BR112019020739B1 - COMPOUNDS DERIVED FROM OXADIAZOLE MICROBIOCIDES AND THEIR USE, AGROCHEMICAL COMPOSITION, METHOD TO CONTROL OR PREVENT INFESTATION OF USEFUL PLANTS BY PHYTOPATHOGENIC MICROORGANISMS - Google Patents

Abstract

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

Description

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

[0002] Certain oxadiazole derivatives are known as insecticidal and acaricidal agents, e.g. e.g., from document CN 1927860. Documents WO 2013/064079, EP 0 276 432 and WO 2015/185485 describe the use of substituted oxadiazoles to combat phytopathogenic fungi.

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

[0004] where

[0005] A is:

[0006] R1 and R2 are hydrogen; wherein (i) R3 is R3a, wherein R3a is methoxy;

[0007] R4 is R4a, where R4a is propyl, isopropyl, butyl, isobutyl, sec-butyl, C3-4alkenyl or C1-2fluoroalkyl;

[0008] R5 is R5a, where R5a is cyano, C3-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-3alkyl, hydroxyC1-3alkyl, C1-2alkoxyC1-3alkyl, C1-2haloalkoxyC1 -3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl, or

[0009] R5a is C3-4cycloalkyl or C3-4cycloalkyl C1-2alkyl, wherein the cycloalkyl chemical moiety is, optionally, partially unsaturated, heterocyclyl or heterocyclyl C1-2alkyl, wherein the heterocyclyl chemical moiety is a non- 4 to 6 membered aromatic compound comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5a, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be equal or different, selected from R6, where R6 is R6a;

[0010] R6a represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5a comprises a C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or

[0011] (ii) R3 is R3b, where R3b is methoxy;

[0012] R4 is R4b, where R4b is ethyl, C3-4alkynyl or cyanomethyl; It is

[0013] R5 is R5b, where R5b is C1-3fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-3alkyl, C1-2alkoxyC1-3alkyl, hydroxyC1-3alkyl, C1-2haloalkoxyC1-3alkyl, aminoC1-3alkyl , N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or

[0014] R5b is cyclobutyl, C3-4cycloalkylethyl, in which the cycloalkyl chemical moiety is optionally partially unsaturated, heterocyclyl or C1-2alkyl heterocyclyl, in which the heterocyclyl chemical moiety is a 4 to 6 non-aromatic ring members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6b;

[0015] R6b represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5b comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or

[0016] (iii) R3 is R3c, where R3c is methoxy;

[0017] R4 is R4c, where R4c is C1-4alkoxy; It is

[0018] R5 is R5c, where R5c is C2-5alkyl, C1-3fluoroalkyl,C3-4alkenyl, C3-4alkynyl, cyano C1-3alkyl, C3-4haloalkenyl, hydroxyC1-3alkyl, C1-2alkoxyC1-3alkyl, C1-2fluoroalkoxyC2- 3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or

[0019] R5c is C3-4cycloalkyl or C3-4cycloalkylC1-2alkyl, in which the cycloalkyl chemical moiety is, optionally, partially unsaturated, heterocyclyl or heterocyclylC1-2alkyl, in which the heterocyclyl chemical moiety is a non-aromatic ring of 4 to 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c;

[0020] R6c represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5c comprises a C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or

[0021] (iv) R3 is R3d, where R3d is methyl or ethyl;

[0022] R4 is R4d, where R4d is cyano, C3-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C2-4alkoxy or C1-2alkoxy-3alkyl; It is

[0023] R5 is R5d, where R5d is C2-5alkyl, C3-5alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C1-3fluoroalkyl, C3-4haloalkenyl, hydroxyC1-3alkyl, C1-2alkoxymethyl, C1-2alkoxyC3alkyl Ci-2fluoroalkoxyCi- 3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or

[0024] R5d is C3-4cycloalkyl or C3-4cycloalkylC2alkyl, in which the cycloalkyl chemical moiety is, optionally, partially unsaturated, heterocyclyl or heterocyclyl C1-2alkyl, in which the heterocyclyl chemical moiety is a non-aromatic ring of 4 to 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different , selected from R6, where R6 is R6d;

[0025] R6d represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5d comprises a C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or

[0026] with R3 as defined for each of modalities (i), (ii), (iii) and (iv), R4 and R5, together with the nitrogen atom to which they are attached, form a selected cycle from 3-oxo-pyrrolidinyl, 2-oxo-pyrrolidinyl, azetidinyl, oxazolidinyl, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethanone;

[0027] or

[0028] a salt or N-oxide thereof.

[0029] Surprisingly, it was discovered that the new compounds of Formula (I) have, for practical purposes, a very advantageous level of biological activity for the protection of plants against diseases that are caused by fungi.

[0030] According to a second aspect of the invention, there is provided an agrochemical composition comprising a fungicidal effective amount of a compound of Formula (I). Such an agricultural composition may further comprise at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier.

[0031] According to a third aspect of the invention, there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, in which a fungicidal effective amount of a compound of Formula (I) or a composition that comprises this compound as an active ingredient and is applied to plants, their parts or their locus.

[0032] According to a fourth aspect of the invention, the use of a compound of Formula (I) as a fungicide is provided. According to this particular aspect of the invention, use may exclude methods for treating the human or animal body by surgery or therapy.

[0033] As used herein, the term “halogen” or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromine) or iodine (iodine), preferably fluorine, chlorine or bromine.

[0034] As used herein, cyan means a -CN group.

[0035] As used herein, the term “hydroxyl” or “hydroxy” means an -OH group.

[0036] As used herein, amino designates a -NH2 group.

[0037] As used herein, the term “C1-4 alkyl” refers to a straight or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, containing no unsaturation, having from one to four carbon atoms, and which is attached to the rest of the molecule by a single bond. C1-3alkyl and C1-2alkyl should be interpreted accordingly. Examples of C1-4alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (t-butyl). A “C1-2alkylene” group refers to the corresponding definition of C1-2alkyl, except that such a radical is attached to the remainder of the molecule by two single bonds. Examples of C1-2alkylene are -CH2- and -CH2CH2-.

[0038] As used herein, the term “C1-4alkoxy” refers to a radical of formula -ORx, where Rx is a C1-4alkyl radical as generally defined above. The terms C1-3alkoxy and C1-2alkoxy should be interpreted accordingly. Examples of C1-4alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and t-butoxy.

[0039] As used herein, the term “C1-2fluoroalkyl” refers to a C1-2alkyl radical as generally defined above substituted by one or more fluorine atoms. Examples of C1-3fluoroalkyl include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.

[0040] As used herein, the term “C3-4alkenyl” refers to a straight or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one double bond that may be of the (E)- or (Z)- configuration, having three or four carbon atoms, which are fixed to the rest of the molecule by a single bond. Examples of C3-4alkenyl include, but are not limited to, prop-1-enyl, allyl and but-1-enyl.

[0041] As used herein, the term “C3-4haloalkenyl” refers to a C3-46alkenyl radical as generally defined above substituted by one or more of the same or different halogen atoms.

[0042] As used herein, the term “C3-4alkynyl” refers to a straight or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one triple bond, which has three or four carbon atoms, and which is fixed to the rest of the molecule by a single bond. Examples of C3-4alkynyl include, but are not limited to, prop-1-ynyl, propargyl.

[0043] As used herein, the term “C1-2alkoxyC1-3alkyl” refers to the radical of the formula Ry-O-Rx- wherein Ry is a C1-2alkyl radical as generally defined above, and Rx is a radical of C1-3alkylene as generally defined above.

[0044] As used herein, the term “hydroxyC1-3alkyl” refers to a C1-3alkyl radical as generally defined above substituted by one or more hydroxy groups. The term “hydroxyC1-2alkyl” should be considered accordingly. (i) As used herein, the term “cyanoC1-3alkyl” refers to a C1-3alkyl radical as generally defined above substituted by one or more cyano groups.

[0045] As used herein, the term “C1-3alkylamino” refers to a -HNRx radical wherein Rx is a C1-3alkyl radical as generally defined above.

[0046] As used herein, the term “N,N-diC1-3alkylamino” refers to a -N(Rx)2 radical in which Rx is the same as or different from the C1-3alkyl radical as generally defined above.

[0047] As used herein, the term “N-C1-3alkylaminoC1-3alkyl” refers to a C1-3alkyl radical as generally defined above substituted by a C1-3alkylamino group as defined above.

[0048] As used herein, the term “N,N-diC1-3alkylaminoC1-3alkyl” refers to a C1-3alkyl radical as generally defined above substituted by an N,N-diC1-3alkylamino group as defined above.

[0049] As used herein, the term “C3-4cycloalkyl” refers to a stable monocyclic ring radical that is saturated or partially unsaturated and contains 3 or 4 carbon atoms. Examples of C3-4cycloalkyl include cyclopropyl, cyclobutyl.

[0050] As used herein, the term “C3-4cycloalkylC1-2alkyl” refers to a C3-4cycloalkyl ring as defined above attached to the remainder of the molecule by a C1-2alkylene radical as defined above. Examples of C3-4cycloalkylC1-2alkyl include, but are not limited to, cyclopropyl-methyl and cyclobutyl-ethyl.

[0051] As used herein, the term “heterocyclyl” or “heterocyclic” generally refers to a stable saturated or partially saturated non-aromatic 4- to 6-membered monocyclic ring, which comprises 1, 2 or 3 heteroatoms individually selected from of nitrogen, oxygen and sulfur. The heterocyclyl radical can be linked to the rest of the molecule through a carbon atom or heteroatom. Examples of heterocyclyls include, but are not limited to, azetidinyl, oxetanyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl and morpholinyl.

[0052] The presence of one or more possible asymmetric carbon atoms in a compound of Formula (I) means that the compounds can occur in chiral isomeric forms, that is, enantiomeric or diastereoisomeric forms. Likewise, atropisomers can also occur as a result of restricted rotation around a single bond. Formula (I) is intended to include all possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of Formula (I). Likewise, Formula (I) is intended to include all possible tautomers (including lactam-lactime tautomerism and keto-enol tautomerism) when present. The present invention includes all possible tautomeric forms for a compound of Formula (I).

[0053] In each case, the compounds of Formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in a covalently hydrated form, or in salt form, for example, in a agronomically usable or agrochemically acceptable salt form.

[0054] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0055] The following list provides definitions, including preferred definitions, for substituents A, R1, R2, R3 (including R3a, R3b, R3c and R3d), R4 (including R4a, R4b, R4c and R4d), R5 (including R5a, R5b , R5c and R5d) and R6 (including R6a, R6b, R6c and R6d), with reference to the compounds of Formula (I) according to the invention. For any of these substituents, any of the definitions provided below may be combined with any definition of any other substituent provided below or elsewhere in this document.

[0056] A is:

[0057] R1 is hydrogen.

[0058] R2 is hydrogen.

[0059] In a certain embodiment of the invention (embodiment (i)), R3 is R3a, where R3a is methoxy; R4 is R4a, where R4a is propyl, isopropyl, butyl, em-butyl, sec-butyl, C3-4alkenyl or C1-2fluoroalkyl; R5 is R5a, where R5a is cyano, C3-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-3alkyl, hydroxyC1-3alkyl, C1-2alkoxyC1-3alkyl, C1-2haloalkoxyC1-3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl, or N,N-diC1-3alkylaminoC1-3alkyl or R5a is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, wherein the cycloalkyl moiety is optionally partially heterocyclyl unsaturated, heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, wherein for R5a, any chemical moiety of cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6a; and R6a represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5a comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group. .

[0060] According to embodiment (i), preferably, R5a is cyano, C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-2alkyl, hydroxyC1-2alkyl, C1-2alkoxyC1 -2alkyl, C1-2haloalkoxyC1-2alkyl, aminoC1-2alkyl, N-C1-2alkylaminoC1-2alkyl or N,N-diC1-2alkylaminoC1-2alkyl, or R5a is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, wherein the chemical moiety of cycloalkyl is optionally partially unsaturated heterocyclyl, heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, in that, for R5a, any cycloalkyl or heterocyclyl chemical moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6a.

[0061] More preferably R5a is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl, or R5a is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1 - 2alkyl, wherein the heterocyclyl moiety is a 4 to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein for R5a, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6a.

[0062] Even more preferably, R5a is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl or R5a is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein a heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein, for R5a, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6a, selected from halogen (in particular, fluorine and chlorine), methyl and ethyl.

[0063] In a certain embodiment of the invention (embodiment (ii)), R3 is R3b, where R3b is methoxy; R4 is R4b, where R4b is ethyl, C3-4alkynyl or cyanomethyl; and R5 is R5b, where R5b is C1-3fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-3alkyl, C1-2alkoxyC1-3alkyl, hydroxyC1-3alkyl, C1-2haloalkoxyC1-3alkyl, aminoC1-3alkyl, N -C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or R5b is cyclobutyl, C3-4cycloalkylethyl, wherein the cycloalkyl moiety is optionally partially unsaturated heterocyclyl, heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 , 2 or 3 heteroatoms individually selected from N, O and S, wherein for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6b; and R6b represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5b comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group. .

[0064] According to embodiment (ii), preferably R5b is C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-2alkyl, hydroxyC1-2alkyl, C1-2alkoxyC1-2alkyl, C1-2haloalkoxyC1-2alkyl , aminoC1-2alkyl, N-C1-2alkylaminoC1-2alkyl or N,N-diC1-2alkylaminoC1-2alkyl or R5b is cyclobutyl, C3-4cycloalkylethyl, heterocyclyl, heterocyclylC1-2alkyl, wherein the heterocyclyl chemical moiety is a non-aromatic ring of 4 to 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6b.

[0065] More preferably, R5b is C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl or R5b is cyclobutyl, C3-4cycloalkylethyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the chemical moiety heterocyclyl is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which they can be the same or different, selected from R6, where R6 is R6b.

[0066] Even more preferably, R5b is C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl, or C1-2alkoxyC1-2alkyl or R5b is cyclobutyl, C3-4cycloalkylethyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents , which may be the same or different, selected from R6, where R6 is R6b, selected from halogen (in particular, fluorine and chlorine), methyl and ethyl.

[0067] In a certain embodiment of the invention (embodiment (iii)), R3 is R3c, where R3c is methoxy; R4 is R4c, where R4c is C1-4alkoxy; and R5 is R5c, where R5c is C2-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-3alkyl, C3-4haloalkenyl, hydroxyC1-3alkyl, C1-2alkoxyC1-3alkyl, C1-2fluoroalkoxyC2-3alkyl, aminoC1 -3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or R5c is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated heterocyclyl, heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4 to 6 non-aromatic ring members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c; and R6c represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5c comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group. .

