BR112019020858B1 - MICROBIOCIDENT OXADIAZOLE DERIVATIVE COMPOUNDS, AGROCHEMICAL COMPOSITION, RELATED METHOD AND USE - Google Patents

Abstract

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

Description

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

[0002] WO 2015/185485 describes the use of substituted oxadiazoles to combat phytopathogenic fungi.

[0003] According to the present invention, there is provided a compound of formula (I): wherein A1 represents C-R1, wherein R1 is hydrogen or halogen; A2 represents C-R2, wherein R2 is hydrogen or halogen; A3 represents C-R3, wherein R3 is hydrogen or halogen; A4 represents C-R4, wherein R4 is hydrogen or halogen; wherein 0, 1 or 2 of A1, A2, A3 and A4 is C-halogen; R5 and R6 independently represent hydrogen or methyl; R7 represents C1-4haloalkoxy; Z is selected from Z1, Z2, Z3, Z4 or Z5; where Z1 is -C(O)R8, where R8 is hydrogen, cyano, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-4alkyl, C1-4haloalkyl, C2-6haloalkenyl, hydroxyC1-4alkyl, C1-4alkoxyC1 -4alkyl, C1-4haloalkoxyC1-4alkyl, C1-2alkoxyC1-2alkoxyC1-4alkyl, C2-4alkynyloxyC1-4alkyl, aminoC1-6alkyl, N-C1-4alkylaminoC1-4alkyl, N,N-diC1-4alkylaminoC1-4alkyl, C1-4alkylcarbonylC1-4al kilo , C1-4alkylcarbonylC2-4alkenyl, C1-4alkoxycarbonylC1-4alkyl, C1-4alkylcarbonyloxyC1-4alkyl, N-C1-4alkylaminocarbonylC1-4alkyl, N,N-diC1-4alkylaminocarbonylC1-4alkyl, C1-4alkylsulfanylC1-4alkyl, C1-4alkylsulfanyl onylC1-4alkyl, C1 - 4alkylsulfonylaminoC1-4alkyl, C1-4alkylcarbonylaminoC1-4alkyl, C1-4alkoxycarbonylaminoC1-4alkyl; or R8 represents C3-6cycloalkyl, C3-6cycloalkylC1-2alkyl, phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, 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, wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9; R9 represents cyano, halogen, hydroxy, amino, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4haloalkyl, C1-4alkoxy, C1-4haloalkoxy, C3-4alkenyloxy, C3-4alkynyloxy, N-C1-4alkylamino, N, N-diC1-4alkylamino, C1-4alkylcarbonyl, C3-6cycloalkylcarbonyl, C1-4alkoxycarbonyl, carbonylamino, N-C1-4alkylaminocarbonyl, N,N-diC1-4alkylaminocarbonyl, C1-4alkoxycarbonylamino or C1-4alkylsulfonyl, and wherein when R8 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2; Z2 represents -C(O)OR10, wherein R10 represents hydrogen, C1-4alkyl, C3-5alkenyl, C3-5alkynyl, C1-3haloalkyl, C1-3alkoxyC2-4alkyl; or R10 represents C3-6cycloalkyl or C3-6cycloalkylC1-2alkyl, wherein for R10, any cycloalkyl is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R11; R11 represents cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; Z3 represents -C(O)NR12R13, where R12 represents hydrogen, cyano, C1-4alkyl, C1-4alkoxy, C3-5alkenyl, C3-5alkynyl, C3-4alkenyloxy, C3-4alkynyloxy, cyanoC1-3alkyl, C1-3haloalkyl, C3 -4haloalkenyl, hydroxyC2-4alkyl, C1-2alkoxyC2-4alkyl, C1-2haloalkoxyC2-4alkyl, C1-2alkoxyC2-4alkoxyC2-4alkyl, aminoC2-4alkyl, N-C1-4alkylaminoC2-4alkyl, N,N-diC1-4alkylaminoC2-4alkyl, C1 - 3alkylcarbonylC1-3alkyl, C1-4alkoxycarbonylC1-3alkyl, C1-3alkylcarbonyloxyC2-4alkyl, N-C1-3alkylaminocarbonylC1-3alkyl, N,N-diC1-3alkylaminocarbonylC1-3alkyl, C1-3alkylsulfonyl, C1-3alkylsulfonylC2-3alkyl, C1 -3alkylsulfonylaminoC2-3alkyl ; or R12 represents C3-6cycloalkyl, phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, 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; wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14, R14 represents cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, propen-2 -yl, propyn-2-yl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, propen-2-yloxy, propyn-2-yloxy, N-methylamino, N,N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl , N,N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein when R12 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2; R13 represents hydrogen, halogen, methyl, ethyl, propyl, isopropyl, propen-2-yl, propyn-2-yl, cyclopropyl, cyclopropylmethyl; or R12 and R13 together with the nitrogen atom to which they are attached form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O)2 and NR15; wherein R15 is hydrogen, methyl, methoxy, formyl or acyl; Z4 represents -C(O)C(=R16)R17, wherein R16 represents O or N-methoxy; and R17 represents hydrogen, cyano, amino, hydroxy, C1-4alkyl, C1-4alkoxy, C2-4alkenyl, C3-4alkenyloxy, C2-4alkynyl, C3-4alkynyloxy, cyanoC1-2alkyl, C1-2haloalkyl, C1-2haloalkoxy, hydroxyC1-3alkyl , C1-2alkoxyC1-4alkyl, C1-2haloC1-4alkylamino, N-C1-3alkylamino, N,N-diC1-3alkylamino, N-C1-3alkoxyamino, N-C1-2alkoxy-N-C2-4alkylamino, N-C1-2alkylaminoC1 -3alkyl, N,N-diC1-2alkylaminoC1-3alkyl; R17 represents C3-4cycloalkyl, C3-4cycloalkylamino, C3-4cycloalkyloxy, heterocyclyl, 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; wherein the cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R18; R18 represents amino, hydroxyl, cyano, halogen, hydroxy, C1-4alkyl, allyl, propargyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, N-methylamino, N,N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein where R17 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2; Z5 represents -S(O)2R19, wherein R19 represents amino, C1-4alkyl, C3-5alkenyl, C3-5alkynyl, cyanoC1-4alkyl, C1-3haloalkyl, C1-2alkoxyC1-4alkyl, C1-2haloalkoxyC2-3alkyl, C1-3alkylcarbonylC1 -3alkyl, C1-3alkoxycarbonylC1-3alkyl, C1-3alkylcarbonyloxyC2-4alkyl, N-C1-3alkylaminocarbonylC1-3alkyl, N,N-diC1-3alkylaminocarbonylC1-3alkyl, N-C1-3alkylamino, N,N-diC1-3alkylamino, N-C1 -3alkoxyamino, N-C1-3alkoxy-N-C1-3alkylamino, N-C1-3alkylaminoC1-4alkyl, N,N-diC1-3alkylaminoC1-3alkyl, C1-3alkylcarbonylaminoC2-3alkyl, C1-3alkoxycarbonylaminoC2-3alkyl; or R19 represents C3-6cycloalkyl, C3-4cycloalkylC1-2alkyl, phenyl, phenylC1-2alkyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, or heterocyclyl, 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, wherein cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R20; R20 represents cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; and wherein when R19 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2; or a salt or N-oxide thereof.

[0004] Surprisingly, it has been found that the new compounds of Formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0005] 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.

[0006] According to a third aspect of the invention, there is provided a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidal effective amount of a compound of Formula (I), or of a composition comprising this compound as an active ingredient is applied to the plants, their parts or their locus.

[0007] According to a fourth aspect of the invention, there is provided the use of a compound of Formula (I) as a fungicide. In accordance with this particular aspect of the invention, use may exclude methods for treating the human or animal body by surgery or therapy.

[0008] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chlorine), bromine (bromine) or iodine (iodine), preferably to fluorine, chlorine or bromine.

[0009] As used herein, cyan means a -CN group.

[0010] As used herein, the term "hydroxy" or "hydroxy" refers to an -OH group.

[0011] As used herein, amino means an -NH2 group.

[0012] As used herein, acyl denotes a -C(O)CH3 group.

[0013] As used herein, formyl designates a -C(O)H group.

[0014] As used herein, the term "C1-6alkyl" refers to a radical of a straight or branched hydrocarbon chain consisting only of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and which is connected to the rest of the molecule by a single bond. C1-4alkyl, C1-3alkyl and C1-2alkyl are to be interpreted accordingly. Examples of C1-6 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (t-butyl). A "C1-C2alkylene" group refers to the corresponding definition of C1-2alkyl, except that such a radical is linked to the rest of the molecule by two single bonds. Examples of C1-2 alkylenes are -CH2- and -CH2CH2-.

[0015] As used herein, the term "C1-4alkoxy" refers to a radical of the formula -ORa where Ra is a C1-4alkyl radical as generally defined above. The terms C1-3alkoxy and C1-2alkoxy shall be considered accordingly. Examples of C1-4alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and t-butoxy.

[0016] As used herein, the term "C1-4haloalkyl" refers to a C1-3alkyl radical as generally defined above, substituted with one or more identical or different halogen atoms. Examples of C1-4haloalkyl include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, and 3,3,3-trifluoropropyl.

[0017] As used herein, the term "C2-6 alkenyl" relates to a straight or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one double bond that may have the (E) configuration or (Z), having two to six carbon atoms, which is connected to the rest of the molecule by a single bond. C3-6alkenyl, C3-5alkenyl, C2-4alkenyl and C2-3alkenyl should be interpreted accordingly. Examples of alkenyls C2-6 include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl), and but-1-enyl.

[0018] As used herein, the term "C26 haloalkenyl" refers to a C2-6 alkenyl radical as generally defined above substituted by one or more identical or different halogen atoms. C3-4haloalkenyl should be considered accordingly.

[0019] As used herein, the term "C3-4alkenoxy" refers to a radical of the formula -ORa where Ra is a C3-4alkenyl radical as generally defined above.

[0020] As used herein, the term "C2-6alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one triple bond, having from two to six carbon atoms and which is attached to the rest of the molecule by a single bond. C3-5alkynyl and C2-4alkynyl should be interpreted accordingly. Examples of C2-6alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl).

[0021] As used herein, the term "C3-4alkynyxy" refers to a radical of the formula -ORa where Ra is a C3-4alkynyl radical as generally defined above.

[0022] As used herein, the term "C3-4alkynyloxyC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a C3-4alkynyloxy group as generally defined above.

[0023] As used herein, the term "C1-4alkoxyC1-4alkyl" refers to the radical of the formula Rb-O-Ra- wherein Rb is a C1-4alkyl radical as generally defined above, and Ra is a C1-4alkylene radical as defined in general above.

[0024] As used herein, the term "C1-2alkoxyC1-2alkoxyC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted by a C1-2alkoxy group as defined above, the C1-2alkoxy group itself replaced by a C1-2alkoxy group as defined above.

[0025] As used herein, the term "hydroxyC1-4alkyl" refers to a C1-4alkyl radical as generically defined above substituted with one or more hydroxy groups. The term "hydroxyC1-2alkyl" should be interpreted accordingly.

[0026] As used herein, the term "cyanoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with one or more cyano groups.

[0027] As used herein, the term "C1-4alkylcarbonyl" refers to a radical of the formula -C(O)Ra where Ra is a C1-4alkyl radical as generally defined above.

[0028] As used herein, the term "C1-4alkylcarbonyloxyC1-4alkyl" refers to a radical of the formula RbC(O)ORa- wherein Rb is a C1-4alkyl radical as generally defined above and Ra is a radical C1-4alkylene as generally defined above.

[0029] As used herein, the term "C1-2alkoxyC1-2alkoxyC1-4alkyl" refers to a radical of the formula RaORbORc-, wherein Rb and Rc are C1-2alkylene radicals as generally defined above, and Ra is a C1-4alkyl radical as generally defined above.

[0030] As used herein, the term "C1-4alkoxycarbonyl" refers to a radical of the formula RaOC(O)-, where Ra is a C1-4alkyl radical as generally defined above.

[0031] As used herein, the term "C1-4alkoxycarbonylC1-4alkyl" refers to a radical of the formula RaOC(O)Rb- where Ra is a C1-4alkyl radical as generally defined above and Rb is a radical C1-4alkylene as generally defined above.

[0032] As used herein, the term "C1-4alkylsulfanyl" refers to a radical of the formula RaS-, where Ra is a C1-4alkyl radical as generally defined above.

[0033] As used herein, the term "C1-4alkylsulfonyl" refers to a radical of the formula RaS(O)2-, where Ra is a C1-4alkyl radical as generally defined above.

[0034] As used herein, the term "C1-4alkylsulfanylC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a C1-4alkylsulfanyl group as defined above.

[0035] As used herein, the term "C1-4alkylsulfonylC1-4alkyl", refers to a C1-4alkyl radical as generally defined above substituted with a C1-6alkylsulfonyl group as defined above.

[0036] As used herein, the term "N-C1-4alkylamino" refers to a radical of the formula RaNH- where Ra is a C1-4alkyl radical as generally defined above.

[0037] As used herein, the term "N,N-diC1-4alkylamino" refers to a radical of the formula Ra(Ra)N- where Ra is a C1-4alkyl radical as generally defined above.

[0038] As used herein, the term "C1-4haloalkoxy" refers to a C1-4alkoxy group as defined above substituted by one or more of the same or different halogen atoms. Examples of C1-4haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, 2-fluoroethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy.

[0039] As used herein, the term "haloC1-4alkoxy-C1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a haloC1-4alkoxy group as defined above.

[0040] As used herein, the term "aminoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted by one or more amino groups as defined above.

[0041] As used herein, the term "C1-4alkylcarbonylC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a C1-4alkylcarbonyl group as defined above.

[0042] As used herein, the term "C1-4alkylcarbonylC2-4alkenyl" refers to a C2-4alkenyl radical as generally defined above substituted with a C1-4alkylcarbonyl group as defined above.

[0043] As used herein, the term "N-C1-4alkylaminocarbonyl" refers to a radical of the formula RaNHC(O)- where Ra is a C1-4alkyl radical as generally defined above.

[0044] As used herein, the term "N-C1-4alkylaminocarbonylC1-4alkyl" refers to a radical of the formula RaNHC(O)Rb- where each Ra is a C1-4alkyl radical as generally defined above, and Rb is a C1-4alkylene radical as generally defined above.

[0045] As used herein, the term "N,N-diC1-4alkylaminocarbonyl" refers to a radical of the formula (Ra)RaNC(O)- where each Ra is independently a C1-4alkyl radical as generally defined above .

