Microbicidal derivatives

Abstract

Disclosed is a compound having the formula (I) wherein the substituents are as defined in claim 1, and the compound can be used as a pesticidal agent and especially as a fungicide.

Description

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

[0002] WO 2010 / 012793 and WO 2017 / 207362 describe thiazole derivatives as pest control agents.

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

[0004]

[0005] wherein

[0006] A is C-H or N;

[0007] R 1 is C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkylsulfanyl C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur;

[0008] R 2 is hydrogen or halogen;

[0009] R 3 is C1-C8 alkyl;

[0010] R 4 、R 5 、R 6 are each independently hydrogen or C1-C4 alkyl;

[0011] R 7 is hydrogen, C1-C4 alkyl, C1-C6 alkoxycarbonyl C1-C4 alkyl, C1-C6 alkoxycarbonyl, or C1-C6 alkoxy;

[0012] R 8is hydrogen, C1-C6 alkoxy C1-C6 alkylcarbonyl, C1-C6 alkylthio C1-C6 alkylcarbonyl, C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl, C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl, or heterocyclic carbonyl, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur;

[0013] or a salt or N-oxide thereof.

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

[0015] According to a third aspect of the present invention, there is provided a method of controlling or preventing useful plants from being infested by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) or a composition comprising such a compound as an active ingredient is applied to the plants, parts thereof or the places where they are located.

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

[0017] As used herein, the term "halogen" means fluorine, chlorine, bromine or iodine.

[0018] As used herein, the term "C1-C8 alkyl" means a straight-chain or branched-chain hydrocarbon chain group consisting only of carbon and hydrogen atoms, said hydrocarbon chain group being unsaturation-free, having from one to eight carbon atoms and being attached to the remainder of the molecule by a single bond. "C1-C6 alkyl", "C1-C4 alkyl" and "C1-C3 alkyl" should be interpreted accordingly. Examples of C1-C8 alkyl include, but are not limited to, methyl, ethyl, n-propyl and its isomers, such as isopropyl. The "C1-C6 alkylene" group has the corresponding definition of C1-C6 alkyl, except that such a group is attached to the remainder of the molecule by two single bonds.

[0019] As used herein, the term "C1-C6 alkoxy" means a group of the formula -OR a wherein R ais a C1-C6 alkyl group as commonly defined above. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" shall be interpreted accordingly. Examples of C1-C6 alkoxy groups include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

[0020] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" refers to a group having the formula R b OR a -, where R b is a C1-C6 alkyl group as commonly defined above, and R a is a C1-C6 alkylene group as commonly defined above. "C1-C6 alkoxy C1-C6 alkyl", "C1-C4 alkoxy C1-C4 alkyl", "C1-C4 alkoxy C1-C3 alkyl", "C1-C4 alkoxy C1-C2 alkyl", and "C3-C4 alkoxy C1-C2 alkyl" shall be interpreted accordingly. Examples of C1-C6 alkoxy C1-C6 alkyl groups include, but are not limited to, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl.

[0021] As used herein, the term "C1-C6 alkoxycarbonyl" refers to a group having the formula R a OC(O)-, where R a is a C1-C6 alkyl group as commonly defined above. "C1-C4 alkoxycarbonyl" and "C1-C3 alkoxycarbonyl" shall be interpreted accordingly.

[0022] As used herein, the term "C1-C6 alkoxycarbonyl C1-C4 alkyl" refers to a group having the formula R a OC(O)R b -, where R a is a C1-C6 alkyl group as commonly defined above, and R b is a C1-C4 alkylene group as commonly defined above.

[0023] As used herein, the term "C1-C6 alkoxy C1-C6 alkylcarbonyl" refers to a group having the formula R a OR b C(O)-, where R a is a C1-C6 alkyl group as commonly defined above, and R b is a C1-C6 alkylene group as commonly defined above.

[0024] As used herein, the term "C1-C6 alkylthio C1-C6 alkyl" refers to a group having the formula R a SR b -, where R ais a C1-C6 alkyl group as defined above generally, and R b is a C1-C6 alkylene group as defined above generally.

[0025] As used herein, the term "C1-C6 alkylsulfinyl C1-C6 alkyl" refers to a group having the formula R a S(O)R b -, where R a is a C1-C6 alkyl group as defined above generally, and R b is a C1-C6 alkylene group as defined above generally.

[0026] As used herein, the term "C1-C6 alkylthio C1-C6 alkylcarbonyl" refers to a group having the formula R a SR b C(O)-, where R a is a C1-C6 alkyl group as defined above generally, and R b is a C1-C6 alkylene group as defined above generally.

[0027] As used herein, the term "C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl" refers to a group having the formula R a S(O)R b C(O)-, where R a is a C1-C6 alkyl group as defined above generally, and R b is a C1-C6 alkylene group as defined above generally.

[0028] As used herein, the term "C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl" refers to a group having the formula R a S(O)2R b C(O)-, where R a is a C1-C6 alkyl group as defined above generally, and R b is a C1-C6 alkylene group as defined above generally.

[0029] As used herein, the term "heterocyclic group" refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms, where the heteroatoms are independently selected from nitrogen, oxygen and sulfur. The heterocyclic group can be bonded to the remainder of the molecule through a carbon atom or a heteroatom. Examples of heterocyclic groups include, but are not limited to, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl.

[0030] As used herein, the term "heterocyclic group carbonyl" refers to a group having the formula R aa group of C(O)-, wherein R a is a heterocyclic radical moiety as defined above.

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

[0032] In each case, the compounds of formula (I) according to the present invention are in the free form, the oxidized form (such as N-oxide), or the salt form (such as an agriculturally useful salt form).

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

[0034] The following list provides definitions, including preferred definitions, for the substituents A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 of the compounds of formula (I). For any one of these substituents, any of the definitions given below can be combined with any of the definitions of any other substituents given below or elsewhere in this document.

[0035] A is C-H or N. In one group of embodiments, A is C-H. In another group of embodiments, A is N.

[0036] R 1 is C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or a heterocyclic radical, wherein the heterocyclic radical moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0037] Preferably, R 1 is C1-C4 alkoxy C1-C2 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0038] More preferably, R 1 is C1-C3 alkoxy C1-C2 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0039] Even more preferably, R 1 is C3-C4 alkoxy C1-C2 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0040] Even still more preferably, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0041] In another preferred embodiment, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

[0042] In one embodiment, R 1 is C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0043] Preferably, R 1 is C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, C1-C4 alkylsulfinyl C1-C4 alkyl, C1-C4 alkylsulfonyl C1-C4 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0044] More preferably, R 1 is C1-C4 alkoxy C1-C3 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0045] Even more preferably, R 1 is C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0046] Still even more preferably, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylthioethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0047] Most preferably, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0048] In one group of embodiments, R 1 is C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0049] In another group of embodiments, R 1is C1-C4 alkylthio C1-C4 alkyl, C1-C4 alkylsulfinyl C1-C4 alkyl, C1-C4 alkylsulfonyl C1-C4 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0050] In another group of embodiments, R 1 is C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0051] In another group of embodiments, R 1 is C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0052] In still another group of embodiments, R 1 is C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0053] In a preferred group of embodiments, R 1 is 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

[0054] In a more preferred group of embodiments, R 1 is 1-methylthioethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0055] In a most preferred group of embodiments, R 1 is 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0056] In another group of preferred embodiments, R 1is a C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0057] Preferably, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylthioethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl. More preferably, R 1 is isopropoxymethyl, tert-butoxymethyl, 1-isopropoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0058] R 2 is hydrogen or halogen. Preferably, R 2 is hydrogen, chlorine, bromine, or fluorine. More preferably, R 2 is hydrogen or fluorine. In one set of embodiments, R 2 is hydrogen. In another set of embodiments, R 2 is fluorine.

[0059] R 3 is a C1-C8 alkyl. Preferably, R 3 is a C1-C6 alkyl. More preferably, R 3 is a C1-C3 alkyl. Even more preferably, R 3 is methyl, ethyl, or isopropyl. Most preferably, R 3 is methyl.

[0060] R 4 、R 5 、R 6 are each independently hydrogen or a C1-C4 alkyl. Preferably, R 4 、R 5 、R 6 are each independently hydrogen or a C1-C3 alkyl. More preferably, R 4 、R 5 、R 6 are each independently hydrogen or methyl.

[0061] In one set of embodiments, R 4 is hydrogen, and R 5 and R 6 are both methyl.

[0062] R 7is hydrogen, a C1-C4 alkyl group, a C1-C6 alkoxycarbonyl C1-C4 alkyl group, a C1-C6 alkoxycarbonyl group, or a C1-C6 alkoxy group. Preferably, R 7 is hydrogen, a C1-C3 alkyl group, a C1-C4 alkoxycarbonyl C1-C3 alkyl group, a C1-C4 alkoxycarbonyl group, or a C1-C4 alkoxy group. More preferably, R 7 is hydrogen, a C1-C3 alkyl group, a C1-C3 alkoxycarbonyl C1-C2 alkyl group, a C1-C3 alkoxycarbonyl group, or a C1-C3 alkoxy group. Even more preferably, R 7 is hydrogen, methyl, methoxycarbonylmethyl, methoxycarbonyl, or methoxy. Still more preferably, R 7 is hydrogen or methyl. Most preferably, R 7 is hydrogen.

[0063] R 8 is hydrogen, a C1-C6 alkoxy C1-C6 alkylcarbonyl group, a C1-C6 alkylthio C1-C6 alkylcarbonyl group, a C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl group, a C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl group, or a heterocyclic carbonyl group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0064] Preferably, R 8 is hydrogen, a C1-C4 alkoxy C1-C4 alkylcarbonyl group, a C1-C4 alkylthio C1-C4 alkylcarbonyl group, a C1-C4 alkylsulfinyl C1-C4 alkylcarbonyl group, a C1-C4 alkylsulfonyl C1-C4 alkylcarbonyl group, or a heterocyclic carbonyl group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen, oxygen and sulfur.

[0065] More preferably, R 8 is hydrogen, a C1-C3 alkoxy C1-C3 alkylcarbonyl group, a C1-C3 alkylthio C1-C3 alkylcarbonyl group, a C1-C3 alkylsulfinyl C1-C3 alkylcarbonyl group, a C1-C3 alkylsulfonyl C1-C3 alkylcarbonyl group, or a heterocyclic carbonyl group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen.

[0066] Even more preferably, R 8 is hydrogen, or a heterocyclic carbonyl group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0067] Even still more preferably, R 8 is hydrogen or tetrahydrofuran-3-carbonyl. Most preferably, R 8 is hydrogen.

[0068] In the compounds of formula (I) according to the present invention, preferably:

[0069] A is C-H or N;

[0070] R 1 is C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom;

[0071] R 2 is hydrogen or fluorine;

[0072] R 3 is methyl;

[0073] R 4 、R 5 、and R 6 are each independently hydrogen or methyl;

[0074] R 7 is hydrogen; and

[0075] R 8 is hydrogen or a heterocyclic carbonyl group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0076] More preferably, A is N;

[0077] R 1 is C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom;

[0078] R 2 is hydrogen or fluorine;

[0079] R 3 is methyl;

[0080] R 4 、R 5 、and R 6 are each independently hydrogen or methyl;

[0081] R 7 is hydrogen; and

[0082] R 8 is hydrogen or tetrahydrofuranyl.