[0068] According to modality (iii), preferably R4c is methoxy or ethoxy.

[0069] According to embodiment (iii), preferably R5c is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-2alkyl, hydroxyC1-2alkyl, C1-2alkoxyC1-2alkyl, C1-2fluoroalkoxyC1-2alkyl, aminoC1-2alkyl, N-C1-2alkylaminoC1-2alkyl or N,N-diC1-2alkylaminoC1-2alkyl or R5c is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the moiety Heterocyclyl chemistry is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N, O, and S, wherein, for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c.

[0070] More preferably R5c is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl, or R5c is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1 - 2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c.

[0071] Even more preferably, R5c is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl or R5c is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein a heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein, for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c, selected from halogen (in particular, fluorine and chlorine), methyl and ethyl.

[0072] In a certain embodiment of the invention (embodiment (iv)), R3 is R3d, where R3d is methyl or ethyl; R4 is R4d, where R4d is cyano, C3-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C2-4alkoxy or C1-2alkoxyC1-3alkyl; and R5 is R5d, where R5d is C2-5alkyl, C3-5alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C1-3fluoroalkyl, C3-4haloalkenyl, hydroxyC1-3alkyl, C1-2alkoxymethyl, C1-2alkoxyC3alkyl, C1-2fluoroalkoxyC1-3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or

[0073] R5d is C3-4cycloalkyl, C3-4cycloalkylC2alkyl, in which the cycloalkyl chemical moiety is optionally partially unsaturated, heterocyclyl, heterocyclylC1-2alkyl, in which the heterocyclyl chemical moiety is a non-aromatic ring of 4 to 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6d; and R6d represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5d comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group.

[0074] According to modality (iv), preferably, R3d is methyl. Otherwise, it may be preferred that R3d is ethyl.

[0075] According to modality (iv), preferably R4d is cyano, C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C4-5alkynyl, cyanoC1-2alkyl, C2-3alkoxy or C1-2alkoxyC1-2alkyl.

[0076] According to modality (iv), preferably R5d is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, cyanoC1-2alkyl, hydroxyC1-2alkyl, C1-2alkoxymethyl, aminoC1- 2alkyl, N-C1-2alkylaminoC1-2alkyl, or N,N-diC1-2alkylaminoC1-2alkyl or R5d is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl chemical moiety is a non-ring 4- to 6-membered aromatic compound comprising 1 or 2 heteroatoms individually selected from N, O and S, wherein, for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6d.

[0077] More preferably R5d is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxymethyl or R5d is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6d.

[0078] Even more preferably, R5d is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxymethyl or R5d is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1- 2alkyl, wherein a heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein, for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6d, selected from halogen (in particular, fluorine and chlorine), methyl and ethyl.

[0079] Together with R3 as defined for each of modalities (i), (ii), (iii) and (iv), R4 and R5, together with the nitrogen atom to which they are attached, can form a cycle selected from 3-oxo-pyrrolidinyl, 2-oxo-pyrrolidinyl, azetidinyl, oxazolidinyl, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethenone.

[0080] Referentially, the compound according to Formula (I) is selected from a compound 1.1 to 1.3 listed in Table T1 (below).

[0081] It is understood that, when in aqueous media, the compounds of Formula (I) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (i.e., the compounds of Formula (I-Ia ) and Formula (i-IIa) as shown below, which can exist in tautomeric form as the compounds of formula (I-Ib) and formula (i-IIb)) in the CF3-oxadiazole motif. This dynamic balance may be important for the biological activity of compounds of Formula (I). The designations of A, R1, R2, R3 (including R3a, R3b, R3c and R3d), R4 (including R4a, R4b, R4c and R4d), R5 (including R5a, R5b, R5c and R5d) and R6 (including R6a, R6b, R6c and R6d), with reference to the compounds of Formula (I) of the present invention generally apply to the compounds of Formulas (I-Ia), (i-IIa), (I-Ib) and (i-IIb), as well as specific disclosures of combinations of A, R1, R2, R3 (including R3a, R3b, R3c and R3d), R4 (including R4a, R4b, R4c and R4d), R5 (including R5a, R5b, R5c and R5d) and R6 (including R6a, R6b, R6c and R6d), as represented in the compounds described in Tables 1.1 to 1.3 or compounds 1.1 to 1.3 described in Table T1 (below).

[0082] The compounds of the present invention can be prepared as shown in the following schemes 1 to 22, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

[0083] Compounds of formula (I) can be obtained through coupling transformations with compounds of formula (II) and compounds of formula (III), where X is halogen, ester [including OMe or OEt], anhydride [ including OC(H)O or OAc] or OH, preferably halogen, in a suitable solvent (e.g., dimethylformamide, dichloromethane, or tetrahydrofuran), preferably at temperatures between 25 °C and 100 °C, and optionally in the presence of a base (e.g., NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine), or under conditions described in the literature for a urea coupling. For examples, see WO 2003/028729, WO 2013/092943, WO 2017/055473, or WO 2014/025128.

[0084] Furthermore, compounds of formula (I) can be obtained through coupling transformations with compounds of formula (II) and compounds of formula (III), where X is -OH, through processes that convert the -OH in an enhanced halide leaving group, such as a chloride, for example, with the use of triphosgene, diphosgene, phosgene, (COCl)2 or SOCl2, prior to treatment with the compounds of formula (II), optionally in the presence of a base (e.g. NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, Scheme 1

[0085] Alternatively, compounds of formula (I) can be prepared from compounds of formula (II) by reactions with ',1'-carbonyldiimidazole (CDI), triphosgene, diphosgene or phosgene in a suitable solvent (e.g. 1,2-dichloroethane, water, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable amino nucleophiles of formula (IV), in the presence of a suitable base, such as pyridine, K2CO3 or triethylamine, at temperatures between 0 °C and 40 °C. For related examples, see document WO 2017/055473. This reaction is shown in Scheme 2. Scheme 2

[0086] Additionally, compounds of formula (I) can be prepared from compounds of formula (V) by reactions with trifluoroacetic acid, trifluoroacetic ester (including methyl trifluoroacetic ester, ethyl trifluoroacetic ester), trifluoroacetic anhydride or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide) in the presence of a base (e.g. pyridine or 4-dimethylaminopyridine) in a suitable solvent, (e.g. ethyl acetate, tetrahydrofuran, 2-methyltetrahydrofuran or ethanol ), at temperatures between 0 °C and 75 °C. For related examples, see documents WO 2003/028729, WO 2017/055473 and WO 2010/045251. This reaction is shown in Scheme 3. Scheme 3

[0087] Compounds of formula (V) can be prepared from compounds of formula (VI) by reactions with a hydroxylamine hydrochloride salt or a solution of hydroxylamine in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent such as methanol or ethanol, at temperatures between 0 °C and 80 °C. In some cases, better reaction performance may be gained with the use of a catalyst (e.g., 8-hydroxyquinoline). For related examples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268, WO 2017/055473 and WO 2013/06 838. This reaction is shown in Scheme 4. Scheme 4

[0088] Compounds of formula (VI) are commercially available or can be prepared from compounds of formula (VII), where Y is formyl, Cl, Br, or I, through metal-promoted reactions with a reagent of suitable cyanide, such as acetone cyanohydrin, dimethylmalononitrile, K4[Fe(CN)6], Zn(CN)2, NaCN or CuCN, in a suitable solvent (e.g. dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 80 °C and 120 °C, optionally in the presence of a metal catalyst (e.g. Pd or Ni) or a Grignard or organolithium reagent. For related examples, see Reeves, J. T. et al. J. Am. Chem. Soc., (2015), 137, 9481 to 9488, Ushijima, S., Togo, H. Synlett, (2010), 1067, US 2007/0155739, WO 2017/055473 and WO 2009/022746.

[0089] Alternatively, compounds of formula (VI) can be prepared from compounds of formula (VII), where Y is NH2, through nucleophilic aromatic radical substitution reactions in the presence of a nitrite source (e.g. e.g., NaNO2 and iso-amylnitrite), an acid (e.g., hydrochloric acid or HBF4) and a copper source (e.g., CuCN) in an acceptable solvent system, such as aqueous acetonitrile, at suitable temperatures between 0°C to 100°C. °C. For related examples, see Wen, Q. et al. Tet. Lett. (2014), 55, 1271. This reaction is shown in Scheme 5. Scheme 5

[0090] Compounds of formula (VII), in which the N-R3 bond contains a directly linked unsaturated methylene segment [for example, -CH2- or -CH(CH3)-], can be prepared from compounds of formula (VIII), where Y is Cl, Br, I or CN and R4 is other than hydrogen, through base-promoted reactions (e.g. sodium hydride) with the use of a suitable alkylating reagent (e.g. , methyl iodide, ethyl iodide or 2-methoxyethyl iodide or propyl iodide), in a suitable solvent (e.g. dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 60 °C and 120 °C. This reaction is shown in Scheme 6. Scheme 6

[0091] Compounds of formula (II), in which R1 is hydrogen, can be prepared from aldehyde compounds of formula (X), through condensation reactions with compounds of formula (IX), in a suitable solvent , (e.g. tetrahydrofuran or methanol) at a temperature between 25°C and 75°C followed by the addition of a suitable reducing reagent, (e.g. NaBH4, NaBH3CN or LiAlH4), in a suitable solvent (e.g. , tetrahydrofuran or ethanol) at temperatures between 0 °C and 25 °C. For related examples, see Gazzola, C. and Kenyon, GL Journal of Labeled compounds and Radiopharmaceuticals, (1978), 15, 181 and WO 2017/055473. This reaction is shown in Scheme 7. Scheme 7

[0092] Alternatively, compounds of formula (II) can be prepared from compounds of formula (XI), where X is Cl, Br, I, OH or OSO2Me, through substitution reactions with amines of formula ( IX) in a suitable solvent (e.g. tetrahydrofuran) at temperatures between 25 °C and 60 °C. For related examples, see Miyawaki, K. et al Heterocicles (2001), 54, 887, WO 2003/028729, WO 2017/055473 and WO 2013/066839. This reaction is shown in Scheme 8. Scheme 8

[0093] Compounds of formula (XI) can be prepared from compounds of formula (XII), where X is Cl or Br, by reactions with a suitable halogen source [for example, N-bromosuccinimide (NBS ) or N-chlorosuccinimide (NCS)] and a radical initiator [e.g., (PhCO2)2 or azobisisobutyronitrile (AIBN)] in a suitable solvent, such as tetrachloromethane, at temperatures between 55 °C and 100 °C, optionally in the presence of UV light. For related examples, see Liu, S. et al Synthesis (2001), 14, 2078 and Kompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794. This reaction is shown in Scheme 9.

[0094] Compounds of formula (VII) in which Y is halogen or CN can be obtained through coupling transformations with compounds of formula (XIII) and compounds of formula (III), in which X is halogen, ester [including OMe or OEt], anhydride [including OC(H)o or OAc] or OH, preferably halogen, in a suitable solvent (e.g. dimethylformamide, dichloromethane, tetrahydrofuran or 2-methyltetrahydrofuran), preferably at temperatures between 0 °C and 100 °C, and optionally in the presence of a base (for example, NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine) or under conditions described in the literature for a urea coupling.

[0095] Furthermore, compounds of formula (VII) can be obtained through coupling transformations with compounds of formula (XIII) and compounds of formula (III), where X is OH, through processes that convert the -OH in an enhanced halide leaving group, such as a chloride, for example with the use of triphosgene, diphosgene, phosgene, (COCl)2 or SOCl2, prior to treatment with the compounds of formula (XIII). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 10. Scheme 10

[0096] Alternatively, compounds of formula (VII) in which Y is halogen or CN can be prepared from compounds of formula (XIII) through reactions with 1,1'-carbonyldiimidazole (CDI), triphosgene, diphosgene or phosgene in a suitable solvent (e.g. 1,2-dichloroethane, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable nucleophiles of formula (IV) in the presence of a suitable base such as K2CO3, triethylamine . This reaction is shown in Scheme 11. Scheme 11

[0097] Compounds of formula (XIII) in which Y is halogen or CN can be prepared from compounds of formula (XIV), in which X is Cl, Br, I, OH, or OSO2Me, through reactions of condensation with amines of formula (IX) in the presence of a suitable base such as triethylamine, pyridine, NaHCO3, Na2CO3, K2CO3 or NaH, in a suitable solvent such as dimethylformamide, N-methylpyrolidine or acetonitrile, at temperatures between 0 °C and 100 °C W. In some cases, better reaction performance can be obtained from the use of a catalyst (e.g. Bu4NHSO4, Bu4NBr, Bu4NI, NaI or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887. This reaction is shown in Scheme 12. Scheme 12

[0098] Compounds of formula (XIV), where Y is halogen or CN and X is Cl or Br, are commercially available or can be prepared from compounds of formula (XV) through treatment with a halogen source , (e.g. N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator, such as (PhCO2)2 or azobisisobutyronitrile (AIBN), in the presence of ultraviolet light, in a suitable solvent, such as tetrachloromethane, to temperatures between 55 °C and 100 °C. For related examples, see Liu, S. et al Syntheis (2001), 14, 2078 and Kompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794. Compounds of formula (XV) are commercially available. This reaction is shown in Scheme 13. Scheme 13

[0099] Alternatively, compounds of formula (XIV), where X is Cl, Br, I or OSO2Me and Y is halogen or CN are commercially available or can be prepared from compounds of formula (XVI), by means of reactions with a suitable acid source (e.g. hydrochloric acid, hydrobromic acid, or hydriodic acid) or a suitable halogen source (e.g. tetrabromomethane, tetrachloromethane or iodine), optionally in the presence of triphenylphosphine, or with methanesulfonyl chloride ( ClSO2Me), in a suitable solvent, (e.g. dichloromethane) at temperatures between 0 °C and 100 °C. For related examples, see Liu, H. et al Bioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A. et al Bioorg. Med. Chem. Lett. (2001), 1, 3161. Compounds of formula (XVI) are commercially available. This reaction is shown in Scheme 14. Scheme 14

[0100] Furthermore, compounds of formula (VII) in which Y is halogen or CN can be prepared from compounds of formula (XIV), in which X is Cl, Br, I or OSO2Me and Y is halogen or CN, by reactions with ureas of formula (XVII) in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine, K2CO3, NaHCO3, or Na2CO3) in a suitable solvent (e.g., dimethylacetamide, tetrahydrofuran , 2-methyltetrahydrofuran, acetone or acetonitrile) at temperatures between 0 °C and 90 °C. In some cases, better reaction performance can be obtained from the use of a catalyst (e.g. Bu4NHSO4, Bu4NBr, Bu4NI, NaI or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887, WO 2003/028729 and WO 2013/066839. This reaction is shown in Scheme 15. Scheme 15

[0101] Compounds of formula (XVII) can be prepared from amine compounds of formula (IX) through reactions with 1,1'-carbonyldiimidazole (CDI), triphosgene, diphosgene or phosgene, optionally in a suitable solvent (e.g. water, acetonitrile, ethyl acetate, tetrahydrofuran, chloroform or toluene) followed by the addition of suitable amines of formula (IV), optionally in the presence of a base (e.g. pyridine, triethylamine, K2CO3, NaHCO3, Na2CO3), and at temperatures between 0 °C and 25 °C. This reaction is shown in Scheme 16. Scheme 16

[0102] Alternatively, compounds of formula (XVII) can be obtained through coupling transformations with amine compounds of formula (IX) and compounds of formula (III), wherein X is halogen, ester [including OMe or OEt], anhydride [including OC(H)o or OAc] or OH, preferably halogen, in a suitable solvent (e.g. dimethylformamide, acetonitrile, dichloromethane or tetrahydrofuran), preferably at temperatures between 25 °C and 100 °C, and optionally in the presence of a base (e.g., K2CO3, triethylamine or N,N-diisopropylethylamine), or under conditions described in the literature for a urea coupling. For examples, see WO 2003/028729.

