BR112019020734B1 - Compounds derived from oxadiazole, agrochemical composition, method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms and use of said 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

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

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

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

[0004] where

[0005] A is

[0006] R1, R2 and R3 are hydrogen;

[0007] R4 represents C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C1-2 alkoxy C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C12 alkyl ;

[0008] R5 represents cyano, C3-5 alkyl, C13 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-4 alkoxy, C1-3 hydroxyalkyl, C12 alkoxy C1- alkyl 3, C1-2 fluoroalkoxy C1-3 alkyl, C13 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl, N,N-di-alkylamino C1-3 C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl alkyl C12; or

[0009] R5 represents C3-4 cycloalkyl or C34 cycloalkyl C1-2 alkyl, in which the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclyl C1-2 alkyl, in which the heterocyclyl moiety is a 4- or 6-membered non-aromatic ring that 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;

[0010] R6 represents cyano, fluorine, chlorine, amino, hydroxyl, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; and wherein when R5 comprises a substituted C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group;

[0011] or a salt or N-oxide thereof;

[0012] with the condition that the compound of Formula (I) is not:

[0013] 1,1-Bis(2-methoxyethyl)-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea; or

[0014] 1-cyclopropyl-1-prop-2-ynyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea.

[0015] Surprisingly, it was discovered that the new compounds of Formula (I) have, for practical purposes, a very advantageous level of biological activity to protect plants against diseases that are caused by fungi.

[0016] According to a second aspect of the invention, an agrochemical composition comprising a fungicidal effective amount of a compound of Formula (I) is provided. Such an agricultural composition may further comprise at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier.

[0017] According to a third aspect of the invention, there is provided a method of controlling or preventing the infestation of useful plants by phytopathogenic microorganisms, in which a fungicidal effective amount of a compound of Formula (I), or of a composition comprising this compound as an active ingredient is applied to plants, their parts or their location.

[0018] 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.

[0019] As used herein, the term “halogen” or “halo” refers to fluorine (fluoro), chlorine (chlorine), bromine (bromine) or iodine (iodine), preferably fluorine, chlorine or bromine.

[0020] As used herein, cyan designates a -CN group.

[0021] As used herein, the term "hydroxyl" or "hydroxy" designates an -OH group.

[0022] As used herein, amino designates a -NH2 group.

[0023] As used herein, the term “C1-5 alkyl” refers to a straight or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, not containing any unsaturation, having from one to five carbon atoms and which it is linked to the rest of the molecule by a single bond. C2-5 alkyl, C1-3 alkyl and C1-2 alkyl should be interpreted accordingly. Examples of C1-5 alkyls 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 C1-2C alkyl, except that such a radical is linked to the rest of the molecule by two single bonds. Examples of C1-2 alkylenes are -CH2- and -CH2CH2-.

[0024] 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 C1-3 alkoxy and C1-2 alkoxy should be interpreted accordingly. Examples of C1-4 alkoxys include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and t-butoxy.

[0025] As used herein, the term “C1-3 fluoroalkyl” refers to a C1-3 alkyl radical as generally defined above substituted by one or more fluorine atoms. Examples of C1-3 fluoroalkyls include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.

[0026] As used herein, the term "C3-4 alkenyl" relates to a linear or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one double bond that may have the (E) configuration - or (Z)-, having three or four carbon atoms, which is linked to the rest of the molecule by a single bond. Examples of C3-4 alkenyls include, but are not limited to, prop-1-enyl, allyl, and but -1-enyl.

[0027] As used herein, the term “C3-4 haloalkenyl” refers to a C3-4 alkenyl radical as generally defined above substituted by one or more same or different halogen atoms.

[0028] As used herein, the term “C3-4 alkynyl” refers to a linear 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.

[0029] As used herein, the term "C1-2 alkoxy C1-2 alkyl" refers to the radical of formula Ry-O-Rx- where Ry is a C1-2 alkyl radical as generically defined above, and Rx is a C1-2 alkylene radical as generally defined above.

[0030] 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.

[0031] As used herein, the term “C1-3 cyanoalkyl” refers to a C1-3 alkyl radical as generally defined above replaced by a cyano group.

[0032] As used herein, the term “C1-3 aminoalkyl” refers to a C1-3 alkyl radical as generally defined above substituted by an amino group.

[0033] As used herein, the term “C1-3 alkylamino” refers to a -HNRx radical wherein Rx is a C13 alkyl radical as generically defined above.

[0034] As used herein, the term “N,N-C1-3 dialkylamino” refers to a radical -N(Rx)2 where Rx is the same or different C1-3 alkyl radical as generically defined above.

[0035] As used herein, the term “N-aminoalkyl C1-3 alkyl” refers to a C1-3 alkyl radical as generally defined above substituted by a C1-3 alkylamino group as defined above.

[0036] As used herein, the term “N,N-C1-3 dialkylamino 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.

[0037] As used herein, the term “C3-4 cycloalkyl” refers to a stable monocyclic ring radical that is saturated or partially unsaturated and contains 3 or 4 carbon atoms. Examples of C3-4 cycloalkyl, cyclopropyl, cyclobutyl.

[0038] As used herein, the term "C3-4 cycloalkyl C1-2 alkyl" refers to a C3-4 cycloalkyl ring as defined above linked to the rest of the molecule by a C1-2 alkylene radical as described above. Examples of C3-4 cycloalkyl C1-2 alkyl include, but are not limited to, cyclopropylmethyl and cyclobutylethyl.

[0039] As used herein, the term "heterocyclyl" or "heterocyclic" refers to a stable, saturated or partially saturated, 4 to 6 membered, non-aromatic monocyclic ring comprising 1, 2 or 3 selected heteroatoms individually of nitrogen, oxygen and sulfur. The heterocyclyl radical 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.

[0040] 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 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).

[0041] In each case, the compounds of Formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g. in an agronomically usable or agrochemically acceptable salt form.

[0042] 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.

[0043] Compounds of formula (I) that are not in accordance with the present invention are: 1,1-bis(2-methoxyethyl)-3-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea; It is 1-cyclopropyl-1-prop-2-ynyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea.

[0044] The following list provides definitions, including preferred definitions, for the substituents A, R1, R2, R3, R4, R5 and R6 with reference to the compounds of Formula (I) according to the invention. For any of these substituents, any of the definitions provided below may be combined with any definition of any other substituent provided below or elsewhere in this document.

[0045] A is:

[0046] R1, R2 and R3 are hydrogen.

[0047] R4 represents C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C1-2 alkoxy C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C12 alkyl . Preferably, R4 is C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-2 cyanoalkyl, C1-2 alkoxy, C1-2 alkyl, cyclopropyl or cyclopropylmethyl. More preferably, R4 is n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, C3-4 alkenyl, C3-4 alkynyl, cyanomethyl, cyanoethyl, methoxymethyl, ethoxymethyl, methoxyethyl , cyclopropyl or cyclopropylmethyl.

[0048] R5 represents cyano, C3-5 alkyl, C13 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-4 alkoxy, C1-3 hydroxyalkyl, C12 alkoxy C1- alkyl 3, C1-2 fluoroalkoxy C1-3 alkyl, C13 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl, N,N-di-alkylamino C1-3 C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C1-2; 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 that 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 .

[0049] Preferably, R5 is cyano, C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-2 cyanoalkyl, C1-2 alkoxy, C1-2 hydroxyalkyl, C1-2 alkoxy C1-2 alkyl, C12 fluoroalkoxy C1-2 alkyl, C1-2 aminoalkyl, N-C1-2 alkylamino C1-2 alkyl, N,N-di-C1-2 alkylamino C1-2 alkyl, cyclopropyl or cyclopropylmethyl . More preferably, R5 is n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, C3-4 alkenyl, C3-4 alkynyl, cyanomethyl, cyanoethyl, methoxy, ethoxy, methoxymethyl , ethoxymethyl, methoxyethyl, aminomethyl, cyclopropyl or cyclopropylmethyl.

[0050] R6 represents cyano, fluorine, chlorine, amino, hydroxyl, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; and wherein when R5 comprises a substituted C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group.