[0083] Even more preferably, A is N;

[0084] R 1 is a C1-C3 alkylthio C1-C3 alkyl, a C1-C3 alkylsulfinyl C1-C3 alkyl, a C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4- or 5-membered non-aromatic monocyclic ring containing a single oxygen atom;

[0085] R 2 is hydrogen or fluorine;

[0086] R 3 is methyl;

[0087] R 4 is hydrogen;

[0088] R 5 and R 6 are both methyl;

[0089] R 7 is hydrogen; and

[0090] R 8 is hydrogen.

[0091] In another set of preferred embodiments, in the compounds of formula (I) according to the present invention, preferably, A is N;

[0092] R 1 is a C1-C4 alkoxy C1-C2 alkyl, a C1-C6 alkylthio C1-C6 alkyl, a C1-C6 alkylsulfinyl C1-C6 alkyl, a C1-C6 alkylsulfonyl C1-C6 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur;

[0093] R 2 is hydrogen or fluorine;

[0094] R 3 is methyl;

[0095] R 4 is hydrogen;

[0096] R 5 and R 6 are both methyl;

[0097] R 7 is hydrogen; and

[0098] R 8 is hydrogen.

[0099] More preferably, A is N;

[0100] R 1is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, C1-C3 alkylthio C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or a heterocyclic group, wherein the heterocyclic moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from nitrogen and oxygen;

[0101] R 2 is hydrogen or fluorine;

[0102] R 3 is methyl;

[0103] R 4 is hydrogen;

[0104] R 5 and R 6 are both methyl;

[0105] R 7 is hydrogen; and

[0106] R 8 is hydrogen.

[0107] Preferably, the compound having the formula (I) is selected from:

[0108] 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (P-1);

[0109] 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-2-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-2);

[0110] 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-3);

[0111] 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-4);

[0112] 2-[2-tert-butoxypropionyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-5);

[0113] 2-[(2,6-Difluoro-4-pyridinyl)-(2-isopropoxypropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-6);

[0114] 2-[(2-tert-Butoxyacetyl)-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-7);

[0115] 2-[(2,6-Difluoro-4-pyridinyl)-(2-isopropoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-8);

[0116] 2-[(2,6-Difluoro-4-pyridinyl)-(2-methoxypropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-9);

[0117] 2-[(2,6-Difluoro-4-pyridinyl)-(2-methylsulfonylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-10); and

[0118] 2-[(2,6-Difluoro-4-pyridinyl)-(tetrahydrofuran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-11).

[0119] The compounds of the present invention can be prepared as shown in the following scheme, wherein, unless otherwise stated, the definition of each variable is as defined above for the compounds having formula (I).

[0120] The compound of formula (Ia) according to the present invention (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined for formula (I) and R 8 is hydrogen) can be obtained by: by heating thermally or with the aid of a base, a compound of formula (II) (wherein A, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as defined for formula (I)) with a compound of formula (III) (wherein R 1is as defined for formula (I), and Xa is a halogen, preferably bromine or chlorine) is converted. This is shown in Scheme 1 below.

[0121] Scheme 1

[0122]

[0123] Those skilled in the art will recognize that the conditions for preparing the compounds of formula (Ia) will depend on the stoichiometry of the reaction. For example, reacting 1 - 1.5 equivalents of the compound of formula (III) with 1 equivalent of the compound of formula (II) will predominantly produce the compound of formula (Ia), while reacting 2 - 2.1 equivalents of the compound of formula (III) with 1 equivalent of the compound of formula (II) will produce the compound of formula (Ib), where R 8a is C1 - C6 alkoxy C1 - C6 alkylcarbonyl, C1 - C6 alkylthio C1 - C6 alkylcarbonyl, C1 - C6 alkylsulfinyl C1 - C6 alkylcarbonyl, C1 - C6 alkylsulfonyl C1 - C6 alkylcarbonyl, or heterocyclic carbonyl, where the heterocyclic group is a 4 - membered, 5 - membered or 6 - membered non - aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from nitrogen, oxygen and sulfur. This is shown in Scheme 2 below.

[0124] Scheme 2

[0125]

[0126] The compound of formula (II) (where A, R 2 、R 3 、R 4 、R 5 、R 6 、and R 7 are as defined for formula (I)) can be obtained by thermally heating or by means of a base or under transition - metal - catalyzed Buchwald - Hartwig amination conditions, reacting the compound of formula (IV) (where A and R 2 are as defined for formula (I)) with the compound of formula (V) (where R 3 、R 4 、R 5 、R 6 、and R 7 are as defined for formula (I) and Xb is a halogen, preferably bromine or chlorine) is converted. This is shown in Scheme 3 below. Such compounds of formula (II) have been described in WO 2019 / 105933.

[0127] Scheme 3

[0128]

[0129] A compound having formula (V) wherein R 3 , R 4 , R 5 , R 6 , and R 7 are as defined for formula (I) and Xb is a halogen, preferably bromine or chlorine) can be obtained by converting a compound having formula (VI) wherein R 2 is as defined for formula (I) and Xb is a halogen, preferably bromine) and a compound having formula (VII) wherein R 4 , R 5 , R 6 , and R 7 are as defined for formula (I) either via an intermediate acid chloride or directly with a peptide coupling agent. This is shown in Scheme 4 below.

[0130] Scheme 4

[0131]

[0132] A compound having formula (VI) wherein R 3 is as defined for formula (I) and Xb is a halogen, preferably bromine or chlorine) can be obtained by converting a compound having formula (VIII) wherein R 3 is as defined for formula (I), Xb is a halogen, preferably bromine or chlorine, and R 9 is a C1-C6 alkyl) and a base. This is shown in Scheme 5 below.

[0133] Scheme 5

[0134]

[0135] Alternatively, a compound having formula (II) wherein R 2 and A are as defined for formula (I) can be obtained by converting a compound having formula (IX) wherein R 2 , R 3 and A are as defined for formula (I) with a compound having formula (VII) wherein R 4 , R 5 , R 6 , and R 7 are as defined for formula (I) either via an intermediate acid chloride or directly with a peptide coupling agent. This is shown in Scheme 6 below.

[0136] Scheme 6

[0137]

[0138] A compound of formula (IX) in which R 2 , A and R 3 are as defined for formula (I) can be obtained by converting a compound of formula (X) in which R 2 , R 3 and A are as defined for formula (I) and R 10 is C1-C6 alkyl with a base. This is shown in Scheme 7 below.

[0139] Scheme 7

[0140]

[0141] A compound of formula (X) in which R 2 , A, and R 3 are as defined for formula (I) and R 10 is C1-C6 alkyl can be obtained by thermally heating or by means of a base or under transition metal-catalyzed Buchwald-Hartwig amination conditions, converting a compound of formula (IV) in which A and R 2 are as defined for formula (I) with a compound of formula (VII) in which R 3 is as defined for formula (I), Xb is a halogen, preferably bromine or chlorine, and R 10 is C1-C6 alkyl. This is shown in Scheme 8 below.

[0142] Scheme 8

[0143]

[0144] Alternatively, a compound of formula (X) in which R 2 , A and R 3 are as defined for formula (I) and R 10 is C1-C6 alkyl can be obtained by under transition metal-catalyzed Buchwald-Hartwig amination conditions, converting a compound of formula (XI) in which R 2 and A are as defined for formula (I) and Xc is a halogen, preferably bromine or iodine, with a compound of formula (XII) in which R 3 is as defined for formula (I) and R 10 is C1-C6 alkyl. This is shown in Scheme 9 below.

[0145] Scheme 9

[0146]

[0147] Alternatively, a compound of formula (II) in which A, R 2 、R 3 、R 4 、R 5 、R 6 、and R 7 are as defined for formula (I) can be obtained by thermally heating or by means of a base or under transition metal-catalyzed Buchwald-Hartwig amination conditions, a compound of formula (XI) in which A and R 2 are as defined for formula (I) and Xc is a halogen, preferably bromine or iodine) with a compound of formula (XIII) in which R 3 、R 4 、R 5 、R 6 、and R 7 are as defined for formula (I). This is shown in Scheme 10 below.

[0148] Scheme 10

[0149]

[0150] Surprisingly, for practical purposes, novel compounds of formula (I) have now been found to have a very favorable level of biological activity for protecting plants against diseases caused by fungi.

[0151] Compounds of formula (I) can be used, for example, as active ingredients in the agricultural sector and related fields to control phytopathogenic pests or on inanimate materials to control spoilage microorganisms or organisms potentially harmful to humans. These novel compounds are characterized by excellent activity at low application rates, good plant tolerance and environmental safety. They have very useful therapeutic, prophylactic and systemic properties and can be used to protect many cultivated plants. Compounds of formula (I) can be used to inhibit or destroy pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of a variety of different useful plant crops while also protecting, for example, those later-growing plant parts from attack by phytopathogenic microorganisms.

[0152] The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation materials and / or harvested food crops which are susceptible to microbial attack, wherein an effective amount of a compound of formula (I) is applied to the plants, parts thereof or their locus.

[0153] It is also possible to use the compounds of formula (I) as fungicides. As used herein, the term "fungicide" means a compound which controls, modifies or prevents fungal growth. The term "fungicidally effective amount" means an amount of such a compound or combination of such compounds which is capable of having an effect on fungal growth. The effects of control or modification include all deviations from natural development, such as killing, retardation, etc., and prevention includes barriers or other defense structures which prevent fungal infection within or on the plant.

[0154] It is also possible to use the compounds of formula (I) as dressing agents for treating plant propagation materials, such as seeds (e.g. fruits, tubers or grains) or plant cuttings (e.g. rice), for protecting against fungal infestation as well as against phytopathogenic fungi present in the soil. The propagation materials can be treated with a composition comprising a compound of formula (I) before planting: for example, the seeds can be dressed before sowing.

[0155] The active ingredient according to the invention can also be applied to the grains (coating) by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when planting the propagation material, for example to the furrow of the seeds during sowing. The present invention also relates to such methods of treating plant propagation materials and to plant propagation materials so treated.

[0156] In addition, the compounds according to the invention can be used for controlling fungi in related fields, such as, for example, in the protection of industrial materials (including wood and wood-related industrial products), in food storage, in hygiene management.

[0157] In addition, the present invention can also be used for protecting inanimate materials (such as wood, wall panels and coatings) from fungal attack.

