BR112020021645A2 - microbicidal oxadiazole derivatives - Google Patents

Abstract

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

Description

“MICROBIOCIDAL OXADIAZOL DERIVATIVES”

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

[0002] EP 0 276 432 and WO 2015/185485 describe the use of substituted oxyzoles to combat phytopathogenic fungi.

[0003] According to the present invention there is provided a compound of formula (I): (I) wherein A is A-1, A-2, A-3 or A-4; (A-1) (A-2) (A-3) (A-4)

and A-1, A-2, A-3 or A-4 are optionally substituted by one or two independently selected halogen groups; R1 and R2 are independently selected from hydrogen, methyl and cyan; or R1 and R2, together with the carbon atom to which they are attached, form a cyclopropyl ring; R3 is hydroxy, C1-4alkoxy or C1-3haloalkoxy; Z is R4, where R4 is C3-6cycloalkyl or heterocyclyl, where the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms or groups selected individually from N, NR5, O and S; wherein the cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R6; R6 is cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, cyclopropyl, prop-2-enyl, prop-2-inyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, prop-2-enyloxy, prop-2- inyloxy, N-methylamino, N, N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl, N, N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein Z can optionally contain 1 group selected from C (O) or S (O) 2; and R5 represents hydrogen, methyl, methoxy, formyl or acyl. or

R3 and Z, together with the group -NC (= S) - to which they are attached, form a 4- to 7-membered non-aromatic heterocyclyl ring, where the heterocyclyl optionally comprises 1 or 2 additional members of the ring independently selected from N , O, S, C (O) and S (O) 2, with the proviso that the heterocyclyl ring cannot contain 2 contiguous atoms selected from O and S, and the heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyan, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy; or the heterocyclyl formed by R3 and Z is replaced by a C3-6cycloalkyl group to form a spirocycle; or a salt or an N-oxide thereof.

[0004] Surprisingly, it has been 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.

[0005] According to a second aspect of the invention, an agrochemical composition is provided which comprises a fungicidal effective amount of a compound of formula (I). Such an agricultural composition may additionally comprise at least one additional active ingredient and / or an agrochemical acceptable diluent or carrier.

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

[0007] 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, the use may exclude methods for treating the human or animal body by surgery or therapy.

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

[0009] As used herein, cyano designates a -CN group.

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

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

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

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

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

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

[0016] As used herein, the term "C1-2 haloalkoxy" refers to a C1-2 alkoxy group as defined above, replaced by one or more the same or different halogen atoms. Examples of C1-2haloalkoxy include, but are not limited to, fluoromethoxy, dilfuoromethoxy, fluoroethoxy, trifluoromethoxy and trifluoroethoxy.

[0017] As used herein, the term "C3-6cycloalkyl" refers to a radical of a stable monocyclic ring that is saturated or partially unsaturated, and contains 3 to 6 carbon atoms. C3-5cycloalkyl and C3-4cycloalkyl should be interpreted accordingly. Examples of C3-6cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl, and cyclohexen-3-yl.

[0018] As used herein, the term "heterocyclyl" or "heterocyclic" generically refers to a stable, saturated or partially saturated, 4- to 6-membered monocyclic non-aromatic ring, comprising 1 or 2 individually selected nitrogen heteroatoms, oxygen and sulfur. The heterocyclyl radical can be linked to the rest of the molecule by means of a carbon atom or heteroatom. Examples of heterocyclyl include, but are not limited to, azetidinyl, oxetanyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl and morpholinyl.

[0019] 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 diastereomeric forms. Likewise, atropisomers can occur as a result of restricted rotation around a single bond. The compound of formula (I) is intended to include all of these possible isomeric forms and mixtures thereof. The present invention includes all of these possible isomeric forms and mixtures thereof for a compound of formula (I). Likewise, the compound of formula (I) is intended to include all possible tautomers (including lactam-lactime tautomerism and keto-enol tautomerism) where present. The present invention includes all possible tautomeric forms for a compound of formula (I).

[0020] In each case, the compounds of formula (I) according to the invention are in the free form, in the oxidized form as an N-oxide, in the covalently hydrated form, or in the salt form, for example, a form of agronomically usable or agrochemically acceptable salt.

