprofos + TX, and meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-Dibromo-3-chloropropane + TX, 1,3-Dichloropropene + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + TX, Benclothiaz + TX, Cytokinins + TX, DCIP + TX, Furfural + TX, Isamidophos + TX, Kinetin + TX, Myrothecium verrucaria (Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenols + TX, zeatin + TX, potassium ethylxanthate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, Reynoutria sachalinensis) extract +TX, α-chlorohydrin +TX, anthurium +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocoumafen +TX, fluoroacetamide +TX, flupropazine +TX, flupropazine hydrochloride +TX, norbormide +TX, fosacetim +TX, phosphorus +TX, pindone +TX, pyrinuron +TX, sciriloside +TX, sodium fluoroacetate +TX, thallium sulfate +TX, warfarin +TX, 2-(2-butoxyethoxy)ethyl piperonate +TX, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, Farnesol and Nerolidol + TX, Verbutin + TX, MGK 264 + TX, Piperonyl butoxide + TX, Piprotal + TX, Propyl isomer + TX, S421 + TX, Sesamex + TX, Sesamolin + TX, Sulfoxide + TX, Anthraquinone + TX, Copper naphthenate + TX, Copper oxychloride + TX, Dicyclopentadiene + TX, Thiram + TX, Zinc naphthenate + TX, Ziram + TX, Imanin + TX, Ribavirin + TX, Mercuric oxide + TX, Thiophanate methyl + TX,, Azaconazole + TX, Bitertanol + TX, Bromuconazole + TX, Cyproconazole + TX, Difenoconazole + TX, Diniconazole + TX, Epoxiconazole + TX, Fenbuconazole + TX, Fluquinconazole + TX, Flusilazole + TX, Flutriafol + TX, Furametpyr + TX, Hexaconazole + TX, Imazalil + TX, Imibenconazole + TX, Ipconazole + TX, Metconazole + TX, Myclobutanil + TX, Paclobutrazol + TX, Pefurazoate + TX, Penconazole + TX, Prothioco nazol+TX, pyrifenox+TX, prochloraz+TX, propiconazole+TX, pyrisoxazole+TX, simeconazole+TX, tebuconazole+TX, tetraconazole+TX, triadimefon+TX, triadimenol+TX, triflumizole+TX, triticonazole+TX, ancymidol+TX, fenarimol+TX, nuarimol+TX, bupirimate+TX, dimethirimol+TX, ethirimol+TX, dodemorph+TX, fenpropidin+TX, fenpropimorph+TX, spiroxamine+TX, tridemorph+T X, cyprodinil+TX, mepanipyrim+TX, pyrimethanil+TX, fenpiclonil+TX, fludioxonil+TX, benalaxyl+TX, furalaxyl+TX, metalaxyl-+TX, R-metalaxyl+TX, ofurace+TX, oxadixyl+TX, carbendazim+TX, debacarb+TX, fuberidazole+TX, thiabendazole+TX, chlozolinate+TX, diclozolin+TX, mycozolin+TX, procymidone+TX, vinclozolin+TX, boscalid+TX, carboxin+TX, fenfuram+TX, flutolanil+TX , Mepronil+TX, Oxycarboxin+TX, Penthiopyrad+TX, Thifluzamide+TX, Dodine+TX, Iminoctadine+TX, Azoxystrobin+TX, Dimoxystrobin+TX, Enestrobulin+TX, Phenaminestrobin+TX, Flufenoxystrobin+TX, Fluoxastrobin+TX, Kresoximmethyl+TX, Metominostrobin+TX, Trifloxystrobin+TX, Orysastrobin+TX, Picoxystrobin+TX, Pyraclostrobin+TX, Pyrametstrobin+TX, Pyraoxystrobin+TX,Ferbam+TX, Mancozeb+TX, Maneb+TX, Methiram+TX, Probineb+TX, Zineb+TX, Captafol+TX, Captan+TX, Fluorimide+TX, Folpet+TX, Tolylfluanid+TX, Bordeaux mixture+TX, Copper oxide+TX, Mancopper+TX, Oxine copper+TX, Nitrotarisopropyl+TX, Edifenphos+TX, Iprobenfos+TX, Phosdifen+TX, Tolclofosmethyl+TX, Anilazine+TX, Benthiavalicarb+TX, Blasticidin-S+TX, Chloroneb+TX , Chlorothalonil+TX, Cyflufenamid+TX, Cymoxanil+TX, Cyclobutrifluram+TX, Diclocymet+TX, Diclomedine+TX, Dicloran+TX, Diethofencarb+TX, Dimethomorph+TX, Flumorph+TX, Dithianon+TX, Ethaboxam+TX, Etridiazole+TX, Famoxadone+TX, Fenamidone+TX, Fenoxanil+TX, Ferimzone+TX, Fluazinam+TX, Fluopicolide+TX, Flusulfamide+TX, Fluxapyroxad+TX, Fenhexamid+T X, fosetyl-aluminum + TX, hymexazole + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX, phthalide + TX, polyoxins + TX, propamocarb + TX, pyribencarb + TX, proquinazid + TX, pyroquilon + TX, pyriophenone + TX, quinoxyfen + TX, quintozene + TX, tiadinil + TX, triazoxide + TX, tricyclazole + TX, triforine + TX, validamycin + TX, valifenalate + TX, Zoxamide + TX, Mandipropamide + TX, Fluveneteram + TX, Isopyrazam + TX, Sedaxane + TX, Benzovindiflupyr + TX, Pydiflumetofen + TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, Isoflucipram + TX, Isotianil + TX, Dipimethitrone + TX, 6-Ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX,2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, Fluindapyr + TX, Qumethoxystrobin (Jiaxiangjun) Jiaxiangjunzhi) + TX, lvbenmixianan + TX, diclobentiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl) quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate tert-butyl + TX, pyraziflumide + TX, impilfluxam + TX, tolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetate N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamic acid but-3-ynyl salt + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl salt + TX, 3-chloro-6-methyl-5-furanyl salt + TX, phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl )phenoxy]methyl]phenyl]tetrazol-5-one+TX, aminopyrifen+TX, amethoctrazine+TX, amisulbrom+TX, penflufen+TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide+TX, florylpicoxamide+TX, fenpicoxamide+TX, tebufloquine+TX, ipflufenoquine+TX, quinofumelin+TX, isofetamide+TX, N-[2-[2,4-Dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, Benzothiostrobin + TX, Fenamacril + TX, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram + TX, Flutianil + TX, Fluopimomi TX, pyrapropione + TX, picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pi lysyl]oxy]benzonitrile + TX, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiproline + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluro[4-methylphenyl]pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-Triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[ 5-Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (these compounds can be prepared from the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds were prepared from the method described in WO 2018 / 228896). N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared from the method described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[( 1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[( 3-Fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl] ]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared from the method described in WO 2017 / 153380);1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds were prepared by the method described in International Publication WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared from the methods described in WO 2016 / 156085); N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-Ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, -yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol- a compound selected from the group of substances consisting of: 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethyl pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph may be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689;2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); 2-amino-6- Methyl-pyridine-3-carboxylate (4-phenoxyphenyl)methyl + TX (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone + TX (this compound can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbazole + TX (this compound can be prepared from the method described in WO 2011 / 138281); rubothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX;N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared from the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared from the methods described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]ethyl pyrazole-4-carboxylate + TX (this compound can be prepared from the methods described in WO 2018 / 158365);2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benz amide+TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX (these compounds may be prepared from the method described in WO 2018 / 202428), chloroinconazide+TX, flumethylsulfolim+TX, fluoxythioconazole+TX, flufenoxadiazam+TX, methallylpicoxamide+TX;