[0158] For example, the compounds of formula (I) may be effective against fungal and fungal vectors of diseases as well as phytopathogenic bacteria and viruses. These fungal and fungal vectors of diseases as well as phytopathogenic bacteria and viruses are, for example:

[0159] Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terreus), Aureobasidium spp (including A. pullulans), Blastomyces dermatitidis, Blumeria 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, Cercosporaspp (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, Epidermophyton spp, Erwinia amylovora, Erysiphe spp (including E. cichoracearum), Eutypa lata, Fusarium spp (including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, plants infected with Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp (including H. capsulatum), Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp (including M.graminicola), apple black spot pathogen (M. pomi)), tree tip blight pathogen (Oncobasidium theobromaeon), spruce pathogen (Ophiostoma piceae), Paracoccidioides spp, Penicillium spp (including Penicillium digitatum, Penicillium italicum), Petriellidium spp, Peronosclerospora spp (including Peronosclerospora maydis, Peronosclerospora philippinensis, and Peronosclerospora sorghi), Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp (including Phytophthora infestans), Plasmopara spp (including Plasmopara halstedii, Plasmopara viticola), Pleospora spp, Podosphaera spp (including Podosphaera leucotricha), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp (including Pseudoperonospora cubensis, Pseudoperonospora humuli), Pseudopeziza tracheiphila, Puccinia spp (including Puccinia hordei, Puccinia recondita, Puccinia striiformis, PucciniaTriticina)), 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), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp (including T. harzianum, T. pseudokoningii, T. viride), Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp (including V. inaequalis), Verticillium spp, and Xanthomonas spp.

[0160] Within the scope of the present invention, the target crops and / or useful plants to be protected typically include perennial and annual crops, such as berry plants, for example blackberry, blueberry, cranberry, raspberry and strawberry; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar beet and fodder beet, coffee bean, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, such as bermudagrass, bluegrass, bentgrass, centipedegrass, dallisgrass, ryegrass, St. Augustine grass and zoysiagrass; herbs, such as basil, borage, chive, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes, such as kidney bean, lentil, pea and soybean; nuts, such as almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palm plants, such as oil palm; ornamental plants, such as flowers, shrubs and trees; other trees, such as cacao tree, coconut tree, olive tree and rubber tree; vegetables, such as asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, zucchini, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and grapevines, such as grape.

[0161] The term "useful plant" should be understood to include useful plants which, due to conventional breeding methods or genetic engineering, are tolerant to herbicides (such as bromoxynil) or herbicide classes (such as, for example, HPPD inhibitors, ALS inhibitors such as flupyrsulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors). Examples of crops that have been made tolerant to imidazolinones (such as imazamox) by conventional breeding methods (mutagenesis) are summer rape (canola). Examples of crops that have been made tolerant to herbicides or herbicide classes by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties which are commercially available under the Herculex and trade names.

[0162] The term "useful plant" should be understood to also include useful plants which have been transformed by the use of recombinant DNA technology so that they are capable of synthesizing one or more selectively acting toxins, such as those known, for example, from toxin-producing bacteria, in particular those of the genus Bacillus.

[0163] Examples of such plants are: (maize variety expressing the Cry(IA)(b) toxin); YieldGard (maize variety expressing the CryIIIB(b1) toxin); YieldGard (maize variety expressing the Cry(IA)(b) and CryIIIB(b1) toxins); (maize variety expressing the Cry9(c) toxin); Herculex (maize variety expressing the CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) conferring tolerance to the herbicide ammonium glufosinate); NuCOTN (cotton variety expressing the Cry(IA)(c) toxin); Bollgard (cotton variety expressing the Cry(IA)(c) toxin); Bollgard (cotton variety expressing the Cry(IA)(c) and CryI(IA)(b) toxins); (cotton variety expressing the VIP toxin); (potato variety expressing the CryII(IA) toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait), RW (corn rootworm trait) and

[0164] The term "crop" shall be understood to also include crop plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, in particular those of the genus Bacillus.

[0165] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins that colonize nematodes by bacteria, such as Photorhabdus spp. or Xenorhabdus spp., e.g., Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomyces toxins, lectins, e.g., pea lectin, barley lectin or snowdrop lectin; agglutinins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, potato protease inhibitor, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, momordin, saporin or bryodin; steroid metabolic enzymes, such as 3-hydroxy steroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysis inhibitor, HMG-COA-reductase, ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0166] In the context of the present invention, δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, should be understood to clearly also include hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably a protease recognition sequence that does not occur naturally 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).

[0167] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, and WO 03 / 052073. Methods for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Type I Cry deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979, and WO 90 / 13651.

[0168] Toxins contained in transgenic plants confer on the plants tolerance to harmful insects. Such insects can be present in any insect taxon, but are particularly common among beetles (Coleoptera), dipterous insects (Diptera), and moths (Lepidoptera).

[0169] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (maize variety expressing the Cry1Ab toxin); YieldGard (maize variety expressing the Cry3Bb1 toxin); YieldGard (maize variety expressing the Cry1Ab and Cry3Bb1 toxins); (maize variety expressing the Cry9C toxin); Herculex (maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) conferring tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing the Cry1Ac toxin); Bollgard (cotton variety expressing the Cry1Ac toxin); Bollgard (cotton variety expressing the Cry1Ac and Cry2Ab toxins); (cotton variety expressing the Vip3A and Cry1Ab toxins); (potato variety expressing the Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0170] Further examples of such transgenic crops are:

[0171] 1. Bt11 maize, from Syngenta Seeds SAS, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, expressing truncated Cry1Ab toxin by transgene, is conferred resistance to attack by European corn borer (Ostrinia nubilalis and Sesamia nonagrioides). Bt11 maize also expresses PAT enzyme by transgene to obtain tolerance to the herbicide ammonium glufosinate.

[0172] 2. Bt176 maize, from Syngenta Seeds, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, expressing Cry1Ab toxin by transgene, is conferred resistance to attack by European corn borer (Ostrinia nubilalis and Sesamia nonagrioides). Bt176 maize also expresses PAT enzyme by transgene to obtain tolerance to the herbicide ammonium glufosinate.

[0173] 3. MIR604 maize, from Syngenta Seeds, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by expressing a modified Cry3A toxin by transgene. This toxin is Cry3A055 modified by inserting a cathepsin-G protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0174] 4. MON 863 maize, from Monsanto Europe S.A., Avenue de Tervuren 270-272, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0175] 5. IPC 531 cotton, from Monsanto Europe, Avenue de Tervuren 270-272, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0176] 6. 1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize, expressing the protein Cry1F to obtain resistance to certain Lepidoptera insects, and expressing the PAT protein to obtain tolerance to the herbicide ammonium glufosinate.

[0177] 7. NK603×MON 810 maize, from Monsanto Europe S.A., 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of a hybrid maize variety obtained by conventional breeding through crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize expresses transgenically the protein CP4 EPSPS obtained from the Agrobacterium strain CP4 (rendering it tolerant to the herbicide (containing glyphosate)), and also the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki (rendering it tolerant to certain Lepidoptera insects, including the European corn borer).

[0178] Furthermore, to date, no cross-resistance has been observed between the compounds of formula (I), including any of the compounds described in Table 2 (below), and any fungicidal regime for controlling phytopathogenic fungi such as Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terreus), Aureobasidium spp (including A. pullulans), Blastomyces dermatitidis, Blumeria 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, 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, Epidermophyton spp, Erwinia amylovora, Erysiphe spp (including E. cichoracearum), Eutypa lata, Fusarium spp (including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, plants infected with Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp (including H. capsulatum), Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp (including M.graminicola), apple black spot pathogen (M. pomi)), tree tip blight pathogen (Oncobasidium theobromaeon), spruce pathogen (Ophiostoma piceae), Paracoccidioides spp, Penicillium spp (including Penicillium digitatum, Penicillium italicum), Petriellidium spp, Peronosclerospora spp (including Peronosclerospora maydis, Peronosclerospora philippinensis, and Peronosclerospora sorghi), Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp (including Phytophthora infestans), Plasmopara spp (including Plasmopara halstedii, Plasmopara viticola), Pleospora spp, Podosphaera spp (including Podosphaera leucotricha), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp (including Pseudoperonospora cubensis, Pseudoperonospora humuli), Pseudopeziza tracheiphila, Puccinia spp (including Puccinia hordei, Puccinia recondita, Puccinia striiformis, Puccinia triticinatriticina)), Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp (including Magnaporthe oryzae), Pythium spp (including Pythium ultimum), Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp (including Scedosporium apiospermum and Scedosporium prolificans), Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp (including Septoria nodorum and Septoria tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothrix spp, Stagonospora nodorum, Stemphylium spp, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp (including Trichoderma harzianum, Trichoderma pseudokoningii, Trichoderma viride), Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp (including Venturia inaequalis)Species of Septoria, species of Verticillium, and species of Xanthomonas, in particular, Zymoseptoria tritici, Puccinia recondita, Puccinia striiformis, Erysiphe graminis, Uncinula necator, Sphaerotheca fuliginea, Leveillula taurica, Phakopsora pachyrhizi, Pyricularia oryzae, Alternaria solani, Alternaria alternata, Mycosphaerella fijiensis, Colletotrichum lagenarium, Didymella bryoniae, Ascochyta pisii, Verticillium dahliae, Pyrenophora teres, Cercospora beticola, Ramularia collo-cygni, Botrytis cinerea, Sclerotinia sclerotiorum, Monilinia laxa, Monographaella nivalis, and Venturia inaequalis.

[0179] Indeed, fungicide-resistant strains of any of the species outlined above have been reported in the scientific literature, where the strains resistant to one or more fungicides are from at least one of the following fungicidal mode of action classes: quinone outside inhibitors (QoI), quinone inside inhibitors (QiI), succinate dehydrogenase inhibitors (SDHI), and sterol demethylation inhibitors (DMI). Such fungicide-resistant strains can contain:

[0180] · Mutations in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, where the mutation is G143A, F129L or G137R. See, for example: Gisi et al., Pest Manag Sci [Agricultural Pest Control Science] 56, 833 - 841, (2000), Lucas, Pestic Outlook [Pesticide Outlook] 14(6), 268 - 70(2003), Fraaije et al., Phytopathol [Phytopathology] 95(8), 933 - 41(2005), Sierotzki et al., Pest Manag Sci [Agricultural Pest Control Science] 63(3), 225 - 233(2007), Semar et al., Journal of Plant Diseases and Protection [Journal of Plant Diseases and Protection] (3), 117 - 119(2007); and Pasche et al., Crop Protection [Crop Protection] 27(3 - 5), 427 - 435(2008).

[0181] · Mutations in the mitochondrial cytochrome b gene conferring resistance to Qi inhibitors, where the mutation is G37A / C / D / S / V. See, for example: Meunier et al., Pest Manag Sci [Agricultural Pest Control Science] 2019; 75:2107 - 2114.

[0182] · Mutations in the genes encoding SdhB, C, D subunits conferring resistance to SDHI inhibitors, where the mutations are in the following major pathogens:

[0183] ο Botrytis cinerea : B - P225H / L / T / Y / F, B - N230I, B - H272L / Y / R, C - P80H / L, C - N87S;

[0184] ο Alternaria solani: B - H278R / Y, C - H134R / Q, D - D123E, D - H133R and C - H134R;

[0185] ο Septoria 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;

[0186] οPyrenophora teres: In sdhB: S66P, N235I, H277Y. In sdhC: K49E, R64K, N75S, G79R, H134R, S135R. In sdhD: D124E, H134R, G138V, D145G;

[0187] ο Ramularia agrestis : In sdhB: N224T, T267I. In sdhC: N87S, G91R, H146R / L, G171D, H153R;

[0188] ο Phakopsora pachyrhizi: C-I86F;

[0189] ο Sclerotinia sclerotiorum : In sdhB: H273Y. In sdhC: G91R, H146R. In sdhD: T108K, H132R, G150R.

