BR112019020756B1 - COMPOUNDS DERIVED FROM OXADIAZOLE MICROBICIDES, AGROCHEMICAL COMPOSITION COMPRISING THE SAME, METHOD FOR CONTROLLING OR PREVENTING INFESTATION OF USEFUL PLANTS BY PHYTOPATHOGENIC MICROORGANISMS AND USE OF THESE COMPOUNDS - Google Patents

Abstract

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

Description

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

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

According to the present invention, a compound of formula (I) is provided: where A is: R1 and R2 are hydrogen; wherein: (i) R3 is R3a, wherein R3a is hydroxyl, ethoxy, propyl, cyclopropyl or 2,2,2-trifluoroethyl; and R4 is R4a, where R4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy C1-3 alkyl, C3 cycloalkyl -4 cycloalkyl or C3-4 alkyl C1-2; or (ii) R3 is R3b, where R3b is isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2-enyl, prop-2-ynyl, prop-2-enyloxy, prop-2-ynyloxy, methoxyethyl, cyclopropylmethyl, or 3-oxetanyl; and R4 is R4b, wherein R4b is C1-4 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2-4 alkyl; and R5 is cyano, C1-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 alkoxy, C1-3 alkyl, fluoroalkoxy C12 C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N,N-di-C1-3 alkylamino C1-3 alkyl; or R5 represents C3-4 cycloalkyl or C3-4 cycloalkylC1-2alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein for R5, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6; R6 represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R5 comprises a substituted C3-4 cycloalkyl or heterocyclyl, such cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or wherein for R3 as defined for each of (i) and (ii), R4 and R5, together with the nitrogen atom to which they are attached, form a cycle selected from 3- oxo-pyrrolidinyl, pyrrolidinyl, 2- oxo-pyrrolidinyl, azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethanone; or a salt or N-oxide thereof; with the proviso that the compound of Formula (I) is not: N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholino-4 -carboxamide, N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-2-carboxamide, or N-isopropyl-N-[ [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-1-carboxamide.

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

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.

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 a composition comprising such compound as an active ingredient, is applied to plants, their parts or their locus.

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

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

As used herein, cyan means a -CN group.

As used herein, the term "hydroxyl" or "hydroxy" means an -OH group.

As used herein, amino means a -NH2 group.

As used herein, the term “C1-5 alkyl” refers to a straight or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, containing no unsaturation, having one to five carbon atoms, and which is attached to the rest of the molecule by a single bond. C2-5 alkyl, C1-3 alkyl and C1-2 alkyl are to be interpreted accordingly. Examples of C1-5 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (t-butyl). A “C1-2 alkylene” group refers to the corresponding definition of C1-2 alkyl, except that such a radical is attached to the rest of the molecule by two single bonds. Examples of C1-2 alkylenes are -CH2- and -CH2CH2-.

As used herein, the term "C1-4 alkoxy" refers to a radical of formula -ORx, where Rx is a C1-4 alkyl radical as generally defined above. The terms C2-4 alkoxy, C1-3 alkoxy and C1-2 alkoxy should be interpreted accordingly. Examples of C1-4 alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and t-butoxy.

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

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

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

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

As used herein, the term "C1-2 alkoxy C1-3 alkyl" refers to the radical of formula Ry-O-Rx- where Ry is a C1-2 alkyl radical as generally defined above, and Rx is an alkylene radical C1-3 as generally defined above.

As used herein, the term "C1-3 hydroxyalkyl" refers to a C1-3 alkyl radical as generally defined above, substituted by one or more hydroxy groups. The term “C1-2 hydroxyalkyl” should be interpreted accordingly.

As used herein, the term "C1-3 cyanoalkyl" refers to a C1-3 alkyl radical as generally defined above substituted by one or more cyano groups.

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

As used herein, the term “N,N-di-C1-3 alkylamino” refers to a -N(Rx)2 radical wherein Rx is the same or different C1-3 alkyl radical as generally defined above.

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

As used herein, the term “N,N-di-C1-3 alkylamino C1-3 alkyl” refers to a C1-3 alkyl radical as generally defined above substituted by an N,N-C1-3 dialkylamino group as defined above.

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

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

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 individually selected heteroatoms of nitrogen , oxygen and sulfur. The heterocyclyl radical can be linked to the rest of the molecule through a carbon atom or heteroatom. Examples of heterocyclyls include, but are not limited to, azetidinyl, oxetanyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl and morpholinyl.

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

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

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).

Compounds of Formula (I) that are not in accordance with the present invention are: - N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ]morpholino-4-carboxamide, and - N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-2-carboxamide - N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-1-carboxamide. The following list provides definitions, including preferred definitions, for the substituents A, R1, R2, R3 (including R3a and R3b), R4 (including R4a and R4b), R5 and R6, with reference to compounds of Formula (I) of 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. A is: R1 is hydrogen. R2 is hydrogen.

In certain embodiments of the invention (embodiment (i)), R3 is R3a, wherein R3a is hydroxyl, ethoxy, propyl, cyclopropyl or 2,2,2-trifluoroethyl; and R4 is R4a, where R4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxyC1-3 alkyl, C3- cycloalkyl 4, or C3-4 cycloalkyl C1-2 alkyl.

According to embodiment (i), preferably R3a is ethoxy or cyclopropyl.

According to embodiment (i), preferably R4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C34 alkynyl, C1-2 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy, C1-2 alkyl, cyclopropyl or C1-2 cyclopropylalkyl. More preferably, R4a is C2-5 alkyl, C3-4 alkenyl or C3-4 alkynyl.

In certain embodiments of the invention (embodiment (ii)), R3 is R3b, wherein R3b represents isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2-enyl, prop-2-ynyl, prop-2- enyloxy, prop-2-ynyloxy, methoxyethyl, cyclopropylmethyl, or 3-oxetanyl; and R4 is R4b, where R4b is C1-4 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2-4 alkyl.

According to embodiment (ii), preferably, R3b is n-butyloxy, cyclopropylmethyl or 3-oxetanyl.

According to embodiment (ii), preferably, R4b is C1-4 alkyl, C1-2 fluoroalkyl, C1-4 cyanoalkyl, C1-4 alkoxy or 1-4 alkoxy C2-4 alkyl. More preferably, R4b is methyl, ethyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, methoxy, ethoxy or C1-2 alkoxy C2-4 alkyl. R5 is cyano, C1-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 alkoxy, C1-3 alkyl, C12 fluoroalkoxy C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N,N-di-C1-3 alkylamino C1-3 alkyl; or R5 represents C3-4 cycloalkyl, C3-4 cycloalkyl, C1-2 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl, heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein for R5, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6. R6 represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R5 comprises a substituted C3-4 cycloalkyl or heterocyclyl, such cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or

Preferably R5 is cyano, C1-3 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-2 cyanoalkyl, C1-2 hydroxyalkyl, C1-2 alkoxy, C1-2 alkyl, fluoroalkoxy C1-2 C1-2 alkyl, C1-2 aminoalkyl, N-C1-2 alkylamino C1-2 alkyl, N,N-di-C1-2 alkylamino C1-2 alkyl; or R5 is cyclopropyl, C1-2 cyclopropylalkyl, heterocyclyl, C1-2 heterocyclylalkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein for R5, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6.

More preferably R5 is C1-3 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-2 cyanoalkyl, C1-2 hydroxyalkyl, C1-2 alkoxy C12 alkyl; or R5 is cyclopropyl, C1-2 cyclopropylalkyl, heterocyclyl, C1-2 heterocyclylalkyl, wherein the heterocyclyl moiety is a 4- or 5-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, wherein for R5, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6.

Even more preferably, R5 is C1-3 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or C1-2 cyanoalkyl, or R5 is cyclopropyl, C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6. Even more preferably, R5 is C1-3 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or C1-2 cyanoalkyl, or R5 is cyclopropyl, C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is halogen, methyl or ethyl. wherein for R3 as defined for each of (i) and (ii), R4 and R5, together with the nitrogen atom to which they are attached, form a cycle selected from 3-oxo-pyrrolidinyl, pyrrolidinyl, 2-oxo -pyrrolidinyl, azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethanone. Preferably, R4 and R5, together with the nitrogen atom to which they are attached, form a cycle selected from morpholino or oxazinanyl.

In certain embodiments of the invention, when R3 is n-butyloxy, R4 may also be hydrogen.

Preferably, the compound according to Formula (I) is selected from a compound 1.1 to 1.28 listed in Table T1 (below).

It is understood that, when in aqueous media, the compounds of Formula (I) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (i.e., the compounds of Formula (I-Ia) and Formula ( I-IIa) as shown below, which can exist in tautomeric form as compounds of formula (I-Ib) and formula (I-IIb)) in the CF3-oxadiazole motif. This dynamic balance may be important for the biological activity of compounds of Formula (I). The designations of A, R1, R2, R3 (including R3a and R3b), R4 (including R4a and R4b), R5 and R6, with reference to the compounds of Formula (I) of the present invention generally apply to the compounds of Formulas (I - I), (I-II), (I-Ia) and (I-IIa), as well as the specific disclosures of combinations of A, R1, R2, R3 (including R3a and R3b), R4 (including R4a and R4b), R5 and R6, as represented in the compounds described in Tables 1.1 to 1.5 or as represented in the compounds described or compounds 1.1 to 1.28 described in Table T1 (below).

