Microbicidal derivatives

Abstract

Compounds of formula (I) are useful as pesticides, particularly as fungicides and bactericides. [Formula 1] TIFF2022534913000046.tif59157 (wherein the substituents are as defined in claim 1).

Description

[Technical field]

[0001] The present invention relates to microbicidal azabenzodioxole derivatives, e.g. as active ingredients, having microbicidal activity, in particular fungicidal and fungicidal activity. The present invention also relates to the preparation of these azabenzodioxole derivatives, to agrochemical compositions comprising at least one azabenzodioxole derivative, and to the use of azabenzodioxole derivatives or compositions thereof in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living material by phytopathogenic microorganisms, preferably fungi. [Background technology]

[0002] WO 2015 / 040405 describes pyridinecarboxamide derivatives as pesticides. Summary of the Invention [Means for solving the problem]

[0003] According to the present invention, a compound of formula (I): [ka] (In the formula, R 1 is hydrogen, cyano, formyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxyC1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, C1-C6 alkoxyC1-C3 alkoxycarbonyl, C1-C6 alkoxyoxalyl, C1-C6 alkoxycarbonyl C1-C4 alkylC1-C6 alkoxycarbonyl, C1-C6 alkylsulfanylcarbonyl, or phenylcarbonyl; R 2 and R 3 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, halogen, or C1-C6 alkoxyC1-C2 alkyl; R 4is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 (optionally substituted with 1 to 3 groups represented by the formula:), phenyl, phenyl C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclyl C1-C3 alkyl, where heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms or groups individually selected from nitrogen, oxygen, sulfur and S(O)2, where the heterocyclyl group is R 7 or a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally containing 1, 2, 3, 4 or 5 heteroatoms individually selected from nitrogen, oxygen and sulfur, and optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker; R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl group is selected from R 6 optionally substituted with 1, 2 or 3 substituents, which may be the same or different, selected from R 6 is halogen, C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 haloalkyl; R 7 is halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; or its salt or N-oxide is provided.

[0004] It has now been surprisingly found that the novel compounds of formula (I) have, for practical purposes, a highly advantageous level of biological activity which protects plants against diseases caused by fungi. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0005] According to a second aspect of the present invention there is provided an agricultural composition comprising a fungicidally effective amount of a compound of formula (I) according to the present invention, which may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0006] According to a third aspect of the present invention there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound of formula (I), or a composition comprising this compound as an active ingredient, to the plant, a part thereof or its habitat.

[0007] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) as a bactericide or fungicide. According to this particular aspect of the present invention the use may or may not comprise a method for the treatment of the human or animal body by surgery or therapy.

[0008] When a substituent is described as being "optionally substituted," this includes, for example, one, two, or three R 5 It means that the alkyl group may or may not have one or more identical or different substituents such as aryl, ...

[0009] As used herein, the term "cyano" refers to a -CN group.

[0010] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo).

[0011] As used herein, the term "formyl" refers to a -C(O)H group.

[0012] As used herein, the term "acetyl" refers to a -C(O)CH group.

[0013] As used herein, the term "C1-C8 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having 1-8 carbon atoms, and attached to the remainder of the molecule by a single bond. "C1-C6 alkyl", "C1-C4 alkyl" and "C1-C3 alkyl" should be construed accordingly. Examples of C1-C8 alkyl include, but are not limited to, methyl, ethyl, n-propyl and their isomers, e.g., iso-propyl. A "C1-C6 alkylene" group refers to the corresponding definition of C1-C6 alkyl, except for radicals that are attached to the remainder of the molecule by two single bonds. The term "C1-C2 alkylene" should be construed accordingly. Examples of C1-C6 alkylene include, but are not limited to, -CH2-, -CH2CH2- and -(CH2)3-.

[0014] As used herein, the term "C1-C8 haloalkyl" refers to a C1-C8 alkyl radical generally as defined above, substituted with one or more of the same or different halogen atoms. The terms "C1-C6 haloalkyl" and "C1-C4 haloalkyl" should be construed accordingly. Examples of C1-C8 haloalkyl include, but are not limited to, trifluoromethyl.

[0015] As used herein, the term "C1-C8 alkoxy" refers to R a is generally a C1-C8 alkyl radical as defined above a The terms "C1-C6 alkoxy", "C1-C4 alkoxy" and "C1-C3 alkoxy" should be construed accordingly. Examples of C1-C8 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy) and propoxy.

[0016] As used herein, the term "C2-C6 alkenyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond which may be of either the (E)- or (Z)-configuration, having 2-6 carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C2-C3 alkenyl" should be construed accordingly. Examples of C2-C6 alkenyl include, but are not limited to, ethynyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), and but-1-enyl.

[0017] As used herein, the term "C2-C6 alkynyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having 2-6 carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C2-C3 alkynyl" should be construed accordingly. Examples of C2-C6 alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, but-1-ynyl.

[0018] As used herein, the term "C2-C6 alkynyloxy" refers to R a is generally a C2-C8 alkynyl group as defined above a Refers to the group.

[0019] As used herein, the term "C3-C8 cycloalkyl" refers to a radical that is a monocyclic saturated ring system and contains 3 to 8 carbon atoms. The terms "C3-C6 cycloalkyl", "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.

[0020] As used herein, the term "C3-C8 cycloalkyl C1-C2 alkyl" refers to a C3-C8 cycloalkyl ring attached to the remainder of the molecule by a C1-C2 alkylene linker as defined above.

[0021] As used herein, the term "phenyl C1-C2 alkyl" refers to a phenyl ring attached to the remainder of the molecule by a C1-C2 alkylene linker as defined above.

[0022] As used herein, the term "oxetan-3-yl C1-C2 alkyl" refers to an oxetane ring attached to the remainder of the molecule by a C1-C2 alkylene linker as defined above.

[0023] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring radical 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, pyrimidyl, or pyridyl.

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

[0025] As used herein, the term "heterocyclyl" refers to a stable 4-, 5-, or 6-membered non-aromatic monocyclic ring containing one, two, or three heteroatoms, where the heteroatoms are individually selected from nitrogen, oxygen, and sulfur. The heterocyclyl radical may be attached to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocyclyl include, but are not limited to, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl, and thiazolidinyl.

[0026] As used herein, the term "heterocyclylC1-C2 alkyl" refers to a heterocyclyl ring attached to the remainder of the molecule by a C1-C2 alkylene linker as defined above.

[0027] As used herein, a "spirocyclic carbodi- or carbotri-cyclyl ring" is a non-aromatic bicyclic ring system containing two rings linked at one carbon atom, i.e., sharing one carbon atom. Examples of spirocyclic carbodi- or carbotri-cyclyl ring systems include, but are not limited to, spiro[3.3]heptanyl, spiro[3.4]octanyl, spiro[4.5]decanyl, spiro[cyclobutane-1,2'-indanyl], or spiro[cyclopentane-1,2'-tetralinyl].

[0028] As used herein, the term "C1-C6 alkylcarbonyl" refers to R a is generally a C1-C6 alkyl group as defined above, a Refers to the group.

[0029] As used herein, the term "C1-C6 alkoxy C1-C6 alkylcarbonyl" refers to R b is generally a C1-C6 alkyl group as defined above, R a is generally a C1-C6 alkylene group as defined above, a OR b Refers to the group.

[0030] As used herein, the term "C1-C6 haloalkylcarbonyl" refers to R a is generally a C1-C6 haloalkyl group as defined above, a Refers to the group.

[0031] As used herein, the term "C-C cycloalkylcarbonyl" refers to R a is generally a C3-C6 cycloalkyl group as defined above, a Refers to the group.

[0032] As used herein, the term "C1-C6 alkoxycarbonyl" refers to R a is generally a C1-C6 alkyl group as defined above, a Refers to the group.

[0033] As used herein, the term "C1-C6 alkoxyoxalyl" refers to R a is generally a C1-C6 alkyl group as defined above, -C(O)C(O)OR a Refers to the base.

[0034] As used herein, the term "C2-C6 alkenyloxycarbonyl" refers to R a is generally a C2-C6 alkenyl group as defined above, a Refers to the group.

[0035] As used herein, the term "C2-C6 alkynyloxycarbonyl" refers to R a is generally a C2-C6 alkynyl group as defined above, a Refers to the group.

[0036] As used herein, the term "C1-C6 alkylsulfanylcarbonyl" refers to R a is generally a C1-C6 alkyl group as defined above, a Refers to the group.

[0037] As used herein, the term "phenylcarbonyl" refers to R a is a phenyl group, a Refers to the group.

[0038] As used herein, the term "phenyl C1-C2 alkyl" refers to a phenyl group attached to the remainder of the molecule by a C1-C2 alkylene linker as defined above.

[0039] As used herein, the term "phenoxycarbonyl" means a is a phenyl group, the formula -C(O)OR a Refers to...

[0040] As used herein, the term "heteroarylcarbonyl" refers to a heteroaryl group consisting of R a is a heteroaryl group as generally defined above, a Refers to the group.

[0041] The possible presence of one or more stereogenic centers in the compounds of formula (I) means that the compounds can be in optical isomeric form, i.e., enantiomeric or diastereomeric form. Also, atropisomers can occur due to the restriction of rotation about a single bond. Formula (I) is intended to include all these possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms and mixtures thereof of the compounds of formula (I). Similarly, formula (I) is intended to include all possible tautomeric forms. The present invention includes all possible tautomeric forms of the compounds of formula (I).

[0042] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example agriculturally usable salt form.

[0043] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds, as described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0044] The following list includes substituents R for compounds of formula (I): 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 For any one of these substituents, any of the definitions given below may be combined with any of the definitions of any other substituents given below or elsewhere in this specification.

[0045] R 1is hydrogen, cyano, formyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxyC1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, C1-C6 alkoxyC1-C3 alkoxycarbonyl, C1-C6 alkoxyoxalyl, C1-C6 alkoxycarbonylC1-C4 alkylC1-C6 alkoxycarbonyl, C1-C6 alkylsulfanylcarbonyl, or phenylcarbonyl. 1 is hydrogen, cyano, C1-C6 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxyC1-C3 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, or C1-C4 alkoxyC1-C2 alkoxycarbonyl. More preferably, R 1 is hydrogen, cyano, or C1-C6 alkylcarbonyl, and even more preferably is hydrogen, cyano, or C1-C3 alkylcarbonyl. 1 is hydrogen, cyano, or acetyl, and even more preferably is hydrogen or cyano. Most preferably, R 1 is hydrogen.