[0051] It is understood that, when in aqueous media, the compounds of Formula (I) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (i.e., the compounds of Formula (I-Ia ) and Formula (I-IIa) as shown below, which can exist in tautomeric form as the compounds of formula (I-Ib) and formula (I-IIb)) in the CF3-oxadiazole motif. This dynamic balance may be important for the biological activity of compounds of Formula (I). The designations of A, R1, R2, R3, R4, R5 and R6 with reference to the compounds of Formula (I) of the present invention apply generally to the compounds of Formulas (II), (I-II), (I-Ia) and (I-IIa), as well as specific disclosures of combinations of A, R1, R2, R3, R4, R5 and R6, as represented in the compounds described in Table 1.1 (below) or the compound 1.1 described in Table T1 (below ).

[0052] The compounds of the present invention can be prepared as shown in the following schemes 1 to 13, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

[0053] Compounds of formula (I) can be obtained through coupling transformations with compounds of formula (II) and compounds of formula (III), where X is halogen, ester [including OMe or OEt)], anhydride [including OC(H)O or OAc], or OH, preferably halogen, in a suitable solvent (e.g., dimethylformamide, dichloromethane or tetrahydrofuran), preferably at temperatures between 25 °C and 100 °C, and optionally in the presence of a base (e.g., NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine), or under conditions described in the literature for a urea coupling. For examples, see WO 2003/028729, WO 2013/092943, WO 2017/055473, or WO 2014/025128.

[0054] Furthermore, compounds of formula (I) can be obtained through a coupling transformation with compounds of formula (II) and compounds of formula (III), where X is -OH, through processes that convert the -OH in an improved halide leaving group, such as a chloride, for example using triphosgene, diphosgene, 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.

[0055] Alternatively, compounds of formula (I) can be prepared from compounds of formula (II) by reactions with 1,1'-carbonyldiimidazole (CDI), triphosgene, diphosgene or phosgene in a suitable solvent (e.g. 1,2-dichloroethane, water, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable amino nucleophiles of formula (IV), in the presence of a suitable base such as pyridine, temperatures between 0 °C and 40°C. see WO 2017/055473. This reaction is shown in Scheme 2.

[0056] Additionally, compounds of formula (I) can be prepared from compounds of formula (V) via reactions with trifluoroacetic acid, trifluoroacetic ester (including methyl trifluoroacetic ester, ethyl trifluoroacetic ester), trifluoroacetic anhydride or trifluoroacetyl halide ( including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide) in the presence of a base (e.g., pyridine or 4-dimethylaminopyridine) in a suitable solvent, (e.g., ethyl acetate, tetrahydrofuran, 2 -methyl tetrahydrofuran or ethanol), at temperatures between 0 °C and 75 °C. For related examples, see documents WO 2003/028729, WO 2017/055473 and WO 2010/045251. This reaction is shown in Scheme 3.

[0057] Compounds of formula (V) can be prepared from compounds of formula (VI) via reactions with a hydroxylamine hydrochloride salt or a solution of hydroxylamine in water, in the presence of a base, such as triethylamine or carbonate of potassium, in a suitable solvent, such as methanol or ethanol, at temperatures between 0 °C and 80 °C. In some cases, better reaction performance may be gained with the use of a catalyst (e.g., 8-hydroxyquinoline). For related examples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268, WO 2017/055473 and WO 2013/066838. This reaction is shown in Scheme 4.

[0058] Compounds of formula (VI) are commercially available or can be prepared from compounds of formula (VII), where Y is formyl, Cl, Br, or I, via metal-promoted reactions with a cyanide reagent suitable, such as acetone cyanohydrin, dimethylmalononitrile, K4[Fe(CN)6], Zn(CN)2, NaCN, or CuCN, in a suitable solvent (e.g., dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 80 °C and 120 °C, and optionally in the presence of a metal catalyst (e.g. Pd or Ni) or a Grignard or organolithium reagent. For related examples, see Reeves, J. T. et al. J. Am. Chem. Soc., (2015), 137, 9481-9488, Ushijima, S., Togo, H. Synlett, (2010), 1067, US 2007/0155739, WO 2017/055473, and WO 2009/022746.

[0059] Alternatively, compounds of formula (VI) can be prepared from compounds of formula (VII), where Y is NH2, through radical nucleophilic aromatic substitution reactions in the presence of a nitrite source (e.g. , NaNO2 or iso-amyl nitrite), an acid (e.g., hydrochloric acid or HBF4) and a copper source (e.g., CuCN) in an acceptable solvent system, such as aqueous acetonitrile, at temperatures suitable between 0 °C and 100 °C. For related examples, see Wen, Q. et al. Tet. Lett. (2014), 55, 1271. This reaction is shown in Scheme 5. Scheme 5

[0060] Compounds of Formula (II) can be prepared from aldehyde compounds of Formula (IX), through condensation reactions with compounds of Formula (VIII), in a suitable solvent, (e.g., tetra- hydrofuran) at temperatures between 25°C and 75°C followed by the addition of a reducing agent, such as NaBH3CN, in a suitable solvent, (e.g. tetrahydrofuran or ethanol) at temperatures between 0°C and 25° W. For related examples, see Gazzola, C. and Kenyon, GL Journal of Labeled Compounds and Radiopharmaceuticals, (1978), 15, 181-4; 1978. This reaction is shown in Scheme 6.

[0061] Alternatively, compounds of Formula (II) can be prepared from compounds of formula (X), where X is Cl, Br, I, OH or OSO2Me, through substitution reactions with amines of Formula (VIII) in a suitable solvent (e.g. tetrahydrofuran) at temperatures 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 7.

[0062] Compounds of Formula (X) can be prepared from compounds of Formula (XI), where X is Cl or Br, through reactions 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 °C and 100 °C, optionally 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 8.

[0063] Compounds of formula (VII), where Y is formyl, NH2, Cl, Br, I, or CN, can be obtained through coupling transformations with compounds of formula (XII) and compounds of formula (III) , wherein hydrofuran, or 2-methyltetrahydrofuran), preferably at temperatures between 0 °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 a urea coupling.

[0064] Furthermore, compounds of formula (VII) can be obtained through coupling transformations with compounds of formula (XII) and compounds of formula (III), where X is OH, through processes that convert the - OH in an improved halide leaving group, such as a chloride, for example using triphosgene, diphosgene, phosgene, (COCl)2 or SOCl2, before treatment with the compounds of formula (XIII), optionally in the presence of a base (e.g. example, NaHCO3, Na2CO3, K2CO3, NaOH, triethylamine or N,N-diisopropylethylamine). The compounds of formula (III) are commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Journal Res (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 9.

[0065] Alternatively, compounds of formula (VII), where Y is formyl, Cl, Br, I, CN, can be prepared from compounds of formula (XII) through reactions with 1,1'-carbonyldi -imidazole (CDI), triphosgene, diphosgene or phosgene in a suitable solvent (e.g. 1,2-dichloroethane, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable nucleophiles of formula (IV) in the presence of a suitable base such as pyridine, K2CO3 or triethylamine, at temperatures between 0 °C and 40 °C. This reaction is shown in Scheme 10.

[0066] Compounds of formula (XII), where Y is formyl, NH2, Cl, Br, I or CN, can be prepared from compounds of formula (XIII), where X is Cl, Br, I or OSO2Me, through reactions with amines of formula (VIII), in the presence of a suitable base (e.g., triethylamine, pyridine, NaHCO3, Na2CO3, K2CO3 or NaH) in a suitable solvent, (e.g., dimethylformamide, N-methylpyrrolidine or acetonitrile) at temperatures between 0 °C and 100 °C. In some cases, improved 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 11.

[0067] Compounds of Formula (XIII), where Y is formyl, NH2, Cl, Br, I or CN and X is Cl or Br, are commercially available or can be prepared from compounds of Formula (XIV), through reactions with a halogen source (e.g., N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator, such as (PhCO2)2 or azobisisobutyronitrile (AIBN), optionally in the presence of light ultraviolet, 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. This reaction is shown in Scheme 12.