[0191] The references in square brackets after the active ingredients, e.g. [3878-19-1], refer to Chemical Abstracts Registry Numbers. The above-mentioned mixing partners are known. When the active ingredients are listed in "The Pesticide Manual" [The Pesticide Manual-A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are listed therein under the entry numbers given above in parentheses for the particular compound; for example, the compound "Abamectin" is listed under entry number (1). When "[CCN]" is added above to a particular compound, the compound is listed in the "Compendium of Pesticide Common Names" accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright® 1995-2004]; for example, the compound "acetoprole" is listed at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0192] Most of the active ingredients mentioned above are referred to above by their so-called "common names", where in each case the relevant "ISO common name" or another "common name" is used. If the name is not a "common name", the nature of the name used instead is given in parentheses for the particular compound; in that case, the IUPAC name, IUPAC / Chemical Abstracts name, "Chemical name", "Customary name", "Compound name" or "Development code" is used, or, if none of these names and no "common name" is used, an "alternative name" is utilized. "CAS Registry Number" means Chemical Abstracts Registry Number.

[0193] The mixture of the active ingredient of the compound of formula (I) selected from the group consisting of the compounds of formula (I), formula (II), formula (II-A), formula (II-B) and formula (II-C), or the compounds as shown in Table A-1 to Table A-78, or one compound selected from the group consisting of the compounds P-1 to P-11 listed in Table T1 (below) is preferably in a mixing ratio of 100:1 to 1:100, particularly 50:1 to 1:50, more particularly 20:1 to 1:20, even more particularly 10:1 to 1:10, and even more preferably 2:1 to 1:2. Such a mixing ratio is based on weight.

[0194] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, e.g. unepoxidized or epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents, e.g. silicone oils, preservatives, viscosity regulators, binders and / or adhesives, fertilizers or other active ingredients to achieve a particular effect, e.g. fungicides, bactericides / fungicides, nematicides, plant activators, molluscicides or herbicides.

[0195] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by pulverizing, screening and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing and / or pulverizing the active ingredient with one or more auxiliary agents. These preparation processes of the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0196] Another aspect of the present invention relates to the use of a compound of formula (I) according to the present invention 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 fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, in admixture with other fungicides or insecticides as defined herein above, for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation products, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic microorganisms, e.g. insects or preferably fungal organisms.

[0197] A further aspect of the present invention relates to a method for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation materials, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic or spoilage microorganisms or organisms that are potentially harmful to humans, in particular fungal organisms, which method comprises the step of applying a compound of formula (I) according to the present invention or a preferred individual compound as defined herein as active ingredient to the plant, a part of the plant or its habitat, its propagation materials, or any part of the non-living material.

[0198] By control or prevention is meant reducing infestation by insects or spoilage microorganisms or organisms that are plant pathogenic or potentially harmful to humans, particularly fungal organisms, to a level that demonstrates improvement.

[0199] A preferred method for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which involves the application of a compound of formula (I) according to the invention or an agrochemical composition containing at least one compound of formula (I), is foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) according to the invention can also be introduced into the plant by the roots via the soil (systemic action) by irrigating the plant habitat with a liquid formulation or by applying the compounds to the soil in solid form, for example in granular form (soil application). In the case of rice crops, such granules can be applied to flooded rice fields. The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0200] Formulations, e.g. compositions containing the compounds of formula (I) according to the invention and, if desired, solid or liquid auxiliaries or monomers encapsulating the compounds of formula (I), can be prepared in a known manner, typically by homogeneously mixing and / or grinding the compounds together with extenders, e.g. solvents, solid carriers and optional surface-active compounds (surfactants).

[0201] Advantageous applications are usually from 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably from 10 g to 1 kg ai / ha, most preferably from 20 g to 600 g ai / ha.When used as a seed drench, a convenient dosage is from 10 mg to 1 g of active substance per kg of seeds.

[0202] The term "g ai / ha" as used herein refers to the application rate given as grams [g] of active ingredient [ai] per unit surface [ha]. The hectare (symbol ha) is a square measuring 100 m on a side (1 hm 2 ) or 10,000 square metres. The hectare is a commonly used metric unit of area.

[0203] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0204] Preferably, the compositions comprising the compounds of formula (I) according to the present invention are applied prophylactically, meaning before the onset of a disease, or therapeutically, meaning after the onset of a disease.

[0205] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), sorbent granules (RM ... The present invention may be employed in the form of an emulsion, such as an EG, an emulsion, a water-in-oil (EO), an emulsion, an oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), a very low volume suspension (SU), a very low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any technically desirable formulation in combination with an agriculturally acceptable adjuvant.

[0206] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with suitable inert compounding agents (diluents, solvents, fillers, and any other compounding agents such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds that provide adjuvant activity effects). Conventional slow-release formulations can also be employed when long-lasting efficacy is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvant effects, such as, for example, condensates of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0207] The seed dressing formulation is applied to the seed in a manner known per se, utilizing the combination and diluent of the present invention in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seed. 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 encapsulated form, for example as a slow release capsule or microcapsule.

[0208] In general, the formulations contain 0.01-90% by weight of active agent, 0-20% of agriculturally acceptable surfactants and 10-99.99% of solid or liquid inert compounding agents and adjuvants, the active agent being at least a compound of formula (I) according to the invention, optionally together with other active agents, in particular microbicides, preservatives, etc. Concentrated forms of the composition generally contain about 2-80%, preferably about 5-70% by weight of active agent. Application forms of the formulations may contain, for example, 0.01-20% by weight, preferably 0.01-5% by weight of active agent. Commercial products will preferably be formulated as concentrates, but end users will usually utilize diluted formulations.

[0209] Although it is preferred to formulate commercial products as concentrates, end users will typically dilute the formulations when used.

[0210] A preferred formula may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1-30%, preferably 5-20% Liquid carrier: 1-80%, preferably 1-35%

[0211] Dust: Active ingredient: 0.1-10%, preferably 0.1-5% Solid carrier: 99.9-90%, preferably 99.9-99%

[0212] Suspension concentrates: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0213] Wettable powder: Active ingredient: 0.5-90%, preferably 1-80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5-95%, preferably 15-90%

[0214] Granules: Active ingredient: 0.1-30%, preferably 0.1-15% Solid carrier: 99.5-70%, preferably 97-85%

[0215] The disclosure in this application makes available each and every combination of the embodiments disclosed herein.

[0216] The compounds according to the following Tables A-1 to A-78 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the present invention and to show preferred compounds of formula (I). In any of the following Tables A-1 to A-78, the possible presence of one or more asymmetric carbon atoms in the compound of formula (I) according to the present invention means that the compound can occur in chiral isomeric form, i.e., in enantiomeric or diastereomeric form.