[0046] As used herein, the term "N,N-diC1-4alkylaminocarbonylC1-4alkyl" refers to a radical of the formula (Ra)RaNC(O)Rb- where each Ra is independently a C1-4alkyl radical as defined in general above, and Rb is a C1-4alkylene radical as generally defined above.

[0047] As used herein, the term "N-C1-4alkylaminoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with an N-C1-4alkylamino group as defined above.

[0048] As used herein, the term "N,N-diC1-4alkylaminoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a N,N-diC1-4alkylamino group as defined above.

[0049] As used herein, the term "C1-4alkylsulfonylamino" refers to a radical of the formula -NHS(O)2Ra where Ra is a C1-4alkyl radical as generally defined above.

[0050] As used herein, the term "C1-4alkylsulfonylaminoC1-4alkyl", refers to a C1-4alkyl radical as defined generally above substituted with a C1-4alkylsulfonylamino group as defined above.

[0051] As used herein, the term "C1-4alkylcarbonylamino" refers to a radical of the formula -NHC(O)Ra where Ra is a C1-4alkyl radical as generally defined above.

[0052] As used herein, the term "C1-4alkylcarbonylaminoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a C1-4alkylcarbonylamino group as defined above.

[0053] As used herein, the term "C1-4alkoxycarbonylamino" refers to a radical of the formula -NHC(O)ORa where Ra is a C1-4alkyl radical as generally defined above.

[0054] As used herein, the term "C1-4alkoxycarbonylaminoC1-4alkyl" refers to a C1-4alkyl radical as generally defined above substituted with a C1-4alkoxycarbonylamino group as defined above.

[0055] As used herein, the term "C3-6cycloalkyl" refers to a stable monocyclic ring radical that is saturated or partially saturated and contains 3 to 6 carbon atoms. C3-5cycloalkyl and C3-4cycloalkyl are to be interpreted accordingly. Examples of C3-6cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl and cyclohexen-3-yl.

[0056] As used herein, the term "C3-6cycloalkylC1-2alkyl" refers to a C3-6cycloalkyl ring as defined above attached to the remainder of the molecule by a C1-2alkylene radical as defined above. Examples of C3-6cycloalkylC1-3alkyl include, but are not limited to, cyclopropylmethyl and cyclobutylethyl.

[0057] As used herein, the term "phenylC1-2alkyl" refers to a phenyl ring attached to the rest of the molecule by a C1-2alkylene radical as defined above. Examples of phenylC1-2alkyl include, but are not limited to, benzyl.

[0058] As used herein, the term "heteroaryl" generally refers to a radical of a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 individually selected heteroatoms of nitrogen, oxygen and sulfur. The heteroaryl radical may be attached to the rest of the molecule via a carbon atom or a heteroatom. Examples of heteroaryl include, but are not limited to, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, pyridyl, and indolyl.

[0059] As used herein, the term "heterocyclyl" or "heterocyclic" refers to a stable, saturated or partially saturated, 4- to 6-membered, non-aromatic monocyclic ring comprising 1, 2 or 3 selected heteroatoms individually of nitrogen, oxygen and sulfur. The heterocyclyl radical may be attached to the remainder of the molecule via 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.

[0060] 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, ie 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 these possible isomeric forms and mixtures thereof for a compound of Formula (I). Likewise, Formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) when present. The present invention includes all possible tautomeric forms for a compound of Formula (I).

[0061] In each case, the compounds of Formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g. e.g., in an agronomically usable or agrochemically acceptable salt form.

[0062] 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.

[0063] The following list provides definitions, including preferred definitions, for substituents A1, A2, A3, A4, R1, R2, R3, R4, R5, R6, R7, Z (including Z1, Z2, Z3, Z4, Z5), R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 and R20, 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.

[0064] A1 represents C-R1, wherein R1 is hydrogen or halogen; A2 represents C-R2, wherein R2 is hydrogen or halogen; A3 represents C-R3, wherein R3 is hydrogen or halogen; and A4 represents C-R4, wherein R4 is hydrogen or halogen; wherein 0, 1 or 2 of A1, A2, A3 and A4 is C-halogen. In particular, the halogen can be fluorine or chlorine.

[0065] In certain embodiments of the invention, A1, A2, A3 and A4 are C-H; A2, A3 and A4 are C-H and A1 is C-F; A1, A2 and A4 are CH and A3 is C-F; A1 and A2 are C-F and A3 and A4 are C-H; A1 and A3 are C-F and A2 and A4 are C-H, or A1 and A2 are C-H and A3 and A4 are C-F. Preferably, A1, A2, A3 and A4 are C-H.

[0066] R5 and R6 independently represent hydrogen or methyl; Preferably, R5 and R6 are both hydrogen or R5 is hydrogen and R6 is methyl. More preferably, R5 and R6 are both hydrogen.

[0067] R7 represents C1-4haloalkoxy. In particular, R7 may represent C1-4fluoroalkoxy or C1-4chloroalkoxy. Preferably, R7 is C1-4fluoroalkoxy. More preferably, R7 is C1-3fluoroalkoxy. Even more preferably, R7 is C1-2fluoroalkoxy, in particular fluoromethoxy, 2-fluoroethoxy or 2,2-difluoroethoxy.

[0068] R7 can be selected from O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl), O-(2,2,2-trifluoroethyl), O-(2,2,3,3,3-pentafluoropropyl),O-(2-fluoropropyl), O-(2,2-difluoropropyl), O-(4-fluorobutyl), O-(4,4-difluorobutyl ) or O-(4,4,4-trifluorobutyl).

[0069] Z is Z1, Z2, Z3, Z4 or Z5. In certain embodiments of the invention, Z is Z1; or Z is Z2; or Z is Z3; or Z is Z4; or Z is Z5. Preferably, Z is Z1 or Z is Z3.

[0070] Z1 represents -C(O)R8, where R8 represents hydrogen, cyano, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, cyanoC1-4alkyl, C1-4haloalkyl, C2-6haloalkenyl, hydroxyC1-4alkyl, C1- 4alkoxyC1-4alkyl, C1-4haloalkoxyC1-4alkyl, C1-2alkoxyC1-2alkoxyC1-4alkyl, C2-4alkynyloxyC1-4alkyl, aminoC1-6alkyl, N-C1-4alkylaminoC1-4alkyl, N,N-diC1-4alkylaminoC1-4alkyl, C1-4alkyl carbonylC1- 4alkyl, C1-4alkylcarbonylC2-4alkenyl, C1-4alkoxycarbonylC1-4alkyl, C1-4alkylcarbonyloxyC1-4alkyl, N-C1-4alkylaminocarbonylC1-4alkyl, N,N-diC1-4alkylaminocarbonylC1-4alkyl, C1-4alkylsulfanylC1-4alkyl, C1- 4alkylsulfonylC1-4alkyl, C1-4alkylsulfonylaminoC1-4alkyl, C1-4alkylcarbonylaminoC1-4alkyl, C1-4alkoxycarbonylaminoC1-4alkyl; or

[0071] R8 represents C3-6cycloalkyl, C3-6cycloalkylC1-2alkyl, phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, 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, wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9.

[0072] R9 represents cyano, halogen, hydroxy, amino, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4haloalkyl, C1-4alkoxy, C1-4haloalkoxy, C3-4alkenyloxy, C3-4alkynyloxy, N-C1-4alkylamino , N,N-diC1-4alkylamino, C1-4alkylcarbonyl, C3-6cycloalkylcarbonyl, C1-4alkoxycarbonyl, carbonylamino, N-C1-4alkylaminocarbonyl, N,N-diC1-4alkylaminocarbonyl, C1-4alkoxycarbonylamino or C1-4alkylsulfonyl, and wherein when R8 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2;

[0073] Preferably, R8 is selected from C1-6alkyl, C1-4haloalkyl, C1-4alkoxyC1-4alkyl, C1-4alkylcarbonylaminoC1-4alkyl. More preferably, R8 is selected from C1-4alkyl, C1-2haloalkyl, C1-2alkoxyC1-3alkyl, C1-2alkylcarbonylaminoC1-2alkyl.

[0074] Preferably, R8 is selected from C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, phenyl or heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 heteroatom selected from N, O and S , wherein the cycloalkyl, phenyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9.

[0075] More preferably, R8 is selected from cyclopropyl, cyclobutyl, cyclopropylmethyl, phenyl, oxetanyl (oxetan-2-yl, oxetan-3-yl), tetrahydrofuranyl (tetrahydrofuran-2-yl, tetrahydrofuran-3 -yl) or tetrahydropyranyl (tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl), optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9, wherein R9 is cyano, halogen, hydroxy, amino, methyl, methoxy. Even more preferably, R8 is selected from cyclopropyl or phenyl, optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9, wherein R9 is cyano, fluoro, chloro, hydroxy, amino, methyl, methoxy. Even more preferably, R8 is selected from cyclopropyl or phenyl, optionally substituted by 1 or 2 substituents selected from R9, wherein R9 is chloro or fluoro.

[0076] Z2 represents -C(O)OR10, where R10 represents hydrogen, C1-4alkyl, C3-5alkenyl, C3-5alkynyl, C1-3haloalkyl, C1-3alkoxyC2-4alkyl or R6 represents C3-6cycloalkyl or C3-6cycloalkylC1- 2alkyl, where for R10, any cycloalkyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R11. Preferably, R10 is hydrogen or C1-4alkyl.

[0077] R11 represents cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy.

[0078] Z3 represents -C(O)NR12R13, where R12 represents hydrogen, cyano, C1-4alkyl, C1-4alkoxy, C3-5alkenyl, C3-5alkynyl, C3-4alkenyloxy, C3-4alkynyloxy, cyanoC1-3alkyl, C1- 3haloalkyl, C3-4haloalkenyl, hydroxyC2-4alkyl, C1-2alkoxyC2-4alkyl, C1-2haloalkoxyC2-4alkyl, C1-2alkoxyC2-4alkoxyC2-4alkyl, aminoC2-4alkyl, N-C1-4alkylaminoC2-4alkyl, N,N-diC1-4al chylaminoC2- 4alkyl, C1-3alkylcarbonylC1-3alkyl, C1-4alkoxycarbonylC1-3alkyl, C1-3alkylcarbonyloxyC2-4alkyl, N-C1-3alkylaminocarbonylC1-3alkyl, N,N-diC1-3alkylaminocarbonylC1-3alkyl, C1-3alkylsulfonyl, C1-3alkylsulfonylC2 -3alkyl, C1- 3alkylsulfonylaminoC2-3alkyl; or

[0079] R12 represents C3-6cycloalkyl, phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, 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; wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14.

[0080] Preferably, R12 is hydrogen, C1-4alkyl, C1-4alkoxy, cyanoC1-3alkyl, C1-3haloalkyl, hydroxyC2-4alkyl, C1-2alkoxyC2-4alkyl or C3-6cycloalkyl, wherein the cycloalkyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14. More preferably, R12 is hydrogen, C1-4alkyl, C1-4alkoxy or cyclopropyl, wherein cyclopropyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14.

[0081] R14 represents cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, propen-2-yl, propyn-2-yl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, propen-2-yloxy, propyn-2 -yloxy, N-methylamino, N,N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein when R12 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2;

[0082] Preferably, R14 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy and methylcarbonyl.

[0083] R13 represents hydrogen, halogen, methyl, ethyl, propyl, isopropyl, propen-2-yl, propyn-2-yl, cyclopropyl, cyclopropylmethyl. Preferably, R13 is hydrogen, methyl or ethyl.

[0084] In certain embodiments of Z3, R12 and R13 are independently selected from hydrogen, methyl, ethyl, propyl and iso-propyl and preferably, hydrogen, methyl and ethyl.

[0085] Unless otherwise indicated, R12 and R13, together with the nitrogen atom to which they are attached, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O )2 and NR15; wherein R15 is hydrogen, methyl, methoxy, formyl or acyl. Preferably, R12 and R13, together with the nitrogen atom to which they are attached, form a 5-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 nitrogen atoms. More preferably, R12 and R13, together with the nitrogen atom to which they are attached, form a pyrazolyl or imidazolyl ring.

[0086] Z4 represents -C(O)C(=R16)R17, wherein R16 represents O or N-methoxy. Preferably, R16 is O.

[0087] R17 represents hydrogen, cyano, amino, hydroxy, C1-4alkyl, C1-4alkoxy, C2-4alkenyl, C3-4alkenyloxy, C2-4alkynyl, C3-4alkynyloxy, cyanoC1-2alkyl, C1-2haloalkyl, C1-2haloalkoxy, hydroxyC1 -3alkyl, C1-2alkoxyC1-4alkyl, C1-2haloalkoxyC1-4alkyl, N-C1-3alkylamino, N,N-diC1-3alkylamino, N-C1-3alkoxyamino, N-C1-2alkoxy-N-C2-4alkylamino, N-C1 -2alkylaminoC1-3alkyl, N,N-diC1-2alkylaminoC1-3alkyl, or;R17 represents C3-4cycloalkyl, C3-4cycloalkylamino, C3-4cycloalkyloxy, heterocyclyl, 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; wherein the cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R18.

[0088] Preferably, R17 represents hydrogen, cyano, amino, hydroxy, C1-4alkyl, C1-4alkoxy, C1-2haloalkyl, hydroxyC1-3alkyl, C1-2alkoxyC1-4alkyl, N-C1-3alkylamino, N,N-diC1-3alkylamino , N-C1-3alkoxyamino or N-C1-2alkoxy-N-C2-4alkylamino. More preferably, R17 represents amino, N-C1-3alkylamino, N,N-diC1-3alkylamino, N-C1-3alkoxyamino or N-C1-2alkoxy-N-C2-4alkylamino.

[0089] R18 represents amino, hydroxyl, cyano, halogen, hydroxy, C1-4alkyl, allyl, propargyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, N-methylamino, N,N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N - methylaminocarbonyl, N,N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein where R17 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2.

[0090] Z5 represents -S(O)2R19, wherein R19 represents amino, C1-4alkyl, C3-5alkenyl, C3-5alkynyl, cyanoC1-4alkyl, C1-3haloalkyl, C1-2alkoxyC1-4alkyl, C1-2haloalkoxyC2-3alkyl, C1-3alkylcarbonylC1-3alkyl, C1-3alkoxycarbonylC1-3alkyl, C1-3alkylcarbonyloxyC2-4alkyl, N-C1-3alkylaminocarbonylC1-3alkyl, N,N-diC1-3alkylaminocarbonylC1-3alkyl, N-C1-3alkylamino, N,N-diC1-3alkylamino, N-C1-3alkoxyamino, N-C1-3alkoxy-N-C1-3alkylamino, N-C1-3alkylaminoC1-4alkyl, N,N-diC1-3alkylaminoC1-3alkyl, C1-3alkylcarbonylaminoC2-3alkyl, C1-3alkoxycarbonylaminoC2-3alkyl; or

[0091] R19 represents C3-6cycloalkyl, C3-4cycloalkylC1-2alkyl, phenyl, phenylC1-2alkyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, or heterocyclyl, 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, wherein cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R20.