[0103] Furthermore, compounds of formula (XVII) can be obtained through coupling transformation with compounds of formula (IX) and compounds of formula (III), where X is OH, through processes that convert the -OH in an enhanced halide leaving group, such as a chloride, for example with the use of triphosgene, phosgene, (COCl)2 or SOCl2, prior to treatment with the compounds of formula (IX). Compounds of formula (III) and formula (IX) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 17. Scheme 17

[0104] Furthermore, compounds of formula (I) can be prepared from compounds of formula (XI), where X is halogen, OH or OSO2Me, through reactions with ureas of formula (XVII), optionally in the presence of a base (e.g. triethylamine, N,N-diisopropylethylamine, K2CO3, NaHCO3 or Na2CO3) in a suitable solvent (e.g. dimethylacetamide, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, toluene or acetonitrile), at temperatures between 0 °C and 90 °C. In some cases, better reaction performance can be obtained from the use of a catalyst (e.g. Bu4NHSO4, Bu4NBr, Bu4NI, NaI or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887, WO 2003/028729 and WO 2013/066839. This reaction is shown in Scheme 18. Scheme 18

[0105] Alternatively, compounds of Formula (XI) in which X is hydrogen, OH, OSO2Me, Cl, Br or I can be prepared from compounds of Formula (XVIII) through reactions with trifluoroacetic acid, trifluoroacetic ester ( including methyl trifluoroacetic ester and ethyl trifluoroacetic ester), trifluoroacetic anhydride or trifluoroacetyl trifluoroacetyl halide, trifluoroacetyl chloride and trifluoroacetyl bromide) in the presence of a base (e.g. pyridine or 4-dimethylaminopyridine) in a suitable solvent, (e.g. ethyl acetate , tetrahydrofuran, 2-methyltetrahydrofuran or ethanol), at temperatures between 0 °C and 75 °C. For related examples, see WO 2003/028729, WO 2017/055473 and WO 2010/045251. This reaction is shown in Scheme 19. Scheme 19

[0106] Compounds of Formula (XVIII) in which X is hydrogen OH, OSO2Me, Cl, Br or I can be prepared from compounds of Formula (XIX), through reactions with a hydroxylamine hydrochloric salt or a solution of hydroxylamine in water, in the presence of a base such as triethylamine or potassium carbonate, in a suitable solvent such as methanol or ethanol, at temperatures between 0 °C and 80 °C. In some cases, better reaction performance can be obtained from the use of a catalyst (e.g., 8-hydroxyquinoline). For related examples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268, WO 2017/055473 and WO 2013/066838. This reaction is shown in Scheme 20. Scheme 20

[0107] Compounds of Formula (XIX) in which X is hydrogen, OH, OSO2Me, Cl, Br or I can be prepared from compounds of Formula (XIV), in which Y is halogen, through reactions promoted by metal with a suitable cyanide reagent such as Pd(0)/Zn(CN)2 or CuCN in a suitable solvent (e.g. dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 100 °C and 120 °C. For related examples, see US 2007/0155739 and WO 2009/022746. This reaction is shown in Scheme 21. Scheme 21

[0108] The compounds of Formula (XIV) in which X is Cl, Br, I or OSO2Me and Y is halogen or CN are commercially available or can be prepared from the compounds of Formula (XX), in which Y is halogen or CN, through reactions with a suitable acid source (e.g. hydrochloric acid, hydrobromic acid or hydriodic acid) or with a suitable halogen source (e.g. CCl3Br, CCl4 or I2) in the presence of triphenylphosphine or with methanesulfonyl (ClSO2Me), in a suitable solvent, (e.g. dichloromethane) at temperatures between 0 °C and 100 °C. For related examples, see Liu, H. et al Bioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A. et al Bioorg. Med. Chem. lLett. (2001), 1, 3161. Compounds of formula (XX) are commercially available or prepared using known methods. This reaction is shown in Scheme 22. Scheme 22

[0109] As already indicated, surprisingly, it has now been found that the compounds of Formula (I) of the present invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0110] The compounds of formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for the control of plant pests or in non-living materials for the control of microorganisms that cause spoilage or organisms potentially harmful to humans. The new compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants and by being safe from an environmental point of view. They have very useful curative, preventive and systemic properties and can be used for the protection of various cultivated plants. Compounds of Formula (I) can be used to inhibit or destroy pests occurring on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of different useful plant crops, while also protecting those parts of plants that grow later, for example, from phytopathogenic microorganisms. (i) The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack, by treatment of plants or plant propagation material and/or harvested food crops, wherein an effective amount of a compound of Formula (I) is applied to the plants, their parts or their locus.

[0111] It is also possible to use compounds of formula (I) as a fungicide. The term “fungicide”, as used herein, means a compound that controls, modifies or prevents the growth of fungi. The term "fungicidal effective amount", where used, means the amount of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural development, such as death, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.

[0112] It may also be possible to use compounds of Formula (I) as curative agents for treating plant propagation material, e.g. seeds, such as fruits, tubers or grains, or plant cuttings, for protection against fungal infections, as well as against phytopathogenic fungi that occur in the soil. The propagation material can be treated with a composition comprising a compound of Formula (I) before planting: the seed, for example, can be filmed before being sown. The active compounds of Formula (I) can also be applied to grains (coating), by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example, to the seedbed during sowing. The invention further relates to such methods for treating plant propagation material and the plant propagation material so treated.

[0113] Additionally, compounds of Formula (I) can be used to control fungi in related areas, for example, in the protection of technical materials, including wood and wood-related technical products, in food storage, in hygiene management.

[0114] Additionally, the invention could be used to protect non-living materials from fungal attack, for example, construction wood, wall panels and paint.

[0115] The compounds of Formula (I) are, for example, effective against fungi and fungal vectors of disease, as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease, as well as phytopathogenic bacteria and viruses are, for example:

[0116] Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. includes econdyinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Clav39ecônditrpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii , Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phom40ecônditticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedi40ecônditticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. horde40econditaondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp,. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

[0117] The compounds of Formula (I) can be used, for example, in peat, ornamentals, such as flowers, shrubs, broad-leaved or evergreen trees, e.g. conifers, as well as for tree injection, pest management and similar.

[0118] Within the scope of the present invention, the targeted useful crops and/or plants to be protected typically comprise perennial or annual crops, such as berry plants, for example, blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example, barley, corn, millet, oats, rice, rye, sorghum triticale and wheat; fiber plants, e.g. cotton, flax, hemp, jute and sisal; agricultural crops, for example, sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppi, sugar cane, sunflower, tea and tobacco; fruit trees, e.g. apple, apricot, avocado, banana, cherry, citrus fruit, nectarine, peach, pear and plum; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, rye grass, Sto grass. Augustine and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes, for example beans, lentils, peas and soya; nuts, for example, almonds, cashews, crushed walnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms, e.g. palm oil; ornamentations, for example, flowers, shrubs and trees; other trees, e.g. cocoa, coconut, olive and rubber; vegetables, for example, asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vineyards, e.g. grapes.

[0119] The term "useful plants" should be understood to further include useful plants that have been made tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, e.g. primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors) as a result of conventional breeding methods or genetic modification. An example of a crop that has been made tolerant to imidazolinones, e.g. imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (Canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic modification methods include glyphosate- and glufosinate-resistant corn varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0120] The term "useful plants" should be understood as further including useful plants that have thus been transformed by the use of recombinant DNA techniques that are capable of synthesizing one or more selectively acting toxins, as they are known, for example, from toxin-producing bacteria, especially those of the Bacillus genus.

[0121] Examples of such plants are: YieldGard® (maize variety that expresses a CryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses a CryIA(b) toxin and a CryIIIB(b1) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); Bollgard I® (cotton variety that expresses a CryIA(c) toxin); Bollgard II® (cotton variety that expresses a CryIA(c) toxin and a CryIIA(b) toxin); VIPCOT® (a cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerant trait), Agrisure® CB Advantage (Bt11 (CB) corn bora trait), Agrisure® RW (corn rootworm trait) and Protecta®.

[0122] The term “crops” is to be understood as also including crop plants that have been transformed in such a way by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known e.g. of toxin-producing bacteria, especially those of the Bacillus genus.

[0123] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from bacterial colonizing nematodes, e.g., Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycete toxins; plant lectins, such as pea lectins, barley lectins or amaryllide lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivation proteins (RIP), such as ricin, corn RIP, abren, lufin, saporin or bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyltransferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA reductase, ion channel blockers such as sodium or calcium channel blockers, hormone esterase juvenile, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0124] Furthermore, in the context of the present invention, they should be understood as δ-endotoxins, for example CrylAb, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of these proteins (see, for example, WO 02/15701). Truncated toxins are known, for example a truncated Cry1Ab. In the case of engineered toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03/018810 ).

[0125] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278, WO95/34656, EP-A-0 427 529, EP-A- 451 878 and WO 03/052073.

[0126] Processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

[0127] The toxin contained in transgenic plants gives the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are, in particular, commonly found in beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0128] Transgenic plants containing one or more genes that encode insecticide resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab toxin and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac toxin and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A toxin and a Cry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerant trait), Agrisure® CB Advantage (Bt11 (CB) corn bora trait) and Protecta®.

[0129] Additional examples of such transgenic crops are: 1. Maíz Bt11 from Syngenta Seeds SAS, Chemi' de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 . Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maíz also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 2. Corn Bt176 from Syngenta Seeds SAS, Chemi’ de l’Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 3. Maíz MIR604 from Syngenta Seeds SAS, Chemi’ de l’Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Corn that has been rendered insect resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin G protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03/018810. 4. Maíz MON 863 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera-type insects. 5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02. 6. Maíz 1507 of Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. The maize genetically modified for the expression of the Cry1F protein to achieve resistance to certain Lepidoptera-type insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium. 7. Maíz NK603 x MON 810 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. They consist of hybrid corn varieties conventionally reproduced by crossing the genetically modified varieties NK603 and MON 810. The NK603 x MON 810 corn transgenically expresses the CP4 EPSPS protein, obtained from Agrobacterium sp. strain CP4, which confers tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. Kurstaki, which breeds tolerance to certain Lepidoptera, including the European corn borer.

[0130] Compounds of Formula (I) (including any compound described in Tables 1.1 to 1.3, or a compound 1.1 to 1.3 described in Table T1 (below)) can be used to control or prevent phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

[0131] In particular, transgenic soybean plants that express toxins, for example, insecticidal proteins such as delta-endotoxins, for example, Cry1Ac (Cry1Ac Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (see, for example, paragraph [008] reference to Intact soybeans RR2 PROTM)), event MON87751 (U.S. Patent Application Publication No. 2014/0373191) or event DAS-81419 (U.S. Patent No. 8632978 and related applications and patents).

[0132] Other transgenic soybean plants may comprise event SY-T0H2 - tolerance to HPPD (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON-9788 - tolerance to glyphosate (Patent U.S. Patent Application No. 7,632,985 and related applications and patents), event MON-7708 - dicamba tolerance (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), event DP- 356-43- 5 - glyphosate and ALS tolerance (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), event A27-4-12 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008 /0320616 and related applications and patents), event DP-305-23-1 - tolerance to ALS (U.S. Patent Application Publication No. US 2008/0312082 and related applications and patents), event A554--127 - tolerance to glufosinate (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS-40-78-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see documents WO 2011/022469, WO 2011/022470, WO 2011/022471, and related applications and patents), event-127 - ALS tolerance (WO 2010/080829 and related applications and patents), event GTS 4--3-2 - glyphosate tolerance, event DAS-68-16-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, event-FG72 - tolerance to glyphosate and isoxaflutol, event BPS-CV-27-9 - tolerance to ALS and -U262 - tolerance to glufosinate or event SY-T04R - HPPD tolerance.

[0133] The “wilderness locus” as used herein means fields in or upon which plants grow, or in which the seeds of cultivated plants are sown, or in which the seed will be placed in the soil. It also includes soil, seeds and seedlings, as well as established vegetation.

[0134] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[0135] The term "lanta propagation material" is understood to denote generative parts of the plant, such as seeds, which can be used for their multiplication, and vegetative material, such as cuttings or tubers, e.g. potatoes . For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants may be mentioned. Germinated plants and young plants that must be transplanted after germination or after emergence from the soil may also be mentioned. These young plants can be protected before transplanting by a full or partial dip treatment. Preferably, “plant propagation material” is understood to denote seeds.

[0136] The compounds of Formula (I) can be used in an unmodified form or, preferably, in conjunction with the adjuvants conventionally used in the formulation technique. For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, for example, in polymeric substances. As with the type of compositions, application methods, such as spraying, atomizing, dusting, dispersing, coating or pouring, are chosen according to the intended objectives and the prevailing circumstances. The compositions may also contain additional adjuvants such as stabilizers, defoamers, viscosity regulators, binders or stickiness promoters as well as fertilizers, micronutrient donors or other formulations to obtain special effects.