[0217] Table A This table includes compounds of formula (A): [ka] In the formula, R 2 , R 4 , R 5 , R 6 , Q and G are as defined in Tables A-1 to A-78 below, and G is any of G1, G2, G3, G4, G5 or G6 as defined in Table 1 below.

[0218] [Table 1]

[0219] The definition of Q in the compound of formula (A) is as defined above for the compound of formula (II) according to the invention.

[0220] Table A-1: ​​This table provides six compounds of formula (A), A-1.01 to A-1.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-1, where R 9a and R 9c is chlorine, and G is as defined in Table 1.

[0221] For example, compound A-1.01 has the following structure: [ka] Compound A-1.01

[0222] Table A-2: This table provides six compounds of formula (A), A-2.01 to A-2.06, in which R 2 , R 5 , R 6 is hydrogen, Q is Q-1, where R 9a and R 9c is hydrogen, and G is as defined in Table 1.

[0223] Table A-3: This table provides six compounds of formula (A), A-3.01 to A-3.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-1, where R 9a is hydrogen and R 9c is chlorine, and G is as defined in Table 1.

[0224] Table A-4: This table provides six compounds of formula (A), A-3.01 to A-3.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-1, where R 9a is chlorine and R 9c is hydrogen, and G is as defined in Table 1.

[0225] Table A-5: This table provides six compounds of formula (A), A-5.01 to A-5.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-2, where R 9a and R 9b is chlorine, and G is as defined in Table 1.

[0226] For example, compound A-5.02 has the following structure: [ka] Compound A-5.02

[0227] Table A-6: This table provides six compounds of formula (A), A-6.01 to A-6.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-2, where R 9a and R 9b is hydrogen, and G is as defined in Table 1.

[0228] Table A-7: This table provides six compounds of formula (A), A-7.01 to A-7.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-2, where R 9a is hydrogen, and R 9b is chlorine, and G is as defined in Table 1.

[0229] Table A-8: This table provides six compounds of formula (A), A-8.01 to A-8.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-2, where R 9a is chlorine, R 9b is hydrogen, and G is as defined in Table 1.

[0230] Table A-9: This table provides six compounds of formula (A), A-9.01 to A-9.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-3, where R 9b and R 9c is chlorine, and G is as defined in Table 1.

[0231] Table A-10: This table provides six compounds of formula (A), A-10.01 to A-10.06, in which R2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-3, where R 9b and R 9c is hydrogen, and G is as defined in Table 1.

[0232] Table A-11: This table provides six compounds of formula (A), A-11.01 to A-11.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-3, where R 9b is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0233] Table A-12: This table provides six compounds of formula (A), A-12.01 to A-12.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-3, where R 9b is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0234] Table A-13: This table provides six compounds of formula (A), A-13.01 to A-13.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-7, where R 10b is methyl, R 9a and R 9c is chlorine, and G is as defined in Table 1.

[0235] Table A-14: This table provides six compounds of formula (A), A-14.01 to A-14.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-7, where R10b is methyl, R 9a and R 9c is hydrogen, and G is as defined in Table 1.

[0236] For example, compound A-14.03 has the following structure: [ka] Compound A-14.03

[0237] Table A-15: This table provides six compounds of formula (A), A-15.01 to A-15.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-7, where R 10b is methyl, R 9a is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0238] Table A-16: This table provides six compounds of formula (A), A-16.01 to A-16.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen, Q is Q-7, where R 10b is methyl, R 9a is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0239] Table A-17: This table provides six compounds of formula (A), A-17.01 to A-17.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-8, where R 10c is methyl, R 9a and R 9b is chlorine, and G is as defined in Table 1.

[0240] Table A-18: This table provides six compounds of formula (A), A-18.01 to A-18.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-8, where R 10c is methyl, R 9a and R 9b is hydrogen, and G is as defined in Table 1.

[0241] Table A-19: This table provides six compounds of formula (A), A-19.01 to A-19.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-8, where R 10c is methyl, R 9a is hydrogen, and R 9b is chlorine, and G is as defined in Table 1.

[0242] Table A-20: This table provides six compounds of formula (A), A-20.01 to A-20.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-8, where R 10c is methyl, R 9a is chlorine, R 9b is hydrogen, and G is as defined in Table 1.

[0243] Table A-21: This table provides six compounds of formula (A), A-21.01 to A-21.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-9, where R 10a is methyl, R 9b and R 9c is chlorine, and G is as defined in Table 1.

[0244] Table A-22: This table provides six compounds of formula (A), A-22.01 to A-22.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-9, where R 10a is methyl, R 9b and R 9c is hydrogen, and G is as defined in Table 1.

[0245] Table A-23: This table provides six compounds of formula (A), A-23.01 to A-23.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-9, where R 10a is methyl, R 9b is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0246] Table A-24: This table provides six compounds of formula (A), A-24.01 to A-24.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-9, where R 10a is methyl, R 9b is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0247] Table A-25: This table provides six compounds of formula (A), A-25.01 to A-25.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-10, where R 9c is chlorine, and G is as defined in Table 1.

[0248] Table A-26: This table provides six compounds of formula (A), A-26.01 to A-26.06, in which R2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-10, where R 9c is hydrogen, and G is as defined in Table 1.

[0249] For example, compound A-26.01 has the following structure: [ka] Compound A-26.01

[0250] Table A-27: This table provides six compounds of formula (A), A-27.01 to A-27.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-11, where R 9b is chlorine, and G is as defined in Table 1.

[0251] Table A-28: This table provides six compounds of formula (A), A-28.01 to A-28.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-11, where R 9b is hydrogen, and G is as defined in Table 1.

[0252] Table A-29: This table provides six compounds of formula (A), A-29.01 to A-29.06, in which R 2 , R 4 , R 5 , R 6 is hydrogen and Q is Q-12, where R 9b is chlorine, and G is as defined in Table 1.

[0253] Table A-30: This table provides six compounds of formula (A), A-30.01 to A-30.06, in which R 2 , R 4 , R5 , R 6 is hydrogen and Q is Q-12, where R 9b is hydrogen, and G is as defined in Table 1.

[0254] Table A-31: This table provides six compounds of formula (A), A-31.01 to A-31.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a and R 9c is chlorine, and G is as defined in Table 1.

[0255] For example, compound A-31.01 has the following structure: [ka] Compound A-31.01

[0256] Table A-32: This table provides six compounds of formula (A), A-32.01 to A-32.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a and R 9c is hydrogen, and G is as defined in Table 1.

[0257] Table A-33: This table provides six compounds of formula (A), A-33.01 to A-33.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0258] Table A-34: This table provides six compounds of formula (A), A-34.01 to A-34.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0259] Table A-35: This table provides six compounds of formula (A), A-35.01 to A-35.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a and R 9b is chlorine, and G is as defined in Table 1.

[0260] Table A-36: This table provides six compounds of formula (A), A-36.01 to A-36.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a and R 9b is hydrogen, and G is as defined in Table 1.

[0261] Table A-37: This table provides six compounds of formula (A), A-37.01 to A-37.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a is hydrogen, and R 9b is chlorine, and G is as defined in Table 1.

[0262] Table A-38: This table provides six compounds of formula (A), A-38.01 to A-38.06, in which R 2 , R 5 , R6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a is chlorine, R 9b is hydrogen, and G is as defined in Table 1.