[0046] R 2 and R 3 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, halogen, or C1-C6 alkoxyC1-C2 alkyl. 2 and R 3 are each independently hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, halogen, or C1-C4 alkoxyC1-C2 alkyl. More preferably, R 2 and R 3 are each independently hydrogen, C1-C4 alkyl, or halogen. 2 and R 3 are each independently hydrogen, C1-C3 alkyl, or halogen. Even more preferably, R 2 and R 3are each independently hydrogen, methyl, ethyl or fluoro. 2 and R 3 are each independently hydrogen, methyl, or fluoro.

[0047] In one set of embodiments, R 2 and R 3 are both hydrogen. In another set of embodiments, R 2 and R 3 are both fluoro. In a further set of embodiments, R 2 and R 3 One of the is hydrogen, and the other is R 2 and R 3 One of the groups is methyl (e.g., R 2 When is hydrogen, R 3 is methyl, R 3 When is hydrogen, R 2 is methyl).

[0048] R 4 is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 (optionally substituted with 1 to 3 groups represented by the formula:), phenyl, phenyl C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclyl C1-C3 alkyl, where heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms or groups individually selected from nitrogen, oxygen, sulfur and S(O)2, where the heterocyclyl group is R 6or a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally containing 1, 2, 3, 4 or 5 heteroatoms individually selected from nitrogen, oxygen and sulfur, and optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker.

[0049] Preferably, R 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 (optionally substituted with one or two groups represented by the formula: phenyl, phenyl C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing one, two or three heteroatoms individually selected from nitrogen, oxygen and sulfur, heterocyclyl, heterocyclyl C1-C3 alkyl, where heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing one, two or three heteroatoms or groups individually selected from nitrogen, oxygen, sulfur and S(O)2, where the heterocyclyl group is R 6 or a 5- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system optionally containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker.

[0050] More preferably, R 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6(optionally substituted with one or two groups represented by the formula:) phenyl, phenylC1-C3 alkyl, heteroaryl (wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing one, two, or three heteroatoms individually selected from nitrogen, oxygen, and sulfur), heterocyclyl, heterocyclylC1-C3 alkyl (wherein heterocyclyl is a 4- to 6-membered non-aromatic monocyclic ring containing only one heteroatom or group individually selected from oxygen, sulfur, and S(O)2, where the heterocyclyl group is R 6 or a 6- to 10-membered non-aromatic spirocyclic carbobicyclyl ring system optionally containing 1 or 2 heteroatoms independently selected from nitrogen, oxygen and sulfur. Even more preferably, R 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C6 cycloalkyl, C3-C4 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 (Optionally substituted with 1 or 2 groups represented by the formula:), phenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl (wherein heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms or groups independently selected from oxygen, sulfur, and S(O)2, where the heterocyclyl group is R 6 or a 6- to 9-membered non-aromatic spirocyclic carbobicyclyl ring system optionally containing 1 or 2 heteroatoms individually selected from nitrogen, oxygen and sulfur. 4 is C3-C8 alkyl, C3-C6 cycloalkyl (wherein the cycloalkyl group is R 6 (Optionally substituted with 1 or 2 groups represented by the formula:) phenyl C1-C3 alkyl, heterocyclyl C1-C3 alkyl (wherein heterocyclyl is a 4-6 membered non-aromatic monocyclic ring containing only one heteroatom or group individually selected from oxygen, sulfur, and S(O)2, where the heterocyclyl group is a 4-6 membered non-aromatic monocyclic ring containing only one heteroatom or group individually selected from oxygen, sulfur, and S(O)2, where the heterocyclyl group is 6embedded image or phenyl C1-C3 alkyl.

[0051] In one set of embodiments, R 4 is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 embedded image optionally substituted with 1 to 3 groups represented by the formula: phenyl, phenyl C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl (wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur), heterocyclyl, heterocyclyl C1-C2 alkyl (wherein heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur), or a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur and optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker. 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6embedded image (optionally substituted with one or two groups represented by the formula: phenyl, phenyl C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl (wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur), heterocyclyl, heterocyclyl C1-C2 alkyl (wherein heterocyclyl is a 4-, 5-, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur), or a 5- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system optionally containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur, and optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker. More preferably, R 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 embedded image optionally substituted with one or two groups represented by the formula: phenyl, heteroaryl (wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing one, two, or three heteroatoms individually selected from nitrogen, oxygen, and sulfur), heterocyclyl (wherein heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen, oxygen, and sulfur), or a 6- to 10-membered non-aromatic spirocyclic carbobicyclyl ring system optionally containing one or two heteroatoms individually selected from nitrogen, oxygen, and sulfur. Even more preferably, R 4 is C1-C8 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C3-C4 cycloalkyl, C3-C4 cycloalkyl, C1-C2 alkyl (wherein the cycloalkyl group is R 6 or a 6- to 9-membered non-aromatic spirocyclic carbobicyclyl ring system optionally containing 1 or 2 heteroatoms individually selected from nitrogen, oxygen and sulfur. 4is C1-C6 alkyl or C3-C4 cycloalkyl, where the cycloalkyl group is R 6 It may be optionally substituted with one or two groups represented by:

[0052] In one set of embodiments, R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, isopentyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,1,3,3-tetramethylbutyl, n-hexyl, R 6 cyclopropyl, optionally substituted with one or two groups represented by 6 cyclobutyl, optionally substituted with one or two groups represented by 6 cyclopentyl optionally substituted with only one group represented by 6

[0033] is preferably cyclohexyl, 1-methyl-1-phenylethyl, 1-(1,1-dioxothian-4-yl)-1-methylethyl, 3-methyloxetan-3-yl, 3-methylthietan-3-yl, 3-methyltetrahydrofuran-3-yl, spiro[3.3]heptan-7-yl, spiro[3.4]octan-3-yl, spiro[3.4]octan-2-yl, spiro[3.5]nonan-2-yl, or 6,6-dimethyl-7-bicyclo[3.2.0]heptanyl, optionally substituted with only one group represented by 4 is t-butyl, isopentyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,1,3,3-tetramethylbutyl, 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 2,2-dimethylcyclobutyl, 1-methyl-1-phenylethyl, 1-(1,1-dioxothian-4-yl)-1-methylethyl, 3-methyloxetan-3-yl, 3-methylthietan-3-yl, 3-methyltetrahydrofuran-3-yl, spiro[3.3]heptan-7-yl, or spiro[3.4]octan-3-yl. More preferably, R 4is isopentyl, 2,2-dimethylpropyl, 1-methylcyclopropyl, or 2,2-dimethylcyclobutyl. Even more preferably, R 4 is isopentyl, 2,2-dimethylpropyl, 3-methyloxetan-3-yl, 1-methyl-1-phenylethyl, or 2,2-dimethylcyclobutyl.

[0053] In a further set of embodiments, R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, n-hexyl, R 6 cyclopropyl, optionally substituted with one or two groups represented by 6

[0036] Preferably, R is cyclobutyl, spiro[3.3]heptan-7-yl, spiro[3.4]octan-3-yl, spiro[3.4]octan-2-yl, spiro[3.5]nonan-2-yl, or 6,6-dimethyl-7-bicyclo[3.2.0]heptanyl, optionally substituted with one or two groups represented by 4 is t-butyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, 1-methylcyclopropyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl. More preferably, R 4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1-methylcyclopropyl, or 2,2-dimethylcyclobutyl. Even more preferably, R 4 is isopentyl, 2,2-dimethylpropyl, or 2,2-dimethylcyclobutyl.

[0054] R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl group is selected from R 7 Preferably, R is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from 5is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl group is selected from R 7 More preferably, R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen and sulfur, and wherein the phenyl or heteroaryl group is selected from R 7 Even more preferably, R 5 is phenyl, pyridyl, or isothiazolyl, where each phenyl, pyridyl, or isothiazolyl moiety is R 7 and optionally substituted by one or two substituents, which may be the same or different, selected from: 5 is phenyl or pyridyl, where each phenyl or pyridyl moiety is 7 may be optionally substituted by 1 or 2 substituents, which may be the same or different, selected from

[0055] In one set of embodiments, R 5 is phenyl, 3-fluorophenyl, 3-chlorophenyl, 3-methylphenyl, 3-methoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, pyridin-4-yl, 2-fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, pyridin-3-yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6-chloropyridin-3-yl, 5-chloropyridin-3-yl, or isothiazol-4-yl. 5is phenyl, 3-fluorophenyl, 3,5-difluorophenyl, 2,6-difluoropyridin-4-yl, or 5-chloropyridin-3-yl. Even more preferably, R 5 is phenyl, 3-fluorophenyl, 3,5-difluorophenyl, or 2,6-difluoropyridin-4-yl.

[0056] R 6 is halogen, C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 haloalkyl. 6 is chloro, fluoro, C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 haloalkyl. More preferably, R 6 is chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, isopropoxy, difluoromethyl or trifluoromethyl. Even more preferably, R 6 is chloro, fluoro, or methyl. Most preferably, R 6 is methyl.

[0057] R 7 is halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy. 7 is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy. More preferably, R 7 is chloro, fluoro, cyano, C1-C3 alkyl, C1-C3 haloalkyl, or C1-C3 alkoxy. Even more preferably, R 7 is chloro, fluoro, methyl, ethyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or isopropoxy. In one set of embodiments, R 7 is halogen, C1-C3 alkyl, or C1-C3 alkoxy, preferably R 7 is chloro, fluoro, methyl, or methoxy, more preferably fluoro or methyl, and most preferably R 7is methyl.

[0058] In the compounds of formula (I) according to the present invention, R 1 is hydrogen, cyano, or C1-C3 alkylcarbonyl; R 2 and R 3 are each independently hydrogen, C1-C3 alkyl, or halogen; R 4 is C1-C6 alkyl or C3-C4 cycloalkyl, where the cycloalkyl group is R 6 and optionally substituted with one or two groups represented by R 5 is phenyl, pyridyl, or isothiazolyl, where each phenyl, pyridyl, or isothiazolyl moiety is R 7 optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R 6 is methyl; R 7 is chloro, fluoro, methyl, or methoxy.

[0059] In another set of embodiments, R 1 is hydrogen or cyano; R 2 and R 3 are each independently hydrogen, methyl, or fluoro; R 4 is t-butyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, 1-methylcyclopropyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl; R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl group is selected from R 7optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R 7 is chloro, fluoro, methyl, or methoxy.