[0190] The main information sources are www.frac.info, Sierotzki and Scalliet Phytopathology (2013) 103(9):880-887 and et al., J Plant Dis Prot (2018) 125:21-2.

[0191] · Mutations or combinations of mutations in the CYP51 gene conferring resistance to DMI inhibitors, where these mutations are: L50S, D134G, V136A / C, Y137F, S188N, A379G, I381V, deletion 459-460, Y461H / S, N513K, S524T. The main information sources 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.

[0192] Thus, in a preferred embodiment, a compound of formula (I) (including any compound described in Table 2 below) or a fungicidal composition according to the invention comprising a compound of formula (I) is used to control fungal strains that are resistant to one or more fungicides from any of the following fungicidal MoA classes: quinone outside inhibitor (QoI), quinone inside inhibitor (QiI), succinate dehydrogenase inhibitor (SDHI), and sterol demethylation inhibitor (DMI).

[0193] As used herein, the term "locality" means the place where a plant grows or on which it grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds are to be placed in the soil. It includes the soil, the seeds and the seedlings, together with the established vegetation.

[0194] The term "plant" means all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0195] The term "plant propagation material" shall be understood to mean the reproductive parts of plants, such as seeds, which parts can be used for the propagation of plants, as well as vegetative material, such as cuttings or tubers (e.g. potatoes). Mention may be made, for example, of seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Mention may also be made of germinated plants and young plants which are to be transplanted after germination or emergence from the soil. These young plants can be protected before transplantation by being treated completely or partially by drenching. Preferably, "plant propagation material" shall be understood to mean seeds.

[0196] The pesticidal agents mentioned herein by their common names are known, for example, from "The Pesticide Manual", 15th Edition, British Crop Protection Council 2009.

[0197] The compounds of formula (I) can be used in unmodified form or, preferably, together with auxiliaries conventionally used in the art of formulation. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusting powders, granules and also encapsulations, for example in polymeric substances. For the type of composition, the method of application is chosen according to the intended purpose and the prevailing circumstances, such as spraying, atomizing, dusting, broadcasting, coating or pouring. The compositions can also contain further auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders or tackifiers, together with fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0198] Suitable carriers and auxiliaries, for example for agricultural use, can be solid or liquid and are substances useful in the art of formulation, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0199] Compounds of formula (I) are generally used in the form of compositions and can be applied to the crop area or the plants to be treated simultaneously or sequentially with further compounds. For example, these further compounds can be fertilizers or micronutrient donors or other preparations which influence plant growth. They can also be selective or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or adjuvants which are customarily used in the art of formulation.

[0200] Compounds of formula (I) can be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, which compositions comprise at least one compound of formula (I) or at least one preferred individual compound as defined above as active ingredient (in free form or in agriculturally available salt form), and comprise at least one of the abovementioned adjuvants.

[0201] The present invention provides a composition, preferably a fungicidal composition, which comprises at least one compound of formula (I), an agriculturally acceptable carrier and optionally adjuvants. An agriculturally acceptable carrier is, for example, a carrier which is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I), the composition can also comprise at least one or more pesticidal active compounds, for example further fungicidal active ingredients.

[0202] The compound of formula (I) can be the sole active ingredient of the composition, or, where appropriate, it can be mixed with one or more further active ingredients, such as pesticidal agents, fungicides, synergists, herbicides or plant growth regulators. In some cases, the further active ingredients can result in unexpected synergistic activity.

[0203] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzoyl aniline fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged biphenyl fungicides, carbamate fungicides, phenylcarbamate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furanamide fungicides, furan aniline fungicides, hydrazide fungicides, imidazole fungicides, morpholine fungicides, organophosphorus fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylthioamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolo pyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

[0204] Examples of suitable additional active ingredients also include the following: petroleum oils, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenyl sulfone, acetoprole, aldoxycarb, azadirachtin, chlorpyrifos, amiton, amiton hydrogen oxalate, amitraz, bromopropylate, azobenzene, azinphos, benomyl, benoxafos, benzyl benzoate, bixafen, brofenprox, bromocylen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, octachlorostyrene, chlorfenvinphos, carbophenothion, chinomethionat, chlorobenzilate, chlorfenson, chlorfensulphide, chlorfenthion, chlorobenzilate, chloromebuform, chlorfluazuron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerin, clofentezine, crotamiton, crotoxyphos, cyhexatin, cyflumetofen, cyanophos, cyanofenphos, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulfon, dichlofluanid, dichlorvos, dicliphos, dicofol, dimefox, dinocap, dinocap-diclexine, dinocap-4, dinocap-6, dinocap-o, dinoseb, dinoseb acetate, dinoseb nitrate, dioxathion, diphenyl sulfone, disulfiram, DNOC, dofenapyn, doramectin, dioxathion, emamectin, ethion, ethionamide, etoxazole, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenson, fentrifanil, flufenzin, flucycloxuron, flubenzimine, flufenerim, FMC1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, guazatine, hexythiazox, hexadecyl cyclopropanecarboxylate, jasmolin I, jasmolin II, iodoethane, propargite, isocarbophos, isoxathion, methiocarb, methomyl, methoprene, milbemycin, naled, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, hexaflumuron, nikkomycin, penthiocarb, penthiocarb 1:1 zinc chloride complex, omethoate, isofenphos-methyl, sulfotep, pp'-DDT, permethrin, phenthoate, phosalone, phosfolan, polychloroterpenes, polynactins, propachlor, pyridaphenthion, propoxur, ethoprophos, pyraclofos, pyrethrin I, pyrethrin II, pyrethrin, pyridathion, pyrimiphos-methyl, quinalphos, quintiofos, R-1492,Glyphosate, rotenone, octamethrin, clomiphene, selamectin, thiothion, SSI-121, sulfilam, sulfotep, sulfur, flumethoxine, τ-fluvalinate, TEPP, tert-butylcarb, tetrachlorothiazide, thiafenox, thiafenox, long-acting carb, methyl thiocarb, thiocarb, thiocarb, triazophos, triazuron, trichloropropoxyphos, triamcinol, aphidazole, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, cybutryne, dichloronaphthoquinone, dichlorophen, fungicidal acid, triphenyltin, slaked lime, sodium mancozeb, Algaquinone, quinone, simazine, triphenyltin acetate, triphenyltin hydroxide, fusulin, piperazine, thiophanate, chloralose, fenthion, pyridine-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxaline-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, disipirthion, dodesine, sodium sulfone, formaldehyde, kasugamycin, kasugamycin hydrochloride hydrate, nickel di(dimethyldithiocarbamate), trichloromethylpyridine, octhiothionone, oxolinic acid, oxytetracycline, hydroxyquinoline potassium sulfate, thiabendazole, streptomycin, streptomycin sesquisulfate, phyllotoxin, cotton brown banded tormentor GV, radiobacterium, Amblyseius species (Amblyseius spp.), celery armyworm NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Spodoptera exigua NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Codling moth GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora) and Heterorhabditis megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus,Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and Neodiprion lecontei NPV, Orius species, Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma species, Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, urethane imine, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E,Z)-tetradec-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-heneicos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodec-7,9-dien-1-yl acetate,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol and 4-methylnonan-5-one, α-multistriatin, western pine beetle aggregation pheromone, codlelure, codlemone, cuelure, epoxy nonadecane, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methylcaprylate, eugenol, southern pine beetle aggregation pheromone (frontalin), grandlure, grandlure I, grandlure II, grandlure III, grandlure IV, hexalure, ipsdienol, ipsenol, japonilure, lineatin, litlure, looplure, medlure, megatomoic acid, methyleugenol, muscalure, octadeca-2,13-dien-1-yl acetate, octadeca-3,13-dien-1-yl acetate, orfralure, oryctalure, ostramone, siglure, sordidin, sulcatol, tetradec-11-en-1-yl acetate, trimedlure, trimedlure A, trimedlure B1, trimedlure B2, trimedlure C, trunc-call, 2-(octylthio)ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethylcarbate, dimethyl phthalate, 2-ethylhexan-1,3-diol, hexamide, methoquin-butyl, methylneodecanamide, oxamate, picaridin, 1,1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate,2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphonate, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate, 2-(4-chloro-3,5-dimethylphenoxy)ethanol, 2-chlorovinyl diethylphosphate, 2-imidazolidinone, 2-isovalerylindane-1,3-dione, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-cyanothioethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-dimethylphenyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, acephate, acrylonitrile, alomycin, asana, alpha-ecdysone, aluminium phosphide, aminocarb, neonicotinoid, athidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, bioallethrin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, bioresmethrin, bis(2-chloroethyl) ether, borax, bromfenvinfos, bromo-DDT, bufencarb, butacarb, butathiofos, butonate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, cevadine, chlorthiophos, chlordane, chlordecone, chloroform, chloropicrin, cyanofenphos, chlorprazophos, cis-resmethrin, cismethrin, clocythrin, copper oleate, coumithoate, cryolite, CS 708, cyanofenphos, cyanophos, cycloprothrin, cythioate, d-allethrin, DAEP, dazomet, decarbofuran, diamidafos, isocarbophos, dichlofenthion, dicresyl, cyromazine, diethyl 5-methylpyrazol-3-yl phosphate, dilor, dimefluthrin, dimecarb, dimethylvinphos, dioxacarb, dinoseb, ethofenprox, esfenvalerate, etaphos, ethiofencarb, ethyl formate, dichloroethane, ethylene oxide, EXD, fenthion, etobenzanid, fenitrothion, fenoxacrim, fenpyroximate, fensulfothion, fenthion, flucofuron, butylphos, cadusafos, furathiocarb, pyrethrum, guazatine, guazatine acetate,Sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, dichlofenthion, HHDN, hydrogen cyanide, quinocarb, IPSP, chlorazophos, carbophenothion, isodrin, isofenphos, transplanting agent, isoprothiolane, oxydemeton-methyl, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorprene, kinoprene, bromfenvinfos, acetamiprid, fosthiazate, m-tolyl methylcarbamate, azinphos-methyl, demeton-methyl, methidathion, methanesulfinylphosphate, metam, metam-potassium, metam-sodium, methylsulfonyl fluoride, butamifos, methoprene, pyrethrins, methoxychlor, methyl isothiocyanate, methyl chloroform, dichloromethane, insectoxan, mirex, naled, nicotine, nicotine sulfate, nithiazine, nor-nicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-ylphosphonothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphonothioate, O,O,O',O'-tetrapropyl pyrophosphorodithioate, oleic acid, p-dichlorobenzene, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, fenthion, parathion, phosphine, phoxim-methyl, amiprofos-methyl, polychlorodicyclopentadiene isomers, potassium thiocyanate, precocene I, precocene II, precocene III, amidithion, profluthrin, BPMC, profenofos, pyrazophos, transfluthrin, quassia, quinalphos-methyl, chlorthiophos, iodoxamide, resmethrin, rotenone, thenylchlor, ryanodine, leonardine, sabadilla, schradan, cadusafos, SI-0009, thiphenamil, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenate, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar, pirimicarb, TDE, butathiofos, temephos, allethrin, 1,1,2,2-tetrachloroethane, thichlorfon, thiosultap, thiosultap oxalate, ethoprophos, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetaphos-3, trichloronate, BPMC, tolprocarb, picoxystrobin, methoprene, veratridine, veratrine, XMC, zetamethrin, azamethiphos, and meperfluthrin, tetraflumethrin, bis(tributyltin) oxide, bromoacetamide, iron phosphate, niclosamide ethanolamine, tributyltin oxide, pyrimorph, nicobifen, 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, anisiflupurin,Benclothiaz, cytokinin, DCIP, furfural, isamidofos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, benzoic acid, benzoic acid-S-methyl, Reynoutria sachalinensis extract, α-chloroalcohol, warfarin, barium carbonate, difenacoum, bromadiolone, bromethalin, bromoacetamide, chlorophacinone, cholecalciferol, chlorophacinone, coumatetralyl, coumatetralyl, difethialone, thiafentanil, diphacinone, calciferol, flocoumafen, fluoroacetamide, fluridone, fluridone hydrochloride, lasiotexin, phosdrin, phosphorus, pival, pyrinuron, scilliroside, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, piperonyl butoxide, MGK 264, piperonyl butoxide, piperonal butoxide, piperonyl propyl isomer, S421, piperonyl sulfoxide, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, silafluofen, zinc naphthenate, ziram, emamectin benzoate, ribavirin, indoleacetic hydrazide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyridinitril, simeconazole, tebuconazole, triflumizole, triadimefon, triadimenol, triticonazole, ancymidol, fenarimol, fluoroimide, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, fenoxanil, pyrimethanil; metalaxyl-M, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl; ofurace, oxadixyl, carbendazim, debacarb, dimethirimol, thiabendazole, chlozolinate, dichlozoline, myclozoline, procymidone, vinclozoline, boscalid, carboxin, mepronil, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, guazatine,Azoxystrobin, dimoxystrobin, enestroburin, enoxastrobin, fluacrypyrim, fluoxastrobin, kresoxim-methyl, metominostrobin, tricyclazole, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, zoxamide, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, fluxapyroxad, 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (3’,4’,5’-trifluoro-biphenyl-2-yl)-amide, isoflucypram, isofetamid, dipymetitrone, amisulbrom, anilazine, azaconazole, benalaxyl, benodanil, benomyl, benthiavalicarb, boscalid, bromuconazole, captan, carbendazim, carboxin, carpropamid, chlorothalonil, cyazofamid, cymoxanil, cyproconazole, cyprodinil, difenoconazole, dimethomorph, diniconazole, dinocap, dithianon, dodine, edifenphos, epoxiconazole, ethaboxam, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenhexamid, fenoxanil, ferimzone, fluazinam, flumetylsulforim, fluopicolide, fluopyram, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, flutriafol, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, metiram, metrafenone, myclobutanil, nabam, nickel dimethyldithiocarbamate, nuarimol, ofurace, oxadixyl, oxycarboxin, penconazole, pencycuron, phosethyl-Al, picoxystrobin, polyoxin, propamocarb, proquinazid, pyroquilon, pyriofenone, quinoxyfen, quintozene, tebuconazole, thiabendazole, thifluzamide, thiram, tricyclazole, trifloxystrobin, validamycin, valifenalate, ziram, zoxamide,6-Ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithieno[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, jiaxiangjunzhi, lvbenmixianan, dichlobentiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiprolin, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamic acid tert-butyl ester, pyraziflumid, trolprocarb, cyflufenamid, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chlorophenyl]methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamic acid but-3-ynyl ester, N-[[5-[4-(2,4-dimethylphenyl)-1,2,4-triazol-2-yl]-2-methylphenyl]methyl]carbamic acid methyl ester, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridachlometyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide,1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]-4-methyl-1H-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]-1H-tetrazol-5-one, aminopyrifen, amisulbrom, indaziflam, fluopyram, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide, florylpicoxamid, fenpicoxamid, metarylpicoxamid, isobutyl ethyoxquinoline, ipflufenoquin, quinofumelin, isopropylthianil, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, benzothiazole ester, cyanovirin-N, zinc 5-amino-1,3,4-thiadiazole-2-thiolate (2:1), fluopyram, flufenoxadiazam, flutianil, fluoxastrobin, pyrapropoyne, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylinden-4-yl)nicotinamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)nicotinamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile, metyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)nicotinamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac-ethyl, pyribencarb, zhongshengmycin, thiodiazole copper, thiazole zinc, amectotractin, iprodione, seboctylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared by the methods 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 by the methods described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared by the methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared by the methods described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide,N-[(1R)-1-Benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the methods described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared by the methods described in WO2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolinyl)-7,8-dihydro-6H-cyclopentadieno[e]benzimidazole (these compounds can be prepared by the methods 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-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared by the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithia[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared by the method described in WO2011 / 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-enamine (this compound can be prepared by the method described in WO2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in WO2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675); (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 by the method 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 by the method described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared by the method described in WO2018 / 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-carbamimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428).

