Thienyl oxazolones and analogs

Abstract

The present disclosure relates to substituted thioenecarboxamide derivatives, their use for controlling phytopathogenic microorganisms and compositions comprising them.

Description

TECHNICAL FIELD

[0001] The present invention relates to substituted thienecarboxamide derivatives, their use for controlling phytopathogenic microorganisms and compositions comprising them. BACKGROUND

[0002] Although many microbicides have been developed to date, there is still a need to develop new microbicidal compounds in order to meet the increasing environmental and economic requirements placed on modern crop protection agents and compositions. This includes, for example, an improved spectrum of action, safety, selectivity, application rate, formation of residues and good manufacturing ability. There can also be a need for new compounds to prevent the emergence of resistance.

[0003] The present invention provides novel compounds which are superior to known compounds and compositions at least in some of these aspects.

[0004] The unpublished application PCT / EP2019 / 067824 discloses thienecarboxamide derivatives for protecting plants against phytopathogenic microorganisms. WO 2004 / 062361 discloses compounds which are said to be effective in the control of fungal diseases. They act by direct action on the undesired microorganisms, but also thanks to an induced resistance effect on the plants. WO 2004 / 062361 also indicates that these compounds can be used for the control of bacterial diseases, but does not provide any evidence of such activity. The inventors of the present invention found that these compounds are less effective at low doses against Xanthomonas campestris pv. campestris. SUMMARY

[0005] The present invention relates to compounds of formula (I) as described herein and isomers, polymorphs, salts, N-oxides and solvates thereof.

[0006] The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable carrier.

[0007] The present invention relates to a process for preparing compounds of formula (I) as described herein and intermediates thereof.

[0008] The present invention relates to a method for controlling phytopathogenic microorganisms, which comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to a plant, a plant part, a seed, a fruit or soil in which a plant grows.

[0009] DEFINITIONS

[0010] As used herein, the term "alkyl" in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino shall be understood to preferably mean branched and straight chain alkyl groups, meaning for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl and decyl and isomers thereof.

[0011] As used herein, the term "alkenyl" shall be understood to preferably mean branched and straight chain alkenyl groups, for example ethenyl, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl or 2-methyl-prop-1-en-1-yl.

[0012] As used herein, the term "alkynyl" shall be understood to preferably mean branched and straight chain alkynyl groups, for example ethynyl, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl or but-3-yn-1-yl.

[0013] As used herein, the term "halogen" or "Hal" shall be understood to mean fluorine, chlorine, bromine or iodine.

[0014] The term "halo" or "halogeno" (e.g. haloalkyl, "Ci-C6-haloalkyl" or "Ci-C8-haloalkyl") denotes optionally substituted by one or more halogen substituents which can be the same or different.

[0015] As used herein, the term "haloalkyl" shall be understood to preferably mean branched and straight chain alkyl groups as defined above, wherein one or more hydrogen substituents are replaced by halogen in the same way or in different ways. Particularly preferred, the haloalkyl is for example chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl and isomers thereof.

[0016] As used herein, the term "haloalkenyl" shall be understood to preferably mean branched and straight chain alkenyl groups as defined above, wherein one or more hydrogen substituents are replaced by halogen in the same way or in different ways.

[0017] As used herein, the term "haloalkynyl" shall be understood to preferably mean branched and straight chain alkynyl groups as defined above, wherein one or more hydrogen substituents are replaced by halogen in the same way or in different ways.

[0018] As used herein, the term "alkoxy" refers to a radical of the formula (alkyl)-O-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkoxy include, but are not limited to methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.

[0019] As used herein, the term "haloalkoxy" refers to an alkoxy group as defined above wherein one or more of the hydrogen atoms is replaced by one or more halogen atoms which can be the same or different.

[0020] As used herein, the term "alkylsulfanyl" refers to a saturated, straight chain or branched group of formula (alkyl)-S-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfanyl include, but are not limited to methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, hexylsulfanyl.

[0021] As used herein, the term "haloalkylsulfanyl" refers to an alkylsulfanyl group as defined above wherein one or more of the hydrogen atoms is replaced by one or more halogen atoms which can be the same or different.

[0022] As used herein, the term "alkylsulfinyl" refers to saturated straight chain or branched alkyl groups of formula (alkyl)-S(=0)-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfinyl include, but are not limited to, saturated straight chain or branched alkylsulfinyl groups having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, such as, but not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl, and 1-ethyl-2-methylpropylsulfinyl.

[0023] As used herein, the term "haloalkylsulfinyl" refers to alkylsulfinyl groups as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which can be the same or different.

[0024] As used herein, the term "alkylsulfonyl" refers to saturated straight chain or branched chain radicals of the formula (alkyl)-S(=0)2-, wherein the term "alkyl" is as defined herein. Examples of C1-C8-alkylsulfonyl include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0025] As used herein, the term "haloalkylsulfonyl" refers to C1-C8-alkylsulfonyl as defined above wherein one or more hydrogen atoms are replaced with one or more halogen atoms which can be the same or different.

[0026] As used herein, the term "alkylcarbonyl" refers to saturated straight chain or branched chain radicals of the formula (alkyl)-C(=0)-, wherein the term "alkyl" is as defined herein.

[0027] As used herein, the term "haloalkylcarbonyl" refers to alkylcarbonyl as defined above wherein one or more hydrogen atoms are replaced with one or more halogen atoms which can be the same or different.

[0028] As used herein, the term "alkoxycarbonyl" refers to saturated straight chain or branched chain radicals of the formula (alkoxy)-C(=0)-, wherein the term "alkoxy" is as defined herein.

[0029] As used herein, the term "haloalkoxycarbonyl" refers to alkoxycarbonyl as defined above wherein one or more hydrogen atoms are replaced with one or more halogen atoms which can be the same or different.

[0030] As used herein, the term "cycloalkyl" refers to non-aromatic monocyclic carbon- containing rings having from 3 to 8 carbon atoms. Examples of saturated cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl.

[0031] As used herein, the term "heterocyclyl" refers to a four-, five-, or six-membered saturated or partially unsaturated ring containing one to four heteroatoms independently selected from oxygen, nitrogen, and sulfur. If the ring contains more than one oxygen atom, they are not directly adjacent.

[0032] As used herein, the term "aryl" refers to an aromatic hydrocarbon ring system comprising 6 to 15 carbon atoms, or 6 to 12 carbon atoms, preferably 6 to 10 carbon atoms. The ring system can be a monocyclic or a fused polycyclic (e.g., bicyclic or tricyclic) aromatic ring system. Examples of aryl groups include, but are not limited to, phenyl, azulenyl, naphthyl, and fluorenyl. It is also understood that when the aryl group is substituted with one or more substituents, the one or more substituents can be at any position on the aromatic ring. In particular, where the aryl group is phenyl, the one or more substituents can occupy one or both of the ortho positions, one or both of the meta positions, or the para position, or any combination of these positions. This definition also applies to aryl groups that are part of a composite substituent (e.g., aryloxy).

[0033] As used herein, the term "aralkyl" refers to a C1-C6-alkyl group substituted with an aryl group as defined herein. Examples of aralkyl groups include benzyl (-CH2-C6H5).

[0034] As used herein, the term "aromatic 5- to 14-membered heterocycle" or "heteroaryl" refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. Aromatic heterocycles include aromatic 5- or 6-membered monocyclic heterocycles and 6- to 14-membered polycyclic (e.g., bicyclic or tricyclic) aromatic heterocycles. The 5- to 14-membered aromatic heterocycle can be attached to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.

[0035] As used herein, for example, in the context of the definition of "C1-C6-alkyl" or "C1-C6-alkoxy", the term "C1-C6" is to be understood as meaning a group with a finite number of carbon atoms of 1 to 6, i.e. 1, 2, 3, 4, 5, or 6 carbon atoms.

[0036] As used herein, for example, in the context of the definition of "C1-C8-alkyl" or "C1-C8-alkoxy", the term "C1-C8" is to be understood as meaning a group with a finite number of carbon atoms of 1 to 8, i.e. 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms.

[0037] As used herein, the term "oxo" refers to an oxygen atom bound to a carbon atom or a sulfur atom through a double bond.

[0038] As used herein, the term "leaving group" is understood to mean a group which is displaced from a compound in a substitution or elimination reaction, for example a halogen atom, a triflate group, an alkoxy group, a mesylate group, a tosylate group, and the like. DETAILED DESCRIPTION

[0039] The present application relates to compounds of formula (I):

[0040]

[0041] wherein

[0042] R 1 , R 2 are independently of each other selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl;

[0043] R 3 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl;

[0044] W, Y are independently of each other selected from oxygen, sulfur;

[0045] R 4 and R 5 are independently of each other selected from hydrogen, Ci-C6-alkyl, aryl-Ci-C6-alkyl or C3-C6-carbocyclyl, wherein the acyclic R 4 , R 5 groups can be substituted by one or more R a substituents, and wherein the cyclic R 4 , R 5 groups can be substituted by one or more R b substituents; or R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclyl or a 3- to 6-membered heterocyclyl, wherein said C3-C6-carbocyclyl and 3- to 6-membered heterocyclyl can be substituted by one or more R b substituents, R a is independently selected from nitro, hydroxy, cyano, carboxyl, amino, sulfanyl, pentafluoro- lambda 6- sulfanyl, formyl, carbamoyl, carbamate, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, Ci-C8-alkylamino, di-Ci-C8-alkylamino, Ci-C8-alkoxy, Ci-C8-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C8-alkylsulfanyl, Ci-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyl, Ci-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbamoyl, di-Ci-C8-alkylcarbamoyl, Ci-C8-alkoxycarbonyl, Ci-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyloxy, Ci-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-C8-alkylcarbonylamino, Ci-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, Ci-C8-alkylsulfinyl, Ci-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonyl, Ci-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonamido, Ci-C8-halogenoalkylsulfonamido having 1 to 5 halogen atoms, sulfamoyl, Ci-C8-alkylsulfamoyl and di-Ci-C8-alkylsulfamoyl, R b independently selected from a halogen atom, a nitro group, a hydroxyl group, a cyano group, a carboxyl group, an amino group, a sulfanyl group, a five-fluoro-λ 6sulfanyl, formyl, carbamoyl, carbamic acid ester, Ci-C8-alkyl, C3-C7-cycloalkyl, Ci-C8-halogenoalkyl having 1 to 5 halogen atoms, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C8-alkylamino, di-Ci-C8-alkylamino, Ci-C8-alkoxy, Ci-C8-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C8-alkylsulfanyl, Ci-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyl, Ci-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbamoyl, di-Ci-C8-alkylcarbamoyl, Ci-C8-alkoxycarbonyl, Ci-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyloxy, Ci-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-C8-alkylcarbonylamino, Ci-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, Ci-C8-alkylsulfanyl, Ci-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfinyl, Ci-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonyl, Ci-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonylamino, Ci-C8-halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, Ci-C8-alkylsulfamoyl and di-Ci-C8-alkylsulfamoyl;

[0046] provided that, if R 1 is halogen and R 2 is halogen, then R 3 is selected from halogen, cyano, Ci-C6-alkyl or Ci-C6-halogenoalkyl.

[0047] provided that, if R 1 and R 2 are identical and both are bromo or chloro, then R 3 is cyano or Ci-C6-halogenoalkyl, or W is sulfur, or R 4 and R 5 do not form, together with the carbon atom to which they are attached, a cyclopropyl group.

[0048] Preferably R 1 is selected from halogen, cyano.

[0049] According to another preferred embodiment, R 2 is halogen.

[0050] Also preferred is R 3If selected from halogen, cyano, C1-C6-alkyl, or C1-C6-haloalkyl, then...

[0051] It is also preferred if the following conditions are met:

[0052] R 1 R 2 They are independently selected from halogen, cyano, C1-C6-alkyl, and C1-C6-haloalkyl;

[0053] R 3 Selected from halogens, cyano groups, C1-C6-alkyl groups, and C1-C6-haloalkyl groups;

[0054] W and Y are independently selected from oxygen and sulfur;

[0055] R 4 and R 5 Each of the components is independently selected from hydrogen, C1-C6-alkyl, aryl-C1-C6-alkyl, or C3-C6-carbon ring, wherein the non-cyclic R 4 R 5 The group can be one or more R a Substituent substitution, and wherein the cyclic R 4 R 5 The group can be one or more R b Substituent substitution; or R 4 and R 5 Together with the carbon atoms they are attached to, they form C3-C6-carbon rings or 3- to 6-membered heterocycles, wherein the C3-C6-carbon rings and 3- to 6-membered heterocycles can be formed by one or more R atoms. b Substituent substitution, R a Independently selected from nitro, hydroxyl, cyano, carboxyl, amino, thioalkyl, and pentafluoro-λ 6 -Thioalkyl, formyl, carbamoyl, carbamate, C 3-C7-cycloalkyl, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylthioalkyl, C1-C8-haloalkylthioalkyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-haloalkoxycarbonyl having 1 to 5 halogen atoms, C 1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-haloalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonylamino, C1-C8-haloalkylsulfonylamino having 1 to 5 halogen atoms, aminosulfonyl, C1-C8-alkylaminosulfonyl and di-C1-C8-alkylaminosulfonyl, R b Independently selected from halogen atoms, nitro groups, hydroxyl groups, cyano groups, carboxyl groups, amino groups, thioalkyl groups, and pentafluoro-λ groups. 6 -Thioalkyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-haloalkyl having 1 to 5 halogen atoms, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylthioalkyl, C1-C8-haloalkyl having 1 to 5 halogen atoms 8-haloalkylsulfanyl, Ci-C8-alkylcarbonyl, Ci-C8-haloalkylcarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbamoyl, di-Ci-C8-alkylcarbamoyl, Ci-C8-alkoxycarbonyl, Ci-C8-haloalkoxycarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyloxy, Ci-C8-haloalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-C8-alkylcarbonylamino, Ci-C8-haloalkylcarbonylamino having 1 to 5 halogen atoms, Ci-C8-alkylsulfanyl, Ci-C8-haloalkylsulfanyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfinyl, Ci-C8-haloalkylsulfinyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonyl, Ci-C8-haloalkylsulfonyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonylamino, Ci-C8-haloalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, Ci-C8-alkylsulfamoyl and di-Ci-C8-alkylsulfamoyl;

[0056] provided that, if R 1 is halogen and R 2 is halogen, then R 3 is selected from halogen, cyano, Ci-C6-alkyl or Ci-C6-haloalkyl.

[0057] provided that, if R 1 and R 2 are identical and both are bromo or chloro, then R 3 is cyano or Ci-C6-haloalkyl, or W is sulfur, or R 4 and R 5 do not form, together with the carbon atom to which they are attached, a cyclopropyl group.

[0058] It is likewise preferred that R 3 is selected from halogen, Ci-C6-alkyl.

[0059] It is also preferred that the compound of formula (I) is selected from 4 and R 5 form, together with the carbon atom to which they are attached, a C3-C6-carbocyclic ring.

[0060] In another preferred embodiment, W is oxygen.

[0061] It is also preferred that the compound of formula (I) is selected from

[0062] In another preferred embodiment

[0063] R 1 is selected from halogen, cyano;

[0064] R 2halogen;

[0065] R 3 selected from halogen, Ci-C6-alkyl;

[0066] R 4 and R 5 form together with the carbon atom to which they are attached a C3-C6-carbocyclic ring;

[0067] W is oxygen;

[0068] Y is oxygen.

[0069] In another preferred embodiment

[0070] R 1 selected from Cl, Br, cyano;

[0071] R 2 is Cl, Br;

[0072] R 3 selected from H, F, Cl, Br, I, CH3;

[0073] R 4 and R 5 form together with the carbon atom to which they are attached a C3-carbocyclic ring;

[0074] W is oxygen;

[0075] Y is oxygen.

[0076] In another embodiment, R 1 is halogen, cyano, Ci-C6-alkyl or Ci-C6-haloalkyl. In another embodiment, R 1 is halogen, cyano, Ci-C3-alkyl or Ci-C3-haloalkyl. In another embodiment, R 1 is halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 1 is halogen. In another embodiment, R 1 is cyano, trifluoromethyl or difluoromethyl.

[0077] In another embodiment, R 2 is halogen, cyano, Ci-C6-alkyl or Ci-C6-haloalkyl. In another embodiment, R 2 is halogen, cyano, Ci-C3-alkyl or Ci-C3-haloalkyl. In another embodiment, R 2 is halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 2 is halogen. In another embodiment, R 2 is cyano, trifluoromethyl or difluoromethyl.

[0078] In another embodiment, R 3 is hydrogen, halogen, cyano, Ci-C6-alkyl or Ci-C6-haloalkyl. In another embodiment, R 3 is hydrogen, halogen, cyano, Ci-C3-alkyl or Ci-C3-haloalkyl. In another embodiment, R 3 is hydrogen, halogen, cyano, methyl, trifluoromethyl or difluoromethyl. In another embodiment, R 3 is halogen. In another embodiment, R 3 is hydrogen. In another embodiment, R 3 is cyano, methyl, trifluoromethyl or difluoromethyl.

[0079] In another embodiment, R 4 and R 5 are independently from each other selected from hydrogen, Ci-C6-alkyl, aryl-Ci-C6-alkyl or C3-C6-carbocyclyl, wherein the acyclic R 4 , R 5 groups can be substituted by one or more R a substituents and wherein the cyclic R 4 , R 5 groups can be substituted by one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclyl or a 3- to 6-membered heterocyclyl, wherein said C3-C6-carbocyclyl and 3- to 6-membered heterocyclyl can be substituted by one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclyl, wherein said C3-C6-carbocyclyl can be substituted by one or more R b substituents. In another embodiment, R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl, wherein said cyclopropyl or cyclobutyl can be substituted by one or more R b substituents.

[0080] In another embodiment, W is oxygen. In another embodiment, W is sulfur. In another embodiment, Y is oxygen. In another embodiment, Y is sulfur.

[0081] Also preferred are compounds I.01 to I.26 disclosed in the experimental part.

[0082] Compounds resulting from combinations which violate the laws of nature and are therefore excluded by the person skilled in the art on the basis of his / her expert knowledge are not included herein. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[0083] Depending on the nature of the substituents, the compounds of the formula (I) can exist in different stereoisomeric forms. These stereoisomeric forms are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present application therefore includes pure stereoisomers and any mixture of these isomers. Where a compound can exist in two or more tautomeric forms, a reference to the compound shall be construed as a reference to each of those tautomers in equilibrium with each other.

[0084] Depending on the number of double bonds in the compounds, any of the compounds of the present application can also exist in one or more geometric isomeric forms. The geometric isomers can exist in the cis (= Z-) or trans (= E-) form depending on the nature of the substituents of the double bond or the ring. The present application therefore likewise relates to all geometric isomers and all possible mixtures thereof in all proportions.

