Microbicidal thiazole derivatives

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1 are disclosed which are useful as pesticides, and especially fungicides.

Description

[0001] The present invention relates to microbicidal thiazole derivatives, for example as active ingredients, which have microbicidal activity, in particular fungicidal activity. The present invention also relates to the preparation of these thiazole derivatives, to an agrochemical composition comprising at least one of the thiazole derivatives, and to the use of the thiazole derivatives or their compositions in agriculture or horticulture for controlling or preventing plants, harvested food crops, seeds or non-living materials from being infected by phytopathogenic microorganisms, preferably fungi.

[0002] WO 2010 / 012793 and WO 2017 / 207362 describe thiazole derivatives as pesticides.

[0003] According to the present invention, there is provided a compound having formula (I):

[0004]

[0005] in

[0006] Y is CF, CH or N;

[0007] R 1 is hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, or HC(O)NH-;

[0008] R 2 is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by R, phenyl, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 to 3 groups represented by R 3 substituted with a group represented by ), heteroaryl, heteroarylC1-C2alkyl, wherein the heteroaryl is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclylC1-C2alkyl, wherein the heterocyclyl is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5-membered to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing 1, 2, 3, 4 or 5 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein each of the spirocyclic carbobicyclic or carbotricyclic ring systems is optionally bonded to the remainder of the molecule through a C1-C2alkylene linker;

[0009] R 3 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C3-C8 cycloalkyl, or C3-C8 cycloalkylC1-C2 alkyl;

[0010] X is N or CH;

[0011] or a salt or N-oxide thereof.

[0012] Surprisingly, it has been found that novel compounds of formula (I) have a very advantageous level of biological activity for practical purposes for protecting plants against diseases caused by fungi.

[0013] Furthermore, it has been found that novel compounds of formula (I) having the following characteristics can show improved solubility properties (especially in non-polar solvents) and / or photostability properties when compared to their corresponding free amines (i.e., wherein the nitrile group on the nitrogen is replaced by hydrogen, as known, for example, from WO 2017 / 207362).

[0014] According to a second aspect of the present invention, there is provided an agrochemical composition comprising a fungicidal effective amount of a compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0015] According to a third aspect of the present invention, there is provided a method for controlling or preventing infection of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) or a composition comprising such a compound as an active ingredient is applied to the plant, its part or its locus.

[0016] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) as a fungicide. According to this particular aspect of the present invention, the use may or may not include a method of treating the human or animal body by surgery or therapy.

[0017] When substituents are indicated as being "optionally substituted", this means that they may or may not carry one or more identical or different substituents, for example one, two or three R 3 Substituents. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens may include, but are not limited to -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2 or 3 halogens may include, but are not limited to CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.

[0018] As used herein, the term "cyano" refers to a -CN group.

[0019] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iodo).

[0020] As used herein, the term "C1-C8 alkyl" refers to a straight or branched hydrocarbon chain group consisting only of carbon atoms and hydrogen atoms, which contains no unsaturation, has from one to eight carbon atoms, and is attached to the remainder of the molecule by a single bond. The terms "C1-C6 alkyl", "C1-C4 alkyl" and "C1-C3 alkyl" should be interpreted accordingly. Examples of C1-C8 alkyls include, but are not limited to, methyl, ethyl, n-propyl and isomers thereof, such as isopropyl. A "C1-C6 alkylene" group refers to the corresponding definition of a C1-C6 alkyl, except that such a group is attached to the remainder of the molecule by two single bonds. The term "C1-C2 alkylene" should be interpreted accordingly. Examples of C1-C6 alkylenes include, but are not limited to -CH2-, -CH2CH2- and -(CH2)3-.

[0021] As used herein, the term "C1-C8 haloalkyl" refers to a C1-C8 alkyl group as generally defined above, which is substituted with one or more halogen atoms, which may be the same or different. Examples of C1-C8 haloalkyl include, but are not limited to, trifluoromethyl.

[0022] As used herein, the term "C1-C8 alkoxy" refers to a group having the formula -OR a A group in which R a is a C1-C8 alkyl group as generally defined above. The terms "C1-C6 alkoxy", "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted accordingly. Examples of C1-C8 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

[0023] As used herein, the term "C3-C6 cycloalkyl" refers to a group belonging to a monocyclic saturated ring system and comprising 3 to 6 carbon atoms. The term "C3-C4 cycloalkyl" should be interpreted accordingly. Examples of C3-C6 cycloalkyl include, but are not limited to, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 1,1-dimethylcyclobutyl, 2-methylcyclobutyl, and 2,2-dimethylcyclobutyl.

[0024] As used herein, the term "C3-C6 cycloalkylC1-C2 alkyl" refers to a C3-C6 cycloalkyl ring attached to the remainder of the molecule via a C1-C2 alkylene linker as defined above.

[0025] As used herein, the term "phenyl C1-C2 alkyl" refers to a benzene ring attached to the remainder of the molecule via a C1-C2 alkylene linker as defined above. Examples of phenyl C1-C2 alkyl include, but are not limited to, benzyl and 1-phenylethyl.

[0026] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic group containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl or pyridyl.

[0027] As used herein, the term "heteroaryl C1-C2 alkyl" refers to a heteroaryl ring attached to the remainder of the molecule via a C1-C2 alkylene linker as defined above.

[0028] As used herein, the term "heterocyclic radical" refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms, wherein the heteroatoms are individually selected from nitrogen, oxygen and sulfur. The heterocyclic radical group can be bonded to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocyclic radicals include, but are not limited to, aziridine, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl.

[0029] As used herein, the term "heterocyclyl C1-C2 alkyl" refers to a heterocyclyl ring attached to the remainder of the molecule via a C1-C2 alkylene linker as defined above.

[0030] As used herein, a "spirocyclic carbobicyclic or carbotricyclic ring" is a non-aromatic bicyclic ring system comprising two rings joined together at one carbon atom, i.e., sharing one carbon atom. Examples of spirocyclic carbobicyclic or carbotricyclic ring systems include, but are not limited to, spiro[3.3]heptyl, spiro[3.4]octanyl, spiro[4.5]decyl, spiro[cyclobutane-1,2'-indanyl], or spiro[cyclopentane-1,2'-tetrahydronaphthyl].

[0031] The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compound can exist in optical isomeric forms (i.e., enantiomeric or diastereomeric forms). As a result of restricted rotation around a single bond, atropisomers may also exist. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof of compounds of formula (I). Similarly, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of compounds of formula (I).

[0032] In each case, the compounds of formula (I) according to the invention are in free form, oxidized form (such as N-oxides) or salt form (for example agronomically usable salt forms).

[0033] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, by A. Albini and S. Pietra in the book "Heterocyclic N-oxides", CRC Press, Boca Raton (1991).

[0034] The following list provides information on the substituents R of compounds having formula (I): 1 , R 2 , R 3 , X and Y, including preferred definitions. For any of these substituents, any definition given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0035] Y is CF, CH or N. In one embodiment, Y is CF. In another embodiment, Y is CH. In another embodiment, Y is N.

[0036] R 1 is hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, or HC(O)NH-. Preferably, R 1 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, or HC(O)NH-, more preferably halogen, C1-C2 alkyl, C1-C2 alkoxy, or HC(O)NH-. Even more preferably, R 1 is chloro, bromo, methyl, methoxy, or HC(O)NH-. Still more preferably, R 1 It is methyl or HC(O)NH-, and most preferably methyl.

[0037] R 2is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by R, phenyl, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 to 3 groups represented by R 3 substituted with a group represented by ), heteroaryl, heteroarylC1-C2alkyl, wherein the heteroaryl is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclylC1-C2alkyl, wherein the heterocyclyl is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5-membered to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing 1, 2, 3, 4 or 5 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the spirocyclic carbobicyclic or carbotricyclic ring system is each optionally bonded to the remainder of the molecule through a C1-C2alkylene linker.

[0038] Preferably, R 2 is C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by R, phenyl, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 to 3 groups represented by R 3 substituted with a group represented by ), heteroaryl, heteroarylC1-C2alkyl, wherein the heteroaryl is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclylC1-C2alkyl, wherein the heterocyclyl is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5-membered to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the spirocyclic carbobicyclic or carbotricyclic ring system is each optionally bonded to the remainder of the molecule through a C1-C2alkylene linker.

[0039] More preferably, R 2 is C1-C6 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by R, phenyl, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 to 3 groups represented by R 3substituted with a group represented by ), heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing a single heteroatom selected from nitrogen, oxygen and sulfur.

[0040] Even more preferably, R 2 is C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by R, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 or 2 groups represented by R 3 substituted with a group represented by ), or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system.

[0041] Still more preferably, R 2 is C1-C6 alkyl, C3-C5 cycloalkyl, C3-C5 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by R, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 or 2 groups represented by R 3 substituted with a group represented by ), or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system.

[0042] Even more preferably, R 2 is n-butyl, isobutyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, n-hexyl, 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, 1-methylcyclopentyl, benzyl, 1-phenylethyl, 3,5-bis(trifluoromethyl)benzyl, spiro[3.3]heptyl, spiro[3.4]octyl or spiro[cyclobutane-1,2′-indanyl], and most preferably 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, spiro[3.3]heptane-3-yl, spiro[3.4]octane-3-yl or spiro[cyclobutane-1,2′-indan]-1-yl.

[0043] In one set of embodiments, R 2 is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3substituted with a group represented by ), phenyl, phenyl C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, wherein the heteroaryl is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclyl C1-C2 alkyl, wherein the heterocyclyl is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5-membered to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing 1, 2, 3, 4 or 5 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the spirocyclic carbobicyclic or carbotricyclic ring system is each optionally bonded to the remainder of the molecule through a C1-C2 alkylene linker.

[0044] Preferably, R 2 is C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by ), phenyl, heteroaryl, heteroarylC1-C2alkyl, wherein the heteroaryl is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclylC1-C2alkyl, wherein the heterocyclyl is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5-membered to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the spirocyclic carbobicyclic or carbotricyclic ring system is each optionally bonded to the remainder of the molecule through a C1-C2alkylene linker.

[0045] More preferably, R 2 is C1-C4 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a radical represented by ), phenyl, heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing a single heteroatom selected from nitrogen, oxygen and sulfur.

[0046] Even more preferably, R 2 is C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by ), or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system.

[0047] Still more preferably, R 2 is C3-C4 cycloalkyl, C3-C4 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by ), or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system.

[0048] Even more preferably, R 2 It is 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, spiro[3.3]heptyl, spiro[3.4]octyl or spiro[cyclobutane-1,2′-indanyl], and most preferably 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, spiro[3.3]heptane-3-yl, spiro[3.4]octane-3-yl or spiro[cyclobutane-1,2′-indan]-1-yl.