[0068] Alternatively, compounds of formula (XIII), where X is Cl, Br, I or OSO2Me and Y is formyl, NH2, Cl, Br, I or CN, are commercially available or can be prepared from compounds of formula (XIV), through reactions with an acid source (e.g., hydrochloric acid, hydrobromic acid, or hydroiodic acid), or a halogen source (e.g., tetrabromomethane, tetrachloromethane, or iodine) in the presence of triphenylphosphine, or with methanesulfonyl chloride (ClSO2Me), in a suitable solvent (e.g. dichloromethane), optionally in the presence of a base (e.g. triethylamine), 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 (XIV) are commercially available. This reaction is shown in Scheme 13.

[0069] 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.

[0070] Compounds of Formula (I) can be used in the agricultural sector and related areas of use, e.g., as active ingredients to control plant pests or in non-living materials to control spoilage-causing microorganisms or organisms potentially harmful to humans. The new compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants and by being safe from an environmental point of view. They have very useful curative, preventive and systemic properties and can be used for the protection of various cultivated plants. Compounds of Formula (I) can be used to inhibit or destroy pests occurring on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of different useful plant crops, while also protecting those parts of plants that grow later, e.g., from phytopathogenic microorganisms.

[0071] 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 site.

[0072] 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 has the ability to produce 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.

[0073] 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), impregnating the seeds in a liquid formulation or coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example, to the seedbed during sowing. The invention also relates to such methods of treating plant propagation material and the plant propagation material thus treated.

[0074] 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 technical products related to wood, in food storage, in hygiene management.

[0075] Additionally, the invention could be used to protect non-living materials from fungal attacks, e.g., construction wood, wall panels and paint.

[0076] The compounds of Formula (I) are, for example, effective against fungi and fungal disease vectors, as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease, as well as phytopathogenic bacteria and viruses are, for example:

[0077] 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.

[0078] The compounds of Formula (I) can be used for example in 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. .

[0079] 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, carrots, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines, for example grapes.

[0080] 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, e.g., HPPD inhibitors, ALS inhibitors, e.g., primisulfuron , prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional breeding or engineering methods genetics. 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®.

[0081] The term “useful plants” should be understood as also including useful plants that have been transformed in such a way by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, e.g. from toxin-producing bacteria, especially those of the Bacillus genus.

[0082] Examples of such plants are: YieldGard® (a variety of apple that expresses a CryIA(b) toxin); YieldGard Rootworm® (a variety of apple that expresses a CryIIIB(b1) toxin); YieldGard Plus® (a variety of maize that expresses a CryIA(b) toxin and a CryIIIB(b1) toxin); Starlink® (a variety of apple that expresses a Cry9(c) toxin); Herculex I® (a variety of maize that expresses a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety that expresses a CryIA(c) toxin); Bollgard I® (a cotton variety that expresses a CryIA(c) toxin); Bollgard II® (a cotton variety that expresses a CryIA(c) toxin and a CryIIA(b) toxin); VIPCOT® (a cotton variety that expresses a VIP toxin); NewLeaf® (a potato variety that expresses a CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

[0083] The term “crops” should be understood as also including crop plants that have been transformed in such a way by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, e.g. from toxin-producing bacteria, especially those of the Bacillus genus.

[0084] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2 , Vip3 or Vip3A; or insecticidal proteins 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 Streptomyces 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, maize 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.

[0085] Additionally, in the context of the present invention, they should be understood as δ-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1 , Vip2, Vip3 or Vip3A, 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 from 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).

[0086] 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.

[0087] The processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

[0088] 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).

[0089] Transgenic plants containing one or more genes that encode insecticide resistance and express one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (a variety of apple that expresses a CrylAb toxin); YieldGard Rootworm® (a variety of apple that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (a variety of apple 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 the Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac toxin and a Cry2Ab toxin); VipCot® (cotton variety that expresses the Vip3A toxin and a Cry1Ab); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0090] Additional examples of such transgenic crops are:

[0091] 1. Maís Bt11 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

[0092] 2. Maís Bt176 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

[0093] 3. Maís MIR604 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize that has been made resistant to insects through transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

[0094] 4. Maís MON 863 da 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.

[0095] 5. Cotton IPC 531 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.

[0096] 6. Maís 1507 of Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Maize genetically modified for expression of the Cry1F protein to achieve resistance to certain Lepidoptera insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

[0097] 7. Maís NK603 x MON 810 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. It consists of hybrid maize varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. The NK603 x MON 810 maize 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.

[0098] The compounds of Formula (I) (including any compound described in Table 1.1 or compound 1.1 described in Table T1 (below)) can be used in the control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) , in soybean plants.

[0099] In particular, transgenic soybean plants that express 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] of reference to Intact soybean 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).

[0100] Other transgenic soybean plants may comprise event SYHT0H2 - HPPD tolerance (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (U.S. Patent No. 7,632,985 and 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 (U.S. Patent Application Publication No. No. US 2010/0184079 and related applications and patents), event A2704-12 - tolerance to glufosinate (U.S. Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP-305423-1 - tolerance to ALS (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), event DAS-40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see 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 - tolerance to glyphosate, event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, event FG72 - tolerance to glyphosate and isoxaflutole, event BPS- CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.

[0101] The term "site", as used herein, designates the fields where plants are growing, or where seeds of cultivated plants are sown, or where the seed will be placed in the soil. Includes soil, seeds and seedlings, as well as established vegetation.

[0102] The term "plants" refers to all physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stalks, stems, foliage and fruits.

[0103] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants may be mentioned. Germinated plants and young plants that must be transplanted after germination or after emerging from the soil can also be mentioned. These young plants can be protected before transplanting by means of a full or partial immersion treatment. Preferably, "plant propagation material" is understood to denote seeds.

[0104] The compounds of Formula (I) can be used in an unmodified form or, preferably, in conjunction with the adjuvants conventionally used in the formulation technique. For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, 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 additional adjuvants such as stabilizers, defoamers, viscosity regulators, binders or stickiness promoters, as well as fertilizers, micronutrient donors or other formulations to obtain special effects.

[0105] 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, stickiness promoters, thickeners, binders or fertilizers. Such vehicles are described, for example, in WO 97/33890.

[0106] 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.

[0107] Wettable powders are in the form of finely divided particles that disperse quickly in water or other liquid vehicles. The particles contain the active ingredient trapped in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clays, silicas, and other organic or inorganic solids that are rapidly wetted. Wettable powders typically contain 5% to 95% of the active ingredient plus a small amount of wetting, dispersing, or emulsifying agent.

[0108] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid, and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or another liquid and 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.

[0109] Granular formulations include both extrudates and relatively coarse particles, and are typically applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clay, bentonite clays, montmorillonite clays, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, 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.

[0110] 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 vehicles.

[0111] Microcapsules are typically droplets or granules of the active ingredient surrounded by an inert porous capsule that allows the release of the contained material into the surrounding environment at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The 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 pearling or occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular coal. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0112] Other formulations useful for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprayers may also be used, in which the active ingredient is dispersed in a finely divided form as a result of vaporization of a low boiling point dispersant solvent vehicle.

[0113] Suitable agricultural adjuvants and vehicles 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.

[0114] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone , chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether diethylene glycol, 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, methoxy-propanol, methylisoamylketone, methylisobutylketone, methyl laurate, methyl octanoate, methyl oleate, chloride methylene, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monoethyl ether, p- xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and higher molecular weight alcohols such as alcohol amyl, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the vehicle of choice for diluting concentrates.

[0115] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, shells cottonseed, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

[0116] A wide variety of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with vehicle before application. These agents, when used, typically represent 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in nature and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surfactants include alkyl sulfate salts, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products such as nonylphenol ethoxylate-C.sub. 18; 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.

[0117] 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.

[0118] Furthermore, additionally, other biocidal active ingredients or compositions can be combined with the compositions of the invention, 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.

[0119] Reference is made here to pesticidal agents using their common name, known for example from “The Pesticide Manual”, 15th Edition, British Crop Protection Council 2009.

[0120] 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.