[0060] In a further set of embodiments, R 1 is hydrogen or cyano; R 2 and R 3 are each independently hydrogen, methyl, or fluoro; R 4 is C1-C6 alkyl or C3-C4 cycloalkyl, where the cycloalkyl group is R 6 and optionally substituted with one or two groups represented by R 5 is phenyl, pyridyl, or isothiazolyl, where each phenyl, pyridyl, or isothiazolyl moiety is R 7 optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R 6 is methyl; R 7 is methyl.

[0061] In yet a further set of embodiments, R 1 is hydrogen, cyano or acetyl; R 2 and R 3 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, halogen, C1-C6 alkoxyC1-C2 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, or oxetan-3-ylC1-C2 alkyl; R 4 is t-butyl, n-pentyl, isopentyl, 2,2-dimethylpropyl, 1-methylcyclopropyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl; R 5is phenyl, 3-fluorophenyl, 3-chlorophenyl, 3-methylphenyl, 3-methoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, pyridin-4-yl, 2-fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, pyridin-3-yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6-chloropyridin-3-yl, 5-chloropyridin-3-yl, or isothiazol-4-yl.

[0062] In yet another set of embodiments, R 1 is hydrogen or cyano; R 2 and R 3 are each independently hydrogen, methyl, or fluoro; R 4 is isopentyl, 2,2-dimethylpropyl, or 2,2-dimethylcyclobutyl; R 5 is phenyl, 3-fluorophenyl, 3,5-difluorophenyl, or 2,6-difluoropyridin-4-yl.

[0063] In one set of preferred embodiments, R 1 is hydrogen or cyano; R 2 and R 3 are each independently hydrogen, methyl, or fluoro; R 4 is 1,1-dimethylpropyl, 2,2-dimethylpropyl, isopentyl, 1,1,3,3-tetramethylbutyl, 2,2-dimethylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-methylthietan-3-yl, 3-methyloxetan-3-yl, 3-methyltetrahydrofuran-3-yl, 1-methyl-1-phenylethyl, or 1-(1,1-dioxothian-4-yl)-2-methylethyl; R 5is 3-fluorophenyl, 3,5-difluorophenyl, 2,6-difluoropyridin-4-yl, or 5-fluoropyridin-3-yl.

[0064] In a further set of preferred embodiments, R 1 is hydrogen or cyano; R 2 and R 3 are each independently hydrogen or methyl; R 4 is 2,2-dimethylpropyl, isopentyl, 2,2-dimethylcyclopropyl, 3-methyloxetan-3-yl, or 1-methyl-1-phenylethyl; R 5 is 3-fluorophenyl, 2,6-difluoropyridin-4-yl, or 5-fluoropyridin-3-yl.

[0065] Preferably, the compound according to formula (I) is selected from compounds P-1 to P-26 shown in Table 3 (below). More preferably, the compound according to formula (I) is 6-anilino-N-(2,2-dimethylpropyl)-2-methyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-1), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-2-methyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-3), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-4), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-5), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-6), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-7), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-8), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-2,2-difluoro-[1,3]dioxolo[ Lysine-4-carboxamide (P-6), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-13), N-(2,2-dimethylpropyl)-6-(3-fluoroanilino)-2-methyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-2), 6-(N-cyano-3,5-difluoro-anilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[ 4,5-c]pyridine-4-carboxamide (P-7), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-10), 6-[(2,6-difluoro-4-pyridyl)amino]-N-isopentyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-12), N-(2,2-dimethylpropyl)-6-[(5-fluoro-3-pyridyl)amino]-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide Solo[4,5-c]pyridine-4-carboxamide (P-14), 6-(3,5-difluoroanilino)-N-(1-methyl-1-phenyl-ethyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(3-methyloxetan-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-24), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-5), 6-anilino-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-9), N-(2,2-dimethylpropyl)-6-(3-fluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-15), 6-(3,5-difluoroanilino)-N-(1,1,3,3-tetramethylbutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide 6-(3,5-difluoroanilino)-N-(3-methyltetrahydrofuran-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-23), 6-(3,5-difluoroanilino)-N-(1-methylcyclohexyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-26), N-(2,2-dimethylcyclobutyl)-6-(3-fluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide amide (P-8), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-11), 6-(3,5-difluoroanilino)-N-(1,1-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-18), 6-(3,5-difluoroanilino)-N-(3-methylthietan-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P -19), N-tert-butyl-6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-21), 6-(3,5-difluoroanilino)-N-(1-methylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-22), and 6-(3,5-difluoroanilino)-N-(1-methylcyclopentyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-25).

[0066] Even more preferably, the compound according to formula (I) is N-(2,2-dimethylpropyl)-6-(3-fluoroanilino)-2-methyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-2), 6-(N-cyano-3,5-difluoro-anilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-7), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine 6-[(2,6-difluoro-4-pyridyl)amino]-N-isopentyl-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-12), N-(2,2-dimethylpropyl)-6-[(5-fluoro-3-pyridyl)amino]-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-14), 6-(3,5-difluoroanilino)-N-(1-methyl-1-phenyl-ethyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-20) ), 6-(3,5-difluoroanilino)-N-(3-methyloxetan-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-24), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-5), 6-anilino-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-9), N-(2,2-dimethylpropyl)-6-(3-fluoroanilino) -[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-15), 6-(3,5-difluoroanilino)-N-(1,1,3,3-tetramethylbutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-17), 6-(3,5-difluoroanilino)-N-(3-methyltetrahydrofuran-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-23), 6-(3,5-difluoroanilino)-N-(1-methylcyclohexyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-26), N-(2,2-dimethylcyclobutyl)-6-(3-fluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-8), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-11), 6-(3,5-difluoroanilino)-N-(1,1-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-18), 6-(3,5-difluoroanilino)-N-(3-methyl Thietan-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-19), N-tert-butyl-6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-21), 6-(3,5-difluoroanilino)-N-(1-methylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-22), and 6-(3,5-difluoroanilino)-N-(1-methylcyclopentyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-25).

[0067] More preferably, the compound according to formula (I) is P-24), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-5), 6-anilino-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-9), N-(2,2-dimethylpropyl)-6-(3-fluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-15), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-16), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-17), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-18), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-19), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-21), 6- 6-(3,5-difluoroanilino)-N-(3-methyltetrahydrofuran-3-yl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-23), 6-(3,5-difluoroanilino)-N-(1-methylcyclohexyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-26), N-(2,2-dimethylcyclobutyl)-6-(3-fluoroanilino)-N-(1,1,3,3-tetramethylbutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-27), 6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-8), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-11), 6-(3,5-difluoroanilino)-N-(1,1-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-18), 6-(3,5-difluoroanilino)-N-(3-methylthietan-3-yl)-[1,3]dioxolo[4,5 -c]pyridine-4-carboxamide (P-19), N-tert-butyl-6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-21), 6-(3,5-difluoroanilino)-N-(1-methylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-22), and 6-(3,5-difluoroanilino)-N-(1-methylcyclopentyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-25).

[0068] More preferably, the compound according to formula (I) is N-(2,2-dimethylcyclobutyl)-6-(3-fluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-8), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-11), 6-(3,5-difluoroanilino)-N-(1,1-dimethylpropyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-18), 6-(3,5-difluoroanilino)-N-(3-methylthieno)- N-tert-butyl-6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-19), N-tert-butyl-6-(3,5-difluoroanilino)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-21), 6-(3,5-difluoroanilino)-N-(1-methylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-22), and 6-(3,5-difluoroanilino)-N-(1-methylcyclopentyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (P-25).

[0069] The compounds of the present invention can be formed as shown in the following schemes, in which, unless otherwise specified, the definitions of each variable are as defined above for compounds of formula (I), and can be prepared as shown in the following schemes.

[0070] R 1 , R 2 , R 3 , R 4 and R 5 The compounds of formula (I) according to the present invention, wherein R is as defined in formula (I), can be converted to compounds of formula (III), wherein R is either by heating or under base-assisted or transition metal catalyzed Buchwald-Hartwig amination conditions. 1 and R 5is as defined in formula (I) with a compound of formula (II) (wherein R 2 , R 3 and R 4 is as defined in formula (I), and R 11 is a halogen, preferably chloro), to the compound, which is shown in Scheme 1 below. Scheme 1 [ka]

[0071] The Buchwald-Hartwig reaction is well known to those skilled in the art and is a chemical reaction used in organic chemistry for the synthesis of carbon-nitrogen bonds by palladium-catalyzed coupling reaction of aryl amines with heteroaryl halides. Such reactions are reported, for example, in ACS Catal., 2019, 3822-3830 and references cited therein. The reaction typically involves a palladium catalyst, such as Pd(OAc)2, Pd2(dba)3, and a ligand, such as diphenylphosphino binaphthyl (BINAP) and diphenylphosphinoferrocene (DPPF), as well as xantphos. More modern methods of the Buchwald-Hartwig coupling reaction include the use of a palladium precatalyst, such as BrettPhos Pd G3 (CAS[1470372-59-8]) or RuPhos Pd G3 (CAS[1445085-77-7]), which ensures efficient and rapid generation of active catalytic species. The reaction requires the presence of a base such as alkaline earth metal alkoxides and hydroxides, e.g. potassium or sodium t-butoxide or hydroxide, alkaline earth metal carbonates such as sodium or cesium carbonate, and organic bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction is carried out in a variety of inert solvents such as THF, water, toluene, dioxane, and DMF and / or mixtures thereof at temperatures between 20 and 170 °C (Buchwald, SLChem. Rev., 2016.116(19), 12564). The reaction is carried out in the presence of a base such as alkaline earth metal alkoxides and hydroxides, e.g. potassium or sodium t-butoxide or hydroxide, alkaline earth metal carbonates such as sodium or cesium carbonate, and organic bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction is carried out in a variety of inert solvents such as THF, water, toluene, dioxane, and DMF and / or mixtures thereof at temperatures between 20 and 170 °C (Buchwald, SLChem. Rev., 2016.116(19), 12564). 1It is particularly advantageous if is hydrogen.