[0049] R 3 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C3-C8 cycloalkyl, or C3-C8 cycloalkylC1-C2 alkyl. Preferably, R 3 is halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, C3-C6 cycloalkyl or C3-C6 cycloalkylC1-C2 alkyl, more preferably halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or C3-C6 cycloalkylC1-C2 alkyl. Even more preferably, R 3 is C1-C3 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkylC1-C2 alkyl. Still more preferably, R 3 is methyl, ethyl, isopropyl, trifluoromethyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl or cyclobutylethyl, and most preferably, R 3 It is methyl, trifluoromethyl or cyclopropylmethyl.

[0050] In one set of embodiments, R 3 is C1-C3 alkyl or C3-C6 cycloalkylC1-C2 alkyl. Preferably, R 3 is methyl, ethyl, isopropyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl or cyclobutylethyl, and more preferably, R 3 It is methyl or cyclopropylmethyl.

[0051] X is N or CH. In one embodiment, X is N. In another embodiment, X is CH.

[0052] Among the compounds of formula (I) according to the present invention, preferably:

[0053] R1 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, or HC(O)NH-;

[0054] R 2 is C1-C6 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a group represented by R, phenyl, phenyl C1-C2 alkyl (wherein the phenyl ring is optionally substituted with 1 to 3 groups represented by R 3 substituted with a group represented by ), heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing a single heteroatom selected from nitrogen, oxygen and sulfur;

[0055] R 3 is C1-C3 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkylC1-C2 alkyl;

[0056] X is N or CH; and

[0057] Y is CF, CH or N.

[0058] More preferably, R 1 is methyl or HC(O)NH-;

[0059] R 2 is C1-C6 alkyl, C3-C5 cycloalkyl, C3-C5 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by R, phenyl C1-C2 alkyl, wherein the phenyl ring is optionally substituted with 1 or 2 groups represented by R 3 The group represented is substituted, or is a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system;

[0060] R 3 is C1-C3 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkylC1-C2 alkyl;

[0061] X is N or CH; and

[0062] Y is CF, CH or N.

[0063] Even more preferably, R 1 is methyl or HC(O)NH-;

[0064] R2 is n-butyl, isobutyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, n-hexyl, 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, 1-methylcyclopentyl, benzyl, 1-phenylethyl, 3,5-bis(trifluoromethyl)benzyl, spiro[3.3]heptyl, spiro[3.4]octyl or spiro[cyclobutane-1,2'-indanyl];

[0065] X is N or CH; and

[0066] Y is CF, CH or N.

[0067] In another preferred embodiment, in the compounds of formula (I) according to the present invention, preferably:

[0068] R 1 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, or HC(O)NH-;

[0069] R 2 is C1-C4 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3 substituted with a radical represented by ), phenyl, heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing a single heteroatom selected from nitrogen, oxygen and sulfur;

[0070] R 3 is C1-C3 alkyl or C3-C6 cycloalkylC1-C2 alkyl;

[0071] X is N or CH; and

[0072] Y is CF, CH or N.

[0073] More preferably, R 1 is halogen, C1-C2 alkyl, C1-C2 alkoxy or HC(O)NH-;

[0074] R 2 is C1-C4 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 to 3 R 3substituted with a radical represented by ), phenyl, heteroaryl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, heterocyclyl, wherein the heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system optionally containing a single heteroatom selected from nitrogen, oxygen and sulfur;

[0075] R 3 is C1-C3 alkyl or C3-C6 cycloalkylC1-C2 alkyl;

[0076] X is N; and

[0077] Y is CF.

[0078] Even more preferably, R 1 is methyl or HC(O)NH-;

[0079] R 2 is C3-C4 cycloalkyl, C3-C4 cycloalkylC1-C2 alkyl (wherein the cycloalkyl is optionally replaced by 1 or 2 R 3 substituted with a group represented by ), or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system;

[0080] R 3 is methyl or cyclopropylmethyl;

[0081] X is N; and

[0082] Y is CF.

[0083] In a particularly preferred embodiment, the compound of formula (I) is:

[0084]

[0085]

[0086] In an even more preferred embodiment, the compound of formula (I) is 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-formamido-thiazole-4-carboxamide (1.b.25), 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-[[1-(cyclopropylmethyl)cyclopropyl]methyl]-5-methyl-thiazole-4-carboxamide (1.f.23), 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-[[1-(cyclopropylmethyl)cyclopropyl]methyl]-5-methyl-thiazole-4-carboxamide (1.f.24), 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3.3]heptane-3-yl-thiazole-4-carboxamide (1.e.23), 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[cyclobutane-2,2'-indan]-1-yl-thiazole-4-carboxamide (1.d.23), or 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (1.b.23).

[0087] The compounds of the present invention may be prepared as shown in the following schemes, wherein (unless otherwise stated) the definition of each variable is as defined above for compounds having formula (I).

[0088] According to the present invention, the compound having the formula (I) (wherein R 1 , R 2 , X and Y are as defined for formula (I)) can be obtained by heating a compound of formula (II) (wherein R 1 , R 2 , X and Y are as defined for formula (I)) and a compound of formula (III) wherein R 11 is halogen, preferably bromine). This is shown in Scheme 1 below.

[0089] Solution 1

[0090]

[0091] A compound having formula (II) (wherein R 1 , R 2 , X and Y are as defined for formula (I)) can be obtained by reacting a compound of formula (IV) (wherein X and Y are as defined for formula (I)) with a compound of formula (V) (wherein R 1 and R 2 is as defined for formula (I), and R 12is a halogen, preferably bromine). This is shown in Scheme 2 below.

[0092] Solution 2

[0093]

[0094] A compound having formula (V) (wherein R 1 and R 2 is as defined for formula (I), and R 12 is halogen, preferably bromine) can be obtained by reacting a compound of formula (VI) (wherein R 1 is as defined for formula (I), and R 12 is halogen, preferably bromine) and a compound of formula (VII) wherein R 2 The transformation is as defined for formula (I). This is shown in Scheme 3 below.

[0095] Solution 3

[0096]

[0097] A compound having formula (VI) (wherein R 1 is as defined for formula (I), and R 12 is halogen, preferably bromine) can be obtained by converting a compound of formula (VIII) (wherein R 1 is as defined for formula (I), R 12 is halogen, preferably bromine, and R 13 This is shown in Scheme 4 below.

[0098] Solution 4

[0099]

[0100] Alternatively, a compound of formula (II) wherein R 1 , R 2 , X and Y are as defined for formula (I)) can be obtained by reacting a compound of formula (IX) (wherein R 1 , X and Y are as defined for formula (I)) and a compound of formula (VII) wherein R 2 The transformation is as defined for formula (I). This is shown in Scheme 5 below.

[0101] Solution 5

[0102]

[0103] A compound having the formula (IX) (wherein R 1 , X and Y are as defined for formula (I)) can be obtained by converting a compound of formula (X) (wherein R 1 , X and Y are as defined for formula (I), and R 13 This is shown in Scheme 6 below.

[0104] Solution 6

[0105]

[0106] A compound having the formula (X) (wherein R 1 , X, and Y are as defined for formula (I), and R 13 is C1-C6 alkyl) can be obtained by reacting a compound of formula (IV) (wherein X and Y are as defined for formula (I)) with a compound of formula (VII) (wherein R 1 is as defined for formula (I), R 12 is halogen, preferably bromine, and R 13 This is shown in Scheme 7 below.

[0107] Solution 7

[0108]

[0109] Alternatively, a compound of formula (X) wherein R 1 , X and Y are as defined for formula (I), and R 13 is C1-C6 alkyl) can be obtained by reacting a compound of formula (XI) (wherein X and Y are as defined for formula (I), and R 12 is halogen, preferably bromine or iodine) and a compound of formula (XII) (wherein R 1 is as defined for formula (I), and R 13 This is shown in Scheme 8 below.

[0110] Solution 8

[0111]

[0112] Alternatively, a compound of formula (II) wherein R 1 , R 2 , X and Y are as defined for formula (I)) can be obtained by reacting a compound of formula (XI) (wherein X and Y are as defined for formula (I), and R 12 is halogen, preferably bromine or iodine) and a compound of formula (XIII) (wherein R 1 and R 2 The transformation is as defined for formula (I). This is shown in Scheme 9 below.

[0113] Solution 9

[0114]

[0115] Alternatively, the compound of formula (I) according to the present invention (wherein R 1 , R 2 , X and Y are as defined for formula (I)) can be obtained by reacting a compound of formula (V) (wherein R 1 and R 2 is as defined for formula (I), and R 12 is halogen, preferably bromine) is converted with a compound of formula (XIV) wherein X and Y are as defined for formula (I). This is shown in Scheme 10 below.

[0116] Solution 10

[0117]

[0118] Compounds of formula (XIV) wherein X and Y are as defined for formula (I) can be obtained by reacting a compound of formula (XV) wherein X and Y are as defined for formula (I) with a compound of formula (III) wherein R 11 is a halogen, preferably bromine). This is shown in Scheme 11 below.

[0119] Solution 11

[0120]

[0121] Surprisingly, it has now been found that novel compounds of formula (I) have a very advantageous level of biological activity for protecting plants against diseases caused by fungi for practical use.

[0122] Compounds of formula (I) can be used in the agricultural sector and related fields, as active ingredients such as for controlling plant pests, or on non-living materials for controlling spoilage microorganisms or potentially harmful organisms to humans. The novel compounds are characterized by excellent activity at low application rates, good plant tolerance and environmental friendliness. They have very useful therapeutic, preventive and systemic characteristics and can be used to protect numerous cultivated plants. Compounds of formula (I) can be used to suppress or destroy harmful organisms that occur on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different useful plant crops, while also protecting, for example, those plant parts that grow later from the infringement of phytopathogenic microorganisms.

[0123] The invention further relates to a method for controlling or preventing plants or plant propagation materials and / or harvested food crops susceptible to attack by microorganisms from infestation by treating the plants or plant propagation materials and / or harvested food crops, wherein an effective amount of a compound of formula (I) is applied to the plants, parts thereof or the locus thereof.

[0124] Compounds of formula (I) can also be used as fungicides. As used herein, the term "fungicide" means a compound that controls, modifies or prevents fungal growth. The term "fungicidal effective amount" means an amount of such a compound or a combination of such compounds that can have an effect on fungal growth. Controlling or modifying effects include all deviations from natural development, such as killing, retardation, etc., and prevention includes barriers or other defensive structures in or on plants that prevent fungal infection.