[0205] The compounds of the present invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from macrolide compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives such as those described in EP-357460, EP-444964, and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives such as those described in US-5015630, WO-9415944, and WO-9522552. Additional anthelmintic agents include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintic agents include trematocides (such as triclabendazole and clorsulon) and cestocides (such as praziquantel and niclosamide).

[0206] The compounds of the present invention can be used in combination with derivatives and analogs of paraherquamide / marcfortine class anthelmintic agents together with anti-parasitic oxazolines (such as those disclosed in US-5478855, US-4639771, and DE-19520936).

[0207] The compounds of the present invention can be used in combination with derivatives and analogs of general class dioxolane anti-parasitic agents as described in WO-9615121 and also with cyclic depsipeptides having anthelmintic activity (such as those described in WO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538).

[0208] The compounds of the present invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as chlorfenapyr; ecdysteroid agonists such as tebufenozide, etc.; neonicotinoids such as imidacloprid, etc.

[0209] The compounds of the present invention can be used in combination with terpenoid alkaloids such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0210] Other examples of such bioactive compounds that can be used in combination with the compounds of the present invention include, but are not limited to, the following: Organophosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Chlorethoxyphos, Chlorpyrifos, Chlorethoxyfos, Chlorfenvinphos, Demeton, Demeton-S-methyl, Demeton-S-methyl sulfone, Dialifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Etrimfos, Famphur, Fenitrothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosthiazate, Heptenophos, Isazofos, Isopropyl parathion, Isoxathion, Malathion, Methacrifos, Methamidophos, Methidathion, Methyl demeton, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Paraoxon, Phenthoate, Phosalone, Phosphocarb, Phosmet, Phoxim, Pirimiphos-methyl, Profenofos, Proetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tefamiphos, Terbufos, Tetrachlorvinphos, Thimeton, Triazophos, Trichlorfon, Trimethacarb.

[0211] Carbamates: Aldicarb, Aldicarb sulfoxide, Aldicarb sulfone, Bendiocarb, Benfuracarb, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenoxycarb, Fenothiocarb, Formetanate, Isoprocarb, Indoxacarb, Methiocarb, Methomyl, 5-Methyl-m-isopropylphenyl butynyl (methyl) carbamate, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, UC-51717.

[0212] Pyrethroids: Acrinathrin, Allethrin, Alpha-cypermethrin, 5-Benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate, Bifenthrin, Beta-cyfluthrin, Cyfluthrin, Cypermethrin, Cyhalothrin, Deltamethrin, Empenthrin, Esfenvalerate, Etofenprox, Fenpropathrin, Flucythrinate, Fluvalinate, Flumethrin, Imiprothrin, Lambda-cyhalothrin, Permethrin, Phenothrin, Pyrethrins (natural products), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Theta-cypermethrin, Tralomethrin, Zeta-cypermethrin.

[0213] Arthropod growth regulators: a) Chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, flufenprox, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, ethofenprox, hexythiazox, etoxazole, chlorfentazine; b) Ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) Juvenile hormone analogs: pyriproxyfen, methoprene (including S-methoprene), phenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.

[0214] Other antiparasitic drugs: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, cartap, chlorobenzilate, chlorfenapyr, chromafenozide, clothianidin, cyanaguanide, diacloden, dimite, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, flufenerim, flufenzin, flutriafol, fluthrin, flufenoxur, fluvalinate, halofenprox, hydramethylnon, IKI-220, hydrocerussite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbute, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, pyridaben, tetradifon, tetraene antibiotics, thiacloprid, thiosultap, thiamethoxam, tolfenpyrad, triazamate, triacetoxyscirpenol, veralox, YI-5301.

[0215] Biological agents: Bacillus thuringiensis ssp aizawai, Bacillus thuringiensis ssp kurstaki, Bacillus thuringiensis δ-endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0216] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0217] Other biocides: enrofloxacin, febantel, penethamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, thiomurin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiofur, carprofen, mefronil, praziquantel, triclabendazole.

[0218] Another aspect of the invention relates to the use of a compound of formula (I), or preferably of an individual compound as defined above, of a composition comprising at least one compound of formula (I) or at least one preferably individual compound as defined above, or of a fungicidal or insecticidal mixture as defined above comprising at least one compound of formula (I) or at least one preferably individual compound as defined above, in admixture with other fungicides or insecticides, for controlling or preventing plants (such as useful plants (such as crop plants)), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or inanimate materials from being infested by insects or phytopathogenic microorganisms (preferably fungal organisms).

[0219] Another aspect of the invention relates to a method for controlling or preventing plants (such as useful plants (such as crop plants)), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or inanimate materials from being infested by insects or phytopathogenic or putrefactive microorganisms or organisms potentially harmful to humans (especially fungal organisms), which method comprises applying a compound of formula (I) or preferably an individual compound as defined above as an active ingredient to the plants, parts of the plants or to their site, their propagation materials, or any part of the inanimate materials.

[0220] Controlling or preventing means reducing the infestation by insects or phytopathogenic microorganisms or putrefactive microorganisms or organisms potentially harmful to humans (especially fungal organisms) to a proven improved level.

[0221] A preferred method of controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects is foliar application, which comprises applying a compound of formula (I), or an agrochemical composition containing at least one such compound. The application frequency and the application rate will depend on the risk of infestation by the respective pathogen or insect. However, the compound of formula (I) can also penetrate the plant via the soil through the roots (systemic action) by soaking the locus of the plant with a liquid formulation or by applying the compound in solid form, for example in granular form, to the soil (soil application). In rice crops, such granules can be applied to flooded paddy 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.