[0085] The compounds of the formula (I) can suitably be in the form of their free forms, salt forms, N-oxide forms or solvate forms (e.g. hydrates).

[0086] Depending on the nature of the substituents, the compounds of the formula (I) can exist in the form of the free compounds and / or their salts (e.g. agrochemically active salts).

[0087] Agrochemically active salts include acid addition salts of inorganic acids and organic acids and salts of customary bases. Examples of inorganic acids are hydrohalic acids (e.g. hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide), sulfuric acid, phosphoric acid and nitric acid, and acid salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include formic acid, carbonic acid and alkanoic acids (e.g. acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid), and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated aliphatic or mono- or diunsaturated aliphatic acids having 6 to 20 carbon atoms, alkylsulfuric monoesters, alkylsulfonic acids (sulfonic acids having straight-chain or branched-chain alkyl radicals with 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulfonic acid radicals), alkylphosphonic acids (phosphonic acids having straight-chain or branched-chain alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic acid radicals), where the alkyl and aryl radicals can also carry further substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and the like.

[0088] The solvate of the compound of formula (I) or a salt thereof is a stoichiometric composition of a compound and a solvent.

[0089] The compounds of formula (I) can exist in various crystalline and / or amorphous forms. The crystalline forms include unsolvated crystalline forms, solvates and hydrates.

[0090] The present application also relates to any of the compounds of formula (I) disclosed in Table 1 and their use in crop protection (i.e. for controlling phytopathogenic fungi and / or bacteria on plants or plant parts).

[0091] Another aspect of the present application relates to a composition comprising at least one compound of formula (I) of the present application and at least one agriculturally suitable auxiliary.

[0092] Another aspect of the present application relates to a method of controlling a bacterial and / or fungal disease, which comprises the step of applying at least one compound of formula (I) of the present application or a composition of the present application to a plant, a plant part, a seed, a fruit or a soil in which a plant is growing.

[0093] Another aspect of the present application relates to the use of a compound of the present application or a composition of the present application for controlling a bacterial and / or fungal disease on a plant or plant part. Preferably it is used for controlling a fungal disease on a plant or plant part.

[0094] Another aspect of the present application relates to the use of a compound of the present application or a composition of the present application for controlling a nematode on a plant or plant part.

[0095] Another aspect of the present application relates to the use of a compound of the present application or a composition of the present application for controlling a virus on a plant or plant part.

[0096] It is preferred that the compounds or compositions of the application are used to combat: diseases caused by an Erysiphe pathogen, for example Podosphaera species (for example Podosphaera leucotricha), Sphaerotheca species (for example Sphaerotheca fuliginea); diseases caused by a rust pathogen, for example Uromyces species (for example Uromyces appendiculatus); diseases caused by a pathogen selected from Oomycetes, for example Peronospora species (for example Peronospora parasitica), Phytophthora species (for example Phytophthora infestans), Plasmopara species (for example Plasmopara viticola), Pseudoperonospora species (for example Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (for example Pythium ultimum); leaf blotch diseases and leaf wilt diseases, for example caused by Alternaria species (for example Alternaria solani), Cercospora species (for example Cercospora beticola), Colletotrichum species (for example Colletotrichum lindemuthanium), Venturia species (for example Venturia inaequalis); diseases caused by a bacterial pathogen, for example Xanthomonas species (for example Xanthomonas campestris pv.Erwinia species (e.g., Erwinia amylovora), Liberibacter species (e.g., Liberibacter Candidatus), Ralstonia species (e.g., Ralstonia solanacearum).

[0097] According to another aspect of the present application, the compounds or compositions of the present application are used as plant defense activators. The plant defense inducers of the present application are compounds or compositions that stimulate a plant's own defense system.

[0098] Process for the preparation of compounds of formula (I)

[0099] The present application relates to a process for preparing a compound of formula (I). The compound of formula (I) can be prepared by various routes, analogously to known methods described in Helvetica Chimica Acta, 69(2), 374-388, 1986; Helvetica Chimica Acta, 70(4), 1001-1011, 1987; Chimia, 36(2), 78-81, 1982; Helvetica Chimica Acta, 71(8), 2071-2084, 1988; Heterocyclic Communications, 9(2), 129-134; 2003; WO2007080885; WO2007003536; Chemical Communications (Cambridge, United Kingdom), 55(39), 5547-5550; 2019; and other references therein, or by one or more of the synthetic routes described herein below and in the experimental section.

[0100] General synthetic route for compounds of formula (I)

[0101] In the following, R 1 , R 2 , R 3 , R 4 , R 5 , W, Y have the same meaning as given above for Compounds of formula (I) .

[0102] Method A

[0103] The compounds of formula (I) as defined herein can be prepared by Method A from a compound of formula (IIa) (wherein R 6 is hydrogen) or one of its salts by a cyclization reaction, as shown in the following reaction scheme:

[0104]

[0105] Method A can be performed as described in Journal of Heterocyclic Chemistry, 25(1), 209-215; 1988; WO2007003536.

[0106] Method A can be performed in the presence of a suitable Bronsted acid, Lewis acid or other condensing agent, if appropriate in the presence of a suitable acid binder, and if appropriate in the presence of a solvent.

[0107] Suitable Lewis acids for performing Method A can be inorganic and organic Lewis acids which are typically used for such reactions. Preference is given to using metal halides, such as aluminium (III) chloride, iron (III) chloride, zinc (II) chloride, titanium tetrachloride, boron trifluoride; triflates, such as scandium (III) trifluoromethanesulphonate, bismuth (III) trifluoromethanesulphonate or ytterbium (III) trifluoromethanesulphonate, and iodine.

[0108] Suitable Bronsted acids for performing Method A can be inorganic and organic Bronsted acids which are typically used for such reactions. Preference is given to using hydrogen halides, such as hydrogen chloride or hydrogen bromide; sulfonic acids, such as p-toluenesulfonic acid, camphorsulfonic acid, methanesulfonic acid or trifluoromethanesulfonic acid, and polyphosphoric acid, phosphoric acid sulfuric acid, potassium bisulfite, trifluoroacetic acid or acetic acid.

[0109] ​Other suitable condensing agents for carrying out process A can be selected from the non- limiting list consisting of acyl halide forming agents such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride; acid anhydride forming agents such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methylsulfonyl chloride; acid anhydrides such as trifluoroacetic anhydride or acetic anhydride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) or other conventional condensing agents such as phosphorous pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphonium chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphonium chloride (BOP-Cl), bromo-tripyrrolidinophosphonium hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC) or propane phosphonic anhydride (T3P).

[0110] Suitable acid binding agents for carrying out process A of the present application are in each case all inorganic and organic bases which are customary for such reactions. Preference is given to alkali metal carbonates such as cesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate; and tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N-methylpiperidine, N,N-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), or aromatic bases such as pyridine.

[0111] Suitable solvents for carrying out process A are not particularly limited. They can be the usual inert organic solvents, provided that it does not dissolve the compound with which it is reacted or exhibit any particular interaction with the compound. It is preferred to use optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR TM E or ISOPAR TM G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoamide; ureas, such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; or sulphones, such as sulfolane; and mixtures thereof.

[0112] Process A can be carried out under an inert atmosphere. When carrying out process A, 0.01 to 5 mol-% of suitable acid or condensing agent per mole of compound of formula (IIa) and 0.01 to 5 mol of acid binding agent per mole of compound of formula (IIa) can be used. Other ratios of the reaction components can also be used. The work-up is carried out by known methods.

[0113] Compounds of formula (IIa) wherein R 6 represents hydrogen can be prepared from compounds of formula (IIb) wherein R 6 represents Ci-C6-alkyl by well-known methods, such as hydrolysis. Examples of hydrolysis reagents include lithium hydroxide, potassium hydroxide, sodium hydroxide, trimethyltin hydroxide. Hydrolysis can be carried out as described in WO2008157844; WO2006002099; WO20050256107; Angewandte Chemie, International Edition (2005), 44(9), 1378-1382.

[0114] Method B

[0115] Compounds of formula (IIc) wherein R 6representing hydrogen or Ci-C6-alkyl) can be prepared by a process B comprising the step of reacting a compound of formula (III) or one of its salts with a compound of formula (IV) or one of its salts as illustrated in the following reaction scheme:

[0116]

[0117] wherein U 1 represents halogen, hydroxyl or Ci-C6-alkoxy.

[0118] When U 1 represents hydroxyl, process B is advantageously carried out in the presence of a condensing agent. Suitable condensing agents can be selected from the non-limiting list consisting of acyl halide forming agents such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride; acid anhydride forming agents such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) or other conventional condensing agents such as phosphorous pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), tripyrrolidinylphosphonium bromide hexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), propane phosphonic acid anhydride (T3P) and 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT).

[0119] When U 1When representing halogen, process B is advantageously carried out in the presence of an acid-binding agent. Suitable acid-binding agents for carrying out process B are in each case all inorganic and organic bases which are customary for such reactions. Preference is given to alkali metal carbonates, such as cesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate; and tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N-methylpiperidine, N,N-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), or aromatic bases, such as pyridine.

[0120] When U 1 When representing Ci-C6-alkoxy, process B can be carried out in excess of the amine component, optionally in the presence of a Lewis acid, such as trimethylaluminium.

[0121] If appropriate, process B can be carried out in the presence of a base, and, if appropriate, in the presence of a solvent, preferably under anhydrous conditions.

[0122] Suitable solvents for carrying out process B are not particularly limited. They can be the usual inert organic solvents, provided that it does not dissolve the compounds with which it is reacted or exhibit any particular interaction with the compounds. Preference is given to using optionally halogenated aliphatic, cycloaliphatic or aromatic hydrocarbons, such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR TM E or ISOPAR TM G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; ureas, such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; or sulphones, such as sulfolane; and mixtures thereof.

[0123] Process B can be carried out under an inert gas atmosphere, such as an argon or nitrogen atmosphere. When carrying out process B, 1 mole or an excess of the compound of the formula (IV) and 1 to 5 moles of base can be used per mole of the compound of the formula (III). Other ratios of the reaction components can also be used. The work-up is carried out by known methods.

[0124] Compounds of formula (IV) are commercially available or can be prepared by well-known methods.

[0125] Compounds of formula (Ilia) wherein U 1 represents hydroxy are commercially available, can be prepared from compounds of formula (Illb) wherein U 1 represents C1-C6-alkoxy by well-known methods (e.g. basic hydrolysis) or can be prepared by known methods (Beilstein J. Org. Chem. 2007, 3, No. 23).

[0126] Compounds of formula (IIIc) wherein U 1 represents halogen are commercially available or can be prepared from compounds of formula (Ilia) wherein U 1 represents hydroxy by well-known methods.

[0127] Compounds of formula (Illb) wherein U 1 represents C1-C6-alkoxy can be prepared from compounds of formula (Ilia) wherein U 1 represents hydroxy by well-known methods.

[0128] Method C

[0129] Compounds of formula (lid) wherein R 6 represents hydrogen or C1-C6-alkyl can be prepared from compounds of formula (lie) wherein R 6 represents hydrogen or C1-C6-alkyl by performing a thiation reaction as shown in the following reaction scheme:

[0130]

[0131] Method C of the present application is performed in the presence of a thiating agent.

[0132] Suitable sulfurizing agents for carrying out process C of the present application can be sulfur (S), sulfhydric acid (H2S), sodium sulfide (Na2S), sodium hydrosulfide (NaHS), boron trisulfide (B2S3), bis(diethylaluminum) sulfide ((AlEt2)2S), ammonium sulfide ((NH4)2S), diphosphorus pentasulfide (P2S5), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer-supported sulfurizing reagent as described in Journal of the Chemical Society, Perkin 1 (2001 ), 358, optionally in the presence of catalytic amounts or stoichiometric amounts or an excess of a base, for example an inorganic base and an organic base. The use of alkali metal carbonates, for example sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; heterocyclic aromatic bases, for example pyridine, picoline, lutidine, collidine; and tertiary amines, for example trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine, is preferred.

[0133] Suitable solvents for carrying out process C of the present application can be conventional inert organic solvents. The use of optionally halogenated aliphatic, cycloaliphatic or aromatic hydrocarbons, for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, for example diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; nitriles, for example acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; sulfur-containing solvents, for example sulfolane or carbon disulfide, is preferred.

[0134] When carrying out process C of the present application, 1 mol or an excess of sulfur equivalent of the sulfurizing agent and 1 to 3 mol of base per mol of amide reactant (lie) can be used.

[0135] Other ratios of the reaction components can also be used. The work-up is carried out by known methods.

[0136] Intermediates for the preparation of compounds of formula (I)

[0137] The present application relates to intermediates for the preparation of compounds of formula (I)

[0138] A compound of formula (II) is provided:

[0139]

[0140] wherein

[0141] R 1 , R 2 are independently from each other selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl;

[0142] R 3 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl;

[0143] W is independently selected from oxygen, sulfur;

[0144] R 4 and R 5 are independently from each other selected from hydrogen, Ci-C6-alkyl, aryl-Ci-C6-alkyl or C3-C6-carbocyclyl, wherein acyclic R 4 , R 5 groups can be substituted with one or more R a substituents and wherein cyclic R 4 , R 5 groups can be substituted with one or more R b substituents; or R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-carbocyclyl or a 3- to 6-membered heterocyclyl, wherein said C3-C6-carbocyclyl and 3- to 6-membered heterocyclyl can be substituted with one or more R b substituents, R a is independently selected from nitro, hydroxy, cyano, carboxy, amino, sulfanyl, pentafluoro- lambda. 6- sulfanyl, formyl, carbamoyl, carbamate, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, Ci-C8-alkylamino, di-Ci-C8-alkylamino, Ci-C8-alkoxy, Ci-C8-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C8-alkylsulfanyl, Ci-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyl, Ci-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbamoyl, di-Ci-C8- alkylcarbamoyl, Ci-C8-alkoxycarbonyl, Ci-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-C8-alkylcarbonyloxy, Ci-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-C8-alkylcarbonylamino, Ci-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, Ci-C8-alkylsulfinyl, Ci-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonyl, Ci-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-C8-alkylsulfonylamino, Ci-C8-halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, Ci-C8-alkylsulfamoyl and di-Ci-C8-alkylsulfamoyl, R b independently selected from a halogen atom, a nitro group, a hydroxyl group, a cyano group, a carboxyl group, an amino group, a sulfanyl group, a pentafluoro-λ 6sulfonyl, C1-C8-alkylsulfonyl, C1-C8-halogenated alkylsulfonyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonylamino, C1-C8-halogenated alkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl;

[0145] R 6 is selected from hydrogen, C1-C6-alkyl;

[0146] with the proviso that, if R 1 is halogen and R 2 is halogen, then R 3 is selected from halogen, cyano, C1-C6-alkyl or C1-C6-halogenated alkyl.

[0147] with the proviso that, if R 1 and R 2 are identical and both are bromo or chloro, then R 3 is cyano or C1-C6-halogenated alkyl, or W is sulfur, or R 4 and R 5 do not form, together with the carbon atom to which they are attached, a cyclopropyl group.

[0148] Compositions and formulations

[0149] The present application also relates to a composition, in particular a composition for controlling unwanted microorganisms, comprising one or more compounds of formula (I). The composition is preferably a fungicide composition.

[0150] The composition generally comprises one or more compounds of formula (I) and one or more acceptable carriers, in particular one or more agriculturally acceptable carriers.

[0151] The carrier is generally an inert, solid or liquid, natural or synthetic, organic or inorganic substance. The carrier generally improves the application of the compound, for example to plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock powders (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth) and synthetic rock powders (e.g., finely divided silica, alumina, and silicates). Examples of useful solid carriers that are typically used in the preparation of granular formulations include, but are not limited to, pulverized and fractionated natural rocks (e.g., calcite, marble, pumice, meerschaum, and dolomite), synthetic granules of mineral and organic material, and granules of organic materials (e.g., paper, sawdust, coconut shells, corn cobs, and tobacco stalks). Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, for example from the following classes: aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, paraffins, alkylbenzenes, xylene, toluene, alkyl naphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethene, or dichloromethane), alcohols and polyols (which can also optionally be substituted, etherified and / or esterified, for example butanol or ethylene glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (e.g., dimethylformamide), lactams (e.g., N-alkylpyrrolidones), and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide). The carrier can also be a liquefied gaseous extender, i.e., a liquid at standard temperature and pressure, which is gaseous, for example an aerosol propellant, such as a halogenated hydrocarbon, butane, propane, nitrogen, and carbon dioxide. The amount of carrier is generally 1 to 99.99% by weight, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight, and most preferably 20 to 99% by weight, of the composition.

[0152] The composition can also comprise one or more acceptable adjuvants that are typically used in formulating compositions, for example agrochemical compositions, such as one or more surfactants.

[0153] The surfactants can be ionic (cationic or anionic) or non-ionic surfactants, such as ionic or non-ionic emulsifiers, foam formers, dispersants, wetting agents, and any mixture thereof. Examples of suitable surfactants include, but are not limited to, polyacrylic acid salts, lignosulfonates, phenolsulfonates or naphthalenesulfonates, polycondensates of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulfate, sulfonate, phosphate radicals (such as alkyl sulfonates, alkyl sulfates, aryl sulfonates), as well as protein hydrolysates, lignosulfite waste liquors and methylcellulose. When the compounds of formula (I) and / or the carrier are not water-soluble and are to be applied with water, surfactants are generally used. The amount of surfactant is then typically 5 to 40% by weight of the composition.

[0154] Further examples of adjuvants commonly used for formulating agrochemical compositions include water repellents, drying agents, binders (adhesives, tackifiers, fixatives, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices (for example polyvinyl alcohol and polyvinyl acetate), natural phospholipids (for example cephalins and lecithins) and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tyloses), thickeners, stabilizers (for example cold-soluble stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability), dyes or pigments (for example inorganic pigments, such as iron oxide, titanium oxide and Prussian Blue; organic dyes, such as alizarin, azo and metal phthalocyanine dyes), antifoams (for example silicone antifoams and magnesium stearate), preservatives (for example dichlorophen and benzyl alcohol hemiformal), secondary thickeners (cellulose derivatives, acrylate derivatives, xanthan gum, modified clays and finely divided silicas), stickers, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients, such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts), protective colloids, thixotropic substances, penetrants, sequestering and complexing agents.

[0155] The choice of adjuvant is dependent on the intended mode of application and / or the physical properties of the compound of formula (I). Furthermore, the adjuvant can be chosen to impart particular properties (technical, physical and / or biological properties) to the composition or to the form of use prepared therefrom. The choice of adjuvant can allow the composition to be tailored to the particular requirements.