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

Compounds of formula (I) can be obtained via a coupling transformation with compounds of formula (II) and compounds of formula (III), wherein X is halogen or OH, preferably halogen, in a suitable solvent (e.g. , dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 °C and 100 °C, and optionally in the presence of a base (e.g., NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-di -isopropylethylamine), or under conditions described in the literature for urea coupling. For examples, see WO 2003/028729, WO 2013/092943, WO 2017/055473 or WO 2014/025128. Furthermore, compounds of formula (I) can optionally be obtained via a coupling transformation with compounds of formula (II) and compounds of formula (III), wherein X is -OH, via a process that converts the -OH to an improved halide leaving group, such as a chloride, for example using triphosgene, phosgene, (COCl)2 or SOCl2, before treatment with the compounds of formula (II). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 1. Scheme 1

Alternatively, compounds of formula (I) can be prepared from compounds of formula (II) via treatment with triphosgene in a suitable solvent (e.g., 1,2-dichloroethane, water, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable aminonucleophiles of formula (IV), in the presence of a suitable base, such as pyridine, K2CO3 or triethylamine. For related examples see WO 2017/055473. This reaction is shown in Scheme 2. Scheme 2

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

Compounds of formula (V) can be prepared from compounds of formula (VI) by treatment with a hydroxylamine hydrochloride salt or a solution of hydroxylamine in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at a temperature between 0 °C and 80 °C. In some cases, better reaction performance may be gained by using a catalyst (e.g., 8-hydroxyquinoline). For related examples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268, WO 2017/055473 and WO 2013/066838. This reaction is shown in Scheme 4. Scheme 4

Compounds of formula (VI) can be prepared from compounds of formula (VII), where Y is halogen, by metal-promoted reaction with a suitable cyanide reagent, such as Pd(0)/Zn(CN) 2 or CuCN, in a suitable solvent (e.g., dimethylformamide or N-methylpyrrolidone) at an elevated temperature between 80 °C and 120 °C. For related examples see US 2007/0155739 and WO 2009/022746. This reaction is shown in Scheme 5. Scheme 5 Compounds of formula (VII), containing a directly bonded unsaturated methylene segment [e.g., -CH2- or -CH(CH3)-], can be prepared from compounds of formula (VIII), in that Y is Br or I, and R4 is not equal to hydrogen, via a base-promoted reaction (e.g., sodium hydride) with a suitable alkylating reagent (e.g., methyl iodide, ethyl iodide or 2-methoxyethyl iodide), in a suitable solvent (e.g. dimethylformamide or N-methylpyrrolidone) at 120 °C. This reaction is shown in Scheme 6. Scheme 6

Compounds of formula (II), wherein R1 is hydrogen, can be prepared from aldehyde compounds of formula (X), via treatment with compounds of formula (IX), in a suitable solvent, (e.g., tetra -hydrofuran or methanol) at a temperature between 25 °C and 75 °C followed by the addition of a reducing agent, such as NaBH4, NaBH3CN or LiAlH4 in a suitable solvent, (e.g. tetrahydrofuran or ethanol) at temperatures between 0°C and 25°C. For related examples, see Gazzola, C. and Kenyon, GL Journal of Labeled Compounds and Radiopharmaceuticals, (1978), 15, 181 and WO 2017/055473. This reaction is shown in Scheme 7. Scheme 7 Alternatively, compounds of formula (II) can be prepared from compounds of formula (XI), where X is Cl, Br, I, OH or OSO2Me, by treatment with amines of formula (IX) in a suitable solvent (e.g. tetrahydrofuran) at a temperature between 25°C and 60°C. For related examples, see Miyawaki, K. et al. Heterocycles (2001), 54, 887, WO 2003/028729, WO 2017/055473 and WO 2013/066839. This reaction is shown in Scheme 8. Compounds of formula (XI) can be prepared from compounds of formula (XII), wherein X is Cl or Br, by treatment with a halogen source [e.g., N-bromosuccinimide (NBS) or N -chlorosuccinimide (NCS)] and a radical initiator [e.g., (PhCO2)2 or azobisisobutyronitrile (AIBN)] in a suitable solvent, such as tetrachloromethane, at temperatures between 55° 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 9. Scheme 9 Compounds of formula (VII), where Y is halogen or CN, can be obtained via coupling transformation with compounds of formula (XIII) and compounds of formula (III), where X is halogen or OH, preferably halogen , in a suitable solvent (e.g., dimethylformamide, dichloromethane, tetrahydrofuran or 2-methyltetrahydrofuran), preferably at a temperature of between 0 °C and 100 °C, and optionally in the presence of a base (e.g. ., NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine), or under conditions described in the literature for urea coupling. Furthermore, compounds of formula (VII) can optionally be obtained via a coupling transformation with compounds of formula (XIII) and compounds of formula (III), wherein X is OH, via a process that converts the -OH into a improved halide leaving group, such as a chloride, for example using triphosgene, phosgene, (COCl)2 or SOCl2, before treatment with the compounds of formula (XIII). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 10. Scheme 10 Alternatively, compounds of formula (VII), where Y is halogen or CN, can be prepared from compounds of formula (XIII) via treatment with triphosgene in a suitable solvent (e.g., 1,2-dichloroethane , acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable aminonucleophiles of formula (IX), in the presence of a suitable base, such as triethylamine. This reaction is shown in Scheme 11. Scheme 11

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

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

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

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

Compounds of formula (XVII) can be prepared from amine compounds of formula (IX) via treatment with triphosgene, optionally in a suitable solvent (e.g., water, acetonitrile, ethyl acetate, tetrahydrofuran, chloroform, or toluene) via the addition of a suitable aminonucleophile of formula (IV), in the presence of a suitable base (e.g., pyridine, triethylamine, K2CO3, NaHCO3, Na2CO3), and at a temperature between 0°C and 25° W. This reaction is shown in Scheme 16. Scheme 16

Alternatively, compounds of formula (XVII) can be obtained by a coupling transformation with amine compounds of formula (IX) and compounds of formula (III), wherein X is halogen, or OH, preferably halogen, in a suitable solvent ( e.g., dimethylformamide, acetonitrile, dichloromethane, or tetrahydrofuran), preferably at a temperature of between 25 °C and 100 °C, and optionally in the presence of a base (e.g., K2CO3, triethylamine, or N, N-diisopropylethylamine), or under conditions described in the literature for coupling a urea. For examples, see WO 2003/028729. Furthermore, compounds of formula (XVII) can optionally be obtained via a coupling transformation with compounds of formula (IX) and compounds of formula (III), wherein X is OH, via a process that converts the -OH into a improved halide leaving group, such as a chloride, for example using triphosgene, phosgene, (COCl)2, or SOCl2, before treatment with the compounds of formula (IX). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 17. Scheme 17

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

Alternatively, compounds of Formula (XI), wherein trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide) in the presence of a base (e.g., pyridine or 4-dimethylaminopyridine) in a suitable solvent, (e.g., ethyl acetate, tetrahydrofuran, 2- methyl tetrahydrofuran, or ethanol), at a temperature between 0 °C and 75 °C. For related examples, see WO 2003/028729, WO 2017/055473, and WO 2010/045251.

This reaction is shown in Scheme 19. Scheme 19

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

Compounds of formula (XIX), where C is hydrogen, OH, OSO2Me, Cl, Br, or I, can be prepared from compounds of formula (XIV), where Y is halogen, via a reaction promoted by metals with a suitable cyanide reagent, such as Pd(0)/Zn(CN)2 or CuCN, in a suitable solvent (e.g. dimethylformamide or N-methylpyrrolidone) at an 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 21. Scheme 21

Compounds of Formula (XIV), where X is Cl, Br, I or OSO2Me and Y is halogen or CN, are either commercially available or can be prepared from compounds of Formula (XX), where Y is halogen or CN, via treatment with a suitable acid source (e.g., hydrochloric acid, hydrobromic acid, or hydroiodic acid), or with a suitable halogen source (e.g., CCl3Br, CCl4, or I2) in the presence of triphenylphosphine, or with methanesulfonyl chloride (ClSO2Me), in a suitable solvent, (e.g. 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 (XX) are commercially available or prepared using known methods. This reaction is shown in Scheme 22. Scheme 22

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.

The compounds of formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for the control of plant pests or in non-living materials for the control of microorganisms that cause spoilage or organisms potentially harmful to the man. The new compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants and by being safe from an environmental point of view. They have very useful curative, preventive and systemic properties and can be used for the protection of various cultivated plants. Compounds of Formula (I) can be used to inhibit or destroy pests occurring on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of different useful plant crops, while also protecting those parts of plants that grow later, e.g., from phytopathogenic microorganisms.

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, their parts or their locus.

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

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

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

Additionally, the invention could be used to protect non-living materials from fungal attack, e.g., construction wood, wall panels and paint.

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

The compounds of Formula (I) can be used for example on peat, ornamental plants such as flowers, shrubs, broad-leaved or evergreen trees, for example conifers, as well as for tree injection, pest management and the like. 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, corn, 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 fruit, 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-shelled fruits, for example almonds, cashews, peanut seeds, hazelnuts, groundnuts, pecans, pistachios and walnuts; palms, e.g. 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, carrot, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines, for example grapes.

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-pyrovyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of genetic improvement or modification. An example of a crop that has been made tolerant to imidazolinones, e.g. imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (Canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant corn varieties, commercially available under the trademarks RoundupReady®, Herculex I® and LibertyLink®.

The term "useful plants" is to be understood as also including useful plants which 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 of bacteria that produce toxins, especially those of the Bacillus genus. Examples of such plants are: YieldGard® (maize variety that expresses a CryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses a CryIA(b) toxin and a CryIIIB(b1) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); Bollgard I® (cotton variety that expresses a CryIA(c) toxin); Bollgard II® (cotton variety that expresses a CryIA(c) toxin and a CryIIA(b) toxin); VIPCOT ® (a cotton variety that expresses a VIP toxin); NewLeaf ® (potato variety that expresses a CryIIIA toxin); NatureGard®Agrisure® GT Advantage (glyphosate tolerance trait GA21), Agrisure® CB Advantage (corn borer (CB) trait Bt11), Agrisure® RW (corn rootworm trait) and Protecta® .