[0121] The compounds of Formula (I) are normally used in the form of agrochemical compositions, and can be applied to the crop or plant area to be treated, simultaneously or successively with additional compounds. These additional compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence plant growth. They 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 vehicles, surfactants or application-promoting adjuvants, usually used in the formulation technique.

[0122] 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.

[0123] 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 vehicle is for example a vehicle that is suitable for agricultural use. Agricultural vehicles 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).

[0124] 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.

[0125] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, arylphenylketone fungicides, benzamide fungicides, fungicides benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, copper fungicides, dithiolane, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, fungicides pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0126] Examples of suitable additional active ingredients also include the following: (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl)-3-difluoromethyl acid amide -1-methyl-1H-pyrazol-4-carboxylic acid, methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide 3-difluoromethyl-1-methyl-1H-pyrazol- 4-carboxylic, 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (107295771-1), (4 '-methylsulfanyl-biphenyl-2-yl)-amide of 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid, [2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl -ethyl]-amide of 1-methyl-3-difluoromethyl-4H-pyrazol-4-carboxylic acid, (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-tolylimidazol-1-sulfonamide, N-allyl-4,5-dimethyl-2- trimethylsilylthiophene-3-carboxamide, N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide, N-(2-methoxy-5-pyridyl)-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] Methyl 3-methoxyacrylate, (E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methylmethoxyacrylate, (E)-2-[2-[6- Methyl (2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3- methyl methoxyacrylate, (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methylmethoxyacrylate, (E)-2-[2-[3-(5-methylpyrimidin Methyl -2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3- (phenylsulfonyloxy)phenoxy]phenyl-3-methyl methoxyacrylate, (E)-2- Methyl [2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-methylphenoxyphenyl]-3-methoxyacrylate, (E)-2-[2-( Methyl 3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methylmethoxyacrylate, (E)-2[ methyl 2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, (E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-methyl 3-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-methylmethoxyacrylate, (E)-2-[2-(3 -n-propyloxy-phenoxy)phenyl]3- methyl methoxyacrylate, (E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methyl methoxyacrylate, (E)- 2-[2-[3- Methyl (2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methylmethoxyacrylate, (E)-2-[2-(4 -tert-butyl-pyridin-2-yloxy)phenyl]-3-methyl methoxyacrylate, (E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methylmethoxyacrylate, (E )- Methyl 2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4 - methyl yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-methyl 3-methoxyacrylate, (E)-2-[2- (Methyl 3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy] methyl phenyl]-3-methoxyacrylate, (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloxyminomethyl)phenyl]-methyl 3-methoxyacrylate, (E)- 2-{2 -[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methyl methoxyacrylate, (E),(E)-2-{2-(3-methoxyphenyl)methyloxyminomethyl] -phenyl}-3-methyl methoxyacrylate, (E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methyl methoxyacrylate, (E),(E) Methyl -2-{2-[6-phenylpyrimidin-4-yl)-methyloxyminomethyl]phenyl}-3-methoxyacrylate, (E),(E)-2-{2-[(4-chlorophenyl)-methyloxyminomethyl]- methyl phenyl}-3-methoxyacrylate, (E)- 2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methyl methoxyacrylate, (E),(E)-2-{2-[(3-nitrophenyl)methyloxyminomethyl]phenyl}-3-methyl methoxyacrylate, 3-chloro-7-(2-aza-2,7,7-trimethyl-oct -3-en-5-yne), 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3- ethylcarbamate bromo-2,3-diiodo-2-propenyl, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-n-butylcarbamate iodo-2-propynyl, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenylcarbamate; phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4- chlorophenol, 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1, 3,5-thidiazine-2-thione, N-(2-p-chlorobenzoylethyl)-hexaminochloride, acibenzolar, acipetacs, alanicarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradine, amisulbrom, amobam, ampropylphos, anilazine, asomate, aureofungin, azaconazole, azafendine, azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentalurone, bentiavalicarb, bentiazole, benzalkonium chloride, benzamacryl, benzamorph, benzohydroxamic acid, benzovindiflupyr, berberine , betoxazine, biloxazole, binapacryl, biphenyl, bitertanol, bitionol, bixaphene, blasticidin-S, boscalid, bromothalonil, bromuconazole, bupyrimate, butiobate, butylamine calcium polysulfide, Captafol, Captan, carbamorph, carbendazim, carbendazim hydrochloride, carboxine, carpropamide , carvone, CGA41396, CGA41397, quinomethionate, chitosan, clobenthiazone, chloraniformetan, chloranil, chlorphenazole, chloroneb, chloropicrin, chlorothalonil, chlorozolinate, clozolinate, climbazole, clotrimazole, clozilacone, copper-containing compounds such as copper acetate, copper carbonate, copper 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, dazomete, debacarb, decafentin, dehydroacetic acid, di-2-pyridyl disulfide 1,1'-dioxide, diclofluanid, diclomezine, diclone, dichlorane, dichlorophene , diclozolin, diclobutrazol, diclocimet, diethofencarb, difenoconazole, difenzoquat, diflumetrim, O,O-diiso-propyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimethconazole, dimethomorph, dimetirimol, diniconazole, diniconazole-M, dinobutone, dinocap , dinoctone, dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrithione, disulfiram, dictatorylimphos, dithianone, dithioether, dodecyldimethyl ammonium chloride, dodemorph, dodicine, dodine, doguadine, drazoxolone, edifenphos, enestroburin, epoxiconazole, etaconazole, etem, etaboxam, ethyrimole , ethoxyquin, ethylicin, (Z)-N-benzyl-N([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, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole , flusulfamide, flutanil, flutolanil, flutriafol, fluxapiroxad, folpet, formaldehyde, fosetyl, fuberidazole, furalaxyl, furamethpir, furcarbanil, furconazole, furfural, furmeciclox, furophanate, gliodine, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hex iltiophos , hydrargafen, hydroxyisoxazole, himexazol, imazalyl, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanylbutyl carbamate, isoprothiolane, isopyrazam, isotian ila, isovaledione, isopamphos , kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamide, maneb, mebenil, mecarbinzide, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, meptildinocap, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole , metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxidine, myclobutanil, myclozolin, nabam, natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene, nitrotal -isopropyl, nuarimol, octilinone, ofurace, organomercury compounds, orisastrobin, ostol, oxadixyl, oxasulfuron, oxathiapiproline, oxina-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencicurone, penflufen, pentachlorophenol, penthiopyrad, fenamacryl, phenazine oxide, phosdiphene, fosetyl-Al, phosphorous acids, phthalide, picoxystrobin, piperaline, polycarbamate, polyoxin D, polyoxrim, poliram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazide, prothiocarb, prothioconazole , pidiflumetofen, pyracarbolide, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazofos, piribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyriophenone, pyroquilone, pyroxychlor, pyroxifur, pyrrolnitrin, quaternary ammonium compounds, quinacetol, quinazamide, quinconazole, quinomethionate, quinoxifene, quintazene , rabenzazole, santonin, sedaxane, siltiofam, simeconazole, sipconazole, sodium pentachlorophenate, solatenol, spiroxamine, streptomycin, sulfur, sultropene, tebuconazole, tebfloquine, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, tiadifluor, ticiophene, thifluzamide, 2-(thiocianomethylthio)benzothiazole , thiophanate-methyl, thioquinox, thiram, tiadinil, timibenconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimephone, triadimenol, triamifos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazol, triporin, triflumizole, triticonazole, uniconazole, urbacide , validamycin, valifenalate, vapam, vinclozolin, zarilamide, zineb, ziram and zoxamide.

[0127] 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.

[0128] 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 .

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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:

[0133] Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chloropyrifos, chlorophenvinphos, 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, malathion, metakryphos, metamide ofos, methidathione, methyl -parathion, mevinphos, monocrotophos, nalede, omethoate, oxidemethone-methyl, paraoxone, parathion, parathion-methyl, phentoate, phosalone, phospholane, phosphocarb, phosmet, phosfamidone, phorate, phoxime, pirimiphos, pirimiphos-methyl, profenophos, propaphos, proetanphos , prothiophos, pyraclophos, pyridapenthion, quinalphos, sulprophos, temephos, terbufós, tebupirinphos, tetrachlorvinphos, thytone, triazophos, trichlorphone, vamidothione.