[0222] Formulations (such as compositions containing a compound of formula (I) and, if desired, solid or liquid auxiliaries or monomers for encapsulating the compound of formula (I)) can be prepared in a known manner, typically by intimately mixing and / or grinding the compound with extenders such as solvents, solid carriers and optionally surface-active compounds (surfactants).

[0223] Advantageous application rates are generally from 5 g to 2 kg of active ingredient (a.i.) / hectare (ha), preferably from 10 g to 1 kg a.i. / ha, most preferably from 20 g to 600 g a.i. / ha. When used as a seed soaking agent, suitable dosages are from 10 mg to 1 g of active substance / kg of seeds.

[0224] When the combination according to the invention is used for treating seeds, a rate of 0.001 to 50 g of the compound of formula (I) / kg of seeds, preferably from 0.01 to 10 g / kg of seeds, is generally sufficient.

[0225] The compositions of the present invention can be used in any conventional form, for example, in the form of two-pack, powder for dry seed treatment (DS), emulsion for seed treatment (ES), flowable concentrate for seed treatment (FS), solution for seed treatment (LS), water dispersible powder for seed treatment (WS), capsule suspension for seed treatment (CF), gel for seed treatment (GF), emulsion concentrate (EC), suspension concentrate (SC), suspoemulsion (SE), capsule suspension (CS), water dispersible granule (WG), emulsifiable granule (EG), water-in-oil emulsion (EO), oil-in-water emulsion (EW), microemulsion (ME), oil dispersion (OD), oil suspension (OF), oil-soluble liquid (OL), soluble concentrate (SL), ultra-low volume suspension (SU), ultra-low volume liquid (UL), technical concentrate (TK), dispersible concentrate (DC), wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0226] Such compositions can be produced in a conventional manner, for example, by mixing the active ingredient with suitable formulating inert agents (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, antifreezes, adhesives, thickeners and compounds providing adjuvant effects). Conventional slow-release formulations designed for long-lasting efficacy can also be used. In particular, formulations to be applied in spray form, such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, can contain surfactants such as wetting agents and dispersants and other compounds providing adjuvant effects, such as condensation products of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0227] Using the combination and diluent of the present invention, in the form of a suitable seed dressing formulation, such as an aqueous suspension or dry powder with good adhesion to seeds, the seed dressing formulation is applied to the seeds in a manner known per se. Such seed dressing formulations are known in the art. The seed dressing formulation can contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as slow-release capsules or microcapsules.

[0228] Generally, the formulation comprises from 0.01% to 90% by weight of an active ingredient, from 0 to 20% of an agriculturally acceptable surfactant and 10% to 99.99% of a solid or liquid formulation inert agent and one or more adjuvants, and the active agent is composed of at least a compound having formula (I) together with components (B) and (C), and optionally other active agents (especially microbicides or preservatives or the like). In the form of a concentrate of the composition, it generally contains, by weight, between about 2% and 80%, preferably between about 5% and 70% of the active agent. The application form of the formulation may contain, for example, from 0.01% to 20% by weight, preferably from 0.01% to 5% by weight of the active agent. However, commercial products will preferably be formulated as concentrates, and the end user will generally use diluted formulations.

[0229] Table 1 below shows examples of individual compounds having formula (I) according to the present invention.

[0230] Table A-1 Forty-eight compounds A-1.001 to A-1.048 having formula (Ib) are provided

[0231]

[0232] wherein A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-3-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0233] Table 1: Individual compounds having formula (I) according to the present invention

[0234]

[0235]

[0236]

[0237] Table A-2 Forty-eight compounds A-2.001 to A-2.048 having formula (Ib) are provided, wherein A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-3-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0238] Table A-3 Forty-eight compounds of formula (Ib), A-3.001 to A-3.048, are provided, where A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-2-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0239] Table A-4 Forty-eight compounds of formula (Ib), A-4.001 to A-4.048, are provided, where A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-2-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0240] Table A-5 Forty-eight compounds of formula (Ib), A-5.001 to A-5.048, are provided, where A is N, R 7 is hydrogen, R 1 is oxetan-3-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0241] Table A-6 Forty-eight compounds of formula (Ib), A-6.001 to A-6.048, are provided, where A is N, R 7 is hydrogen, R 1 is oxetan-3-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0242] Table A-7 Forty-eight compounds of formula (Ib), A-7.001 to A-7.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylsulfonylethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R8 is as defined in Table 1.

[0243] Table A-8 Forty-eight compounds of formula (Ib), A-8.001 to A-8.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylsulfonylethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0244] Table A-9 Forty-eight compounds of formula (Ib), A-9.001 to A-9.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylsulfinylethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0245] Table A-10 Forty-eight compounds of formula (Ib), A-10.001 to A-10.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylsulfinylethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0246] Table A-11 Forty-eight compounds of formula (Ib), A-11.001 to A-11.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylthioethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0247] Table A-12 Forty-eight compounds of formula (Ib), A-12.001 to A-12.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methylthioethyl, R 2is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0248] Table A-13 Forty-eight compounds of formula (Ib), A-13.001 to A-13.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0249] Table A-14 Forty-eight compounds of formula (Ib), A-14.001 to A-14.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-methoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0250] Table A-15 Forty-eight compounds of formula (Ib), A-15.001 to A-15.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-isopropoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0251] Table A-16 Forty-eight compounds of formula (Ib), A-16.001 to A-16.048, are provided, where A is N, R 7 is hydrogen, R 1 is 1-isopropoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0252] Table A-17 Forty-eight compounds of formula (Ib), A-17.001 to A-17.048, are provided, where A is N, R7 is hydrogen, R 1 is 1-tert-butoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0253] Table A-18 There are provided 48 compounds of formula (Ib), A-18.001 to A-18.048, wherein A is N, R 7 is hydrogen, R 1 is 1-tert-butoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0254] Table A-19 There are provided 48 compounds of formula (Ib), A-19.001 to A-19.048, wherein A is N, R 7 is hydrogen, R 1 is isopropoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0255] Table A-20 There are provided 48 compounds of formula (Ib), A-20.001 to A-20.048, wherein A is N, R 7 is hydrogen, R 1 is isopropoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0256] Table A-21 There are provided 48 compounds of formula (Ib), A-21.001 to A-21.048, wherein A is N, R 7 is hydrogen, R 1 is tert-butoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0257] Table A-22Forty-eight compounds of formula (Ib), A-22.001 to A-22.048, are provided, where A is N, R 7 is hydrogen, R 1 is tert-butoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0258] Table A-23 Forty-eight compounds of formula (Ib), A-23.001 to A-23.048, are provided, where A is N, R 7 is -C(O)2CH3, R 1 is tetrahydrofuran-3-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0259] Table A-24 Forty-eight compounds of formula (Ib), A-24.001 to A-24.048, are provided, where A is N, R 7 is -C(O)2CH3, R 1 is tetrahydrofuran-3-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0260] Table A-25 Forty-eight compounds of formula (Ib), A-25.001 to A-25.048, are provided, where A is N, R 7 is -C(O)2CH3, R 1 is tetrahydrofuran-2-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0261] Table A-26 Forty-eight compounds of formula (Ib), A-26.001 to A-26.048, are provided, where A is N, R 7 is -C(O)2CH3, R 1 is tetrahydrofuran-2-yl, R 2 is fluorine, and R 4 、R 5, R 6 and R 8 are as defined in Table 1.

[0262] Table A-27 Forty-eight compounds of formula (Ib), A-27.001 to A-27.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is oxetan-3-yl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0263] Table A-28 Forty-eight compounds of formula (Ib), A-28.001 to A-28.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is oxetan-3-yl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0264] Table A-29 Forty-eight compounds of formula (Ib), A-29.001 to A-29.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methylsulfonylethyl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0265] Table A-30 Forty-eight compounds of formula (Ib), A-30.001 to A-30.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methylsulfonylethyl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0266] Table A-31 Forty-eight compounds of formula (Ib), A-31.001 to A-31.048, are provided, wherein A is N, R7 is -C(O)2CH3, R 1 is 1-methylsulfonylethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0267] Table A-32 There are provided 48 compounds of formula (Ib), A-32.001 to A-32.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methylsulfonylethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0268] Table A-33 There are provided 48 compounds of formula (Ib), A-33.001 to A-33.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methylthioethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0269] Table A-34 There are provided 48 compounds of formula (Ib), A-34.001 to A-34.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methylthioethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0270] Table A-35 There are provided 48 compounds of formula (Ib), A-35.001 to A-35.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8is as defined in Table 1.

[0271] Table A-36 Forty-eight compounds of formula (Ib), A-36.001 to A-36.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-methoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0272] Table A-37 Forty-eight compounds of formula (Ib), A-37.001 to A-37.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-isopropoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0273] Table A-38 Forty-eight compounds of formula (Ib), A-38.001 to A-38.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-isopropoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0274] Table A-39 Forty-eight compounds of formula (Ib), A-39.001 to A-39.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1 is 1-tert-butoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 is as defined in Table 1.

[0275] Table A-40 Forty-eight compounds of formula (Ib), A-40.001 to A-40.048, are provided, wherein A is N, R 7 is -C(O)2CH3, R 1is 1-tert-butoxyethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0276] Table A-41 There are provided 48 compounds of formula (Ib), A-41.001 to A-41.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is isopropoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0277] Table A-42 There are provided 48 compounds of formula (Ib), A-42.001 to A-42.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is isopropoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0278] Table A-43 There are provided 48 compounds of formula (Ib), A-43.001 to A-43.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is tert-butoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0279] Table A-44 There are provided 48 compounds of formula (Ib), A-44.001 to A-44.048, wherein A is N, R 7 is -C(O)2CH3, R 1 is tert-butoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0280] Table A-45Forty-eight compounds of formula (Ib), A-45.001 to A-45.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is tetrahydrofuran-3-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0281] Table A-46 Forty-eight compounds of formula (Ib), A-46.001 to A-46.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is tetrahydrofuran-3-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0282] Table A-47 Forty-eight compounds of formula (Ib), A-47.001 to A-47.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is tetrahydrofuran-2-yl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0283] Table A-48 Forty-eight compounds of formula (Ib), A-48.001 to A-48.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is tetrahydrofuran-2-yl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0284] Table A-49 Forty-eight compounds of formula (Ib), A-49.001 to A-49.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is oxetan-3-yl, R 2 is hydrogen, and R4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0285] Table A-50 Forty-eight compounds of formula (Ib), A-50.001 to A-50.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is oxetan-3-yl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0286] Table A-51 Forty-eight compounds of formula (Ib), A-51.001 to A-51.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylsulfonylethyl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0287] Table A-52 Forty-eight compounds of formula (Ib), A-52.001 to A-52.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylsulfonylethyl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0288] Table A-53 Forty-eight compounds of formula (Ib), A-53.001 to A-53.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylsulfinylethyl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0289] Table A-54Forty-eight compounds of formula (Ib), A-54.001 to A-54.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylsulfinylethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0290] Table A-55 Forty-eight compounds of formula (Ib), A-55.001 to A-55.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylthioethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0291] Table A-56 Forty-eight compounds of formula (Ib), A-56.001 to A-56.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methylthioethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0292] Table A-57 Forty-eight compounds of formula (Ib), A-57.001 to A-57.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methoxyethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0293] Table A-58 Forty-eight compounds of formula (Ib), A-58.001 to A-58.048, are provided, wherein A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-methoxyethyl, R 2 is fluorine, and R4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0294] Table A-59 Forty-eight compounds of formula (Ib), A-59.001 to A-59.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-isopropoxyethyl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0295] Table A-60 Forty-eight compounds of formula (Ib), A-60.001 to A-60.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-isopropoxyethyl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0296] Table A-61 Forty-eight compounds of formula (Ib), A-61.001 to A-61.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-tert-butoxyethyl, R 2 is hydrogen, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0297] Table A-62 Forty-eight compounds of formula (Ib), A-62.001 to A-62.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is 1-tert-butoxyethyl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0298] Table A-63Forty-eight compounds of formula (Ib), A-63.001 to A-63.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is isopropoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0299] Table A-64 Forty-eight compounds of formula (Ib), A-64.001 to A-64.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is isopropoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0300] Table A-65 Forty-eight compounds of formula (Ib), A-65.001 to A-65.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is tert-butoxymethyl, R 2 is hydrogen, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0301] Table A-66 Forty-eight compounds of formula (Ib), A-66.001 to A-66.048, are provided, where A is N, R 7 is -C(O)2CH2CH3, R 1 is tert-butoxymethyl, R 2 is fluorine, and R 4 、R 5 、R 6 and R 8 are as defined in Table 1.