The term “crops” is to be understood as also including crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, to from toxin-producing bacteria, especially those of the Bacillus genus.

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, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins from nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycete toxins; plant lectins, such as pea lectins, barley lectins or whitebell lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, corn RIP, abren, lufin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyltransferase, cholesterol oxidases, ecdysone inhibitors, HMG-COa-reductase, ion channel blockers, such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

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

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.

Processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI 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.

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). 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 that expresses a Cry1Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a Cry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate trace), Agrisure® CB Advantage (Bt11 corn borer (CB) trace) and Protecta®. Additional examples of such transgenic crops are: 1. Corn Bt11 from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 2. Maíz Bt176 from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 3. Maíz MIR604 from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maíz that has been made resistant to insects by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin G protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03/018810. 4. Maíz MON 863 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects. 5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02. 6. Maíz 1507 of Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Corn 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. 7. Maíz NK603 x MON 810 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. It consists of hybrid corn varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. The NK603 x MON 810 corn 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 that confers tolerance to certain Lepidoptera, including the European corn borer.

Compounds of Formula (I) (including any compound described in Tables 1.1 to 1.5 or Tables 2.1 to 2.9, or a compound 1.1 to 1.28 described in Table T1 (below) can be used in the control or prevention of plant pathogenic diseases, especially of phytopathogenic fungi (such as Phakopsora pachyrhizi) on soybean plants.

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

Other transgenic soybean plants may comprise event SYHT0H2 - tolerance to HPPD (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - tolerance to glyphosate (U.S. Patent No. 7,632,985 and related applications and related patents), event MON87708 - dicamba tolerance (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), event DP-356043-5 - glyphosate and ALS tolerance (US U.S. No. US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP- 305423-1 - ALS tolerance (U.S. Patent Application Publication No. US 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents related), event DAS-40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see documents WO 2011/022469, WO 2011/022470, WO 2011/022471, and related applications and patents), event 127 - tolerance to ALS (WO 2010/080829 and related applications and patents), event GTS 40-3-2 - glyphosate tolerance, event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, event FG72 - glyphosate tolerance and isoxaflutole, event BPS-CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.

The term “locus” as used here means fields in or on which plants are growing or where seeds of cultivated plants are sown or where seeds will be placed in the soil. Includes soil, seeds and seedlings, as well as established vegetation.

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

The term "plant propagation material" is understood to denote generative parts of the plant, such as seeds, which can be used for 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 parts of plants may be mentioned. Germinated plants and young plants that must be transplanted after germination or after emergence from the soil can also be mentioned. These young plants can be protected before transplanting through a full or partial dip treatment. Preferably, “plant propagation material” is understood to denote seeds.

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

Suitable carriers and adjuvants, e.g. for agricultural use, may be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97/33890.

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 in water and typically applied as a spray to the area to be treated. The amount of active ingredient can vary from 0.5% to 95% of the concentrate.

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

Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or another 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 organic solvents. non-volatile. In use, these concentrates are dispersed in water or another liquid, and typically applied as a spray to the area to be treated. The amount of active ingredient can vary from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarse particles, and are typically applied undiluted 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, corncobs. crushed corn, crushed peanut shells, sugars, sodium chloride, sodium sulfate, 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.

Dusts 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.

Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell that allows release of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed 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, trapping the active species in liquid form within the granule pores. The granules typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter. Granules are formed by extrusion, agglomeration or compression, or occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

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 vaporization of a low boiling point dispersant solvent carrier, can also be used.

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.

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, cyclo -hexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abiethate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether , N,N-dimethylformamide, dimethyl sulfoxide, 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, methyl iso-amylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, ether propylene glycol monoethyl, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and molecular weight alcohols high alcohol, 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.

Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, seed hulls, cotton, wheat flour, soy flour, pumice, wood flour, nut shell flour and lignin.

A wide variety of surfactants are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, typically comprise from 0.1% to 15% by weight of the formulation. They may have an anionic, cationic, non-ionic or polymeric character and can and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products such as nonylphenol-C.sub ethoxylate. 18 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; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

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

Furthermore, 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, for example, in the spray tank. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.

In this document reference is made to pesticidal agents using their common name, known for example from “The Pesticide Manual”, 15th Edition, British Crop Protection Council 2009.

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

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, for example, fertilizers or micronutrient donors or other preparations, which influence plant growth. These may 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 in conjunction with additional carriers, surfactants or application promoting adjuvants, customarily employed in the formulation art. .

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

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 carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more pesticide-active compounds, for example, an additional fungicidal active ingredient in addition to the compound of Formula (I).

The compound of Formula (I) may be the only 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, when appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.

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, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, fungicides furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, oragnophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, fungicides of thiocarbamate, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides. 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-pyrazolo-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide, acid 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 acid -difluoromethyl-1H-pyrazolo-4-carboxylic (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl-3-difluoromethyl-4H-pyrazolo-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)-ylideneamino-oxymethyl]-phenyl}-2-[(Z)-methoxy-imino]-N-methyl -acetamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl ) phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazol-1-sulfonamide, a-[N-(3-chloro-2, 6-xylyl)-2 -methoxyacetamido]-i-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-dimethylapropl)-2- (2, 4-dichlorophenoxy) propionamide, N- (2-methoxy-5-pyridyl)- cyclopropanecarboxamide, (.+-.)-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-thiazol-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)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methylmethoxyacrylate, (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-methoxyacrylate, (E)-2-[2-[3-(5-methylpyrimidin-2 -yloxy)- phenoxy]phenyl]-methyl 3-methoxyacrylate, (E)-2-[2-[3-(phenylsulfonyloxy)phenoxy]phenyl-3-methyl methoxyacrylate, (E)-2-[2 -[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methyl methoxyacrylate, (E)-2-[2-phenoxyphenyl]-3-methyl methoxyacrylate, (E)-2-[2-(3, Methyl 5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, (E)-2-[2-(3-methoxyphenoxy)phenyl]-methyl 3-methoxyacrylate, (E)-2[2- (2-phenylethen-1-yl)-phenyl]-3-methyl methoxyacrylate, (E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methyl methoxyacrylate, (E )-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methyl methoxyacrylate, (E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy ]phenyl)-methyl 3-methoxyacrylate, (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methyl methoxyacrylate, (E)-2-[2-(3-n -propyloxy-phenoxy)phenyl]3- methyl methoxyacrylate, (E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methyl methoxyacrylate, (E)- 2-[2-[3-(2 -fluorophenoxy)phenoxy]phenyl]-methyl 3-methoxyacrylate, (E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-(4-tert -butyl-pyridin-2-yloxy)phenyl]-3- methyl methoxyacrylate, (E)-2-[2-[3-(3- cyanophenoxy)phenoxy]phenyl]-3-methyl methoxyacrylate, (E)- Methyl 2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy ]phenyl]-3-methyl methoxyacrylate, (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-(3 -(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl] Methyl -3-methoxyacrylate, (E),(E)-2-[2-(5,6-dimethylapyrazin-2-ylmethyloxyminomethyl)phenyl]-methyl 3-methoxyacrylate, (E)- 2-{2-[ Methyl 6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, (E),(E)-2-{ 2-(3-methoxyphenyl)methyloxyminomethyl]-phenyl}- Methyl 3-methoxyacrylate, (E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methylmethoxyacrylate, (E),(E)-2-{ Methyl 2-[6-phenylpyrimidin-4-yl)-methyloxyminomethyl]phenyl}-3-methoxyacrylate, (E),(E)-2-{2-[(4-chlorophenyl)-methyloxyminomethyl]-phenyl}-3 -methyl methoxyacrylate, (E)- 2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methyl methoxyacrylate, (E), (E)-2-{2-[(3-nitrophenyl)methyloxyminomethyl]phenyl}-methyl 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 ethylcarbamate, 3-diiodo-2-propenyl, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl n-butylcarbamate, n-hexylcarbamate 3-iodo-2-propynyl, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenylcarbamate; phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4- chlorophenol, 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenethiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1, 3,5-Thiadiazino-2-thione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acipetaks, alanicarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradine, amisulbrom, amobame, ampropylphos, anilazine, asomate , aureofungin, azaconazole, azafendine, azitirame, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentalurone, bentiavalicarb, bentiazole, benzalkonium chloride, benzamacryl, benzamorph, benzohydroxamic acid, benzovindiflupyr, berberine, betoxazine, biloxazole, binapacryl, biphenyl, bitertanol, bitionol, bixaphene, blasticidin-S, boscalid, bromothalonil, bromuconazole, bupyrimate, butiobate, calcium and butylamine polysulfide, Captafol, Captan, carbamorph, carbendazim, carbendazime, carbendazime hydrochloride, carboxine, carpropamide, carvone, CGA41396, CGA41397, chinomethionate, chitosan, clobenthiazone, chloraniformethane, chloranil, chlorphenazole, chloronebo, chloropicrin, chlorothalonil, chlorozolinate, clozolinate, climbazole, clotrimazole, clozilacone, copper-containing compounds such as copper acetate, copper carbonate, hydroxide copper, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper thallate, copper zinc chromate and Bordeaux mixture, cresol, kofraneb, cuprobam, cuprous oxide, cyazofamide, cyclafuramide, cycloheximide, cyflufenamide, cymoxanil, cipendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, disulfide 1, 1'-di-2-pyridyl dioxide, diclofluanide, diclomezine, diclone, dichlorane , dichlorophene, diclozolin, diclobutrazol, diclocimet, diethofencarb, difenoconazole, diphenzoquat, diflumetorime, O, O-diiso-propyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimetconazole, dimethomorph, dimethyrimole, diniconazole, diniconazole-M, dinobutone , dinocapo, dinoctone, dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrythion, disulfiram, dictatorymphos, dithianone, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicine, dodino, doguadino, drazoloxone, edifenfos, enestroburin, epoxiconazole, etaconazole, eteme, eta boxame , ethyrimole, ethoxyquin, ethylicin, (Z)-N-benzyl-N ([methyl(methyl-thioethylideneamino-oxycarbonyl) amino]thio)-β-ethyl alaninate, etridiazole, famoxadone, fenamidone, fenaminosulfe, fenapanil, fenarimol, fenbuconazole , fenfuram, fenhexamide, fenitropane, fenoxanil, fenpiclonil, fenpicoxamide, fenpropidine, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbame, ferimzone, fluaziname, fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin , fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyra, furcarbanil, furconazole, furfural, furmeciclox, furophanate, gliodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydrargafen, hydroxyisoxazole, himexazole, imazalyl, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butyl carbamate, iso prothiolane, isopyrazam, isothianyl , isovaledione, izopanfos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamide, maneb, mebenil, mecarbinzide, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, meptildinocape , metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole, metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxidine, myclobutanil, myclozolin, nabame, natamycin, neoasozin, dimethyldithiocarbamate nickel, nitrostyrene, nitrothal-iso-propyl, nuarimol, octilinone, ofurace, organomercury compounds, orisastrobin, ostol, oxadixyl, oxasulfuron, oxathiapiproline, ooxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencycurone, penflufen , pentachlorophenol, penthiopyrad, fenamacryl, phenazine oxide, phosdiphene, fosetyl-Al, phosphorous acids, phthalide, picoxystrobin, piperaline, polycarbamate, polyoxin D, polyoxrime, polyrame, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, acid propionic, proquinazide, prothiocarb, prothioconazole, pidiflumetofen, pyracarbolide, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos, piribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyriophenone, pyroquilone, pyroxychlor, pyroxifur, pyrrolnitrin, quaternary ammonium compounds, quinacetol, quinazamide, quinconazole, quinomethionate , quinoxifene, quintazene, rabenzazole, santonin, sedaxane, siltiofame, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, sultropene, tebuconazole, tebfloquine, teclophthalam, technazene, tecorame, tetraconazole, thiabendazole, thiadifluorine, ticiophene, thifluzamide, 2 - (thiocianomethylthio) benzothiazole, thiophanate- methyl, thioquinox, thiram, thiadinyl, thymibenconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimephone, triadimenol, triamiphos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazol, triforin, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin, zarilamide, zineb, zirame, and zoxamide.