[0125] The compounds of formula (I) can also be used as seed dressings for treating plant propagation materials (e.g. seeds, such as fruits, tubers, or cereals), or plant cuttings (e.g. rice), for protection against fungal infections or phytopathogenic fungi in the soil. Propagation materials can be treated with compositions comprising compounds of formula (I) before planting: for example, seeds can be dressed before sowing.

[0126] The active ingredient according to the invention can also be applied to grains (coating) by dipping the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example to the furrow of the seed during sowing. The invention also relates to such a method for processing plant propagation material, and to the plant propagation material so processed.

[0127] Furthermore, the compounds according to the invention can be used for controlling fungi in related fields, such as, for example, in the protection of industrial materials (including wood and wood-related industrial products), in food storage, in hygiene management.

[0128] Additionally, the present invention can be used to protect non-living materials such as wood, siding and paint from fungal attack.

[0129] The compounds of formula (I) may be effective, for example, against fungi and fungal vectors of diseases and phytopathogenic bacteria and viruses. These fungi and fungal vectors of diseases and phytopathogenic bacteria and viruses are, for example:

[0130] Psoralea corylifolia, Alternaria species, Aphanomyces species, Ascochyta species, Aspergillus species (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terreus), Acetomyces species (including A. pullulans), Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botrytis species (including B. dothidea, B. obtusa), Botrytis species (including B. cinerea), Candida species (including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis), Cephalosarcina fragrans, Cercosporidium species, Cercospora species (including C.arachidicola), Cercosporidium personatum, Cladosporium species, Claviceps, Coccidioides immitis, Coccidioidomyces species, Colletotrichum species (including C.musae), Cryptococcus neoformans, Diaporthe species, Subsporus species, Endomyces species, Entomophthora species, Epidermophyton species, Erwinia amylovora, Powdery mildew species (including E. cichoracearum), Eutypa lata), Fusarium species (including Fusarium culmorum, Fusarium graminearum, F. langsethiae, Fusarium moniliforme, Fusarium gloeosporium, Fusarium solani, Fusarium oxysporum, Fusarium lamina), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium species, Camelusporangium species, Histoplasma species (including Histoplasma capsulatum (H.capsulatum), red thread pathogen, Leptographium lindbergi, Leveillulataurica, Lophodermium seditiosum, Microdochium nivale, Microsporum species, Streptoceras species, Mucor species, Mycosphaeria species (including Mycosphaeria graminicola and M. pomi), tree blight pathogen, spruce pathogen, Paracoccidioides species, Penicillium species (including Penicillium digitatum and Penicillium italicum), True mold species, Peronospora species (including Peronospora maize, Peronospora philippinarum and Peronospora kaoliang), Peronospora species, Septoria glume, Phellaria pachyrhizi, Phellinus igniarus, Phyllanthus species, Phoma species, Phomopsis grapevine viticola), Phytophthora species (including Phytophthora infestans), Plasmopara species (including Plasmopara hallii, P. viticola), Grifola species, Pseudocercosporella species (including P. leucotricha), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas species, Pseudocercosporella species (including Pseudocercosporella spp., Pseudocercosporella spp.), Pseudopeziza tracheiphila, Downy Mildew species (including barley rust (P.hordei), wheat leaf rust (P.recondita), stripe rust (P.Striiformis), wheat brown rust (P.triticina)), Sclerotinia species, Pyrocoel species, Pyrocoel species (including rice blast fungus (P.oryzae)), Pythium species (including ultimate Pythium), Columnar septa species, Rhizoctonia species, Rhizomucor pusillus, Rhizopus arrhizus, Rhizosporium species, Trichosporon species (including Scedosporium apiosporum and Scedosporium prolificum), coal spot disease (Schizothyrium pomi),.

[0131] Sclerotinia, Sclerotium, Septoria (including S. nodorum, S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola), Tilletia, Trichoderma (including T. harzianum), T. pseudokoningii, T. viride), Trichophyton, Pseudomonas, Uncinaria, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0132] In the context of the present invention, target crops and / or useful plants to be protected typically include perennial and annual crops, such as berry plants, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar beets and fodder beets, coffee beans, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, for example apples, apricots, avocados, bananas, cherries, citrus, nectarines, peaches, pears and plums; grasses, for example Bermuda grass, bluegrass, bentgrass, centipede grass, cow grass, etc. grass, ryegrass, St. Augustine grass, and zoysia grass; herbs such as basil, borage, chives, cilantro, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as beans, lentils, peas, and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm plants such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melon, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and vines such as grapes.

[0133] The term "useful plants" is to be understood as also including useful plants which have been rendered tolerant to herbicides such as bromoxynil or classes of herbicides such as, for example, HPPD inhibitors, ALS inhibitors such as primisulfuron, primisulfuron and trifloxysulfuron, EPSPS (5-enol-pyruvate-shikimate-3-phosphate-synthetase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional breeding methods or genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones such as imazamox by conventional breeding methods (mutagenesis) are Summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides or herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant corn varieties, which are and It is commercially available under the trademark ANTIQUID®.

[0134] The term "useful plants" is to be understood as also including useful plants which have been transformed by the use of recombinant DNA techniques in such a way that they are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular from the genus Bacillus.

[0135] Examples of such plants are: (corn variety expressing CryIA(b) toxin); YieldGard (corn variety expressing CryIIIB(b1) toxin); YieldGard (maize varieties expressing CryIA(b) and CryIIIB(b1) toxins); (corn variety expressing Cry9(c) toxin); Herculex (a corn variety expressing the CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate-ammonium); NuCOTN (cotton variety expressing CryIA(c) toxin); Bollgard (cotton variety expressing CryIA(c) toxin); Bollgard (cotton varieties expressing CryIA (c) and CryIIA (b) toxins); (cotton varieties expressing VIP toxin); (potato variety, expressing CryIIIA toxin); GT Advantage (GA21 glyphosate tolerance trait), CBAdvantage (Bt11 corn borer (CB) trait), RW (corn rootworm trait) and

[0136] The term "crops" is to be understood as also including crop plants which have been transformed by the use of recombinant DNA techniques such that they are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0137] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of nematode-parasitic bacteria, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophila, or Xenorhabdus spp. nematophilus); toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; lectins (agglutinin); protease inhibitors, such as trypsin inhibitor, silk proteinase inhibitor, potato glycoprotein, cystatin, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, corn-RIP, abrin, luffa seed protein, saporin or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0138] In the context of the present invention, delta-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3, or Vip3A) are understood to include, obviously, mixed toxins, truncated toxins, and modified toxins. Mixed toxins are recombinantly produced by new combinations of different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence is inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0139] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0140] Methods for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0141] The toxins contained in the transgenic plants render the plants tolerant to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0142] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (corn variety expressing Cry1Ab toxin); YieldGard (corn variety expressing Cry3Bb1 toxin); YieldGard (corn varieties expressing Cry1Ab and Cry3Bb1 toxins); (corn variety expressing Cry9C toxin); Herculex (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate-ammonium); NuCOTN (cotton variety expressing Cry1Ac toxin); Bollgard (cotton variety expressing Cry1Ac toxin); Bollgard (cotton varieties expressing Cry1Ac and Cry2Ab toxins); (cotton varieties expressing Vip3A and Cry1Ab toxins); (potato variety, expressing Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0143] Further examples of such genetically modified crops are:

[0144] 1. Bt11 corn, from Syngenta Seeds SAS, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, which has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 corn also transgenic expression of the PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0145] 2. Bt176 corn, from Syngenta Seeds, 27 Hobbit Road, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, which is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of the Cry1Ab toxin. Bt176 corn also transgenic expression of the enzyme PAT to obtain tolerance to the herbicide glufosinate ammonium.

[0146] 3. MIR604 corn, from Syngenta Seeds, 27 Rue Hobbitt, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Corn made insect-resistant by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03 / 018810.

[0147] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects.

[0148] 5. IPC 531 cotton, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0149] 6.1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate ammonium.

[0150] 7. NK603×MON 810 maize, from Monsanto Europe 270-272 Boulevard Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It is a conventionally bred hybrid maize variety made by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium sp. strain CP4 (making it tolerant to herbicides). (contains glyphosate), and also the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki (confers resistance to certain lepidopteran insects, including the European corn borer).

[0151] As used herein, the term "location" means a place where or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

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

[0153] The term "plant propagation material" should be understood as meaning the reproductive parts of a plant, such as seeds, which can be used for the propagation of a plant, and vegetative materials, such as cuttings or tubers (e.g., potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants can be mentioned. Germinated plants and young plants that will be transplanted after germination or after breaking the ground can also be mentioned. These young plants can be protected before transplanting by being treated completely or partially by dipping. Preferably, "plant propagation material" should be understood as meaning seeds.

[0154] The pesticides mentioned here using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0155] Compounds with formula (I) can be used in unmodified form, or preferably, together with conventional adjuvants used in the field of formulations. For this purpose, they can be conveniently formulated as emulsifiable concentrates, pastes that can be coated, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, particles and also encapsulations, for example in polymeric materials, in a known manner. For the type of composition, the application method is selected according to the intended purpose and the prevailing environment, such as spraying, atomizing, dusting, spreading, coating or pouring. The composition can also contain other adjuvants, such as stabilizers, defoamers, viscosity modifiers, adhesives or tackifiers, and fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0156] Suitable carriers and adjuvants (for example for agricultural use) can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersions, wetting agents, tackifiers, thickeners, adhesives or fertilizers. Such carriers are for example described in WO 97 / 33890.

[0157] The compounds of formula (I) are usually used in the form of compositions and can be applied to crop areas or plants to be treated simultaneously or sequentially with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective herbicides or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants that promote application that are commonly used in the field of formulations.

[0158] The compounds of formula (I) can be used in the form of fungicidal compositions for controlling or protecting against phytopathogenic microorganisms, said compositions comprising as active ingredient (in free form or in the form of agrochemically usable salts) at least one compound of formula (I) or at least one preferred individual compound as defined above, and at least one of the above-mentioned adjuvants.

[0159] The present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), 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, in addition to the compound of formula (I), the composition may also comprise at least one or more pesticidal active compounds, such as additional fungicidal active ingredients.

[0160] The compound of formula (I) can be the sole active ingredient of the composition, or it can be mixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) when appropriate. In some cases, the additional active ingredients can lead to unexpected synergistic activity.

[0161] Examples of suitable additional active ingredients include the following acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, arsenic-containing fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged biphenyl fungicides, carbamate fungicides, phenylcarbamate 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, organophosphorus fungicides, Organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfonamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline 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.