[0263] Table A-39: This table provides six compounds of formula (A), A-39.01 to A-39.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b and R 9c is chlorine, and G is as defined in Table 1.

[0264] Table A-40: This table provides six compounds of formula (A), A-40.01 to A-40.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b and R 9c is hydrogen, and G is as defined in Table 1.

[0265] Table A-41: This table provides six compounds of formula (A), A-41.01 to A-41.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0266] Table A-42: This table provides six compounds of formula (A), A-42.01 to A-42.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b is chlorine, R9c is hydrogen, and G is as defined in Table 1.

[0267] Table A-43: This table provides six compounds of formula (A), A-43.01 to A-43.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-7, where R 10b is methyl, R 9a , R 9c is chlorine, and G is as defined in Table 1.

[0268] Table A-44: This table provides six compounds of formula (A), A-44.01 to A-44.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-7, where R 10b is methyl, R 9a , R 9c is hydrogen, and G is as defined in Table 1.

[0269] For example, compound A-44.03 has the following structure: [ka] Compound A-44.03

[0270] Table A-45: This table provides six compounds of formula (A), A-45.01 to A-45.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-7, where R 10b is methyl, R 9a is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0271] Table A-46: This table provides six compounds of formula (A), A-46.01 to A-46.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-7, where R 10b is methyl, R 9a is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0272] Table A-47: This table provides six compounds of formula (A), A-47.01 to A-47.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-8, where R 10c is methyl, R 9a , R 9b is chlorine, and G is as defined in Table 1.

[0273] Table A-48: This table provides six compounds of formula (A), A-48.01 to A-48.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-8, where R 10c is methyl, R 9a , R 9b is hydrogen, and G is as defined in Table 1.

[0274] Table A-49: This table provides six compounds of formula (A), A-49.01 to C-49.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-8, where R 10c is methyl, R 9a is hydrogen, and R 9b is chlorine, and G is as defined in Table 1.

[0275] Table A-50: This table provides six compounds of formula (A), A-50.01 to A-50.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-8, where R 10c is methyl, R 9a is chlorine, R 9b is hydrogen, and G is as defined in Table 1.

[0276] Table A-51: This table provides six compounds of formula (A), A-51.01 to A-51.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-9, where R 10a is methyl, R 9b and R 9c is chlorine, and G is as defined in Table 1.

[0277] Table A-52: This table provides six compounds of formula (A), A-52.01 to A-52.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-9, where R 10a is methyl, R 9b , R 9c is hydrogen, and G is as defined in Table 1.

[0278] Table A-53: This table provides six compounds of formula (A), A-53.01 to A-53.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-9, where R 10a is methyl, R 9b is hydrogen, and R 9c is chlorine, and G is as defined in Table 1.

[0279] Table A-54: This table provides six compounds of formula (A), A-54.01 to A-54.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-9, where R 10a is methyl, R 9b is chlorine, R 9c is hydrogen, and G is as defined in Table 1.

[0280] Table A-55: This table provides six compounds of formula (A), A-55.01 to A-55.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-10, where R 9c is chlorine, and G is as defined in Table 1.

[0281] Table A-56: This table provides six compounds of formula (A), A-56.01 to A-56.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-10, where R 9c is hydrogen, and G is as defined in Table 1.

[0282] For example, compound A-56.01 has the following structure: [ka] Compound A-56.01

[0283] Table A-57: This table provides six compounds of formula (A), A-57.01 to A-57.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-11, where R 9bis chlorine, and G is as defined in Table 1.

[0284] Table A-58: This table provides six compounds of formula (A), A-58.01 to A-58.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-11, where R 9b is hydrogen, and G is as defined in Table 1.

[0285] Table A-59: This table provides six compounds of formula (A), A-59.01 to A-59.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-12, where R 9b is chlorine, and G is as defined in Table 1.

[0286] Table A-60: This table provides six compounds of formula (A), A-60.01 to A-60.06, in which R 2 , R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-12, where R 9b is hydrogen, and G is as defined in Table 1.

[0287] Table A-61: This table provides six compounds of formula (A), A-61.01 to A-61.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a , R 9c is chlorine, and G is as defined in Table 1.

[0288] For example, compound A-61.01 has the following structure: [ka] Compound A-61.01

[0289] Table A-62: This table provides six compounds of formula (A), A-62.01 to A-62.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a , R 9c is hydrogen, and G is as defined in Table 1.

[0290] Table A-63: This table provides six compounds of formula (A), A-63.01 to A-63.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a is hydrogen and R 9c is chlorine, and G is as defined in Table 1.

[0291] Table A-64: This table provides six compounds of formula (A), A-64.01 to A-64.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-1, where R 9a is chlorine and R 9c is hydrogen, and G is as defined in Table 1.

[0292] Table A-65: This table provides six compounds of formula (A), A-65.01 to A-65.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a and R 9b is chlorine, and G is as defined in Table 1.

[0293] Table A-66: This table provides six compounds of formula (A), A-66.01 to A-66.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a , R 9b is hydrogen, and G is as defined in Table 1.

[0294] Table A-67: This table provides six compounds of formula (A), A-67.01 to A-67.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a is hydrogen and R 9b is chlorine, and G is as defined in Table 1.

[0295] Table A-68: This table provides six compounds of formula (A), A-68.01 to A-68.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-2, where R 9a is chlorine and R 9b is hydrogen, and G is as defined in Table 1.

[0296] Table A-69: This table provides six compounds of formula (A), A-69.01 to A-69.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b and R 9c is chlorine, and G is as defined in Table 1.

[0297] Table A-70: This table provides six compounds of formula (A), A-70.01 to A-70.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b , R 9c is hydrogen, and G is as defined in Table 1.

[0298] Table A-71: This table provides six compounds of formula (A), A-71.01 to A-71.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b is hydrogen and R 9c is chlorine, and G is as defined in Table 1.

[0299] Table A-72: This table provides six compounds of formula (A), A-72.01 to A-72.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-3, where R 9b is chlorine and R 9c is hydrogen, and G is as defined in Table 1.

[0300] Table A-73: This table provides six compounds of formula (A), A-73.01 to A-73.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-10, where R 9c is chlorine, and G is as defined in Table 1.

[0301] Table A-74: This table provides six compounds of formula (A), A-74.01 to A-74.06, in which R 2is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-10, where R 9c is hydrogen, and G is as defined in Table 1. For example, compound A-74.01 has the following structure: [ka] Compound A-74.01

[0302] Table A-75: This table provides six compounds of formula (A), A-75.01 to A-75.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-11, where R 9b is chlorine, and G is as defined in Table 1.

[0303] Table A-76: This table provides six compounds of formula (A), A-76.01 to A-76.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-11, where R 9b is hydrogen, and G is as defined in Table 1.

[0304] Table A-77: This table provides six compounds of formula (A), A-77.01 to A-77.06, in which R 2 is methyl, R 5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-12, where R 9b is chlorine, and G is as defined in Table 1.

[0305] Table A-78: This table provides six compounds of formula (A), A-78.01 to A-78.06, in which R 2 is methyl, R5 , R 6 is hydrogen, and R 4 is methyl and Q is Q-12, where R 9b is hydrogen, and G is as defined in Table 1. EXAMPLES

[0306] The examples which follow are intended to illustrate the invention and are not intended to limit it in any way.