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 derivatives of ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin as described in EP-357460, EP-444964 and EP -594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxybendazole, parbendazole and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levadamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulone, and cestocides, such as praziquantel and epsiprantel.

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

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

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

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.

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:

Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chloropyrifos, chlorofenvinphos, chloromephos, demetone, demetone-S-methyl, demetone-S-methylsulfone, dialiphos, diazinone, dichlorvos , dicrotophos, dimethoate, disulfotone, ethione, etoprophos, ethrinphos, fanfur, fenamiphos, fenitrothion, fensulfothione, fenthion, flupyrazophos, phonophos, formotiona, fostiazate, heptenophos, isazophos, isothioate, isoxathione, malathione, methacryphos, methamidophos, methidathione, methyl-parathion, mevinphos, monocrotophos, nalede, omethoate, oxidemetone-methyl, paraoxone, parathion, parathion-methyl, phentoate, phosalone, phospholane, phosphocarb, phosmet, phosfamidone, phorate, phoxime, pirimiphos, pirimiphos-methyl, profenophos, propaphos, proetanphos, prothiophos, pyraclophos, pyridapenthion, quinalfos, sulprophos, temephos, terbufós, tebupirinphos, tetrachlorvinphos, thymtone, triazophos, trichlorophone, vamidothione. Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloretocarb, ethiofencarb, fenoxycarb, fenthiocarb, furatiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m- cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717. 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, bioalethrin, bioalethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI- 85193, cycloprothrin, cyhalothrin, cytithrin, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin , fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin , tralomethrin, Zeta-cypermethrin. Arthropod growth regulators: a) inhibitors of chitin synthesis: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucicloxurone, flufenoxurone, hexaflumurone, lufenuron, novalurone, teflubenzuron, triflumurone, buprofezin, diophenolan, hexithiazox, ethoxazole, chlorophentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