[0156] The compositions can be in any conventional form, for example solutions (for example aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, dusts, powders, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the compounds of the present application, fertilizers and polymers in which microcapsules are included. The compounds of formula (I) can be present in suspended, emulsified or dissolved form.

[0157] The compositions can be provided to the end user as ready-to-use formulations, i.e. the compositions can be applied directly to the plant or seed by suitable means, for example by spraying or dusting devices. Alternatively, the compositions can be provided to the end user in the form of concentrates which have to be diluted before use, preferably with water.

[0158] The compositions can be prepared in a conventional manner, for example by mixing the compounds of formula (I) with one or more suitable auxiliaries, for example as disclosed hereinbefore.

[0159] The compositions generally contain from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight, of the compound of formula (I).

[0160] The compounds and compositions comprising them can be mixed with other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners or semiochemicals. This can broaden the activity spectrum or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in The Pesticide Manual, 17th Edition.

[0161] The active ingredients specified herein by their common names are known and are described, for example, in The Pesticide Manual, 16th Edition, British Crop Protection Council, or can be retrieved on the internet (for example www.alanwood.net / pesticides).

[0162] In cases where the compounds (A) or (B) can exist in tautomeric forms, the compounds are understood in the above and below herein, where applicable, to also include the corresponding tautomeric forms, even if not specifically mentioned in each case.

[0163] Examples of fungicides with which the compounds of formula (I) and the compositions of the present application can be mixed are:

[0164] 1) Ergosterol biosynthesis inhibitors, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, and (1.011) imazalil sulfate. (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridmorph, (1.025) tebuconazole riticonazole), (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028)(2R)-2-(1-chlorocyclopropyl)-4-[( 1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)but-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)prop-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1- yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4- triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1- yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3- yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3- yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3- yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2- yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2- yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1H-1,2,4-triazol-5- yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1H-1,2,4- triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1H-1,2,4- triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-1,2,4-triazole-3-thione, (1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.051) 2-[2-chloro-4-(2,4- dichlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiranyl-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-2,4- dihydro-3H-1,2,4-triazol-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1 H-1,2,4-triazol-1- ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl))-2-(2,4- difluorophenyl)oxiranyl-2-yl]methyl}-1 H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1 H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1 H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidocarbamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2- trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidocarbamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidocarbamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidocarbamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N- ethyl-N-methylimidocarbamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2- trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidocarbamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N- ethyl-N-methylimidocarbamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidocarbamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidocarbamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl)]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N- methylimidocarbamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5- dimethylphenyl)-N-ethyl-N-methylimidocarbamide, (1.074)N'-[5-bromo-6-(2,3-dihydro-1 H-inden-2-yloxy)-2-methylpyridin-3-yl]-N- ethyl-N-methylimidocarbamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5- dimethylphenyl}-N-ethyl-N-methylimidocarbamide, (1.076) N'-{5-bromo-6-[(1 R)-1 -(3,5- difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (1.077) N'-{5-bromo-6-[(1 S)-1 -(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N- ethyl-N-methylimidocarbamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]- 2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (1.079) N'-{5-bromo-6-[(trans-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (1.080) N'-{5-bromo-6-[1 -(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N- ethyl-N-methylimidocarbamide, (1.081 ) ipfentrifluconazole, (1.082) 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1 - yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 - (1,2,4-triazol-1 -yl)propan-2-ol, (1.085) 3-[2-(1 -chlorocyclopropyl)-3-(3-chloro-2- fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[rac-(2R)-2- (2,4-difluorophenyl)-1,1 -difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1 -yl)propyl]- 3-pyridyl]oxy]benzonitrile, (1.087) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2- trifluoro-1 -hydroxy-1 -phenylethyl)phenyl]-N-methylimidocarbamide, (1.088) N'-{5-bromo- 2-methyl-6-[(1 -propyloxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (1.089) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 H-1,2,4- triazol-1 -yl)propanoate.

[0165] 2) inhibitors of the respiratory chain at complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam (trans epimer 1 R, 4S, 9S), (2.011) isopyrazam (trans epimer 1 S, 4R, 9R), (2.012) isopyrazam (trans racemate 1 RS, 4SR, 9SR), (2.013) isopyrazam (mixture of the cis epimer 1 RS, 4SR, 9RS and the trans epimer 1 RS, 4SR, 9SR), (2.014) isopyrazam (cis epimer 1 R, 4S, 9R), (2.015) isopyrazam (cis epimer 1 S, 4R, 9S), (2.016) isopyrazam (cis racemate 1 RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4- carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H- pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4- yl]-1 H-pyrazole-4-carboxamide, (2.025) 1 -methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)- biphenyl-2-yl]-1 H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3- trimethyl-2,3-dihydro-1 H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1 -methyl-N-(1,1,3- trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1 - methyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2.029) 3-028)inpyrfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4- amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylidene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylidene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-N-[5-methyl-2- (trifluoromethyl)benzyl]-lH-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l-methyl-lH-pyrazole-4- carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5- methylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazole-4- thio-carboxamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2- isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l-methyl-lH-pyrazole-4- carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5- dimethylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.052) N- cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5- methylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.054) N-cyclopropyl- N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole- 4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.056) N- cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (2.057) pyrapropoyne, (2.058) N-[rac-(lS,2S)-2-(2,4- dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(lS,2S)-2-(2,4- dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.060) flubeneteram.

[0166] 3) Inhibitors of respiratory chain complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, and (3.009) famoxa. (3.010) Fenamidone, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametos (3.019) trobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5- (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-carbamate-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029){5-[3-(2,4-dimethylphenyl)-1 H-pyrazol-1 -yl]-2-methylbenzyl}methy lam inocarbamate, (3.030) metyltetraprole, (3.031 ) floryl picoxamid.

[0167] 4) Inhibitors of mitosis and cell division, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.009) pyridachlometyl, (4.001) carbendazim, (4.002) diethofencarb, (4.003) thiophanate-methyl, (4.004) zoxamide, (4.005) pyridachlometyl, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.001) thiophanate-methyl, (4.002) thiophanate-methyl, (4.003) thiophanate-methyl, (4.004) zoxamide, (4.005) pyridachlometyl, (4.006) thiabendazim, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.001) thiophanate-methyl, (4.002) thiophanate-methyl, (4.003) thiophanate-methyl, (4.004) zoxamide, (4.005) pyridachlometyl, (4.006) thiophanate-methyl, (4.007) thiophanate-methyl, (4.00 0.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.015) 4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole- 5-Amine, (4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl- 1 H-pyrazol-5-amine, (4.026) fluopimomide.

[0168] 5) Compounds capable to have a multisite action, for example (5.001 ) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011 ) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021 ) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3- c][1,2]thiazole-3-carbonitrile.

[0169] 6) Compounds capable to induce a host defense, for example (6.001 ) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[0170] 7) Inhibitors of the amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline.

[0171] 8) Inhibitors of the ATP production, for example (8.001) silthiofam.

[0172] 9) Inhibitors of the cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert.-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (9.009) (2Z)-3-(4-tert.-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one.

[0173] 10) Inhibitors of the lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0174] 11) Inhibitors of the melanin biosynthesis, for example (11.001) tricyclazole, (11.002) tolprocarb.

[0175] 12) Inhibitors of the nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0176] 13) signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[0177] 14) compounds capable to act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.

[0178] 15) Other fungicides selected from (15.001) abscisic acid, (15.002) bethoxazin, (15.003) capsimycin, (15.004) carvone, (15.005) chinomethionat, (15.006) cufraneb, (15.007) cyflufenamid, (15.009) cymoxanil, and (15.010) cyprofenamide. (15.011) flutianil, (15.012) fosetyl-aluminum, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin (15.019) Nickel dimethyl dithiocarbamate, (15.020) Nitrothal-isopropyl, (15.021) Oxamocarb, (15.022) Oxatispiprolin, (15.023) Oxyfenthiin, (15.024) Pentachlorophenol and its salts, (15.025) Phosphorous acid and its salts, (15.026) Propamocarb-fosetylate, (15.027) Phenypicyl-methyl ( pyriofenone)(chlazafenone, (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazolyl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] acetone, (15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033)2-(6-benzylpyridin-2-yl)quinazoline, (15.034)dipymetitrone, (15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)ipflufenoquin, (15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043)fluoxapiprolin, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045)2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047)quinofumelin, (15.048)4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-l,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-l-yl)thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-l,4-benzoxazepine, (15.055) but-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5-yl)(phenyl)methyl]amino}oxy)methyl]pyridin-2- yl}carbamate, (15.056) (2Z)-3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.057) phenazin-1-carboxylic acid, (15.058) 3,4,5-trihydroxybenzoic acid propyl ester, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2: 1), (15.061) {6-[({[(l-methyl-lH-tetrazol-5-yl)(phenyl)methyl]amino}oxy)methyl]pyridin-2-yl}carbamic acid tert-butyl ester, (15.062) 5-fluoro-4-imino-3-methyl-l-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(lH)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidocarbamide), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidocarbamide), (15.066) (2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-l-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069) (l-(4,5-dimethyl-lH-benzoimidazol-l-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinolone, (15.071)8-Fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinolone, (15.072) 3-(4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)-8-fluoroquinoline, (15.073) (N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide), (15.074) Methyl {4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.075) (N-{4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15.076) N-Methyl-4-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.077) N-[(E)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.078) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.080) N-(2-Fluorophenyl)-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.082) N-Allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, (15.083) N-[(E)-N-Methoxy-C-methyl-carbonimidoyl]-4-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.085) N-Allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.086) 4,4-Dimethyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-Methyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]thiobenzamide, (15.088) 5-Methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089)N-((2,3-Difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propionamide, (15.090)1-Methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091)1,1-Diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092)N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.093)N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094)1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095)N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096)N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.097)N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propionamide, (15.098)1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099)1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100)3-Ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101)1-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102)4,4-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.103)5,5-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104)3,3-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105)1-[[3-Fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butyramide, (15.111) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyldimethylcarbamic acid ester, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propionamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonic acid ester, (15.120) 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonic acid ester, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonic acid ester, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3- thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3- carboxamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3- carboxamide, (15.126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, and (15.127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide.

[0179] If the functional groups of all named mixing partners of classes (1) to (15) are capable of forming salts with a suitable base or acid, they can optionally form salts with a suitable base or acid.

[0180] Another aspect of the application relates to one or more of the following compounds in combination:

[0181] (I.01) + (1.01), (I.01) + (1.02), (I.01) + (1.03), (I.01) + (1.04), (I.01) + (1.05), (I.01) + (1.06), (I.01) + (1.07), (I.01) + (1.08), (I.01) + (1.09), (I.01) + (1.10), (I.01) + (1.11), (I.01) + (1.12), (I.01) + (1.13), (I.01) + (1.14), (I.01) + (1.15), (I.01) + (1.16), (I.01) + (1.17), (I.01) + (1.18), (I.01) + (1.19), (I.01) + (1.20), (I.01) + (1.21), (I.01) + (1.22), (I.01) + (1.23), (I.01) + (1.24), (I.01) + (1.25), (I.01) + (1.26), (I.01) + (1.27), (I.01) + (1.28), (I.01) + (1.29), (I.01) + (1.30), (I.01) + (1.31), (I.01) + (1.32), (I.01) + (1.33), (I.01) + (1.34), (I.01) + (1.35), (I.01) + (1.36), (I.01) + (1.37), (I.01) + (1.38), (I.01) + (1.39), (I.01) + (1.40), (I.01) + (1.41), (I.01) + (1.42), (I.01) + (1.43), (I.01) + (1.44), (I.01) + (1.45), (I.01) + (1.46), (I.01) + (1.47), (I.01) + (1.48), (I.01) + (1.49), (I.01) + (1.50), (I.01) + (1.51), (I.01) + (1.52), (I.01) + (1.53), (I.01) + (1.54), (I.01) + (1.55), (I.01) + (1.56), (I.01) + (1.57), (I.01) + (1.58), (I.01) + (1.59), (I.01) + (1.60), (I.01) + (1.61), (I.01) + (1.62), (I.01) + (1.63), (I.01) + (1.64), (I.01) + (1.65), (I.01) + (1.66), (I.01) + (1.67), (I.01) + (1.68), (I.01) + (1.69), (I.01) + (1.70), (I.01) + (1.71), (I.01) + (1.72), (I.01) + (1.73), (I.01) + (1.74), (I.01) + (1.75), (I.01) + (1.76), (I.01) + (1.77), (I.01) + (1.78), (I.01) + (1.79), (I.01) + (1.80), (I.01) + (1.81), (I.01) + (1.82), (I.01) + (1.83), (I.01) + (1.84), (I.01) + (1.85), (I.01) + (1.86), (I.01) + (1.87), (I.01) + (1.88), (I.01) + (1.89), (I.01) + (1.90), (I.01) + (1.91), (I.01) + (1.92), (I.01) + (1.93), (I.01) + (1.94), (I.01) + (1.95), (I.01) + (1.96), (I.01) + (1.97), (I.01) + (1.98), (I.01) + (1.99), (I.01) + (1.100).067), (I.01) + (1.068), (I.01) + (1.069), (I.01) + (1.070), (I.01) + (1.071), (I.01) + (1.072), (I.01) + (1.073), (I.01) + (1.074), (I.01) + (1.075), (I.01) + (1.076), (I.01) + (1.077), (I.01) + (1.078), (I.01) + (1.079), (I.01) + (1.080), (I.01) + (1.081), (I.01) + (1.082), (I.01) + (1.083), (I.01) + (1.084), (I.01) + (1.085), (I.01) + (1.086), (I.01) + (1.087), (I.01) + (1.088), (I.01) + (1.089), (I.01) + (2.001), (I.01) + (2.002), (I.01) + (2.003), (I.01) + (2.004), (I.01) + (2.005), (I.01) + (2.006), (I.01) + (2.007), (I.01) + (2.008), (I.01) + (2.009), (I.01) + (2.010), (I.01) + (2.011), (I.01) + (2.012), (I.01) + (2.013), (I.01) + (2.014), (I.01) + (2.015), (I.01) + (2.016), (I.01) + (2.017), (I.01) + (2.018), (I.01) + (2.019), (I.01) + (2.020), (I.01) + (2.021), (I.01) + (2.022), (I.01) + (2.023), (I.01) + (2.024), (I.01) + (2.025), (I.01) + (2.026), (I.01) + (2.027), (I.01) + (2.028), (I.01) + (2.029), (I.01) + (2.030), (I.01) + (2.031), (I.01) + (2.032), (I.01) + (2.033), (I.01) + (2.034), (I.01) + (2.035), (I.01) + (2.036), (I.01) + (2.037), (I.01) + (2.038), (I.01) + (2.039), (I.01) + (2.040), (I.01) + (2.041), (I.01) + (2.042), (I.01) + (2.043), (I.01) + (2.044), (I.(I.01) + (2.045), (I.01) + (2.046), (I.01) + (2.047), (I.01) + (2.048), (I.01) + (2.049), (I.01) + (2.050), (I.01) + (2.051), (I.01) + (2.052), (I.01) + (2.053), (I.01) + (2.054), (I.01) + (2.055), (I.01) + (2.056), (I.01) + (2.057), (I.01) + (2.058), (I.01) + (2.059), (I.01) + (2.060), (I.01) + (3.001), (I.01) + (3.002), (I.01) + (3.003), (I.01) + (3.004), (I.01) + (3.005), (I.01) + (3.006), (I.01) + (3.007), (I.01) + (3.008), (I.01) + (3.009), (I.01) + (3.010), (I.01) + (3.011), (I.01) + (3.012), (I.01) + (3.013), (I.01) + (3.014), (I.01) + (3.015), (I.01) + (3.016), (I.01) + (3.017), (I.01) + (3.018), (I.01) + (3.019), (I.01) + (3.020), (I.01) + (3.021), (I.01) + (3.022), (I.01) + (3.023), (I.01) + (3.024), (I.01) + (3.025), (I.01) + (3.026), (I.01) + (3.027), (I.01) + (3.028), (I.01) + (3.029), (I.01) + (3.030), (I.01) + (3.031), (I.01) + (4.001), (I.01) + (4.002), (I.01) + (4.003), (I.01) + (4.004), (I.01) + (4.005), (I.01) + (4.006), (I.01) + (4.007), (I.01) + (4.008), (I.01) + (4.009), (I.01) + (4.010), (I.01) + (4.011), (I.01) + (4.012), (I.01) + (4.013), (I.01) + (4.014), (I.01) + (4.015), (I.01) + (4.016), (I.01) + (4.017), (I.01) + (4.018), (I.01) + (4.019), (I.01) + (4.(I.01) + (4.001), (I.01) + (4.002), (I.01) + (4.003), (I.01) + (4.004), (I.01) + (4.005), (I.01) + (4.006), (I.01) + (4.007), (I.01) + (4.008), (I.01) + (4.009), (I.01) + (4.010), (I.01) + (4.011), (I.01) + (4.012), (I.01) + (4.013), (I.01) + (4.014), (I.01) + (4.015), (I.01) + (4.016), (I.01) + (4.017), (I.01) + (4.018), (I.01) + (4.019), (I.01) + (4.020), (I.01) + (4.021), (I.01) + (4.022), (I.01) + (4.023), (I.01) + (4.024), (I.01) + (4.025), (I.01) + (4.026), (I.01) + (5.001), (I.01) + (5.002), (I.01) + (5.003), (I.01) + (5.004), (I.01) + (5.005), (I.01) + (5.006), (I.01) + (5.007), (I.01) + (5.008), (I.01) + (5.009), (I.01) + (5.010), (I.01) + (5.011), (I.01) + (5.012), (I.01) + (5.013), (I.01) + (5.014), (I.01) + (5.015), (I.01) + (5.016), (I.01) + (5.017), (I.01) + (5.018), (I.01) + (5.019), (I.01) + (5.020), (I.01) + (5.021), (I.01) + (5.022), (I.01) + (5.023), (I.01) + (6.001), (I.01) + (6.002), (I.01) + (6.003), (I.01) + (6.004), (I.01) + (7.001), (I.01) + (7.002), (I.01) + (7.003), (I.01) + (7.004), (I.01) + (7.005), (I.01) + (7.006), (I.01) + (8.001), (I.01) + (9.001), (I.01) + (9.002), (I.01) + (9.003), (I.01) + (9.004), (I.01) + (9.005), (I.01) + (9.006), (I.01) + (9.007), (I.01) + (9.008), (I.01) + (9.009), (I.01) + (10.001), (I.01) + (10.002), (I.01) + (10.003), (I.01) + (11.001), (I.01) + (11.002), (I.01) + (12.001), (I.01) + (12.002), (I.01) + (12.003), (I.01) + (12.004), (I.01) + (13.001), (I.01) + (13.002), (I.01) + (13.003), (I.01) + (13.004), (I.01) + (13.005), (I.01) + (13.006), (I.01) + (14.001), (I.01) + (14.002), (I.01) + (15.001), (I.01) + (15.002), (I.01) + (15.003), (I.01) + (15.004), (I.01) + (15.005), (I.01) + (15.006), (I.01) + (15.007), (I.01) + (15.008), (I.01) + (15.009), (I.01) + (15.010), (I.01) + (15.011), (I.01) + (15.012), (I.01) + (15.013), (I.01) + (15.014), (I.01) + (15.015), (I.01) + (15.016), (I.01) + (15.017), (I.01) + (15.018), (I.01) + (15.019), (I.01) + (15.020), (I.01) + (15.021), (I.01) + (15.022), (I.01) + (15.023), (I.01) + (15.024), (I.01) + (15.025), (I.01) + (15.026), (I.01) + (15.027), (I.01) + (15.028), (I.01) + (15.029), (I.01) + (15.030), (I.01) + (15.031), (I.01) + (15.032), (I.01) + (15.033), (I.01) + (15.034), (I.01) + (15.035), (I.01) + (15.036), (I.01) + (15.037), (I.01) + (15.038), (I.01) + (15.039), (I.01) + (15.040), (I.01) + (15.041), (I.01) + (15.042), (I.01) + (15.043), (I.01) + (15.044), (I.01) + (15.045), (I.01) + (15.046), (I.01) + (15.047), (I.01) + (15.048), (I.01) + (15.049), (I.01) + (15.050), (I.01) + (15.051), (I.01) + (15.052), (I.01) + (15.053), (I.01) + (15.054), (I.01) + (15.055), (I.01) + (15.056), (I.01) + (15.057), (I.01) + (15.058), (I.01) + (15.059), (I.01) + (15.060), (I.01) + (15.061), (I.01) + (15.062). (I.01) + (15.063). (I.01) + (15.064). (I.01) + (15.065), (I.01) + 15.066), (I.01) + (15.067), (I.01) + (15.068), (I.01) + (15.069), (I.01) + (15.070), (I.01) + (15.071), (I.01) + (15.072), (I.01) + (15.073), (I.01) + (15.074), (I.01) + (15.075), (I.01) + (15.076), (I.01), (I.01) + (15.077), (I.01) + (15.078), (I.01) + (15.079), (I.01) + (15.080), (I.01) + (15.081), (I.01) + (15.082), (I.01) + (15.083), (I.01) + (15.084), (I.01) + (15.085), (I.01) + (15.086), (I.01) + (15.087), (I.01) + (15.088), (I.01) + (15.089), (I.01) + (15.090), (I.01) + (15.091), (I.01) + (15.092), (I.01) + (15.093), (I.01) + (15.094), (I.01) + (15.095), (I.01) + (15.096), (I.01) + (15.097), (I.01) + (15.098), (I.01) + (15.099), (I.01) + (15.100), (I.01) + (15.101), (I.01) + (15.102), (I.01) + (15.103), (I.01) + (15.104), (I.01) + (15.105), (I.01) + (15.106), (I.01) + (15.107), (I.01) + (15.108), (I.01) + (15.109), (I.01) + (15.110), (I.01) + (15.111), (I.01) + (15.112), (I.01) + (15.113), (I.01) + (15.114), (I.01) + (15.115), (I.01) + (15.116), (I.01) + (15.117), (I.01) + (15.118), (I.01) + (15.119), (I.01) + (15.120), (I.01) + (15.121), (I.01) + (15.122), (I.01) + (15.123), (I.01) + (15.124), (I.01) + (15.125), (I.01) + (15.126), (I.01) + (15.127).