[0162] Examples of suitable additional active ingredients also include the following:

[0163] Petroleum, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenyl sulfone, acetothionil, aldicarb, sago, fruit manphos, amine dephosphite, ammonium dephosphite hydrogen oxalate, amitraz, cypermethrin, arsenic trioxide, azobenzene, azophos, benomyl, benoxafos, benzyl benzoate, bixafen, bromothion, bromothion, bromopyralid , buprofezin, butanone carbendazim, butanone sulfone carbendazim, butyl pyridaben, calcium polysulfide, octachlorocamphene, chlormethoxam, trithion, cyclobutrifluram, cypermethrin, cypermethrin, cypermethrin hydrochloride, cypermethrin, cypermethrin, dimethoate, chlorfenapyr, chlorfenapyr hydrochloride, chlorfenapyr, chlorfenapyr, ethyl chlorfenapyr, chlorfenapyr (chloromebuform), chlorfenapyr, propyl chlorfenapyr, chlorfenapyr, cypermethrin I, cypermethrin II, cypermethrin, closantel, coumaphos, crotamiton, baclofos, Thiazolin, chlorfenapyr, DCPM, DDT, dinex, dinex-O, dinex-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl, demeton-S-methyl, demeton-S-methyl, bacteriostatic, dichlorvos, dichlorvos, chlorfenapyr, chlorfenapyr, dinex, dinex-diclexine, dinex-4, dinex-6, lindane Mite-killing agent, nitropentyl ester, nitrooctyl ester acaricide, nitrobutyl ester, dimethoate, sulfodiphenyl, disulfiram, DNOC, dofenapyn, doramectin, indophos, eprinomectin, thiophos, ethidium, anti-mite azole, fenbutatin, fenthiocarb, fenpyrad, fenpyraclostrobin, aminophenazone, fentrifanil, flufenamid, flufenuron, diflunisal, flupentiofenox, FMC 1137, fenthion, fenthion hydrochloride, formparanate, γ-HCH, chloranil, benzyl chloranil, hexadecyl cyclopropane carboxylate, isothiocarb, jasmonate I, jasmonate II, iodine, lindane, propanil, cypermethrin, dithiophos, methylthiophene, cypermethrin, methyl bromide, cypermethrin, chloranil, milbemid, propylamine, monocrotophos, malathion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl-propyl)-5- [(6-iodo-3-pyridyl)methoxy]pyridazine-3-one, fluazifop, nikkomycin, pentocarb, pentocarb 1:1 zinc chloride complex, omethoate, isothiocarb, sulfone, pp'-DDT, parathion, permethrin, fenthion, phosalone, thiocyanate, phosphamidon, polychloroterpenes, polynactins, chloranil, cypermethrin, propoxur, ethidium, phosphamidon, pyrethrin I, pyrethrin II,Pyrethrins, pyridazinon, pyrimithiophos, quinalphos, quintiofos, R-1492, glyphosate, rotenone, octamethrin, clomar, selamectin, thion, SSI-121, sulfluramid, sulfotep, sulfur, flumethoxine, τ-fluvalinate, TEPP, tert-butylcarb, tetrachlorothiazide, thiafenox, thiafenox, long-acting carb, methyl thiocarb, chlorpyrifos, thiamethoxam, thiamethoxam, triazophos, zolylphos, trichloropropoxyphos, triacylglycerol, aphidicide, vaniliprole, perchlorate, copper dioctanoate, copper sulfate, cybutryne, dichloronaphthoquinone, dichlorophen, chlorpyrifos Polyacid, triphenyltin, slaked lime, sodium mansonate, algae quinone, quinone, simazine, triphenyltin acetate, triphenyltin hydroxide, livestock phosphorus, piperazine, thiophanate, chloralose, fenthion, pyridine-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxaline-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodesine, sodium sulfone, formaldehyde, mercury plus phenoxyacetate, kasugamycin, kasugamycin hydrochloride hydrate, nickel di(dimethyldithiocarbamate), trichloromethylpyridine, octhiothione, oxolinic acid, oxytetracycline, hydroxyquinoline potassium sulfate, thiabendazole, streptomycin, streptomycin sesquisulfate, chloranthracene, thimerosal, cotton brown banded moth GV, radiobacterium, Amblyseius species, Spodoptera exigua NPV, Protocera cerana, Short-spurred Aphid Wasp, Parasitic Wasp of Cotton Aphid, Aphid Midge, Spodoptera californica NPV, Bacillus sphaericus, Beauveria bassiana, Common Lacewings, Cryptolabia monteri, Codling Moth GV, Siberian Ichthyophthirius, Pea Leafminer, Aphid Wasp, Aphid Wasp, Bacteriotrophic Heterorhabditis elegans and Heterorhabditis magna , spotted long-legged ladybird, orange powder scale parasitic wasp, blind bug, cabbage armyworm NPV, yellow broad-handled jumping wasp, yellow green Metarhizium, small spore variant of Metarhizium anisopliae, European new pine sawfly NPV and red-headed new pine sawfly NPV, species of the genus Microseiidae, smoke-colored pseudo-Peikycetes roseus, Chilean small phytoseiid mite, hairy mosquito nematode, small tortoise moth nematode, noctuid Steinernema, Gricea nematode, sharp-sided Steinernema, Steinernemariobravis, mole cricket Steinernema, Steinernema species, Trichogramma species, western blind mite, Verticillium lecanii, oxazolidinone, bis(aziridine)methylaminophosphine sulfide, busulfan, dimethivin, hexamethylmelamine, hexamethylphosphine, methyl tibacterium, methyl thiotibacterium, methyloxazolidinone, infertile amine, thiocarbamide, hexamethylphosphine, thiotibacterium, trothamide, urea imine, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tridec-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)-eicos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodec-7,9-dien-1-yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnon-5-ol and 4-methylnon-5 -ketone, α-polystyrene, western pine beetle gathering pheromone, dodecadienol, kodemon, fly attractant, epoxy nonadecane, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8, 10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, southern pine beetle gathering pheromone, trap-killing ene mixture, trap-killing ene mixture I, trap-killing ene mixture II, trap-killing ene mixture III, trap-killing ene mixture IV, hexane attractant, tooth beetle dienol, small stupid enol, scarab sex attractant, trimethyl dioxytricyclononane, noctuid attractant (litlure), cabbage looper sex attractant, trap-killing ester, megatomoic acid (megatomoic acid acid), entrapped ether, entrapped ene, octadec-2,13-diene-1-yl acetate, octadec-3,13-diene-1-yl acetate, Hekangbi, coconut rhinoceros beetle aggregation pheromone, non-Lekang, entrapped ring, sordidin, fungi-eating methyl entrapped alcohol, tetradec-11-ene-1-yl acetate, Mediterranean fruit fly attractant, Mediterranean fruit fly attractant A, Mediterranean fruit fly attractant B1, Mediterranean fruit fly attractant B2, Mediterranean fruit fly attractant C, trunc-call, 2-(octylthio)-ethanol, diethyltoluene, butoxy (polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, DEET, mosquito repellent, dimethyl phthalate, ethyl hexanediol, hexyl urea, mequindine, methyl neodecylamide, oxamate , Picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-di(4-ethylphenyl)-ethane, 1,2-dichloropropane and 1,3-dichloropropylene, 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-imidazolidinone, 2-isovaleryl indan-1,3-dione,2-Methyl (prop-2-ynyl) aminophenyl methyl carbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yl dimethyl carbamate, 4-methyl (prop-2-ynyl) amino-3,5-xylyl methyl carbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate, acethion, acrylonitrile, aldrin, alloamicin, cypermethrin, α-decandrin, aluminum phosphide, cypermethrin, neonicotinoid, ethyl methidathion, methyl pyrifos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, cypermethrin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, pentacyclic bioethanomethrin, biopermethrin, bis(2-chloroethyl) ether, borax, bromophenazone, bromo-DDT, chlorpyrifos, chlordane, butathiofos, butyl phosphate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, chloran hydrochloride, cevadine, borneol, chlordane, chlordecone, chloroform, chloropicrin, chloraniloxime, chlorprazophos, cis-resmethrin, cismethrin, clocythrin, copper acetoarsenite, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, benzonitrile, cypermethrin, cypermethrin, d-methanthrin, DAEP, dazomethane, decarbofuran, chloranil, isochlor, chloranil, dicresyl, cypermethrin, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dior, tetrafluthrin, demicarb, pyrethrin, methyl chlorpyrifos, difenocarb, propanol, pentotropol, dinofuranoside, fenthion, vesiculophos, thiopyraphos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiobencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenthion, ethylbencarb, fenitrothion, fenoxacrim, cypermethrin, fenthion, ethylfenthion, flucofuron, butylfenthion, phosphonium arsenate, butylcyclothion, furathiocarb, pyrethroid, octylguanidine salt, octylguanidine acetate, tetrathiocarb Sodium chlorate, benzyl chlorpyrifos, HCH, HEOD, heptachlor, cypermethrin, HHDN, hydrogen cyanide, quinoline carbendazim, IPSP, chlorfenapyr, carbochlorin, isoaldrin, isofenphos, transplanting spirit, rice blast spirit, oxazophos, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorpentyl, methoprene, lead arsenate, bromophenylphos, acetamiprid, thiathion, m-isopropyl methyl carbamate, magnesium phosphide, phosphorus azide, methyl aphid, aphid, mercurous chloride,Methyl sulfoxide, metamex, metamex potassium salt, metamex sodium salt, methyl sulfonyl fluoride, butenamidophos, methoprene, methyl ether thiocyanate, methoxychlor, methyl isothiocyanate, methyl chloroform, dichloromethane, oxadiazine, anticide, naphthiophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, orthonicotine, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-yl phosphonothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphonothioate, O,O,O',O'-tetrapropyl dithiodipyrophosphate, oleic acid, p-dichlorobenzene, methyl parathion, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, fenthion, parachlorothion, phosphine, methyl phoxim, methamidophos, polychlorinated dicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocious element I, precocious element II, precocious element III, amidophos, profluthrin, fenthion, pyraclostrobin, anti-pyrethroid, quassia, quinalphos-methyl, fenthion, iodophos, resmethrin, rotenone, thiamethoxam, ryanodine, sabadilla, octamidine, clostridium, SI-0009, thiamethoxam, chlorpyrifos, Sodium arsenate, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenol, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, thiopromide, tar, thiamethoxam, TDE, butylpyrimidinphos, dimethoate, cyclopentylthrin, tetrachloroethane, thiochlorvos, cyclohexane, cyclohexane oxalate, cypermethrin, cypermethrin sodium, tralomethrin, permethrin, trichlormetaphos-3, toxic soil Phosphine, methoxycarb, trifluoromethoxycarb (tolprocarb), chlorpyrifos, methoprene, veratridine, veratridine, XMC, zetamethrin, zinc phosphide, tolfenphos, and chlorfluanid, tetrafluanid, bis(tributyltin) oxide, bromoacetamide, iron phosphate, niclosamide-ethanolamine, tributyltin oxide, pyrimorph, worm killer, 1,2-dibromo-3-chloropropane, 1,3-dichloropropylene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl- 6-thio-1,3,5-thiadiazine-3-ylacetic acid, 6-isopentenylaminopurine, phenylchlorothiol, cytokinin, DCIP, furfural, isoamidophos, kinetin, verrucospore mycorrhizal composition, tetrachlorothiophene, xylenol, zeatin, potassium ethyl xanthate, acibenzolar, acibenzolar-S-methyl, Polygonum cuspidatum extract, α-chloroalcohol, antu, barium carbonate, bimuramide, brodifacoum, bromodiolone, bromodiolone, chloranone, cholecalciferol, chloranthate, rat-killing naphthalene, rat-killing pyrimidine, rat-killing pyrimidine, thiocarb, dimethoate, dimethoate, calciferol, fludioxaline,Fluoroacetamide, flurfosidine, flurfosidine hydrochloride, warfarin, fosfos, phosphorus, warfarin, warfarin, scilla glycoside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, synergistic acetylene ether, MGK264, piperonyl butoxide, synergistic aldehyde, propyl isomer, S421, synergistic powder, sesame, sulfoxide, anthraquinone, copper cyclohexane, copper oxychloride, dicyclopentadiene, serene, zinc cyclohexane, zinc thiram, imanin, ribavirin, mercuric oxide, methyl thiophanate, azaconazole, bifenthrin, fuconazole, cyproconazole, difenoconazole, diniconazole, fluoxepiconazole, nitrobenzene, fluquinconazole, fluoxaponazole, fluorosilicone azole, flutriafol, furopyram, hexaconazole, imazalil, imidazole, imipenem, picolinamide, metconazole, myclobutrazol, paclobutrazol, rice blast ester, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyraclostrobin, simeconazole, tebuconazole, fluconazole, triadimefon, triadimenol, triflumazole, trimethirimol, chlorfenapyr, flufenapyr, bupirimate, dimethirimol, ethirimol, dodecacyclic morpholine, fenpropidine, fenpropimorph, spiroxaplanol, tridecamorph, cyprodinil, pyrimethanil, pyrimethanil anil), fenpyroxil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, furamide, oxadixyl, carbendazim, debacarb, thiabendazole, chlozolinate, dichlozoline, myclozoline, procymidone, vinclozoline, boscalid, carboxin, furamide, flutolanil, oxadixyl, penthiopyrad, oxycarboxin, and penthiopyrad. iopyrad), thiopyrad, doguodine, biguanide, azoxystrobin, ethersstrobin, enestroburin, enestroburin, flutoxanil, fluoxastrobin, ethersstrobin, fenoxystrobin, trifloxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, ferram, mancozeb, maneb, methanamide, methyl propineb, maneb, captazole, captan, azole, folic acid, tolylfluanid, Bordeaux mixture, copper oxide, mancozeb, quinoline copper, phthalocyanine, kefansan, isothiocyanate, chlorpyrifos, methyl tolclofos, captazole, benzylpyridin, blasticidin-S, chloroneb, chlorothalonil, cyfluthrin, cymoxanil,diclocymet, diclomezine, dicloran, diethofencarb, oxadiazine, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, fluopicolide, flusulfamide, flupyraclostrobin, fenacet, fosetyl-aluminum osetyl-aluminium), hymexazol, propineb, cyazofamid, methasulfocarb, mefenamic acid, pencycuron, phthalide, polyoxins, propamocarb, pyraclostrobin, proquinazid, pyroquilon, pyriofenone, quinoxyfen, pentachloronitrobenzene, thiazolamide, triazoxide, tricyclazole, triazine, validamycin, valeramide, zoxamide , mandipropamid, isopyrazam, sedaxane, benzovinflumizone, fluopyraclostrobin, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflurane, isothiocyanate, dipymetitrone, 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- 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, jiaxiangjunzhi, lvbenmixianan, dichlobentiazox, mandestrobin,3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]propan-2-ol, oxathiapiprolin, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamate, pyraziflumid, inpyrfluxam, trolprocarb, chlorfluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4- 1-[(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-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester, N-[[5-[4-(2,4- 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, pyrimidine Amine, indazole sulfazopyrazone, fluopicolide, (Z,2E)-5-[1-(4-chlorophenyl) pyrazol-3-yl] oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine, florylpicoxamid, fenpicoxamid, isobutylethoxyquinoline, ipflufenoquin, quinofumelin, isoprothiocarbamide, 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, benzathiostrobin, cyproconazole,5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, fluthiazolinil, fluopyram, pyrapropoyne, 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-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetrapr ole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-diphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 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, trinexapac-ethyl, syringoxystrobin, zhongshengmycin, thiophanate-copper, thiazole zinc, amectotractin, iprodione, 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] amide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, 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]propionamide,4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 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-carboxylic acid ethyl ester, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine which can be prepared from 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 (this compound can be prepared by 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 (this compound can be prepared by the method described in WO 2017 / 029179), 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared by 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 by the method described in WO 2016 / 156290),