[0137] Carriers and adjuvants suitable, for example, for agricultural use, can be solid or liquid and are substances useful in formulation technology, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are, for example, described in WO 97/33890.

[0138] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may additionally include a wetting agent to enhance activity as well as an antifoam and a crystal growth inhibitor. During use, these concentrates are diluted in water and typically applied as a spray to the area to be treated. The amount of active ingredient can vary from 0.5% to 95% of the concentrate.

[0139] Wettable powders are in the form of finely divided particles that readily disperse in water or other liquid carriers. The particles contain the active ingredient trapped in a solid matrix. Typical solid matrices include ter52econdfuller, kaolin clays, silicas, and other readily moist organic or inorganic solids. Wettable powders typically contain 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0140] Emulsifying concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other solvents non-volatile organics. During use, these concentrates are dispersed in water or another liquid and typically applied as a spray to the area being treated. The amount of active ingredient can vary from 0.5% to 95% of the concentrate.

[0141] Granular formulations include both extruded and relatively coarse particles and are generally applied without dilution to the area where treatment is needed. Typical carriers for granular formulations include sand, econdfuller, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, dough, wood flour, corn cobs crushed, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, earth diatom, calcium sulfate and other organic or inorganic materials that absorb or can be coated with the active compound. Granular Formulations typically contain 5% to 25% active ingredients which may include surfactants such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or adhesives, such as dextrins, glue or synthetic resins.

[0142] Dusts are mixtures by free-flow addition of the active ingredient with finely divided solids such as talc, clays, flours and other organic or inorganic solids that act as dispersants and carriers.

[0143] Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell that allows the enveloped material to escape to surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The liquid involved typically constitutes 50 to 95% of the capsule weight and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes that seal the granule pore openings, trapping the active species in liquid form within the granule pores. The beads typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter. Granules are formed by extrusion, agglomeration or compression, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0144] Other formulations useful for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprays, in which the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling point dispersant solvent carrier, can also be used.

[0145] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention into the types of formulations described above are well known to those skilled in the art.

[0146] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, agricultural oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2 -butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, carbonate ethylene, 1,1,1-trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate , glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isoborema acetate, iso-octane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone , methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate , butyl acetate, methanol, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for diluting concentrates.

[0147] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, bark cottonseed, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

[0148] A wide range of surface active agents are advantageously employed in both said liquid and solid compositions, especially those designated as being diluted with carrier before application. These agents, when used, typically comprise 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic or polymeric in character and may be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products such as C.sub nonylphenol ethoxylate. 18; alcohol-alkylene oxide addition products, such as C.sub tridecyl alcohol-ethoxylate. 16; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0149] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoam agents, light blocking agents, compatibilizing agents, antifoam agents , sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, flavorings, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesive agents.

[0150] Furthermore, other biocidally active ingredients or compositions can be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these additional active ingredients can be formulated together with the compositions of the invention or mixed, for example, in the spray tank. These additional biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.

[0151] Reference is made here to pesticidal agents using their common name, known for example from “The Pesticide Manual”, 15th Edition, British Crop Protection Council 2009.

[0152] Additionally, the compositions of the invention can also be applied with one or more inducers of systemically acquired resistance (“SAR” inducer). SAR inducers are known and described, for example, in United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0153] The compounds of Formula (I) are normally used in the form of agrochemical compositions and can be applied to the crop or plant area to be treated, simultaneously or in succession with additional compounds. These additional compounds can be, for example, fertilizers or micronutrient donors or other preparations, which influence plant growth. They can also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired, together with carriers, surfactants or additional application promoting adjuvants employed as usual. in the formulation technique.

[0154] The compounds of Formula (I) can be used in the form of compositions (fungicides) to control or protect against phytopathogenic microorganisms, comprising as an active ingredient at least one compound of Formula (I) or at least one preferred individual compound as herein defined, in free form or in agrochemically usable salt form, and at least one of the adjuvants mentioned above.

[0155] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of Formula (I), an agriculturally acceptable carrier and optionally an adjuvant. An agriculturally acceptable carrier, for example, is a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more pesticide-active compounds, for example, an additional fungicidal active ingredient in addition to the compound of Formula (I).

[0156] The compound of Formula (I) may be the only active ingredient of a composition or may be mixed by addition with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate . An additional active ingredient may, in some cases, result in unexpected synergistic activities.

[0157] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides , benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorus fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, fungicides polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides , thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0158] Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1, 4-methane-naphthalen-5-yl)-amide, 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl] - amide, 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)- amide (1072957-71-1), acid 1 -methyl-3-difluoromethyl-1H- pyrazol-4-carbo'yl (4'-methylsulfanyl-biphenyl-2-yl)- amide, 1-methyl-3-difluoromethyl-4H-pyrazol-4-carboxylic acid [2- (2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide, (5-chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy- 6-methyl-phenyl)-methanone, (5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, 2-{ 2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyemprop-2-en-(E)-ylideneamino-oxymethyl]-phenyl}-2-[(Z)-methoxy-imino] -N-methyl-acetamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, (E)-N-methyl-2-[2-(2 , 5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazol-1-sulfonamide, a-[N-(3-chloro-2, 6- xylyl)-2-methoxyacetamido]-γ-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazol-1-sulfonamide, N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene -3-carboxamide, N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide, N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, (.+-. )-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol, 2-(1-tert-butyl)-1-(2-chlorophenyl )-3-(1,2,4-triazol-1-yl)-pro'an'2-ol, 2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1 ,3-thiazol-5-carboxanilide, 1-imid'zolyl-1-(4'-chlorophenoxy)-3,3-dimethylbutan-2-one, (E)-2-[2-[6-(2-cyanophenoxy )pyrimidin-4-yloxy]phenyl]methyl 3-methoxyacrylate, (E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-methyl3-methoxyacrylate, (E) Methyl -2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin- Methyl 4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-methyl 3-methoxyacrylate, (E)-2-[ Methyl 2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(phenylsulfonyloxy)phenoxy]phenyl-3-methoxyacrylate ( E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate methyl, (E)-2[2-(2-phenylethen-1-yl)-phenyl]-3- methyl methoxyacrylate, (E)-2-[2-(3,5- dic62econdoxy)pyridin-3- yl]-methyl 3-methoxyacrylate, (E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methyl methoxyacrylate, (E)-2-( Methyl 2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate, (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methylmethoxyacrylate, (E )-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methyl methoxyacrylate, (E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methyl methoxyacrylate, (E) - Methyl 2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methylmethoxyacrylate, (E )-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl] Methyl -3-methoxyacrylate, (E)- 2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methylmethoxyacrylate, (E)-2-[2-[6-( Methyl 2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-methyl 3-methoxyacrylate, (E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-[6-(2-chloropyridin-3 - methyl yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloxyminomethyl)phenyl]-methyl 3-methoxyacrylate , (E)- 2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methyl methoxyacrylate, (E),(E)-2-{2- Methyl (3-methoxyphenyl)methyloxyminomethyl]-phenyl}-3-methoxyacrylate, (E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-methyl 3-methoxyacrylate, (E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloxyminomethyl]phenyl}-3-methyl methoxyacrylate, (E),(E)-2-{2-[(4 -chlorophenyl)- methyloxyminomethyl]-phenyl}-methyl 3-methoxyacrylate, (E)- 2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl} -3- methyl methoxyacrylate, (E),(E)-2-{2-[(3-nitrophenyl)methyloxyminomethyl]phenyl}-3-methyl methoxyacrylate, 3-chloro-7-(2-aza-2, 7,7-trimemyloct-3-en-5-ine), 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal , 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, n-butylcarbamate 3-iodo-2-propynyl, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenylcarbamate; phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol , 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1, 3,5-Thiadiazine-2-thione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acipetacs, alanicarb, albendazole, aldimorph, allyl econdyl alcohol, ametoctradine, amisulbrom, amobame, ampropylphos, anilazine, asomate, aureofungin , azaconazole, azafendine, azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentalurone, bentiavalicarb, bentiazole, benzalkonium chloride, benzamacryl, benzamorph, benzohydroxamic acid, benzovindiflupyr, berberine, bethoxazine, biloxazole, binapacryl, biphenyl, bitercanol, bitionol, bixaphene, blasticidin-S, boscalid, bromothalonil, bromuconazole, bupyrimate, butiobate, butylamine calcium polysulfide, Captafol, Captan, Carbamorph, carbendazime, carbendazime hydrochloride, carboxine, carpropamide, carvone, CGA41396, CGA41397, quinomethionate, chitosan, clobenthiazone, chloraniformethane, chloranil, chlorphenazole, chloroneb, chloropicrin, chlorothalonil, chlorozolinate, clozolinate, climbazole, clotrimazole, clozilacone, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate copper, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper thallate, copper zinc chromate and Bordeaux mixture, cresol, kofraneb, cuprobam, copper oxide, cyazofamide, cyclafuramide, cycloheximide, cyflufenamide, cymoxanil, cipendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, disulfide of 1, 1'-di-2-pyridyl dioxide, diclofluanid, diclomezine, diclone, dichloran, dichlorophene, diclozolin, diclobutrazol, diclocimet, diethofencarb, difenoconazole, diphenzoquat, diflumetorime, thiophosphatem O, O-diiso-propyl-S-benzyl, dimefluazole, dimethaclone, dimethconazole, dimetomorph, dimetirimol, diniconazole, diniconazole-M, dinobutone, dinocap, dinoctone , dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrythion, disulfiram, dictatorylimphos, dithianone, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicine, dodine, doguadine, drazoxolone, edifenphos, enestroburin, epoxiconazole, etaconazole, ethema, etaboxam, ethyrimole, ethoxyquin , ethylicin, (Z)-N-benzyl-N ([methyl (methyl-thioethylideneamino-oxycarbonyl) amino]thio)-ethyl-β-alaninete, etridiazole, famoxadone, fenamidone, phenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuramen, fen - hexamide, fenitropane, fenoxanil, fenpiclonil, fenpicoxamide, fenpropidine, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbame, ferimzone, fluazinam, fludioxonil, flumetovera, flumorph, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole , flusulfamide, flutanil, flutolanil, flutriafol, fluxapi65econdita65spet, formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furfural, furmeciclox, furophanate, gliodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexacon azole, hexylthiophos, hydrargafen, hydroxyisoxazole, himexazole, imazalyl, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezine, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isothianyl, is ovaledione, isopamphos , kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamide, maneb, mebenil, mecarbinzide, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, meptildinocap, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole , metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxidine, myclobutanil, myclozolin, nabame, natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostemne, nitrotal -iso- propyl, nuarimol, octilinone, ofurace, organomercury compounds, orissastrobin, ostol, oxadixyl, oxasulfuron, oxathiapiproline, copper oxine, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencycurone, penflufen, pentachlorophenol, penthiopyride, fenamacryl, phenazine oxide, phosdiphene, fosetyl-Al, phosphorous acids, phthalide, picoxystrobin, piperaline, polycarbamate, polyoxin D, polyoxrime, polyrame, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazide, prothiocarb , prothioconazole, pidiflumetofen, pyracarbolide, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos, piribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyriophenone, pyroquilone, pyroxychlor, pyroxyfur, pyrrolnitrine, quaternary ammonium compounds, quinacetol, quinazamide, quinconazole, quinomethionate, quinoxy hay, quintazene, rabenzazole, santonin, sedaxane, siltiofame, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, sultropene, tebuconazole, tebfloquine, teclophthalam, technazene, tecorame, tetraconazole, thiabendazole, thiadifluorine, ticiophene, thifluzamide, 2-(thiocianomethylthio)benzothiazole , thiophanate-methyl, thioquinox, thiram, tiadinyl, timibenconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimephone, triadimenol, triamifos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazol, triforin, triflumizole, triticonazole, uniconazole, urbacide , validamycin, valifenalate, vapame, vinclozolin, zarilamide, zineb, zirame and zoxamide.

[0159] The compounds of the invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the macrocyclic lactone class of compounds such as derivatives of ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin as described in EP-357460, EP-444964 and EP -594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxybendazole, parbendazole and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramissole, levadamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintic agents include flukicides such as triclabendazole and clorsulone and cestocides such as praziquantel and epsiprantel.

[0160] The compounds of the invention can be used in combination with derivatives and analogues of the paraherquamide/marcfortin class of anthelmintic agents, as well as antiparasitic oxazolines such as those disclosed in documents US-5478855, US-4639771 and DE-19520936.

[0161] The compounds of the invention can be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents such as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945 , WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173 and EP 0 503 538.

[0162] The compounds of the invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenurone; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and similar.

[0163] The compounds of the invention can be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly with the compounds disclosed therein.

[0164] Other examples of such biologically active compounds with which the compounds of the invention can be used in combination include, but are not limited to, the following:

[0165] Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demetone, demetone-S-methyl, demetone-S-methyl sulfone, dialyphos, diazinone, dichlorvos, dicrotophos, dimethoate, disulfotone, ethione, etoprophos, etrymphos, famfur, fenamiphos, fenitrothion, fensulfothione, fenthione, flupyrazophos, phonofos, formotiona, fosthiazate, heptenophos, isazophos, isothioate, isoxathione, malathion, metacryphos, methamidophos, methidathione , methyl-parathion, mevinphos, monocrotophos, nalede, omethoate, oxidemeton-methyl, paraoxone, parathion, parathion-methyl, phentoate, fosalone, phospholane, phosphocarb, phosmet, phosfamidone, phorate, foxime, pirimiphos, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiophos, pyraclophos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupyrimphos, tetrachlorvinphos, thytone, triazophos, trichlorphone, vamidothion.