[0182] In these combinations, the first component is a compound of formula (I) as defined in Table 1 (e.g. I.01), and the second component is a fungicide selected from groups 1 to 15 as defined herein. For example, the combination (I.01) + (1.001) corresponds to a combination comprising the compound I.01 of Table 1 and cyproconazole (1.001).

[0183] In some other embodiments, the compound combinations correspond to the combinations described above wherein the compound (I.01) is replaced by any one of the compounds listed in Table 1.

[0184] The compound of formula (I) and the fungicide selected from groups (1) to (15) can be present in a weight ratio of 100:1 to 1:100 (compound of formula (I): fungicide selected from groups (1) to (15)), or 50:1 to 1:50, or 20:1 to 1:20. Other examples of weight ratio ranges include 95:1 to 1:95, 90:1 to 1:90, 85:1 to 1:85, 80:1 to 1:80, 75:1 to 1:75, 70:1 to 1:70, 65:1 to 1:65, 60:1 to 1:60, 55:1 to 1:55, 45:1 to 1:45, 40:1 to 1:40, 35:1 to 1:35, 30:1 to 1:30, 25:1 to 1:25, 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2.

[0185] Other fungicides selected from groups 1 to 15 as defined herein can be added to the compound combinations.

[0186] The compounds of formula (I) and compositions comprising the same can be combined with one or more biological control agents.

[0187] Examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising the same are:

[0188] (A) an antibacterial agent selected from the group consisting of:

[0189] (A1) Bacteria, such as (A1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer CropScience LP, US under SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661 and described in US Patent No. 6,060,051); (A1.2) Bacillus amyloliquefaciens, particularly strain D747 (available from Certis, US under Double Nickel). TM (A1.3) Bacillus pumilus, particularly strain BU F-33 (NRRL Registry No. 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (obtained from Novozymes, US). (A1.5) A strain of the genus Paenibacillus sp., NRRL B-50972 or NRRL B-67129 and described in International Patent Publication No. WO 2016 / 154297; and

[0190] (A2) Fungi, such as (A2.1) budding aureobasidium pullulans, especially budding spores of strain DSM14940; (A2.2) budding aureobasidium pullulans of strain DSM 14941; (A2.3) budding aureobasidium pullulans, especially a mixture of budding spores of strains DSM14940 and DSM14941;

[0191] (B) Selected fungicides from the following:

[0192] (B1) Bacteria, such as (B1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer Crop Science LP, US under SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661 and described in US Patent No. 6,060,051); (B1.2) Bacillus pumilus, particularly strain QST2808 (available from Bayer Crop Science LP, US under SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661 and described in US Patent No. 6,060,051); (obtained, registration number NRRL B-30087 and described in U.S. Patent No. 6,245,551); (B1.3) Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE by Yield). (B1.4) Bacillus pumilus, especially strain BU F-33 (NRRL registry number 50185); (B1.5) Bacillus amyloliquefaciens, especially strain D747 (available from Certis, US, via Double Nickel). TM (obtained, registration number FERM BP-8234 and disclosed in U.S. Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan). WP (registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277); (B1.7) Bacillus amyloliquefaciens strain MBI 600 (available from BASF SE under SUBTILEX); (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, DE under SUBTILEX). (B1.9) Bacillus subtilis amyloliquefaciens strain FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as a fungicide); or ECO obtained (EPA registration number 70127-5); (B1.10) Bacillus mycoides, isolate J (obtainable from Certis USA as BmJ TGAI or WG); (B1.11) Bacillus licheniformis, particularly strain SB3086 (obtainable from Novozymes as EcoGuard™ biofungicide and Green Releaf); (B1.12) Bacillus species, registration number NRRL B-50972 or NRRL B-67129 and described in International Patent Publication No. WO 2016 / 154297.

[0193] In some implementations, the biocontrol agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens, which produces fengycin or plipastatin-type compounds, iturin-type compounds, and / or surfactant-type compounds. For background information, please see the following review article: Ongena, M., et al., “Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol,” Trends in Microbiology, Vol. 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available from Bayer CropScience LP, US under SERENADE OPTI or SERENADE ASO, NRRL Registry No. B21661 and described in US Patent No. 6,060,051) and Bacillus amyloliquefaciens strain D747 (available from Certis, US under Double Nickel). TM Obtained, registration number FERM BP-8234 and published in U.S. Patent No. 7,094,592); Bacillus subtilis MBI600 (available from Becker Underwood, US). Obtained (EPA registration number 71840-8); Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan). WP (Registered in Taiwan as a biofungicide under registration numbers 4764, 5454, 5096, and 5277); Bacillus amyloliquefaciens, especially strain FZB42 (available from ABiTEP, DE). (obtained); and Bacillus subtilis amyloliquefaciens variant FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as a fungicide). or ECO obtained (EPA registration number 70127-5); and

[0194] (B2) Fungi, such as: (B2.1) Coniothyrium minitans, especially strain CON / M / 91-8 (accession number DSM-9660; e.g. from Bayer). ) ; (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (e.g. ) ; (B2.3) Microsphaeropsis ochracea (e.g. Mycoshield® from Prophyta ) ; (B2.5) Trichoderma spp., including Trichoderma atroviride strain SCI, described in International Application No. PCT / IT2008 / 000196; (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22, / ATCC 208479, e.g. PLANTSHIELD T-22G, and TurfShield) from BioWorks, US; (B2.14) Gliocladium roseum strain 321U from W.F. Stoneman Company LLC; (B2.35) Talaromyces flavus strain V117b; (B2.36) Trichoderma asperellum strain ICC 012 from Isagro; (B2.37) Trichoderma asperellum strain SKT-1 (e.g. Trichodex® from Kumiai Chemical Industry ) ; (B2.38) Trichoderma atroviride strain CNCM I-1237 (e.g. Trichodex® WP from Agrauxine, FR; ) ; (B2.39) Trichoderma atroviride strain number V08 / 002387; (B2.40) Trichoderma atroviride strain NMI number V08 / 002388; (B2.41) Trichoderma atroviride strain NMI number V08 / 002389; (B2.42) Trichoderma atroviride strain NMI number V08 / 002390; (B2.43) Trichoderma atroviride strain LC52 (e.g. Tenet provided by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride strain T11 (IMI 352941 / CECT 20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum T39 (e.g. Trichodex® from Makhteshim, US; (B2.49) *Trichoderma harzianum*, particularly strain KD (e.g., Trichoplus from Biological Control Products, SA, obtained by Becker Underwood); (B2.50) *Trichoderma harzianum*, strain ITEM 908 (e.g., Trianum-P from Koppert); (B2.51) *Trichoderma harzianum*, strain TH35 (e.g., Root-Pro from Mycontrol); (B2.52) *Trichoderma virens* (also known as *Gliocladium virens*), particularly strain GL-21 (e.g., SoilGard 12G from Certis, US); (B2.53) *Trichoderma viride*, strain TV1 (e.g., Trianum-P from Koppert); (B2.54) *Ampelomyces quisqualis*, particularly strain AQ 10 (e.g., AQ from IntrachemBioItalia). (B2.56) Budding short-stemmed fungi, particularly budding spores of strain DSM14940; (B2.57) Budding short-stemmed fungi, particularly budding spores of strain DSM 14941; (B2.58) Mixtures of budding short-stemmed fungi, particularly budding spores of strains DSM14940 and DSM 14941 (e.g., provided by bio-ferm, CH). (B2.64) Cladosporium cladosporioides, strain H39 (provided by Stichting DienstLandbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonestachys rosea f. catenulate) strain J1446 (e.g., provided by AgBio Inc.) And, for example, those provided by Kemira Agro Oy (B2.70) Conidia of strain KV01 of *Lecanicillium lecanii* (formerly known as *Verticillium lecanii*) (e.g., provided by Koppert / Arysta) ); (B2.71 ) Penicillium vermiculatum ; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) T. atroviride, strain SKT-1 (FERM P-16510); (B2.76) T. atroviride, strain SKT-2 (FERM P-16511 ); (B2.77) T. atroviride, strain SKT-3 (FERM P-17021 ); (B2.78) Trichoderma gamsii (formerly T. virens), strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma provided by AGROBIOSOL DE MEXICO, S.A. DE C.V.); (B2.79) T. harzianum, strain DB 103 (e.g. T-Gro 7456 provided by Dagutat Biolab); (B2.80) T. polysporum, strain IMI 206039 (e.g. Binab TF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.81 ) T. stromaticum (e.g. Tricovab provided by Ceplac, Brazil); (B2.83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen Ltd, NZ provides Botry-Zen®); (B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 (CBS 276.92; e.g. DutchTrig provided by Tree Care Innovations); (B2.86) Verticillium chlamydosporium ; (B2.87) a mixture of T. asperellum strain ICC012 and T. gamsii strain ICC 080 (e.g. product called BIO-TAM® from Bayer CropScience LP, US). TM

[0195] Further examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising the same are:

[0196] ​​bacteria selected from the group consisting of Bacillus cereus, in particular Bacillus cereus strain CNCM 1-1562 and Bacillus firmus, strain 1-1582 (accession number CNCM 1-1582), Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) - PR3 (accession number ATCC SD-5834), Streptomyces microflavus strain AQ 6121 (= QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (accession number NRRL 30232);

[0197] fungi and yeasts selected from the group consisting of Beauveria bassiana, in particular strain ATCC 74040; Lecanicillium spp., in particular strain HRO LEC 12; Metarhizium anisopliae, in particular strain F52 (DSM 3884 or ATCC 90448); Paecilomyces fumosoroseus (now Isaria fumosorosea), in particular strain IFPC 200613 or strain Apopka 97 (Accession No. ATCC 20874); and Paecilomyces lilacinus, in particular Paecilomyces lilacinus strain 251 (AGAL 89 / 030550);

[0198] viruses selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV and Spodoptera littoralis (African cotton leafworm) NPV.

[0199] Bacteria and fungi which can be added to plants or plant parts or plant organs as "inoculants" and which promote plant growth and plant health by virtue of their specific properties. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp, Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp.

[0200] Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biological control agents, such as garlic (Allium sativum), wormwood (Artemisia absinthium), azadirachtin, Biokeeper WP, black shikoku (Cassia nigricans), Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, European leather fern (Dryopteris filix-mas), horsetail (Equisetum arvense), Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM insecticides", rotenone, ryania / ryanodine, comfrey (Symphytum officinale), tansy (Tanacetum vulgare), thymol, Triact 70, TriCon, nasturtium (Tropaeulum majus), stinging nettle (Urtica dioica), veratrin, mistletoe (Viscum album), Brassicaceae extracts (in particular rape meal or mustard meal).

[0201] Examples of insecticides, acaricides and nematicides that can be mixed with the compounds of formula (I) and the compositions comprising the same are, respectively:

[0202] (1) acetylcholinesterase (AChE) inhibitors, for example, carbamates such as alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb;or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isoxathion, malathion, mecarbam, methidathion, mevinphos, naled, omethoate, oxydemeton-methyl, phenthoate, phorate, phosalone, phosmet, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, tebupirimfos, temephos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion.

[0203] (2) GABA-gated chloride channel blockers, such as the cycloalkane-organochlorines, e.g. chlordane and endosulfan, or the fiproles, e.g. ethiprole and fipronil.

[0204] (3) sodium channel modulators, such as pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cy / enoxy isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin (chrysanthemum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin, or methoxychlor.

[0205] (4) competitive modulators of nicotinic acetylcholine receptors (nAChRs), such as neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[0206] (5) allosteric modulators of nicotinic acetylcholine receptors (nAChRs), such as spinosyns, e.g. spinetoram and spinosad.

[0207] (6) allosteric modulators of glutamate-gated chloride channels (GluCls), such as avermectins / milbemycins, e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.

[0208] (7) juvenile hormone mimics, such as juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene, or fenoxycarb, or pyriproxyfen.

[0209] (8) various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulfuryl fluoride or borax or tartar emetic, or methyl isocyanate generators, such as diazomet and metam.

[0210] (9) chordotonal organ modulators, such as pymetrozine or flonicamid.

[0211] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0212] (11) Insect gut membrane-microorganism disruptors, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[0213] (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors, for example diafenthiuron, or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide, or propargite, or tetradifon.

[0214] (13) Uncouplers of oxidative phosphorylation by disruption of proton gradient, for example chlorfenapyr, DNOC and sulfluramid.

[0215] (14) Nicotinic acetylcholine receptor channel blockers, for example bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0216] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0217] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0218] (17) Moulting disruptors (in particular for Diptera, i.e. flies), for example cyromazine.

[0219] (18) ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0220] (19) octopamine receptor agonists, for example amitraz.

[0221] (20) inhibitors of mitochondrial complex III electron transport, for example hydramethylnone or acequinocyl or fluacrypyrim.

[0222] (21) inhibitors of mitochondrial complex I electron transport, for example MET I acaricides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

[0223] (22) voltage-dependent sodium channel blockers, for example indoxacarb or metaflumizone.

[0224] (23) acetyl CoA carboxylase inhibitors, for example tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.

[0225] (24) inhibitors of mitochondrial complex IV electron transport, for example phosphine compounds, for example aluminium phosphide, and phosphine, or cyanide compounds, for example calcium cyanide, potassium cyanide and sodium cyanide.

[0226] (25) inhibitors of mitochondrial complex II electron transport, for example beta-ketonitrile derivatives, for example cyenopyrafen and cyflumetofen, and carboxanilides, for example pyflubumide.

[0227] (26) Ryanodine receptor modulators, for example diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide,

[0228] other active compounds, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, D-trans- Chioroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon-Momfluthrin, Flometoquin, Flua zaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Kappa- Bifenthrin, Kappa-Resmethrin, Lotilaner, Mep erfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Triflumezopyrim and Iodomethane; furthermore, formulations based on Bacillus firmus (I-1582, BioNeem, Votivo) and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl) sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3- en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from EP 2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP 2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO 2012 / 0296672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridinylidene]-1,1,1-trifluoro-propan-2-one (known from WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridinyl)pyrazole-3-carboxamide (known from CN 103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thiacyclobutyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3- thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3- isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)benzamide (known from WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluoropropyl)sulfinyl]-propionamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N- ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H- pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2- propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H- pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro- 2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5- carboxamide (thiobenzamide (Liudaibenjiaxuanan), known from CN 103109816 A) (CAS 1232543- 85-9), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3- chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (CAS 1233882- 22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)- pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6), (2E)-2-[2-(4-cyanophenyl)-1- [3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774 A) (CAS No. 1232543-85-9), 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1 H-benzimidazol-2-yl)phenyl- cyclopropanecarboxylate (known from CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-chloro- 2,5-dihydro-2-[[(methoxy carbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]- indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2), 6-deoxy-3-O-ethyl-2,4-di-O-methyl-,1-[N-[4-[1-[4-(1,1,2,2,2- pentafluoroethoxy)phenyl]-1 H-1,2,4-triazol-3-yl]phenyl]carbamic acid ester]-alpha-L- mannopyranose (known from US 2014 / 0275503 A1) (CAS 1181213-14-8), 8-(2- cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3- aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4- trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6- trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridyl)-1 H-pyrazol-4-yl]- N-ethyl-3-[(3,3,3-(3,4-dichlorophenyl)-8-methoxy-1 -methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbamate (known from WO 2010 / 066780 A1, WO 2011 / 151146 A1 ) (CAS 1229023-00-0), N-[1 -[(6-chloro-3-pyridinyl)methyl]-2(1 H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from DE 3639877 A1, WO 2012029672 A1 ) (CAS 1363400-41 -2), [N(E)]-N-[1 -[(6-chloro-3-pyridinyl)methyl]-2(1 H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from WO 2016005276 A1 ) (CAS 1689566-03-7), [N(Z)]-N-[1 -[(6-chloro-3-pyridinyl)methyl]-2(1 H)-pyridinylidene]-2,2,2-trifluoro-acetamide (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1 ]nonane (known from WO 2011 / 105506 A1, WO 2016 / 133011 A1 ) (CAS 1332838-17-1 ).