[0302] Table A-67 Twelve compounds of formula (Ib), A-67.001 to A-66.012, are provided, where A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-4-yl, R 2 is hydrogen, and R 4 、R5 , R 6 and R 8 are as defined in Table 1.

[0303] Table A-68 Twelve compounds A-68.001 to A-68.012 of formula (Ib) are provided, where A is N, R 7 is hydrogen, R 1 is tetrahydrofuran-4-yl, R 2 is fluorine, and R 4 , R 5 , R 6 and R 8 are as defined in Table 1.

[0304] Formulation Examples

[0305]

[0306] The active ingredient is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable grinder to provide a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0307]

[0308] The active ingredient is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable grinder to provide a powder that can be used directly for seed treatment.

[0309] Emulsifiable Concentrates

[0310]

[0311] An emulsion of any required dilution that can be used in plant protection can be obtained by diluting with water from this concentrate.

[0312]

[0313] A ready-to-use dust powder is obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such powders can also be used for dry dressing of seeds.

[0314] Extruder Granules

[0315]

[0316] The active ingredient is mixed with adjuvants and ground, and the mixture is wetted with water. The mixture is extruded and then dried in an air stream.

[0317] Coated Granules

[0318] Active ingredient [compound of formula (I)] 8%

[0319] Polyethylene glycol (molecular weight 200) 3%

[0320] Kaolin 89%

[0321] The finely ground active ingredient is uniformly applied in a mixer to kaolin moistened with polyethylene glycol. Dust-free coated granules are obtained in this way.

[0322] Suspension Concentrates

[0323]

[0324]

[0325] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation material can be treated and protected against microbial infestation by spraying, pouring or dipping.

[0326] Flowable Concentrates for Seed Treatment

[0327]

[0328] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation material can be treated and protected against microbial infestation by spraying, pouring or dipping.

[0329] Sustained Release Capsule Suspensions

[0330] 28 parts of a combination of compounds of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 part of an antifoaming agent and 51.6 parts of water until the desired particle size is reached. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water are added to this emulsion. The mixture is stirred until the polymerization reaction is complete.

[0331] The obtained capsule suspension is stabilized by adding 0.25 parts of a thickening agent and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the medium capsules is 8 - 15 microns.

[0332] The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

[0333] Examples

[0334] The following examples are used to illustrate the present invention. The compounds of the present invention may differ from known compounds in greater efficacy at low application rates, which can be confirmed by those skilled in the art using the experimental procedures outlined in the examples, using lower application rates (if necessary), for example, 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0335] Compounds having the formula (I) can have any number of benefits, including in particular favorable levels of biological activity for protecting plants against diseases caused by fungi or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, favorable activity spectra, increased safety (including improved crop tolerance), improved physico - chemical properties, or increased biodegradability).

[0336] List of Abbreviations

[0337] °C = degrees Celsius, CDCl3 = deuterochloroform, d = doublet, DCM = dichloromethane, DMF = dimethylformamide, HATU = 1 - [bis(dimethylamino)methylene] - 1H - 1,2,3 - triazolo[4,5 - b]pyridinium 3 - oxide hexafluorophosphate, m = multiplet, MHz = megahertz, N = normal, RT = room temperature, s = singlet

[0338] General

[0339] Throughout this specification, temperatures are given in degrees Celsius (°C) and "m.p." means melting point. LC / MS means liquid chromatography - mass spectrometry, and the description of the apparatus and methods is:

[0340] Method A: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 mm particle size, 30 x 2.1 mm column, 0.85 mL / min., 60 °C, H2O / MeOH 95:5 + 0.05% HCOOH (90%) / CH3CN + 0.05% HCOOH (10%) - 1.2 min. - CH3CN + 0.05% HCOOH (100%) - 0.30 min., ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: positive ion; capillary voltage (kV) 3.00, cone voltage (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone gas flow rate (L / Hr) 0, desolvation gas flow rate (L / Hr) 650).

[0341] Method B: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 mm particle size, 30 x 2.1 mm column, 0.85 mL / min., 60 °C, H2O / MeOH 95:5 + 0.05% HCOOH (90%) / CH3CN + 0.05% HCOOH (10%) - 2.7 min. - CH3CN + 0.05% HCOOH (100%) - 0.30 min., ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: positive ion; capillary voltage (kV) 3.00, cone voltage (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone gas flow rate (L / Hr) 0, desolvation gas flow rate (L / Hr) 650).

[0342] Method C: ACQUITY mass spectrometer from Waters Corporation (SQD or SQDII single quadrupole mass spectrometer), the mass spectrometer is equipped with an electrospray source (polarity: positive ion or negative ion, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow rate: 60 L / hr, desolvation gas flow rate: 700 L / hr; mass range: 140 Da to 800 Da), and ACQUITY UPLC from Waters Corporation (with solvent degassing device, binary pump, heated column chamber and diode array detector). Column: Waters UPLC HSS T3, 1.8 μm, 30 x 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 400, solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid, gradient: 0% - 100% B, within 2.5 min; flow rate (ml / min) 0.75.

[0343] Example 1 : Preparation of 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-2, Table 2) and 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (Example P-1, Table 2)

[0344]

[0345]

[0346] Under argon, a solution of tetrahydrofuran-3-carboxylic acid (0.174 g, 0.143 mL, 1.48 mmol) in DCM (9 mL) was treated with 1 drop of DMF, followed by oxalyl chloride (0.192 g, 0.13 mL, 1.48 mmol). The mixture was stirred at RT under argon for 30 minutes to generate tetrahydrofuran-3-carbonyl chloride. Under argon at RT, 2-[(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (0.350 g, 0.993 mmol, prepared as in WO2019 / 105933) was added to this DCM solution, followed by triethylamine (0.308 g, 0.42 mL, 2.98 mmol). The resulting pale yellow solution was stirred at RT under argon for 2.5 hours, at which point LCMS analysis showed completion of the reaction. The reaction mixture was washed with Processed and concentrated in vacuo. Purified by flash chromatography (eluting with ethyl acetate / cyclohexane) to give a mixture of two products which was further purified by reverse phase chromatography to yield 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide as a white powder, the first elution product (Example P-2, Table 2).

[0347] 1 H NMR (400 MHz, CDCl3): δ ppm 0.94 (s, 3H) 1.13 (s, 3H) 1.49 - 1.59 (m, 2H) 1.65 - 1.78 (m, 1H) 1.95 - 2.15 (m, 1H) 2.19 - 2.30 (m, 1H) 2.30 - 2.40 (m, 1H) 2.81 (s, 3H) 2.99 - 3.14 (m, 1H) 3.80 - 3.88 (m, 1H) 3.88 - 3.95 (m, 1H) 3.95 - 4.06 (m, 2H) 4.10 - 4.26 (quintet, 1H) 6.89 (s, 2H) 6.95 - 7.06 (broad d, 1H);

[0348] LC-MS (Method A): 451 [M+H], Rt: 1.09 min.

[0349] Further elution yielded the second product as a white powder, 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (Compound P-1, Table 2).

[0350] 1 H NMR (400 MHz, CDCl3): δ ppm 1.09 (s, 3H) 1.18 (s, 3H) 1.53 - 1.66 (m, 2H) 1.77 - 1.91 (m, 1H) 2.07 - 2.22 (m, 2H) 2.23 - 2.34 (m, 1H) 2.41 - 2.51 + 2.62 - 2.71 (2xm, 2H) 2.81 (s, 3H) 3.10 - 3.26 (m, 1H) 3.77 - 4.05 (m, 6H) 4.14 - 4.31 + 4.37 - 4.43 (2xm, 3H) 6.81 - 6.92 (2x s, 2H) 7.20 (br d, J = 8.44 Hz, 1H);

[0351] LC-MS (Method A): 549 [M+H], Rt: 1.15 min.

[0352] Example 2: Preparation of 2-[(2,6-difluoro-4-pyridinyl)-(oxetan-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-4, Table 2)

[0353]

[0354] A solution of 2-[(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (0.050 g, 1.0, 0.14 mmol, prepared as described in WO 2019 / 105933) in DMF (1.4 mL) was treated with oxetan-3-carboxylic acid (0.019 g, 1.2, 0.17 mmol), N,N-diisopropylethylamine (0.048 g, 0.064 mL, 0.37 mmol), and HATU (0.082 g, 0.21 mmol). The resulting light brown solution was stirred at RT for 4 h. After this time, the reaction solution was quenched with saturated aqueous sodium bicarbonate and diluted with water. It was then extracted twice with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford a light brown oil. The crude product was purified by reverse phase flash chromatography (eluting with acetonitrile / water) to give the title compound as a beige powder.

[0355] 1 H NMR (400 MHz, CDCl3) δ ppm 0.97 (s, 3H) 1.14 (s, 3H) 1.50 - 1.65 (m, 2H) 1.65 - 1.81 (m, 1H) 2.19 - 2.34 (m, 1H) 2.84 (s, 3H) 3.86 - 4.01 (m, 1H) 4.13 - 4.26 (m, 1H) 4.51 - 4.65 (m, 2H) 4.92 - 5.06 (m, 2H) 6.82 (s, 2H) 6.91 - 7.08 (br s, 1H);

[0356] LC-MS (Method A): 437 [M+H], Rt: 1.05 min.