Other antiparasitics: acequinocil, amitraz, AKD- 1022, ANS-118, azadirachtin, Baciilus turingiensis, bensultape, bifenazate, binapacryl, bromopropylate, BTG- 504, BTG-505, campeflor, cartape, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclodene, diafentiurone, DBI-3204, dynactin, dihydroxymethyldihydroxypyrrolidine, dinobutone, dinocape, endosulfan, etiprol, etofenprox, fenazaquine, flumite, MTI-800, fenpyroximate, fluacripyrime, flubenzimine, flubrocitrinate, flufenzine, flufenprox, fluproxifen, halofenprox, hydramethylnone, IKI-220, canemite, NC-196, neem protectant, nidinorterfuran, nitanpyram, SD-35651, WL-108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridabem, pyrimidifem, NC-1111, R-195, RH- 0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifone, tetranactin, thiacloprid, thiocyclamen, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosine, trinactin, verbutin, vertalec, YI-5301. Biological agents: Baciilus thuringiensis ssp aizawai, kurstaki, Baciilus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi. Bactericides: chlortetracycline, oxytetracycline, streptomycin. Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole. The following mixtures of the compounds of Formula (I) with active ingredients are preferred. The abbreviation "TX" designates a compound selected from the group consisting of the compounds described in Tables 1.1 to 1.5, Tables 2.1 to 2.9 or Table T1 (compounds 1.1 to 1.28) (below): an adjuvant selected from the group of substances consisting of oils petroleum (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-benzenesulfonate -dichlorophenyl (IUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amidoflumeth [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenic oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotin (46) + TX, nitrogenate (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, ethyl bromophos (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxime (103) + TX, butoxycarboxyme (104) + TX, butylpyridabene (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, quinomethionate (126) + TX, chlorobenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorofenapyr (130) + TX, chlorophenethol (968) + TX, chlorophensone (970) + TX, chlorofensulfide (971) + TX, chlorofenvinphos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiurone (978) + TX, chloropropylate (983) + TX, chloropyrifos (145) + TX, chloropyrifos-methyl (146) + TX, chlorothiophos (994) + TX, cinerin I (696) + TX, kinerin II (696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamitone (alternative name) [CCN] + TX, crotoxiphos (1010) + TX, cufraneb (1013) + TX, cyantoate (1020) + TX, cyflumetofen (No. CAS Reg.: 400882-07-7) + TX, cyhalothrin (196) + TX, cy-hexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demephione (1037) + TX, demephione-O (1037) + TX, demephione-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialyphos (1042) + TX, diazinone (227) + TX, diclofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dynactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobutone (269 ) + TX, dinocape (270) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinoctone (1090) + TX, dinopentone (1092) + TX, dinosulfone (1097) + TX, dinoterbon (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, ethion (309) + TX, ethoate-methyl (1134) + TX, ethoxazole (320) + TX, ethrinphos (1142) + TX, fenazaflor (1147) + TX, fenazakime (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, phensone (1157) + TX, fentriphanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacripirime (360) + TX, fluazurome (1166) + TX, flubenzimine (1167) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, flueethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorobenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formetanate hydrochloride (405) + TX, formotiona (1192) + TX, formparanate (1193) + TX, gamma-HCH (430) + TX, gliodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, O- isopropyl (methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, iodofenphos (1248) + TX, lindane (430) + TX, lufenurone (490) + TX, malathion (492) + TX, malonobene (1254) + TX, mecarbame (502) + TX, mephospholane (1261) + TX, mesulfen (alternative name) [CCN] + TX, methacryphos (1266) + TX, methamidophos (527) + TX, methidathione (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550 ) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561) + TX , morphothione (1300) + TX, moxidectin (alternative name) [CCN] + TX, nalede (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide ( 1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1:1 zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI -0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxideprophos (1324) + TX, oxydisulfotone (1325) + TX, pp'-DDT (219) + TX, parathion ( 615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phencaptone (1330) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosfamidone (639) + TX, phoxime (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX , pollinactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, propetanphos (673) + TX, propoxur (678 ) + TX, protidathion (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridafenthion ( 701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, quinalfos (711) + TX, quinthiophos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, escradane (1389) + TX, sebufós (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (development code) compound) + TX, sofamide (1402) + TX, spirodiclofen (738) + TX, spiromesifene (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX , sulfluramide (750) + TX, sulfotepe (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrate (763) + TX, TEPP (1417) + TX, terbame (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifone (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiophanox (800) + TX, thiometone (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, trichlorophone (824) + TX, tripenophos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothione (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, an algaecide selected from the group of substances consisting of bethoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutrin [CCN] + TX, diclone (1052) + TX, dichlorophene (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN ] + TX, nabame (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, 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, phenthion (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-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dipyrithione (1105 ) + TX, dodicine (1112) + TX, phenaminosulfe (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + TX, kasugamycin (483) + TX, hydrated kasugamycin hydrochloride (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, sulfate potassium hydroxyquinoline (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 (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, alternative Steinernema bibionis) (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 carpocapsae (alternative) (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-acetate 1-yl 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 (name IUPAC) (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 acetate (IUPAC name) (437) + TX, (Z)-hexadec-13-en-11-en-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,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (name IUPAC) (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, alpha-multistriatin (alternative name) [CCN] + TX, brevicomine (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemona (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en acetate -1-yl (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodec-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) alternate) [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) (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, lineatina (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, ostramon (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11- acetate en-1-ila (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (name alternative) (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, succinate dibutyl (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethylhexanediol (1137) + TX, hexamide [CCN] + TX, methochin-butyl (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 name Abstracts) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, acetate 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl phosphate (IUPAC name) (1066) + TX, dimethylcarbamate 2-(1,3-dithiolan-2-yl)phenyl (IUPAC/Chemical Abstracts name) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX , 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, diethyl 2-chlorovinyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindane-1,3-dione (name IUPAC) (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-) methylcarbamate inyl)amino-3,5-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, acethione (alternative name) [CCN] + TX, acetoprol [CCN] + TX, acrinathrine (9) + TX, acrylonitrile (IUPAC name) (861) + TX , alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidine (alternative name) [CCN] + TX, alixicarb (866 ) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidathione (883) + TX, AVI 382 (code of compound) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX , nitrogenate (889) + TX, Bacillus thuringiensis delta-endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892) + TX, bartrina [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioalethrin (78) + TX, S-cyclopentenyl isomer of bioalethrin (alternative name ) (79) + TX, bioethanometrin [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, ethylbromophos (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiophos (927) + TX, butocarboxime (103) + TX, butonate (932) + TX, butoxycarboxyme (104) + TX, butylpyridabene (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 (IUPAC name) (946) + TX, carbophenothione (947) + TX, carbosulfan (119) + TX, Cartape (123) + TX, Cartape hydrochloride (123) + TX, Cevadine (alternative name) (725 ) + TX, chlorbicyclene (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorofenapyr ( 130) + TX, chlorophenvinphos (131) + TX, chlorfluazurome (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxime (989) + TX, chlorprazophos (990 ) + TX, chloropyrifos (145) + TX, chloropyrifos-methyl (146) + TX, chlorothiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cysmethrin (80) + TX, clocitrin (alternative name) + TX, cloetocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumitoate (1006) + TX, crotamitone ( alternative name) [CCN] + TX, crotoxiphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019 ) + TX, cyanophos (184) + TX, cyanthin (1020) + TX, cyclothrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyfenothrin (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, dazometh (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O ( 1037) + TX, demephione-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialyphos (1042) + TX, diamidaphos (1044) + TX, diazinone (227) + TX, dicaptone (1050) + TX, diclofenthion (1051) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanyl (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) + TX, diflubenzurone (250) + TX, dilor (name alternative) [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, dinoprope (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX , diophenolane (1099) + TX, dioxabenzophos (1100) + TX, dioxacarb (1101) + TX, dioxathione (1102) + TX, disulfotone (278) + TX, diticrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (developmental code) (1118) + TX, emamectin (291) + TX, benzoate of emamectin (291) + TX, EMPC (1120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothione (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonan (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, etiprol (310) + TX, ethoate-methyl (1134) + TX, etoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, ethrinphos (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, fenpyritrin (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, flucofurone (1168) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenorime [CCN] + TX, flufenoxurone (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, phonofos (1191) + TX, formethanate (405 ) + TX, formetanate hydrochloride (405) + TX, formotiona (1192) + TX, formparanate (1193) + TX, fosmethylane (1194) + TX, fospirate (1195) + TX, fosthiazate (408) + TX, fosthiethane ( 1196) + TX, furatiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates ( 422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211 ) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumurone (439) + TX, HHDN (864) + TX, hydramethylnone (443) + TX, hydrogen cyanide (444) + TX, hydroprene ( 445) + TX, hiquincarb (1223) + TX, imidacloprid (458) + TX, imiprotrin (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX , isazophos (1231) + TX, isobenzane (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrine (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472 ) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathione (480) + TX, ivermectin (alternative name) [CCN ] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, iodofenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, quelevane (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirinphos (1251) + TX, lufenurone (490) + TX, lithidathione (1253) + TX, m-cumenyl methylcarbamate (IUPAC name ) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbame (502) + TX, mecarphone ( 1258) + TX, menazone (1260) + TX, mephospholane (1261) + TX, mercurous chloride (513) + TX, mesulfenphos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam- potassium (alternative name) (519) + TX, methamsodium (519) + TX, methacryphos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268) + TX, methidathione (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methochin-butyl (1276) + TX, methotrin (alternative name) ( 533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, chloride methylene [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, methoxadiazone (1288) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothione (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nalede (567) + TX, naphthalene (IUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 ( compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyrame (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX , nitrilacarb complex 1:1 zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novalurone (585) + TX, noviflumurone (586) + TX, O-5-dichloro-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, oxideprophos (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, oils of petroleum (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phencaptone (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636 ) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosfamidone (639) + TX, phosphine (IUPAC name) (640) + TX, phoxime (642) + TX, phoxime-methyl (1340) + TX, pyrimetaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, isomers of polychlorodicyclopentadiene (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, pegone I ( alternative name) [CCN] + TX, precono II (alternative name) [CCN] + TX, precono III (alternative name) [CCN] + TX, primidofós (1349) + TX, profenofos (662) + TX, profluthrin [CCN ] + TX, promacil (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetanphos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, prothiophos (686) + TX, protoate (1362) + TX, protrifenbut [CCN] + TX, pymetrozine (688) + TX, pyraclophos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridalyl (700) + TX, pyridafenthion (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfos-methyl (1376) + TX, quinothione (1380) + TX, quintiophos (1381) + TX , R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, riania (alternative name) (1387) + TX, ryanodina (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradano (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 sodium (444) + TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401 ) + TX, sodium thiocyanate [CCN] + TX, sofamide (1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramate (CCN) + TX, sulcofurone (746) + TX, sulcofuron- sodium (746) + TX, sulfluramide (750) + TX, sulfotepe (753) + TX, sulfuryl fluoride (756) + TX, sulprophos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrate (763) + TX, tebupirinphos (764) + TX, teflubenzurone (768) + TX , tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbame (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX , tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrophos (1428) + TX, thiocarboxime (1431) + TX, thiocyclamen (798) + TX, thiocyclamen hydrogenoxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometone (801) + TX, thionazine (1434 ) + TX, thiosultape (803) + TX, thiosultapesodium (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, triazurone (alternative name) + TX, trichlorophone (824) + TX, trichlormetaphos-3 (name alternative) [CCN] + TX, trichloronate (1452) + TX, tripenophos (1455) + TX, triflumurone (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidothione (847) + TX, vaniliprol [CCN] + TX, veratridine (alternative name) (725) + TX, veratrin (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, zolaprophos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprol [ 736994-63-19] + TX, chlorantraniliprole [500008-45-7] + TX, cyenopirafen [560121-52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, spinetoram [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, triflumezopyrime (disclosed in WO 2012/092115) + TX, a molluscicide selected from the group of substances consisting of bis(oxide) tributyltin) (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloretocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb ( 840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX, a nematicide selected from the group of substances consisting in 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 name /Chemical Abstracts) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3- acid ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN] + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusaphos (109) + TX, carbofuran ( 118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chloropyrifos (145) + TX, chloretocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidaphos (1044) + TX, diclofenthion (1051) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, etoprophos (312) + TX, dibromide ethylene (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, fosthiazate (408) + TX, fosthiethane (1196) + TX, furfural (alternative name) [CCN ] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam - sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, composition from Myrothecium verrucaria (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosfamidone (639) + TX, phosphocarb [CCN] + TX, sebuphos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbame (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC name/Chemical Abstracts ) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (alternative name) compound) 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, arsenic oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX , brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumaclor (1004) + TX, coumafuryl (1005) + TX, coumatetralil (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, diphethialone (249) + TX, diphacinone ( 273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX , HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, magnesium 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, pyrinurone (1371) + TX, scyliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX, a synergistic agent selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (name IUPAC) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324 ) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, 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 zirame (856) + TX, a virucide selected from the group of substances consisting of imannin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a wound protectant selected 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, amisulbrome [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, fenaminestrobin [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, isotianil [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, pirifenox [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, triflumizole [99387-89-0] + TX, triticonazole [13198372-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [6016888-9] + TX, nuarimol [63284-71-9] + TX, bupyrimate [4148343-6] + TX , dimethyrimole [5221-53-4] + TX, ethirimol [2394760-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [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 [7473817-3] + TX, fludioxonil [131341-86-1] + TX, fluindapyr [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, carbendazime [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, clozolinate [84332-86-5] + TX, diclozolin [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozolin [54864-61- 8] + TX, procymidone [32809-16-8] + TX, vinclozolin [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 [55814-41- 0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [ 18367582-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodina [2439-10-3] [112-65-2] (free base) + TX , iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961-52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., 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, oryzastrobin [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, tirame [137-26-8] + TX, zinebe [12122-67-7] + TX, zirame [137-30-4] + TX, capitafol [2425-06-1] + TX ,captan [133-06-2] + TX, diclofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanide [731-27 -1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758 -98-7] + TX, copper oxide [1317-39-1] + TX, copper [53988-93-5] + TX, oxina-copper [10380-28-6] + TX, dinocape [131-72 -6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenfos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphene [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclophos-methyl [57018-049] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloroneb [2675- 77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [5796695-7] + TX, diclone [117-80-6] + TX, diclocimet [139920-324] + TX, diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [11048870-5] + TX, SYP-LI90 (Flumorfe) [211867-47-9] + TX, dithianone [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferinzone [89269-64-7 ] + TX, fluaziname [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 (Ciazofamide) [120116-88-3] + TX, kasugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencicurone [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, proquinazide [ 189278-12-4] + TX, pidiflumetofen [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, quinoxifene [12449518-7] + TX, quintazene [82-68-8] + TX, sulfur [7704-34 -9] + TX, Timorex GoldTM (plant extracts containing tree oil from Stockton Group) + TX, tebufloquine [376645-78-2] + TX, thiadinyl [223580-51-6] + TX, triazoxide [72459- 58-6] + TX, tolprocarb [911499-62-2] + TX, triclopiricarb [902760-40-1] + TX, tricyclazole [41814-782] + TX, triporin [26644-46-2] + TX, validamycin [37248- 47-8] + TX, valifenalate [283159-90-0] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685- 58-1] + TX, fenamacryl + TX, sedaxane [874967-67-6] + TX, trinexapac-ethyl [95266-40-3] + TX, (9-dichloromethylene-1,2,3,4-tetra- 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid hydro-1,4-methane-naphthalen-5-yl)-amide (disclosed in WO 2007/048556) + TX, (3',4' 3-Difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid ,5'-trifluoro-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-di- hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [ 915972-17-7] + TX 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-pyrazolo-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 the procedures described in WO 2010/130767) + TX, 2,6- Dimethyl-1H,5H-[1,4]dithyino[2,3-c:5,6-c']dipyrrole- 1,3,5,7(2H,6H)- tetrona (can be prepared according to the procedures described in WO 2011/138281) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]diti-yne[1,2-c ]isothiazol-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (may 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)-1,1-dioxide -thiazol-5-ylmethoxy)-1,2-benzothiazole (can be prepared according to the procedures described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]- 2-methoxy-N-methyl-acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2-[2-fluoro-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-fluoro-phenyl]propan-2-ol (can be prepared from according to the procedures described in WO 2011/081174) + TX, oxathiapiproline + TX [1003318-67-9], N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl tert-butyl]-2-pyridyl]carbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, 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- formamidin + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (can be prepared according to procedures described in WO 2007/031513) + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazole methanesulfonate - 4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] (can be prepared according to the procedures described in WO 2012/025557) + TX, N-[6-[ But-3-ynyl [(Z)-[(1-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 (may be prepared according to the procedures described in WO 2010/146031) + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate methyl + 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 the procedures described in WO 2013/024082) + TX, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4-(2, 6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774) + TX, (R)-3-(difluoromethyl)-1-methyl -N-[1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2011/162397) + TX, 3-(difluoromethyl)-N-(7 -fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1- [2 -[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072 ) + TX, 1-methyl-4- [3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one ( can be prepared according to the procedures described in WO 2014/051165) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxy-imino-N, 3-dimethyl-pent-3-enamide + TX, (4-phenoxyphenyl)methyl 2-Amino-6-methyl-pyridine-3-carboxylate + TX, N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl -3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide [1255734-28-1] (can be prepared according to the procedures described in WO 2010/130767) + TX, 3-(difluoromethyl)- N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazol-4-carboxamide [1352994-67-2] + TX, N '-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2, 5-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)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl -1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, and 2-(difluoromethyl)-N-[(3R)- 1,1-dimethyl-3-propyl-indan-4-yl )pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and/or WO 2016/139189.