[0164] 2-Amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester (this compound can be prepared by the method described in WO 2014 / 006945), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be prepared by the method described in WO 2011 / 138281), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide.

[0165] 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-enamine (this compound can be prepared by the method described in WO2018 / 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 by the method described in WO2016 / 202742), 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675).

[0166] The compounds of the present invention can also be used in combination with anthelmintics. Such anthelmintics include compounds selected from macrolide compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemaketin and milbemycin derivatives, as described in EP-357460, EP-444964 and EP-594291. Other anthelmintics include semisynthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944 and WO-9522552. Other anthelmintics include benzimidazoles, such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxbendazole, parbendazole and other members of the described class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetramisole, levamisole, pyrantel pamoate, octadalafil or morantel. Additional anthelmintics include flukeicides (such as triclabendazole and clorsulon) and tapewormicides (such as praziquantel and ethacistel).

[0167] The compounds of the present invention may be used in combination with derivatives and analogs of the paraherquamide / marcfortine class of anthelmintics and antiparasitic oxazolines such as disclosed in US-5478855, US-4639771 and DE-19520936.

[0168] The compounds of the present invention may be used in combination with derivatives and analogs of the general class of dioxymorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.

[0169] The compounds of the present invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as chlorfenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid, etc.

[0170] The compounds of the invention may be used in combination with terpene alkaloids, such as those described in WO 95 / 19363 or WO 04 / 72086, in particular the compounds disclosed therein.

[0171] Other examples of such biologically active compounds that can be used in combination with the compounds of the present invention include, but are not limited to, the following:

[0172] Organophosphates: acephate, methyl pyraclofos, ethyl azinphos-methyl, methyl azinphos-methyl, bromophos, ethyl bromophos, cadusin, chlorethoxyphos, chlorpyrifos, chlorfenapyr, chlormethylphos, demeton, demeton-S-methyl, demeton-S-methyl sulfone, chlormethimide, diazinon, dichlorvos, dicrotophos, dimethoate, ethion, ethion, ethion, oxamethoxam, fenamiphos, fenitrothion, fenthion, fenthion, fenthion, fenthion, pyrifos, fenfothion, anchovy, thiamethoxam, heptenophos, chlorazophos, isopropylphos, isoxazophos, ma Lathion, cypermethrin, methamidophos, methidathion, methyl parathion, mefenphos, monocrotophos, dibromophos, omethoate, methyl oxo-demeton, paraoxon, parathion, methyl parathion, fenthion, phosalone, thiocyanate, phosphine, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, cypermethrin, cypermethrin-methyl, bromophos, pyraclofos, pyridazinphos, quinalphos, thiocarb, thimeton, terbufos, butylpyrimidinphos, stirofosate, thimeton, triazophos, trichlorfon, and chlorpyrifos.

[0173] Carbamates: aldicarb, 2-sec-butylphenyl methyl carbamate, benfuracarb, carbaryl, chlorpyrifos, carbofuran, butylthiocarb, diflubenzuron, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-isopropylphenylbutynyl (methyl) carbamate, cypermethrin, pirimicarb, propoxur, thiodicarb, long-lasting carb, triazolam, UC-51717.

[0174] Pyrethroids: acralthrin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxathiolane-3-ylidenemethyl) cyclopropanecarboxylate, bifenthrin, β-cypermethrin, cypermethrin, alpha-cypermethrin, β-cypermethrin, bio-allethrin, bio-allethrin ((S)-cyclopentyl isomer), bio-resmethrin, bifenthrin, NCI-85193 , pyrethroids, cyhalothrin, cythithrin, cypermethrin, deltamethrin, d-cypermethrin, esfenvalerate, ether cypermethrin, pentothrin, cypermethrin, cypermethrin, flucythrin, flucythrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrin (natural product), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, flutothrin, t-fluvalinate, tefluthrin, tralomethrin, ζ-cypermethrin.

[0175] Arthropod growth regulators: a) Chitin synthesis inhibitors: benzoyl ureas: chloranil, diflubenzuron, fluazuron, flufenoxuron, flufenoxuron, fluflumuron, lufenuron, diflubenzuron, diflubenzuron, cypermethrin, buprofezin, benzylpyridin, hexathiapiprofen, etoxazole, chlorfentazine; b) Ecdysone antagonists: chlorfenapyr, methoxyfenozide, fenbufenozide; c) Juvenile hormone analogs: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) Lipid biosynthesis inhibitor: spirodiclofen.

[0176] Other antiparasitic drugs: acequinoxaline, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, sulfamethoxazole, bifenazate, binacarb, bromocriptine, BTG-504, BTG-505, toxaphene, cartap, dimethoate, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, clothianidin, cypermethrin, diacloden, cypermethrin, DBI-3204, diclofenac, dihydroxy Methyl dihydroxypyrrolidine, dimethoate, dimethoate, endosulfan, ethiprole, fenpyroxen, flumite, MTI-800, fenpyroximate, pyrimidine, flumethrin, bromothrin, flumethoate, trifluroxyfen, halofenprox, hydrazone, IKI-220, sodium silicate, NC-196, neem guard), nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbute, pymetrozine, pyridabenzane, pyrimidine, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, flutoxin, silomadine, spinosad, tebufenpyrad, trichloroacetic acid sulfone, tetracycline, thiacloprid, thiamethoxam, tolfenpyrad, triacetin, triacylglycerol, synergistic acetyl ether, vertalec, YI-5301.