[0092] Preferably, R19 is amino, C1-4alkyl, C3-4alkenyl, C3-4alkynyl, cyanoC1-2alkyl, C1-3haloalkyl, C1-2alkoxyC1-2alkyl, C1-2alkoxycarbonylC1-2alkyl, N-C1-2alkylamino, N,N -diC1-2alkylamino, N-C1-2alkoxyamino, N-C1-2alkoxy-N-C1-2alkylamino, or R19 is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, phenyl, phenylC1-2alkyl, heteroaryl, wherein the heteroaryl moiety is a 5-membered monocyclic aromatic ring comprising 1 or 2 heteroatoms which are nitrogen or 1 heteroatom which is O or S or heterocyclyl, wherein the heterocyclyl moiety is a non-aromatic 5-membered ring comprising 1 or 2 heteroatoms individually selected from N , O and S, wherein the cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R20.

[0093] More preferably, when R19 is C3-4cycloalkyl, C3-4cycloalkylC1-2alkyl, phenyl, phenylC1-2alkyl, heteroaryl or heterocyclyl, it is selected from cyclopropyl, cyclopropylmethyl, phenyl, benzyl, pyrazolyl, thienyl or pyrrolidinyl optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R20.

[0094] R20 represents cyano, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; and wherein when R19 is cycloalkyl or heterocyclyl, these cycles may optionally contain 1 group selected from C(O) or S(O)2.

[0095] Preferably, the compound according to Formula (I) is selected from a compound 1.1 to 1.4 listed in Table T1 (below), or a compound 2.1 to 2.2 listed in Table T2 (below).

[0096] Preferably, in a compound according to Formula (I) of the invention: A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3 and R4 are hydrogen; R5 is hydrogen and R6 is hydrogen or methyl; R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl), O-(2,2,2-trifluoroethyl), O-(2,2 ,3,3,3-pentafluoropropyl), O-(2,fluoropropyl), O-(2,2-difluoropropyl), O-(4,fluorobutyl), O-(4,4-difluorobutyl), or O-(4, 4,4-trifluorobutyl); or R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl), O-(2,2,2-trifluoroethyl), O-(2, fluoropropyl), O-(2,2-difluoropropyl), O-(4-fluorobutyl) or O-(4,4-difluorobutyl); or R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl) or O-(2,2,2-trifluoroethyl); Z is Z1, and R8 is cyclopropyl, cyclobutyl, cyclopropylmethyl, phenyl, oxetanyl (oxetan-2-yl, oxetan-3-yl), tetrahydrofuranyl (tetrahydrofuran-2-yl, tetrahydrofuran-3-yl) or tetrahydropyranyl (tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl), optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9, in that R9 is cyano, halogen, hydroxy, amino, methyl, methoxy.

[0097] More preferably, A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4, and R1, R2, R3 and R4 are hydrogen; R5 and R6 are hydrogen; R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl) or O-(2,2,2-trifluoroethyl); Z is Z1, and R8 is cyclopropyl, cyclobutyl, cyclopropylmethyl, phenyl, oxetanyl (oxetan-2-yl, oxetan-3-yl), tetrahydrofuranyl (tetrahydrofuran-2-yl, tetrahydrofuran-3-yl) or tetrahydropyranyl (tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl), optionally substituted with 1 substituent, selected from R9, wherein R9 is cyano, halogen, hydroxy, amino, methyl, methoxy.

[0098] Preferably, in a compound according to Formula (I) of the invention: A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3 and R4 are hydrogen; R5 is hydrogen and R6 is hydrogen or methyl; R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl), O-(2,2,2-trifluoroethyl), O-(2,2 ,3,3,3-pentafluoropropyl), O-(2,fluoropropyl), O-(2,2-difluoropropyl), O-(4,fluorobutyl), O-(4,4-difluorobutyl), or O-(4, 4,4-trifluorobutyl); or R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl), O-(2,2,2-trifluoroethyl), O-(2, fluoropropyl), O-(2,2-difluoropropyl), O-(4-fluorobutyl) or O-(4,4-difluorobutyl); or R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl) or O-(2,2,2-trifluoroethyl); Z is Z3; R12 is hydrogen, C1-4alkyl, C1-4alkoxy, cyanoC1-3alkyl, C1-3haloalkyl, hydroxyC2-4alkyl, C1-2alkoxyC2-4alkyl or C3-6cycloalkyl, wherein the cycloalkyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14, wherein R14 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy and methylcarbonyl; and R13 is hydrogen, methyl or ethyl;

[0099] More preferably, A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4, and R1, R2, R3 and R4 are hydrogen; R5 and R6 are hydrogen; R7 is O-(fluoromethyl), O-(difluoromethyl), O-(2-fluoroethyl), O-(2,2-difluoroethyl) or O-(2,2,2-trifluoroethyl); Z is Z3; R12 is hydrogen, C1-4alkyl, C1-4alkoxy or cyclopropyl, wherein the cycloalkyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R14, wherein R14 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy and methylcarbonyl; and R13 is hydrogen, methyl or ethyl;

[0100] The compounds of the present invention may be enantiomers of the compound of Formula (I) as represented by a Formula (Ia) or a Formula (Ib), wherein R5 and R6 are different substituents.

[0101] It is understood that, when in an aqueous medium, 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 (II) and the formula (I-II) as shown below, which may exist in tautomeric form as the compounds of formula (I-Ia) and formula (I-IIa)) in the CF3-oxadiazole motif. This dynamic equilibrium may be important for the biological activity of the compounds of Formula (I). The designations of A1, A2, A3, A4, R1, R2, R3, R4, R5, R6, R7, Z (including Z1, Z2, Z3, Z4, Z5), R8, R9, R10, R11, R12, R13 , R14, R15, R16, R17, R18, R19, R20, and R21, with reference to the compounds of formula (I) of the present invention, apply generally to compounds of Formula (II) and Formula (I-II) and (I-Ia) and (I-IIa), as well as specific disclosures of combinations of A1, A2, A3, A4, R1, R2, R3, R4, R5, R6, R7, Z (including Z1, Z2, Z3 , Z4, Z5), R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, and R21, as depicted for a compound 1.1 to 1.4 described in Table T1 (below) , a compound 2.1 or 2.2 described in Table T2 (below), or a compound of Formula (I) described in Tables 1.1 to 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5 or Tables 5.1 to 5.5 (below ).

[0102] The compounds of the present invention can be prepared as shown in the following schemes 1 to 21, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

[0103] The compounds of formula (Ia), in which Za is -R8, -NR12R13, or -C(=R16)R17, can be obtained by a coupling transformation of amides with compounds of formula (II), a process which usually occurs by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example using (COCl)2 or SOCl2, before treatment with the amine compounds of formula (III), preferably in a suitable solvent (for example, dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 °C and 100 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or under conditions described in the literature for an amide coupling. For examples see WO 2003/028729. The compounds of formula (II) 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. Res. Journal (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 1. scheme 1

[0104] The compounds of formula (Ib), in which Zb represents -OR10 or -N(R12)R13, can be prepared from compounds of formula (III) by treatment with triphosgene, diphosgene or phosgene, in a suitable solvent ( for example ethyl acetate, CHCl3 or toluene), optionally with heating between 25°C and 65°C, followed by the addition of suitable nucleophiles of formula (IV), in the presence of a suitable base, such as triethylamine. This reaction is shown in Scheme 2. scheme 2

[0105] The compounds of Formula (Ic), in which Zc is hydrogen, -C(O)R8, -C(O)NR12R13, -C(=R16)R17, or -S(O)2R19, can be prepared of compounds of formula (VI), in which X is a halogen, preferably Br or I, by treatment with compounds of formula (V) in the presence of a base (e.g. K2CO3, Cs2CO3, or NaH) in a suitable solvent ( for example, dimethylformamide or acetonitrile) at a temperature between 25 °C and 110 °C. For related examples, see: WO 1995/9518122 and Jpn. Kokai Tokkyo Koho, 1993, 05286936 . Compounds of formula (V) are commercially available or prepared using known methods. For related examples, see: Eur. Pat. scheme 3

[0106] The compounds of formula (Id), in which Zd is R19, can be obtained by a coupling transformation with compounds of formula (VII) and compounds of formula (III), in a suitable solvent (for example, dichloromethane) preferably at a temperature between 0°C and 25°C, in the presence of a base such as triethylamine or pyridine. For examples see WO 2012/068251 or Oshima, T. et al Angew. Chem., Int. Ed. (2015), 54, 7193. This reaction is shown in Scheme 4. scheme 4

[0107] Compounds of formula (VI), where X is halogen, preferably Br or I, can be prepared from compounds of formula (VIII) by treatment with a halogen source (e.g., N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator (eg, (PhCO2)2 or azobisisobutyronitrile (AIBN)) in a suitable solvent, such as tetrachloromethane, at temperatures between 55 °C and 100 °C in the presence of ultraviolet 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 5. scheme 5

[0108] Compounds of formula (VI), in which X is hydrogen or a halogen, preferably Br or I, can be prepared from compounds of formula (IX) by treatment with trifluoroacetic chloride, trifluoroacetic fluoride or trifluoroacetic anhydride in the presence of a base (for example, pyridine or 4-dimethylaminopyridine) in a suitable solvent, such as tetrahydrofuran or ethanol, at a temperature between 25 °C and 75 °C. For related examples see WO 2003/028729 and WO 2010/045251. This reaction is shown in Scheme 6. scheme 6

[0109] Compounds of formula (IX), in which X is hydrogen or a halogen, preferably Br or I, can be prepared from compounds of formula (X) by treatment with a hydroxylamine hydrochloride in the presence of a base, such as triethylamine, in a suitable solvent, such as methanol, at a temperature between 0 °C and 100 °C. For related examples see Kitamura, S. et al. chem. Pharm. Bull.(2001), 49, 268 and WO 2013/066838. This reaction is shown in Scheme 7. scheme 7

[0110] Compounds of formula (X) can be prepared from compounds of formula (XI), where Y is Br or I, by metal-promoted reaction with a suitable cyanide reagent, such as Pd(0)/Zn (CN)2 or CuCN, in a suitable solvent (eg dimethylformamide or N-methylpyrrolidone) at elevated temperature between 100 °C and 120 °C. For related examples see US 2007/0155739 and WO 2009/022746. This reaction is shown in Scheme 8. scheme 8

[0111] Compounds of formula (XI) where X is Cl, Br, I or OSO2Me and Y is Br, I or CN are commercially available or can be prepared from compounds of formula (XII) by treatment with a halogen source (eg CCl3Br, CCl4 or I2) in the presence of triphenylphosphine or with methanesulfonyl chloride (ClSO2Me) in a suitable solvent (eg dichloromethane) at a temperature 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 (XII) are commercially available. This Scheme 9. scheme 9

[0112] Compounds of formula (III) can be prepared from compounds of formula (XIII) by treatment with trifluoroacetic chloride, trifluoroacetic fluoride or trifluoroacetic anhydride in the presence of a base (for example, pyridine or 4-dimethylaminopyridine) in a suitable solvent , such as tetrahydrofuran or ethanol, at a temperature between 25°C and 75°C. For related examples see WO 2003/028729 and WO 2010/045251. This reaction is shown in Scheme 10. scheme 10

[0113] The compounds of formula prepared from compounds of formula (XIV) by treatment with a hydroxylamine hydrochloride in the presence of a base, such as triethylamine, in a suitable solvent, such as methanol, at a temperature between 0°C and 100°C °C. For related examples see Kitamura, S. et al Chem. Pharm. Bull. (2001), 49, 268 and WO 2013/066838 . This reaction is shown in Scheme 11. Scheme 11

[0114] The compounds of formula (XIVa) can be obtained by a coupling transformation of amides with compounds of formula (II), in which Za is -R8, -NR12R13, or -C(=R16)R17, a process that usually occurs by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example using (COCl)2 or SOCl2, before treatment with the compounds of formula (III), preferably in a suitable solvent (e.g. example, dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 °C and 100 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or under conditions described in the literature for a amide coupling. For examples see WO 2003/028729. The compounds of formula (II) 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. Res. Journal (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 12. Scheme 12

[0115] Compounds of formula (XIVb), in which Zb represents -OR10 or N(R12)R13, can be prepared from compounds of formula (XV) by treatment with triphosgene, diphosgene or phosgene, in a suitable solvent (for (e.g., ethyl acetate, CHCl3 or toluene) with heating between 65°C and 100°C, followed by the addition of suitable nucleophiles of formula (IV) in the presence of a suitable base, such as triethylamine. This reaction is shown in Scheme 13. Scheme 13

[0116] The compounds of formula (XIVc), in which Zc is hydrogen, -C(O)R8, -C(O)NR12R13, -C(=R16)R17, or -S(O)2R19, can be prepared of compounds of formula (XV), in which X is a halogen, preferably Br or I, by treatment with compounds of formula (V) in the presence of a base (e.g. K2CO3, Cs2CO3, or NaH) in a suitable solvent ( for example, dimethylformamide or acetonitrile) at a temperature between 25 °C and 110 °C. For related examples, see: WO 1995/9518122 and Jpn. Kokai Tokkyo Koho, 1993, 05286936 . Compounds of formula (V) are commercially available or prepared using known methods. For related examples, see: Eur. Pat. Appl., 1989, 318933. This reaction is shown in Scheme 14. Scheme 14

[0117] The compounds of formula (XIVd), in which Zd is R19, can be obtained by a coupling transformation with compounds of formula (VII) and compounds of formula (XV), in a suitable solvent (for example, dichloromethane) preferably at a temperature between 0°C and 25°C, and optionally in the presence of a base such as triethylamine or pyridine, or under conditions described in the literature for an amide coupling. For examples see WO 2012/068251 or Oshima, T. et al Angew. Chem., Int. Ed. (2015), 54, 7193. This reaction is shown in Scheme 15. Scheme 15

[0118] Compounds of formula (Ia), in which Za is -R8, -NR12R13, or -C(=R16)R17, can be prepared from compounds of formula (XVII), in which X is a halogen, preferably Br or I, and R21 is C1-4haloalkyl by treatment with compounds of formula (XVI), in the presence of a base (for example K2CO3, Cs2CO3, or NaH) in a suitable solvent (for example, dimethylsulfoxide, dimethylformamide or acetonitrile) to a temperature between 25 °C and 110 °C. For related examples see: EP 0333154A2. Compounds of formula (XVII) are commercially available. This reaction is shown in Scheme 16. Scheme 16