[0072] R 2 , R 3 and R 4 is as defined in formula (I), and R 11 Compounds of formula (II), where R is halogen, preferably chloro, can be converted to compounds of formula (V), where R is an alkyl group, either by heating or with the aid of a base, preferably cesium carbonate or potassium carbonate. 2 and R 3 is as defined in formula (I), and R 12 is halogen, preferably chloro) with a compound of formula (IV) 4 is as defined in formula (I), and R 11 is a halogen, preferably chloro), to the compound, which is shown in Scheme 2 below. Scheme 2 [ka]

[0073] The alkylation cyclization reactions shown above are well known to those skilled in the art and reported examples for related substrates can be found in WO 17119700 or Tetrahedron Lett., 1976, 38, 3361 and Tetrahedron, 1964, 20, 1725.

[0074] R 4 is as defined in formula (IV), and R 11 Compounds of formula (IV), where R is halogen, preferably chloro, can be converted to compounds of formula (VI) (R 1 ) with a dealkylating agent, preferably pyridinium chloride or boron tribromide, with or without heating. 4 is as defined in formula (IV), R 11 is a halogen, preferably chloro), which is shown in Scheme 3 below. Scheme 3 [ka]

[0075] Dealkylation reactions are well known to those skilled in the art, and examples of reports on related substrates can be found in Bioorg. Med. Chem., 2011, 19, 4935 or Bioorg. Med. Chem. Lett. 2000, 10, 1365.

[0076] R 4 is as defined in formula (I), and R 11 is halogen, preferably chloro, and R 13 Compounds of formula (VI), where R is alkyl, preferably methyl, can be converted to compounds of formula (VII), where R is an alkyl group, by halogenating agents, preferably N-chlorosuccinimide, N-bromosuccinimide or bromine. 4 is as defined in formula (I), and R 13 can be obtained by conversion of a compound of formula (III) in which R is an alkyl group, preferably methyl. Scheme 4 [ka]

[0077] Electrophilic aromatic halogenation is well known to those skilled in the art and examples of reports on related substrates can be found in Bioorg.Med.Chem.Lett., 2013, 23, 5953 or Bioorg.Med.Chem.Lett., 2011, 21, 6705. This is shown in Scheme 4 below.

[0078] R 4 is as defined in formula (I), and R 13 Compounds of formula (VII), where R is alkyl, preferably methyl, can be converted to compounds of formula (IX), where R is an acylating agent, via an intermediate acid chloride or an activated acylating agent as described below. 4 is as defined in formula (I) with a compound of formula (VIII) (wherein R 13is an alkyl, preferably methyl) compound, which is shown in Scheme 5 below. Scheme 5 [ka]

[0079] As shown in Scheme 5, compound (VII) is activated to compound of formula (IV) by methods known to those skilled in the art and described, for example, in Tetrahedron, 61(46), 10827-10852, 2005. For example, compounds of formula (IV) where V0 is halogen are formed by treatment of compound of formula (VII) with, for example, oxalyl chloride or thionyl chloride in the presence of catalytic amount of DMF in an inert solvent such as methylene dichloride or THF at a temperature between 25 and 170° C., preferably between 25 and 80° C. Compound of formula (X), where R 4 Treatment of a compound of formula (IX) with a compound of formula (IX) (wherein R is as defined in formula (I)) affords a compound of formula (VII).

[0080] Alternatively, the compound of formula (VII) can be converted to an activated species (IX), where X is X, in an inert solvent, such as pyridine or THF, optionally in the presence of a base, such as triethylamine, at a temperature between room temperature and 180° C. 01 Or X 02 In addition, the acids of formula (VIII) can also be activated by reaction with coupling reagents such as propanephosphonic anhydride (T3P®) or HATU to give the compounds of formula (IX), where X0 is X, as described, for example, in Synthesis 2013, 45, 1569 and Journal Prakt. Chemie 1998, 340, 581. 03 Or X 04Subsequent reaction with an amine of formula X can provide a compound of formula (VII). [ka]

[0081] Surprisingly, it has now been found that the novel compounds of formula (I) have, for practical purposes, a highly advantageous level of biological activity which protects plants against diseases caused by fungi.

[0082] The compounds of formula (I) can be used in the agricultural sector and related fields of use, for example as active ingredients for the control of plant pests or non-living materials, for the control of spoilage microorganisms or organisms potentially harmful to humans. The novel compounds are distinguished by their excellent activity at low application rates, their excellent tolerance by plants, and their safety for the environment. They have highly useful curative, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of formula (I) can be used to inhibit or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time also protecting these parts of later-growing plants from, for example, phytopathogenic microorganisms.

[0083] The present invention further relates to a method for controlling or preventing infestation of susceptible plants or plant propagation material and / or harvested food crops by microorganisms by treating the plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound of formula (I) is applied to the plant, part thereof or its habitat.

[0084] The compounds of formula (I) may also be used as fungicides. The term "fungicide" as used herein means a compound that controls, modifies or prevents fungal growth. The term "fungicidally effective amount" means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. A controlling or modifier effect includes any deviation from natural development such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent infection by the fungus.

[0085] The compounds of formula (I) can also be used as dressings to treat plant propagation material, such as seeds, for example fruits, tubers or grains, or plant cuttings (e.g. rice), for protection against fungal infections occurring in the soil, as well as against phytopathogenic fungi. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: for example, seeds can be dressed before being sown.

[0086] The active ingredients of the invention can also be applied to grains (coating) by impregnating the seeds in a liquid formulation or coating the seeds with a solid formulation. The compositions can also be applied to the planting site when the propagation material is planted, for example in the sowing furrow during sowing. The invention also relates to a method for treating such plant propagation material and to the plant propagation material thus treated.

[0087] Furthermore, the compounds according to the invention can be used for controlling fungi in related fields such as the protection of industrial materials, including wood and wood-based industrial products, food storage and hygiene control.

[0088] In addition, the present invention can be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0089] The compounds of formula (I) may be effective against, for example, disease-related fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, such as, for example: The fungi and fungal vectors associated with these diseases, as well as the phytopathogenic bacteria and viruses which can be controlled, are, for example: Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, lactucae, B. dothidea, B. obtusa, Botryosphaeria spp. including B. cinerea, C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Candida spp., Cephaloascus fragrans, Ceratocystis spp. spp., Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Erysiphe spp., including Epidermophyton spp., Erwinia amylovora, and E. cichoracearum; Fusarium spp. including Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp. spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including M. graminicola and M. pomi.), Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, P.Puccinia spp., including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp., including P. oryzae, Pythium spp., including P. ultimum, Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arizus, arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, . Sclerotinia spp., Sclerotium spp., Septoria spp. including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola basicola, Tilletia spp., Trichoderma spp. including T. harzianum, T. pseudokoningii, and T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. including V. inaequalis, Verticillium spp. and Xanthomonas spp.

[0090] Within the scope of the present invention, the target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; and arable plants, such as bermuda grass, strawberry bush, bentgrass, centipede grass, fescue, ryegrass, lawn grass and wild grass. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines, for example grapes.

[0091] The term "useful plants" should also be understood to include useful plants in which resistance to herbicides such as bromoxynil or to a class of herbicides (e.g. HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc.) has been provided by conventional breeding or genetic engineering methods. An example of a crop in which resistance to imidazolinones, e.g. imazamox, has been provided by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered resistant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0092] The term "useful plants" should also be understood to include useful plants which have been transformed by recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, in particular those of the genus Bacillus.

[0093] Examples of such plants are: YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Root Feeders® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing a CryIA(b) and a CryIIIB(b1) toxin); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing a VIP toxin); NewLeaf® (a potato variety expressing a CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn root-feeding nematode trait) and Protecta®.

[0094] The term "crop plant" should also be understood to include crop plants which have been transformed using recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those of the genus Bacillus.

[0095] Toxins which can be expressed by the transformed plant include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from Photorhabdus spp. or Xenorhabdus spp., for example Photorhabdus luminescens, Xenorhabdus nematophilus. spp.); toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0096] In the context of the present invention, delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, are to be understood as being especially hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by new combinations of different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0097] Examples of such toxins or transformed plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0098] The processes for the preparation of such transformed plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0099] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0100] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include: YieldGard® (a corn variety expressing Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing Cry9C toxin); Herculex I® (a corn variety expressing Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0101] Further examples of such transformed crops are as follows: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. A genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0102] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. A genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of the Cry1Ab toxin. Bt176 maize also transgenicly expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0103] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transformed maize plants is described in WO 03 / 018810.

[0104] 4. MON863 maize, registration number C / DE / 02 / 9, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the Cry3Bb1 toxin and confers resistance to certain coleopteran insects.

[0105] 5. IPC531 Cotton made by Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0106] 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain lepidopteran insects, and for expression of the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0107] 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. It consists of a conventional hybrid maize variety by crossing the genetically engineered varieties NK603 and MON810. NK603 x MON810 maize transgenic expresses the protein CP4 EPSPS from the strain CP4 of Agrobacterium sp., which confers resistance to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0108] Further, to date, it has been discovered that compounds of formula (I) (including any one of the compounds set out in Table 3 (below)) can be used in combination with Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp., including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp., including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp., including C. arachidicola, and Cercospora spp.), Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp. spp., Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Fusarium spp. including F. solani, F. spp.), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum, Laetisaria spp. fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., M. graminicola, Mycosphaerella spp. including M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp. Penicillium spp., including P. digitatum, P. italicum, Petriellidium spp., P. maydis, P. philippinensis and P. sorgii.Peronosclerospora spp. including P. sorghi, Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola spp., Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis, P. humuli ... Puccinia spp. including P. tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum), Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp., including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Septoria spp., including S. nodorum, S. tritici spp., Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp. spp., Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. including V. inaequalis.), Verticillium spp., and Xanthomonas spp., in particular Zymoseptoria tritici, Puccinia recondita, Puccinia striiformis, Erysiphe graminis, Uncinula necator, Sphaerotheca fuliginea, Leveillula taurica, Phakopsora pachyrhizi, Pyricularia oryzae, Alternaria solani, Alternaria alternata, alternata, Mycosphaerella fijiensis, Colletotrichum lagenarium, Didymella bryoniae, Ascochyta pisii, Verticillium dahliae, Pyreno. No cross-resistance has been observed between any of the fungicidal solutions used to control phytopathogenic fungi such as Cercospora teres, Cercospora beticola, Ramularia collo-cygni, Botrytis cinerea, Sclerotinia sclerotiorum, Monilinia laxa, Monographaella nivalis and Venturia inaequalis.