[0177] Biological agents: Bacillus thuringiensis ssp aizawai, Bacillus thuringiensis ssp kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, insect pathogenic bacteria, viruses and fungi.

[0178] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0179] Other biologics: enrofloxacin, febantel, pentoxacillin, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefuroxime, tolamectin, ceftiofur, carprofen, mefluazione, praziquantel, triclabendazole.

[0180] Another aspect of the invention relates to the use of a compound of formula (I), or preferably an individual compound as defined above, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicidal or insecticidal mixture as defined above comprising at least one compound of formula (I) or at least one preferred individual compound as defined above mixed with other fungicides or insecticides for controlling or preventing plants, such as useful plants (such as crops), their propagation material (such as seeds), harvested crops (such as harvested food crops), or non-living materials from infestation by insects or phytopathogenic microorganisms, preferably fungal organisms.

[0181] Another aspect of the invention relates to a method for controlling or preventing plants, such as useful plants (such as crops), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or non-living materials from infestation by insects or phytopathogenic microorganisms or spoilage microorganisms or organisms potentially harmful to humans (especially fungal organisms), which method comprises applying a compound of formula (I) or preferably a single compound as defined above as an active ingredient to the plants, parts of the plants or to their base, their propagation materials, or any part of non-living materials.

[0182] Control or prevention means the reduction of infestation by insects or phytopathogenic or spoilage microorganisms or organisms potentially harmful to man (especially fungal organisms) to such a level that an improvement is demonstrated.

[0183] The preferred method for controlling or preventing crops from being infected by plant pathogenic microorganisms (especially fungi) or insects is foliar application, which includes applying a compound with formula (I) or an agrochemical composition containing at least one of the compounds. Frequency of application and application ratio will depend on the risk of infection by the corresponding pathogen or insect. However, the compound with formula (I) can also be applied to the soil by roots (systemic action) by soaking the bottom of the plant with a liquid formulation or by applying the compound in solid form, for example, in the form of particles (soil application) to the soil. In rice crops, such particles can be applied to the paddy field of irrigation. The compound with formula (I) can also be applied to the seed (coating) by dipping seeds or tubers with a liquid formulation of fungicide or applying it with a solid formulation.

[0184] A formulation, e.g. a composition comprising a compound of formula (I) and, if desired, a solid or liquid adjuvant or a monomer for encapsulating the compound of formula (I) can be prepared in a known manner, typically by intimately mixing and / or grinding the compound with extenders, e.g. solvents, solid carriers and, optionally, surface-active compounds (surfactants).

[0185] Advantageous application rates are generally from 5 g to 2 kg of active ingredient (ai) / 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 suitable dosage is from 10 mg to 1 g of active substance / kg seed.

[0186] When the combination according to the invention is used to treat seed, a rate of from 0.001 g to 50 g of compound of formula (I) per kg of seed, preferably from 0.01 g to 10 g per kg of seed, is generally sufficient.

[0187] The composition of the present invention can be used in any conventional form, for example, in the form of a two-pack, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a seed treatment flowable concentrate (FS), a seed treatment solution (LS), a seed treatment water dispersible powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an oil-in-water emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil suspension (OD), an oil suspension (OF), an oil-soluble liquid (OL), a soluble concentrate (SL), an ultra low volume suspension (SU), an ultra low volume liquid (UL), a master batch (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with an agriculturally acceptable adjuvant.

[0188] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with an appropriate formulation inert agent (diluent, solvent, filler and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, adhesives, thickeners and compounds providing adjuvant effects). Conventional sustained-release formulations intended to last for a long time can also be used. In particular, formulations to be applied in a spray form (such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules) can contain surfactants (such as wetting agents and dispersants) and other compounds providing adjuvant effects, such as condensation products of formaldehyde with naphthalene sulfonates, alkyl aryl sulfonates, lignin sulfonates, fatty alkyl sulfates and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0189] The seed dressing formulation is applied to the seed in a manner known per se using the combination of the invention and the diluent in the form of a suitable seed dressing formulation, for example an aqueous suspension or dry powder having 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 sustained-release capsule or microcapsule.

[0190] Typically, the formulation comprises from 0.01% to 90% by weight of active ingredient, from 0 to 20% of agriculturally acceptable surfactants and 10% to 99.99% of solid or liquid formulation inert agents and adjuvants, the active agent being composed of at least a compound of formula (I) together with components (B) and (C), and optionally other active agents (particularly microbicides or preservatives or the like). By weight, the concentrated form of the composition typically contains between about 2% and 80%, preferably between about 5% and 70% of the active agent. By weight, the application form of the formulation can, for example, contain from 0.01% to 20%, preferably from 0.01% to 5% of the active agent. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0191] Table 1 below shows examples of individual compounds of formula (I) according to the invention.

[0192] Table 1: The individual compounds according to the present invention having the formula (I)

[0193]

[0194]

[0195] in

[0196] a) 30 compounds of formula (Ia):

[0197]

[0198] Where R 1 , X and Y are as defined in Table 1.

[0199] b) 30 compounds of formula (Ib):

[0200]

[0201] Where R 1 , X and Y are as defined in Table 1.

[0202] c) 30 compounds of formula (Ic):

[0203]

[0204] Where R 1 , X and Y are as defined in Table 1.

[0205] d) 30 compounds of formula (Id):

[0206]

[0207] Where R 1 , X and Y are as defined in Table 1.

[0208] e) 30 compounds of formula (Ie):

[0209]

[0210] Where R 1 , X and Y are as defined in Table 1.

[0211] f) 30 compounds having formula (If):

[0212]

[0213] Where R 1 , X and Y are as defined in Table 1.

[0214] g) 30 compounds of formula (Ig):

[0215]

[0216] Where R 1 , X and Y are as defined in Table 1.

[0217] h) 30 compounds of formula (Ih):

[0218]

[0219] Where R 1 , X and Y are as defined in Table 1.

[0220] i) 30 compounds of formula (Ii):

[0221]

[0222] Where R 1 , X and Y are as defined in Table 1.

[0223] j) 30 compounds of formula (Ij):

[0224]

[0225] Where R 1 , X and Y are as defined in Table 1.

[0226] k) 30 compounds of formula (Ik):

[0227]

[0228] Where R 1 , X and Y are as defined in Table 1.

[0229] 1) 30 compounds having formula (I1):

[0230]

[0231] Where R 1 , X and Y are as defined in Table 1.

[0232] m) 30 compounds of formula (Im):

[0233]

[0234] Where R 1 , X and Y are as defined in Table 1.

[0235] n) 30 compounds having formula (In):

[0236]

[0237] Where R 1 , X and Y are as defined in Table 1.

[0238] o) 30 compounds of formula (Io):

[0239]

[0240] Where R 1, X and Y are as defined in Table 1.

[0241] p) 30 compounds of formula (Ip):

[0242]

[0243] Where R 1 , X and Y are as defined in Table 1.

[0244] Preparation Examples

[0245]

[0246] The active ingredient is mixed thoroughly with the adjuvant and the mixture is ground thoroughly in a suitable grinder to provide a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0247]

[0248] The active ingredient is mixed thoroughly with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a powder which can be used directly for seed treatment.

[0249] Emulsifiable concentrates

[0250]

[0251] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0252]

[0253] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing of seeds.

[0254] Extruder pellets

[0255]

[0256]

[0257] The active ingredient is mixed with the adjuvant and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0258] Coated granules Active ingredient [compound of formula (I)] 8%

[0259] Polyethylene glycol (molecular weight 200) 3%

[0260] Kaolin 89%

[0261] The finely ground active ingredient is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, non-dusty coated granules are obtained.

[0262] Suspension concentrates

[0263]

[0264] The finely ground active ingredient is intimately mixed with an adjuvant to give a suspension concentrate from which a suspension of any desired dilution can be obtained by dilution with water. Using such a dilution, living plants together with plant propagation materials can be treated and protected against microbial infection by spraying, pouring or immersion.

[0265] Flowable concentrate for seed treatment

[0266]

[0267]

[0268] The finely ground active ingredient is intimately mixed with an adjuvant to give a suspension concentrate from which a suspension of any desired dilution can be obtained by dilution with water. Using such a dilution, living plants together with plant propagation materials can be treated and protected against microbial infection by spraying, pouring or immersion.

[0269] Extended-release capsule suspension

[0270] 28 parts of a combination of compounds of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). The mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is reached. To the emulsion is added 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete.

[0271] The obtained capsule suspension is stabilized by adding 0.25 parts of thickener and 3 parts of dispersant. The capsule suspension formulation contains 28% of active ingredient. The diameter of the median capsule is 8-15 microns.

[0272] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for this purpose.

[0273] Examples

[0274] The following examples are used to illustrate the present invention. The compounds of the present invention can be distinguished from known compounds by greater efficacy at low application rates, which can be confirmed by one of ordinary skill in the art using the experimental procedures outlined in the examples, using lower application rates (if necessary) such as 50ppm, 12.5ppm, 6ppm, 3ppm, 1.5ppm, 0.8ppm or 0.2ppm.

[0275] Compounds of formula (I) may have any number of benefits, including, among others, favorable levels of biological activity for protecting plants against diseases caused by fungi or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, favorable activity spectrum, increased safety (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).

[0276] List of abbreviations

[0277] bs = broad singlet

[0278] ℃ = degrees Celsius

[0279] CDCl3 = chloroform-d

[0280] d = doublet

[0281] Pd2(dba)3 = tris(dibenzylideneacetone)dipalladium(0)

[0282] DIPEA = N,N-diisopropylethylamine

[0283] DMF = dimethylformamide

[0284] h = hours

[0285] HATU = 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate

[0286] m = multiplet

[0287] MHz = Megahertz

[0288] mp = melting point

[0289] N = Normal

[0290] ppm = parts per million

[0291] s = single peak

[0292] THF = Tetrahydrofuran

[0293] Xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

[0294] Example 1 : This example illustrates the preparation of 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Compound Ib23)

[0295]

[0296] a) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid methyl ester

[0297]

[0298] Under argon atmosphere, by Xantphos (0.2 equivalent), Pd (dba) (0.1 equivalent) and cesium carbonate (2 equivalents) are added to degassed, stirred 2-bromo-5-methyl-thiazole-4-formic acid methyl esters (4.6g, 18.5mmol, 1 equivalent) and 2,6-difluoropyridine-4-amine (1 equivalent) in the mixture in 1,4-dioxane (660mL).Reaction is heated to reflux and stirs 4h, then the temperature is cooled to room temperature.Mixture is diluted with ethyl acetate and filtered through diatomite, and rotary evaporator is used to concentrate the gained filtrate.By silica gel column chromatography (eluent hexamethylenetetramine / ethyl acetate mixture) purifying, obtain desired 2-[(2,6-difluoro-4-pyridyl) amino]-5-methyl-thiazole-4-formic acid methyl esters (1.8g, 6.31mmol). 1 H-NMR (400MHz, CDCl3): δ=2.73 (s, 3H), 3.94 (s, 3H), 6.75 (s, 1H).