[0119] The compounds of formula (XVI), in which Za is -R8, -NR12R13 or -C(=R16)R17, can be obtained by a coupling transformation of amides with compounds of formula (II), a process which usually occurs by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example using (COCl)2 or SOCl2, before treatment with the compounds of formula (XVIII), preferably in a suitable solvent (e.g. example, dimethylformamide, dichloromethane or tetrahydrofuran), at a temperature between 25 °C and 100 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or under conditions described in the literature for a coupling of amide. This reaction is shown in Scheme 17. Scheme 17

[0120] Compounds of formula (XVIII) can be prepared from compounds of (XIX) by treatment with an acid (HCl, HBr, H2SO4, or TFA) in a suitable solvent, (e.g. dichloromethane, trichloromethane ) at a temperature between 25 °C and 80 °C. This reaction is shown in Scheme 18. Scheme 18

[0121] The compounds of formula (XIX) can be prepared from compounds of formula (VI), in which X is a halogen, preferably Br or I, by treatment with compounds of formula (XX) in the presence of a base (eg K2CO3, Cs2CO3, or NaH) in a suitable solvent (eg dimethylformamide or acetonitrile) at a temperature between 25°C and 110°C. This reaction is shown in Scheme 19. Scheme 19

[0122] The compounds of formula (Id), in which Zd is R19, can be prepared from compounds of (XVII), in which X is a halogen, preferably Br or I, and R21 is C1-4haloalkyl by treatment with compounds of formula (XXI), in the presence of a base (for example K2CO3, Cs2CO3, or NaH) in a suitable solvent (for example, dimethylsulfoxide, dimethylformamide or acetonitrile) at a temperature between 25 °C and 110 °C. Compounds of formula (XVII) are commercially available. This reaction is shown in Scheme 20. Scheme 20

[0123] The compounds of formula (XXI), in which Zd is R19, can be obtained by a transformation of compounds of formula (VII) and compounds of formula (XVIII), in a suitable solvent (for example, dichloromethane) preferably to a temperature between 0°C and 25°C, in the presence of a base such as triethylamine or pyridine. For examples see WO 2012/068251 or Oshima, T. et al Angew. Chem., Int. Ed. (2015), 54, 7193. This reaction is shown in Scheme 21. Scheme 21

[0124] 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 the protection of plants against diseases that are caused by fungi.

[0125] The compounds of Formula (I) can be used in the agricultural sector and related areas of use, e.g. eg, as active ingredients to control plant pests or in non-living materials for the control of spoilage-causing microorganisms or organisms potentially harmful to humans. The new compounds are distinguished by their excellent activity at low application rates, because they are well tolerated by plants and because they are 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. The 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 crops of useful plants, while also protecting those parts of plants which grow later, p. e.g., phytopathogenic microorganisms.

[0126] 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 treating 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, parts thereof or locus thereof.

[0127] 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 "fungicidally effective amount", when used, means that amount of such compound or combination of such compounds which is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural development, such as killing, retarding and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.

[0128] It may also be possible to use compounds of Formula (I) as curative agents for the treatment of plant propagation material, for example seeds, such as fruits, tubers or grains, or plant cuttings, for protection against infections fungi, as well as against phytopathogenic fungi that occur in the soil. Propagation material can be treated with a composition comprising a compound of Formula (I) before planting: a seed, for example, can be treated before it is sown. The active compounds of Formula (I) can also be applied to grain (coating) by soaking the seeds in a liquid formulation or 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 also relates to such methods of treating plant propagation material and the plant propagation material so treated.

[0129] Additionally, the compounds of Formula (I) can be used to control fungi in related areas, for example, in the protection of technical materials, including wood and technical products related to wood, in food storage, in hygiene management.

[0130] Additionally, the invention could be used to protect non-living materials from fungal attack, e.g. e.g. lumber, wall paneling and paint.

[0131] The compounds of Formula (I) are, for example, effective against fungi and fungal disease vectors, as well as plant pathogenic bacteria and viruses. These fungi and fungal disease vectors, as well as phytopathogenic bacteria and viruses are, for example: Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii , 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, Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, 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. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, 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.

[0132] The compounds of Formula (I) can be used for example in peat, ornamental plants such as flowers, shrubs, broadleaf or evergreen trees, for example conifers, as well as for tree injection, pest management and the like .

[0133] Within the scope of the present invention, target crops and/or useful plants to be protected typically comprise perennial and annual crops such as berries, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (maize), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, for example Bermuda grass, blue grass, agrostis, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; aromatic herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes, for example beans, lentils, peas and soybeans; hard shell fruits, for example almond, cashew, peanut kernel, hazelnut, groundnut, pecan, pistachio and walnut; palms, for example palm oil; ornamental plants, for example flowers, shrubs and trees; other trees, for example cocoa, coconut, olive and rubber; vegetables, for example asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, squash, rhubarb, spinach and tomato; and vines, for example grapes.

[0134] The term "useful plants" should be understood to also 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-pyrovil-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors) as a result of conventional methods of improvement or modification genetics. An example of a crop that has been made tolerant to imidazolinones, e.g. ex. 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 engineering methods include glyphosate and glufosinate resistant maize varieties commercially available under the trademarks RoundupReady®, Herculex I® and LibertyLink®.

[0135] The term "useful plants" should be understood to also include useful plants that have been so transformed by the use of recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as are known, for example , from bacteria that produce toxins, especially those of the genus Bacillus.

[0136] Examples of such plants are: YieldGard® (maize variety expressing a CryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylIIB(bl) 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 expressing a CryIA(c) toxin); Bollgard I® (cotton variety expressing a CryIA(c) toxin); Bollgard II® (cotton variety that expresses a CryIA(c) toxin and a CryIIA(b) toxin); VIPCOT® (cotton variety expressing a VIP toxin); NewLeaf® (potato variety that expresses a CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA2l glyphosate tolerance trait), Agrisure® CB Advantage (Btll corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta® .

[0137] The term "cultures" is to be understood to also include cultured plants that have been so transformed by the use of recombinant DNA techniques, which are capable of synthesizing one or more selectively acting toxins, such as are known for example from bacteria toxin producers, especially those of the genus Bacillus.

[0138] Toxins that may 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 CrylAl, CrylAc, CrylF, Cry1Fa2, Cry2Al, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. g., Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; animal-produced toxins, 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 bluebell lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP) such as ricin, maize RIP, abrin, 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, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0139] Additionally, in the context of the present invention, are to be understood by δ-endotoxins, for example CrylAl, CrylAc, CrylF, CrylFa2, Cry2Al, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A, also expressly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by a novel combination of different domains of these proteins (see eg WO 02/15701). Truncated toxins, for example a truncated Cry1Ab, are known. In the case of engineered toxins, one or more amino acids in the naturally occurring toxin are replaced. In such amino acid substitutions, preferably recognition sequences for proteases not naturally present 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 ).

[0140] 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.

[0141] Processes for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the Cryl type 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.

[0142] 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 especially commonly found in beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0143] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety expressing a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab 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 expressing a Cry1Ac toxin); Bollgard I® (cotton variety expressing a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A toxin and a Cry1Ab); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) tolerant trait), and Protecta®. Additional examples of such transgenic crops are:

[0144] 1. Maize Bt11 from Syngenta Seeds SAS, Chemin 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. The Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the ammonium glufosinate herbicide.

[0145] 2. Maize Bt176 from Syngenta Seeds SAS, Chemin 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. The Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the ammonium glufosinate herbicide.

[0146] 3. Maize MIR604 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize 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 maize plants is described in WO 03/018810.

[0147] 4. More 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 Coleopteran insects.

[0148] 5. Cotton IPC 531 from Monsanto Europe S.A. 270272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.

[0149] 6. Mais 1507 Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. More genetically modified for the expression of the Cry1F protein to achieve resistance to certain Lepidoptera insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

[0150] 7. More 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. It consists of hybrid maize varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. Maize NK603 x MON 810 transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium sp., which confers tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. Kurstaki which confers tolerance to certain Lepidoptera, including the European corn borer.

[0151] The compounds of Formula (I) (including any compound described in Tables 1.1 to 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5 or Tables 5.1 to 5.5, or a compound 1.1 to 1.4 described in Table T1 (below) or a compound 2.1 or 2.2 described in Table T2 (below) can be used in the control or prevention of phytopathogenic diseases, especially of phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

[0152] In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, for example Cry1Ac (Bt protein Cry1Ac). Accordingly, this may include transgenic soybean plants comprising event MON87701 (see US Patent No. 8,049,071 and related patent applications, as well as WO 2014/170327 A1 (see, for example, paragraph [008] reference the Intact RR2 PROTM soybean)), event MON87751 (US Patent Application Publication No. 2014/0373191) or event DAS-81419 (US Patent No. 8632978 and related patent applications).

[0153] Other transgenic soybean plants may comprise event SYHT0H2 - tolerance to HPPD (US Patent Application Publication No. 2014/0201860 and related patent applications), event MON89788 - tolerance to glyphosate (US Patent No. Event MON87708 - Dicamba Tolerance (U.S. Patent Application Publication No. US 2011/0067134 and Related Patents and Applications), Event DP-356043-5 - Glyphosate and ALS Tolerance (US Patent Application Publication No. US 2010/0184079 and related patent applications), event A2704-12 - glufosinate tolerance (US Patent Application Publication No. US 2008/0320616 and related patent applications and ), event DP-305423-1 - ALS tolerance (US Patent Application Publication No. US 2008/0312082 and related patent applications), event A5547-127 - glufosinate tolerance (US Patent Application Publication No. No. US 2008/0196127 and related applications and patents), event DAS-40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011/022469, WO 2011/022470, WO 2011/022471, and related patents and applications), event 127 - ALS tolerance (WO 2010/080829 and related patents and applications), event GTS 40-3-2 - glyphosate tolerance, event DAS-68416-4 - acid tolerance 2,4 - dichlorophenoxyacetic acid and glufosinate, event FG72 - tolerance to glyphosate and isoxaflutol, event BPS-CV127-9 - tolerance to ALS and GU262 - tolerance to glufosinate, or event SYHT04R - tolerance to HPPD.

[0154] The term “locus” as used herein means fields in or over which plants are growing or where seeds of cultivated plants are sown or where seeds will be placed in the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0155] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[0156] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts may be mentioned. Germinated plants and young plants, which must be transplanted after germination or after emergence from the soil, can also be mentioned. These young plants can be protected before transplanting by means of a total or partial immersion treatment. Preferably, "plant propagation material" is understood to denote seeds.

[0157] The compounds of Formula (I) can be used in an unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. For this purpose, they can be conveniently formulated in known manner into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, e.g. e.g., in polymeric substances. As with the type of compositions, methods of application, such as spraying, atomizing, dusting, dispersing, coating or pouring, are chosen in accordance with the intended purposes and the prevailing circumstances. The compositions may also contain additional adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers, as well as fertilizers, micronutrient donors or other formulations to obtain special effects.

[0158] Carriers and adjuvants suitable, for example, for agricultural use, can be solid or liquid and are useful substances 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.

[0159] 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. In use, these concentrates are diluted with water and normally 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.

[0160] Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient trapped in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clays, silicas and other readily wetted organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0161] Emulsifiable 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 non-volatile organic solvents. In use, these concentrates are dispersed in water or another liquid and normally 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.

[0162] Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clay, bentonite clays, montmorillonite clays, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, sawdust, cobs ground corn kernels, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum , diatomaceous earth, 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.

[0163] Powders are free-flowing mixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids that act as dispersants and carriers.

[0164] Microcapsules are typically droplets or granules of the active ingredient surrounded by an inert porous capsule that allows the release of the contained material into the surrounding environment at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The contained liquid typically constitutes 50 to 95% of the weight of the capsule and may include a solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form within the granule pores. Granules typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter. Granules are formed by extrusion, agglomeration or pelletizing or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular coal. Casing or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0165] Other useful formulations 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 sprayers, in which the active ingredient is dispersed in a finely divided form as a result of vaporizing a low boiling point dispersant solvent carrier, can also be used.

[0166] 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.

[0167] Liquid carriers that may be employed include, for example, water, toluene, xylene, petroleum naphtha, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone , chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, ether diethylene glycol methyl ether, N,N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 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, isobornyl acetate, iso-octane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methylisoamylketone, methylisobutylketone, 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, ether monoethyl propylene glycol, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and molecular weight alcohols high, 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.

[0168] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, bark cottonseed flour, wheat flour, soy flour, pumice stone, wood flour, nut shell flour and lignin.

[0169] A wide variety of surfactants are advantageously employed in both said liquid and solid compositions, particularly those designed to be diluted with the carrier prior to application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, nonionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surfactants include alkyl sulfate salts, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol alkylene oxide addition products such as nonylphenol ethoxylate C.sub. 18 of nonylphenol; alcohol alkylene oxide addition products such as tridecyl alcohol ethoxylate C.sub. 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; ethylene oxide and propylene oxide block copolymers; and salts of mono- and dialkyl phosphate esters.

[0170] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light blocking agents, compatibilizing agents, antifoaming agents , sequestering agents, neutralizing agents and buffers, corrosion inhibitors, colorants, flavorings, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesive agents.

[0171] Furthermore, additionally, other biocidal active ingredients or compositions may 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 together, for example, in the spray tank. These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.

[0172] Reference is made here to pesticide agents using their common name, known for example from “The Pesticide Manual”, 15th Edition, British Crop Protection Council 2009.

[0173] 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 US Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0174] The compounds of Formula (I) are normally used in the form of agrochemical compositions, and can be applied to the crop area or plant to be treated, simultaneously or successively with additional compounds. These additional compounds can be e.g. ex. 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 additional carriers, surfactants or application-promoting adjuvants, commonly used in the formulation technique.

[0175] The compounds of Formula (I) can be used in the form of compositions (fungicides) to control or protect against phytopathogenic microorganisms, comprising as active ingredient at least one compound of Formula (I) or at least one preferred individual compound such as defined herein, in free form or in agrochemically usable salt form, and at least one of the aforementioned adjuvants.

[0176] 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 acceptable agricultural conveyor is, for example, a conveyor which is suitable for agricultural use. Agricultural conveyors are well known in the art. Preferably, said composition may comprise at least one or more pesticidally active compounds, for example an additional fungicidal active ingredient in addition to the compound of Formula (I).

[0177] The compound of Formula (I) may be the sole active ingredient of a composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator, where appropriate . An additional active ingredient can, in some cases, result in unexpected synergistic activities.