[0134] 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.

[0135] Pyrethroids: acrinatin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl) 5-benzyl-3-furylmethyl cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioalethrin, bioalethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI- 85193, cycloprothrin, cyhalothrin, cytithrin, cyfenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t- fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

[0136] Arthropod growth regulators: a) inhibitors of chitin synthesis: benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, triflumurone, buprofezin, diophenolan, hexithiazox, etoxazole, chlorophentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0137] Other antiparasitics: acequinocil, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus turingiensis, bensultape, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, campeflor, cartape, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide , clotianidine, ciromazine, diaclodene, diafentiurona, dbi-3204, dynamic, di-hidroximethyldi-hydroxypirolidine, dinobutone, dinocape, endsulphane, etiprol, etofenprox, phenazaquine, mti-800, phenpyiroximate, flubricirime, flubenzymine BROCITRATE, FLUFENZINE, FLUFENPROX , fluproxifen, halofenprox, hydramethylnone, IKI-220, kanemite, NC-196, Neemgard, nidinorterfuran, nitanpyram, SD-35651, WL- 108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridabene, pyrimidifeme, NC-1111, R-195 ,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifone, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin , verbutin, vertalec, YI-5301.

[0138] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0139] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0140] 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 .

[0141] The following mixtures of 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 Table 1.1 or Table T1 (compound 1.1) (below):

[0142] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,

[0143] an acaricide selected from the group of substances consisting of 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC name) Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenylsulfone (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, oxide arsenious (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, azocyclotine (46) + TX, nitrogenate (889) + TX, benomyl (62) + TX, benoxaphos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (name IUPAC) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclene (918) + TX, bromophos (920) + TX , bromophos-ethyl (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxime (103) + TX, butoxycarboxime (104) + TX, butylpyridabene (alternative name) + TX, calcium polysulfide ( IUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (code development) (125) + TX, quinomethionate (126) + TX, chlorobenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorofenapyr (130) + TX, chlorophenetol (968) + TX, chlorophensone (970) + TX, chlorofensulfite (971) + TX, chlorfenvinphos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiurone (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, clofentezine ( 158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamitone (alternative name) [CCN] + TX, crotoxiphos (1010) + TX, kofraneb (1013) + TX, cyanhoate ( 1020) + TX, cyflumetofen (No. CAS Reg.: 400882-07-7) + TX, cyhalothrin (196) + TX, ciexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefion ( 1037) + TX, demefion-O (1037) + TX, demefion-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, ethrimphos (1142) + TX, fenazaflor (1147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX , phenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, phensone (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX , fipronil (354) + TX, fluacripirime (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, flueethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formetanate (405) + TX, hydrochloride formetanate (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- (methoxyaminothiophosphoryl )isopropyl salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenfos (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, mevinphos (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, complex of nitrilacarb 1:1 with 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, fencaptone (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, propetamphos (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, quinalphos (711) + TX, quinthiophos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 ( development code) (1383) + TX, rotenone (722) + TX, scradane (1389) + TX, sebuphos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code ) + 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, tebufenpyrad (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, trichlorphone (824) + TX, tripenophos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothione (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,

[0144] an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutrin [CCN] + TX, diclone ( 1052) + TX, dichlorophene (232) + TX, endotal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide ( 1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX,

[0145] an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, benzoate emamectin (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,

[0146] an avicid 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,

[0147] 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, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinolinesulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766 ) + TX, and thiomersal (alternative name) [CCN] + TX,

[0148] 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, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742 ) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, bacillus subtilis var. amyloliquefaciens strain FZB24 (commercialized by Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, U.S.A. and known by the trade name Taegro®) + TX,

[0149] a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,

[0150] a chemosterilant selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzurone (250) + TX, dimatife ( alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl afolate [CCN] + TX, morzide [CCN] + TX, penflurone (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

[0151] an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) ( 222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methyl-hept-2-en-4-ol (IUPAC name ) (541) + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1- acetate yl (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-in-1-yl acetate (IUPAC name) (438) + TX, (Z)-icos-13-en-10-one (IUPAC name ) (448) + TX, (Z)-tetradec-7-en-1- al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name ) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12- acetate dien-1-yl (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name ) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemon (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en- acetate 1-yl (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, 4 -ethyl methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421 ) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, Methyleugenol (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 (name IUPAC) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine ( alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) ) [CCN] + TX,

[0152] 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, adipate dibutyl (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] +TX,

[0153] an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl )ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (name IUPAC/Chemical Abstracts) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyldiethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindan- 1,3-dione (IUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) ( 1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazole dimethylcarbamate -5-yl (IUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl dimethylcarbamate -3-oxocyclohex-1-enyl (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethione (alternative name) [CCN] + TX, acetoprol [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin ( 864) + TX, allethrin (17) + TX, alosamidine (alternative name) [CCN] + TX, alixicarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidithione (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidathione (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, nitrogenate (889) + TX, delta endotoxins from Bacillus thuringiensis (alternative name) (52) + TX, hexafluorosilicate barium (alternative name) [CCN] + TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioalethrin (78) + TX, S-cyclopentenyl 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, bromophos-ethyl (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, arsenate calcium [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, campefchlor (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, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazurone (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorphoxime (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX , chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, kinerins (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, oleate copper [CCN] + TX, coumaphos (174) + TX, coumitoate (1006) + TX, crotamitone (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (name alternative) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cyclothrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, 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, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demethone (1038) + TX, demethion-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-methylpyrazole phosphate -3-yl (IUPAC name) (1076) + TX, diflubenzurone (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimethylane (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093 ) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diofenolan (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 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endothione (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonan (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, 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, etrymphos (1142) + TX, EXD (1143) + TX, fanfur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, fenchlorphos (1148) + TX, fenetacarb (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX, fenoxycarb (340) + TX, fenpyritrine (1155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, phenthion (346) + TX, phenthion-ethyl [CCN] + TX, fenvalerate (349 ) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendiamide (No. of Reg. CAS: 272451-65-7) + TX, flucofurone (1168) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, fluemethyl (1169) + TX, flufenerime [CCN] + TX, flufenoxurone (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, phonofos (1191) + TX, formetanate (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, O Isopropyl -(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathione (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmoline I (696) + TX, jasmolina II (696) + TX, jodfenfos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, quelevane (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lyrimphos (1251) + TX, lufenurone (490) + TX, 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, mecarfone (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, methamidodium (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, metochin-butyl (1276) + TX, methotrin (alternative name) (533) + TX, methoxychlor ( 534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methyl-chloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, methoxadiazone (1288) + TX, mevinfos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothione (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, naled (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, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1 :1 with 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-4-methyl-2-oxo-2H-chromen-7 phosphorothioate -yl O,O- diethyl (IUPAC name) (1074) + TX, O-6-methyl-2-propylpyrimidin-4-yl O,O-diethyl phosphorothioate (IUPAC name) (1075) + TX, O dithiopyrophosphate ,O,O',O'-tetrapropyl (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, petroleum oils (alternative name) ( 628) + TX, PH 60-38 (development code) (1328) + TX, fencaptone (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, fosalone ( 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, polychlorodicyclopentadiene isomers (IUPAC name) ( 1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precone I (alternative name) [CCN] + TX, precono II (alternative name) [CCN] + TX, precono III (alternative name) [CCN] + TX, primidone (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacil ( 1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidathion (1360) + TX, prothiophos (686) + TX, protoate (1362 ) + TX, protrifenbut [CCN] + TX, pymetrozine (688) + TX, pyraclophos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II ( 696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridalyl (700) + TX, pyridafenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708 ) + TX, quassia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfos-methyl (1376) + TX, quinothione (1380) + TX, quintiophos (1381) + TX, R-1492 (code development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 ( development code) (1386) + TX, riânia (alternative name) (1387) + TX, ryanodina (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradano (1389) + TX, sebuphos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX , sodium fluoride (IUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, thiocyanate sodium [CCN] + TX, sofamide (1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramate (CCN) + TX, sulcofurone (746) + TX, sulcofurone-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, tebufenpyrad (763) + TX, tebupyrimphos (764) + TX, teflubenzurone (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbame (alternative name) + TX, terbufós (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 hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800) + TX, thiometone (801) + TX, thionazine (1434) + TX , thiosultape (803) + TX, thiosultape- sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin [ CCN] + TX, trichloronate (1452) + TX, tripenophos (1455) + TX, triflumurone (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidothione (847) + TX, vaniliprole [CCN ] + TX, veratridine (alternative name) (725) + TX, veratrin (alternative name) (725) + TX, 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,