[0299] b) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid

[0300]

[0301] Lithium hydroxide monohydrate (4 equivalents) is added to a solution of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid (1.8 g, 6.31 mmol) in a mixture of tetrahydrofuran (35 mL) and water (12 mL). The reaction mixture is stirred at room temperature for 16 h, and then the solvent is removed in a vacuum. The residue is diluted with ethyl acetate and water, and then 2N hydrochloric acid is slowly added until a pH of 3-4 is reached. The formed precipitate is separated by filtration, and washed twice with water to obtain the desired product 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid (1.55 g, 5.71 mmol). 1 H-NMR (400MHz, (CD3)2SO): δ = 2.69 (s, 3H), 7.30 (s, 2H), 11.35 (bs, 1H), 12.90 (bs, 1H).

[0302] c) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide

[0303]

[0304] (2,2-dimethylcyclobutyl)ammonium chloride (1.1 eq.), HATU (1.1 eq.) and DIPEA (2.6 eq.) were added sequentially to a DMF solution (9.2 mL) of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid (250 mg, 0.92 mmol, 1 eq.). The resulting solution was stirred at room temperature for 1 h until the starting material was consumed (LCMS control). Then, saturated NaHCO3 solution was added to the mixture and the solution was extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and volatiles were removed by a rotary evaporator. Purification by silica gel column chromatography (eluent: a mixture of cyclohexane / ethyl acetate) gave the desired product 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (280 mg, 86% yield). 1 H-NMR (400MHz, CDCl3): δ=1.17(s,3H),1.20(s,3H),1.50-1.75(m,2H),1.86-1.92(m,1H), 2.29-2.36(m,1H),2.79(s,3H),4.25-4.31(m,1H),6.87(s,2H),7.32(d,1H),7.67(s,1H).

[0305] d) 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Compound Ib23)

[0306]

[0307] At -78 ° C, butyl lithium (2.5M solution in hexane, 1.25 equivalents) was added to a stirred solution of 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (300 mg, 0.85 mmol, 1 equivalent) in THF (4.3 mL). After 30 min, cyanogen bromide was added to the solution, the reaction was allowed to reach room temperature and stirred for 2 h. The reaction was then quenched with a saturated aqueous solution of NaHCO3, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over sodium sulfate and volatiles were removed using a rotary evaporator. Purification by silica gel column chromatography (eluent: cyclohexane / ethyl acetate mixture) gave the desired product 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (190 mg, 0.50 mmol, 59% yield). 1 H-NMR (400MHz, CDCl3): δ=1.10(s,3H),1.21(s,3H),1.55-1.69(m,2H),1.80-1.93( m,1H),2.25-2-35(m,1H),2.90(s,3H),4.25-4.31(m,1H),6.92(s,2H),7.12(d,1H).

[0308] Throughout this specification, temperatures are given in degrees Celsius (° C.) and “mp” refers to melting point. LC / MS refers to liquid chromatography mass spectrometry, and the apparatus description and methods are:

[0309] Method A:ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 μm particle size, 30×2.1 mm column, 0.85 mL / min., 60° C., H 2 O / MeOH 95:5+0.05%HCOOH(90%) / CH3CN+0.05%HCOOH(10%)–1.2min.–CH3CN+0.05%HCOOH(100%)–0.30min., ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: positive ion; capillary voltage (kV) 3.00, cone voltage (V) 30.00, extractor (V) 2.00, source temperature (℃) 150, desolvation temperature (℃) 350, cone backflush gas flow (L / Hr) 0, desolvation gas flow (L / Hr) 650).

[0310] Method B: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 μm particle size, 30×2.1 mm column, 0.85 mL / min., 60°C, H2O / MeOH 95:5 + 0.05% HCOOH (90%) / CH3CN + 0.05% HCOOH (10%) – 2.7 min. – CH3CN + 0.05% HCOOH (100%) – 0.30 min., ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: positive ion; capillary voltage (kV) 3.00, cone voltage (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone backflush gas flow (L / Hr) 0, desolvation gas flow (L / Hr) 650).

[0311] Method C: MS: ZQ mass spectrometer from Waters (single quadrupole mass spectrometer)

[0312] Instrument parameters: Ionization method: electrospray polarity: positive (negative) ion capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, gas temperature (°C) 350, drying gas flow (mL / min) 9.8, plasma gas pressure (Nebpress) 45 psig, mass range: 90 to 1000 Da.

[0313] HPLC:HP 1100 HPLC from Agilent: solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment and diode array detector. Column: porpshell 120 C18, 2.7 μm particle size, 120 Angstroms, 4.6×50 mm, temperature: 30° C. DAD wavelength range (nm): 190 to 400 Solvent gradient: A=water+0.1% HCOOH. B=acetonitrile+0.08% HCOOH

[0314]

[0315] Table 2: Melting points and LC / MS data of selected compounds in Table 1 (R t = retention time).

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323] Surprisingly, it has been found that novel compounds of formula (I) having the following characteristics can show improved solubility properties (especially in non-polar solvents) and / or photostability properties when compared to their corresponding free amines (i.e., wherein the nitrile group on the nitrogen is replaced by hydrogen, as known, for example, from WO 2017 / 207362).

[0324] Throughout the following description, LogP means logarithm of the partition coefficient, ppm means parts per million, and T 50 represents the half-life of the compound under irradiation conditions.

[0325] The methods used for these measurements are presented below.

[0326] Partition coefficient

[0327] The octanol-water partition coefficient (expressed as LogP) is measured by the HPLC method using a reversed phase minicolumn coated with octanol. The partition coefficient P is proportional to the HPLC retention factor. The general principle of this method has been described, for example, in J. Pharm. Sci. [Journal of Pharmaceutical Science], 67 (1978) 1364-1367.

[0328] A Waters HPLC system (model 1525 binary pump; 2707 autosampler with thermostat and model 2298 photodiode array detector) was used with Hichrom mini columns and an aqueous mobile phase containing 20 mM phosphate buffer saturated with 1-octanol (Aldrich, HPLC grade) adjusted to pH 7. The mini columns used were HiRPB stationary phase, 4.6 mm id by 4 mm long or 2 mm id by 10 mm long. Anisole (Aldrich, 99%+ purity, LogP 2.11) was used as the primary reference for calibration of the system.

[0329] Photostability

[0330] Light stability testing was performed by irradiating thin film deposits of compounds and formulations on glass surfaces using a filtered xenon lamp system (Atlas Suntest) that reproduces the spectrum and intensity of sunlight. The spectral output power of the Suntest was set to 750 W / m2, which is a typical daily maximum irradiance level at noon (midsummer, UK).

[0331] Typically, the test compound is dissolved in HPLC grade methanol to give a 1 g / L stock solution. Alternatively, the formulated compound is suspended in water at the same concentration. A 2 μL droplet of the test solution is spotted onto a microscope coverslip on a 3D printed support, allowed to dry, and then irradiated for different times in the Suntest. The coverslip is then removed from the Suntest and placed in a 4 dram vial; 1 mL of wash solvent (typically 30:70 acetonitrile:0.2% aqueous formic acid) is added, and the vial is shaken to extract the compound into solution. The solution is analyzed by reverse phase HPLC, typically using a Waters UPLC system with a photodiode array (PDA) and a Waters column (BEH C18, 100×2.1 mm×1.7 μm), using a mixed water:acetonitrile mobile phase acidified with 0.2% formic acid. Peaks are detected at the optimal wavelength for each candidate compound, and the PDA peak area is used for quantification. T is estimated using a plot of % loss versus time 50 value, which is the time taken for 50% of the initial loss of the test compound.

[0332] Solubility

[0333] Saturated solutions of the test compound were prepared in aqueous buffer (10 mM mixed phosphate, pH 7.20) or in heptane. Typically, 1 mg of the test compound in a 2 dram vial with 1 mL of buffer or heptane was left on a roller shaker overnight (20 hours) after an initial 20 minute period in an ultrasonic bath. The saturated sample was then filtered through a Millex-HV 0.45 micron syringe driven filter (depending on whether the solvent was aqueous or non-aqueous). The aqueous samples were then analyzed by direct injection on the LCMS, and the peak areas detected using the PDA were compared to standards of known concentration; the heptane samples were first dried and redissolved in an LC compatible solvent (typically 30:70 acetonitrile:0.2% formic acid). Variations on the protocol included pre-saturation of the filter for compounds expected to have very low solubility, and centrifugation of saturated samples of oil.

[0334] Table 3 below illustrates the unexpected physicochemical properties (partition coefficient LogP, solubility in heptane and / or photostability) of the prior art compounds relative to WO 2017 / 207362.

[0335] Table 3

[0336]

[0337] Biological Examples

[0338] Example B1: Alternaria solani / Tomato / Leaf discs (early blight)

[0339] Tomato leaf discs cv. Baby were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. Two days after application, the leaf discs were inoculated with a spore suspension of the fungus. Inoculated leaf discs were cultivated at 23°C / 21°C (day / night) and 80% rh in a climate chamber under a 12 / 12h (lighting / dark) light regime, and compound activity was assessed as the percentage of disease control compared to the untreated when appropriate levels of disease damage appeared on untreated control leaf discs (5-7 days after application). The following compounds gave at least 80% control of Alternaria solani at 200ppm when compared to the untreated control that showed extensive disease development under the same conditions: Ia23, Ib08, Ib23, Ic23, Ig23, Ii23, Ik18, Im18.

[0340] Example B2:Botryotinia fuckeliana, Botrytis cinerea / Liquid culture (Botryotinia cinerea)

[0341] The fungal conidia from frozen storage were directly mixed into the nutrient broth (Vogels broth). After the (DMSO) solution of the test compound was placed in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application. When compared to the untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Botrytis cinerea at 20ppm: Ib23, Ic23, Ih23, Ik23, Io23.

[0342] Example B3: Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (anthracnose)

[0343] The fungal conidia from cryogenic storage were directly mixed into the nutrient broth (PDB-potato dextrose broth). After the (DMSO) solution of the test compound was placed in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plate was incubated at 24°C and the inhibition of growth was measured photometrically after 3-4 days of application.

[0344] The following compounds gave at least 80% control of Aspergillus niger at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia18, Ib08, Ib18, Ib23, Ib25, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih18, Ih23, Ii23, Ij23, Ik18, Ik23, Il18, Il23, Im18, Io23, Ip23.