[0229] Examples of safeners which can be mixed with the compounds of formula (I) and compositions comprising the same are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0230] Examples of herbicides which can be mixed with the compounds of formula (I) and compositions comprising the same are:

[0231] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate,busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-diolamin, 2,4-D-ethyl,2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropylammonium, 2,4-D-potassium, 2,4-D-triisopropanolammonium and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl,ethoxysulfuron, etobenzanid, F-9600, F-5231 (i.e. N-{2-chloro-4-fluoro-5-[4-(3- fluoropropyl)-5-oxo-4,5-dihydro-1 H-tetrazol-1 -yl]phenyl}ethanesulfonamide), F-7967 (i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]-1 -methyl-6- (trifluoromethyl)pyrimidine-2,4(1 H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop- ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium and flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, and glyphosate-trimesium, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone,HW-02 (i.e. 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate), imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e. 3-({[5-(difluoromethyl)-1 -methyl-3-(trifluoromethyl)-1 H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butoxyethyl ester, MCPA-dimethylammonium salt, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium salt, MCPA-potassium and MCPA-sodium salts, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, mecoprop, mecoprop-sodium and mecoprop-butoxyethyl ester, mecoprop-P, mecoprop-P-butoxyethyl ester, mecoprop-P-dimethylammonium salt,precis 2-methyl-4-chloropropionic acid-2-ethylhexyl ester and potassium salt, mefenacet, melfluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (i.e. N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e. [5-(benzyloxy)-1-methyl-1 H-pyrazol-4-yl](2,4-dichlorophenyl)methanone), neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol,pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, prometon, prometon, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinoclory, quinmerac, quinoclamine,quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), sodium trichloroacetate, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr,trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxy-pyrimidin-2-yl)-oxy]benzyl}-aniline), and the following compounds:

[0232]

[0233] Examples of plant growth regulators are:

[0234] Acibenzolar, benzothiadiazole, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, Brassinolid, catechine, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dymron, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium and endothal mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-beta-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0235] Methods and uses

[0236] The compounds of formula (I) and compositions comprising them have potent microbicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be used in particular for crop protection (they control microorganisms that cause plant diseases) or for the protection of materials described in more detail below (such as technical materials, wood, stored goods). More specifically, the compounds of formula (I) and compositions comprising them can be used for protecting seeds, germinating seeds, young seedlings, plants, plant parts, fruits, harvested goods and / or the soil in which the plants grow from unwanted microorganisms.

[0237] As used herein, controlling ("control" or "controlling") includes protective treatment, curative treatment and eradication treatment of unwanted microorganisms. The unwanted microorganisms can be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes or pathogenic fungi, more particularly plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes or plant pathogenic fungi. As detailed below, these plant pathogenic microorganisms are causal agents of a broad spectrum of plant diseases.

[0238] More specifically, the compounds of formula (I) and compositions comprising them can be used as fungicides. For the purposes of the present description, the term "fungicide" means a compound or a composition that can be used in crop protection to control unwanted fungi and / or oomycetes, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, more preferably Basidiomycetes (causing rust diseases).

[0239] The present application also relates to a method for controlling unwanted microorganisms, such as plant pathogenic fungi, oomycetes and bacteria, which comprises the step of applying at least one compound of formula (I) or at least one composition comprising it to the microorganism and / or its habitat (to the plant, plant part, seed, fruit or soil in which the plant grows).

[0240] In general, when the compounds of the present application and compositions comprising them are used in curative or protective methods for controlling phytopathogenic fungi and / or phytopathogenic Oomycetes, they are applied to the plants, to the plant parts, to the fruits, to the seeds or to the soil or substrate in which the plants grow in effective and plant-tolerable amounts. Suitable substrates that can be used for cultivating plants include inorganic substrates such as mineral wool (in particular rock wool), perlite, sand or gravel; organic substrates such as peat, pine bark or sawdust; and petroleum-based substrates such as polymer foams or plastic beads. By effective and plant-tolerable amounts is meant an amount which is sufficient to control or destroy fungi present or liable to appear in the crops and which does not cause any appreciable symptom of phytotoxicity to the crops. The amount can vary within a wide range depending on the fungi to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the various compounds of the present application or compositions used. This amount can be determined by systematic field trials within the abilities of a person skilled in the art.

[0241] Plants and plant parts

[0242] The compounds of formula (I) and compositions comprising them can be applied to any plant or plant part.

[0243] By plants is meant all plants and plant populations, such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including genetically modified plants (GMO or transgenic plants) and plants which are protected and not protected by plant breeders’ rights.

[0244] By plant parts is to be understood to mean all parts and organs of the plants above and below ground such as shoot, leaf, flower and root, examples including leaves, needles, stems, trunks, flower, fruit bodies, fruits and seeds, as well as roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, runners and seeds.

[0245] Plants which can be treated according to the method of the present application include the following plants: cotton, flax, grapevines, fruit, vegetables, such as Rosaceae sp. (for example pomes, such as apples and pears, and drupes, such as apricots, cherries, plums and peaches, and also stone fruits, such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumbers), Alliaceae sp. (for example leeks, onions), Papilionaceae sp. (for example peas); major crop plants, such as Gramineae sp. (for example maize, turf, cereals, such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Cruciferae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and also oilseed rape, mustard, horseradish and watercress), Fabacae sp. (for example beans, peanuts), Papilionaceae sp. (for example soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugarbeet, fodder beet, Swiss chard, beetroot); useful plants and ornamental plants in horticulture and forestry; and genetically modified varieties of each of these plants.

[0246] In some preferred embodiments, the methods according to the application are carried out on wild plant species and plant cultivars, or those plants which have been obtained by conventional methods of breeding, such as crossing or protoplast fusion, as well as parts of these plants.

[0247] In some other preferred embodiments, the methods according to the application are carried out on transgenic plants and plant cultivars (genetically modified organisms) obtained by genetic engineering methods, if appropriate in combination with conventional methods of breeding, and on their parts. More preferably, plants of the plant cultivars which are commercially available or in use are treated according to the application. Plant cultivars are to be understood as meaning plants which have given rise to new plant varieties by means of genetic engineering or conventional methods of breeding, such as crossing or protoplast fusion. These can be cultivars, varieties, bio- types or genotypes.

[0248] The methods according to the application can be used for the treatment of genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants into which DNA from a different organism has been inserted. The expression "transgene" essentially means a gene which is provided or assembled outside the plant and which, when introduced into the nuclear, chloroplastic or mitochondrial genome, confers a new or improved agronomic or other property on the transformed plant by expressing a protein or polypeptide of interest or by downregulating or silencing one or more other genes which are present in the plant (using, for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A transgene which is located in the genome is also referred to as a transgenic event. A transgenic event is defined according to its specific location in the plant genome and is referred to as a transformation or transgenic event.

[0249] Plants and plant cultivars which can be treated according to the application include all plants (whether wild species or cultivars) of direct or indirect use, including those which can be used for breeding, including plants which are in the process of being developed or genetically modified by breeding, mutagenesis or genetic engineering.

[0250] Plants and plant cultivars which can be treated according to the application include all plants (whether wild species or cultivars) of direct or indirect use, including those which can be used for breeding, including plants which are in the process of being developed or genetically modified by breeding, mutagenesis or genetic engineering.

[0251] Plants and plant cultivars which can be treated according to the application include those which are resistant to one or more biotic stresses, i.e. they show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0252] Plants and plant cultivars which can be treated according to the above disclosed methods include those plants characterized by high yield, disease or pest resistance, stress tolerance, nutritional quality, and improved processing characteristics. Such plants include sunflower, soybean, maize, wheat, rice, cotton, canola, and other crop plants.

[0253] Plants and plant cultivars which can be treated according to the above disclosed methods include plants which are homozygous for one or more loci conferring resistance to herbicides. Such plants can be obtained by the methods of marker assisted selection, gene specific PCR, or genetic tests.

[0254] Plants and plant cultivars which can be treated according to the above disclosed methods include plants which are homozygous for one or more loci conferring resistance to herbicides. Such plants can be obtained by the methods of marker assisted selection, gene specific PCR, or genetic tests.

[0255] Plants and plant cultivars which can be treated according to the above disclosed methods include plants which are homozygous for one or more loci conferring resistance to herbicides. Such plants can be obtained by the methods of marker assisted selection, gene specific PCR, or genetic tests.

[0256] Plants and plant cultivars which can be treated according to the above disclosed methods include plants which are homozygous for one or more loci conferring resistance to herbicides. Such plants can be obtained by the methods of marker assisted selection, gene specific PCR, or genetic tests.

[0257] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars resistant to one or more pests such as fungi, bacteria, viruses and insects, and plants and plant cultivars providing one or more improvements, such as providing triterpenoid compounds.

[0258] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars having altered fiber characteristics, such as cotton plants. Such plants can be obtained by genetic transformation or by selection of plants containing mutations imparting such altered fiber characteristics.

[0259] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars having altered oil profile characteristics, such as oilseed rape or related Brassica plants. Such plants can be obtained by genetic transformation or by selection of plants containing mutations imparting such altered oil profile characteristics.

[0260] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars having altered seed shattering characteristics, such as oilseed rape or related Brassica plants. Such plants can be obtained by genetic transformation or by selection of plants containing mutations imparting such altered seed shattering characteristics, and such plants include plants, such as oilseed rape plants, with delayed or reduced seed shattering.

[0261] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars having altered post-translational protein modification types, such as tobacco plants.

[0262] Pathogens and diseases

[0263] The above disclosed methods can be used for controlling microorganisms causing diseases, in particular phytopathogenic microorganisms, such as phytopathogenic fungi, for example:

[0264] Diseases caused by powdery mildew pathogens, such as Blumeria species (e.g., Blumeria graminis of the Poaceae family), Podosphaera species (e.g., Podosphaera leucotricha), Sphaerothecas species (e.g., Sphaerotheca fuliginea), and Uncinula species (e.g., Uncinula necator of grapes).

[0265] Diseases caused by rust pathogens, such as species of the genus *Gymnosporangium* (e.g., *Gymnosporangium sabinae*), species of the genus *Hemileia* (e.g., *Hemileia vastatrix*), species of the genus *Phakopsora* (e.g., *Phakopsora pachyrhizi* or *Phakopsora meibomiae*), species of the genus *Puccinia* (e.g., *Puccinia recondita*, *Puccinia graminis* or *Puccinia striiformis*), and species of the genus *Uromycesspecies* (e.g., *Uromycesspecies*).

[0266] diseases caused by pathogens from the Oomycetes, such as Albugo species (e.g. Albugo candida), Bremia species (e.g. Bremia lactucae), Peronospora species (e.g. Peronospora pisi or P. brassicae), Phytophthora species (e.g. P. infestans), Plasmopara species (e.g. Plasmopara viticola), Pseudoperonospora species (e.g. Pseudoperonospora humuli or P. cubensis), Pythium species (e.g. Pythium ultimum);

[0267] Leaf blotch and leaf wilt diseases caused by, for example, Alternaria species (e.g. Alternaria solani), Cercospora species (e.g. Cercospora beticola), Cladiosporium species (e.g. Cladiosporium cucumerinum), Cochliobolus species (e.g. Cochliobolus sativus (anamorphic form: Drechslera, syn. Helminthosporium), or Cochliobolus miyabeanus), Colletotrichum species (e.g. Colletotrichum lindemuthanium), Cycloconium species (e.g. Cycloconium oleaginum), Diaporthe species (e.g. Diaporthe citri), Elsinoe species (e.g. Elsinoe fawcettii), Gloeosporium species (e.g. Gloeosporium laeticolor), Glomerella species (e.g. Glomerella cingulate), Guignardia species (e.g. Guignardia bidwelli), Leptosphaeria species (e.g. Leptosphaeria maculans), Magnaporthe species (e.g. Magnaporthe grisea), Microdochium species (e.g. Microdochium nivale), Mycosphaerella species (e.g. Mycosphaerella graminicola), Mycosphaerella species (e.g. Mycosphaerella arachidicola), Mycosphaerella species (e.g. Mycosphaerella fijiensis), Mycosphaerella species (e.g. Mycosphaerella placat a), Phakopsora species (e.g. Phakopsora pachyrizi), Phoma species (e.g. Phoma lingam), Phyllostica species (e.g. Phyllostica citricarpa), Physoderma species (e.g. Physoderma myrtilli), Pseudocercospora species (e.g. Pseudocercospora menesicola), Pyrenochaeta species (e.g. Pyrenochaeta lycopersici), Pyricularia species (e.g. Pyricularia grisea), Pythium species (e.g. Pythium sylvaticum), Ramularia species (e.g. Ramularia areola), Rhabdocline species (e.g. Rhabdocline pseudotsugae), Sclerotinia species (e.g. Sclerotinia homeocarpa), Septoria species (e.g. Septoria lycopersici), Sphaerotheca species (e.g. Sphaerotheca fuliginea), Stagonospora species (e.g. Stagonospora nodorum), Uncinula species (e.g. Uncinula necator), Venturia species (e.g. Venturia inaequalis), and Xanthomonas species (e.g. Xanthomonas campestris).Mycosphaerella species (e.g. Mycosphaerella arachidicola or Mycosphaerella fijiensis), Phaeosphaeria species (e.g. Phaeosphaeria nodorum), Pyrenophora species (e.g. Pyrenophora teres or Pyrenophora tritici repentis), Ramularia species (e.g. Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g. Rhynchosporium secalis), Septoria species (e.g. Septoria apii or Septoria lycopersici), Stagonospora species (e.g. Stagonospora nodorum), Typhula species (e.g. Typhula incarnate), Venturia species (e.g. Venturia inaequalis);

[0268] Root and stem diseases caused by pathogens such as Corticium species (e.g., Corticium graminearum), Fusarium species (e.g., Fusarium oxysporum), Gaeumannomyces species (e.g., Gaeumannomyces graminis), Plasmodiophora species (e.g., Plasmodiophora brassicae), Rhizoctonia species (e.g., Rhizoctonia solani), Sarocladium species (e.g., Sarocladium oryzae), Sclerotium species (e.g., Sclerotium oryzae), Tapesia species (e.g., Tapesia acuformis), Thielaviopsis species (e.g., Thielaviopsis basicola);

[0269] Ear and panicle diseases (including corn cobs) caused by pathogens such as Alternaria species (e.g., Alternaria species), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium cladosporioides), Claviceps species (e.g., Claviceps purpurea), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Monographella species (e.g., Monographella nivalis), Stagnospora species (e.g., Stagnospora nodorum);

[0270] diseases caused by smut fungi, such as Sphacelotheca species (e.g. Sphacelotheca reiliana), Tilletia species (e.g. Tilletia caries or Tilletia controversa), Urocystis species (e.g. Urocystis occulta), Ustilago species (e.g. Ustilago nuda);

[0271] fruit rots caused by pathogen such as Aspergillus species (e.g. Aspergillus flavus), Botrytis species (e.g. Botrytis cinerea), Penicillium species (e.g. Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g. Rhizopus stolonifer), Sclerotinia species (e.g. Sclerotinia sclerotiorum), Verticilium species (e.g. Verticilium alboatrum);

[0272] seed- and soil-borne rot and wilt diseases, as well as seedling diseases, caused by pathogen such as Alternaria species (e.g. Alternaria brassicicola), Aphanomyces species (e.g. Aphanomyces euteiches), Ascochyta species (e.g. Ascochyta lentis), Aspergillus species (e.g. Aspergillus flavus), Cladosporium species (e.g. Cladosporium herbarum), Coccimya species (e.g. Coccimya sphaeriospora (anamorph: Bipolaris, synonym: Helminthosporium)), Colletotrichum species (e.g. Colletotrichum coccodes), Fusarium species (e.g. Fusarium culmorum), Gibberella species (e.g. Gibberella zeae), Macrophomina species (e.g. Macrophomina phaseolina), Microdochium species (e.g. Microdochium nivale), Monacrosporium species (e.g. Monacrosporium phascolorme), Penicillium species (e.g. Penicillium expansum), Phoma species (e.g. Phoma lingam), Phomopsis species (e.g. Phomopsis sojae), Phytophthora species (e.g. Phytophthora cactorum), Pyrenophora species (e.g. Pyrenophora graminea), Pyricularia species (e.g. Pyricularia oryzae), Pythium species (e.g. Pythium ultimum), Rhizoctonia species (e.g. Rhizoctonia solani), Rhizopus species (e.g. Rhizopus oryzae), Sclerotium species (e.g. Sclerotium rolfsii), Septoria species (e.g. Septoria nodorum), Soweromyces species (e.g. Soweromyces rofus), Verticillium species (e.g. Verticillium dahlia);

[0273] Cancerous diseases, galls and broom diseases caused by pathogenic agents such as Nectria species (for example Nectria galligena);

[0274] Wilt diseases caused by pathogenic agents such as Monilinia species (for example Monilinia laxa);

[0275] Deformations of leaves, flowers and fruits caused by pathogenic agents such as Exobasidium species (for example Exobasidium vexans), Taphrina species (for example Taphrina deformans);

[0276] Deteriorative diseases of woody plants caused by pathogenic agents such as Esca species (for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (for example Ganoderma boninense);

[0277] Diseases of flowers and seeds caused by pathogenic agents such as Botrytis species (for example Botrytis cinerea);

[0278] Diseases of plant tubers caused by pathogenic agents such as Rhizoctonia species (for example Rhizoctonia solani), Helminthosporium species (for example Helminthosporium solani);

[0279] Diseases caused by bacterial pathogenic agents such as Xanthomonas species (for example Xanthomonas campestris pv. Oryzae), Pseudomonas species (for example Pseudomonas syringae pv. Lachrymans), Erwinia species (for example Erwinia amylovora).

[0280] Seed treatment

[0281] The method for controlling unwanted microorganisms can be used to protect seeds from attack by phytopathogenic microorganisms (for example fungi).

[0282] As used herein, the term "seed" includes dormant seed, primed seed, pre-germinated seed, and seed that has developed roots and shoots.