[0154] a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloretocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530 ) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730 -71-3] + TX,

[0155] a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5- acid methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN ] + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusaphos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX , cloetocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidaphos (1044) + TX, diclofenthion (1051 ) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name ) [CCN] + TX, etoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothione (1158) + TX, fosthiazate (408) + TX, fosthiethane (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metame-potassium (alternative name) (519) + TX, metame-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN ] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636 ) + TX, 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/Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,

[0156] a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,

[0157] 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 ,

[0158] 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, arsenous 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, coumatetralyl (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, 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,

[0159] a synergistic agent selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3 -hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) development) (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,

[0160] an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinone ( 227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridine-4-amine (IUPAC name) (23 ) + TX, thiram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

[0161] a virucide selected from the group of substances consisting of imannin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,

[0162] a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) and thiophanate-methyl (802) + TX,

[0163] and biologically active compounds selected from the group consisting of ametoctradine [865318-97-4] + TX, amisulbrome [348635-87-0] + TX, azaconazole [60207-310] + TX, benzovindiflupyr [1072957-71 -1] + TX, bitertanol [70585-36-3] + TX, bixafen [581809-46-3] + TX, bromuconazole [116255-48-2] + TX, coumoxystrobin [850881-70-8] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [23841011-2] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674 -21-0] + TX, fluxapyroxad [90720431-3] + TX, fluopyram [658066-35-4] + TX, phenaminstrobin [366815-39-6] + TX, isofetamide [875915-78-9] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08- 1] + TX, isothianil [224049-04-1] + TX, mandestrobin [173662-97-0] (can be prepared, according to the procedures described in the document 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 [101903-30-4] + TX , penflufen [494793-678] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pirifenox [88283-41-4] + TX, prochloraz [6774709-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimephone [43121- 43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-890] + TX, triticonazole [131983-72-7] + TX, ancymidol [1277168-5] + TX, fenarimol [60168 -88-9] + TX, nuarimol [63284-719] + TX, bupyrimate [41483-43-6] + TX, dimethyrimole [5221-534] + TX, ethyrimole [23947-60-6] + TX, dodemorph [ 1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564- 91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX, mepanipyrim [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [13134186 -1] + TX, fluoralaxyl [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 [50471-44 -8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-407] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860 -33-8] + TX, dimoxystrobin [149961-52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxime-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orisastrobin [248593-16-0] + TX, picoxystrobin [117428-225] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin [862588-11 -2] + TX, ferbame [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [900642-2] + TX, propineb [ 12071-83-9] + TX, tirame [137-26-8] + TX, zinebe [12122-67-7] + TX, ziram [137-30-4] + TX, capitafol [2425-06-1] + TX, capitan [133-06-2] + TX, diclofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanide [731 -27-1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-391] + TX, mancobre [53988-93-5] + TX, oxina-copper [10380-286] + 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 [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-007] + TX, quinomethionate [2439-01-2] + TX, chloroneb [267577-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, diclone [117-80-6] + TX, diclocimet [139920 -32-4] + TX, diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (Flumorphe) [211867-47-9] + TX, dithianone [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX , famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64 -7] + TX, fluaziname [79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamide [126833-17-8] + TX, fosetyl-aluminum [39148-24-8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Ciazofamide) [120116-88-3] + TX , kasugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-036] + TX, pencicurone [66063-05-6] + TX, phthalide [27355-222] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [1111380-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12- 4] + TX, pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyroquilone [57369-32-1] + TX, 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 extract containing tea 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 [41814-78-2] + TX, triporin [26644-46-2] + TX, validamycin [37248 -47-8] + TX, valifenalate [283159-90-0] + TX, zoxamide (RH7281) [15605268-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, fenamacryl + TX, sedaxane [874967-676] + TX, trinexapac-ethyl [95266-40-3] + TX, (9-dichloromethylene-1,2,3,4-tetrahydro-1,4- 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid methane-naphthalen-5-yl)-amide (disclosed in WO 2007/048556) + TX, (3',4',5'-trifluoro- 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX, [(3S,4R,4aR,6S,6aS,12R, 12aS,12bS)-3- [(cyclopropylcarbonyl)oxy]- 1,3,4,4a,5,6,6a,12,12a,12b- decahydro-6,12-dihydroxy-4,6a, 12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]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-pyrazol-4-carboxamide [926914-55-8] + TX,

[0164] or a biologically active compound selected from the group consisting of N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl- pyrazol-4-carboxamide + TX (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5 ,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (can be prepared according to the procedures described in WO 2011/138281) + TX, 6-ethyl-5,7-dioxo -pyrrolo[4,5][1,4]dit-ino[1,2-c]isothiazol-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro -6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedures described in WO 2012/031061) + TX, 3-(difluoromethyl)-N-(7-fluoro -1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazol 1,1-dioxide (can be prepared according to the procedures described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3 ,3-dimethylisoquinolin-1-yl)quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3- quinolyl)oxy]phenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl )oxy]-6-fluorophenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, oxathiapiproline [1003318-67-9] + TX, N-[6- tert-butyl [[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3 -(trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3 -trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, N-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl 2,2,2-trifluoroethyl ]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy)- α,α,α-trifluoro-o-tolyl]-1-(1H-1, 2,4-triazol-1-yl)propan-2-ol + TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl- 1-(1H-1,2,4-triazol-1-yl)butan-2-ol + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan- 4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2 ,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl ]- N-ethyl-N-methyl-formamidine (can be prepared according to the procedures described in WO 2007/031513) + TX, [2-[3- [2-[1-[2-[3,5- bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chlorophenyl] methanesulfonate (can be prepared as with the procedures described in WO 2012/025557) + TX, but-3-ynyl N-[6-[[(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 (can be prepared according to the procedures described in WO 2010/146031) + TX, N-[[5-[4-(2,4-dimethylphenyl )methyltriazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121104) + TX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2 -ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (can be prepared according to with 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 from 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-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, (4-phenoxyphenyl)methyl 2-Amino-6-methyl-pyridine-3-carboxylate + TX , N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazol-4-carboxamide [1255734-28-1] (can be prepared according to procedures described in WO 2010/130767) + TX, 3-(difluoromethyl)-N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1- methylpyrazole-4-carboxamide [1352994-67-2] + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4- (4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl )-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl -formamidin + 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.

[0165] References in parentheses after active ingredients, e.g., [3878-19-1] refer to the Chemical Abstracts Registration Number. The mixing partners described above are known. When active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], are described there with the entry number given in curly brackets here 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 can be accessed 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.

[0166] Most of the active ingredients described above are previously referred to by a so-called “common name”, with the relevant “ISO common name” or another “common name” 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 neither of these designations nor a “common name” is used, an “alternative name” is used. "CAS Reg. No." means the Chemical Abstracts Registry Number.

[0167] The mixture of active ingredients of compounds of Formula (I) selected from compound 1.1 described in Table T1 (below) or a compound of Formula (I) described in Table 1.1 (below), and an active ingredient as described above , are preferably in a mixing ratio of 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of 20:1 to 1:20, even more especially from 10:1 to 1 :10, most especially from 5:1 to 1:5, with special preference being given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 being likewise preferred above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3 :2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2 :3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4 :75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing proportions are by weight.

[0168] 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 the pests or their environment, with the exception of a method for treating the human or animal body by surgery or therapy and from diagnostic methods practiced on the human or animal body.