[0178] 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, arylphenylketone fungicides, benzamide fungicides, fungicides benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, diphenyl bridging fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, oragnophosphorus fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, 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, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0179] Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4 -methane-naphthalen-5-yl)-amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]- amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1), 1- methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl-3-difluoromethyl-4H-pyrazole-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-methyl-prop-2-en-(E)-ylideneaminoxymethyl]-phenyl}-2-[(Z)-methoxymino]-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-methoxyiminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide, α-[N-(3-chloro-2,6-xylyl)-2- methoxyacetamido]-y-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-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)-propan-2-ol, 2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 1-imidazolyl-1-(4'-chlorophenoxy)-3,3-dimethylbutan-2-one, (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3- methyl methoxyacrylate, (E)-methyl 2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxymethylacrylate, (E)-2-[2-[6-(2 - methyl fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate Methyl, (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxymethylacrylate, (E)-2-[2-[3-(5-methylpyrimidin-2) Methyl-yloxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(phenylsulfonyloxy)phenoxy]phenyl-3-methoxyacrylate, (E)-2-[2 Methyl-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, (E)-2-[2-(3, Methyl 5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, (E)-2[2- Methyl (2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, (E)-methyl 2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, (E methyl)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate, (E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy) methyl]phenyl)-3-methoxyacrylate, (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxymethylacrylate, (E)-2-[2-(3-n Methyl-propyloxy-phenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxy-methylacrylate, (E)-2-[2-[3-(2) Methyl -fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-(4-tert) methyl-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, (E)-methyl 2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)- Methyl 2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy Methyl]phenyl]-3-methoxyacrylate, (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxymethylacrylate, (E)-2-[2-(3 Methyl-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl] Methyl-3-methoxyacrylate, (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate, (E)-2-{2-[ Methyl 6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate, (E),(E)-2-{ 2-(3-methoxyphenyl)methyloximinomethyl]-phenyl Methyl }-3-methoxyacrylate, (E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxymethylacrylate, (E),(E)-2 -{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methyl methoxyacrylate, (E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl} Methyl-3-methoxyacrylate, (E)-methyl 2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate, (E ),(E)-methyl 2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate, 3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3 -en-5-yne), 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, 3-iodo-2-propynyl n-butylcarbamate, 3-iodo- 2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexylcarbamate, 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-dichlorothiazolinone, 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, allicin, allyl alcohol, ametoctradin, amisulbrom, amobam, ampropylphos, anilazine, asomate , aureofungin, azaconazole, azafendin, azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, bentiavalicarb, benthiazole, benzalkonium chloride, benzamacryl, benzamorph, benzohydroxamic acid, benzovindiflupyr, berberine, betoxaz ina, biloxazole, binapacryl, biphenyl, bitercanol, bithionol, bixafen, blasticidin-S, boscalid, bromotalonil, bromuconazole, bupirimate, butiobate, calcium polysulfide butylamine, captafol, captan, carbamorf, carbendazim, carbendazim hydrochloride, carboxin, carpropamid, carvone, CGA41396 , CGA41397, cynomethionate, cytosan, clobenthiazone, chloraniformethane, chloranil, chlorphenazole, chloroneb, chloropicrin, chlorothalonil, chlorozolinate, clozolinate, climbazole, clotrimazole, clozilacon, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, sodium naphthenate copper, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper talate, zinc copper chromate and Bordeaux mixture, cresol, cufraneb, cuprobam, cupridic oxide cyazofamid, cyclafuramide, cyclo- heximide, cyflufenamide, cymoxanil, cipendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, disulfidedi-2-pyridyl 1,1'-dioxide, dichlofluanid, diclomezin, dyclone, dichloran, dichlorofen, dichlozoline, diclobutrazol, diclocymet, dietofencarb , difenoconazole, difenzoquat, diflumetorim, O,O-diisopropyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimetconazole, dimethomorph, dimetirimol, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, disulfiram,ditalymphs, ditianon, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin, dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole, etaconazole, etem, ethanboxam, ethirimol, ethoxyquin, ethylicin, (Z)- Ethyl N-benzyl-N([methyl(methylthioethylideneaminooxycarbonyl)amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone, phenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamide, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorf, flupicolide, fluopyram, fluorimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fuberidazole, furalaxyl, furamethpyr, furcarbanil, furconazole, furfural, furmecyclox, furophanate, gliodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydrargafen, hydroxyisoxazole, hymexazol, imazalil, imazalil sulfate, imibeconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole, iprobenphos, iprodione, iprovalicarb, isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isothianyl, isovaledione, isopamphos, kasugamycin, kresoxim-methyl, LY18 6054, LY211795, LY248908, mancozeb , mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methansulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, methiram, methiramzinc, metominostrobin, metraphenone, metsulfovax, milneb, moroxidine, myclobutanil, myclozolin, nabam, natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene, nitrothalisopropyl, nuarimol, octilinone, ofurace, organomercury compounds, orysastrobin , ostol, oxadixyl, oxasulfuron, oxathiapiprolin, oxine-copper, oxoinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, fenamacryl, phenazine phosdiphene oxide, fosetyl-Al, phosphorus acid, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxyn D, polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazid, prothiocarb, prothioconazole, pidiflumetofen, piracarbolid, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos, piribencarb , pyridinitril, pyrifenox, pyrimethannil, pyriophenone, pyroquilon, piroxychlor, piroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinacetol, quinazamid, quiconazole, quinomethionate, quinoxyfen, quintazene, rabenzazole, santonin, sedaxane, silthiofam, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine , streptomycin, sulfur, sultropen, tebuconazole, tebfloquin, tecloftalam, technazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thiophene, tifluzamide, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thioquinox, tyram, tiadinil, timibeconazole, thioximid, tolclofos- methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin, zarilamid, zineb, ziram, and zoxamide.

[0180] The compounds of the invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the class of macrocyclic lactone compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, 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, oxibendazole, parbendazole and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include fluquicides, such as triclabendazole and clorsulon, and the cestocides, such as praziquantel and epsiprantel.

[0181] The compounds of the invention can be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as with antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE -19520936.

[0182] The compounds of the invention can be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents 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.

[0183] The compounds of the invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.

[0184] 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.

[0185] 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:

[0186] Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chloridexyphos, chloropyrifos, chlorfenvinphos, chloromephos, demetone, demetone-S-methyl, demetone-S-methylsulfone, dialiphos, diazinone , dichlorvos, dicrotophos, dimethoate, disulfotone, ethione, etoprofos, ethrymphos, fanfur, fenamiphos, fenitrothion, fensulfothione, fenthione, flupyrazophos, phonophos, formotiona, fostiazate, heptenofos, isazofos, isothioate, isoxathione, malathione, methacryphos, methamidophos, metidathione , methyl -parathion, mevinphos, monocrotophos, naled, omethoate, oxymetone-methyl, paraoxone, parathion, parathion-methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidone, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenophos, propaphos, proethanphos , prothiophos, pyraclophos, pyridapention, quinalphos, sulprofos, temephos, terbufos, tebupyrinphos, tetrachlorvinphos, timetone, triazophos, trichlorfon, vamidothion.

[0187] Carbamates: AlanCarb, Aldicarbe, 2-Secret MethylCarbamate, Benfuracarbe, Carbaril, Carbofuran, Carbosulphane, Cloetocarb, Etiofencarb, Fenoxycarbe, Furatiocarbe, HCN-801, Isopocarb, Indoxacarbe, Metomile, Metomy, Carbamate, 5 -methyl-m-cumenylbutyryl(methyl), oxamyl, pirimicarb, propoxur, thiodicarb, tiophanox, triazamate, UC-51717.

[0188] Pyrethroids: acrinatin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cytitrine, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, phenpropathrin, 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, tralometrine, Zetacypermethrin.

[0189] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorphentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0190] Other antiparasitics: acequinocil, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus turingiensis, Bensultape, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, canfechlor, cartap, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide , clothianidin, cyromazine, diaclodene, diafenthiuron, DBI-3204, dynactin, dihydroxymethyldihydroxypyrrolidine, dinobutone, dinocap, endosulfan, ethiprol, etofenprox, phenazaquine, flumite, MTI-800, fenpyroximate, fluacripyrim, flubenzimine, flubrocitrinate, flufenzin, flufenpro x , fluproxyfen, halofenprox, hydramethylnone, IKI-220, kanemite, NC-196, neem protectant, nidinorterfuran, nitanpyram, SD-35651, WL-108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidiphem, NC-1111, R -195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosine , trinactin, verbutin, vertalec, YI-5301.

[0191] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0192] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0193] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprol, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabenda zol .