References in square brackets after active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry 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 there described under the entry number given in curly brackets above for the particular compound; for example, the compound "abamectin" is described under accession number (1). When "[CCN]" is added herein above to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible via the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprol" is described at the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are previously referred to by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a “common name,” the nature of the designation used instead 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 none of these designations are used nor a “common name”, an “alternative name” is used. “No CAS Reg” means the Chemical Abstracts Registration Number.

The mixture of active ingredients of compounds of Formula (I) selected from a compound 1.1 to 1.28 described in Table T1 (below) or a compound of Formula (I) described in Tables 1.1 to 1.5 or Tables 2.1 to 2.9 (below), and an active ingredient as described above, are preferably in a mixing ratio of 100:1 to 1:6,000, especially 50:1 to 1:50, more especially in a ratio of 20:1 to 1:20, more especially even from 10:1 to 1:10, most especially from 5:1 and 1:5, with special preference being given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 of the similarly preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6,000, or 1:3,000, or 1:1,500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are by weight.

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

Mixtures comprising a compound 1.1 to 1.28 described in Table T1 or a compound of Formula (I) described in Tables 1.1 to 1.5 or tables 2.1 to 2.9 (below) and one or more active ingredients as described above can be applied, e.g. , in a single “ready-to-mix” form, in a combined spray mixture composed of separate formulations of the individual active ingredient components, such as a “mix 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 those described in Tables 1.1 to 1.5 or 2.1 to 2.9 (below), or Table T1 (below), and the active ingredient(s) such as described above, is not essential to the practice of the present invention.

The compositions according to the invention may also comprise additional solid or liquid auxiliaries, such as stabilizers, e.g. non-epoxidized or epoxidized vegetable oils (e.g. coconut oil, rapeseed oil or epoxidized soybean oil), defoamers, e.g. silicone, 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.

The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by crushing, screening and/or compressing 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 (auxiliary). Such processes for preparing the compositions and the use of compounds of Formula (I) for preparing these compositions are also an object of the invention.

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 compound preferred individual compound as defined above, or of 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, e.g. useful plants such as crop plants, their propagating material e.g. seeds, harvested crops e.g. harvested food crops or non-living materials by insects or by phytopathogenic microorganisms , preferably fungal organisms.

A further aspect of the invention relates to a method for controlling or preventing an infestation of plants, e.g. useful plants, such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. food crops harvested, or from non-living materials by insects or by phytopathogenic or spoilage microorganisms 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 ingredient active to plants, parts of plants or their locus, their propagating material or any part of non-living materials.

Means of control or prevention that reduce infestation by microorganisms or phytopathogenic or spoilage organisms potentially harmful to humans, especially fungal organisms, to such a level that improvement can be demonstrated.

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 mentioned compounds, is the foliar application. The frequency of application and the application rate will depend on the risk of infestation by the corresponding pathogen or insect. However, compounds of Formula (I) can also penetrate the plant through the roots 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 (application to the soil). In irrigated rice crops, such granules can be applied to the irrigated rice field. The compounds of Formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

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

Advantageous application rates typically 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 soaking agent, convenient dosages range from 10 mg to 1 g of active substance per kg of seeds.

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

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.

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 powder (DS), a seed treatment emulsion (ES), a flowable concentrate for seed treatment. seed treatment (FS), a seed treatment solution (LS), a water-dispersible seed treatment powder (WS), a seed treatment capsule suspension (CF), a 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), an 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 concentrate soluble (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wetting powder (WP) or any formulation technically possible in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in a conventional manner, e.g., 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. In particular, Formulations to be applied in spray forms, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO and the like), wetting 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.

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

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

Although it is preferable to formulate commercial products as concentrates, the end user will typically use diluted formulations. Table 1.1: This table discloses 22 specific compounds of formula (T-1): wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is hydroxy, and NR4(R5) is as defined below in Table 1. Each of Tables 1.2 to 1.5 (which follow Table 1.1) makes available 22 individual compounds of formula (T-1) in which A, R1, R2, and R3 are as specifically defined in Tables 1.2 to 1.5, which refer to Table 1, in which -NR4(R5) is specifically defined. Table 1 Table 1.2: This table discloses 22 specific compounds of formula (T-1), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is ethoxy and -NR4(R5) is as defined above in Table 1 Table 1.3: This table discloses 22 specific compounds of formula (T-1), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is propyl and -NR4(R5) is as defined above in the Table 1. Table 1.4: This table discloses 22 specific compounds of formula (T-1), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is cyclopropyl and -NR4(R5) is as defined above in Table 1. Table 1.5: This table discloses 22 specific compounds of formula (T-1), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is 2,2,2-trifluoroethyl and -NR4(R5 ) is as defined above in Table 1. Table 2.1: This table discloses 23 specific compounds of formula (T-2): wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is isopropyl and NR4(R5) is as defined below in Table 2. Each of Tables 2.2 to 2.9 (which follow Table 2.1) makes available 23 individual compounds of formula (T-2) in which A, R1, R2, and R3 are as specifically defined in Tables 2.2 to 2.9, which refer to Table 2, in which -NR4(R5) is specifically defined. Table 2 Table 2.2: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is isobutyl and -NR4(R5) is as defined above in Table 2 Table 2.3: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is prop-2-enyl and -NR4(R5) is such as defined above in Table 2. Table 2.4: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is prop-2-ynyl and -NR4( R5) is as defined above in Table 2. Table 2.5: This table discloses 23 specific compounds of formula (T-2), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is propyloxy and -NR4 (R5) is as defined above in Table 2. Table 2.6: This table discloses 23 specific compounds of formula (T-2), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is butyloxy and - NR4(R5) is as defined above in Table 2. Table 2.7: This table discloses 23 specific compounds of formula (T-2), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is methoxyethyl and -NR4(R5) is as defined above in Table 2. Table 2.8: This table discloses 23 specific compounds of formula (T-2), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is cyclopropylmethyl and -NR4(R5) is as defined above in Table 2. Table 2.9: This table discloses 23 specific compounds of formula (T-2), wherein A is 1,4-phenylene, R1 and R2 are hydrogen, R3 is oxetan-3-yl and -NR4(R5) is as defined above in Table 2.