[0166] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloretocarb, ethiofencarb, fenoxycarb, fenthiocarb, furatiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, (methyl) 5-methyl-m-cumenylbutyryl carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

[0167] Pyrethroids: acrinatin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl) 5-benzyl-3-furylmethyl cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioalethrin, bioalethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI- 85193, cycloprothrin, cyhalothrin, cytithrin, cyfenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t- fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

[0168] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, triflumurone, buprofezin, diophenolan, hexithiazox, etoxazole, chlorphentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0169] Other antiparasitics: acequinocil, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus turingiensis, bensultape, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, campeflor, cartape, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide , clotianidine, ciromazine, diaclodene, diafentiurona, dbi-3204, dinactin, di-hidroximethyldi-hydroxypirolidine, dinobutone, dinocape, endsulfan, etiprol, etofenprox, phenazaquin, mti-800, phenpyiroximate, flubricipirime, flubenzymine, fluid BROCITRATE, FLUFENZINE, FLUFENPROX , fluproxifen, halofenprox, hydramethylnone, IKI-220, canemite, N70ec6, neem protectant, nidinorterfuran, nitanpyram, SD-35651, WL-108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridabem, pyrimidifeme, NC-1111, R-195 ,RH- 0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifone, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin , verbutin, vertalec, YI-5301.

[0170] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0171] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0172] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, Kenamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole .

[0173] The following mixtures of compounds of Formula (I) with active ingredients are preferred. The abbreviation "TX" means a compound selected from the group consisting of the compounds described in Tables 1.1 to 1.3 or Table T1 (compounds 1.1 to 1.3) (below):

[0174] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,

[0175] an acaricide selected from the group of substances consisting of 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC name) Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1 ) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion ( 870) + TX, amidoflumeth [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX , arsenic oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (name IUPAC) (888) + TX, azocyclotin (46) + TX, nitrogenate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX,benzoximate (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclene (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxime (103) + TX, butoxycarboxime (104) + TX, butylpyridabene (alternative name) + TX, polysulfide calcium (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione'(947) + TX, CGA 50' 439 (development code) (125) + TX, quinomethionate (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorphenetol (968) + TX, chlorfensone (970) + TX, chlorfensulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiurone (978) + TX, chloropropylate ( 983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX , clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamitone (alternative name) [CCN] + TX, crotoxifos (1010) + TX, cufraneb (1013) + TX , cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyexatin (199) + TX, cypermethrin (201) + TX, DCPM ( 1032) + TX, DDT (219) + TX, demephione (1037) + TX, demephione-O (1037) + TX, demephione-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039 ) + TX, diafentiurone (226) + TX, dialiphos (1042) + TX, diazinone (227) + TX, diclofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242 ) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dynactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobutone (269) + TX, dinocape (270) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinoctone (1090) + TX, dinopentone ( 1092) + TX, dinosulfone (1097) + TX, dinoterbone (1098) + TX, dioxathione (1102) + TX, diphenyl sulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfotone (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothione (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethione (309) + TX, ethoate-methyl (1134) + TX, etoxazole (320) + TX, etrimphos (1142) + TX, fenazaflor (1147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, phensone (1157) + TX, fentriphanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacripyrime (360) + TX, fluazurone (1166) + TX, flubenzimine (1167) + TX, flucicloxurone (366) + TX , flucitrinate (367) + TX, fluemethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formotiona (1192) + TX, formparanate (1193) + TX, gamma-HCH (430) + TX, gliodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX , isocarbophos (alternative name) (473) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmoline II (696) + TX, jodfenfos (1248) + TX, lindane (430) + TX, lufenurone (490) + TX, malathion (492) + TX, malonobene (1254) + TX, mecarbame (502) + TX, mephospholane (1261) + TX, messulfen (alternative name) [CCN] + TX, metacrifos (1266) + TX, methamidophos (527) + TX, methidathione (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX , mipafox (1293) + TX, monocrotophos (561) + TX, morphothione (1300) + TX, moxidectin (alternative name) [CCN] + TX, nalede (567) + TX, NC-184 (compound code) + TX , NC-512 (compound code) + TX, nifluridide (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxidisulfot'in (1325 ) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phencaptone (1330) + TX, phentoate ( 631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosfamidone (639) + TX, phoxime (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacil (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidathione (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridafenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (711) + TX, quintiophos (1381) + TX, R -1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, escradana (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sofamide (1402) + TX, spirodiclofen (738) + TX, spiromesiphene (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramide (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbame (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifone (786) + TX, tetranactin (name alternative) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiophanox (800) + TX, thiometone (801) + TX, thioquinox (1436) + TX , thuringiensin (alternative name) [CCN] + TX, triamifos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorphone (824) + TX, trifenofos ( 1455) + TX, trinactin (alternative name) (653) + TX, vamidothione (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,

[0176] an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutrin [CCN] + TX, diclone ( 1052) + TX, dichlorophene (232) + TX, endotal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabame (566) + TX, quinoclamine (714) + TX, quinonamide ( 1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX,

[0177] an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate ( 291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,

[0178] an avicid selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, phe76econdit (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine ( 745) + TX,

[0179] a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) ( 748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, teclophthalam (766) + TX, and thiomersal (alternative name) [CCN] + TX,

[0180] a biological agent selected from the group of substances consisting of Adoxophies orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani ( alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide ( scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thu77ecôndita77ssubesp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri ( alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (name scientific) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alias) alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) ) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name ) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, amyloliquefacienes from Bacillus subtilis var. Strain FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA and known under the trade name Taegro®) + TX,

[0181] a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,

[0182] a chemosterilant selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzurone (250) + TX, dimatife ( alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl afolate [CCN] + TX, morzide [CCN] + TX, penflurone (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

[0183] an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acemate with (E)-dec-5-en-1-ol (IUPAC name) ( 222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + em, (E)-6-methyl-hept-2-en-4-ol (IUPAC name ) (541) + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1- acetate yl (IUPAC name) (285) + TX, (Z)-hexadec-11-enal (IUPAC name) (436) + TX, (Z)-hexadec-11-en-1-yl aemtate (IUPAC name) ( 437) + TX, (Z)-hexadec-13-en-11-in-1-yl emcetate (IUemC name) (438) + TX, (Z)-icos- 13-en-10-one (IUPem name ) (448) + TX, (Z)-tetradec-7-en-1- al (IemAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name ) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12- acetate dien-1-yl (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name ) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemon (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparleme (277) + TX, dodec-8-en-1-yl acetate (IemAC name) (286) + TX, dodec-9-en- acetate 1-yl (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, 4 -ethyl methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421 ) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate ( IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) alternative) [CCN] + TX,

[0184] an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX , dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] +TX,

[0185] an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl )ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/Chemical Abstracts name) ( 1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl) methylcarbamate phenyl (IUPAC/Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, diethyl 2-chlorovinyl phosphate (IUPAC name) ( 984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-dimethylcarbamate methyl-1-phenylpyrazol-5-yl (IUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, dimethylcarbamate 5,5-dimethyl-3-oxocyclohex-1-enyl (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethione (alternative name ) [CCN] + TX, acetoprol [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, alosamidine (alternative name) [CCN] + TX, alixicarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name ) [CCN] + TX, aluminum phosphide (640) + TX, amidithione (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate ( 875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidathione (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name ) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, nitrogenate (889) + TX, Bacillus thuringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) ( 893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta- cypermethrin (203) + TX, bifenthrin (76) + TX, bioalethrin (78) + TX, S-cyclopentenyl bioalethrin isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX , bioresmethrin (80) + TX, bis(2-chloroethyl) ether (IUPAC name) (909) + TX, bistriflurone (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinphos (914 ) + TX, bromocyclene (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99 ) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxime (103) + TX, butonate (932) + TX, butoxycarboxime (104) + TX, butylpyridabene (alternative name) + TX, cadusafos (109 ) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenothione (947) + TX, Carbosulfan (119) + TX, Cartap (123) + TX, Cartap Hydrochloride (123) + TX, Cevadine (alternative name) (725) + TX, Chlorbicyclene (960) + TX, Chlordane (128) + TX, Chlordecone ( 963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazurone (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxime (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cysmethrin (80 ) + TX, clocitrin (alternative name) + TX, cloetocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [ CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumitoate (1006) + TX, crotamitone (alternative name) [CCN] + TX, crotoxiphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cyclothrin [ CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (name alternative) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT ( 219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demethone (1038) + TX , demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialiphos (1042) + TX, diamidaphos (1044) + TX, diazinone (227) + TX, Dicaptone (1050) + TX, diclofenthion (1051) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) + TX, diflubenzurone (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimethylan (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diophenolan (1099) + TX, dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxathione (1102) + TX, disulfotone (278) + TX, diticrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone ( alternative name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endothione (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonan (1124) + TX, eprinomectin (alternative name) [ CCN] + TX, esfenvalerate (302) + TX, etafos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, etiprol (310) + TX, ethoate-methyl (1134) + TX, etoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (name chemical) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrymphos (1142) + TX, EXD (1143) + TX, famfur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, fenchlorphos (1148) + TX, fenetacarb (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX , fenoxycarb (340) + TX, fenpyrithrin (1155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendiamide (CAS Reg. No.: 272451-65-7) + TX, flucofurone (1168) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, flueethyl (1169) + TX, flufenerime [CCN] + TX, flufenoxurone (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate ( 1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formotiona (1192) + TX, formparanate ( 1193) + TX, fosmethylan (1194) + TX, fospirate (1195) + TX, fosthiazate (408) + TX, fosthiethane (1196) + TX, furatiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumurone (439) + TX , HHDN (864) + TX, hydramethylnone (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprotrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazophos (1231) + TX, isobenzane (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrine (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane ( 474) + TX, isothioate (1244) + TX, isoxathione (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenfos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, Celevana (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lyrimphos (1251) + TX, lufenurone (490) + TX, lithydathione (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX , malonobene (1254) + TX, mazidox (1255) + TX, mecarbame (502) + TX, mecarphone (1258) + TX, menazone (1260) + TX, mephospholane (1261) + TX, mercurous chloride (513) + TX , mesulfenphos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, metam-potassium (1266) + TX , methamidophos (527) + TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268) + TX, methidathione (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methotrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, methoxadiazone (1288) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothione (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nalede (567) + TX, naphthalene (IUPAC/Chemical name Abstracts) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novalurone (585) + TX, noviflumurone (586) + TX, O-5-dichloro- O-ethyl ethylphosphonothioate 4-iodophenyl (IUPAC name) (1057) + TX, O-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate (IUPAC name) (1074) + TX, O-6 O,O-diethyl-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPA name') '1075) + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate (IUPAC name) (1424) + TX , oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxidemeton-methyl (609) + TX, oxideprophos (1'24) + TX, oxydisulfotone (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penflurone (alternative name) [CCN] + TX, pentachlorophenol ( 623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phencaptone (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, fosnichlor (1339) + TX, phosfamidone (639) + TX, phosphine (IUPAC name) (640) + TX, phoxime (642) + TX, phoxim-methyl (1340) + TX, pyrimetaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, arsenite potassium [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precono I (alternative name) [CCN] + TX, precono II (alternative name) [CCN] + TX, precono III (alternative name) [CCN] + TX, primidofos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacil (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidathione (1360) + TX, prothiophos (686) + TX, protoate (1362) + TX, protrifenbut [CCN] + TX, pymetrozine (688) + TX , pyraclophos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridalyl (700) + TX, pyridafenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalphos ( 711) + TX, quinalphos-methyl (1376) + TX, quinothione (1380) + TX, quinthiophos (1381) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, riania (alternative name) (1387 ) + TX, ryanodine (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradana (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399) + TX , sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sofamide (1402) + TX, spinosad ( 737) + TX, spiromesifene (739) + TX, spirotetrmate (CCN) + TX, sulcofurone (746) + TX, sulcofuron-sodium (746) + TX, sulfluramide (750) + TX, sulfotep (753) + TX, fluoride sulfuryl (756) + TX, sulprophos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX , tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimphos (764) + TX, teflubenzurone (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbame (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclamen (798) + TX, thiocyclamen hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometone (801) + TX, thionazine (1434) + TX, thiosultap (803) + TX, thiosultap- sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorphone (824) + TX, trichlorometaphos-3 (alternative name) [CCN] + TX, trichloronate (1452) + TX, trifenofos (1455) + TX, triflumurone (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidothione (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrin ( alternative name) (725) + TX, , zinc phosphide (640) + TX, zolaprophos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprol [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopirafen [560121-52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramate [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2 ] + TX, triflumezopyrime (disclosed in WO 2012/092115) + TX,

[0186] a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloretocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530 ) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, tripenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [39473071 -3] + TX,

[0187] a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045) + TX, 1, 2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 1 3,4-Dichlorotetrahydrothiophene,1-dioxide (IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5- acid methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN ] + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX , cloetocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidaphos (1044) + TX, diclofenthion (1051 ) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name ) [CCN] + TX, etoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, fosthiazate (408) + TX, fosthiethane (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN ] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636 ) + TX, phosfamidone (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbame (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name ) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [31829098-1] + TX,

[0188] a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,

[0189] a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX ,

[0190] a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenic oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912 ) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol ( alternative name) (850) + TX, coumaclor (1004) + TX, coumafuril (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difetialone (249) + TX , diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430 ) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX , methyl bromide (537) + TX, norbormide (1318) + TX, fosacetime (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, arsenite potassium [CCN] + TX, pyrinurone (1371) + TX, scyliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,

[0191] a synergist selected from the group of substances consisting of (2-butoxyethoxy)ethyl 2-piperonylate (IUPAC name) (934) + TX, 5-(1,3- benzodioxol-5-yl)-3- hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code ) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX , sesasmolin (1394) and sulfoxide (1406) + TX,

[0192] an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinone (227 ) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridine-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

[0193] a virucide selected from the group of substances consisting of imannin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,

[0194] a wound protector selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) and thiophanate-methyl (802) + TX,