[0194] The following mixtures of the 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 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5, Tables 5.1 to 5.5, Table T1 (compounds 1.1 to 1.4) or Table T2 (compounds 2.1 or 2.2) (below): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX, 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/Chemical Abstracts name) (1059) + TX, 2-fluoro-N-methyl-N -1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprol [CCN] + TX, acrinathrin ( 9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithine (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenious oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotin (46) + TX, azotoate (889) + TX, benomyl (62) + TX, benoxaphos (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, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate ( 943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (development code) (125) + TX, chinomethionate (126) + TX, chlorobenside ( 959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorofenapyr (130) + TX, chlorophenetol (968) + TX, chlorophensone (970) + TX, chlorfensulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiuron (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, coumaphos ( 174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanoate (1020) + TX, cyflumethophene (No. CAS Reg.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefion ( 1037) + TX, demeton-O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton- O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialyphos (1042) ) + TX, diazinone (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, diclyphos (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, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinoctone (1090) + TX, dinopentone (1092) + TX, dinosulfone (1097) + TX, dinoterbone ( 1098) + TX, dioxathione (1102) + TX, diphenylsulfone (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, methyl ethoate (1134) + TX, ethoxazole (320) + TX, ethrymphos (1142) + TX, fenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX , phenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fensone (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX , fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucycloxuron (366) + TX, flucitrinate (367) + TX, fluenetil (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formetanate (405) + TX, hydrochloride formetanate (405) + TX, formotionin (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, hexythiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, O- ( methoxyaminothiophosphoryl)isopropyl salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmoline I (696) + TX, jasmoline II (696) + TX, iodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathione (492) + TX, malonobene (1254) + TX, mecarbam (502) + TX, mephospholane (1261) + TX, mesulfene (alternative name) [CCN] + TX, Methocarb (1266) + TX, Methamidophos (527) + TX, Metidathione (529) + TX, Methiocarb (530) + TX, Methomyl (531) + TX Methyl Bromide (537) + TX, Metholcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridid (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, 1:1 complex of nitrilacarb with zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI- 0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX, oxydisulfotone (1325) + TX, pp'-DDT (219) + TX, parathion (615) ) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencaptone (1330) + TX, fenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosphamidone (639) + TX, phoxim (642) + TX, pyrimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, pollinactins (alternative name) (653) + TX, proclonol (1350) + TX, profenophos (662) + TX, promacil (1354) + TX, propargite (671) + TX, propetanphos (673) + TX, propoxur (678) + TX, protidathione (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridafenthion (701) ) + TX, pyrimidiphene (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, escradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code ) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX , TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorovinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox ( alternative name) + TX, thiocarboxyme (1431) + TX, thiophanox (800) + TX, thiometone (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorophon (824) + TX, tripenophos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothione (847) + TX, vaniliprol [CCN] and YI-5302 (compound code) + TX, 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, dyclone (1052) + TX, dichlorophene (232) + TX, endothal (295) + TX, phentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) ( 347) + TX, 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, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy -1H-pyridin-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, dodycin (1112) + TX, phenaminosulfe (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, hydroxyquinoline sulfate potassium (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, teclophthalam (766) + TX, and thiomersal (alternative name) [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes 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 thuringiensis subsp. 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 (alternative name) scientific) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (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, strain of bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA and known under the trade name Taegro®) + TX, a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542 ) and methyl bromide (537) + TX, a chemosterilant selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (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, an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (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-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-11-enal (IUPAC name) (436) + TX, (Z)-hexadec-11-en-1-yl (IUPAC name) (437) + TX, (Z)-hexadec-13-en-11-in-1-yl acetate (IUPAC name) (438) + TX, (Z)-icos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC 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) acetate ,9Z)-dodeca-7,9-dien-1-yl (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780 ) + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (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, multistriatin alpha (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemonone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN ] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) alt) (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, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-acetate ila (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) [CCN] + TX, 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, butyl methoquin (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, 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 acetate 2-trichloro-1-(3,4-dichlorophenyl)ethyl (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl phosphate (IUPAC name) (1066) + TX, 2-(1) dimethylcarbamate ,3-dithiolan-2-yl)phenyl (IUPAC/Chemical Abstracts name) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX, 2-methylcarbamate (4,5-dimethyl-1,3-dioxolan-2-yl)phenyl (IUPAC/Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) ( 986) + TX, 2-chlorovinyldiethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindane-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-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3 methylcarbamate, 5-xylyl (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2 ) + TX, acetamiprid (4) + TX, acethion (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, amidithine (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasin (877) + TX, atidathion (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, azotoate (889) ) + TX, Bacillus thuringiensis delta endotoxin (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, bioallethrin (78) + TX, S-cyclopentenyl isomer of bioallethrin (alternative name) (79) + TX, bioethanemethrin [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, butathiophos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxyme ( 104) + TX, butylpyridaben (alternative name) + TX, cadusaphos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX , camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (name IUPAC) (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, chloridexyphos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazuron (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, cismethrin (80) + TX, clocithrin (alternative name) + TX, cloethocarb (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, crotamiton (alternative name) [CCN ] + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanophenol (1019) + TX, cyanophos (184) + TX, cyanthrin (1020) + TX, cyclothrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin ( 206) + TX, cyromazine (209) + TX, cythioate (alternative name) [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, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) ) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialyphos (1042) + TX, diamidaphos (1044) + TX, diazinone (227) ) + TX, dicapton (1050) + TX, diclofenthion (1051) + TX, dichlorvos (236) + TX, diklyphos (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, diflubenzuron (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, dimethylane (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diophenolan (1099) + TX, dioxabenzophos (1100) + TX, dioxacarb (1101) + TX, dioxathione (1102) + TX, disulfotone (278) + TX, dithychrophos (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, endothion (1121) + TX, endothion (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonan (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethione (309) + TX, ethiprol (310) + TX, ethoate-methyl (1134) + TX, ethoprofos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX , ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, ethryphos (1142) + TX, EXD (1143) + TX, fanfur (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, fenpyritrine (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 (No. CAS Reg.: 272451-65-7) + TX, flucofuron (1168) + TX, flucycloxuron (366) + TX, flucitrinate (367) + TX, fluenetil (1169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, phonophos (1191) + TX, formetanate (405) ) + TX, formetanate hydrochloride (405) + TX, formotionin (1192) + TX, formparanate (1193) + TX, fosmethylane (1194) + TX, fospirate (1195) + TX, phostiazate (408) + TX, fosthiethan ( 1196) + TX, furathiocarb (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, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnone (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (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, jasmoline I (696) + TX, jasmoline II (696) + TX, iodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX , juvenile hormone III (alternative name) [CCN] + TX, chelevan (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin ( CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirymphos (1251) + TX, lufenuron (490) + TX, litidathione (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) ( 1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathione (492) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarfon (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, methacryphos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268) + TX, metidathione (529) + TX, Methiocarb (530) + TX, Methocrotophos (1273) + TX, Methomyl (531) + TX Methoprene (532) + TX, Methoquin-butyl (1276) + TX, Methothrin (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, mevinphos (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, naled (567) + TX, naphthalene (IUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (development code) compound) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridid (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX, complex of 1:1 nitrilacarb with zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron ( 585) + TX, noviflumuron (586) + TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, O,O-diethyl-O-4-methyl-phosphorothioate 2-oxo-2H-chromen-7-yl (IUPAC name) (1074) + TX, O,O-diethyl-O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC 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 , oxydemetone-methyl (609) + TX, oxydeprofos (1324) + 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, fencaptone (1330) + TX, phenothrin (630) + TX, fenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosniclore (1339) + TX, phosphamidone (639) + TX, phosphine (IUPAC name) (640) + TX, phoxim (642) + TX, pyrimiphos-methyl (1340) + TX, pyrimethaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocone I (name alt) [CCN] + TX, precocolum II (alternative name) [CCN] + TX, precococen III (alternative name) [CCN] + TX, primidone (1349) + TX, profenophos (662) + TX, profluthrin [CCN] + TX, promacil (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetanphos (673) + TX, propoxur (678) + TX, protidathion (1360) + TX, prothiophos (686) + TX, protoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclophos (689) + TX, pyrazofos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (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, quintiphos (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, riânia (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradan ( 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, Sophamide (1402) + TX, Spinosad (737) + TX, Spiromesifen (739) + TX, Spirotetramate (CCN) + TX, Sulcofurone (746) + TX, Sulcofuron- sodium (746) + TX, sulfluramid (750) + TX, sulphatep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupyrinphos (764) + TX, teflubenzuron (768) + TX , tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX , tetrachlorovinphos (777) + TX, tetramethrin (787) + TX, thetacypermethrin (204) + TX, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrophos (1428) + TX, thiocarboxyme (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogenooxalate (798) + TX, thiodicarb (799) + TX, thiophanox (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, trichlormetaphos (824) + TX, trichlormetaphos-3 (name alternative) [CCN] + TX, trichlorinate (1452) + TX, triprenophos (1455) + TX, triflumuron (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprol [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code ) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [ 736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyraphene [560121-52-0] + TX, cyflumethophene [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, spinetoram [18716640-1 + 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, triflumezopyrim (disclosed in WO 2012/092115) + TX, a molluscicide selected from the group of substances consisting of bis(tributyltin oxide ) (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (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, triphenmorph (1454) + TX, trimetacarb (840) ) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprol [394730-71-3] + TX, 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, 3,4-dichlorotetrahydrothiophene 1,1-dioxide ( IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan acid -3-ylacetic (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, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusaphos (109) + TX , carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidephos (1044) + TX, diclofenthion (1051) + TX, dichlyphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX , ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, fostiazate (408) + TX, fostiethane (1196) + TX, furfural (alternative name) ) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazofos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metam potassium (alternative name) (519) + TX, metame-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, phosphamidone (639) + TX, phosphocarb [ CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC name) /Chemical Abstracts) (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 [318290-98-1] + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin ( 580) + TX, 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, 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, arsenious 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, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, diphethalone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadin (1183) + TX, flupropadin 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, bromide methyl (537) + TX, norbormide (1318) + TX, fosacetime (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, scilliroside (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, a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl 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, piprothal (1343) + TX, isomer of propyl (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, 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, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanine (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a selected wound protectant from the group of substances consisting of mercuric oxide (512) + TX, octylinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole [865318-97-4] + TX, amisulbrom [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzovindiflupyr [1072957-71-1] + TX, bitertanol [7058536-3] + TX, bixaphene [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, isothianyl [224049-04-1] + TX, mandestrobin [173662-97-0 ] (can be prepared according to the procedures described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-304] + TX, penflufen [494793-67-8] + TX, penconazole [6624688-6] + TX, prothioconazole [178928-70-6 ] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [ 107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefone [43121-43-3] + TX, triadimenol [55219-653] + TX, triflumizol [99387-89-0] + TX , triticonazole [13198372-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [6016888-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [4148343-6] + TX, dimetirimol [5221-53-4] + TX, ethirimol [2394760-6] + TX, dodemorph [1593-77-7] + TX, fenpropidin [6730600-7] + TX, fenpropimorph [67564-91-4] + TX , spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + 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, fluundapyr [1383809-87-7] + TX, benalaxyl [71626-11-4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732- 09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX , thiabendazole [148-79-8] + TX, clozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61] -8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-448] + TX, boscalid [188425-85-6] + TX, carboxin [5234-684] + TX, fenfuram [24691- 80-3] + TX, flutolanil [66332-965] + TX, flutianil [958647-10-4] + TX, mepronil [55814-410] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675 -82-3] + TX, tifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961-52-4] + TX, estroburin {Proc. BCPC, Congr. Int., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orysastrobin [24859316-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin [86258811-2] + TX, ferbame [14484-64-1] + TX, mancozeb [8018-017] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071-83-9] + TX, thyram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, capitafol [2425-06-1] + TX, capitan [133] -06-2] + TX, dichlofluanid [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanid [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 [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131-72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphene [ 36519-00-3] + TX, pyrazofos [13457-18-6] + TX, tolclophos-methyl [57018-049] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101- 05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionate [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [5796695-7] + TX, dyclone [117-80-6] + TX, diclocymet [139920-324 ] + TX, diclomezine [62865-36-5] + TX, dichloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [11048870-5] + 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, phenamidone [161326-34-7] + TX, phenoxanyl [115852-48-7] + TX, fentin [668-34-8] + TX, ferinzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamide [126833-178] + TX, fosetyl aluminum [39148- 24-8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Ciazofamid) [120116-88-3] + TX, kasugamycin [6980-18 -3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazid [189278-12- 4] + TX, pidiflumethophene [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyroquilone [57369-32-1] + TX, pyriophenone [688046-61-9] + TX, piribencarb [799247-52-2] + TX, pyrisoxazole [847749-37-5] + TX, quinoxyfen [12449518-7] + TX, quintazene [82-68-8] + TX, sulfur [7704-34-9] + TX, Timorex GoldTM (plant extract containing tea tree oil from the Stockton Group) + TX, tebufloquine [376645-78-2] + TX, tiadinyl [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tolprocarb [911499-62-2] + TX, triclopiricarb [902760-40-1] + TX, tricyclazole [41814-78-2] + TX, triforine [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- 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methane-naphthalen-5-yl)-amide (disclosed in WO 2007/048556) + TX, (3',4',5'-trifluoro- 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX, [(3S,4R,4aR,6S,6aS,12R, 12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,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]methylcyclopropanecarboxylate [915972-17-7] + TX and 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, 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-pyrazole-4-carboxamide (can be prepared according to procedures described in WO 2010/130767) + TX, 2,6-Dimethyl -1H,5H-[1,4]dithi-yno[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (can be prepared according to procedures described in WO 2011/138281) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dit-yno[1,2-c]isothiazole-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-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,1-dioxide 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-6-[(8-fluoro-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-difluoro-2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol (can be prepared according to procedures described in WO 2011 /081174) + TX, oxathiapiproline + TX [1003318-67-9], N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate tert-butyl + 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, 2,2,2-trifluoroethyl N-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy) )- α,α,α-trifluoro-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-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-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, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4 methanesulfonate, 5-dihydroisoxazol-5-yl]-3-chloro-phenyl] (can be prepared according to the procedures described in WO 2012/025557) + TX, N-[6-[[(Z)-[(1 But-3-ynyl-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (can 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 (can 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 -chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (can be prepared according to 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 described in WO 2012/020774) + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1, 3-trimethylindan-4-yl]pyrazole-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-pyrazole-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 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 according to procedures described in WO 2014/051165) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-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 WO 2010/130767) + TX, 3-(difluoromethyl)-N-[(R)-2 ,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-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-dimethyl-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, (fenpicoxamide [517 875-34-2]) + 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)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridin- 3-carboxamide + TX, and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide + TX, wherein each of these compounds of carboxamide can be prepared according to the procedures described in WO 2014/095675 and/or WO 2016/139189.

[0195] References in square brackets after active ingredients, eg [3878-19-1] refer to the Chemical Abstracts Registration Number. The mixing partners described above are known. When active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C.D.S. TomLin; The British Crop Protection Council] these are described there under the entry number given in parentheses above for the particular compound; for example, the compound "abamectin" is described under entry number (1). When "[CCN]" is here added above to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible over the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprol" is described at http://www.alanwood.net/pesticides/acetoprole.html.

[0196] Most of the active ingredients described above are referred to above in this document by a so-called “common name”, the relevant “ISO common name” or other “common name” being used in individual cases. If the designation is not a "common name", the nature of the designation used in the alternative is given in parentheses for the particular compound; in this case the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” is used or, if neither of these designations nor a "common name", an "alternate name" is used. "At the. CAS Reg.” means the Chemical Abstracts Registration Number.

[0197] The mixture of active ingredients of the compounds of Formula (I) selected from a compound 1.1 to 1.4 described in Table T1 (below), a compound 2.1 or 2.2 described in Table T2 (below), or a compound of Formula (I) described in Tables 1.1 to 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5 or Tables 5.1 to 5.5 (below), and an active ingredient as described above, are preferably in a mixing ratio of 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio from 20:1 to 1:20, even more especially from 10:1 to 1:10, most especially from 5:1 to 1:5, with special preference given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 likewise being 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 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are by weight.

[0198] The mixtures as described above can be used in a method for controlling pests comprising applying a composition comprising a mixture as described above to pests or their environment, with the exception of a method for treating the human body or animal by surgery or therapy and diagnostic methods practiced on the human or animal body.

[0199] Mixtures comprising a compound 1.1 to 1.4 described in Table T1 (below), a compound 2.1 or 2.2 described in Table T2 (below), or a compound of Formula (I) described in Tables 1.1 to 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5 or Tables 5.1 to 5.5 (below) and one or more active ingredients as described above may be applied, e.g. in a single “ready-to-mix” form, in a mixture for combined spraying composed of separate formulations of the individual active ingredient components, such as a “mixing tank”, and in a combined use of the individual active ingredients when applied in a sequential manner, i.e. one after the other within a reasonably short period, such as a few hours or days. The order of application of the compound of Formula (I) selected from a compound 1.1 to 1.4 described in Table T1 (below), a compound 2.1 or 2.2 described in Table T2 (below) or a compound of Formula (I) described in Tables 1.1 to 1.5, Tables 2.1 to 2.5, Tables 3.1 to 3.5, Tables 4.1 to 4.5 or Tables 5.1 to 5.5 (below), and the active ingredient(s) as described above, is not essential to the work of present invention.

[0200] 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), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or adhesives, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

[0201] 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 compression of a solid active ingredient and in the presence of at least one auxiliary, for example by intimate mixing and/or grinding of the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds of Formula (I) for the preparation of these compositions are also an object of the invention.

[0202] Another aspect of the invention relates to the use of a compound of formula (I) or a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one individual compound preferred 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, their propagation material, for example seeds, harvested crops, for example harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.

[0203] 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, harvested crops, for harvested food crops, or from non-living materials by insects or by 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 propagation material or any part of non-living material.

[0204] Means of control or prevention that reduce infestation by microorganisms or phytopathogenic or deteriorating organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.

[0205] A preferred method for controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which comprises applying a compound of formula (I), or an agrochemical composition containing at least one of said compounds, is foliar application. Application frequency and application rate will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of Formula (I) can also enter the plant via the roots via the soil (systemic action) by drenching the plant locus with a liquid Formulation, or by applying the compounds in solid form to the soil, e.g. e.g. in granular form (soil application). In irrigated rice crops, such pellets 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.

[0206] A formulation, p. ex. 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 known manner, typically by intimately mixing and/or grinding the compound with diluents, e.g. solvents, solid carriers and, optionally, surfactant compounds (surfactants).

[0207] Advantageous application rates normally range from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, more preferably from 20 g to 600 g a.i./ha. When used as a seed drenching agent, convenient dosages range from 10 mg to 1 g of active substance per kg of seed.

[0208] When the combinations of the present invention are used to treat seeds, rates of 0.001 to 50g of a compound of Formula (I) per kg of seed, preferably 0.01 to 10g per kg of seed are generally sufficient.

[0209] 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.

[0210] The compositions of the invention may be employed in any conventional form, for example in the form of a double pack, a dry seed treatment (DS) powder, a seed treatment (ES) emulsion, a suitable concentrate Flow Seed Treatment (FS), Seed Treatment Solution (LS), Seed Treatment Water Dispersible Powder (WS), Seed Treatment Capsule Suspension (CF), Seed Treatment Gel (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 (SU) suspension, an ultra-low volume (UL) liquid, a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically possible in combination with agriculturally acceptable adjuvants.

[0211] Such compositions can be produced conventionally, for example, by mixing the active ingredients with appropriate formulation fillers (diluents, solvents, fillers and, optionally, other formulation ingredients such as surfactants, biocides, antifreezes, adherents , thickeners and compounds that provide adjuvant effects). Conventional slow-release formulations may also be employed when long-lasting efficacy is desired. Particularly, 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.

[0212] 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 suitable seed coating formulation form, e.g. e.g., as an aqueous suspension or in a dry powder form having good adherence to seeds. Such seed treatment formulations are known in the art. Seed treatment formulations may contain the individual active ingredients or the combination of active ingredients in encapsulated form, e.g. e.g., as slow-release capsules or microcapsules.

[0213] In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of agriculturally acceptable surfactant, and from 10 to 99.99% of 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 microbiocides 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. The application forms of the formulation may for example 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 normally employ dilute formulations.

[0214] While it is preferred to formulate commercial products as concentrates, the end user will typically use dilute formulations.