[0307] The compounds of the present invention are distinguishable from known compounds by their high efficacy at low application rates, which can be verified by one skilled in the art using the experimental procedures outlined in the examples, and where necessary, low application rates, for example 60 ppm, 20 ppm or 2 ppm.

[0308] The compounds of formula (I) may have any number of benefits including, inter alia, an advantageous level of biological activity for protecting plants against diseases caused by fungi, or superior properties for use as an agrochemical active ingredient (e.g., high biological activity, an advantageous spectrum of activity, an enhanced safety profile (including improved crop tolerance), improved physico-chemical properties, or enhanced biodegradability).

[0309] Throughout this specification temperatures are given in degrees Celsius [° C.] and "mp" means melting point. LC / MS means liquid chromatography mass spectrometry, with a description of the apparatus and methods as follows.

[0310] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer, and chemical shifts were expressed as TMS ( 1 H) and CFCl3( 19F) are given in ppm relative to standard. Spectra were run in deuterated solvents as specified. Compounds were characterized using one of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound were retention time ("Rt", recorded in minutes) and molecular ion (M+H). + or (MH) - were the measured values.

[0311] LC-MS method A: Spectra were recorded on a Waters Corporation mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ion), capillary: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120-150° C., desolvation temperature: 350-600° C., cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 50-900 Da and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode-array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60 °C, DAD wavelength range (nm): 210-400, Run time: 1.5 min; Solvents: A = water + 5% MeOH + 0.05% HC(O)OH, B = acetonitrile + 0.05% HC(O)OH; Flow rate (ml / min) 0.85, Gradient: 10% B isocratic for 0.2 min, then 10 to 100% B in 1.0 min, isocratic at 100% B for 0.2 min, 100 to 10% B in 0.05 min, isocratic at 10% B for 0.05 min.

[0312] Formulation examples [Table 2]

[0313] This combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to give wettable powders which can be diluted with water to produce a suspension of the desired concentration.

[0314] [Table 3]

[0315] This combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder which can be used directly as a seed treatment.

[0316] emulsifiable concentrate Active ingredient: 10% Octylphenol polyethylene glycol ether (4-5 mol ethylene oxide): 3% Calcium dodecylbenzenesulfonate: 3% Castor oil polyglycol ether (35 mol ethylene oxide): 4% Cyclohexanone: 30% Xylene mixture: 50%

[0317] From this concentrate it is possible, by dilution with water, to obtain emulsions of any required dilution which can be used in plant protection.

[0318] [Table 4]

[0319] Ready-to-use dusts are obtained by mixing this combination with a carrier and grinding the mixture in a suitable mill. Such dusts can also be used for dry dressing of seeds.

[0320] Extrusion molding granules Active ingredient: 15% Sodium lignosulfonate: 2% Carboxymethylcellulose: 1% Kaolin: 82%

[0321] The combination is mixed with the auxiliaries, ground, the mixture is moistened with water, extruded and then dried in a stream of air.

[0322] Coated Granules Active ingredient: 8% Polyethylene glycol (mol.wt.200): 3% Kaolin: 89%

[0323] In a mixer, the finely ground combination is applied uniformly to the kaolin moistened with polyethylene glycol, thus obtaining non-dusty coated granules.

[0324] Suspension concentrate Active ingredient: 40% Propylene glycol: 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide): 6% Sodium lignosulfonate: 10% Carboxymethylcellulose: 1% Silicone oil (in the form of a 75% emulsion in water): 1% Water: 32%

[0325] When the finely divided combination is mixed homogeneously with the adjuvants, a suspension concentrate is obtained which can be diluted with water to obtain a suspension of any desired dilution, which can be used to treat and protect living plants and plant propagation materials against microbial infestations by spraying, pouring or immersion.

[0326] Flowable concentrates for seed treatment Active ingredient: 40% Propylene glycol: 5% Copolymer butanol PO / EO: 2% Tristyrene phenol 10-20 mole EO content: 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% solution in water): 0.5% Monoazo pigment calcium salt: 5% Silicone oil (in the form of a 75% emulsion in water): 0.2% Water: 45.3%

[0327] When the finely ground combination is mixed homogeneously with the adjuvants, a suspension concentrate is obtained which can be diluted with water to obtain a suspension of any desired dilution, which can be used to combat and protect living plants and plant propagation materials from microbial damage by spraying, injection or immersion.

[0328] Slow-release capsule suspension 28 parts of the combination are mixed with 2 parts of aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate mixture (8:1). The mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete. The obtained capsule suspension is stabilized by adding 0.25 parts of thickener and 3 parts of dispersant. This capsule suspension formulation contains 28% active ingredient. The median capsule diameter is 8-15 microns. The obtained formulation is applied to the seeds as an aqueous suspension with a device suitable for this purpose.

[0329] Formulation types include emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-suspensions (SU), ultra-liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0330] Abbreviation CDCl3 Deuterated Chloroform DCC Dicyclohexylcarbodiimide DMA Dimethylacetamide DMSO Dimethyl sulfoxide DMSO-d6 Deuterated dimethyl sulfoxide EtOAc Ethyl acetate HCl Hydrochloric acid h / hrs 1 hour / multiple hours LC-MS Liquid Chromatography Mass Spectrometry (LC-MS or LCMS) rh Relative humidity rt room temperature Rt retention time ssp. subspecies THF Tetrahydrofuran

[0331] Preparation Example The compounds of formula (I) according to the invention may be prepared using the synthetic techniques described both above and below.

[0332] Example P1: Preparation of 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propyl]isoxazole-3-carboxamide (compound P-1, Table T1) [ka] (Compound P-1, Table T1) Step A: Preparation of (1-methylpyrazol-3-yl)-(1-methylpyrazol-4-yl)methanol [ka] A 250 mL three-necked round bottom flask equipped with a magnetic stirrer was charged with 3-iodo-1-methyl-pyrazole (2.08 g, 9.99 mmol) dissolved in tetrahydrofuran (THF) (27 mL) as a colorless solution at room temperature. The solution was cooled to 0° C. and a solution of isopropylmagnesium chloride lithium chloride complex in THF (10 mL, 13.62 mmol) was added dropwise over 30 min, keeping the temperature below 5° C. The mixture was stirred at 0° C. for 45 min, then 1-methylpyrazole-4-carbaldehyde (1 g, 9.08 mmol) dissolved in THF was added dropwise via syringe over 10 min. The resulting pale yellow solution was stirred at 0° C. for 10 min and then allowed to warm to room temperature. The reaction was followed by LC-MS and upon completion was cooled to 0° C. and carefully quenched with saturated aqueous NH4Cl. The mixture was diluted with water and the mixture was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered through a sintered disc filter funnel and concentrated in vacuo at 40° C. to give the crude product, which was purified by FC (eluting with an ethyl acetate / cyclohexane gradient) to give (1-methylpyrazol-3-yl)-(1-methylpyrazol-4-yl)methanol. LC-MS (Method A): 193[M+H], retention time: 0.21.