[0195] and biologically active compounds selected from the group consisting of ametoctradine [865318-97-4] + TX, amisulbrome [348635-87-0] + TX, azaconazole [60207-310] + TX, benzovindiflupyr [1072957- 71-1] + TX, bitertanol [70585-36-3] + TX, bixafen [581809-46-3] + TX, bromuconazole [116255-48-2] + TX, coumoxystrobin [850881-70-8] + TX , cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [23841011-2] + TX, epoxiconazole [106325-08-0 ] + TX, fenbuconazole [114369-43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [ 76674-21-0] + TX, fluxapyroxad [90720431-3] + TX, fluopyram [658066-35-4] + TX, phenaminstrobin [366815-39-6] + TX, isofetamide [875915-78-9] + TX , hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08 -1] + TX, isothianil [224049-04-1] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures described in WO 2010/093059) + TX, mefentrifluconazole [141778203-6 ] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30-4] + TX, penflufen [ 494793-67-8] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-706] + TX, pirifenox [88283-41-4] + TX, prochloraz [67747-095] + TX, propiconazole [60207-90-1] + TX, simeconazole [14950890-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimephone [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [60168- 88-9] + TX, nuarimol [63284-71-9] + TX, bupyrimate [41483-43-6] + TX, dimethyrimole [5221-53-4] + TX, ethyrimole [23947-60-6] + TX , dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-433 ] + TX, cyprodinil [121552-61-2] + TX, mepanipyrim [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [ 131341-86-1] + TX, fluoralaxyl [1383809-87-7] + TX, benalaxyl [71626-114] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-191] + TX, R -metalaxyl [70630-17-0] + TX, ofurace [58810-483] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazime [10605-21-7 ] + TX, debacarb [62732-916] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-798] + TX, clozolinate [84332-86-5] + TX, diclozoline [2420158-9] + TX, iprodione [36734-19-7] + TX, myclozolin [5486461-8] + TX, procymidone [32809-16-8] + TX, vinclozolin [50471-44-8] + TX, boscalid [188425-85 -6] + TX, carboxine [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90- 6] + TX, dodine [2439-10-3] [11265-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961 -524] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, Quresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orisastrobin [248593-16-0] + TX, picoxystrobin [117428-225] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin [862588-11 -2] + TX, ferbame [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [900642-2] + TX, propineb [ 12071-83-9] + TX, tirame [137-26-8] + TX, zinebe [12122-67-7] + TX, zirame [137-30-4] + TX, capitafol [2425-06-1] + TX, capitan [133-06-2] + TX, diclofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3 ] + TX, tolylfluanide [731 -27-1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-391] + TX, copper [53988-93-5] + TX, oxina-copper [10380-286] + TX, dinocap [131-72-6 ] + TX, nitrothal-isopropyl [1055274-6] + TX, edifenfos [17109-49-8] + TX, iprobenfos [2608747-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphene [36519- 00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos- methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-542] + TX, anilazine [101-05- 3] + TX, bentiavalicarb [41361535-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, diclone [117-80-6] + TX, diclocymet [139920-32-4 ] + TX, diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP- LI90 (Flumorph) [211867-47-9] + TX, dithianone [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807 -57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluaziname [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenexamide [126833-17-8] + TX, Fosetyl-aluminum [ 39148-24-8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Ciazofamide) [120116-88-3] + TX, kasugamycin [6980 -18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-036] + TX, pencicurone [66063-05-6] + TX, phthalide [27355-222] + TX, picarbutrazox [ 500207-04-5] + TX, polyoxins [1111380-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12-4] + TX , pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyroquilone [57369-32-1] + TX, pyriofenone [688046-61-9] + TX, piribencarb [799247-52 -2] + TX, Pyrisoxazole [847749-37-5] + TX, Quinoxifene [12449518-7] + TX, Quinzene [82-68-8] + TX, Sulfur [7704-34-9] + TX, Timorex GoldTM (plant extract containing Stockton Group tea tree oil) + TX, tebufloquine [37664578-2] + TX, tiadinil [223580-51-6] + TX, triazoxide [7245958-6] + TX, tolprocarb [911499- 62-2] + TX, triclopiricarb [902760-40-1] + TX, tricyclazole [41814-78-2] + TX, triporin [26644-46-2] + TX, validamycin [37248-47-8] + TX , valifenalate [283159-90-0] + TX, zoxamide (RH7281) [15605268-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, fenamacryl + TX, sedaxane [874967-676] + TX, trinexapac-ethyl [95266-40-3] + TX, (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl )-3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid amide (disclosed in WO 2007/048556) + TX, (3',4',5'-trifluoro-biphenyl-2-yl)- 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid amide (disclosed in WO 2006/087343) + TX, [(3S,4R,4aR,6S,6aS,12R,12aS,12aS)-3- [acyclopaopylcarbonyl)oxy]- 1,3,4,4a,5,6,6a,a2,12a,12b- decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo- 9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7] + TX e 1,3,5 -trimethyl- N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl] -1H- pyrazole-4-carboxamide [926914-55-8] + TX, (i) or a biologically active compound selected from the group consisting of N-[(5-chloro-2-isopropyl-phenyl)methyl] -N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,'-Dimethyl- 1H,5H-[1,4]dithi-ino[2,3-c:5,6- c']dipyrrole-1,3,5,7(2H,6H)-tetrone (can be prepared according to procedures described in WO 2011/138281) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]di-ino[1,2-c]isothiazol-3-carbonitrile + TX , 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedures described in WO 2012/031061) + TX, 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 1,1-dioxide 3-(3,4-Dichloro-1,2-thiazol-5-ylmethoxy)-1 ,2-benzothiazole (can be prepared according to the procedures described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl- acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2-[2-fluoro-6101econdyluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, 2- [2-[(7,8-difluoro101econdytyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, oxathiapiproline [ 1003318-67-9] + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, N- [2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3-(difluoromethyl)-1 -methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, N-[ 2,2,2-trifluoroethyl 2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α, α-tri101econdi-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol + TX, (2RS)-2-[4-(4-chlorophenoxy)-α ,α,α-trifluoro-o-tolyl]- 3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol + TX, 2- (difluoromethyl)-N-[ (3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-'ndan- 4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-'enyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4 ,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (can be prepared according to the procedures described in WO 2007/031513) + TX, methanesulfonate of [2-[3-[2-[1-[2-[3,5-Bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-di -hydroisoxazol-5-yl]-3-chloro-phenyl] (can be prepared according to the procedures described in WO 2012/025557) + TX, N-[6-[[(Z)-[(1-methyltetrazol But-3-ynyl -5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (may be prepared according to the procedures described in WO 2010/000841) + TX, 2-[[ 3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazol-3-thione (may be prepared according to the procedures described in WO 2010/146031) + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol- 2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro- 6 -methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121104) + TX, 2-[2-chloro-4-(4 - 102econdienoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro- 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4-(2,6-difluorophenyl)-6 - methyl-5-phenyl-pyridazine-3-carbonitrile (can be prepared according to the procedures given in WO 2012/020774) + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1 ,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2011/162397 ) + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1-[2-[[1 - (4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072) + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one (can be prepared from according to the procedures described in WO 2014/051165) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxy-imino-N,3-dimethyl- pent-3-enamide + TX, (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX, N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl )-5-fluoro-1-methylpyrazole-4-carboxamide [1255734-28-1] (can be prepared according to the procedures described in 2010/130767) + TX, 3-(difluoromethyl)-N-[(R) -2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazol-4-carboxamide [1352994-67-2] + TX, N'-(2 ,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5- di'ethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX,

[0196] (fenpicoxamide [517875-34-2]) + TX (as described in WO 2003/035617), 2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3- carboxamide + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine- 3-carboxamide + TX, 2-(difluoromethyl)-N-(1,1- dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)- 1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide + TX, 2- (difluoromethyl)-N-[(3R)-3 -ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, and 2-(difluoromethyl)-N-[(3R)- 1,1-dimethyl-3-propyl-indan-4 -yl]pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and/or WO 2016/139189.

[0197] References in square brackets behind the active ingredients, for example, [3878-19-1] refer to the Chemical Abstracts Registry number. The mixing partners described above are known “Where the active ingredients” are included and- "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described herein under the entry number given in rounded brackets above in this document for “joint compound”; For example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added above in this document to the particular compound, wherein the compound in question is included in "Compendium of Pesticide Common Names", which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, Cop“right © 1”95 to 2004]; for example, the compound "acetoprol" is described under the Internet address http://www.alanwood.net/pesticides/acetoprole.html.

[0198] Most of the active ingredients described above are referred to above in this document under a so-called "common name", the "ISO common name" or other "common name" being used in cases If the designation is not a “common name”, the nature of the designation used is instead given in parentheses for the particular compound; in this case the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemical name” is used. ”, a “traditional name”, a “compound name” or a “development code” or, if neither of these designations nor a “common name” is used, an “alternative name” is used. CAS Reg. No." means the Chemical Abstracts Registration Number.

[0199] The active ingredient mixture of compounds of Formula (I) selected from a compound 1.1 to 1.3 described in Table T1 (below) or a compound of Formula (I) described in Tables 1.1 to 1.3 (below), and an active ingredient as described above are preferably in a mixing ratio of 100:1 to 1:6,000, especially 50:1 to 1:50, more especially, in a ratio of 20:1 to 1:20, even more especially from 10:1 to 1:10, most especially from 5:1 and 1:5, special preference being given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 being equally preferred, above all, in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3 , or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4 , or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75 , or 2:75, or 4:75, or 1:6,000, or 1:3,000, or 1:1,500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750 or 4:750. Such mixing ratios are by weight.

[0200] Mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to pests or their environment, with the exception of a method for methods of treating the human body or animal through surgery or therapy and diagnosis performed on the human or animal body.

[0201] Mixtures comprising a compound 1.1 to 1.3 described in Table T1 or a compound of Formula (I) described in Tables 1.1 to 1.3 (below) and one or more active ingredients as described above “may be applied, e.g. , in a single “ready mix” form, in a combined spray mix composed from separate formulations of the “single active ingredient components”, as a “tank mix” and, in a combined use of the single active ingredients when applied in a sequential manner, that is, one after the other in a reasonably short period, such as a few hours or days. The order of applying the compound of Formula (I) selected from those described in Tables 1.1 to 1.3 (below), or Table T1 (below), and the active ingredient (or ingredients) as described above, is not essential to the functioning of the present invention.

[0202] The compositions according to the invention may also comprise additional solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example, coconut oil, rapeseed oil or epoxidized soybean oil), defoamers, e.g. silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients to achieve specific effects, e.g. bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

[0203] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary, e.g. by intimate mixing and/or grinding of the active ingredient with the auxiliary (auxiliary). These processes for preparing the compositions and the use of compounds of Formula (I) for preparing these compositions are also an object of the invention. (i) Another aspect of the invention relates to the use of a compound of formula (I) or of a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I ) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as described above, for the control or prevention of infestation of plants, for example, useful plants, such as crop plants, propagating material thereof, for example, seeds, harvested crops, for example, harvested food crops or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.

[0204] A further aspect of the invention relates to a method for controlling or preventing an infestation of plants, for example, useful plants, such as crop plants, propagation material thereof, for example, seeds, crops harvested, by example, harvested food crops, or non-living materials by insects or phytopathogenic microorganisms or spoilage or organisms potentially harmful to humans, especially fungal organisms, which comprises the application of a compound of formula (I) or a preferred individual compound as defined above as an active ingredient to plants, parts of plants or their locus, their propagating material or any part of non-living materials.

[0205] Means of control or prevention that reduce infestation by microorganisms or phytopathogenic or spoilage organisms potentially harmful to humans, especially fungal organisms, to such a level that an improvement is demonstrated.

[0206] A preferred method for controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which comprises the application of a compound of formula (I), or an agrochemical composition containing at least one of the aforementioned compounds is foliar application. The frequency of application and the application rate will depend on the risk of infestation by the corresponding pathogen or insect. However, compounds of Formula (I) can also penetrate the plant through the roots through the soil (systemic action) by draining the plant locus with a liquid Formulation, or by applying the compounds in solid form to the soil, by example, in granular form (application to the soil). In irrigated rice crops, such granules can be applied to the irrigated rice field. The compounds of Formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0207] A formulation, for example, a composition containing the compound of Formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of Formula (I) can be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example, solvents, solid carriers and optionally surface active compounds (surfactants).

[0208] Advantageous application rates are normally 5 to 2 kg of active ingredient (a.i.) per hectare (ha), preferably 10 g to 1 kgem.i./ha, with maximum preference of 20 g to 600 g a.i./ there is. When used as a seed soaking agent, convenient dosages range from 10 mg to 1 g of active substance per kg of seeds.

[0209] When the combinations of the present invention are used to treat seeds, rates of 0.001 to 50 g of a compound of Formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed are generally sufficient.

[0210] Suitably, a composition comprising a compound of Formula (I) according to the present invention is applied preventively, which means before the development of disease, or curatively, which means after the development of disease.

[0211] The compositions of the invention can be employed in any conventional form, for example in the form of a double package, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a concentrate suitable for flow for seed treatment (FS), a solution for seed treatment (LS), a water-dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), a emulsion, water-in-oil (EO), an emulsion, oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL) , a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any formulation technically possible in combination with agriculturally acceptable adjuvants.

[0212] Such compositions can be produced in a conventional manner, for example, by mixing the active ingredients with suitable formulation inerts (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, antifreeze, adhesives, thickeners and compounds that provide adjuvant effects). Furthermore, conventional slow-release formulations can be employed where long-lasting efficacy is intended. In particular, Formulations to be applied in spray forms, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting agents and dispersants and other compounds that provide adjuvant effects, for example, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, a lignin sulfonate, a fatty alkyl sulfate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[0213] A seed coating formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in the form of a suitable seed coating formulation, for example, as an aqueous suspension or in a form of dry powder having good adhesion to the seeds. Such seed treatment formulations are known in the art. Seed treatment formulations may contain the individual active ingredients or combination of active ingredients in encapsulated form, for example as slow-release capsules or microcapsules.

[0214] In general, formulations include from 0.01 to 90% by weight active agent, from 0 to 20% agriculturally acceptable surfactant, and from 10 to 99.99% solid or liquid formulation inert agents. and adjuvant(s), wherein the active agent consists of at least the compound of Formula (I) optionally together with other active agents, particularly microbiicides or preservatives or the like. Concentrated forms of the compositions generally contain between about 2 and 80%, preferably between about 5 and 70% by weight, of active agent. Application forms of the formulation, for example, may contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Although commercial products are preferably formulated as concentrates, the end user will typically employ diluted formulations.

[0215] Although it is preferred to formulate commercial products as concentrates, the end user will typically use diluted formulations.

[0216] Table 1.1: This table reveals 11 specific compounds of formula (T-1):

[0217] where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is methoxy and NR4(R5) is as defined below in Table 1.

[0218] Each of Tables 1.2 to 1.3 (which follow Table 1.1) provide 11 individual compounds of formula (T-1) in which A, R1, R2 and R3 are as specifically defined in Tables 1.2 and 1.3, which refers to Table 1 where - NR4(R5) is specifically defined. Table 1

[0219] Table 1.2: This table reveals 11 specific compounds of formula (T-1) in which A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is methyl and -NR4 (R5) is as defined above in Table 1.

[0220] Table 1.3: This table reveals 11 specific compounds of formula (T-1) in which A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is ethyl and -NR4 (R5) is as defined above in Table 1 .