[0215] Table 1.1: This table discloses 38 specific compounds of formula (T-1): where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(difluoromethyl) and R8 is as defined below in Table 1.

[0216] Each of Tables 1.2 to 1.5 (which follow Table 1.1) makes available 38 individual compounds of the formula (T-1) in which A1, A2, A3, A4, R5, R6 and R7 are as specifically defined in the Tables 1.2 to 1.5, which refer to Table 1, where R8 is specifically defined. Table 1

[0217] Table 1.2: This table discloses 38 specific compounds of the formula (T-1), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2-difluoroethyl) and R8 is as defined above in Table 1.

[0218] Table 1.3: This table discloses 38 specific compounds of the formula (T-1), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(fluoromethyl) and R8 is as defined above in Table 1.

[0219] Table 1.4: This table discloses 38 specific compounds of the formula (T-1), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2-fluoroethyl) and R8 is as defined above in Table 1.

[0220] Table 1.5: This table discloses 38 specific compounds of the formula (T-1), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2,2-trifluoroethyl) and R8 is as defined above in Table 1.

[0221] Table 2.1: This table discloses 10 specific compounds of formula (T-2): where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2,R3, R4, R5 and R6 are hydrogen, R7 is O-(difluoromethyl) and R10 is as defined below in Table 2.

[0222] Each of Tables 2.2 to 2.5 (which follow Table 2.1) makes available 10 individual compounds of the formula (T-2) in which A1, A2, A3, A4, R5, R6 and R7 are as specifically defined in the Tables 2.2 to 2.5, which refer to Table 2, where R10 is specifically defined. Table 2

[0223] Table 2.2: This table discloses 10 specific compounds of the formula (T-2), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2-difluoroethyl) and R10 is as defined above in Table 2.

[0224] Table 2.3: This table discloses 10 specific compounds of the formula (T-2), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2-fluoroethyl) and R10 is as defined above in Table 2.

[0225] Table 2.4: This table discloses 10 specific compounds of the formula (T-2), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(fluoromethyl) and R10 is as defined above in Table 2.

[0226] Table 2.5: This table discloses 10 specific compounds of the formula (T-2), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2,2-trifluoroethyl) and R10 is as defined above in Table 2.

[0227] Table 3.1: This table discloses 12 specific compounds of formula (T-3): NR12(R13) is as defined below in Table 3.

[0228] Each of Tables 3.2 to 3.5 (which follow Table 3.1) makes available 12 individual compounds of the formula (T-3) in which A1, A2, A3, A4, R5, R6 and R7 are as specifically defined in the Tables 3.2 to 3.5, which refer to Table 3, where NR12(R13) is specifically defined. Table 3

[0229] Table 3.2: This table discloses 12 specific compounds of the formula (T-3), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2-difluoroethyl) and NR12(R13) is as defined above in Table 3.

[0230] Table 3.3: This table discloses 12 specific compounds of the formula (T-3), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2-fluoroethyl) and NR12(R13) is as defined above in Table 3.

[0231] Table 3.4: This table discloses 12 specific compounds of the formula (T-3), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(fluoromethyl) and NR12(R13) is as defined above in Table 3.

[0232] Table 3.5: This table discloses 12 specific compounds of the formula (T-3), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2,2-trifluoroethyl) and NR12(R13) is as defined above in Table 3.

[0233] Table 4.1: This table discloses 6 specific compounds of formula (T-4): where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4, and R1, R2, R3, R4, R5, and R6 are hydrogen, R7 is O-(difluoromethyl), R16 is oxygen and R17 is as defined below in Table 4.

[0234] Each of Tables 4.2 to 4.5 (which follow Table 4.1) makes available 6 individual compounds of the formula (T-4) in which A1, A2, A3, A4, R5, R6, R7, and R16 are as specifically defined in Tables 4.2 to 4.5, which refer to Table 4, where R17 is specifically defined. Table 4

[0235] Table 4.2: This table discloses 6 specific compounds of the formula (T-4), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2-difluoroethyl), R16 is oxygen and R17 is as defined above in Table 4.

[0236] Table 4.3: This table discloses 6 specific compounds of the formula (T-4), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2-fluoroethyl), R16 is oxygen and R17 is as defined above in Table 4.

[0237] Table 4.4: This table discloses 6 specific compounds of the formula (T-4), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(fluoromethyl), R16 is oxygen and R17 is as defined above in Table 4.

[0238] Table 4.5: This table discloses 6 specific compounds of the formula (T-4), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2,2-trifluoroethyl), R16 is oxygen and R17 is as defined above in Table 4.

[0239] Table 5.1: This table discloses 18 specific compounds of formula (T-5): where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4, and R1, R2, R3, R4, R5, and R6 are hydrogen, R7 is O-(difluoromethyl), and R19 is as defined below in Table 5.

[0240] Each of Tables 5.2 to 5.5 (which follow Table 5.1) makes available 18 individual compounds of the formula (T-5) in which A1, A2, A3, A4, R5, R6 and R7 are as specifically defined in the Tables 5.2 to 5.5, which refer to Table 5, where R19 is specifically defined. Table 5

[0241] Table 5.2: This table discloses 18 specific compounds of the formula (T-5), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2-difluoroethyl and R19 is as defined above in Table 5.

[0242] Table 5.3: This table discloses 18 specific compounds of the formula (T-5), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2-fluoroethyl) and R19 is as defined above in Table 5.

[0243] Table 5.4: This table discloses 18 specific compounds of the formula (T-5), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(fluoromethyl) and R19 is as defined above in Table 5.

[0244] Table 5.5: This table discloses 18 specific compounds of the formula (T-5), where A1 is C-R1, A2 is C-R2, A3 is C-R3, A4 is C-R4 and R1, R2, R3, R4, R5 and R6 are hydrogen, R7 is O-(2,2,2-trifluoroethyl) and R19 is as defined above in Table 5.

EXAMPLES

[0245] The Examples which follow 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, e.g. 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0246] The compounds of Formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (e.g., increased biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physicochemical properties or increased biodegradability).

[0247] 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: Waters SQ 2 Detector Ionization method: Electrospray Polarity: positive and negative ions Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Flow Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650 Mass Range: 100 to 900 DAD Wavelength Range (nm): 210 to 500

[0248] Waters ACQUITY UPLC method with the following HPLC gradient conditions: (Solvent A: Water/Methanol 20:1 + 0.05% formic acid and Solvent B: Acetonitrile + 0.05% formic acid)

[0249] Column type: ACQUITY UPLC HSS T3 from Waters; Column Length: 30mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 LC/MS apparatus and method B description is: Waters SQ 2 Detector Ionization method: Electrospray Polarity: positive ions Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) ) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700 Mass range: 140 to 800 DAD wavelength range (nm): 210 to 400

[0250] Waters ACQUITY UPLC method with the following HPLC gradient conditions: (Solvent A: Water/Methanol 9:1 + 0.1% formic acid and Solvent B: Acetonitrile + 0.1% formic acid)

[0251] Column type: Waters ACQUITY UPLC HSS T3; Column Length: 30mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60°C.

[0252] When necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate via standard physical separation techniques such as chiral reversed phase chromatography, or via stereoselectives, e.g. ex. using chirals. Formulation Examples

[0253] The active ingredient is carefully mixed with the adjuvants and the mixture is carefully ground in a suitable mill, yielding wettable powders that can be diluted with water to yield suspensions of the desired concentration. Powders for seed treatment aa) b) c) dry

[0254] The active ingredient is carefully mixed with the adjuvants and the mixture is carefully ground in a suitable mill, resulting in powders that can be used directly for seed treatment. Emulsifiable concentrate

[0255] Emulsions of any required dilution can be obtained, which can be used in plant protection, from this concentrate by dilution with water.

[0256] 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 treatments.

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

[0258] The finely ground active ingredient is evenly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this way.

[0259] The finely ground active ingredient is intimately mixed with the adjuvants, giving 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 dipping.

[0260] The finely ground active ingredient is intimately mixed with the adjuvants, giving 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 dipping.

Suspension of slow-release capsules

[0261] 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 of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of 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 completed.

[0262] The capsule suspension obtained is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. Capsule Suspension Formulation contains 28% active ingredients. The average capsule diameter is 8-15 microns.

[0263] The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose. List of Abbreviations: AIBN = azobisisobutyronitrile BOP-Cl = phosphoric acid bis(2-oxo-oxazolidide) chloride CDI = carbonyl diimidazole DCE = 1,2-dichloroethane DCM = dichloromethane DIBAL-H = diisobutylaluminum hydride DIPEA = N,N-diisopropylethylamine DMA = dimethylacetamide DMF = dimethylformamide EdCl = 3-(ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine EtOAc = ethyl acetate EtOH = ethyl alcohol HCl = hydrochloric acid HOAt = 1-hydroxy -7-azabenzotriazole HATU = 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidehexafluorophosphate mp = melting point MeOH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide = room temperature TFAA = trifluoroacetic acid anhydride THF = tetrahydrofuran

Preparative Examples

[0264] Using the synthetic techniques described both above and below, compounds of formula (I) can be prepared accordingly.

[0265] Example 1: This example illustrates the preparation of 1-(2,2-difluoroethoxy)-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl ]phenyl]methyl]urea (Compound 2.1 of Table T2) Step 1: Preparation of N'-hydroxy-4-methyl-benzamidine

[0266] To a suspension of 4-methylbenzonitrile (35 g, 0.29 mol) in ethanol (220 mL) and water (440 mL) were added at room temperature hydroxylamine hydrochloride (41.1 g, 0.58 mol) , 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 cooled to room temperature and diluted with 2N HCl to pH 8. Volatiles 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

[0267] 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 and then diluted with water. The organic layer was separated, washed successively with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution, water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The impure residue was purified by flash chromatography on silica gel (eluent gradient heptane/EtOAc 99:1 to 90:10) to give 54.1 g of the title compound as a clear oil, which solidified upon storage. LC/MS (Method A) retention time = 1.15 minutes, mass not detected.

[0268] 1H NMR (400 MHz, CDCl3) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

[0269] 19F NMR (400 MHz, CDCl3) δ ppm: -65.41 (s). Step 3a: Preparation of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

[0270] 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 sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (eluent gradient cyclohexane/EtOAc 100:0 to 95:5) to afford 44.7 g of the title compound as a white oil. mp: 58-63 °C.

[0271] 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

[0272] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s).

[0273] 3-[4-(Dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole was isolated as a by-product as a white solid with mp: 61-66 °C.

[0274] 1H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

[0275] 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

[0276] To a 1:9 ratio mixture 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 diethylphosphite (4 .7 mL, 35.7 mmol) at 5°C. The mixture was stirred at 5-10°C for two hours, 1M HCl was added and the volatiles were removed under reduced pressure. The resulting white paste was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting impure product was purified by silica gel flash chromatography (eluent gradient cyclohexane:EtOAc 99:1 to 9:1) to give 7.10 g of the title compound as a white solid. mp: 58-63 °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). Step 4: Preparation of N-(2,2-difluoroethoxy)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

[0279] To a solution of O-(2,2-difluoroethyl)hydroxylamine hydrochloride (0.52 g, 3.9 mmol) in acetonitrile (10 mL) was introduced potassium carbonate (1.36 g, 9.77 mmol) and the contents stirred for 30 minutes. Then 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1 g, 3.26 mmol) was introduced dropwise as an acetonitrile solution (6 mL). The mixture was stirred at room temperature for 72 hours and the heterogeneous solution was filtered to remove solids. The solvent was removed under reduced pressure and the resulting crude material was purified by silica gel flash chromatography (eluent gradient from cyclohexane/EtOAc 1:0 to 1:1) to give the title compound (0.20 g, 19% yield) as a clear oil. LC/MS (Method A) retention time = 1.08 minutes, no mass detected.

[0280] 1H NMR (400 MHz, CDCl3)) δ ppm: 8.19 (d, 2H), 7.55 (d, 2H), 6.14 (m, 1H), 5.90 (m, 1H) , 4.17 (m, 2H), 3.81 (m, 2H).

[0281] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s), - 126.39 (s).Step 5: Preparation of 1-(2,2-difluoroethoxy)-3-methyl-1 -[[4—[5—(trifluoromethyl)-1,2,4—oxadiazol-3-yl]-2-phenyl]methyl]urea

[0282] To a solution of 1-[2,5-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methylmethanamine (80 mg, 0 .25 mmol) in dichloromethane (1.2 mL) cooled to 0 °C, N-methylcarbamoyl chloride (0.23 g, 0.28 mmol) and triethylamine (0.035 mL, 0.25 mmol) were added. hours, the reaction mixture was concentrated under reduced pressure and the resulting crude residue was purified by flash silica gel chromatography (eluent gradient cyclohexane/EtOAc 1:0 to 1:2) to provide the desired product (63 mg, 69% yield) as a white solid; mp 82 - 85 °C; LC/MS (Method A) retention time = 1.02 minutes, 381.2 (M+H).

[0283] 1H NMR (400 MHz, CDCl3) δ ppm: 8.13 (d, 2H), 7.55 (d, 2H), 5.93 (m, 1H), 5.92 (m, 1H), 4.76 (d, 2H), 3.88 (d, 2H), 2.89 (d, 3H).

[0284] 19F NMR (400 MHz, CDCl3) δ ppm: -65.30 (s), -126.62 (s).

[0285] Example 2: This example illustrates the preparation of N-(2,2-difluoroethoxy)-1-fluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl ]phenyl]methyl]cyclopropanecarboxamide (Compound 1.2 of Table T1)

[0286] A stirring solution of 1-fluorocyclopropanecarboxylic acid (0.022 g, 0.22 mmol) and HATU (0.11 g, 0.29 mmol) in DMF (1 mL) under a nitrogen atmosphere at room temperature was N-ethyl-N-isopropyl-propan-2-amine (0.7 mL, 0.39 mmol) is introduced. After 5 minutes, 1-[2,5-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methyl-methanamine (0.064 g, 0.02 mmol ) has been added. After 1 hour, ethyl acetate and water were introduced and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. A crude white gum was purified by flash chromatography on silica gel (99:1 to 1:1 cyclohexane/EtOAc eluent gradient) to give the title compound (0.03 g, 37%) as an oil. transparent. LC/MS (Method A) retention time = 1.14 minutes, 410 (M+H).