[0357] Example 3: Preparation of 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-11, Table 2)

[0358] A solution of tetrahydro-2H-pyran-4-carboxylic acid (6.282 g, 46.82 mmol) in acetonitrile (86 mL) was treated with 1-propane phosphonic anhydride (99.32 g, 93.00 mL, 156.1 mmol), and N,N-diisopropylethylamine (40.75 g, 54.6 mL, 10.00, 312.1 mmol) and 2-[(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (11 g, 1.000, 31.21 mmol, prepared as described in WO 2019 / 105933) were added to yield a brown solution. The reaction mixture was stirred at 50 °C under argon for 16 h. After completion of the reaction, the reaction mixture was cooled and slowly added to a saturated aqueous sodium bicarbonate solution at 0 °C. The reaction mixture was then extracted with ethyl acetate (x3), and the combined organic extracts were washed once with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford 15.88 g of a light brown powder. Flash chromatography (eluting with ethyl acetate / cyclohexane) gave the title product as a white powder. 1 H NMR (400 MHz, CDCl3) δ ppm 0.93 (s, 3H) 1.13 (s, 3H) 1.50 - 1.76 (m, 5H) 1.97 - 2.09 (m, 2H) 2.25 (dtd, J = 10.90, 8.08, 8.08, 2.72 Hz, 1H) 2.60 (tt, J = 11.26, 3.81 Hz, 1H) 2.81 (s, 3H) 3.29 (tt, J = 11.90, 1.91 Hz, 2H) 4.01 (dt, J = 11.63, 2.18 Hz, 2H) 4.18 (q, J = 8.60 Hz, 1H) 6.89 (s, 2H) 6.99 (br d, J = 9.08 Hz, 1H)

[0359] LC-MS (Method A): 465 [M+H], Rt: 1.11 min.

[0360] Table 2 below shows exemplary individual compounds of formula (I) according to the present invention.

[0361] Table 2: Melting points and LC / MS data of selected compounds in Table 1 (R t = retention time).

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] Biological Examples:

[0368] Example B1: Alternaria solani / Tomato / Leaf discs (early blight)

[0369] The tomato leaf disc cultivar Baby was placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. Two days after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated in a growth chamber under a 12 / 12 h (light / dark) light regime at 23 °C / 21 °C (day / night) and 80% rh, and the compound activity was evaluated as the percentage of disease control compared to the untreated, when an appropriate level of disease damage appeared on the untreated control leaf discs (5 - 7 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control against Alternaria solani at 200 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0370] Example B2: Botrytis cinerea (Botryotinia fuckeliana, Botrytis cinerea) / Liquid culture (grey mould)

[0371] Fungal conidia from frozen storage were directly mixed into nutrient broth (Vogels broth). After placing the (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 3 - 4 days after application. When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control against Botrytis cinerea at 20 ppm: P-2 and P-4.

[0372] Example B3: Glomerella lagenarium (Colletotrichum orbiculare) / Liquid culture (anthracnose)

[0373] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB - Potato Dextrose Broth). After placing the (DMSO) solution of the test compound in a microtiter plate (96 - well format), nutrient broth containing the fungal spores was added. These test plates were incubated at 24 °C and the inhibition of growth was measured photometrically 3 - 4 days after application. When compared to untreated controls that showed extensive disease development under the same conditions, the following compounds gave at least 80% control of Glomerella cingulata at 20 ppm: P - 1, P - 2, P - 3, P - 4, P - 6, P - 9, P - 10, and P - 11.

[0374] Example B4: Blumeria graminis ( Blumeria graminis f.sp.tritici , Erysiphe graminis f.sp. tritici) / wheat / leaf disc prophylactic (powdery mildew on wheat)

[0375] Wheat leaf segments of cultivar Kanzler were 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 leaf discs were inoculated by shaking powdery - mildew - infected plants over these test plates. In a growth chamber, the inoculated leaf discs were incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness, and the activity of the compound was evaluated as the percentage of disease control compared to untreated when an appropriate level of disease damage appeared on the untreated test leaf segments (6 - 8 days after application). When compared to untreated controls that showed extensive disease development under the same conditions, the following compounds gave at least 80% control of Erysiphe graminis f.sp. tritici at 200 ppm: P - 1, P - 2, P - 3, P - 4, P - 5, P - 6, P - 7, P - 8, P - 9, P - 10, and P - 11.

[0376] Example B5: Phaeosphaeria nodorum ( Phaeosphaeria nodorum , Septoria nodorum) / wheat / leaf disc prophylactic (septoria leaf blotch)

[0377] The wheat leaf segment cultivar Kanzler was placed on agar in a multi-well plate (24-well format) and sprayed with a formulated test compound diluted in water. Two days after application, the leaf discs were inoculated with a spore suspension of the fungus. In a growth chamber, the inoculated test leaf discs were incubated at 20 °C and 75% rh under a 12 h light / 12 h dark lighting regime, and the activity of the compound was evaluated as the percentage of disease control compared to untreated, when an appropriate level of disease damage appeared on the untreated test leaf discs (5 - 7 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Septoria nodorum at 200 ppm: P-2, P-3, and P-10.

[0378] Example B6: Monographella nivalis (Microdochium nivale) / liquid culture (cereal root rot)

[0379] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB - potato dextrose broth). After placing a (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 4 - 5 days after application. When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Cladosporium herbarum at 20 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0380] Example B7: Mycosphaerella arachidicola (Cercospora arachidicola) / liquid culture (early leaf spot)

[0381] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB - potato dextrose broth). After placing a (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 4 - 5 days after application. When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Mycosphaerella arachidicola at 20 ppm: P-1, P-2, and P-10.

[0382] Example B8: Phakopsora pachyrhizi / soybean / preventive (soybean rust)

[0383] Soybean leaf discs were placed on water agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the leaf discs were inoculated by spraying a spore suspension on the lower leaf surface. In a climate chamber, after a 24 - 36 hour incubation period at 20 °C and 75% rh in the dark, the leaf discs were maintained at 20 °C with 12 h light / day and 75% rh. When an appropriate level of disease damage appeared in the untreated control leaf discs (12 - 14 days after application), the activity of the compound was evaluated as the percentage of disease control compared to the untreated. When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Phakopsora pachyrhizi at 200 ppm: P-2, P-3, P-4, P-6, and P-9.

[0384] Example B9: Puccinia recondita f.sp . tritici / Wheat / Leaf disc treatment (Brown rust)

[0385] Wheat leaf segments of the cultivar Kanzler were placed on agar in a multi-well plate (24-well format). These leaf segments were inoculated with a spore suspension of the fungus. The plates were stored in the dark at 19 °C and 75% rh. One day after inoculation, the formulated test compound diluted in water was applied. In an incubator, the leaf segments were incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h dark, and the activity of the compound was evaluated as the percentage of disease control compared to the untreated when an appropriate level of disease damage appeared in the untreated test leaf segments (6 - 8 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Puccinia recondita at 200 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-9, and P-11.

[0386] Example B10: Puccinia recondita / Wheat / Leaf disc prophylaxis (Brown rust)

[0387] The wheat leaf segments of cultivar Kanzler were 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 leaf discs were inoculated with a spore suspension of the fungus. In a growth chamber, the inoculated leaf segments were incubated at 19 °C and 75% rh under a 12 h light / 12 h dark light regime, and the activity of the compound was evaluated as the percentage of disease control compared to the untreated, when an appropriate level of disease damage appeared in the untreated test leaf segments (7 - 9 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-9, P-10, and P-11.

[0388] Example B11: Magnaporthe oryzae (Pyricularia oryzae) / rice / leaf disc prophylaxis (blast)

[0389] The rice leaf segments of cultivar Ballila were placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. Two days after application, the leaf segments were inoculated with a spore suspension of the fungus. In a growth chamber, the inoculated leaf segments were incubated at 22 °C and 80% rh under a light regime of 24 h dark followed by 12 h light / 12 h dark, and the activity of the compound was evaluated as the percentage of disease control compared to the untreated, when an appropriate level of disease damage appeared in the untreated control leaf segments (after 5 - 7 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Magnaporthe oryzae at 200 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, and P-10.

[0390] Example B12: Pyrenophora eres t eres / barley / leaf disc prophylaxis (net blotch)

[0391] The barley leaf segment cultivar Hasso was placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. In a climate chamber, the inoculated leaf segments were incubated at 20 °C and 65% rh under a 12 h light / 12 h dark lighting regime, and the activity of the compound was evaluated as disease control compared to untreated, when an appropriate level of disease damage appeared on the untreated test leaf segments (5 - 7 days after application). When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Pyrenophora teres at 200 ppm: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0392] Example B13: Sclerotinia sclerotiorum / Liquid culture (Cottony rot)

[0393] Mycelial fragments of a fresh growth liquid culture of the fungus were directly incorporated into nutrient broth (PDB (Potato Dextrose Broth)). After placing the (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal material was added. These test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 3 - 4 days after application. When compared to an untreated control showing extensive disease development under the same conditions, the following compound gave at least 80% control of Sclerotinia sclerotiorum at 20 ppm: P-10.

[0394] Example B14: Mycosphaerella graminicola (Septoria tritici) / Liquid culture (Septoria blotch)

[0395] Conidia of the fungus from frozen storage were directly incorporated into nutrient broth (PDB - Potato Dextrose Broth). After placing the (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. These test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 4 - 5 days after application. When compared to an untreated control showing extensive disease development under the same conditions, the following compounds gave at least 80% control of Mycosphaerella graminicola at 20 ppm: P-1, P-2, P-3, P-4, P-9, P-10, and P-11.

Claims

1. A compound having the formula (I): Wherein A is N; R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl; R 2 is fluorine; R 3 is a C1-C3 alkyl group; R 4 、R 7 、R 8 is hydrogen; and R 5 、R 6 is methyl; or a salt thereof.

2. The compound according to claim 1, wherein R 1 is 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

3. The compound according to claim 1 or 2, wherein R 3 is methyl.

4. The compound according to claim 1, wherein the compound is selected from: 2-[(2,6-Difluoro-4-pyridyl)-(tetrahydrofuran-2-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-2); 2-[(2,6-Difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-3); 2-[(2,6-Difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-4); 2-[2-Tert-butoxypropionyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-5); 2-[(2,6-Difluoro-4-pyridyl)-(2-isopropoxypropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-6); 2-[(2-Tert-butoxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-7); 2-[(2,6-Difluoro-4-pyridyl)-(2-isopropoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-8); 2-[(2,6-Difluoro-4-pyridyl)-(2-methoxypropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-9); 2-[(2,6-Difluoro-4-pyridyl)-(2-methylsulfonylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-10); and 2-[(2,6-Difluoro-4-pyridyl)-(tetrahydrofuran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-11).

5. An agrochemical composition comprising a fungicidally effective amount of a compound having the formula (I) according to any one of claims 1 to 4.

6. The composition according to claim 5, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

7. A method for controlling or preventing useful plants from being infected by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound having the formula (I) according to any one of claims 1 to 4 or the composition according to claim 5 or claim 6 is applied to the plants, parts thereof or the places thereof.

8. Use of a compound having the formula (I) according to any one of claims 1 to 4 as a fungicide for non-therapeutic purposes.

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