EXAMPLES

The following Examples serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy 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.

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., greater biological activity , an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physicochemical properties or increased biodegradability).

Throughout this description, temperatures are presented in degrees Celsius (°C) and "p.f." means melting point. LC/MS stands for Liquid Chromatography Mass Spectroscopy and the description of the devices and method (Methods A, B and C) 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) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650 Mass range: 100 to 900 DAD Wavelength Range (nm): 210 to 500 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) Column type: Waters UPLC ACQUITY HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60°C.

The description of the LC/MS device and method B 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 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) Column type: Waters UPLC ACQUITY HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60°C.

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

Spectra were recorded on a Waters Mass Spectrometer (ACQUITY UPLC) (single quadrupole mass spectrometer SQD, SQDII) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30V , Extractor: 3.00 V, Source Temperature: 150 °C, Desolvation Temperature: 400 °C, Cone Gas Flow: 60 L/h, Desolvation Gas Flow: 700 L/h, Mass Range: 140 to 800 Da), DAD wavelength range (nm): 210 to 400, and a Waters Acquity UPLC: Solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 x 2.1 mm, Temp: 60 °C; DAD wavelength range (nm): 210 to 500, Solvent Gradient: A = Water/Methanol 9:1, 0.1% formic acid, B= Acetonitrile+ 0.1% formic acid, gradient: B to 0-100% in 2.5 min; Flow (mL/min) 0.75

The description of the LC/MS device and method D 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 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) Column type: Waters UPLC ACQUITY HSS T3; Column length: 30 mm; Column inner diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60°C.

Where 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 stereoselective synthetic techniques, e.g., using chiral starting materials. Formulation Examples

The active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a suitable mill, creating humectant powders that can be diluted with water to give rise to suspensions of the desired concentration.

The active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a suitable mill, resulting in powders that can be used directly for seed treatment.

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

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

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

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

The finely crushed 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. Using these dilutions, live plants as well as plant propagation material can be treated and protected from infestation by microorganisms by spraying, pouring or immersing.

The finely crushed 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. Using these dilutions, live plants as well as plant propagation material can be treated and protected from infestation by microorganisms by spraying, pouring or immersing.

Suspension of slow release capsules 28 parts of a combination of the compound of Formula I are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer and 51.6 parts water until the desired particle size is achieved.

To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete.

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

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 DIPEA = = N,N-di- isopropylethylamine DMA = dimethylacetamide DMF = dimethylformamide EtOAc = ethyl acetate EtOH = ethyl alcohol HCl = hydrochloric acid pf = melting point MeOH = = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide TFAA = trifluoroacetic acid anhydride THF = tetrahydrofuran

Preparative Examples

Using the synthetic techniques described both above and below, compounds of formula (I) can be prepared accordingly. Example 1: This example illustrates the preparation of N-cyclopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinane-2-carboxamide (Compound 1.4 from Table T1) Step 1: Preparation of N'-hydroxy-4-methyl-benzamidine

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), hydroxylamine carbonate (41.1 g, 0.58 mol), potassium (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. The volatiles were removed under reduced pressure and the reaction contents were filtered, washed with water, and dried under vacuum to provide 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

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 solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride, water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by 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, no mass detected. 1H NMR (400 MHz, CDCl3) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.41 (s).

Step 3a: Preparation of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in tetrachloromethane (480 mL) under argon was heated to 70 °C. AIBN (4.03 g, 24 mmol) was added and the reaction mixture was stirred at 65 °C for 18 hours. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/EtOAc eluent gradient 100:0 to 95:5) to provide 44.7 g of the title compound as a white oil. mp: 58-63°C. 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s). 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole was isolated as a by-product as a white solid. mp: 61-66°C. 1H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H). 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

A 1:9 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) diethylphosphite (4.7 mL) was added , 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 crude product was purified by flash chromatography on silica gel (cyclohexane:EtOAc eluent gradient 99:1 to 9:1) to give 7.10 g of the title compound as a white solid. mp: 58-63°C. 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s).

Alternatively, the title compound can be prepared using an analogous procedure as described in WO 2013/066839.

To a stirred solution of tert-butyl N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-carbamate, (23.1 g, 65.4 mmol) in 1,4-dioxane (196 mL) heated to 70 °C was added dropwise an HCl solution (41 mL, 163 mmol, 4 M 1,4-dioxane). The precipitation of a white solid and the release of gas began 5 minutes after addition. The mixture was stirred for 6 hours at 70°C. The white suspension was cooled to 23°C, filtered, washed with 1,4-dioxane and dried under reduced pressure at 40°C to give 17.3 g of [4-[5-(trifluoromethyl)-1,2 hydrochloride ,4-oxadiazol-3-yl]phenyl] methanamine as a yellow solid.

Step 4: Preparation of 1-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanamine

A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (2.50 g, 8.1 mmol) in dichloromethane (5 mL) was added over 2 hours to the room temperature to a solution of cyclopropanamine (3.7 g, 65 mmol) and N-ethyl-N-isopropyl-propan-2-amine (1.4 mL, 8.1 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 30 minutes, poured into water and then extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (cyclohexane/EtOAc eluent gradient 1:0 to 1:1) to give 1.18 g of the title compound as a white solid, LC/MS (Method A) retention time = 0.71 minutes, 300 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.06 (d, 2H), 7.49 (d, 2H), 3.92 (s, 2H), 2.18 (m, 1H), 1.85 (s l, 1H), 0.42 (m, 2H), 0.39 (m, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.36 (s). Step 5: Preparation of N-cyclopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinane-2-carboxamide

In a dry container under argon, triphosgene (41 mg) was dissolved in 1,2-dichloroethane (5 mL). The clear solution was cooled to 0°C. Then, a solution of oxazinane hydrochloride (43 mg) and triethylamine (0.1 mL) in 1,2-dichloroethane (2.5 mL) was added at 0 °C. The reaction mixture was stirred for 4 hours at room temperature. Then, a solution of N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanamine (40 mg) and N,N-diethylethanamine (0.04 mL) in 1,2-dichloroethane (2.5 mL) was added. The resulting mixture was stirred for 18 hours at room temperature. Then, aqueous sodium bicarbonate was added to the reaction mixture. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated. The crude residue was purified by silica gel chromatography using a cyclohexane/ethyl acetate gradient to give 52 mg of the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm: 8.08 (d, 2H), 7.44 (d, 2H), 3.93 (m, 2H), 3.51 (m, 2H), 2.70 (m, 1H), 1.81 (m, 2H), 1.72 (m, 2H), 0.72 (m, 4H). Example 2: This example illustrates the preparation of the intermediate N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]methanamine.

A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (15 g, 46.9 mmol) in THF (20 mL) was added dropwise to the room temperature to a 2M solution of methylamine in THF (120 mL, 234.5 mmol). The mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the resulting crude material was purified by flash chromatography on silica gel (cyclohexane/EtOAc eluent gradient 1:0 to 1:1) to give 10.3 g of the title compound as a transparent oil. LC/MS (Method A) retention time = 0.58 minutes, 258 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.08 (d, 2H), 7.47 (d, 2H), 3.84 (s, 2H), 2.48 (s, 3H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.39 (s). Example 3: This example illustrates the preparation of the intermediate 2,2,2-trifluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine.

To a solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.5 g, 4.69 mmol) in dichloromethane (10 mL) was added dropwise N-ethyl-N-isopropyl-propan-2-amine (0.82 mL, 4.69 mmol) followed by 2,2,2-trifluoroethanamine (2.94 mL, 37.5 mmol). The reaction mixture was stirred at room temperature for 24 hours, poured into water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (cyclohexane/EtOAc eluent gradient 1:0 to 0:1) to give 1.53 g of the title compound as a transparent oil. 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.51 (d, 2H), 4.00 (s, 2H), 3.22 (q, 2H), 1.71 (s, 1H). Example 4: This example illustrates the preparation of the intermediate N-propoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.30 g, 4.06 mmol) in dichloromethane (10 mL) was added dropwise to a solution of O-propylhydroxylamine hydrochloride (3.74 g, 32.5 mmol) and DIPEA (6.40 mL, 36.6 mmol) in dichloromethane (6 mL). The reaction mixture was stirred at room temperature for 24 hours, poured into water and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude material was purified by flash chromatography on silica gel (cyclohexane/EtOAc eluent gradient 1:0 to 1:1) to give 0.92 g of the title compound as a transparent oil. LC/MS (Method A) retention time = 1.12 minutes, 302 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.02 (d, 2H), 5.70 (sl, 1H), 4.11 (s, 2H), 3.59 (m, 2H), 1.52 (m, 2H), 0.86 (s, 3H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.33 (s). Example 5: preparation of 1-ethoxy-3-methyl-3-prop-2-ynyl-1- [[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] urea (Compound 1.1 from Table T1) Step 1: Preparation of N-ethoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

A stirred solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (2.50 g, 7.82 mmol) in dichloromethane (10 mL) was added dropwise at room temperature to a stirred solution of o-ethylhydroxylamine hydrochloride (6.10 g) and N-ethyl-N-isopropyl-propan-2-amine (12.3 ml). The mixture was stirred at room temperature for 24 hours. Then, a second portion of o-ethylhydroxylamine hydrochloride (6.10 g) and N-ethyl-N-isopropyl-propan-2-amine (12.3 mL) was added and the mixture was stirred at room temperature for 72 hours. Then, the reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (cyclohexane:ethyl acetate gradient) to give 2.03 g of the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.52 (d, 2H), 5.72 (s l, 1H), 4.11 (s, 2H), 3.68 (q, 2H), 1.10 (t, 3H).Step 2: Preparation of 1-ethoxy-3-methyl-3-prop-2-ynyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea N-ethoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine (50 mg ) was dissolved in dichloromethane (0.52 mL) and N,N-dimethylformamide (0.17 mL). One portion of CDI (45 mg) was added to this suspension at room temperature. The suspension slowly turned into a clear solution. The mixture was stirred for 1 hour at room temperature. Next, N-methylpropyl-2-yn-1-amine (63 mg) was added to the reaction mixture at room temperature. The mixture was stirred for 18 hours at room temperature. Then, water and ethyl acetate were added to the mixture and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography using a cyclohexane/ethyl acetate gradient to give 25 mg of the title compound as a clear oil. LC/MS (Method A) retention time = 1.11 minutes, 383 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.10 (d, 2H), 7.55 (d, 2H), 4.63 (s, 2H), 4.16 (d, 2H), 3.81 (q, 2H), 3.08 (s, 3H), 2.28 (t, 1H), 1.17 (t, 3H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.36 (s).