[0287] 1H NMR (400 MHz, CDCl3) δ ppm: 8.14 (d, 2H), 7.54 (d, 2H), 5.92 (m, 1H), 4.97 (m, 2H), 4.13 (m, 2H), 1.39 (m, 2H), 1.32 (m, 2H). Example 3: This example illustrates the preparation N-(fluoromethoxy)-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound 1.4 of Table T1) Step 1: Preparation of [tert-butyl-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino] carbonate

[0288] A white suspension of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.15 g, 0.46 mmol), (tert-butoxycarbonylamino) carbonate of tert-butyl (0.16 g, 0.70 mmol) and potassium carbonate (0.13 g, 0.93 mmol) in acetonitrile (4.7 mL) was placed in a microwave flask. The mixture was stirred in a microwave oven at 120°C for 30 minutes. The heterogeneous yellow suspension was filtered to remove solids. The solvent was removed under reduced pressure and the resulting crude material was purified by silica gel flash chromatography (12 g prepacked column) (1:0 to 1:1 cyclohexane/EtOAc eluent gradient) to give the title compound (0.086 g, 52% yield) as a clear oil. LC/MS (Method A) retention time, mass not detected.

[0289] 1H NMR (400 MHz, CDCl3) δ ppm: 8.08 (d, 2H), 7.83 (s, 1H), 7.49 (d, 2H), 4.72 (s, 2H), 1.45 (s, 9H). Step 1b: Preparation of [tert-butoxycarbonyl-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino] tert-butyl carbonate

[0290] A colorless solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.40 g, 1.3 mmol)) in acetone (6.5 mL ) was treated with tert-butyl (tert-butoxycarbonylamino) carbonate (0.31 g, 1.3 mmol) and potassium carbonate (0.18 g, 1.3 mmol). The mixture was stirred at 20°C overnight. The heterogeneous yellow suspension was filtered, washed with acetone to remove solids. The solvent was removed under reduced pressure and the resulting crude material was purified by silica gel flash chromatography (12 g prepacked column) (eluent gradient from cyclohexane/EtOAc 1:0 to 1:1) to give the title compound (0.39 g, 66% yield) as a clear oil. LC/MS (Method A) retention time = 1.31 minutes, no mass detected.

[0291] 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.51 (d, 2H), 4.83 (s, 2H), 1.49 (s, 9H), 1.48 (s, 9H). Step 2: Preparation of hydroxy-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ammonium chloride

[0292] To a clear solution of tert-butyl [tert-butoxycarbonyl-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino] carbonate (5 .58 g, 12.1 mmol) in dioxane (2.0 mL) was added 2M HCl in dioxane (15 mL, 30 mmol). Precipitation of bubbling solid and gas began immediately. The mixture was stirred at 50°C overnight. The white solid was filtered, washed with cyclohexane and dried under vacuum to give (2.82 g, 79% yield) the title compound, mp. > 210 °C. LC/MS (Method A) retention time = 0.70 minutes, 260.0 (M+H).

[0293] 1H NMR (400 MHz, DMSO) δ ppm: 11.83 (s, 1H), 10.98 (s, 1H), 8.12 (d, 2H), 7.76 (d, 2H), 4.43 (s, 2H). Step 3: Preparation of N-hydroxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide

[0294] To a solution of hydroxy-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ammonium chloride (0.90 g, 3.04 mmol) in dichloromethane (10 mL) cooled to 0 °C triethylamine (0.86 mL, 6.08 mmol) and cyclopropanecarbonyl chloride (0.28 mL, 3.20 mmol) in dichloromethane (5 mL) were added over 20 minutes. After 3 hours, dichloromethane and water were introduced and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude gum was purified by flash chromatography on silica gel (eluent gradient from cyclohexane/EtOAc 3:2 to 1:1) to give the title compound (0.73 g, 73.2%) as a transparent oil. LC/MS (Method A) retention time = 0.95 minutes, 328.2 (M+H).

[0295] 1H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.50 (d, 2H), 6.02 (s, 1H), 5.02 (s, 2H), 1.81 (m, 1H), 1.12 (m, 2H), 0.87 (m, 2H).Step 4: Preparation of N-(fluoromethoxy)-N-[[4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide

[0296] To a solution of N-hydroxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (150 mg, 0.46 mmol) in DMSO (2 mL) cooled to 0°C was added potassium carbonate (0.13 g, 0.92 mmol). The reaction mixture was heated to 50 °C. For 3 hours, a slow stream of bromofluoromethane was introduced. After 3 hours, ethyl acetate and water were introduced and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude gum was purified by flash chromatography on silica gel (5:1 to 3:1 cyclohexane/EtOAc eluent gradient) to give the title compound (0.047 g, 28.9%) as a clear oil . LC/MS (Method A) retention time = 1.09 minutes, 360.2 (M+H).

[0297] 1H NMR (400 MHz, CDCl3) δ ppm: 8.13 (d, 2H), 7.50 (d, 2H), 5.60 (s, 1H), 5.45 (s, 1H), 5.01 (s, 2H), 2.20 (m, 1H), 1.10 (m, 2H), 0.89 (m, 2H).

[0298] 19F NMR (400 MHz, CDCl3) δ ppm: -66 (s), -151.31 (s). Example 4: This example illustrates the preparation of N-(fluoroethoxy)-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound 1.3 of Table T1 ) Step 1: Preparation of N-(fluoroethoxy)cyclopropanecarboxamide

[0299] To a suspension of O-(2-fluoroethyl)hydroxylamine (0.100 g, 1.26 mmol) in dichloromethane (19 mL) cooled to 0 °C was added triethylamine (0.26 g, 2.53 mmol), followed by the addition of cyclopropanecarbonyl chloride (0.15 g, 1.39 mmol). After 16 hours, the reaction mixture was concentrated under reduced pressure and the resulting crude residue was directly used in the next step. Step 2: Preparation of N-(fluoroethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide

[0300] To a solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.368 g, 1.2 mmol), N-(fluoroethoxy)cyclopropanecarboxamide (0.177 g , 1.2 mmol) in acetonitrile (12 mL) was added potassium acetate (0.335 g, 2.4 mmol) and the contents were stirred at room temperature overnight. The suspension was filtered to remove solids. The solvent was removed under reduced pressure and the resulting crude material was purified by silica gel flash chromatography (eluent gradient from cyclohexane/EtOAc 1:0 to 1:1), dichloromethane/methanol (1:1) to give the title compound (0.025 g, 6% yield) as a clear oil. LC/MS (Method A) retention time = 1.07 minutes, 374.2 (M+H).

[0301] 1H NMR (400 MHz, CDCl3)) δ ppm: 8.13 (d, 2H), 7.51 (d, 2H), 4.92 (s, 2H), 4.60 (m, 2H) , 4.15 (m, 2H), , 2.20 (m, 1H), 1.10 (m, 2H), 0.88 (m, 2H).

[0302] 19F NMR (400 MHz, CDCl3) δ ppm: -65 (s), -223.16 (s).

[0303] The following procedure was used in a combinatorial manner using appropriate building blocks (compounds (II) and (III)) to provide the compounds of formula (Ia) where Za is -R8, -OR10, -NR12R13 or - C(=R16)R17. Compounds prepared by the following combinatorial protocol were analyzed using LC/MS Method B.

[0304] By way of example, acid derivatives of formula (II) (0.0375 mmol in 375 μL of DMA) were transferred to a 96-slot deep well plate (DWP96) containing the derivatives [[5-(trifluoromethyl) - 1,2,4-oxadiazol-3-yl]aryl]haloalkoxyamine of formula (III) (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 compounds of formula (I) in 10-85% yields.

[0305] The following procedure was used in a combinatorial manner using appropriate building blocks (compounds (III) and (IV)) to provide the compounds of formula (Ib) wherein Zb is -OR10 or -NR12R13. Compounds prepared by the following combinatorial protocol were analyzed using LC/MS Method B.

[0306] By way of example, portions of triphosgene (5.94 mg) in DCE (0.3 mL) were transferred at 0 °C to a deep well plate with 96 grooves (DWP96) containing the alcohol derivative [HOR10] or amine derivative [HN(R12)R13] of formula (IV) (0.05 mmol) and triethylamine (0.12 mmol) in 200 µL DMA. The reaction mixtures were stirred at rt for 30 minutes, then the [[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]haloalkoxyamine derivatives of formula (III) (0.05 mmol) were added and triethylamine (0.12 mmol) in 200 µL of DMA. The DWP was sealed and stirred at rt for 18 hours. The DCE was removed under Barkey's station. The impure residues were solubilized in a mixture of MeOH (200 μL) and DMA (600 μL) and directly submitted for purification by preparative LC/MS which provided the compounds of formula (I) in 10-85% yields.

[0307] The following procedure was used in a combinatorial manner using appropriate building blocks (compounds (III) and (VII)) to provide the compounds of formula (Id) wherein Zd is R19. Compounds prepared by the following combinatorial protocol were analyzed using LC/MS Method B.

[0308] By way of example, solutions of sulfonyl chloride derivatives of formula (VII) (0.08 mmol) in ethyl acetate (1 mL) were transferred to a deep well plate with 96 grooves (DWP96) containing the derivatives of [[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine of formula (III) (0.04 mmol) and DIPEA (0.16 mmol) in ethyl acetate (1 mL ). The reaction mixtures were stirred at rt overnight and then the ethyl acetate was removed using the Barkey station. The impure residues were solubilized in a mixture of MeOH (200 μL) and DMA (600 μL) and directly submitted for purification by preparative LC/MS which provided the compounds of formula (I) in 10-85% yields. Table T1: Melting point (mp) and/or retention times (RT) data for compounds according to Formula (I): Table T2: Melting point (pf) and/or retention times (RT) data for compounds according to Formula (I):

BIOLOGICAL EXAMPLES: General examples of tests with leaf discs in well plates:

[0309] Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. Leaf discs or segments are placed in multi-well plates (24-well format) in water agar. Leaf discs are sprayed with a test solution before (preventive) or after (curative) inoculation. Compounds to be tested are prepared as solutions in DMSO (maximum 10 mg/mL), which are diluted to the appropriate concentration with 0.025% Tween20 immediately before spraying. Inoculated discs or leaf 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 after 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:

[0310] Mycelia fragments or suspensions of conidia of a fungus, either freshly prepared from liquid cultures of the fungus or from cryogenic storage, are directly mixed into nutrient broth. DMSO solutions of the test compound (maximum 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). The nutrient broth containing the fungal spores/mycelia fragments is then added to generate a final concentration of the test 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 of antifungal activity relative to the untreated check is calculated.

Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / preventive on leaf discs (Brown rust)

[0311] 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 spore suspension of the fungus 1 day after application. Inoculated leaf segments were incubated at 19°C and relative humidity (rH) of 75% under a light regime of 12 hours light/12 hours dark in a climate chamber, and the activity of a compound was evaluated as a percentage of disease control versus no treatment when an appropriate level of disease damage appears on untreated check leaf segments (7 to 9 days after application).

[0312] The following compounds at 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. Compounds (from Table T1) 1.3 and 1.4. Compounds (from Table T2) 2.1 and 2.2.

Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / dressing on leaf discs (Brown rust)

[0313] 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 spore suspension of the fungus. 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 light regime of 12 hours light / 12 hours dark in a climate chamber, and the activity of a compound was evaluated as a percentage of disease control in compared to no treatment, when an appropriate level of disease damage appears on untreated control leaf segments (6 to 8 days after application).

[0314] The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development. Compounds (from Table T1) 1.3 and 1.4. Compounds (from Table T2) 2.1 and 2.2.

Fungicidal activity against Phakopsora pachyrhizi / soybean / preventive on leaf discs (Asian soybean rust)

[0315] 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 onto the lower leaf surface. After an incubation period of 24-36 hours in a climate chamber, in the dark at 20°C and r.u. 75%, the leaf discs are kept at 20°C with 12 h of light/day and u.r. of 75%. The activity of a compound is evaluated as percent disease control compared to no treatment when an appropriate level of disease damage appears on untreated check leaf discs (12 to 14 days after application).

[0316] The following compounds at 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. Compounds (from Table T1) 1.3 and 1.4. Compounds (from Table T2) 2.1 and 2.2.

Fungicidal activity against Gl omerella lagenari um (Colletotrichum lagenarium) liquid culture / cucumber / preventive (Anthracnose)

[0317] The conidia of the fungus from cryogenic storage are mixed directly into nutrient broth (PDB - potato dextrose broth). After placing a (DMSO) solution of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. Test plates are incubated at 24°C and growth inhibition is determined photometrically 3 to 4 days after application.

[0318] The following compounds at 20 ppm in the applied formulation confer at least 80% disease control in this test compared to untreated control under the same conditions, which shows extensive disease development. Compounds (from Table T1) 1.1 , 1.2, 1.3 and 1.4 Compounds (from Table T2) 2.1 and 2.2.

Claims (12)

1. Compound, characterized by the fact that it has formula (I): R5 and R6 independently represent hydrogen; R7 represents C1-4haloalkoxy; Z is selected from Z1 or Z3; wherein Z1 represents -C(O)R8, wherein R8 represents halo-substituted or unsubstituted aminoC1-6alkyl, halo-substituted or unsubstituted C3-6cycloalkyl, or halo-substituted phenyl; Z3 represents -C(O)NR12R13, wherein R12 represents hydrogen or C1-4alkyl; and R13 represents hydrogen, methyl, ethyl, propyl or isopropyl; or a salt or N-oxide thereof. 2. Compound, according to claim 1, characterized by the fact that R7 is C1-4fluoroalkoxy. 3. Compound according to claim 2, characterized in that R7 is fluoromethoxy, 2-fluoroethoxy or 2,2-difluoroethoxy. 4. Compound according to any one of claims 1 to 3, characterized in that Z is Z1. 5. Compound, according to claim 4, characterized by the fact that R8 is C1-4alkyl. 6. Compound according to claim 4, characterized in that R8 is cyclopropyl, cyclobutyl, cyclopropylmethyl optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R9, in which R9 is halogen, or phenyl substituted by 1 or 2 substituents, which may be the same or different, selected from R9, where R9 is halogen. 7. Compound according to any one of claims 1 to 3, characterized in that Z is Z3. 8. Compound, according to claim 7, characterized by the fact that R13 is hydrogen, methyl or ethyl. 9. Agrochemical composition, characterized in that it comprises an effective amount from a fungicidal point of view of a compound of Formula (I), as defined in any one of claims 1 to 8, and an agrochemically acceptable diluent or carrier. 10. Composition according to claim 9, characterized in that it additionally comprises at least one additional active ingredient. 11. Method for controlling or preventing the infestation of useful plants by phytopathogenic microorganisms, characterized in that an effective amount from the fungicidal point of view of a compound of Formula (I), as defined in any one of claims 1 to 8, or a composition comprising this compound as an active ingredient is applied to the plants, their parts or their locus. 12. Use of a compound of Formula (I), as defined in any one of claims 1 to 8, characterized in that it is a fungicide.