[0283] The present application therefore also relates to a method of protecting seed and / or a crop from unwanted microorganisms, such as bacteria or fungi, which comprises the step of treating the seed with one or more compounds of formula (I) or a composition comprising the same. Treating the seed with one or more compounds of formula (I) or a composition comprising the same not only protects the seed from plant pathogenic microorganisms, but also protects the germinating plant, the emerging seedling and the post-emergence plant.

[0284] The seed treatment can be carried out shortly before, at or after sowing.

[0285] When the seed treatment is carried out before sowing (so-called dressing application), the seed treatment can be carried out as follows: the seed can be placed in a mixer containing the required amount of the compound of formula (I) or a composition comprising the same (as such or after dilution), the seed and the compound of formula (I) or a composition comprising the same are mixed until uniform distribution on the seed is achieved. If appropriate, the seed can then be dried.

[0286] The present application also relates to seed treated with one or more compounds of formula (I) or a composition comprising the same. As described hereinbefore, the use of treated seed not only protects the seed before and after sowing from unwanted microorganisms, such as plant pathogenic fungi, but also protects the germinating plant and the seedling that grows from said treated seed from such microorganisms. A large part of the damage caused by pests to crop plants is caused by infection of the seed before sowing or after germination of the plant. This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive, and even small damage can lead to the death of the plant.

[0287] The present application therefore also relates to a method of protecting seed, germinating plants and emerging seedlings, more generally to a method of protecting a crop from plant pathogenic microorganisms, which comprises the step of using seed treated with one or more compounds of formula (I) or a composition comprising the same.

[0288] Preferably, the seed is treated in a state in which it is sufficiently stable not to be damaged during the treatment. In general, the seed can be treated at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and which has been freed from the husks, shells, stems, skins, hairs or flesh. For example, seed can be used which has been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, seed can also be used which has been treated with water after drying, for example, and then dried again, or seed which has just been primed, or seed which has been stored under priming conditions or pregerminated seed, or seed which has been sown in trays, on tapes or on paper.

[0289] The amount of the compound of formula (I) or of the composition comprising it which is applied to the seed is generally such that it does not impair the germination of the seed, or the plant which grows from it. This must be ensured in particular for active ingredients which, at certain application rates, exhibit phytotoxic effects. In determining the amount of the compound of formula (I) or of the composition comprising it to be applied to the seed, the inherent phenotype of the transgenic plant is also taken into account in order to achieve optimum protection of the seed and the germinating plant using the minimum amount of the compound of formula (I) or of the composition comprising it.

[0290] As indicated above, the compound of formula (I) can be applied directly to the seed as such, i.e. without the use of any other components and without the need for dilution, or a composition comprising the compound of formula (I) can be applied. Preferably, the composition is applied to the seed in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, slurries or in combination with other seed coating compositions, such as film-forming materials, granulation materials, iron or other metal powders, granules, seed inactivating coating materials, and ULV formulations. The formulations can be ready-to-use formulations or concentrates which need to be diluted prior to use.

[0291] These formulations are prepared in known manner, for example by mixing the active ingredient or the mixture thereof with customary additives, such as for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, gellants, gibberellins and water.

[0292] These formulations are prepared in known manner, for example by mixing the active ingredient or the mixture thereof with customary additives, such as for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, gellants, gibberellins and water.

[0293] Useful dyes which can be present in the seed-dressing preparations are all dyes which are customary for this purpose. It is possible to use sparingly water-soluble pigments or water-soluble dyes. Examples include the dyes known under the designations Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1. Useful wetting agents which can be present in the seed-dressing preparations are all substances which promote wetting and are customarily used for formulating active agricultural-chemical ingredients. Preference is given to using naphthalenesulphonic acids alkyl esters, such as diisopropyl naphthalenesulphonate or diisobutyl naphthalenesulphonate. Useful dispersants and / or emulsifiers which can be present in the seed-dressing preparations are all non-ionic, anionic and cationic dispersants which are customarily used for formulating active agricultural-chemical ingredients. Preference is given to using non-ionic or anionic dispersants, or mixtures of non-ionic or anionic dispersants. Useful non-ionic dispersants include, inter alia, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and phosphated or sulphated derivatives thereof. Suitable anionic dispersants are, inter alia, lignosulphonic acids, polyacrylic acids and arylsulphonic acids / formaldehyde condensates. Antifoams which can be present in the seed-dressing preparations are all substances which inhibit foaming, which are customarily used for formulating active agricultural-chemical ingredients. Preference is given to using silicone antifoams and magnesium stearate. Preservatives which can be present in the seed-dressing preparations are all substances which can be used for this purpose in agrochemical compositions. Examples include dichlorophen and benzyl alcohol hemiformal. Secondary thickeners which can be present in the seed-dressing preparations are all substances which can be used for this purpose in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silicas. Adhesives which can be present in the seed-dressing preparations are all customary binders which can be used in seed-dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and methyl cellulose.

[0294] The compounds of formula (I) and compositions comprising them are suitable for protecting the seed of any plant variety used in agriculture, in a greenhouse, in a forest or in horticulture. More particularly, the seeds are the seeds of cereals (for example wheat, barley, rye, millet, triticale and oats), oilseed rape, maize, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, peas, sugar beets (for example sugar beet and fodder beet), peanuts, vegetables (for example tomatoes, cucumbers, onions and lettuce), turf grass and ornamentals. Of particular importance is the treatment of the seeds of wheat, soybeans, oilseed rape, maize and rice.

[0295] The compounds of formula (I) or compositions comprising them can be used to treat transgenic seeds, in particular plant seeds which are capable of expressing a protein which has an effect on harmful organisms, herbicide damage or abiotic stress, in order to enhance the protection. Synergistic effects can also occur in the interaction with the substances formed by the expression.

[0296] Nematodes

[0297] In the present context, the term "nematodes" includes all species of the phylum Nematoda and herein in particular species which act as parasites on plants or fungi (e.g. species of the orders Aphelenchida, Meloidogyne, Tylenchida and the like) or on humans and animals (e.g. species of the orders Trichinellida, Tylenchida, Rhabditina and Spirurida) and which cause damage within or on these living organisms, as well as other parasitic worms.

[0298] As described herein, the nematicides in crop protection are capable of controlling nematodes.

[0299] The term "controlling nematodes" means killing nematodes, or preventing or hindering their development or their growth, or preventing or hindering their penetration into plant tissue or their feeding on plant tissue. Herein, the efficacy of a compound is determined by comparing the mortality of nematodes, the gall formation, the cyst formation, the nematode density per volume of soil, the nematode density per root, the number of nematode eggs per volume of soil and the nematode mobility between a plant or plant part treated with a compound of formula (I) and an untreated plant or plant part or untreated soil (100%). Preferably, a reduction of 25 to 50%, particularly preferably of 51 to 79% and very particularly preferably of 80 to 100% of the complete killing or complete prevention of the development and growth of nematodes is achieved compared to an untreated plant, plant part or untreated soil. The control of nematodes as described herein also includes the control of the reproduction of nematodes (development of cysts and / or eggs). The compounds of formula (I) can also be used to keep plants or animals healthy and they can be used therapeutically, prophylactically or systemically to control nematodes.

[0300] The person skilled in the art knows methods for determining the mortality, the gall formation, the cyst formation, the nematode density per volume of soil, the nematode density per root, the number of nematode eggs per volume of soil, the nematode mobility.

[0301] The use of the compounds of formula (I) can keep plants healthy and also includes reducing the damage caused by nematodes and increasing the yield of the harvest.

[0302] In the present context, the term "nematodes" refers to plant nematodes, which include all nematodes that harm plants. Plant nematodes include plant-parasitic nematodes and soil-borne nematodes. Plant-parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp. and Trichodorus spp.; semi-parasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp. and Scutellonema spp.; non-migratory parasites such as Heterodera spp., Globodera spp. and Meloidogyne spp.; and stem- and leaf-endoparasites such as Ditylenchus spp., Aphelenchoides spp. and Hirschmaniella spp.. Particularly harmful root-parasitic soil nematodes are for example cyst-forming nematodes of the genus Heterodera or Globodera and / or root galling nematodes of the genus Meloidogyne. Destructive species of these genera are for example Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida and Globodera rostochiensis (yellow potato cyst nematode), the control of which is effectively achieved by the compounds described herein. However, the use of the compounds described herein is by no means limited to these genera or species, but extends in the same way to other nematodes.

[0303] Plant nematodes include, for example, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria and species of the genus Aphelenchoides endophyte of stems and leaves, Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax) and Criconemella spp., Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and Ditylenchus spp. endophyte of stems and leaves, Dolichodorus heterocephalus, Globodera pallida (= Heterodera pallida), Globodera rostochiensis (yellow form of the potato cyst nematode), Globodera solanacearum, Globodera tabacum, GloboderaHelicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus, and Helicotylenchus spp., Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae, and Heteroderaspp. (non-migratory cyst-forming parasites), Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata, and Hirshmanniella spp. (stem and leaf internal parasites), Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, LongidorusThe species *Vineacola* and its ectoparasites, including *Meloidogyne*, *Meloidogyne acronea*, *Meloidogyne africana*, *Meloidogyne arenaria*, *Meloidogyne arenariathamesi*, *Meloidogyne artiella*, *Meloidogynechitwoodi*, *Meloidogyne coffeicola*, *Meloidogyne ethiopica*, *Meloidogyne exigua*, *Meloidogyne fallax*, *Meloidogyne graminicola*, *Meloidogyne graminis*, and *Meloidogyne granatum*. The following species are listed: *Hapla*, *Meloidogyne incognita acrita*, *Meloidogyne javanica*, *Meloidogyne kikuyensis*, *Meloidogyne minor*, *Meloidogyne naasi*, *Meloidogyne paranaensis*, *Meloidogyne thamesi*, and non-migratory parasitic root-knot nematodes of the genera *Meloidogyne*, *Meloidogyne*, *Nacobbus aberrans*, *Neotylenchus vigissi*, *Paraphelenchus pseudoparietinus*, *Paratrichodorus allius*, *Paratrichodorus lobatus*, and *Paratrichodorus*. The following nematodes are listed: *Paratrichodorus nanus*, *Paratrichodorus porosus*, *Paratrichodorus teres*, and *Paratrichodorus spp.*, *Paratylenchushamatus*, and *Paratylenchus*.*Pratylenchus minutus*, *Pratylenchus projectus*, and *Pratylenchus spp.*, *Pratylenchus agilis*, *Pratylenchus alleni*, *Pratylenchus andinus*, *Pratylenchus brachyurus*, *Pratylenchus cerealis*, *Pratylenchus coffeae*, *Pratylenchus crenatus*, *Pratylenchus delattrei*, *Pratylenchus giibbicaudatus*, *Pratylenchus goodeyi*, *Pratylenchus hamatus*, *Pratylenchus hexincisus*, and *Pratylenchus lous*. *Pratylenchus neglectus*, *Pratylenchus penetrans*, *Pratylenchus pratensis*, *Pratylenchus scribneri*, *Pratylenchus teres*, *Pratylenchus thornei*, *Pratylenchus vulnus*, *Pratylenchus zeae*, and migratory endoparasites *Pseudohalenchus minutus*, *Psilenchus magnidens*, *Psilenchus tumidus*, *Punctodera chalcoensis*, *Quinisulcius acutus*, *Radiopholus citrophilus*, and similar perforating nematodes. similis), migratory endoparasites, perforating nematodes, *Rotylenchulus borealis*, *Rotylenchulus parvus*, *Rotylenchulus reniformis*, and *Rotylenchulus* species.spp.), *Rotylenchus laurentinus*, *Rotylenchus macrodoratus*, *Rotylenchus robustus*, *Rotylenchus uniformis* and *Rotylenchus spp.*, *Scutellonema brachyurum*, *Scutellonema bradys*, *Scutellonema clathricaudatum* and migratory endoparasites, *Subanguina radiciola*, *Tetylenchus nicotianae*, *Trichodorus cylindricus*, *Trichodorus minor*, *Trichodorus primitivus*, *Trichodorus* *Trichodorus proximus*, *Trichodorus similis*, *Trichodorus sparsus*, and ectoparasites *Trichodorus* species, *Tylenchorhynchus agri*, *Tylenchorhynchus brassicae*, *Tylenchorhynchus clarus*, *Tylenchorhynchus claytoni*, *Tylenchorhynchus digitatus*, *Tylenchorhynchus ebriensis*, *Tylenchorhynchus maximus*, *Tylenchorhynchus nudus*, *Tylenchorhynchus vulgaris*, and dwarf nematodes (*Tylenchorhynchus spp.*), *Tylenchulus*. The genus *Xiphinema* includes semipenetrans, and species of the hemiparasitic nematode *Xiphinema americanum*, *Xiphinema brevicolle*, *Xiphinema dimorphicaudatum*, *Xiphinema index*, and species of the ectoparasitic nematode *Xiphinema*.

[0304] Nematodes that can be controlled using the compounds of formula (I) include nematodes of the genus Meloidogyne, such as M. incognita, M. javanica, M. hapla and M. arenaria; of the genus Ditylenchus, such as D. destructor (cave worm) and D. dipsaci (lawn and bulb nematode); of the genus Pratylenchus, such as P. penetrans (banana root nematode), P. fallax (chrysanthemum root nematode), P. coffeae (coffee root nematode), P. latus (tea root nematode) and P. glomerata (walnut root nematode); of the genus Globodera, such as G. rostochiensis (potato golden nematode) and G. pallida (potato white nematode); of the genus Heterodera, such as H. glycines (soybean cyst nematode) and H. schachtii (beet cyst nematode); of the genus Aphelenchoides, such as A. besseyi (rice leaf shear nematode), A. ritzemabosi (chrysanthemum leaf nematode) and A. fragariae (strawberry nematode); of the genus Aphelenchus, such as A. avenue (fungivorous nematode); of the genus Tylenchus, such as T. phormus (similar Tylenchus); of the genus Bursaphelenchus, such as B. xylophilus (pine wood nematode); of the genus Radoophorus, such as R. similis (banana root nematode); of the genus Nephrocytospora, such as N. reniformis (kidney-shaped nematode); and tree-dwelling nematodes such as Bursaphelenchus cocophilus (coconut red ring nematode) and the like.

[0305] The plants which can be protected using the compounds of the formula (I) include the following plants: for example cereals (e.g. rice, barley, wheat, rye, oats, maize, etc.), leguminous plants (soybean, red bean, kidney bean, pea, peanut, etc.), fruit trees / fruits (apple, citrus, pear, grapevine, peach, Japanese apricot, cherry, walnut, almond, banana, strawberry, etc.), vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, leek, pepper, etc.), root crops (carrot, potato, sweet potato, radish, lotus root, turnip, etc.), plants for industrial raw materials (cotton, paper mulberry, mitsumata, rape, sugar beet root, hops, sugarcane, sugar beet, olive, rubber, palm, coffee, tobacco, tea, etc.), cucurbits (pumpkin, cucumber, watermelon, muskmelon, etc.), meadow plants (cocksfoot, sorghum, timothy-grass, clover, alfalfa, etc.), turf grasses (mascarene grass, bentgrass, etc.), spice plants, etc. (lavender, rosemary, thyme, parsley, pepper, ginger, etc.) and flowers (chrysanthemum, rose, orchid, etc.).

[0306] The compounds of the formula (I) are particularly suitable for controlling coffee nematodes, in particular Pratylenchus brachyurus, P. coffea, P. penetrans, P. curtiti, P. goodeyi, Helicotylenchus spp. and Pratylenchus paranaica, Helicotylenchus spp., Longidorus spp. and Tylenchorhynchus spp.

[0307] The compounds of the formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, P. pratensis, P. scriputeri, P. penetrans, P. coffea, Globodera rostochiensis and Pratylenchus alleni, P. andina, P. cerealis, P. crenatus, P. sixdentatus, P. loboa, P. lucidus, P. thornei, P. vulnus, Longidorus elongates, Paralongidorus primarius, Paralongidorus proximus, Paratylenchus microbursatus, Paratylenchus alleni, Paratylenchus brachyurus, Paratylenchus dianae, Paratylenchus loosi, Paratylenchus fallax, Paratylenchus gagnevinus, Paratylenchus gregalis, Meloidogyne arenaria, M. hapla, M. incognita, M. javanica, Tylenchorhynchus claytoni, T. niger, T. swartzi, T. agri, T. clematidis, T. nellovi, T. niger, T. parvus, T. torquens, T. xenoplax, Globodera pallida, G. rostochiensis, Ditylenchus destructor, D. myceliophagus, Meloinema spp.

[0308] Compounds of formula (I) are particularly effective in controlling tomato nematodes, especially peanut root-knot nematodes, northern root-knot nematodes, Javan root-knot nematodes, southern root-knot nematodes, piercing short-bodied nematodes, as well as the shortest-tailed short-bodied nematode, coffee short-bodied nematode, Strychni short-bodied nematode, damaged short-bodied nematode, tiny hairy nematode, short root-knot nematode, abnormal pearl nematode, green lye cyst nematode, Dolichodorus heterocephalus, and kidney-shaped nematode.

[0309] Compounds of formula (I) are particularly effective in controlling cucumber plant nematodes, especially peanut root-knot nematodes, northern root-knot nematodes, Javan root-knot nematodes, southern root-knot nematodes, kidney-shaped nematodes, and Solomon's short-bodied nematodes.

[0310] Compounds of formula (I) are particularly effective in controlling cotton nematodes, especially long-tailed spiny nematode, southern root-knot nematode, Columbus nematode, helmet-shaped nematode and kidney-shaped nematode.

[0311] Compounds of formula (I) are particularly effective in controlling maize nematodes, especially *Nematoda long-tailed nematode*, *Nematoda microspinosa*, *Nematoda short-tailed nematode*, *Nematoda delatina*, *Nematoda hexalobata*, *Nematoda piercingii*, *Nematoda maize*, *Nematoda scabra*, *Nematoda Nortonensis*, *Nematoda short-ringed nematode*, *Nematoda peanut*, *Nematoda Thames*, *Nematoda grasses*, *Nematoda southernis*, *Meloidogyne incognita acrita*, *Nematoda Javanese*, *Nematoda Naxiensis*, *Nematoda oats*, *Nematoda rice*, *Nematoda maize*, *Punctodera chalcoensis*, *Nematoda bulbosa*, *Nematoda hemianis*, *Nematoda hemianis*, *Nematoda hemianis*, *Nematoda Indianis*, *Nematoda bicornuate*, *Nematoda bisporus*, *Nematoda pseudostrongensis*, *Nematoda Americanis*, and *Dolichodorus*. Heterocereus heterocephalus, Decorative Ring Nematode, Oenian Ring Nematode, Similar Perforating Nematode, Northern Spiral Nematode, Miniature Kidney Nematode, Farmland Dwarf Nematode, Clear Dwarf Nematode, Clayton Dwarf Nematode, Largest Dwarf Nematode, Naked Dwarf Nematode, Common Dwarf Nematode, Five-Hook Nematode, Miniature Needle Nematode, Hemicycliophora parvana, Juno Rough-striped Pad-edge Nematode, Wheat Grain Nematode, Peanut Smooth-edge Nematode, Short-tailed Shield Nematode, and Root Gall Nematode.