[0109] Indeed, fungicidal resistant strains of any of the species as outlined above have been reported in the scientific literature with strains resistant to one or more fungicides from at least one of the following fungicidal modes of action: quinone outside inhibitors (QoI), quinone inside inhibitors (QiI), succinate dehydrogenase inhibitors (SDHI) and sterol demethylase inhibitors (DMI). Such fungicidal resistant strains may include: - A mutation in the mitochondrial cytochrome b gene that confers resistance to Qo inhibitors, the mutation being G143A, F129L or G137R. See, for example: Gisi et al., Pest Manag Sci 56, 833-841 (2000); Lucas, Pestic Outlook 14(6), 268-70 (2003); Fraaije et al., Phytopathol 95(8), 933-41 (2005); Sierotzki et al., Pest Manag Sci 63(3), 225-233 (2007); Semar et al., Journal of Plant Diseases and Protection(3), 117-119 (2007); and Pasche et al., Crop Protection 27(3-5), 427-435 (2008). • A heterozygous mutation in the mitochondrial cytochrome b gene that confers resistance to Qi inhibitors, where the mutation is G37A / C / D / S / V. See for example: Meunier et al., Pest Manag Sci 2019;75:2107-2114. • Mutations in genes encoding the SdhB,C,D subunits that confer resistance to SDHI inhibitors, where the mutations are present in the major pathogens of: ○ Botrytis cinerea: B-P225H / L / T / Y / F, B-N230I, B-H272L / Y / R, C-P80H / L, C-N87S; Alternaria solani: B-H278R / Y, C-H134R / Q, D-D123E, D-H133R and C-H134R; ○ Wheat leaf blight fungus (Zymoseptoria tritici): sdhB:N225T, N225I, R265P, T268I, T268A.In sdhC:T79N, T79I, W80S, W80A, A84F, N86S, N86A, P127A, R151M / S / T / G, R151S, R151T, H152R / Y, V166M, T168R.In sdhD:I50F, M114V, D129G, T20P+K186R; Pyrenophora teres: In sdhB: S66P, N235I, H277Y. In sdhC: K49E, R64K, N75S, G79R, H134R, S135R. In sdhD: D124E, H134R, G138V, D145G; ○ Ramularia collo-cygni:In sdhB:N224T, T267I.In sdhC:N87S, G91R, H146R / L, G171D, H153R; Phakopsora pachyrhizi: C-I86F; ○ Sclerotinia sclerotiorum:In sdhB:H273Y.In sdhC:G91R, H146R.In sdhD:T108K, H132R, G150R A mutation in.

[0110] The main sources of information are www.frac.info, Sierotzki and Scalliet Phytopathology (2013) 103(9):880-887 and Simoes et al., J Plant Dis Prot (2018) 125:21-2. ● Mutations or combinations of mutations in the CYP51 gene conferring resistance to DMI inhibitors, where the mutations are L50S, D134G, V136A / C, Y137F, S188N, A379G, I381V, deletions 459-460, Y461H / S, N513K, S524T. Primary sources of information are www.frac.info, Cools et al., Plant Pathol (2013) 62:36-42 and Schmitz HK et al., Pest Manag Sci (2014) 70:378-388.

[0111] Thus, in a preferred embodiment, a compound of formula (I) comprising any one of the compounds set out in Table 3 (below), or a fungicidal composition according to the invention comprising a compound of formula (I), is used to control fungal strains which are resistant to one or more fungicides from any of the following fungicidal MoA classes: quinone outside inhibitors (QoIs), quinone inside inhibitors (QiIs), succinate dehydrogenase inhibitors (SDHIs) and sterol demethylase inhibitors (DMIs).

[0112] As used herein, the term "habitat" refers to the field in which the plant is growing or in which the seeds of the cultivated plant have been sown or in which the seeds will be sown in the soil, including the soil, the seeds and seedlings, as well as the established vegetation.

[0113] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage and fruits.

[0114] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, which can be used for their propagation, and vegetative bodies, such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts may be mentioned. Also mentioned are sprouted plants and shoots that are to be transplanted after germination or emergence from the soil. These shoots may be protected by a complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0115] The pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0116] The compounds of formula (I) can be used in their pure form or, preferably, together with the auxiliaries that are conveniently employed in the art of formulation.For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and capsules, for example, in polymeric materials.As well as the type of composition, the application method, such as spraying, misting, dusting, scattering, coating, or pouring, is selected according to the intended purpose and the current situation.The composition may also contain further auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders or adhesives, as well as fertilizers, sources of trace elements, or other compounds for obtaining special effects.

[0117] Suitable carriers and adjuvants, for example for use in agriculture, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0118] The compounds of formula (I) are usually used in the form of compositions and can be applied to the crop area or plants to be treated simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these preparations, if desired with further carriers, surfactants or application-promoting adjuvants customarily used in the field of formulations.

[0119] The compounds of formula (I) may be used in the form of a (fungicidal) composition for the control or protection against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or at least one of the preferred individual compounds as defined above, in free form or in the form of an agrochemically usable salt, and at least one of the adjuvants described above.

[0120] 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, the composition may comprise, in addition to the compound of formula (I), at least one pesticidal active compound, for example an additional fungicidal active ingredient.

[0121] The compound of formula (I) may be the sole active ingredient in the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic activity.

[0122] Examples of suitable additional active ingredients are the following: acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, Morpholine fungicides and fungicides, organophosphate fungicides and fungicides, organotin fungicides and fungicides, oxathiin fungicides and fungicides, oxazole fungicides and fungicides, phenylsulfamide fungicides and fungicides, polysulfide fungicides and fungicides, pyrazole fungicides and fungicides, pyridine fungicides and fungicides, pyrimidine fungicides and fungicides, pyrrole fungicides and fungicides, quaternary ammonium fungicides and fungicides, quinoline fungicides and fungicides, quinone fungicides and fungicides, quinoxaline fungicides These include fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0123] Examples of suitable additional active ingredients also include: petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-cinnamaldehyde, 4-chlorophenyl phenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate, bromobenzo ... Mocyclene, Bromophos, Bromopropylate, Buprofezin, Butocarboxim, Butoxycarboxim, Butylpyridaben, Calcium polysulfate, Camphechlor, Carbanolate, Carbophenothione, Cymiazole, Tinomethionate, Chlorbeneside, Chlordimeform, Chlordimeform hydrochloride, Chlorphenetole, Chlorphenson, Chlorphenesulfide, Chlorobenzilate, Chlormebuform, Chlormethiuron, Chloropropylate, Chlorthiophos, Cinerin I, Cinerin II, Cinerins, Closantel, Kumafo s, crotamiton, crotoxyphos, kufraeb, cyanthoate, DCPM, DDT, demefion, demefion-O, demefion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulfone, dichlofluanid, dichlorvos, dicrifos, dienochlor, dimefox, ginex, ginex-diclexin, dinocap-4, dinocap-6, dinokton, dinopenton, dinosulfone, dinotervone, dioxathion, diphenylsulfone, disulfiram, DNOC, Dofenapine, doramectin, endothion, epirimectin, ethoeate methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formoparanate, gamma-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I,Jasmolin II, Jodofenphos, Lindane, Malonoben, Mecarbam, Mefosfolan, Mesulfen, Methacrifos, Methyl bromide, Metolcarb, Mexacarbate, Milbemycin oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Nifluridide, Nikkomycin, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, Omethoate, Oxydeprophos, Oxydisulfoton, pp'-DDT, Parathion, Permethrin, Fencapton, Phosalone, Phosphorane, Phosphamidon, Polychloroterpenes, Polynactin, Proc Ronol, Promacyl, Propoxur, Prothidathion, Prothoate, Pyrethrin I, Pyrethrin II, Pyrethrin, Pyridafenthion, Pirimitate, Quinalphos, Quinthiophos, R-1492, Phosglycine, Rotenone, Shladan, Cebufos, Selamectin, Sofamid, SSI-121, Sulfiram, Sulfuramide, Sulfotep, Sulfur, Diflovidazin, Tau-Fulvalinate, TEPP, Terbam, Tetradifon, Tetrasulf, Thiafenox, Thiocarboxim, Thiofanox, Thiofanox, Thio Meton, thioquinox, thuringiensin, triamiphos, triatene, triazophos, triazuron, triphenofos, trinactin, vamidothion, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, sibutrin, dichloron, dichlorophen, endothal, fentin, hydrated lime, nerbam, quinoclamine, quinoneamide, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine , strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, doditin, phenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate,Probenazole, Streptomycin, Streptomycin sesquisulfate, Tecloftalam, Thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae,Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii lecanii), apholate, bisadil, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, molzide, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en-1-yl acetate + (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)-icos-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)-dodeca-7,9-dien-1-yl acetate,(9Z,11E)-Tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-Tetradeca-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol + 4-methylnonan-5-one, α-multistriatin, brevicomin, codrel, codremon, querle, disparlure, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, fumaric acid Rontalin, Grandolure, Grandolure I, Grandolure II, Grandolure III, Grandolure IV, Hexalure, Ipsdienol, Ipsenol, Japonilure, Lineatin, Littleua, Louplure, Medulure, Megatomoic acid, Methyleugenol, Muscalure, Octadeca-2,13-dien-1-yl acetate, Octadeca-3,13-dien-1-yl acetate, Olfular, Orictalure, Ostramon, Siglua, Soldidin, Sulcatol, Tetradec-11-en-1-yl acetate, Trimedulure, Trimedulure A, Trimedulure Rimedlure B1, Trimedlure B2, Trimedlure C, trunc-call, 2-(octylthio)ethanol, butapyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyl toluamide, dimethylcarbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1, 2-Dichloropropane + 1,3-dichloropropene, 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 dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate,2-Imidazolidone, 2-Isovalerylindan-1,3-dione, 2-Methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-Thiocyanatoethyl laurate, 3-Bromo-1-chloroprop-1-ene, 3-Methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-Methyl(prop-2, -ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, alixycarb, α-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis (Bacillus thuringiensis) delta endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, sodium borate, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebazine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlor Prazophos, cis-resmethrin, cismethrin, clocithrin, copper acetoarsenite, copper arsenate, copper oleate, cumitoate, cryolite, CS708, cyanofenphos, cyanophos, ciclethrin, cithioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dicapton, dichlorophenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethylan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, dichloroethane, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarboxylate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikincarb,IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kereban, kinoprene, lead arsenate, leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menazone, mercurous chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methoclotophos, methoprene, methothrin, methoxychlor, methylisothiocyanate ester, methyl chloroform, methylene chloride, methoxadiazone, mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethyl phosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichloro Benzene, Parathion-methyl, Pentachlorophenol, Pentachlorophenyl Laurate, PH60-38, Fenkapton, Phosnichlor, Phosphine, Phoxim-methyl, Pyrimetaphos, Polychlorodicyclopentadiene Isomers, Potassium Arsenite, Potassium Thiocyanate, Precocene I, Precocene II, Precocene III, Pyrimidophos, Profluthrin, Promecarb, Prothiophos, Pyrazophos, Pyresmethrin, Cassia, Quinalphos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Cadethrin, Riania, Ri Anodine, Sabadila), Shradan, Cebufos, SI-0009, Thiapronil, Sodium arsenite, Sodium cyanide, Sodium fluoride, Sodium hexafluorosilicate, Sodium pentachlorophenoxide salt, Sodium selenate, Sodium thiocyanate, Sulcofuron, Sulcofuron-sodium, Sulfuryl fluoride, Sulprofos, Tall oil, Thionazine, TDE, Tebupirimfos, Temephos, Telarethrin, Tetrachloroethane, Cyclofos, Thiocyclam, Thiocyclam hydrogen oxalate, Thionazine, Thiosultap,Thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormethaphos-3, trichloronat, trimethacarb, tolprocarb, triclopyricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprophos, and meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2- Dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-anime, benclothiaz, cytokinin, DCIP, rufural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis) extract, α-chlorohydrin, anth, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciriloside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol + nerolidol, berubutin, MGK 264, piperonyl butoxide, piperotal, propyl isomer, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram,Imanin, ribavirin, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, Pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofrace, oxadixyl, carbendazim, debacarb, Fuberidazole, thiabendazole, chlozolinate, diclozolin, mycrozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, oryzastrobin, picoxystrobin, pyraclostrobin , pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine copper, nitrothal-isopropyl, edifenphos, iprobenfos, phosdifen, turcophos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine, dicloran,Diethofencarb, dimethomorph, flumorph, dithianone, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, fluopicolide, flusulfamide, fluxapyroxad, fenhexamid, fosetyl-aluminum, hymexazole, iprovalicarb, cyazofamid, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil , triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, fluveneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isotianil, dipimethitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(di fluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluoro-phenyl)-N -(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), lvbenmixianan, diclobenthiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline,t-Butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, impirfluxam, tulorprocarb, mefentrifluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R), -3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]- 3-Chloro-phenyl]methanesulfonic acid, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylin 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, amethoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2- Methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, tebufloquine, ipurfenoquine, quinofumelin, isofetamide, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, fenamacril, 5-amino-1,3,4-Thiadiazole-2-thiol zinc salt (2:1), fluopyram, flutianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1, 1-Difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproly 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, cumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amectotractin, iprodione, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-Diamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro- 3,3-Dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline isoquinoline (these compounds can be prepared from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benz imidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl ]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-( N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds are disclosed in International Publication No. WO 2017 / 05 / 04362, the disclosure of which is incorporated herein by reference in its entirety) 5473, 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 methods described in WO 2017 / 029179), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by the methods described in WO 2017 / 029179), 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), ]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290), 4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (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']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared by the method described in WO 2011 / 138281). N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2018 / 153707), N'-(2-chloro-5 -methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in WO 2016 / 202742), 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675);(5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the methods described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate acetamide (which may be prepared from the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (which may be prepared from the method described in WO 2018 / 202428);