The following procedure was used in a combinatorial manner using appropriate building blocks (compounds (II) and (III)) to provide the compounds of Formula (I). Compounds prepared via the following combinatorial protocols were analyzed using LC/MS Method B.

By way of example, acid derivatives of formula (III) (0.0375 mmol in 375 μL of DMA) were transferred to a 96-slot deep well plate (DWP96) containing the derivatives [[5-(trifluoromethyl)-1, 2,4-oxadiazol-3-yl]aryl]methanamine of formula (II) (0.03 mmol) and DIPEA (0.09 mmol) in 250 μL of DMA, followed by the addition of BOP-Cl (0.06 mmol ) dissolved in DMA (250 μL). The DWP was sealed and stirred at 50 °C for 18 hours. The solvent was removed under a stream of nitrogen. The resulting crude residues were solubilized in a mixture of MeOH (250 μL) and DMA (500 μL) and directly subjected to purification by preparative LC/MS which provided the compounds of formula (I) in 10-85% yields.

The following procedure was used in a combinatorial manner using appropriate building blocks (compounds (II) and (IV)) to provide the compounds of Formula (I). Compounds prepared via the following combinatorial protocols were analyzed using LC/MS Method B.

By way of example, portions of triphosgene (5.94 mg) in DCE (0.3 mL) were transferred at 0 °C to a 96-slot deep well plate (DWP96) containing amine derivatives [HN(R4)R5] of formula (IV) (0.05 mmol) and triethylamine (0.12 mmol) in 200 μL of DMA. The reaction mixtures were stirred at room temperature for 30 minutes, then [[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine derivatives of formula (II) (0.05 mmol) 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 Station. The crude residues were solubilized in a mixture of MeOH (200 μL) and DMA (600 μL) and directly subjected to purification by preparative LC/MS which provided the compounds of formula (I) in yields of 10-85%. Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate, by standard physical separation techniques such as chiral reversed-phase chromatography, or by stereoselective synthetic techniques, (e.g., using chiral departure). Table T1: Melting point (pf) and/or retention times (RT) data for compounds according to Formula (I):

BIOLOGICAL EXAMPLES: General examples of testing leaf discs in well plates:

Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. Leaf discs or segments are placed on multi-well plates (24-well format) on 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. The inoculated leaf discs or segments are incubated under defined conditions (temperature, relative humidity, light, etc.), according to the respective test system. A single disease level assessment is performed 3 to 14 days 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 testing in well plates:

Mycelia fragments or conidial suspensions of a fungus, 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/mycelium fragments is then added to generate a final concentration of the tested compound. Test plates are incubated in the dark at 24°C and 96% relative humidity. Inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and the percentage of antifungal activity relative to the untreated check is calculated.

Example 1: Fungicidal activity against Puccinia recondita f. sp. tritici/wheat/preventative on leaf discs (Brown Rust)

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 suspension of fungal spores 1 day after application. The inoculated leaf segments were incubated at 19 °C and 75% relative humidity (RH) under a light regime of 12 hours light/12 hours dark in a climate-controlled chamber, and the activity of a compound was evaluated as a percentage control. of disease, compared with no treatment, when an appropriate level of disease damage appears on untreated control leaf segments (7 to 9 days after application).

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) 1.1, 1.4, 1.6, 1.7, 1.8, 1.11, 1.14, 1.15, 1.16, 1.19, 1.21, 1.22, 1.23 and 1.28.

Example 2: Fungicidal activity against Puccinia recondita f. sp. tritici/wheat/curative on leaf discs (Brown Rust)

Leaf segments of wheat cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are then inoculated with a suspension of fungal spores. The plates were stored in the dark at 19 °C and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. Leaf segments were incubated at 19 °C and 75% relative humidity under a light regime of 12 hours light/12 hours dark in a climate-controlled chamber, and the activity of a compound was evaluated as percentage control of the disease, compared with no treatment, when an appropriate level of disease damage appears on untreated control leaf segments (6 to 8 days after application).

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

Compounds (from Table T1) 1.1, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.10, 1.11, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21 and 1.22.

Example 3: Fungicidal activity against Phakopsora pachyrhizi/soybean/preventative on leaf discs (Asian soybean rust)

Soybean leaf discs are placed on water agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate-controlled chamber of 24-36 hours in darkness at 20 °C and 75% RH, the leaf discs are maintained at 20 °C with 12 h light/day and 75% RH. The activity of a compound is evaluated as percentage of disease control compared to no treatment when an appropriate level of disease lesions appears on untreated check leaf discs (12 to 14 days after application).

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) 1.1, 1.4, 1.6, 1.7, 1.11, 1.15, 1.16 and 1.19.

Example 4: Fungicidal activity against a liquid culture of Glomerella lagenari um(Colletotri chum lagenarium)/cucumber/preventive (Anthracnose)

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

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

Compounds (from Table T1) 1.1, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.21, 1.22, 1.23, 1.24, 1.25, 1.25, 1.26, 1.27 and 1.28.

Claims (13)

1. Compound of formula (I): characterized by the fact that A is: R1 and R2 are hydrogen; wherein (i) R3 is R3a, wherein R3a is hydroxyl, ethoxy, propyl, cyclopropyl or 2,2,2-trifluoroethyl; and R4 is R4a, where R4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy C1-3 alkyl, C3 cycloalkyl -4 cycloalkyl or C3-4 alkyl C1-2; or (ii) R3 is R3b, where R3b is isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2-enyl, prop-2-ynyl, prop-2-enyloxy, prop-2-ynyloxy, methoxyethyl, cyclopropylmethyl or 3-oxetanyl; and R4 is R4b, wherein R4b is C1-4 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2-4 alkyl; and R5 is cyano, C1-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 alkoxy, C1-3 alkyl, fluoroalkoxy C1-2 C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N,N-di-C1-3 alkylamino C1-3 alkyl; or R5 represents C3-4 cycloalkyl or C3-4 cycloalkylC1-2 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4 to 6 non-aromatic ring members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein for R5, any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from from R6; R6 represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R5 comprises a substituted C3-4 cycloalkyl or heterocyclyl, such cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or wherein for R3 as defined for each of (i) and (ii), R4 and R5, together with the nitrogen atom to which they are attached, form a cycle selected from 3- oxo-pyrrolidinyl, pyrrolidinyl, 2- oxo-pyrrolidinyl, azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4-yl or 1-piperazin-4-yl ethanone; or a salt or N-oxide thereof; with the proviso that the compound of Formula (I) is not: N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholino-4 -carboxamide, N-isopropyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-2-carboxamide or N-isopropyl-N-[[ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-1-carboxamide. 2. Compound according to claim 1, characterized by the fact that R3a is ethoxy or cyclopropyl. 3. Compound according to claim 1 or 2, characterized by the fact that R4a is C2-5 alkyl, C3-4 alkenyl or C3-4 alkynyl. 4. Compound according to claim 1, characterized by the fact that R3b is n-butyloxy, cyclopropylmethyl or 3-oxetanyl. 5. Compound according to any one of claims 1 or 4, characterized in that R4b is C1-4 alkyl, C1-2 fluoroalkyl, C1-4 cyanoalkyl, C14 alkoxy or C1-4 alkoxy C2-4 alkyl. 6. Compound according to any one of claims 1, 4 or 5, characterized in that R4b is methyl, ethyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, methoxy, ethoxy or C1-2 alkoxy alkyl 2-4 . 7. Compound according to any one of claims 1 to 6, characterized in that R5 is C1-3 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C34 alkynyl or C1-2 cyanoalkyl, or R5 is cyclopropyl or C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6. 8. Compound according to any one of claims 1 to 7, characterized in that R5 is C1-3 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or C1-2 cyanoalkyl, or R5 is cyclopropyl or C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, wherein R6 is halogen, methyl or ethyl. 9. Compound according to any one of claims 1, 2 or 4, characterized by the fact that R4 and R5, together with the nitrogen atom to which they are linked, form a cycle selected from morpholino or oxazinanyl. 10. Agrochemical composition characterized by the fact that it comprises a fungicidal effective amount of a compound of Formula (I), as defined in any one of claims 1 to 9. 11. Composition, according to claim 10, characterized by the fact that it additionally comprises at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier. 12. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized in that a fungicidal effective amount of a compound of Formula (I), as defined in any one of claims 1 to 9, or a composition comprising that compound as an active ingredient is applied to plants, their parts or their locus. 13. Use of a compound of Formula (I), as defined in any one of claims 1 to 9, characterized by the fact that it is as a fungicide, wherein said use excludes methods of treating the human or animal body by surgery or therapy .