[0345] Example B4: Wheat powdery mildew (Blumeria graminis f.sp.tritici, Erysiphe graminis f.sp.Tritici) / wheat / leaf discs preventive (powdery mildew on wheat)

[0346] Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. One day after application, leaf discs were inoculated by shaking powdery mildew infected plants over the test plates. Inoculated leaf discs were incubated at 20° C. and 60% rh in a climate chamber under a lighting regime of 24 h dark followed by 12 h light / 12 h dark, and the activity of the compounds was evaluated as a percentage of disease control compared to the untreated when appropriate levels of disease damage appeared on untreated control leaf segments (6-8 days after application).

[0347] The following compounds gave at least 80% control of wheat powdery mildew at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia23, Ib08, Ib18, Ib23, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih23, Ii23, Ij23, Ik18, Ik23, Il23, Im18, Io23, Ip23.

[0348] Example B5: Fusarium oxysporum / wheat / spikelet preventive (head blight)

[0349] Wheat spikelets cultivar Monsun were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the spikelets were inoculated with a spore suspension of the fungus. The inoculated spikelets were incubated at 20°C and 60% rh in a climatic chamber under a light regime of 72 h semi-darkness followed by 12 h light / 12 h dark, and the activity of the compound was evaluated as the percentage of disease control when compared to the untreated spikelets when appropriate levels of disease damage appeared (after 6-8 days after application).

[0350] The following compounds gave at least 80% control of Fusarium oxysporum at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ib23.

[0351] Example B6: Phaeosphaeria nodorum, Septoria nodorum / wheat / leaf disc preventive (glume blight)

[0352] Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. 2 days after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated test leaf discs were incubated at 20°C and 75% rh in a climate chamber under a light regime of 12h illumination / 12h darkness, and compound activity was assessed as the percentage of disease control compared to the untreated when appropriate levels of disease damage appeared on untreated control leaf discs (5-7 days after application).

[0353] The following compounds gave at least 80% control of Septoria nodosum at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia23, Ib23, Id23, If23, Ig23, Ii23, Ik18, Ik23.

[0354] Example B7: Monographella nivalis (Microdochium nivale) / liquid culture (cereal root rot)

[0355] The fungal conidia from cryogenic storage were directly mixed into the nutrient broth (PDB-potato dextrose broth). After the (DMSO) solution of the test compound was placed in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

[0356] The following compounds gave at least 80% control of Thielavia nigra at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia18, Ia23, Ib08, Ib18, Ib23, Ib25, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih18, Ih23, Ii23, Ij23, Ik18, Ik23, Il18, Il23, Im18, Io23, Ip23.

[0357] Example B8: Mycosphaeria arachidis (Cercospora arachidis) / liquid culture (early leaf spot)

[0358] Fungal conidia from cryogenic storage were directly mixed into nutrient broth (PDB-potato dextrose broth). After placing the (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

[0359] The following compounds gave at least 80% control of Mycosphaeria arachidis at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia18, Ib08, Ib18, Ib23, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih18, Ih23, Ii23, Ik18, Ik23, Il18, Il23, Im18, Io23, Ip23.

[0360] Example B9: Phakopsora pachyrhizium / soybean / preventive (soybean rust)

[0361] Soybean leaf discs were placed on water agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. One day after application, the leaf discs were inoculated by spraying the lower leaf surface with a spore suspension. After an incubation period of 24-36 hours in the dark at 20°C and 75% rh in a climate chamber, the leaf discs were kept at 20°C with 12h lighting / day and 75% rh. When appropriate levels of disease damage appeared in untreated control leaf discs (12-14 days after application), the activity of the compounds was evaluated as the percentage of disease control compared to the untreated.

[0362] The following compounds gave at least 80% control of Phakopsora pachyrhizi at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ib23, If23, Ig23, Ih23, Ii23, Il23, Ip23.

[0363] Example B10: Plasmopara viticola / grapes / leaf discs preventive (late blight)

[0364] Grapevine leaf discs were placed on water agar medium in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. One day after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated at 19°C and 80% rh in a climate chamber under a light regime of 12h illumination / 12h darkness, and compound activity was assessed as the percentage of disease control compared to the untreated when appropriate levels of disease damage appeared in untreated control leaf discs (6-8 days after application).

[0365] The following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ig08, Il18.

[0366] Example B11: Puccinia recondita f.sp.tritici / wheat / leaf disc treatment (brown rust)

[0367] Wheat leaf segments cv. Kanzler were placed on agar in a multiwell plate (24-well format). The leaf fragments were inoculated with a spore suspension of the fungus. The plates were stored in the dark at 19°C and 75% rh. One day after inoculation, the formulated test compounds diluted in water were applied. The leaf segments were incubated at 19°C and 75% rh in a climate chamber under a lighting regime of 12h light / 12h dark, and the activity of the compounds was evaluated as a percentage of disease control compared to the untreated when appropriate levels of disease damage appeared in the untreated control leaf segments (6-8 days after application).

[0368] The following compounds at 200 ppm gave at least 80% control of Puccinia reconditatis of wheat: Ib23, Ic23, Ih23, Ii23, Ik23, Il23, Ip23 when compared to untreated controls which showed extensive disease development under the same conditions.

[0369] Example B12: Puccinia tritici / wheat / leaf disc preventive (brown rust)

[0370] Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. One day after application, the leaf disks were inoculated with a spore suspension of the fungus. The inoculated leaf segments were incubated at 19° C. and 75% rh in a climate chamber under a lighting regime of 12 h light / 12 h dark, and the activity of the compounds was evaluated as a percentage of disease control compared to the untreated when appropriate levels of disease damage appeared in the untreated control leaf segments (7-9 days after application).

[0371] The following compounds gave at least 80% control of Puccinia reconditatis of wheat at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia18, Ia23, Ib08, Ib18, Ib23, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih18, Ih23, Ii23, Ij23, Ik23, Il18, Il23, Im18, Io23, Ip23.

[0372] Example B13: Rice blast fungus (Pyricularia oryzae) / Rice / Leaf discs for prevention (Rice blast)

[0373] Rice leaf segments cv. Ballila were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. After 2 days after application, the leaf segments were inoculated with a spore suspension of the fungus. The inoculated leaf segments were incubated at 22° C. and 80% rh (relative humidity) in a climate chamber under a light regime of 24 h dark followed by 12 h light / 12 h dark, and the activity of the compound was evaluated as a percentage of disease control compared to the untreated test leaf segments when appropriate disease damage levels appeared (after 5-7 days after application).

[0374] The following compounds gave at least 80% control of Magnaporthe oryzae at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia18, Ia23, Ib08, Ib18, Ib23, Ic23, Id23, Ie23, If23, Ig08, Ig23, Ih23, Ii23, Ij23, Ik18, Ik23, Il18, Il23, Im18, Io23, Ip23.

[0375] Example B14:Pyrenophora teres / barley / leaf disc preventive (net spot)

[0376] Barley leaf segments cv. Hasso are placed on agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 20°C and 65% rh in a climatic chamber under a light regime of 12h light / 12h dark and when appropriate levels of disease damage appear on untreated control leaf segments (after 5-7 days after application), the activity of the compounds is evaluated as the percentage of disease control compared to the untreated.

[0377] The following compounds gave at least 80% control of Pyrrolizidine occludin at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia23, Ib18, Ib23, Ic23, Id23, Ig23, Ii23, Ik23, Ip23.

[0378] Example B15: Sclerotinia sclerotiorum / liquid culture (cotton rot)

[0379] Mycelial fragments of freshly grown liquid cultures of the fungus are mixed directly into nutrient broth (PDB (potato dextrose broth)). After placing a (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal material is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3-4 days after application.

[0380] The following compounds gave at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ib18, Ib23, Ic23, If23, Ig23, Ih23, Ii23.

[0381] Example B16: Mycosphaerella graminicola (Septoriatritici) / liquid culture (Septoria blotch)

[0382] The fungal conidia from cryogenic storage were directly mixed into the nutrient broth (PDB-potato dextrose broth). After the (DMSO) solution of the test compound was placed in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.

[0383] The following compounds gave at least 80% control of Mycosphaeria graminearum at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions: Ia23, Ib08, Ib18, Ib23, Ib25, Ic23, Id23, Ie23, If23, Ig23, Ih18, Ih23, Ii23, Ij23, Ik18, Ik23, Il18, Il23, Im18, Io23, Ip23.

Claims

1. A compound having formula (I): in, Y is CF; R 1 is methyl or HC(O)NH-; R 2 is C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl, phenylC1-C2 alkyl, or a 5- to 12-membered non-aromatic spirocyclic carbobicyclic or carbotricyclic ring system, wherein the cycloalkyl is unsubstituted or substituted by 1 or 2 R 3 and wherein the phenyl ring is unsubstituted or substituted with 1 or 2 groups represented by R 3 The group represented by is substituted; R 3 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C3-C8 cycloalkyl or C3-C8 cycloalkylC1-C2 alkyl; and X is N; or a salt thereof.

2. The compound according to claim 1, wherein R 1 It's methyl.

3. The compound according to claim 1 or claim 2, wherein R 2 is n-butyl, isobutyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, n-hexyl, 1-(cyclopropylmethyl)cyclopropylmethyl, cyclobutyl, 2,2-dimethylcyclobutyl, 1-methylcyclopentyl, benzyl, 1-phenylethyl, 3,5-bis(trifluoromethyl)benzyl, spiro[3.3]heptyl, spiro[3.4]octyl or spiro[cyclobutane-1,2′-indanyl].

4. The compound according to claim 1 or claim 2, wherein R 3 It is C1-C3 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkylC1-C2 alkyl.

5. The compound according to claim 1, wherein the compound of formula (I) is 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-formamido-thiazole-4-carboxamide (1.b.25), 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-[[1-(cyclopropylmethyl)cyclopropyl]methyl]-5-methyl-thiazole-4-carboxamide (1.f.23), 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3.3]heptan-3-yl- Thiazole-4-carboxamide (1.e.23), 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide (1.c.23), 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[cyclobutane-2,2'-indan]-1-yl-thiazole-4-carboxamide (1.d.23) or 2-[Cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (1.b.23).

6. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 5.

7. The agrochemical composition according to claim 6, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

8. A method for controlling or preventing infection of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 5 or a composition comprising said compound as active ingredient is applied to the plants, parts thereof or the locus thereof.

9. Use of a compound of formula (I) as a fungicide according to any one of claims 1 to 5, wherein the use does not comprise a method of treatment of the human or animal body by surgery or therapy.

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