[0124] The compounds of the present invention may also be used in combination with anthelmintic drugs. Such anthelmintics include compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, epirimectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP 357460, EP 444964 and EP 594291. Additional anthelmintics include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US Pat. No. 5,015,630, WO 9415944 and WO 9522552. Additional anthelmintics include benzimidazoles, such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxyfendazole, oxybendazole, parbendazole and other members of this class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintics include fluoxides such as triclabendazole and clorsulon, and cestocides such as praziquantel and epsiprantel.

[0125] The compounds of the present invention may be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintics, as well as antiparasitic oxazolines such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 and German Patent No. 19520936.

[0126] The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents described in WO 9615121, and in combination 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.

[0127] The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0128] The compounds of the present invention may be used in combination with terpene alkaloids, particularly those disclosed in WO 95 / 19363 or WO 04 / 72086.

[0129] Other examples of such biologically active compounds with which the compounds of the present invention may be used in combination include, but are not limited to, the following: Organophosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Cadusafos, Chlorethoxyphos, Chlorpyrifos, Chlorfenvinphos, Chlormephos, Demeton, Demeton-S-methyl, Demeton-S-methylsulfone, Diarifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Ethoprophos, Etrimphos, Fanfur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonophos, Formothion, Fosthiazate, Heptenophos, Isazophos, Isothioate, Isoxathioate , malathion, methacrifos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proethamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.

[0130] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

[0131] Pyrethroids: acrinathin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin , cycythrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, λ-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, θ-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, ζ-cypermethrin.

[0132] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentadine; b) Ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) Juvenoids: Pyriproxyfen, Methoprene (including S-methoprene), Fenoxycarb; d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0133] Other antiparasitic drugs: Acequinocyl, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis thuringiensis), bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloride, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, fluphenzin, flufenprox, fluproxifen, halofenprox ofenprox), hydramethylnon, IKI-220, Kanemite, NC-196, Nimgard, Nidinolterfuran, Nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymethrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin, belbutin, bertarek, YI-5301.

[0134] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0135] Fungicides: Chlortetracycline, oxytetracycline, streptomycin.

[0136] Other biological agents: Enrofloxacin, Febantel, Penethamate, Moroxicam, Cephalexin, Kanamycin, Pimobendan, Clenbuterol, Omeprazole, Tiamulin, Benazepril, Pyriprole, Cefquinome, Florfenicol, Buserelin, Cefovecin, Tulathromycin, Ceftiowol, Carprofen, Metaflumizone, Praziquarantel, Triclabendazole.

[0137] Another aspect of the invention relates to the use of a compound of formula (I) or a preferred 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 comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as defined above, for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation products, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic microorganisms, e.g. insects or preferably fungal organisms.

[0138] A further aspect of the invention relates to a method for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation materials, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material, by insects or spoilage microorganisms or organisms that are phytopathogenic or potentially harmful to humans, particularly fungal organisms, which method comprises the step of applying a compound of formula (I) or a preferred individual compound as defined above, as an active ingredient, to the plant, to a part of the plant or its habitat, to its propagation materials, or to any part of the non-living material.

[0139] By control or prevention is meant the reduction of infestation by insects or by spoilage microorganisms or organisms that are plant pathogenic or potentially harmful to humans, particularly fungal organisms, to a level that demonstrates improvement.

[0140] A preferred method for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which involves the application of a compound of formula (I) or an agrochemical composition containing at least one of said compounds, is foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compound of formula (I) can also be introduced into the plant by the roots via the soil (systemic action) by irrigating the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, for example in granular form (soil application). In the case of rice crops, such granules can be applied to flooded rice fields. The compound of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0141] Formulations, e.g. compositions containing a compound of formula (I) and, if desired, a solid or liquid auxiliary or monomer that encapsulates the compound of formula (I), may be prepared in a known manner, typically by homogeneously mixing and / or grinding the compounds together with extenders, e.g. solvents, solid carriers and optionally surface-active compounds (surfactants).

[0142] Advantageous application rates are usually from 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably from 10 g to 1 kg ai / ha, most preferably from 20 g to 600 g ai / ha.When used as a seed drench, a convenient dosage is from 10 mg to 1 g of active substance per kg of seeds.

[0143] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0144] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), sorbent granules (RM ... The present invention may be employed in the form of an emulsion, such as an EG, an emulsion, a water-in-oil (EO), an emulsion, an oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), a very low volume suspension (SU), a very low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any technically desirable formulation in combination with an agriculturally acceptable adjuvant.

[0145] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with suitable inert ingredients (diluents, solvents, fillers, and optionally other ingredients such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds that provide adjuvant activity effects). Conventional slow-release formulations can also be employed when long-lasting efficacy is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvant effects, such as, for example, condensates of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0146] The seed dressing formulation is applied to the seed in a manner known per se, utilizing the combination and diluent of the present invention in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seed. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as a slow release capsule or microcapsule.

[0147] Usually, the formulations contain 0.01-90% by weight of active agent, 0-20% of agriculturally acceptable surfactants, and 10-99.99% of solid or liquid inert compounding agents and adjuvants, the active agent being at least the compound of formula (I) together with components (B) and (C) and, optionally, other active agents, in particular fungicides or preservatives. Concentrated forms of the composition generally contain about 2-80%, preferably about 5-70% by weight of active agent. Application forms of the formulations may contain, for example, 0.01-20% by weight, preferably 0.01-5% by weight of active agent. Commercial products will preferably be formulated as concentrates, but end users will usually utilize diluted formulations.

[0148] Table 1 below illustrates examples of individual compounds of formula (I) according to the invention.

[0149] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6]

[0150] Where: a)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0151] b)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0152] c)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0153] d) R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0154] e)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0155] f)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0156] g)R 2 , R 3 and R 5 is as defined in Table 1. [ka]

[0157] [Table 2]

[0158] Where: f)R 1 , R 2 , R 3 and R 5 36 compounds of formula (If), wherein: [ka]

[0159] g)R 1 , R 2 , R 3 and R 5 36 compounds of formula (Ig), wherein: [ka]

[0160] h)R 1 , R 2 , R 3 and R 536 compounds of formula (Ih), wherein: [ka]

[0161] j)R 1 , R 2 , R 3 and R 5 is as defined in Table 2. [ka]

[0162] k)R 1 , R 2 , R 3 and R 5 36 compounds of formula (Ik), wherein: [ka]

[0163] l)R 1 , R 2 , R 3 and R 5 36 compounds of formula (II), wherein: [ka]

[0164] g)R 1 , R 2 , R 3 and R 5 36 compounds of formula (Im), wherein: [ka]

[0165] Formulation example

[0166] [Table 3]

[0167] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder, which can be diluted with water to obtain a suspension of the desired concentration.

[0168] [Table 4]

[0169] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder which can be used directly for seed treatment.

[0170] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene Mixture 50%

[0171] Emulsions of any required dilution which can be used in plant protection can be obtained from this concentrate by dilution with water.

[0172] [Table 5]

[0173] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressing of seeds.