[0169] Mixtures comprising a compound 1.1 described in Table T1 or a compound of Formula (I) described in Table 1.1 (below) and one or more active ingredients as described above can be applied, for example, in a simple “mixture” form. -ready”, in a combined spray mixture prepared from separate formulations of the components of the single active ingredients, such as a “tank mix”, and in a combined use of the individual active ingredients when applied in a sequential manner, i.e., one after the other over a relatively short period of time, 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 (below) or Table T1 (below), and the active ingredient(s) as described above, is not essential for carrying out the present invention.

[0170] The compositions according to the invention may also comprise additional solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example coconut oil, rapeseed oil or epoxidized soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders and/or adhesives, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

[0171] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary, e.g. by intimate mixing and/or grinding of the active ingredient with the auxiliary (auxiliary). 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.

[0172] 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 , a 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 material by insects or by phytopathogenic microorganisms, preferably fungal organisms.

[0173] A further aspect of the invention relates to a method for controlling or preventing an infestation of plants, for example, useful plants, such as crop plants, propagation material thereof, for example, seeds, harvested crops, by example, harvested food crops, or non-living materials by insects or phytopathogenic microorganisms or spoilage or organisms potentially harmful to humans, especially fungal organisms, which comprises the application of a compound of formula (I) or a preferred individual compound as defined above as an active ingredient to plants, parts of plants or their location, their propagating material or any part of non-living materials.

[0174] Means of control or prevention that reduce infestation by microorganisms or phytopathogenic or deteriorating organisms potentially harmful to humans, especially fungal organisms, to the point where an improvement is demonstrated.

[0175] A preferred method for controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which comprises the application of a compound of formula (I), or an agrochemical composition containing at least one of the aforementioned compounds is foliar application. The frequency of application and the application rate will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of Formula (I) can also penetrate the plant through the roots through the soil (systemic action) by drenching the plant site 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.

[0176] 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 intimate mixing and/or grinding the compound with diluents, for example, solvents, solid carriers and, optionally, surfactant compounds (surfactants).

[0177] 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 are 10 mg to 1 g of active substance per kg of seeds.

[0178] 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 enough.

[0179] 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.

[0180] The compositions of the invention can be employed in any conventional form, for example in the form of a double package, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a concentrate suitable for flow for seed treatment (FS), a solution for seed treatment (LS), a water-dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), a emulsion, water-in-oil (EO), an emulsion, oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL) , a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any formulation technically possible in combination with agriculturally acceptable adjuvants.

[0181] Such compositions can 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, adhesives, thickening agents 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), wettable powders and granules, may contain surfactants such as wetting agents and dispersants and other compounds that provide adjuvant effects, for example, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, a lignin sulfonate, a fatty alkyl sulfate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[0182] A seed treatment formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in form of a suitable seed treatment formulation, for example, as an aqueous suspension or in a powder form. dry, having good adhesion to the seeds. Such seed treatment formulations are known in the art. Seed treatment formulations may contain individual active ingredients or combinations of active ingredients in encapsulated form, e.g., as slow-release capsules or microcapsules.

[0183] In general, formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of agriculturally acceptable surfactant and 10 to 99.99% of solid or liquid formulation inert agents and adjuvant(s). ), the active agent consisting 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 contain, for example, 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.

[0184] Although it is preferred to formulate commercial products as concentrates, the end user will typically use diluted formulations. Table 1.1: This table discloses 10 specific compounds of formula (T-1): wherein A is 1,4-phenylene, R1 and R2 and R3 are hydrogen and NR4(R5) is as defined below in Table 1.

[0185] Table 1.1 provides 10 individual compounds of formula (T-1) where A, R1, R2, and R3 are as specifically defined and refers to Table 1 where - NR4(R5) is specifically defined. Table 1

EXAMPLES

[0186] 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. ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8 ppm.

[0187] Throughout this description, temperatures are presented in degrees Celsius (°C) and "p.f." means melting point. LC/MS stands for Liquid Chromatography and Mass Spectroscopy, and the description of the apparatus and method (Method A) is as follows:

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

[0188] Waters SQ 2 Detector

[0189] Ionization method: Electrospray

[0190] Polarity: positive and negative ions

[0191] Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Gas Flow in the Cone (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650

[0192] Mass range: 100 to 900 Da

[0193] DAD wavelength range (nm): 210 to 500

[0194] Waters ACQUITY UPLC Method with the following HPLC gradient conditions:

[0195] (Solvent A: Water/Methanol 20:1 + 0.05% formic acid and Solvent B: Acetonitrile + 0.05% formic acid)

[0196] Column type: Waters UPLC ACQUITY HSS T3 Column length: 30 mm; Column internal diameter 2.1 mm; Particle Size: 1.8 microns; Temperature: 60°C

[0197] Where necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate, by means of standard physical separation techniques such as chiral reversed-phase chromatography, or by stereoselective synthetic techniques, e.g., using chiral starting materials. Formulation Examples

[0198] The active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a suitable mill, generating wettable powders that can be diluted with water to give rise to suspensions of the desired concentration.

[0199] 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.

[0200] Emulsions of any required dilution, which can be used to protect plants, can be obtained from this concentrate by dilution with water.

[0201] Ready-to-use powders are obtained by mixing the active ingredient with the vehicle and grinding the mixture in a suitable mill. Such powders can also be used for dry seed disinfections.

[0202] 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.

[0203] The finely crushed active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. Dust-free coated granules are thus obtained.

[0204] 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 such dilutions, live plants as well as plant propagation material can be treated and protected from infestation by microorganisms by spraying, pouring or immersing.

[0205] 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 such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms by spraying, pouring or immersing.

Suspension of slow-release capsules

[0206] 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 is added a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete.

[0207] The capsule suspension obtained is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% active ingredients. The average diameter of the capsules is 8-15 microns.

[0208] 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 1,1'-diimidazole DCE = 1,2-dichloroethane DCM = dichloromethane DIPEA = N,N -diisopropylethylamine DMA = dimethylacetamide DMF = dimethylformamide EtOAc = ethyl acetate EtOH = ethyl alcohol HCl = hydrochloric acid m.p. = melting point MeOH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide TFAA = trifluoroacetic acid anhydride THF = tetrahydrofuran

Preparative Examples

[0209] The compounds of formula (I) can be prepared accordingly using the synthetic techniques described both above and below.

[0210] Example 1: This example illustrates the preparation of 2-(difluoromethoxy)-N-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ]acetamide (Compound 1.1 of Table T1) Step 1: Preparation of N'-hydroxy-4-methyl-benzamidine

[0211] To a suspension of 4-methylbenzonitrile (35 g, 0.29 mol) in ethanol (220 mL) and water (440 mL) was added, at room temperature, hydroxylamine hydrochloride (41.1 g, 0.58 mol), potassium carbonate (65.4 g, 0.47 mol) and 8-hydroxyquinoline (0.22 g, 1.5 mmol). The reaction mixture was heated at 80°C for 4 hours. The mixture was then 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 compound of the title. 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

[0212] 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.

[0213] 1H NMR (400 MHz, CDCl3) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

[0214] 19F NMR (400 MHz, CDCl3) δ ppm: -65.41 (s). Step 3a: Preparation of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

[0215] 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. m.p.: 58-63°C.

[0216] 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

[0217] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s).

[0218] 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole was isolated as a byproduct as a white solid. m.p.: 61-66 °C.

[0219] 1H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

[0220] 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

[0221] 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) was added diethylphosphite (4, 7 mL, 35.7 mmol) at 5 °C. The mixture was stirred at 5-10°C for two hours, 1M HCl was added and the volatiles were removed under reduced pressure. The resulting white paste was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (cyclohexane:EtOAc eluent gradient 99:1 to 9:1) to give 7.10 g of the title compound as a white solid. m.p.: 58-63°C.