[0333] Step B: Preparation of 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)acetonitrile [ka] A sealed tube equipped with a magnetic stirrer was charged with (1-methylpyrazol-3-yl)-(1-methylpyrazol-4-yl)methanol (0.6 g, 3 mmol) and dichloromethane (20 mL). Lithium carbonate (0.05 g, 0.6 mmol), trimethylsilyl cyanide (1 g, 2 mL) and iodine (1 g, 6 mmol) were then added successively at room temperature. The mixture was stirred at room temperature overnight. The reaction mixture was then cooled to room temperature, poured into saturated aqueous Na2S2O3 and extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by FC (eluted with an ethyl acetate / cyclohexane gradient) to give the title compound as a yellow oil. LC-MS (Method A): 202[M+H], retention time: 0.52 min.

[0334] Step C: Preparation of 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propanenitrile [ka] A sealed tube equipped with a magnetic stirrer and temperature probe was charged with 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)acetonitrile (0.08 g, 0.40 mmol) and tetrahydrofuran (1.6 mL). To this solution was added n-butyllithium (2.5 M in hexanes, 0.19 mL, 0.48 mmol) dropwise under argon atmosphere at -70°C (slight exotherm to -72°C, yellow solution / suspension). The mixture was stirred at this temperature for 25 min, after which iodomethane (0.04 mL, 0.60 mmol) was added dropwise at -70°C (yellow solution). The reaction was stirred at -78°C for 5 min, then at room temperature for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude material was purified by FC (40 g SiO2, eluting with a gradient of ethyl acetate in cyclohexane) to yield 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propanenitrile as a yellow oil. LC-MS (Method A): 216[M+H], retention time: 0.65 min.

[0335] Step D: Preparation of 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine [ka] To a solution of 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propanenitrile (0.08 g, 0.4 mmol) and cobalt dichloride (0.05 g, 0.4 mmol) in methanol (1 mL) at 0 °C, sodium borohydride (0.04 g, 0.9 mmol) was added in small portions. Immediate formation of a black precipitate was observed and the mixture was stirred at 0 °C for 1 h. After LC-MS showed consumption of starting material, 1N HCl was added until the pH of the reaction mixture was 3-4 and the mixture was extracted with dichloromethane to remove non-basic impurities. The pH of the remaining aqueous phase was adjusted to 10 with 2N NaOH and the mixture was extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine as a colorless oil, which was used in the next step without further purification. LC-MS (Method A): 220[M+H], retention time: 0.22 min.

[0336] Step E: Preparation of 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propyl]isoxazole-3-carboxamide (compound P-1, Table T1) A one-necked round-bottom flask equipped with a magnetic stirrer was charged with 2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine (0.03 g, 0.1 mmol), ethyl acetate (1 mL), N,N-diisopropylethylamine (0.07 mL, 0.4 mmol) and 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid (0.03 g, 0.2 mmol). Propylphosphonic anhydride (T3P, 0.2 mL, 0.4 mmol) was then added dropwise at room temperature and the mixture was stirred at room temperature for 60 minutes. The reaction mixture was poured into water (20 mL) and the mixture was extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by reverse-phase flash chromatography to give 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-3-yl)-2-(1-methylpyrazol-4-yl)propyl]isoxazole-3-carboxamide, isolated as a brownish oil. LC-MS (Method A): 427[M+H], retention time: 0.94 min.

[0337] Example P2: Preparation of N-[2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (compound P-4, Table T1) [ka] (Compound P-4, Table T1) Step A: Preparation of 2-(1-methylpyrazol-4-yl)propanenitrile [ka] A solution of 2-(1-methyl-1h-pyrazol-4-yl)acetonitrile (6.0 g, 47 mmol) in THF (71 mL) under argon was cooled to -78°C and treated dropwise with n-butyllithium (2.5 M in hexanes, 19 mL, 47 mmol). The resulting light brown suspension was stirred at this temperature for 10 min, after which iodomethane (3.0 mL, 47 mmol) was added. The reaction mixture was stirred from -78°C to room temperature for 1 h. The reaction mixture was quenched slowly with water and the solution was extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by CombiFlash chromatography using cyclohexane / AcOEt as eluent afforded 2-(1-methylpyrazol-4-yl)propanenitrile as a yellow liquid. LC-MS (Method A): 136[M+H], retention time: 0.45 min.

[0338] Step B: Preparation of 2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propanenitrile [ka] A solution of 2-(1-methylpyrazol-4-yl)propanenitrile (0.30 g, 2.22 mmol) in THF (9 mL) under argon was cooled to -78°C and treated dropwise with n-butyllithium (2.5 M in hexanes, 0.89 mL, 2.22 mmol). The resulting light brown suspension was stirred at this temperature for 10 min before 2,4-dichlorothiazole (0.34 g, 2.22 mmol) was added. The resulting suspension was stirred at -78°C for 5 min, allowed to reach room temperature and stirred under argon for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using ethyl acetate and cyclohexane as eluents. The title compound was obtained and used directly in the next step. LC-MS (Method A): 253 [M+H], retention time: 0.81 min.1 H NMR (400MHz, CDCl3) δ ppm 2.18 (s, 3H) 3.94 (s, 3H) 7.11 (s, 1H) 7.56 (d, J = 3.63Hz, 2H).

[0339] Step C: Preparation of 2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine [ka] To a solution of 2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propanenitrile (0.420 g, 1.66 mmol) and cobalt dichloride (0.220 g, 1.66 mmol) in methanol (5.54 mL) at 0° C., sodium borohydride (0.16 g, 4.15 mmol) was added in small portions. Immediate formation of a black precipitate was observed and the mixture was stirred at 0° C. for 1 h. LC-MS indicated consumption of starting material. 1N HCl was added until the pH was 3-4 and the mixture was extracted three times with ethyl acetate to remove impurities. The pH was then adjusted to 10 with 2N NaOH and the mixture was extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine as a colorless oil, which was used in the next step without further purification. LC-MS (Method A): 257 [M+H], retention time: 0.42 min.

[0340] Step D: Preparation of N-[2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (compound P-4, Table T1) A one-necked round-bottom flask equipped with a magnetic stirrer was charged with 2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine (0.1 g, 0.4 mmol), ethyl acetate (3 mL, 3 mL, 30.7 mmol), N,N-diisopropylethylamine (0.2 mL, 1.0 mmol) and 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid (0.1 g, 0.4 mmol). Propylphosphonic anhydride (T3P, 0.7 mL, 1.0 mmol) was then added dropwise at room temperature and the mixture was stirred at this temperature for 60 min. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography using a gradient of cyclohexane and ethyl acetate as eluent to give N-[2-(4-chlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide as a colorless oil. LC-MS (Method A): 464[M+H] Retention time: 1.05 min.