[0174] Extrusion Granules Active ingredient [compound of formula (I)] 15% Sodium Lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0175] The active ingredients are mixed and ground with the auxiliaries, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0176] Coated Granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (mol.wt.200) 3% Kaolin 89%

[0177] The finely ground active ingredient is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. Dust-free coated granules are thus obtained.

[0178] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium Lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0179] The finely ground active ingredient is thoroughly mixed with the adjuvants to obtain a suspension concentrate, from which suspensions of any desired dilution rate can be obtained by dilution with water, by which living plants as well as plant propagation material can be treated by spraying, pouring or immersion to protect them from microbial infestation.

[0180] Flowable concentrates for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol + 10-20 mole EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0181] The finely ground active ingredient is thoroughly mixed with the adjuvants to obtain a suspension concentrate, from which suspensions of any desired dilution rate can be obtained by dilution with water, by which living plants as well as plant propagation material can be treated by spraying, pouring or immersion to protect them from microbial infestation.

[0182] Slow-release capsule suspension 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-polyphenylisocyanate 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 achieved. To the emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete.

[0183] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% active ingredient. The median capsule diameter is 8-15 microns.

[0184] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for this purpose. EXAMPLES

[0185] The following examples are illustrative of the present invention.The compounds of the present invention can be distinguished from known compounds by their higher efficacy at low application rates, which can be verified by those skilled in the art by using the experimental procedures outlined in the examples and using lower application rates, such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm, if necessary.

[0186] The compounds of formula (I) may have many benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases caused by fungi or superior properties for use as pesticide active ingredients (e.g. high biological activity, advantageous spectrum of activity, high safety profile (including improved crop tolerance), improved physicochemical properties or high biodegradability).

[0187] List of Abbreviations °C = degrees Celsius, CDCl3 = chloroform-d, d = doublet, DIPEA = N,N-diisopropylethylamine, DMF = dimethylformamide, HATU = 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, m = multiplet, MHz = megahertz, PyBOP = benzotriazol-1-yl-oxytripyrrolidino-phosphonium hexafluorophosphate, q = quartet, s = singlet, THF = tetrahydrofuran

[0188] Example 1: This example illustrates the preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (compound P-11). a) Preparation of N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide [ka] To a solution of 3-hydroxy-4-methoxy-pyridine-2-carboxylic acid (1.1 equiv.) and 2,2-dimethylcyclobutylamine hydrochloride (1.5 g, 12.2 mmol, 1.0 equiv.) in dichloromethane (110 ml) were added sequentially PyBOP (1.1 equiv.) and DIPEA (3.3 equiv.). The reaction was stirred overnight at room temperature and then concentrated in vacuo. Direct purification of the crude product by chromatography on silica gel (eluent: cyclohexane / ethyl acetate mixtures) afforded the desired N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide in 92% yield (2.55 g, 10.2 mmol). 1 H-NMR (400MHz, CDCl3): δ=1.15(s,3H),1.21(s,3H),1.60-1.70(m,2H),1.93-1.98(m,1H),2.25-2.3 5(m,1H),3.96(s,3H),4.20-4.30(q,1H),6.87(d,1H),7.97(d,1H),8.10-8.20(m,1H),12.52(s,1H).

[0189] b) Preparation of 6-chloro-N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide [ka] N-Chlorosuccinimide (2.0 equiv.) was added portionwise to a stirred solution of N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide (2.55 g, 10.2 mmol, 1.0 equiv.) in DMF (51 ml). The reaction was stirred overnight at room temperature and then poured into sodium thiosulfate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. After purification by chromatography on silica gel (eluent: cyclohexane / ethyl acetate mixture), the desired 6-chloro-N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide (2.07 g, 7.27 mmol, 71% yield) was obtained. 1H-NMR (400MHz, CDCl3): δ=1.14(s,3H),1.22(s,3H),1.60-1.70(m,2H),1.95-2.05(m,1H),2.2 5-2.35(m,1H),3.97(s,3H),4.20-4.30(q,1H),6.86(s,1H),7.75-7.85(m,1H),12.60(s,1H).

[0190] c) Preparation of 6-chloro-N-(2,2-dimethylcyclobutyl)-3,4-dihydroxy-pyridine-2-carboxamide [ka] 6-Chloro-N-(2,2-dimethylcyclobutyl)-3-hydroxy-4-methoxy-pyridine-2-carboxamide (2.0 g, 7.02 mmol, 1.0 equiv.) and pyridine hydrochloride (7 equiv.) were stirred for 10 h at 150° C. The reaction was then cooled to room temperature and the crude mixture was directly purified by chromatography on silica gel (eluent: dichloromethane) to give the desired 6-chloro-N-(2,2-dimethylcyclobutyl)-3,4-dihydroxy-pyridine-2-carboxamide in 80% yield (1.52 g, 5.61 mmol). 1 H-NMR (400MHz, CDCl3): δ=1.15(s,3H),1.22(s,3H),1.60-1.70(m,2H),1.95-2.05(m,1 H),2.25-2.35(m,1H),4.20-4.30(q,1H),6.98(s,1H),7.70-7.85(m,1H),12.61(s,1H).

[0191] d) Preparation of 6-chloro-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide [ka] Under argon atmosphere, to a solution of 6-chloro-N-(2,2-dimethylcyclobutyl)-3,4-dihydroxy-pyridine-2-carboxamide (700 mg, 2.59 mmol, 1.0 equiv.) in DMF (10.3 ml) were added successively cesium carbonate (2.0 equiv.) and dibromomethane (1.2 equiv.). The mixture was stirred at 110° C. for 1 h, then cooled to room temperature, quenched with water, and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate mixture) to give the desired 6-chloro-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide in 78% yield (572 mg, 2.02 mmol). 1 H-NMR (400MHz, CDCl3): δ=1.11(s,3H),1.22(s,3H),1.60-1.70(m,2H),1.90-1.97( m,1H),2.25-2.35(m,1H),4.25-4.30(q,1H),6.25(s,2H),6.89(s,1H),7.61(m,1H).

[0192] e) Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (compound P-11) [ka] Under an argon atmosphere, BrettPhos-G3-palladacycle ([(2-di-cyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate methanesulfonate, 0.1 equiv.) and potassium tert-butoxide (2.5 equiv.) were added to a degassed, stirred mixture of 6-chloro-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (100 mg, 0.354 mmol, 1 equiv.) and 3,5-difluoroaniline (1.1 equiv.) in THF (1.5 ml). The reaction was heated to 80° C. and stirred for 1 h, then the mixture was cooled to room temperature. The volatiles were removed using a rotary evaporator and the residue was dissolved in ethyl acetate. The organic phase was washed twice with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by column chromatography on silica gel (eluent: cyclohexane ethyl acetate) afforded the desired methyl 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide (76 mg, 57% yield). 1 H-NMR (400MHz, CDCl3): δ=1.13(s,3H),1.21(s,3H),1.60-1.70(m,2H),1.80-1.95(m,1H),2.25-2. 35(m,1H),4.40-4.45(q,1H),6.17(s,2H),6.40-6.55(m,3H),6.90-7.05(m,2H),7.60-7.65(m,1H).

[0193] Throughout this specification temperatures are in degrees Celsius (° C.) and "mp" means melting point. LC / MS means liquid chromatography mass spectrometry, with a description of the apparatus and methods as follows. (Method A: Waters ACQUITY UPLC, Waters UPLC HSS T3, 1.8 μm particle size, 30×2.1 mm column, 0.85 mL / min, 60° C., HO / MeOH 95:5+0.05% HCOOH(90%) / CHCN+0.05% HCOOH(10%)-1.2 min-CHCN+0.05% HCOOH(100%)-0.30 min, Waters ACQUITY SQD mass spectrometer, ionization method: electrospray (ESI), polarity: positive ion, capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (° C.) 150, stripping temperature (° C.) 350, cone gas flow (L / Hr) 0, stripping gas flow (L / Hr) 650). Method B: Waters ACQUITY UPLC, Waters UPLC HSS T3, 1.8 μm particle size, 30×2.1 mm column, 0.85 mL / min, 60° C., HO / MeOH 95:5+0.05% HCOOH(90%) / CHCN+0.05% HCOOH(10%)-2.7 min-CHCN+0.05% HCOOH(100%)-0.30 min, Waters ACQUITY SQD mass spectrometer, ionization method: electrospray (ESI), polarity: positive ion, capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (° C.) 150, stripping temperature (° C.) 350, cone gas flow (L / Hr) 0, stripping gas flow (L / Hr) 650). Method C: Waters Corporation's ACQUITY Mass Spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150° C., desolvation temperature: 400° C., cone gas flow: 60 L / h, desolvation gas flow: 700 L / hr, mass range: 140-800 Da) and a Waters Corporation's ACQUITY UPLC with a solvent degasser, binary pump, heated column compartment and dipole array detector.Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 2.5 min; Flow rate (mL / min): 0.75.

[0194] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] [Table 6-5] [Table 6-6] [Table 6-7]

[0195] Biological Examples Example B1. Alternaria solani / Tomato / Leaf disc (summer blight) Tomato leaf discs (cv. Baby) are placed on agar in a multi-well plate (24-well type) and sprayed with the formulated test compounds diluted in water. Two days after application, the discs are inoculated with a fungal spore suspension. The inoculated discs are incubated in a climate cabinet at 23°C / 21°C (day / night) and 80% rh under a 12 / 12 h (light / dark) light regime, and the activity of the compounds is evaluated as the percentage of disease control compared to untreated test discs when an appropriate level of disease appears on the untreated test discs (5-7 days after application). The following compounds provided at least 80% control of Alternaria solani at 200 ppm compared to untreated controls exhibiting significant disease development under identical conditions: P-8, P-9, P-18, P-19, P-21, P-22, P-23, P-24, and P-25.

[0196] Example B2. Botryotinia fuckeliana (Botrytis cinerea) / Liquid culture (grey mold) Fungal conidia stored at cryogenic temperatures are mixed directly into nutrient liquid medium (Vogels liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of nutrient liquid medium containing fungal spores. The test plates are incubated at 24°C and growth inhibition is measured photometrically 3-4 days after application. The following compounds provided at least 80% control of Botryotinia fuckeliana at 20 ppm compared to untreated controls showing significant disease development under identical conditions: P22.