[0312] The compounds of formula (I) are particularly suitable for controlling soybean nematodes, in particular Pratylenchus brachyurus, P. graminum, P. penetrans, P. scriputi, P. zeae, P. goodeli, P. coffeae, P. hexatricus, P. fallax, P. notatus, P. alleni, P. andinus, P. curvitatus, P. thornei, P. virginiae, P. crenatus, P. robustus, P. acris, P. incognita, P. acrita, P. javanicus, P. major, P. minuta, P. pratensis, P. silvestru, P. thornei, P. virginiae, P. reniformis, P. clintoni, P. penetrans, P. fallax, and P. minuta.

[0313] The compounds of formula (I) are particularly suitable for controlling tobacco nematodes, in particular P. southern root-knot nematode, P. javanicus, and P. brachyurus, P. graminum, P. hexatricus, P. penetrans, P. fallax, P. thornei, P. zeae, P. alleni, P. andinus, P. curvitatus, P. notatus, P. virginiae, P. crenatus, P. robustus, P. thornei, P. virginiae, P. reniformis, P. clintoni, P. penetrans, P. fallax, and P. minuta.

[0314] The compounds of formula (I) are particularly suitable for controlling citrus nematodes, in particular P. coffeae, and P. brachyurus, P. thornei, P. zeae, P. alleni, P. andinus, P. curvitatus, P. notatus, P. fallax, P. hexatricus, P. minuta, P. reniformis, P. clintoni, P. penetrans, P. fallax, P. acris, P. incognita, P. acrita, P. javanicus, P. major, P. silvestru, P. thornei, P. virginiae, P. reniformis, P. clintoni, P. penetrans, P. fallax, and P. minuta.

[0315] The compounds of formula (I) are particularly suitable for controlling banana nematodes, in particular P. coffeae, P. similis, and P. giibbicaudatus, P. loosi, Meloidogyne spp., Helicotrichodorus spp., Rotylenchus spp., and Nematodirus spp.

[0316] Compounds of formula (I) are particularly effective in controlling pineapple nematodes, especially maize short-bodied nematodes, grassland short-bodied nematodes, shortest-tailed short-bodied nematodes, Goudy short-bodied nematodes, root-knot nematodes, kidney-shaped nematodes, and long-needle nematodes, Longidorus laevicapitatus, primitive hairy nematodes, tiny hairy nematodes, Heteroderm nematodes, mushroom stem nematodes, California nematodes, pseudo-strong nematodes, Indian nematodes, double-spiral nematodes, Helicotylenchusnannus, multi-banded spiral nematodes, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, similar perforating nematodes, finger-shaped dwarf nematodes, Tylenchorhynchus ebriensis, tiny needle nematodes, shield nematodes of Hyyne, slow shield nematodes, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus Minutus, Criconemoides onoense, and Criconemoides ornatum.

[0317] Compounds of formula (I) are particularly effective in controlling grapevine nematodes, especially *Synthia striata*, *Synthia striata*, *Synthia striata*, *Synthia striata*, *Synthia striata*, *Synthia striata*, as well as *Synthia striata*, *Synthia striata*, *Synthia striata*, *Synthia striata*, *Synthia striata*, and *Synthia striata*.

[0318] Compounds of formula (I) are particularly effective in controlling nematodes in tree crops—peat fruits, especially piercing short-bodied nematodes, as well as wounded short-bodied nematodes, removed long-needle nematodes, southern root-knot nematodes, and northern root-knot nematodes.

[0319] Compounds of formula (I) are particularly effective in controlling nematodes in tree crops—drupes, especially *Stachys punctata*, *Stachys malformata*, *Peanut Root-knot Nematode*, *Northern Root-knot Nematode*, *Java Root-knot Nematode*, *Southern Root-knot Nematode*, *Stachys pulvinata* and *Stachys pulvinata*, *Coffee Nematode*, *Stachys skeletalus*, *Maize Nematode*, *Long-tailed Spiny Nematode*, *Double-bodied Spiny Nematode*, *American Fiber Nematode*, *Curved Spiny Nematode*, *Clayton Dwarf Nematode*, *Hooked Needle Nematode*, *Protruding Needle Nematode*, *Stachys pulvinata*, and *Helmet-shaped Nematode*.

[0320] The compounds of formula (I) are particularly effective in controlling nematodes in tree crops, sugarcane and rice, especially species of the genera *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda*, *Nematoda* and harmful necrotic nematodes.

[0321] Application

[0322] The compounds of formula (I) can be applied as such or, for example, in the form of ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with a compound of formula (I), synthetic substances impregnated with a compound of formula (I), fertilizers or microencapsulations in polymeric substances.

[0323] The application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading and the like. It is also possible to use the compounds of formula (I) by the ultra-low-volume process, by drip irrigation systems or by drenching, applying them in the furrow or injecting them into the stem or trunk of the plants in the soil. It is also possible to apply the compounds of formula (I) by wound sealing, coating or other wound dressings.

[0324] The effective and phyto- compatible amount of the compounds of formula (I) applied to the plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound / composition used, the treated subject (plants, plant parts, fruits, seeds or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (therapeutic and protective), the type of microorganism, the development stage of the microorganism, the sensitivity of the microorganism, the crop growth stage and the environmental conditions.

[0325] When the compounds of formula (I) are used as fungicides, the application rates can vary within a relatively wide range, depending on the type of application. For the treatment of plant parts, such as leaves, the application rates can be from 0.1 to 10000 g / ha, preferably from 10 to 1000 g / ha, more preferably from 50 to 300 g / ha (in the case of application by watering or dripping, the application rates can even be reduced, in particular when using inert substrates such as rock wool or perlite). For the treatment of seeds, the application rates can be from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, more preferably from 2.5 to 25 g per 100 kg of seeds, even more preferably from 2.5 to 12.5 g per 100 kg of seeds. For the treatment of soil, the application rates can be from 0.1 to 10000 g / ha, preferably from 1 to 5000 g / ha.

[0326] These application rates are merely examples and are not intended to limit the scope of the present application.

[0327] Material protection

[0328] The compounds and compositions of the present application can also be used for the protection of materials, in particular for the protection of industrial materials against the attack and destruction by unwanted microorganisms.

[0329] Furthermore, the compounds and compositions of the present application can be used as antifouling compositions, alone or in combination with other active ingredients.

[0330] In the present context, technical material is to be understood as meaning inanimate material which is prepared for technical use. For example, technical material which is to be protected from microbial alteration or destruction can be adhesives, glues, paper, wallpaper and wood / chipboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infested or destroyed by microorganisms. Mention can also be made in the range of materials to be protected of components of production plants and buildings which can be damaged by the propagation of microorganisms, for example cooling water circuits, cooling and heating systems and ventilation and air conditioning units. Within the scope of the present application, technical material preferably includes adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

[0331] The compounds and compositions of the present application can prevent adverse effects such as rot, decay, discoloration, fading or mold.

[0332] In the case of treatment of wood, the compounds and compositions of the present application can also be used against fungal diseases which tend to grow on the surface of wood or inside the wood.

[0333] Wood means all types of wood species, and all types of processed products of this wood which are used for construction, for example solid wood, high-density wood, laminated wood and plywood. Furthermore, the compounds and compositions of the present application can be used to protect objects which come into contact with salt water or slightly salty water, especially ship hulls, screens, nets, buildings, mooring equipment and signaling systems, from contamination.

[0334] The compounds and compositions of the present application can also be used to protect stored goods. Stored goods are to be understood as meaning natural substances of vegetable or animal origin or processed products thereof, which are of natural origin and require long-term protection. Stored goods of vegetable origin, for example plants or plant parts, for example stems, leaves, tubers, seeds, fruits, grains, can be protected after harvesting or after processing by (pre)drying, moistening, crushing, grinding, pressing or baking. Stored goods also include wood, including unprocessed wood, for example construction timber, telegraph poles and fences, or wood in finished form, for example furniture. Stored goods of animal origin are, for example, hides, leather, furs and hairs. The compounds and compositions of the present application can prevent adverse effects such as rot, decay, discoloration, fading or mold.

[0335] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds and compositions of the present application preferably act on fungi, especially on moulds, wood discolouring and wood destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and on slime organisms and algae.Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp., and Tyromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp., and Saccharomyces spp., such as Saccharomyces cerevisae.

[0336] EMBODIMENT

[0337] Synthesis of compounds of formula (I)

[0338] Preparation Example 1Preparation of 5-(4,5-dibromo-3-fluoro-2-thienyl)-6-thioxo-4-azaspiro[2.4]heptan- 7-one (Compound 1.03)

[0339] Step 1 Preparation of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropane- carboxylic acid methyl ester

[0340] Under inert atmosphere, a solution of 733 mg (4.33 mmol) of 2-chloro-1,3- dimethylimidazolidinium chloride in 4.3 mL of dichloromethane was added to a solution of 1.0 g (3.33 mmol) of 4,5-dibromo-3-fluorothiophene-2-carboxylic acid and 2.50 mL (14.3 mmol) of N,N-diisopropylethylamine in 35 mL of dichloromethane. After stirring for 15 min, 1.0 g (6.66 mmol) of 1 -aminocyclopropanecarboxylic acid methyl ester hydrochloride (1 :1 ) was added and the reaction mixture was stirred at room temperature for 72 h. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were filtered through a Chem Elut cartridge and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient dichloromethane / ethyl acetate) to give 1.24 g (100% purity, 93% yield) of the title compound as a white solid. LogP = 2.77. (M+H) = 400. TM

[0341] Step 2 Preparation of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropane- carboxylic acid methyl ester

[0342] Lawesson's reagent, 267 mg (0.66 mmol), was added to a solution of 265 mg (0.65 mmol) of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropane- carboxylic acid methyl ester in 5 mL of 1,2-dimethoxyethane. The reaction mixture was stirred at 50 °C for 42 h. The resulting reaction mixture was diluted with dichloromethane and filtered through a basic alumina cartridge. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane / ethyl acetate) to give 158 mg (100% purity, 57% yield) of the title compound as a yellow solid. LogP = 3.91. (M+H) = 416.

[0343] Step 3 Preparation of 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropane- carboxylic acid​​

[0344] To a solution of 271 mg (0.47 mmol) of methyl 1-{[(4,5-dibromo-3-fluoro-2- thienyl)thioxomethyl]amino}cyclopropanecarboxylate in 7 mL of 1,2- dichloroethane was added 203 mg (0.47 mmol) of trimethyltin hydroxide. The reaction mixture was stirred at 60 °C for 18 h. The resulting reaction mixture was concentrated under reduced pressure, dissolved in acetylacetate, and washed with 1.0 M aqueous hydrochloric acid three times. The combined organic layers were passed through a Chem Elut TM The filter cartridge was filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / aqueous formic acid (1%)) to give 135 mg (100% purity, 54% yield) of the title compound as a yellow solid. LogP = 2.95. (M+H) = 402.

[0345] Step 4 Preparation of 5-(4,5-dibromo-3-fluoro-2-thienyl)-6-thioxo-4-azaspiro[2.4]heptan-4- en-7-one (Compound I.03)

[0346] To a solution of 70 mg (0.17 mmol) of 1-{[(4,5-dibromo-3-fluoro-2- thienyl)thioxomethyl]amino}cyclopropanecarboxylic acid in 2 mL of dichloromethane was added 43 mg (0.22 mmol) of 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 18 h. Water was added and the resulting reaction mixture was extracted with dichloromethane twice. The combined organic layers were passed through a Chem Elut TM The filter cartridge was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 51 mg (94% purity, 72% yield) of the title compound as a light pink solid. LogP = 5.08. (M+H) = 384.

[0347] Preparation Example 2 Preparation of 3-bromo-4-methyl-5-(7-oxo-6-oxa-4-azaspiro[2.4]heptan-4-en-5-yl)thiophene- 2-carbonitrile (Compound I.06)

[0348] Step 1 Preparation of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid

[0349] To a solution of 150 mg (0.86 mmol) of 4-bromo-5-cyano-3-methylthiophene-2- carboxylic acid methyl ester in 3.9 mL of tetrahydrofuran was added dropwise 0.7 mL of 1.1 M aqueous lithium hydroxide (0.7 mmol). The reaction mixture was stirred at room temperature for 1 hour. The resulting reaction mixture was carefully acidified with 1.0 M aqueous hydrochloric acid at 0 °C and extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 142 mg (97% purity, 97% yield) of the title compound as a white solid. LogP = 2.05. (M+H) = 246.

[0350] Step 2 Preparation of 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropane carboxylic acid methyl ester

[0351] To a solution of 1.34 g (7.92 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride in 7.9 mL of dichloromethane was added to a solution of 1.50 mg (6.09 mmol) of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid and 4.57 mL (26.2 mmol) of N,N-diisopropylethylamine in 50 mL of dichloromethane. After stirring for 15 minutes, 1.85 g (12.1 mmol) of 1- aminocyclopropanecarboxylic acid methyl ester hydrochloride (1:1) was added and the reaction mixture was stirred at room temperature for 72 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. The resulting reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient dichloromethane / ethyl acetate) to give 1.55 g (96% purity, 71% yield) of the title compound as a white solid. LogP = 2.31. (M+H) = 343.

[0352] Step 3 Preparation of 1-{[(4-bromo-5-cyano-3-methyl-2-thienyl)carbonyl]amino}cyclopropane carboxylic acid

[0353] To a solution of 400 mg (1.16 mmol) of 1-{[(4-bromo-5-cyano-3-methyl-2- thienyl)carbonyl]amino}cyclopropanecarboxylic acid methyl ester in 8.0 mL of tetrahydrofuran was added dropwise 1.5 mL of 1.0 M aqueous lithium hydroxide (0.7 mmol). The reaction mixture was stirred at room temperature for 2 hours. The resulting reaction mixture was carefully acidified with 1.0 M aqueous hydrochloric acid at 0 °C to pH 1 and extracted with ethyl acetate 3 times. The combined organic layers were passed through Chem Elut TMThe filter cartridge was filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / water formic acid (1%)) to give 301 mg (92% purity, 72% yield) of the title compound as a white solid. LogP = 1.88. (M+H) = 329.

[0354] Step 3bis Alternative preparation of 1-{[(4-bromo-5-cyano-3-methyl-2- thienyl)carbonyl]amino}cyclopropanecarboxylic acid

[0355] In a first round bottom flask, 47 μL (0.53 mmol) of oxalyl chloride and one drop of N,N-dimethylformamide were added to a solution of 120 mg (0.48 mmol) of 4-bromo-5-cyano-3-methylthiophene-2-carboxylic acid in 4 mL of anhydrous dichloromethane at room temperature. After stirring at room temperature for 45 minutes, the reaction mixture was concentrated under reduced pressure and dissolved in 2 mL of anhydrous 1,4-dioxane to give an acyl chloride solution. In a second round bottom flask, 1.46 mL of a 1.0 M aqueous sodium hydroxide solution (1.46 mmol) were added to a solution of 134 mg (0.97 mmol) of 1- aminocyclopropanecarboxylic acid hydrochloride (1:1) in 1 mL of water. The reaction mixture was stirred at room temperature for 30 minutes, then it was slowly added at 0°C to the previously prepared acyl chloride solution. The resulting reaction mixture was stirred at room temperature for 24 hours, diluted with water, carefully acidified to pH 1 at 0°C with a 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic layers were passed through a Chem Elut TM The filter cartridge was filtered and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile / water formic acid (1%)) to give 65 mg (100% purity, 41% yield) of the title compound as a white solid. LogP = 1.84. (M+H) = 329.

[0356] Step 4 Preparation of 3-bromo-4-methyl-5-(7-oxo-6-oxa-4-azaspiro[2.4]hept-4- en-5-yl)thiophene-2-carbonitrile (Compound I.06)

[0357] In a 100 mL round bottom flask under inert atmosphere, a solution of 80 mg (0.47 mmol) of 2-chloro-l,3-dimethylimidazolidinium chloride in 0.47 mL of dichloromethane was added to a solution of 1.0 g (3.33 mmol) of l-{[(4-bromo-5-cyano-3-methyl-2- thienyl)carbonyl]amino}cyclopropanecarboxylic acid and 0.19 mL (1.09 mmol) of N,N- diisopropylethylamine in 4 mL of dichloromethane. The reaction mixture was stirred at room temperature for 18 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. The combined organic layers were passed through Chem Elut TM The filter cartridge was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 87 mg (100% purity, 77% yield) of the title compound as a white solid. LogP = 3.37. (M+H) = 311.

[0358] Exemplary compounds

[0359] Exemplary compounds of the application as shown in Table 1 were prepared analogously to the examples provided hereinabove and / or according to the general instructions of the methods disclosed herein.

[0360] The following Table 1 illustrates, in a non-limiting manner, examples of compounds of formula (I).

[0361]

[0362] Table 1 :

[0363]

[0364]

[0365] In the above table, the LogP values were measured by HPLC (High Performance Liquid Chromatography) on a reversed phase column using the following method according to EEC directive 79 / 831 Annex V.A8:

[0366] [a] The LogP values were determined by LC-UV measurement in the acidic range using 0.1% formic acid in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0367] [b] The LogP values were determined by LC-UV measurement in the neutral range using 0.001 molar ammonium acetate in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0368] [c]LogP values ​​were determined by LC-UV measurement in an acidic range using 0.1% phosphoric acid and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0369] If more than one LogP value can be obtained in the same method, give all the values ​​and separate them with "+".

[0370] Calibration was performed using straight-chain alkyl-2-ones (with 3 to 16 carbon atoms) with known LogP values ​​(LogP values ​​were measured using retention times via linear interpolation between consecutive alkyl-2-ones). The maximum value of λ was determined using UV spectra and chromatographic signal peaks from 200 nm to 400 nm.

[0371] NMR peak list

[0372] Table A provides NMR data for some of the compounds disclosed in the table above. 1 H).

[0373] Selected Implementation 1 H-NMR data with 1 The H-NMR peaks are listed in the form of a table. For each signal peak, the δ value in ppm is listed, and the signal intensity is listed in parentheses. The δ value-signal intensity pairs are separated by semicolons.

[0374] Therefore, the peak list of one embodiment has the following form:

[0375] δ1 (Intensity 1); δ2 (Intensity 2); ...; δ i (strength i );……;δ n (strength n )

[0376] The intensity of the spike signal is highly correlated with the signal in cm in the printed NMR spectrum example, showing the true relationship of signal intensity. Broad peak signals can be used to display several peaks or intermediate peaks of the signal and their relative intensity compared to the strongest signal in the spectrum.