EXAMPLES

[0221] The following Examples serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater effectiveness at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the examples, using lower application rates, if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0222] Compounds of Formula (I) may have numerous benefits including, among others, advantageous levels of biological activity to protect plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (e.g., more biological activity , an advantageous spectrum of activity, an increased safety profile (including improved culture tolerance), improved physicochemical properties or increased biodegradability).

[0223] Throughout this description, temperatures are presented in degrees Celsius (°C) and “pf” means melting point. LC/MS stands for Liquid Chromatography Mass Spectroscopy and the description of the devices and method (Methods A and B) is as follows:

The description of the LC/MS device and method A is:

[0224] Waters SQ 2 Detector

[0225] Ionization method: Electrospray

[0226] Polarity: positive and negative ions

[0227] Capillarity (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Dissolution Temperature (°C) 350, Cone Gas Flow (L/H) 0, Dissolution Gas Flow (L/H) 650

[0228] Mass range: 100 to 900 Da

[0229] DAD wavelength range (nm): 210 to 500

[0230] Waters ACQUITY UPLC Method with the following HPLC gradient conditions:

[0231] (Solvent A: Water/Methanol 20:1 + 0.05% formic acid and Solvent B: Acetonitrile + 0.05% formic acid)

[0232] Column type: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 C.

The description of the LC/MS apparatus and method B is:

[0233] Waters SQ 2 Detector

[0234] Ionization method: Electrospray

[0235] Polarity: positive ions

[0236] Capillarity (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, Source Temperature (°C) 150, Dissolution Temperature (°C) 400, Cone Gas Flow (L/H) 60, Dissolution Gas Flow (L/H) 700

[0237] Mass range: 140 to 800 Da

[0238] DAD wavelength range (nm): 210 to 400

[0239] Waters ACQUITY UPLC Method with the following HPLC gradient conditions

[0240] (Solvent A: Water/Methanol 9:1 + 0.1% formic acid and Solvent B: Acetonitrile + 0.1% formic acid)

[0241] Column type: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Column internal diameter 2.1 mm; Particle Size: 1.8 microns; Temperature: 60

[0242] Where necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate through standard physical separation techniques, such as chiral reversed-phase chromatography, or through stereoselective synthetic techniques, e.g. the use of chiral starting materials.

[0243] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly crushed in a mill, producing wettable powders that can be diluted with water to provide suspensions of the desired concentration.

[0244] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly crushed in a suitable mill, producing powders that can be used directly for seed treatment.

[0245] Emulsions of any necessary dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

[0246] Ready-to-use powders are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed films.

[0247] The active ingredient is mixed and crushed with the adjuvants, and the mixture is humidified with water. The mixture is extruded and then dried in a stream of air.

[0248] The finely crushed active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. Non-powdery coated granules are obtained in this way.

[0249] The finely crushed active ingredient is intimately mixed with the adjuvants, providing a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. With the use of such dilutions, live plants, as well as plant propagation material, can be treated and protected against infestation by microorganisms by spraying, pouring or immersing.

[0250] The finely crushed active ingredient is intimately mixed with the adjuvants, providing a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. With the use of such dilutions, live plants, as well as plant propagation material, can be treated and protected against infestation by microorganisms by spraying, pouring or immersing.

Suspension of slow-release capsules

[0251] 28 parts of a combination of the compound of Formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer and 51.6 parts water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete.

[0252] The capsule suspension obtained is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The Capsule Suspension Formulation contains 28% active ingredients. The average capsule diameter is 8 to 15 microns.

[0253] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for that purpose.

List of Abbreviations:

[0254] AIBN = azobisisobutyronitrile

[0255] BOP-Cl = phosphoric acid bis(2-oxo-oxazolidide) chloride

[0256] CDI = 1,1'-carbonyl diimidazole

[0257] DCE = 1,2-dichloroethane

[0258] DCM = dichloromethane

[0259] DIPEA = N,N-diisopropylethylamine

[0260] DMA = dimethylacetamide

[0261] DMF = dimethylformamide

[0262] EtOAc = ethyl acetate

[0263] EtOH = ethyl alcohol

[0264] HCl = hydrochloric acid

[0265] pf = melting point

[0266] MeOH = methyl alcohol

[0267] NaOH = sodium hydroxide

[0268] NBS = N-bromosuccinimide

[0269] TFAA = trifluoroacetic acid anhydride

[0270] THF = tetrahydrofuran

Preparative Examples

[0271] Using the synthetic techniques described both above and below, compounds of formula (I) can be prepared accordingly. Example 1: This example illustrates the preparation of 1-cyclopropyl-1-propyl-3-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] urei' (Compound 1.1 from Table T1) Step 1: Preparation of N'-hydroxy-4-methyl-benzamidine

[0272] To a suspension of 4-methylbenzonitrile (35 g, 0.29 mol) in ethanol (220 ml) and water (440 ml) was added hydroxylamine hydrochloride (41.1 g, 0.58 mol) at room temperature , potassium carbonate (65.4 g, 0.47 mol), and 8-hydroxyquinoline (0.22 g, 1.5 mmol). The reaction mixture was heated at 80 °C for 4 hours. The mixture was then cooled to room temperature and diluted with 2N HCl to pH 8. The volatile products were removed under reduced pressure and the reaction contents were filtered, washed with water, and dried under vacuum to give 39 .1 g of the title compound. LC/MS (Method A) retention time = 0.23 minutes, 151.0 (M+H). Step 2: Preparation of 3-(p-tolyl)'5-(trifluoromethyl)- 1,2,4- oxadiazole

[0273] To a solution of N'-hydroxy-4-methyl-benzamidine (38.7 g, 0.25 mol) in 2-methyltetrahydrofuran (750 ml) was added TFAA at 0 °C. The reaction mixture was stirred at 15 °C for two hours, then diluted with water. The organic layer was separated, washed successively with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride, water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (eluent gradient of heptane/EtOAc 99:1 to 90:10) to yield 54.1 g of the title compound as a clear oil, which solidified upon storage. LC/MS (Method A) retention time = 1.15 minutes, no mass detected.

[0274] 1H NMR (400 MHz, CDCl3) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3Ha.

[0275] 19F NMR (400 MHz, CDCl3) δ ppm: -65.41 (s). Step 3a: Preparation of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

[0276] A mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol ) in tetrachloromethane (480 ml) under argon was heated to 70 °C. AIBN (4.03 g, 24 mmol) was added and the reaction mixture was stirred at 65 °C for 18 hours. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (cyclohane/EtOAc eluent gradient 100:0 to 95:5) to yield 44.7 g of the title compound as a white solid. mp: 58 to 63 °C.

[0277] 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

[0278] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s). (i) 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole was isolated as a by-product as white solid. mp: 61 to 66 °C.

[0279] 1H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

[0280] 19F NMR (400 MHz, CDCl3) δ ppm: -65.34 (s). Step 3b: Preparation of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole from 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1 ,2,4-oxadiazole

[0281] A mixture of 1:9 ratio of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole and 3-[4-(dibromomethyl)phenyl]-5- (trifluoromethyl)-1,2,4-oxadiazole (10.2 g) in acetonitrile (95 ml), water (1.9 ml) and DIPEA (6.20 ml, 35.7 mmol) was added diethyldiethylphosphite (4, 7 ml, 35.7 mmol) at 5 °C. The mixture was stirred at 5 to 10 °C for two hours, 1M HCl was added, and the volatiles were removed under reduced pressure. The resulting white slurry was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (cyclohexane:EtOAc eluent gradient 99:1 to 9:1) to give A 7.10 g of the title compound as a white solid. mp: 58 to 63 °C.

[0282] 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

[0283] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s).Step 4: Preparation of N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]methanamine

[0284] A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (15 g, 46.9 mmol) in THF (20 ml) was added dropwise to the room temperature to a 2M solution of methylamine in THF (120 ml, 234.5 mmol). The mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the resulting crude material was purified by silica gel flash chromatography (cyclohexane/EtOAc eluent gradient 1:0 to 1:1) to provide 10.3 g of the title compound. like a clear oil. LC/MS (Method A) retention time = 0.58 minutes, 258 (M+H).

[0285] 1H NMR (400 MHz, DMSO) δ ppm: 8.08 (d, 2H), 7.47 (d, 2H), 3.84 (s, 2H), 2.48 (s, 3H).

[0286] 19F NMR (400 MHz, CDCl3) δ ppm: -65.39 (s). Step 5: Preparation of 1-cyclopropyl-1-propyl-3-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

[0287] To a solution of triphosgene (0.09 g, 0.29 mmol) in 1,2-dichloroethane (6 ml) was added dropwise a solution of N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]methanamine (0.19 g, 0.58 mmol) and N-ethyl-N-isopropyl-propan-2-amine (0.26 ml, 1.5 mmol) dissolved in 1,2-dichloroethane (2.5 ml) under argon at 0 °C. The mixture was stirred for 1 hour at room temperature. LC/MS and TLC showed full conversion to the corresponding carbamoylchlorate intermediate. A solution of N-ethyl-N-isopropyl-propan-2-amine (0.26 ml, 1.45 mmol) and N-propylcyclopropanamine hydrochloride (0.12 g, 1.16 mmol) in 1,2-dichloroethane (1 ml) was added to the carbamoylchloride intermediate and the reaction was stirred at room temperature overnight. LC/MS and TLC showed total consumption of the carbamoylchloride intermediate. A saturated aqueous sodium bicarbonate solution was added followed by extraction with dichloromethane. The total combined organic layer was dried over sodium sulfate, filtered and evaporated to dryness. The crude product was adsorbed on Isolute® sorbent and subjected to silica gel flash chromatography (cyclohexane/EtOAc 2:1 eluent gradient) to yield 110 mg of the title compound as a colorless oil; LC/MS (Method A) retention time = 1.18 minutes, 383 (M+H).

[0288] 1H NMR (400 MHz, CDCl3) δ ppm: 8.08 (d, 2H), 7.45 (d, 2H), 4.50 (s, 2H), 3.22 (m, 2H), 2.85 (s, 3H), 2.66 (m, 1H), 1.62 (m, 2H), 0.88 (t, 3H), 0.72 (m, 2H), 0.60 (m , 2H).

[0289] 19F NMR (400 MHz, CDCl3) δ ppm: -65.44 (s).

[0290] Example 2: This example illustrates the preparation of intermediate N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine. (i) A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.50 g, 4.69 mmol) in dichloromethane (9.4 ml) was added dropwise at room temperature to a stirred solution of 2 M ethylamine in MeOH (12 ml, 24.0 mmol). The mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water and the layers were separated. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude material was purified by flash chromatography on silica gel (cyclohexane:cyclohexane:EtOAc 1:0 to 1:1) to give 0.92 g of the title compound as a white solid mp: 102 to 112 °C, LC/MS (Method A) retention time = 0.66 minutes, 272 (M+H).

[0291] 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.01 (d, 2H), 7.57 (d, 2H), 3.86 (q, 2H), 3.29 (s l, 1H ), 2.53 (q, 2H), 1.05 (t, 3H).

[0292] 19F NMR (400 MHz, DMSO-d6) δ ppm: -64.77 (s). Example 3: This example illustrates the preparation of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-acetamide (Compound 1.3 of Table T1 below) Step 1: Preparation of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride

[0293] 4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid (4.00 g, 15.0 mmol) was suspended in dichloromethane (90 ml), DMF (0. 1 ml, 0.150 mmol) was added followed by oxalyl chloride (1.46 ml, 16.5 mmol). The mixture was heated at reflux for 2 hours. The mixture was evaporated under reduced pressure to yield 4.15 g of the title compound as a yellow solid. Step 2: Preparation of N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

[0294] A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride from Step 1 (4.15 g, 14.6 mmol) in dichloromethane (20 ml) was added dropwise at room temperature to a stirred solution of N-methoxymethanamine (1.10 g, 17.5 mmol) and triethylamine (3.10 ml, 21.8 mmol) in dichloromethane (80 ml). The mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into water, extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was subjected to flash chromatography on silica gel (heptane/EtOAc eluent gradient 9:1 to 65:35) to yield 4.12 g of the title compound as a solid. LC/MS (Method A) retention time = 0.97 minutes, 302 (M+H).

[0295] 1H NMR (400 MHz, CDCl3) δ ppm: 8.18 (d, 2H), 7.84 (d, 2H), 3.56 (s, 3H), 3.40 (s, 3H). Step 3: Preparation of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

[0296] In a 75 ml multi-neck flask equipped with a stirrer, the thermometer at - 78 ° C under argon, DIBAL-H, 1.0 M in toluene (16 ml, 16.0 mmol) was added dropwise to a solution of N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (4.10 g, 13.3 mmol) in 2-methyltetrahydrofuran (90ml). The mixture was stirred two hours at -78°C and over one hour the temperature was allowed to rise to 0°C. Complete conversion observed by LC-MS. The mixture was quenched by adding drops of saturated aqueous ammonium chloride solution. Precipitation of a white solid occurred. 4 M HCl was added until complete solubilization. The mixture was extracted three times with ethyl acetate. The combined organics were dried over magnesium sulfate and evaporated to give the crude as a beige solid. The crude material was subjected to silica gel flash chromatography (heptane eluent gradient: EtOAc 99:1 to 90:10) to yield 2.93 g of the title compound as a white solid mp: 40 to 50 °C .

[0297] 1H NMR (400 MHz, CDCl3) δ ppm: 10.12 (s, 1H), 8.31 (d, 2H), 8.05 (d, 2H).

[0298] 19F NMR (400 MHz, CDCl3) δ ppm: -65.29 (s). Step 4: Preparation of N-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanimine

[0299] A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (0.30 g, 1.1 mmol) in methanol (11 ml) was treated at room temperature with pyridine (0.15 ml, 1.9 mmol) followed by the addition of O-methylhydroxylamine hydrochloride (0.15 g, 1.8 mmol). The mixture was stirred at room temperature over the weekend, poured into water, acidified with 1 M HCl and extracted three times with ethyl acetate. The combined organics were washed with water, dried over magnesium sulfate and evaporated to give a resin. The crude material was subjected to silica gel flash chromatography (eluent gradient of heptane/EtOAc 100:0 to 95:5) to give the title compound as a white solid mp: 55 to 65°C.

[0300] 1H NMR (400 MHz, CDCl3) δ ppm: 8.14 (s, 1H), 8.11 (d, 2H), 7.73 (d, 2H).