[0222] 1H NMR (400 MHz, CDCl3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

[0223] 19F NMR (400 MHz, CDCl3) δ ppm: -65.32 (s). Step 4: Preparation of [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine hydrochloride

[0224] A dry flask was charged with sodium hydride (2 equiv., 3.13 mmol, 60% by mass NaH) and tetrahydrofuran (25 mL). To this white suspension was added tert-butyl N-tert-butoxycarbonylcarbamate (1.1 equiv, 1.72 mmol) and, while stirring for 5 minutes, gas evolution was observed. 3-[4-(Bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.500 g, 1.56 mmol) was then introduced and the contents were stirred for 12 hours. After completion of the reaction, the solution was poured into water and extracted with ethyl acetate (2x30 mL). The organic layers were combined and dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a pale yellow oil which partially crystallized upon standing. The yellow material was dissolved in dioxane (5 mL) and a hydrogen chloride solution (15 equiv., 24.7 mmol, 4 M in dioxane) was introduced dropwise. After stirring overnight at 25 °C, the reaction solution was diluted with ether and provided a white precipitate (70% yield) whose analysis corresponded to the reported values and which was used without further purification. m.p.: >200°C, LC/MS (Method A) retention time = 0.61 minutes, 244 (M+H).

[0225] 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.56 (s l, 2H), 8.13 (d, 2H), 7.75 (d, 2H), 4.15 (s, 2H ).

[0226] 19F NMR (400 MHz, DMSO-d6) δ ppm: -64.69 (s).

[0227] Alternatively, the title compound can be prepared using an analogous procedure as described in WO 2013/066839.

[0228] 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). Precipitation of a white solid and 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 5: Preparation of 1-cyclopropyl-1-(2,2-difluoroethyl)- 3-[[4—[5—(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

[0229] [4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine hydrochloride (100 mg) was dissolved in dichloromethane (1.07 mL) and N,N-dimethylformamide (0.35 mL). CDI (90 mg) was added to this suspension in one portion at room temperature. The suspension slowly turned into a clear solution. The mixture was stirred for 4 hours at room temperature. N-(2,2-difluoroethyl)cyclopropanamine hydrochloride (169 mg) was then added to the reaction mixture at room temperature, followed by N,N-diethylethanamine (0.15 mL). The mixture was stirred for 48 hours at room temperature. Water and ethyl acetate were then 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 evaporated. The crude residue was purified by silica gel chromatography using a cyclohexane/ethyl acetate gradient to give the title compound (134 mg, 96% yield) as a colorless oil.

[0230] 1H NMR (400 MHz, CDCl3) δ ppm: 8.12 (d, 2H), 7.47 (d, 2H), 6.03 (tt, 1H), 5.81 (t, broad, 1H ), 4.58 (d, 2H), 3.70 (dt, 2H), 2.67 (m, 1H), 0.93 (m, 2H), 0.83 (m, 2H).

[0231] 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 protocol were analyzed using LC/MS Method B.

[0232] By way of example, the acid derivatives of formula (III) (0.0375 mmol in 375 µL of DMA) were transferred to a deep well plate with 96 slots (DWP96) containing the derivatives of [[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.

[0233] 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 protocol were analyzed using LC/MS Method B.

[0234] 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 DMA. The reaction mixtures were stirred at room temperature for 30 minutes and then [[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine derivatives of formula (II) were added (0.05 mmol) 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 impure 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%.

[0235] Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate, by means of standard physical separation techniques such as chiral reversed-phase chromatography, or by stereoselective synthetic techniques, (e.g., using chiral starting materials). Table T1: Melting point (pf) and/or retention times (RT) data for compounds according to Formula (I):

BIOLOGICAL EXAMPLES: General examples of leaf disc tests in well plates:

[0236] Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. The cut leaf discs or segments are placed in multiwell plates (24-well format) on agar prepared with water. 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:

[0237] Fragments of mycelia or suspensions of conidia of a fungus, freshly prepared from liquid cultures of the fungus or from cryogenic storage, are directly mixed in nutrient broth. DMSO solutions of the test compound (max. 10 mg/mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 μl of this solution is pipetted into a microtiter plate (96-well format). 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 / preventive on leaf discs (Brown Rust)

[0238] 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 (r.h.) under a light regime of 12 hours light/12 hours dark in a climate-controlled cabinet, and the activity of a compound was evaluated as a 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).

[0239] 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.

[0240] Compounds (from Table T1) 1.1

[0241] Example 2: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / dressing on leaf discs (Brown Rust)

[0242] 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 cabin, 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).

[0243] Compounds following 200 ppm in the applied formulation give disease control of at least 80% in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development.

[0244] Compounds (from Table T1) 1.1

[0245] Example 3: Fungicidal activity against Phakopsora pachyrhizi / soybean / preventive on leaf discs (Asian soybean rust)

[0246] Soybean leaf discs are placed on water agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, leaf discs are inoculated by spraying a spore suspension onto the lower leaf surface. After an incubation period of 24-36 hours in a climate-controlled chamber, in the dark at 20°C and r.u. of 75%, the leaf discs are kept at 20 °C with 12 h of light/day and r.h. of 75%. The activity of a compound is evaluated as percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated check leaf discs (12 to 14 days after application).

[0247] 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.

[0248] Compounds (from Table T1) 1.1

[0249] Example 4: Fungicidal activity against a liquid culture of Glomerella lagenarium (Colletotrichum lagenarium) / cucumber / preventative (Anthracnose)

[0250] The conidia of the cryogenic storage fungus 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 measured photometrically 3 to 4 days after application.

[0251] 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.

[0252] Compounds (from Table T1) 1.1

Claims (9)

1. Compound of formula (I): characterized by the fact that A is R1, R2 and R3 are hydrogen; R4 represents C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C1-2 alkoxy C13 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C1-2 alkyl; R5 represents cyano, C3-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-4 alkoxy, C1-3 hydroxyalkyl, C12 alkoxy C1-3 alkyl , C1-2 fluoroalkoxy C1-3 alkyl, C13 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl, N,N-di-C1-3 alkylamino C1-3 alkyl; or R5 represents C3-4 cycloalkyl or C3-4 cycloalkyl C1-2 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclylC1-2alkyl, wherein the heterocyclyl moiety is a 4- or 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, fluorine, chlorine, amino, hydroxyl, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy; and wherein when R5 comprises a C3-4 cycloalkyl or substituted heterocyclyl, these cycles may contain a carbonyl (C(O)) or sulfonyl (S(O)2) group; or a salt or N-oxide thereof; with the proviso that the compound of Formula (I) is not: 1,1-bis(2-methoxyethyl)-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] phenyl]methyl]urea; or 1-cyclopropyl-1-prop-2-ynyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea. 2. Compound according to claim 1, characterized by the fact that R4 is C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-2 cyanoalkyl, C1-2 alkoxy C1-alkyl 2, cyclopropyl or cyclopropylmethyl. 3. Compound according to claim 1 or 2, characterized by the fact that R4 is n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, C3-4 alkenyl , C3-4 alkynyl, cyanomethyl, cyanoethyl, methoxymethyl, ethoxymethyl, methoxyethyl, cyclopropyl or cyclopropylmethyl. 4. Compound according to any one of claims 1 to 3, characterized in that R5 is cyano, C3-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, cyanoalkyl C1-2, C1-2 alkoxy, C1-2 hydroxyalkyl, C1-2 alkoxy, C1-2 alkyl, C1-2 fluoroalkoxy, C1-2 alkyl, C1-2 aminoalkyl, N-C1-2 alkylamino, C1-2 alkyl, N, N-di-C1-2 alkylamino C1-2 alkyl, cyclopropyl or cyclopropylmethyl. 5. Compound according to any one of claims 1 to 4, characterized by the fact that R5 is n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, C3 alkenyl -4, C3-4 alkynyl, cyanomethyl, cyanoethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, aminomethyl, cyclopropyl or cyclopropylmethyl. 6. Agrochemical composition, characterized by the fact that it comprises an effective amount of a compound of Formula (I), as defined in any one of claims 1 to 5. 7. Composition, according to claim 6, characterized by the fact that it additionally comprises at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier. 8. 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 5, or a composition comprising this compound as an active ingredient is applied to the plants, their parts or their location. 9. Use of a compound of Formula (I), as defined in any one of claims 1 to 5, characterized by the fact that it is used as a fungicide excluding therapeutic use in animals and/or humans.