[0197] Example B3. Glomerella lagenarium (Colletotrichum lagenarium) / Liquid Culture (Anthracnose) Fungal conidia stored at cryogenic temperatures are mixed directly into nutrient liquid medium (PDB potato dextrose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of nutrient liquid medium containing fungal spores. The test plates are incubated at 24°C and growth inhibition is measured photometrically 3-4 days after application. The following compounds provided at least 80% control of Glomerella lagenarium at 20 ppm compared to untreated controls showing significant disease development under identical conditions: P-1, P-2, P-3, P-5, P-6, P-7, P-8, P-9, P-10, P-11, P-14, P-15, P-18, P-19, P-20, P-21, P-22, P-23, P-24, P-25, and P-26.

[0198] Example B4. Blumeria graminis f.sp. tritici (Erysiphe graminis f.sp. tritici) / Wheat / Leaf-plate prevention (powdery mildew in wheat) Wheat leaf discs (cv. Kanzler) are placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the leaves are inoculated with powdery mildew-infected plants by shaking them on the test plate. The inoculated leaf discs are incubated in a climate chamber at 20°C and 60% rh under a light regime of 24 hours dark followed by 12 hours light / 12 hours dark, and the activity of the compounds is evaluated as the percentage of disease control compared to untreated when an appropriate level of disease appears on the untreated test leaves (6-8 days after application). The following compounds provided at least 80% control of Blumeria graminis f.sp. tritici at 200 ppm compared to untreated controls showing significant disease development under identical conditions: P-9, P-11, P-14, P-18, and P-22.

[0199] Example B5. Phaeosphaeria nodorum (Septoria nodorum) / Wheat / Leaf septorium preventive (Septoria nodorum) Wheat leaf pieces (cv. Kanzler) are placed on agar in a multi-well plate (24-well type) and sprayed with the formulated test compounds diluted in water. The leaves are inoculated with a fungal spore suspension 2 days after application. The inoculated test leaves are incubated in a climate cabinet at 20°C and 75% rh under a 12-hour light / 12-hour dark light regime, and the activity of the compounds is evaluated as the percentage of disease control compared to the untreated when a suitable level of disease appears on the untreated test leaves (5-7 days after application). The following compounds provided at least 80% control of Phaeosphaeria nodorum at 200 ppm compared to untreated controls showing significant disease development under the same conditions: P-5, P-11, P-15, P-18, P-22, and P-25.

[0200] Example B6. Monographella nivalis (Microdochium nivale) / Liquid culture (Root rot of cereals) Fungal conidia stored at cryogenic temperatures are mixed directly into nutrient liquid medium (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of nutrient liquid medium containing fungal spores. The test plates are incubated at 24°C and growth inhibition is measured photometrically 4-5 days after application. The following compounds provided at least 80% control of Monographella nivalis at 20 ppm compared to untreated controls showing significant disease development under identical conditions: P-5, P-6, P-7, P-8, P-9, P-10, P-11, P-12, P-14, P-15, P-17, P-18, P-19, P-20, P-21, P-22, P-23, P-24, P-25, and P-26.

[0201] Example B7. Mycosphaerella arachidis (Cercospora arachidicola) / Liquid Culture (Early Spot Disease) Fungal conidia stored at cryogenic temperatures are mixed directly into nutrient liquid medium (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of nutrient liquid medium containing fungal spores. The test plates are incubated at 24°C and growth inhibition is measured photometrically 4-5 days after application. The following compounds provided at least 80% control of Mycosphaerella arachidis at 20 ppm compared to untreated controls showing significant disease development under identical conditions: P-8, P-9, P-11, P-15, P-18, P-19, P-21, P-22, and P-25.

[0202] Example B8. Puccinia recondita f.sp. tritici / wheat / leaf disc preventative (leaf rust) Wheat leaf pieces (cv. Kanzler) are placed on agar in a multi-well plate (24-well type) and sprayed with the formulated test compound diluted in water. One day after application, the leaf pieces are inoculated with a fungal spore suspension. The inoculated test leaf pieces are incubated in a climate cabinet under a 12-h light / 12-h dark light regime at 19°C and 75% rh, and the activity of the compound is evaluated as the percentage of disease control compared to the untreated when a suitable level of disease appears on the untreated test leaf pieces (7-9 days after application). The following compounds provided at least 80% control of Puccinia recondita f.sp. tritici at 200 ppm compared to untreated controls showing significant disease development under identical conditions: P-8, P-11, P-12, P-18, P-21, P-22, P-25, and P-26.

[0203] Example B9. Magnaporthe grisea (Pyricularia oryzae) / Rice / Leaf Scab Preventative (Rice Blast) Rice leaf segments (cv. Ballila) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf segments are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf segments are incubated in a climate chamber at 22°C and 80% rh under a light regime of 24 hours darkness followed by 12 hours light / 12 hours darkness and the activity of the compounds is evaluated as the percentage disease control compared to untreated when an appropriate level of disease appears on the untreated test leaf segments (5-7 days after application). The following compounds provided at least 80% control of Magnaporthe grisea at 200 ppm compared to untreated controls showing significant disease development under identical conditions: P-5, P-14, P-15, P-17, P-18, P-19, P-21, P-22, P-24, P-25, and P-26.

[0204] Example B10. Pyrenophora teres / Barley / Leaf patch preventative (net blotch) Barley leaf segments (cv. Hasso) are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf segments are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf segments are incubated in a climate chamber at 20°C and 65% rh under a 12-hour light / 12-hour dark photoperiod and the activity of the compounds is evaluated as disease control compared to untreated when an appropriate level of disease appears on the untreated test leaf segments (5-7 days after application). The following compounds provided at least 80% control of Pyrenophora teres at 200 ppm compared to untreated controls exhibiting significant disease development under identical conditions: P-5, P-8, P-9, P-15, P-18, P-19, P-21, P-22, P-23, P-25, and P-26.

[0205] Example B11. Wheat leaf spot fungus (Mycosphaerella graminicola) (Septoria tritici) / Liquid culture (leaf spot) Fungal conidia stored at cryogenic temperatures are mixed directly into nutrient liquid medium (PDB potato dextrose liquid medium). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) and then the nutrient liquid medium containing the fungal spores is added. The test plate is incubated at 24°C and growth inhibition is measured photometrically 4-5 days after application. The following compounds provided at least 80% control of Mycosphaerella graminicola at 20 ppm compared to untreated controls exhibiting significant disease development under identical conditions: P-2, P-5, P-7, P-8, P-9, P-10, P-11, P-12, P-13, P-14, P-15, P-17, P-18, P-19, P-20, P-21, P-22, P-23, P-24, P-25, and P-26.

Claims

1. Compounds of formula (I): 【Chemistry 1】 (In the formula, R 1 is hydrogen, cyano, or C 1 -C alkylcarbonyl; R 2 and R 3 are each independently hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, halogen, or C 1 ~C 6 Alkoxy C 1 ~C 2 is alkyl; R 4 is C 1 ~C 8 Alkyl, C 1 ~C 8 Haloalkyl, C 1 ~C 8 Alkoxy, C 3 ~C 8 Cycloalkyl, C 3 ~C 8 Cycloalkyl C 1 ~C 2 alkyl (wherein the cycloalkyl group is R 6 (optionally substituted with 1 to 3 groups represented by 1 ~C 3 Alkyl, Heteroaryl, Heteroaryl C 1 ~C 3 alkyl, wherein said heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3, or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur; heterocyclyl, heterocyclylC 1 ~C 3 Alkyl, wherein the heterocyclyl is selected from the group consisting of nitrogen, oxygen, sulfur, and S(O) 2 and wherein the heterocyclyl group is a 4-, 5-, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms or groups individually selected from R 7 or optionally containing 1, 2, 3, 4 or 5 heteroatoms individually selected from nitrogen, oxygen and sulfur, and C 1 ~C 2 a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system optionally attached to the remainder of the molecule via an alkylene linker; R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein said phenyl or heteroaryl group is selected from R 6 optionally substituted with 1, 2 or 3 substituents, which may be the same or different, selected from R 6 is halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or C 1 ~C 4 haloalkyl; R 7 is halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy or C 1 ~C 4 haloalkoxy); or a salt or N-oxide thereof.

2. R 1 The compound of claim 1 , wherein is hydrogen, cyano or acetyl.

3. R 2 and R 3 are each independently hydrogen, C 1 ~C 3 3. The compound of claim 1 or claim 2, wherein the aryl group is alkyl or halogen.

4. R 2 and R 3 The compound according to any one of claims 1 to 3, wherein each is independently hydrogen, methyl, or fluoro.

5. R 4 is C 1 ~C 8 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 8 Alkoxy, C 3 ~C 6 Cycloalkyl, C 3 ~C 4 Cycloalkyl C 1 ~C 2 alkyl (wherein the cycloalkyl group is R 6 (Optionally substituted with 1 or 2 groups represented by 1 ~C 3 Alkyl, heterocyclyl, heterocyclyl C 1 ~C 3 Alkyl, wherein the heterocyclyl is selected from oxygen, sulfur, and S(O) 2 5. The compound according to claim 1, wherein the heterocyclyl group is optionally substituted with only one group represented by R7), or a 6- to 9-membered non-aromatic spirocyclic carbobi-cyclyl ring system optionally containing 1 or 2 heteroatoms individually selected from nitrogen, oxygen and sulfur.

6. R 4 is C 3 ~C 8 Alkyl, C 3 ~C 6 Cycloalkyl (wherein the cycloalkyl group is R 6 (Optionally substituted with 1 or 2 groups represented by 1 ~C 3 Alkyl, Heterocyclyl C 1 ~C 3 Alkyl, wherein the heterocyclyl is selected from oxygen, sulfur, and S(O) 2 wherein said heterocyclyl group is optionally substituted with only one group represented by R7), or phenyl C 1 ~C 3 The compound according to any one of claims 1 to 5, which is alkyl.

7. R 5 is phenyl or heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from nitrogen and sulfur, and wherein said phenyl or heteroaryl group is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R.

8. R 5 is phenyl or pyridyl, wherein each phenyl or pyridyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R.

9. R 6 The compound according to any one of claims 1 to 8, wherein is methyl.

10. R 7 The compound according to any one of claims 1 to 9, wherein is chloro, fluoro, methyl, or methoxy.

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

12. 12. The composition of claim 11 further comprising at least one additional active ingredient and / or an agronomically acceptable diluent or carrier.

13. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, which comprises applying a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 10, or a composition as defined in claim 11 or claim 12, to said plant, its part or its habitat.

14. Use of a compound of formula (I) according to any one of claims 1 to 10 as a fungicide.

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