[0341] The racemic mixture was separated into its single isomers. SFC Chromatography (Analytical Method: SFC: Waters Acquity UPC / QDa, PDA Detector Waters Acquity UPC. Column: Daicel SFC CHIRALPAK® OZ, 3 μm, 0.3 cm×10 cm, 40° C. Mobile Phase: A:CO2 B:MeOH Isocratic: 4.8 min at 15% B, ABPR: 1800 psi, Flow Rate: 2.0 ml / min. Detection: 255 nm. Sample Concentration: 1 mg / mL in CAN. Injection: 1 μL): Peak 1: 2.54 min; 50.1% (isomer A) Peak 2: 2.94 min; 49.9% (isomer B) Preparative SFC method: Sepiatec Prep SFC 100 Column: Daicel CHIRALPAK® OZ, 5 mm, 2.0 cm x 25 cm Mobile phase: A:CO2 B:MeOH Isocratic:15%B Back pressure: 150 bar Flow rate: 60ml / min GLS Pump:- Detection: UV255nm Sample concentration: 100mg in 7ml MeOH Injection: 500μl Peak 1 (Isomer A, Compound P-5, Table T1) Retention time (min) approx. 2.56 Chemical purity (area % at 255 nm) >99 Enantiomeric excess (%)>99.5 Peak 2 (Isomer B, Compound P-6, Table T1) Retention time (min) approx. 2.96 Chemical purity (area % at 255 nm) >99 Enantiomeric excess (%)>96.1

[0342] Example P3: Preparation of 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propyl]isoxazole-3-carboxamide (compound P-2, Table T1) [ka] (Compound P-2, Table T1) Step A: Preparation of 2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propanenitrile [ka] A solution of 2-(1-methylpyrazol-4-yl)propanenitrile (0.30 g, 2.22 mmol, prepared as described in Example 2, Step A) in THF (9 mL) under argon was cooled to −78° C. and n-butyllithium (2.5 M in hexanes, 0.89 mL, 2.22 mmol) was added dropwise. The resulting light brown suspension was stirred at this temperature for 10 min before 2-chlorothiazole (0.27 g, 2.22 mmol) was added. The resulting suspension was stirred at −78° C. for 5 min, allowed to reach room temperature and stirred under argon for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate (×3). The combined organic layers were washed once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using ethyl acetate and cyclohexane as eluents to give the title compound. LC-MS (Method A): 219 [M+H], retention time: 0.68 min.

[0343] Step B: Preparation of 2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propan-1-amine [ka] To a solution of 2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propanenitrile (0.27 g, 1.24 mmol) and cobalt dichloride (0.16 g, 1.24 mmol) in methanol (4 mL) at 0° C., sodium borohydride (0.12 g, 3.09 mmol) was added in small portions. Immediate formation of a black precipitate was observed and the mixture was stirred at 0° C. for 1 h. LC-MS indicated consumption of starting material. 1N HCl was added until the pH was 3-4 and the mixture was extracted three times with ethyl acetate to remove impurities. The pH was then adjusted to 10 with 2N NaOH and the mixture was extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propan-1-amine as a colorless oil, which was used in the next step without further purification. LC-MS (Method A): 223 [M+H], retention time: 0.24 min.

[0344] Step C: Preparation of 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propyl]isoxazole-3-carboxamide (compound P-2, Table T1) [ka] (Compound P-2, Table T1) Prepared similarly to the method described in Example 2, step D. This gave 5-(2,4-difluorophenyl)-N-[2-(1-methylpyrazol-4-yl)-2-thiazol-2-yl-propyl]isoxazole-3-carboxamide as a colorless oil. LC-MS (Method A): 430[M+H]+; Retention time: 0.99 min.

[0345] Example P4: Preparation of N-[2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (compound P-3, Table T1) [ka] (Compound P-3, Table T1) Step A: Preparation of 2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propanenitrile [ka] 2-(1-Methylpyrazol-4-yl)propanenitrile (0.40 g, 2.96 mmol, prepared as described in Example 2, Step A) was dissolved in THF (11.8 mL) under argon to give a pale yellow solution. This was cooled to -78°C and then treated dropwise with n-butyllithium (2.5 M in hexanes, 1.2 mL, 2.96 mmol). The resulting pale brown suspension was stirred at this temperature for 10 min before 2,4,5-trichlorothiazole (0.56 g, 2.96 mmol) was added. The resulting suspension was stirred at -78°C for 5 min, allowed to warm to room temperature and stirred under argon for 30 min. The reaction mixture was then poured into water and extracted with ethyl acetate (x3). The combined organic layers were washed once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using ethyl acetate and cyclohexane as eluents to give 2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propanenitrile, which was used directly in the next step. LC-MS (Method A): 287 [M+H], retention time: 0.95 min.

[0346] Step B: Preparation of 2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propan-1-amine [ka] Prepared similarly to the method described in Example 3, step B to give the title compound as a colorless oil, which was used in the next step without further purification. LC-MS (Method A): 291 [M+H], retention time: 0.58 min.

[0347] Step C: Preparation of N-[2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (compound P-3, Table T1) [ka] (Compound P-3, Table T1) Prepared similarly to the method described in Example 2, step D. Purification by reversed-phase FC gave N-[2-(4,5-dichlorothiazol-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide as a brownish oil. LC-MS (Method A): 498 [M+H], retention time: 1.14 min. 1 H NMR(400MHz,CDCl3)δ ppm 1.80(s,3H)3.92(s,3H)4.07(d,J=6.54Hz,2H)6.96-7.08(m,2H)7.09(d,J=3.63Hz,1H)7.39(s,1H)7.48(s,1H)7.53(br t,J=6.18Hz,1H)7.95(td,J=8.54,6.18Hz,1H).

[0348] Further examples of compounds that have been synthesised are shown in Table T1.

[0349] [Table 5-1] [Table 5-2] [Table 5-3]

[0350] Biological Examples Example B-1: Alternaria solani / Tomato / Leaf disc (summer blight) Tomato leaf discs (cv. Baby) are placed on agar in multi-well plates (24-well type) and sprayed with the formulated test compounds diluted in water. The leaves are inoculated with a fungal spore suspension 2 days after application. The inoculated leaves are incubated in a climate cabinet at 23°C / 21°C (day / night) and 80% rh under a 12 / 12 h (light / dark) light regime and the efficacy of the compounds is evaluated as the percentage disease control compared to untreated test leaf discs (5-7 days after application) when an appropriate level of disease damage has developed on untreated test leaf discs.

[0351] The following compounds provided at least 80% control of Alternaria solani at 200 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-1, P-2, P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0352] Example B-2: Botryotinia fuckeliana (Botrytis cinerea) / Liquid culture (grey mold) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (Vogels liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application.

[0353] The following compounds provided at least 80% control of Botryotinia fuckeliana at 20 ppm when compared to untreated controls, which showed widespread disease development under identical conditions: P-2, P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0354] Example B-3: Glomerella lagenarium (Colletotrichum lagenarium) / Liquid Culture (Anthracnose) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato dextrose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application.

[0355] The following compounds provided at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11

[0356] Example B-4: Blumeria graminis f.sp. tritici (Erysiphe graminis f.sp. tritici) / Wheat / Leaf disc preventative (powdery mildew in wheat) Wheat leaf segments (cv. Kanzler) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. One day after application, the leaf segments are inoculated with powdery mildew-infected plants by shaking them over the test plates. The inoculated leaf segments are incubated in a climate chamber at 20°C and 60% rh under a light regime of 24 hours darkness followed by 12 hours light / 12 hours darkness, and the efficacy of the compounds is evaluated as the percentage of disease control compared to untreated when an appropriate level of disease damage appears on the untreated test leaf segments (6-8 days after application).

[0357] The following compounds provided at least 80% control of Blumeria graminis f.sp. tritici at 200 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-1, P-4, P-5, P-6, P-9, P-10

[0358] Example B-5: Fusarium culmorum / Liquid culture (Blight) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato glucose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application.