[0301] 19F NMR (400 MHz, CDCl3) δ ppm: -65.40 (s). Step 5: Preparation of N-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

[0302] A solution of N-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanimine (0.81 g, 2.89 mmol) in acid acetic acid (11 ml) was treated at 15 °C with sodium cyano borohydrate (0.4 g, 6.1 mmol). The mixture was stirred at 22°C for 18 hours until complete consumption of the starting material was observed. The reaction mixture was carefully poured into 0.1 M NaOH solution. By adding 1 M NaOH, the pH was adjusted to 12-13. The mixture was extracted four times with TBME. The combined organics were washed twice with water and once with brine, then dried over magnesium sulfate and concentrated under reduced pressure. The resulting green oil was purified by silica gel flash chromatography (eluent gradient of heptane/EtOAc 99:1 to 70:30) to provide 0.60 g of the title compound as an oil.

[0303] 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.53 (d, 2H), 5.33 (s l, 1H), 4.12 (s, 2H), 3.50 (s, 3H).

[0304] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s). Step 6: Preparation of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinane-2—carboxamide

[0305] To a solution of N-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine (0.150 g, 0.55 mmol) in dichloromethane ( 1.5 ml) and DMF (0.2 ml) CDI (0.133 g, 0.82 mmol) was added in portions. The mixture was stirred for 2 hours at room temperature and LC/MS and TLC showed complete consumption of the starting material. Oxazinane (0.24 g, 32.75 mmol) was introduced and the reaction was stirred at room temperature overnight. LC/MS and TLC showed total consumption of the intermediate. The reaction content was diluted with water and dichloromethane, the layers were separated, and the aqueous fraction was then extracted with dichloromethane. The total combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude product was adsorbed on Isolute® sorbent and subjected to silica gel flash chromatography (cyclohexane/EtOAc 2:1 eluent gradient) to yield 190 mg of the title compound as a clear oil; LC/MS (Method A) retention time = 1.11 minutes, 387 (M+H).

[0306] 1H NMR (400 MHz, CDCl3) δ ppm: 8.10 (d, 2H), 7.58 (d, 2H), 4.67 (s, 2H), 4.00 (m, 2H), 3.65 (m, 2H), 3.61 (s, 3H), 1.78 (s l, 4H).

[0307] 19F NMR (400 MHz, CDCl3) δ ppm: -65.38 (s).

[0308] The following procedure was used in a combinatorial manner with the use of suitable building blocks (compounds (II) and (III)) to provide the compounds of Formula (I). Compounds prepared via the following combinatorial protocol were analyzed using LC/MS Method B. (1) By way of exemplification, the acid derivatives of formula (III) (0.0375 mmol in 375 μl of DMA) were transferred to a 96-slot deep well plate (DWP96) containing the derivatives of [[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]oaryl]methanamine of formula (II) (0.03 mmol) and DIPEA (0.09 mmol) in 250 μl of DMA, followed by the addition of BOP- Cl (0.06 mmol) dissolved in DMA (250 μl). The DWP was sealed and stirred at 50°C for 18 hours. The solvent was removed under a stream of nitrogen. The resulting crude residues were solubilized in a mixture of MeOH (250 μl) and DMA (500 μl) and directly subjected to purification by preparative LC/MS which provided the compounds of formula (I) in yields of 10 to 85%.

[0309] The following procedure was used in a combinatorial manner with the use of suitable building blocks (compounds (II) and (IV)) to provide the compounds of Formula (I). Compounds prepared via the following protocol were analyzed using LC/MS Method B.

[0310] By way of example, the portions of triphosgene (5.94 mg) in DCE (0.3 ml) were transferred at 0 C to a 96-slot deep well plate (DWP96) containing the amine derivative [HN (R4)R5] of formula (IV) (0.05 mmol) and triethylamine (0.12 mmol) in 200 μl of DMA. The reaction mixtures were stirred at room temperature for 30 minutes, then [[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine derivatives of formula (II) (0.05 mmol ) and triethylamine (0.12 mmol) in 200 μl of DMA were added. The DWP was sealed and stirred at room temperature for 18 hours. The DCE was removed under Barkey Station. The crude residues were solubilized in a mixture of MeOH (200 μl) and DMA (600 μl) and directly subjected to purification by preparative LC/MS which provided the compounds of formula (I) in yields of 10 to 85%. Table T1 : Melting point (mp) and/or retention times (RT) data for compounds according to Formula (I):

BIOLOGICAL EXAMPLES: General examples of well plate leakage disc tests:

[0311] Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. The cut leaf discs or segments are placed in multi-well plates (24-well format) on water agar. Leaf discs are sprayed with a test solution before (preventive) or after (curative) inoculation. The compounds to be tested are prepared as DMSO solutions (max. 10 mg/ml) that are diluted to the appropriate concentration with 0.025% Tween20 immediately before spraying. The inoculated leaf discs or segments are incubated under defined conditions (temperature, relative humidity, light, etc.), according to the respective test system. A single disease level assessment is performed 3 to 14 days prior to inoculation, depending on the pathosystem. The percentage of disease control relative to untreated check leaf discs or segments is then calculated. General examples of liquid culture tests in well plates: Freshly prepared Mycelia fragments or conidial suspensions of a fungus from liquid cultures of the fungus or from cryogenic storage are directly mixed into nutrient broth. DMSO solutions of the test compound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of 50 and 10 μl of this solution is pipetted into a microtiter plate (96-well format). Nutrient broth containing the fungal spore/mycelia fragments is then added to provide a final concentration of the tested compound. Test plates are incubated in the dark at 24°C and 96% relative humidity. Inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and the percentage antifungal activity relative to the untreated check is ca136econditaExample 1: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / leaf disc preservative (brown rust)

[0312] Leaf segments of wheat cv. Kanzler were placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs were inoculated with a fungal spore suspension 1 day after application. The inoculated leaf segments were incubated at 19°C and 75% relative humidity (rh) under a light regime of 12 hours light/12 hours dark in a climate-controlled cabinet and the activity of a compound was evaluated as a control. percent disease compared to untreated when an adequate level of disease damage appears on untreated check leaf segments (7 to 9 days after application).

[0313] Compounds following 200 ppm in the applied formulation provide at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development. Table T1) 1.137econditaExample 2: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / leaf disc dressing (brown rust)

[0314] Leaf segments of wheat cv. Kanzler are placed on agar in multi-well plates (24-well format). The leaf segments are then inoculated with a suspension of fungal spores. The plates were stored in the dark at 19 °C and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. Leaf segments were incubated at 19°C and 75% relative humidity under a 12-hour light/12-hour dark light regime in a climate-controlled cabinet and the activity of a compound was assessed as percent disease control in comparison. with untreated when an adequate level of disease damage appears on untreated check leaf segments (6 to 8 days after application).

[0315] Compounds following 200 ppm in the applied formulation provide at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development.

[0316] Compounds (from Table T1) 1.2 and 1.3.

Example 3: Fungicidal activity against Phakopsora pachyrhizi / soybean / leaf disc preservative (Asian soybean rust)

[0317] Soybean leaf discs are placed on water agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate-controlled chamber of 24-36 hours in darkness at 20 °C and 75% RH, the leaf discs are maintained at 20 °C with 12 h light/day and 75% RH. The activity of a compound is evaluated as percent disease control compared to untreated when an adequate level of disease damage appears on untreated check sheet discs (12 to 14 days after application).

[0318] Compounds following 200 ppm in the applied formulation provide at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development.

[0319] Compounds (from Table T1) 1.2 and 1.3.

Example 4: Fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liquid culture/cucumber/preservative (Anthracnose)

[0320] The conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB - potato dextrose broth). After placing a solution of (DMSO) test compound in a microtiter plate (96-well format), nutrient broth containing the fungal spores is added. Test plates are incubated at 24°C and growth inhibition is measured photometrically 3 to 4 days after application.

[0321] The following compounds at 20 ppm in the applied formulation provide at least 80% disease control in this test compared to the untreated control under the same conditions, which shows extensive disease development.

[0322] Compounds (from Table T1) 1.2 and 1.3.

Claims (11)

1. Compound of formula (I): characterized by the fact that A is: R1 and R2 are hydrogen; wherein R3 is R3a, wherein R3a is methoxy; R4 is R4a, where R4a is propyl, isopropyl, butyl, isobutyl, sec-butyl, C3-4alkenyl or C1-2fluoroalkyl; R5 is R5a, where R5a is cyano, C3-5 alkyl, C1-3fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cynao alkyl, C1-3 hydroxy alkyl, C1-2 alkoxy C1-3 alkyl, C1-2haloalkoxy C1-3 alkyl, amino C1-3 alkyl, N-C1-3 alkylamino C1-3 alkyl or N,N-diC1-3alkylamino C1-3 alkyl, or R5a is C3-4 cycloalkyl or C3-4 cycloalkyl C1-2alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclyl comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5a, any cycloalkyl or heterocyclyl chemical moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from of R6, where R6 is R6a; R6a represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5a comprises a C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or (ii) R3 is R3b, where R3b is methoxy; R4 is R4b, where R4b is ethyl, C3-4 alkynyl or cyanomethyl; and R5 is R5b, where R5b is C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, cyano, C1-3 alkyl, C1-2 alkoxy, C1-3 alkyl, C1-3 hydroxy alkyl, C1-2haloalkoxy C1-3 alkyl, amino C1-3 alkyl, N-C1-3alkylamino C1-3 alkyl or N,N-diC1-3alkylamino C1-3 alkyl; or R5b is cyclobutyl, C3-4 cycloalkylethyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl, or heterocyclyl C1-2 alkyl, wherein the heterocyclyl moiety is a 4 to 6 non-aromatic ring members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6b; R6b represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5b comprises a C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or (iii) R3 is R3c, where R3c is methoxy; R4 is R4c, where R4c is C1-4 alkoxy; and R5 is R5c, wherein R5c is C2-5 alkyl, C1-3fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, cyano C1-3 alkyl, C3-4 haloalkenyl, hydroxy C1-3 alkyl, C1-2alkoxyC1-3alkyl, C1-2fluoroalkoxyC2-3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or R5c is C3-4 cycloalkyl or C3-4 cycloalkyl C1-2alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or C1-2 heterocyclyl alkyl, wherein the heterocyclyl moiety is a ring 4- to 6-membered non-aromatic compound comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5c, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6c; R6c represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5c comprises a C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or (iv) R3 is R3d, where R3d is methyl or ethyl; R4 is R4d, where R4d is cyano, C3-5alkyl, C1-3fluoroalkyl, C3-4alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C2-4alkoxy or C1-2alkoxy1-3alkyl; and R5 is R5d, where R5d is C2-5alkyl, C3-5alkenyl, C4-5alkynyl, cyanoC1-3alkyl, C1-3fluoroalkyl, C3-4haloalkenyl, hydroxyC1-3alkyl, C1-2alkoxymethyl, C1-2alkoxyC3alkyl, C1-2fluoroalkoxyC1-3alkyl, aminoC1-3alkyl, N-C1-3alkylaminoC1-3alkyl or N,N-diC1-3alkylaminoC1-3alkyl; or R5d is C3-4 cycloalkyl or C3-4 cycloalkyl C2alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclyl C1-2 alkyl, wherein the heterocyclyl moiety is a non-aromatic ring of 4 to 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein, for R5d, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is R6d; R6d represents cyano, halogen, hydroxy, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein, when R5d comprises a substituted C3-4cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or with R3 as defined for each of embodiments (i), (ii), (iii) and (iv), R4 and R5, together with the nitrogen atom to which they are attached, form a cycle selected from of 3-oxo-pyrrolidinyl, 2-oxo-pyrrolidinyl, azetidinyl, oxazolidinyl, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethanone; or a salt or N-oxide thereof. 2. Compound according to claim 1, characterized by the fact that R4c is methoxy or ethoxy. 3. Compound according to claim 1, characterized by the fact that R4d is cyano, C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C4-5alkynyl, cyanoC1-2alkyl, C2-3alkoxy or C1-2alkoxyCi-2alkyl. 4. Compound according to claim i, characterized by the fact that R5a is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl or R5a is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising i or 2 heteroatoms individually selected from N and O, wherein, for R5a, any cycloalkyl or heterocyclyl chemical moiety is optionally substituted by i or 2 substituents, which may be the same or different, selected from R6, wherein R6 is R6a, selected from halogen, methyl and ethyl. 5. Compound according to claim i, characterized by the fact that R5b is C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyCi-2alkyl or R5b is cyclobutyl, C3-4cycloalkylethyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising i or 2 heteroatoms individually selected from N and O, wherein, for R5b, any cycloalkyl or heterocyclyl moiety is optionally substituted by i or 2 substituents, which may be the same or different, selected from R6, where R6 is R6b, selected from halogen, methyl and ethyl. 6. Compound according to claim 1 or 2, characterized by the fact that R5c is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxyC1-2alkyl or R5c is C3- 4cycloalkyl, C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl chemical moiety is a 4- to 6-membered non-aromatic ring comprising i or 2 heteroatoms individually selected from N and O, wherein, for R5c, any cycloalkyl or heterocyclyl chemical moiety is optionally substituted by i or 2 substituents, which may be the same or different, selected from R6, wherein R6 is R6c, selected from halogen, methyl and ethyl. 7. Compound according to claim i or 3, characterized by the fact that R5d is C3-5alkyl, C1-2fluoroalkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl or C1-2alkoxymethyl, or R5d is C3-4cycloalkyl , C3-4cycloalkylC1-2alkyl, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising i or 2 heteroatoms individually selected from N and O, wherein, for R5d , any cycloalkyl or heterocyclyl chemical moiety is optionally substituted by i or 2 substituents, which may be the same or different, selected from R6, wherein R6 is R6d, selected from halogen, methyl and ethyl. 8. Agrochemical composition characterized by the fact that it comprises a fungicidal effective amount of a compound of Formula (I), as defined in any one of claims 1 to 7. 9. Composition, according to claim 8, characterized by the fact that it additionally comprises at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier. 10. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized by a fungicidal effective amount of a compound of Formula (I), as defined in any one of claims 1 to 7, or a composition comprising this compound as an active ingredient, be applied to plants, their parts or their locus. 11. Use of a compound of Formula (I), as defined in any one of claims 1 to 7, characterized by the fact that it is used as a fungicide, wherein said use excludes methods for treating the human or animal body by surgery or therapy.