[0377] For calibration 1 For the chemical shifts in the 1H NMR spectrum, we use the chemical shifts of tetramethylsilane and / or the solvent used, especially in the case of spectra measured in DMSO. Therefore, the peak of tetramethylsilane may, but is not necessarily, appear in the NMR peak list.

[0378] 1 H-NMR peak list and conventional 1 H-NMR prints are similar and therefore typically include all peaks listed in a standard NMR description.

[0379] In addition, as usual 1H-NMR prints, which can show solvent signals, signals of stereoisomers of the target compound (which are also the object of the present application) and / or signals of impurity peaks.

[0380] In order to show the compound signals in the delta range of the solvent and / or water, in our 1 The conventional peaks of the solvent, e.g. the peaks of DMSO and water in DMSO-D6, are shown in the H-NMR peak list and usually have an average high intensity.

[0381] The peaks of stereoisomers of the target compound and / or the peaks of impurities usually have an average lower intensity than the peaks of the target compound (e.g. with > 90% purity).

[0382] Such stereoisomers and / or impurities can be specific for the particular preparation method. Thus, their peaks can help to identify the reproducibility of our preparation method by "side-products-fingerprints".

[0383] The expert calculates the peaks of the target compound by known methods (MestreC, ACD simulation, and with expected values assessed empirically) and can optionally use additional intensity filters to isolate the peaks of the target compound, if necessary. This isolation is similar to the conventional 1 The relevant peak picking in the H-NMR description.

[0384] Further details on the NMR data description of the peak list can be found in the publication "Citation of NMR Peaklist Data within Patent Applications" of Research Disclosure Database No. 564025.

[0385] Table A NMR peak list

[0386]

[0387]

[0388]

[0389]

[0390] Biological data

[0391] Example A described below shows the induction of defense gene expression in Arabidopsis thaliana by compounds of formula (I), in particular the stimulation of the salicylic acid pathway. Thus, these compounds can induce host defenses, thereby protecting the plant against a variety of pathogens, including bacteria and fungi.

[0392] Examples B and C described below show the direct inactivation of a variety of pathogens, including bacteria and fungi, by compounds of formula (I) in in vitro cell tests, thus illustrating the mode of action of the compounds of formula (I) as inducers of plant host defenses.

[0393] Examples D, E, F and G described below show the in vivo activity of compounds of formula (I) in plants by stimulating the plant defenses against a variety of pathogens, including bacteria and fungi, which infest the plants.

[0394] Examples H, I and J described below show the in vivo activity in plants of a comparative compound CMP1 and the compounds of the present application, which were prepared according to the teachings of WO 2004 / 062361. The comparative compound CMP1 differs from the compounds of the present application in that R 3 is hydrogen, while R 1 and R 2 are both halogen (bromine). The activity of CMP1 is compared with the activity of the compounds of the present application, which shows that the activity of this prior art compound is significantly lower and thus does not provide the beneficial technical effect of the compounds of the present application.

[0395] Example A: Induction of defense gene expression in Arabidopsis thaliana

[0396] Arabidopsis thaliana reporter plants containing a green fluorescent protein (GFP) coding sequence linked to the salicylate-responsive promoter sequence of the PR1 (pathogenesis-related protein 1) gene (AT2G14610) were grown for 5 days and then sprayed with the compounds. On day 3 after the spray, the plants were evaluated for fluorescence using a MacroFluo instrument from Leica Microsystems (Wetzlar, Germany). Fluorescence was quantified using Meta-Morph microscope automation and image analysis software (Molecular Devices, Sunnyvale, CA, United States).

[0397] The background fluorescence of mock-treated leaves was set to 1.00. The relative fluorescence value obtained for salicylic acid treatment (300 ppm) was 2.70, thus proving the effectiveness of the test system.

[0398] In this test, the following compounds of the present application showed a relative fluorescence value of at least greater than 2 at a compound concentration of 300 ppm: I.01; I.02; I.03; I.04; I.06; I.07; I.08; I.09; I.12; I.15; I.16; I.17.

[0399] In this test, the following compounds of the present application showed a relative fluorescence value of at least greater than 2 at a compound concentration of 75 ppm: I.02; I.06; I.07; I.08; I.09; I.11; I.16; I.17.

[0400] Salicylates are major defense hormones against plant pathogens. All of the above compounds stimulate the salicylic acid pathway and therefore protect plants against a variety of pathogens.

[0401] Example B: In vitro cell test of Colletotrichum lindemuthianum

[0402] Solvent: DMSO

[0403] Medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated yeast extract (Merck), 1 liter QSP

[0404] Inoculum: Spore suspension

[0405] Fungicides were dissolved in DMSO and the solutions were used to prepare the desired concentration range. The final concentration of DMSO used in the test was < 1%.

[0406] Preparation of spore suspension and dilution to the desired spore density.

[0407] In liquid culture tests, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. Compounds were added to the medium containing spores at the desired concentration. After 6 days of incubation, the fungitoxicity of the compounds was determined by measuring mycelial growth spectrophotometrically. Inhibition of fungal growth was determined by comparing the absorbance values in the wells containing fungicide to the absorbance values in control wells containing no fungicide. Colletotrichum lindemuthianum

[0408] In liquid culture tests, the ability of fungicides to inhibit spore germination and mycelial growth was evaluated. Compounds were added to the medium containing spores at the desired concentration. After 6 days of incubation, the fungitoxicity of the compounds was determined by measuring mycelial growth spectrophotometrically. Inhibition of fungal growth was determined by comparing the absorbance values in the wells containing fungicide to the absorbance values in control wells containing no fungicide.

[0409] ​In this test, the following compounds of the application did not show direct activity (efficacy lower than or equal to 30%) at a concentration of active ingredient of 20 ppm: I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.14; I.15; I.16; I.17; I.19; I.20; I.21; I.22; I.23; I.24; I.25.

[0410] Example C: In vitro cell test of Xanthomonas campestris pv. campestris Example D: In vivo preventive test of Colletotrichum lindemuthianum (Bean

[0411] Solvent: DMSO

[0412] Culture medium: LB Broth medium (Luria Broth Miller) Sigma

[0413] Inoculum: bacterial suspension

[0414] The compounds were dissolved in DMSO and the solutions were used to prepare the desired concentration range. The final concentration of DMSO used in the test was < 1%.

[0415] The inoculum was prepared from a bacterial pre-culture grown in liquid medium and it was diluted to the desired optical density (OD).

[0416] The ability of the compounds to inhibit bacterial growth was evaluated in a liquid culture test. The compounds were added to the medium containing the bacterial suspension at the desired concentration. After 24 hours of incubation, the efficacy of the compounds was determined by measuring the bacterial growth spectrometrically. The inhibition was determined by comparing the absorbance values in the wells containing the compounds with the absorbance values in the control wells containing no active ingredient.

[0417] In this test, the following compounds of the application did not show direct activity (efficacy lower than or equal to 30%) at a concentration of active ingredient of 20 ppm: I.01; I.02; I.03; I.04; I.05; I.06; I.07; I.08; I.09; I.11; I.12; I.13; I.14; I.15; I.16; I.17; I.19; I.20; I.21; I.22; I.23; I.24; I.25.

[0418] Antrachnose) Example E: In vivo preventive test of Peronospora parasitica (Crucifer downy

[0419] The active ingredient tested was prepared by homogenization in a mixture of acetone / dimethyl sulfoxide (9:1) and then diluted with water to obtain the desired active substance concentration.

[0420] ​The active ingredients prepared as described above are used to treat bean seedlings by spraying. The control plants are treated with an aqueous solution of acetone / dimethyl sulfoxide only.

[0421] After 72 hours, the plants are infected by spraying the leaves with an aqueous suspension of the spores of Phoma exigua var. fumosa. The infected bean plants are incubated for 24 hours at 20°C and 100% relative humidity and then for 5 days at 20°C and 90% relative humidity.

[0422] The test is evaluated 6 days after inoculation. 0% means efficacy corresponding to the control plants, while an efficacy of 100% means that no disease is observed.

[0423] In this test, the following compounds according to the application show an efficacy of 70% to 79% at an active ingredient concentration of 500 ppm: I.26.

[0424] In this test, the following compounds according to the application show an efficacy of 80% to 89% at an active ingredient concentration of 500 ppm: I.07; I.12.

[0425] In this test, the following compounds according to the application show an efficacy of 90% to 100% at an active ingredient concentration of 500 ppm: I.06; I.08; I.09; I.11 ; I.13.

[0426] In this test, the following compounds according to the application show an efficacy of 70% to 79% at an active ingredient concentration of 31 ppm: I.09; I.25.

[0427] In this test, the following compounds according to the application show an efficacy of 80% to 89% at an active ingredient concentration of 31 ppm: I.22.

[0428] mildew) Example F: In vivo preventive test of Xanthomonas campestris pv. campestris

[0429] The active ingredients tested are prepared by homogenization in a mixture of acetone / dimethyl sulfoxide and then diluted with water to obtain the desired active substance concentration.

[0430] The active ingredients prepared as described above are used to treat cabbage seedlings by spraying. The control plants are treated with an aqueous solution of acetone / dimethyl sulfoxide only.

[0431] After 72 hours, the plants are infected by spraying the leaves with an aqueous suspension of the spores of Peronospora parasitica. The infected cabbage plants are incubated for 5 days at 20°C and 100% relative humidity.

[0432] The test is evaluated 5 days after inoculation. 0% means efficacy comparable to the control plants, whereas 100% efficacy means that no disease was observed.

[0433] In this test the following compounds according to the present application showed 70 to 79% efficacy at the active ingredient concentration of 31 ppm: I.03; I.09; I.11 ; I.12; I.26.

[0434] In this test the following compounds according to the present application showed 90 to 100% efficacy at the active ingredient concentration of 31 ppm: I.06; I.13.

[0435] (cabbage black rot) Example G: In vivo preventive test of Uromyces appendiculatus (Bean rust)

[0436] The active ingredients tested are prepared by homogenization in a mixture of acetone / dimethyl sulfoxide / and then diluted with water to obtain the desired active substance concentration.

[0437] The brassica seedlings are treated by spraying with the active ingredients prepared as described above. The control plants are treated with an aqueous solution of acetone / dimethyl sulfoxide / only.

[0438] After 72 hours the plants are infected by spraying the leaves with an aqueous bacterial suspension of Xanthomonas campestris p. v. campestris. The infected brassica plants are incubated for 8 or 10 days at 27°C and 95% relative humidity.

[0439] The test is evaluated 8 or 10 days after inoculation. 0% means efficacy comparable to the control plants, whereas 100% efficacy means that no disease was observed.

[0440] In this test the following compounds according to the present application showed 70 to 79% efficacy at the active ingredient concentration of 31 ppm: I.03; I.09; I.11 ; I.12; I.26.

[0441] In this test the following compounds according to the present application showed 80 to 89% efficacy at the active ingredient concentration of 31 ppm: I.01 ; I.08.

[0442] In this test the following compounds according to the present application showed 90 to 100% efficacy at the active ingredient concentration of 31 ppm: I.06; I.13.

[0443] In this test the following compounds according to the application showed an efficacy of 70 to 79 % at the active ingredient concentration of 125 ppm: I.03; I.08; I.15.

[0444] In this test the following compounds according to the application showed an efficacy of 80 to 89 % at the active ingredient concentration of 125 ppm: I.02; I.13.

[0445] In this test the following compounds according to the application showed an efficacy of 90 to 100 % at the active ingredient concentration of 125 ppm: I.06; I.11 ; I.12.

[0446] Example H: Comparative example Xanthomonas campestris pv. campestris (cabbage black

[0447] The active ingredients tested were prepared by homogenization in a mixture of acetone / dimethyl sulfoxide (9:1 ) and then diluted with water to obtain the desired active substance concentration. The plants were treated by spraying with the active ingredients prepared as described above. The control plants were treated with an aqueous solution of acetone / dimethyl sulfoxide (9:1 ) only.

[0448]

[0449] 72 hours later, the plants were infected by spraying the leaves with an aqueous suspension of Puccinia hordei spores. The infected bean plants were incubated for 24 hours at 20°C and 100 % relative humidity and then for 9 days at 20°C and 70-80 % relative humidity.

[0450] The test was evaluated 10 days after inoculation. 0 % means the efficacy of the control plants, whereas an efficacy of 100 % means that no disease was observed.

[0451] In this test the following compounds according to the application showed an efficacy of 70 to 79 % at the active ingredient concentration of 500 ppm: I.02.

[0452] In this test the following compounds according to the application showed an efficacy of 80 to 89 % at the active ingredient concentration of 500 ppm: I.15.

[0453] In this test the following compounds according to the application showed an efficacy of 90 to 100 % at the active ingredient concentration of 500 ppm: I.01 ; I.04; I.05; I.06; I.07; I.08; I.09; I.11 ; I.12; I.13; I.26.

[0454] In this test the following compounds according to the application showed an efficacy of 70 to 79 % at the active ingredient concentration of 31 ppm: I.06; I.23.​​

[0455] In this test, the following compounds of the application showed an efficacy of 80 to 89% at an active ingredient concentration of 31 ppm: I.11 ; I.20.

[0456] In this test, the following compounds of the application showed an efficacy of 90 to 100% at an active ingredient concentration of 31 ppm: I.08; I.09; I.16; I.19; I.21 ; I.22; I.25.

[0457] In this test, the following compounds of the application showed an efficacy of 70 to 79% at an active ingredient concentration of 125 ppm: I.06; I.20.

[0458] In this test, the following compounds of the application showed an efficacy of 90 to 100% at an active ingredient concentration of 125 ppm: I.08; I.09; I.11 ; I.12; I.13; I.16; I.17; I.19; I.21 ; I.22; I.24; I.25.

[0459] rot)

[0460] Compound CMP1 was tested in an in vivo prophylactic test under the same conditions as described for Example F. Example I: Comparative example Example J: Comparative example Compound CMP1 was tested in an in vivo prophylactic test under the same conditions as described for Example F.

[0461] Compound CMP1 was prepared according to the teachings of WO 2004 / 062361.

[0462] The results are shown in the following table.

[0463]

[0464] * arithmetic mean of 4 tests

[0465] The following compounds of the application of formula (I) show a better efficacy than the structurally related compound CMP1 in the table below.

[0466]

[0467] The following compounds of the application of formula (I) show a better efficacy than the structurally related compound CMP1 when tested at a concentration of 125 ppm.

[0468] More specifically, at a concentration of 125 ppm, compounds I.03, I.08, I.15 show an efficacy of 70% to 79%, compounds I.02, I.13 show an efficacy of 80% to 89%, and compounds I.06, I.11, I.12 show an efficacy of 90% to 100%, whereas CMP1 shows an efficacy of less than 40% at the same concentration.

[0469] When tested at a concentration of 31 ppm, the compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1.

[0470] More specifically, at a concentration of 31 ppm, compounds I.03, I.09, I.11, I.12, I.26 show an efficacy of 70% to 79%, compounds I.01, I.08 show an efficacy of 80% to 89%, and compounds I.06, I.13 show an efficacy of 90% to 100%, whereas CMP1 shows an efficacy of less than 40% at the same concentration.

[0471] Colletotrichum lindemuthianum (Bean

[0472] Compound CMP1 was tested in an in vivo prophylactic test on Puccinia recondita f. sp. tritici (brown rust) under the same conditions as described in example G.

[0473] Compound CMP1 was prepared according to the teachings of WO 2004 / 062361.

[0474] The results are shown in the following table.

[0475]

[0476] * arithmetic mean of 3 tests

[0477] The compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1 in the following table.

[0478]

[0479]

[0480] When tested at a concentration of 31 ppm, the compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1.

[0481] More specifically, at a concentration of 125 ppm, compounds I.06, I.20 show an efficacy of 70% to 79%, and compounds I.08, I.09, I.11, I.12, I.13, I.16, I.17, I.19, I.21, I.22, I.24, I.25 show an efficacy of 90% to 100%, whereas CMP1 shows an efficacy of less than 42% at the same concentration.

[0482] When tested at a concentration of 31 ppm, the compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1.

[0483] More specifically, at a concentration of 31 ppm, compounds I.06, I.23 show an efficacy of 70% to 79%, compounds I.11, I.20 show an efficacy of 80% to 89%, and compounds I.08, I.09, I.16, I.19, I.21, I.22, I.25 show an efficacy of 90% to 100%, whereas CMP1 shows an efficacy of less than 40% at the same concentration.

[0484] Antrachnose)

[0485] The compound CMP1 was tested in an in vivo prophylactic test under the same conditions as described in Example D. ​ The compound CMP1 was tested in an in vivo prophylactic test under the same conditions as described in Example D.

[0486] The compound CMP1 was prepared according to the teachings of WO 2004 / 062361.

[0487] The results are shown in the following table.

[0488]

[0489] The compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1 in the following table.

[0490]

[0491] When tested at a concentration of 31 ppm, the compounds of formula (I) of the present application show a better efficacy than the structurally related compound CMP1.

[0492] More specifically, at a concentration of 31 ppm, compounds I.09, I.25 show an efficacy of 70% to 79%, and compound I.22 shows an efficacy of 90% to 100%, whereas CMP1 shows an efficacy of less than 20% at the same concentration.

Claims

1. A compound of formula (I): ###0001### wherein W is selected from oxygen and sulfur; R 1 selected from trifluoromethyl or cyano; R 2 selected from fluorine, chlorine or bromine; R 3 is hydrogen; Y is oxygen; and 2. The compound according to claim 1 : ###0002### wherein W is selected from oxygen and sulfur; R 4 and R 5 are independently selected from the group consisting of methyl, ethyl, n-propyl and i-propyl, or R 4 and R 5 form together with the carbon atom to which they are attached a cyclopropyl or a cyclobutyl group. Y is oxygen; and 3. The compound according to claim 1 : ###0003### wherein R 1 selected from trifluoromethyl and cyano; R 2 selected from fluorine, chlorine and bromine; R 3 is hydrogen; W is selected from oxygen and sulfur; Y is oxygen; and 4. The compound is selected from ###0004### R 4 and R 5 is independently selected from the group consisting of methyl, ethyl, n-propyl and i-propyl.

5. A composition comprising at least one compound according to any one of claims 1 to 4 and at least one agriculturally suitable auxiliary.

6. The use of a compound according to any one of claims 1 to 4 or of a composition according to claim 5 for controlling fungal diseases on plants or plant parts. R 1 selected from trifluoromethyl and cyano; R 2 selected from fluorine, chlorine and bromine; R 3 is hydrogen; ​ ​ ​ R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl or cyclobutyl group. ​ ​ ​

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