[0359] The following compounds provided at least 80% control of Fusarium culmorum at 20 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0360] Example B-6: Phaeosphaeria nodorum (Septoria nodorum) / Wheat / Leaf septorium preventive (Septoria nodorum) Wheat leaf segments (cv. Kanzler) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaves are inoculated with a fungal spore suspension 2 days after application. The inoculated test leaf segments are incubated in a climate cabinet under a 12-h light / 12-h dark light regime at 20°C and 75% rh, and the efficacy of the compounds is evaluated as the percentage disease control compared to untreated when an appropriate level of disease damage appears on the untreated test leaf segments (5-7 days after application).

[0361] The following compounds provided at least 80% control of Phaeosphaeria nodorum at 200 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-2, P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0362] Example B-7: Monographella nivalis (Microdochium nivale) / Liquid culture (Root rot of cereals) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato glucose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 4-5 days after application.

[0363] The following compounds provided at least 80% control of Monographella nivalis at 20 ppm when compared to untreated controls, which showed widespread disease development under identical conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11

[0364] Example B-8: Mycosphaerella arachidis (Cercospora arachidicola) / Liquid Culture (Early Spot Disease) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato glucose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 4-5 days after application.

[0365] The following compounds provided at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated controls which showed extensive disease development under identical conditions: P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0366] Example B-9: Magnaporthe grisea (Pyricularia oryzae) / Rice / Leaf Scab Preventive (Rice Blast) Rice leaf segments (cv. Ballila) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf segments are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf segments are incubated in a climate cabinet at 22°C and 80% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness, and the efficacy of the compounds is evaluated as the percentage disease control compared to the untreated when an appropriate level of disease damage appears on the untreated test leaf segments (5-7 days after application).

[0367] The following compounds provided at least 80% control of Magnaporthe grisea at 200 ppm when compared to untreated controls, which showed extensive disease development under identical conditions: P-1

[0368] Example B-10: Pyrenophora teres / Barley / Leaf-plate preventative (Net blotch) Barley leaf segments (cv. Hasso) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf segments are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf segments are incubated in a climate cabinet at 20°C and 65% rh under a 12-h light / 12-h dark photoperiod and the efficacy of the compound is assessed as disease control compared to untreated when an appropriate level of disease damage appears on the untreated test leaf segments (5-7 days after application).

[0369] The following compounds provided at least 80% control of Pyrenophora teres at 200 ppm when compared to untreated controls, which showed widespread disease development under identical conditions: P-1, P-2, P-4, P-5, P-6, P-8, P-9, P-10, P-11

[0370] Example B-11: Sclerotinia sclerotiorum / Liquid culture (sclerotinia rot) Mycelium fragments from freshly grown liquid cultures of the fungus are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of the nutrient broth containing the fungal material. The test plates are incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application.

[0371] The following compounds provided at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared to untreated controls, which showed widespread disease development under identical conditions: P-4, P-8, P-9, P-10

[0372] Example B-12: Wheat leaf spot fungus (Mycosphaerella graminicola) (Septoria tritici) / Liquid culture (leaf spot) Fungal conidia stored at low temperature are mixed directly into nutrient liquid medium (PDB potato glucose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and the inhibition of growth is measured photometrically 4-5 days after application.

[0373] The following compounds provided at least 80% control of Mycosphaerella graminicola at 20 ppm when compared to untreated controls that showed widespread disease development under identical conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11

Claims

1. Compounds of formula (I): 【Chemistry 1】 (In the formula, R 1 is hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl and C 3 ~C 6 cycloalkyl; R 2 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkylcarbonyl, N—C 1 ~C 4 Alkoxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 Alkyl-carbonimidoyl and C 1 ~C 4 alkoxycarbonyl; R 3 is hydrogen, halogen and C 1 ~C 4 selected from the group consisting of alkyl; R 4 is hydrogen, halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Alkylcarbonyl, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 Alkylaminocarbonyl and di(C 1 ~C 4 alkylamino)carbonyl; R 5 and R 6 is hydrogen and C 1 ~C 4 independently selected from the group consisting of alkyl; A 1 , A 2 and A 3 is CR 7 , N, N.R. 8 , O and S, with the proviso that A 1 , A 2 and A 3 is selected from N, O and S, and A 1 , A 2 and A 3 There is only one O or S in R 7 and R 8 is hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl and C 2 ~C 4 independently selected from the group consisting of alkynyl; Q 1 , Q 2 and Q 3 is CR 9 , N, N.R. 10 , O, and S, with the proviso that Q 1 , Q 2 and Q 3 At least one of N, NR 10 , O and S, and Q 1 , Q 2 and Q 3 Of which NR 10 , there is only one O or S; R 9 and R 10 is hydrogen, halogen, cyano, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl and C 2 ~C 4 alkynyl; and Z 1 is C 1 ~C 4 Alkyl, phenyl, 5- or 6-membered heteroaryl and C 3 ~C 6 cycloalkyl, wherein said 5- or 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S; and said phenyl, 5- or 6-membered heteroaryl, and C 3 ~C 6 Any of the cycloalkyls may be halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl and C 2 ~C 4 and optionally substituted with 1, 2, or 3 substituents independently selected from alkynyl. or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

2. R 1 2. The compound of formula (I) according to claim 1, wherein is methyl, ethyl or isopropyl.

3. R 2 2. The compound of formula (I) according to claim 1, wherein is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

4. R 3 2. The compound of formula (I) according to claim 1, wherein is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

5. R 4 2. The compound of formula (I) according to claim 1, wherein is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl and cyano.

6. R 5 and R 6 2. The compound of formula (I) according to claim 1, wherein is independently selected from the group consisting of hydrogen, methyl and ethyl.

7. A 1 , A 2 and A 3 But, CR 7 , N, O and S, with the proviso that A 1 , A 2 and A 3 is selected from N, O and S, and A 1 , A 2 and A 3 2. A compound of formula (I) according to claim 1, wherein there is only one O or S in

8. R 7 2. The compound of formula (I) according to claim 1, wherein is hydrogen or methyl.

9. Q 1 , Q 2 and Q 3 But, CR 9 , N, N.R. 10 and S, with the proviso that Q 1 , Q 2 and Q 3 At least one of N, NR 10 and S, and Q 1 , Q 2 and Q 3 Of which NR 10 or S is only one.

10. Z 1 is selected from methyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylphenyl, 2-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-fluoro-2-methoxy-phenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 2,4,6-trifluorophenyl, 3,5-difluoro-2-pyridyl, 2-furyl, 2-thienyl, 3-thienyl and 1-methylpyrazol-4-yl.

11. An intermediate compound of formula (III) or a salt thereof: 【Chemistry 2】 (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q 1 , Q 2 and Q 3 corresponds to the same definition as for the compounds of formula (I) according to any one of claims 1 to 8).

12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 10.

13. 13. The agrochemical composition of 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 damage to useful plants caused by plant pathogenic microorganisms, comprising applying a fungicidally effective amount of the compound of formula (I) according to any one of claims 1 to 10, or a composition containing the compound of formula (I), to the plant, a part thereof, or a habitat thereof.

15. Use of the compound according to any one of claims 1 to 10 as a bactericide / fungicide.

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