[0021] N-oxides are oxidized forms of tertiary amines or oxidized forms of heteroaromatic compounds containing nitrogen. They are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0022] The following list provides definitions, including preferred definitions, for A substituents (including A-1, A-2, A-3 or A-4), Z, R1, R2, R3, R4, R5 and R6, with reference to the compounds of formula (I) of the present invention. For any of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0023] A is A-1, A-2, A-3 or A-4 (A-1) (A-2) (A-3) (A-4) where A-1, A-2, A-3 or A-4 are optionally substituted by 1 or 2 independently selected halogen groups. Preferably, the halogen is chlorine or fluorine and, more preferably, fluorine.

[0024] In some embodiments of the invention, A is A-1.

[0025] In some embodiments of the invention, A is A-2.

[0026] In some embodiments of the invention, A is A-3.

[0027] In some embodiments of the invention, A is A-4.

[0028] Preferably, A is A-1 optionally substituted by 1 or 2 fluorine groups, or A is A-4 unsubstituted. Most preferably, A is unsubstituted A-1 (1,4-phenylene) or unsubstituted A-4 (2,5-thienylene).

[0029] R1 and R2 are independently selected from hydrogen, methyl and cyan; or R1 and R2, together with the carbon atom to which they are attached, form a cyclopropyl ring; Preferably, R1 and R2 are independently selected from hydrogen and methyl (for example, R1 is hydrogen and R2 is methyl), and more preferably, R1 and R2 are hydrogen.

[0030] R3 is hydroxy, C1-4alkoxy or C1-3haloalkoxy. Preferably, R3 is C1-4alkoxy or C1-2fluoroalkoxy, and more preferably, R3 is methoxy, ethoxy or 2,2-difluoroethoxy.

[0031] Z is R4, where R4 is C3-6cycloalkyl or heterocyclyl, where the heterocyclyl portion is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms or groups selected individually from N, NR5, O and S ; wherein the cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R6.

[0032] Preferably, R4 is C3-6cycloalkyl optionally substituted with 1 or 2 substituents, which can be the same or different, selected from R6. More preferably, R4 is C3-4cycloalkyl optionally substituted with 1 or 2 substituents, which can be the same or different, selected from R6. Even more preferably, R4 is C3-4cycloalkyl optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyano, halogen, hydroxy, amino, methyl, ethyl and propyl. Even more preferably, R4 is cyclopropyl optionally substituted by 1 substituent selected from R6, where R6 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, n-propyl and iso-propyl.

[0033] R6 is cyano, halogen, hydroxy, amino, methyl, ethyl, n-propyl, iso-propyl, cyclopropyl, prop-2-enyl, prop-2-inyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, prop -2-enyloxy, prop-2-ynyloxy, N-methylamino, N, N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl, N, N-dimethylaminocarbonyl or methoxycarbonylamino.

[0034] Z can optionally contain 1 group selected from C (O) or S (O) 2.

[0035] R5 represents hydrogen, methyl, methoxy, formyl or acyl.

[0036] In other embodiments of the invention, in the compounds of formula (I), R3 and Z, together with the group - NC (= S) - to which they are attached, they can form a 4- to 7-membered non-aromatic heterocyclyl ring , wherein the heterocyclyl optionally comprises 1 or 2 additional ring members independently selected from N, O, S, C (O) and S (O) 2, with the proviso that the heterocyclyl ring cannot contain 2 contiguous atoms selected from O and S, and the heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyano, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy, or the heterocyclyl formed with R3 and Z it is replaced by a C3-6cycloalkyl group to form a spirocycle.

[0037] Preferably, R3 and Z, together with the group -NC (= S) - to which they are linked, form a group selected from: or where X1 and X2 are -CH2- or -O-, and each group is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyano, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy, and more preferably, it is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from cyano, halogen, hydroxy, amino, methyl, ethyl, C1-2 fluoroalkyl, methoxy and ethoxy, and even more preferably, it is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from halogen, methyl, ethyl and methoxy.

[0038] Preferably, the compound according to formula (I) is selected from a compound 1.1 to 1.6 listed in Table T1 (below).

[0039] Preferably, in a compound according to formula (I) of the invention: A is A-1 or A-4 optionally substituted by 1 or 2 fluorine groups; R1 and R2 are independently selected from hydrogen and methyl; R3 is C1-2alkoxy or C1-2fluoroalkoxy; and R4 is C3-4cycloalkyl optionally substituted with 1 or 2 substituents, which may be the same or different, selected from R6.

[0040] More preferably, A is A-1 or A-4 optionally substituted by 1 or 2 fluorine groups; R1 and R2 are hydrogen; R3 is methoxy, ethoxy, or 2,2-difluoroethoxy; and R4 is C3-4cycloalkyl optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R6, where R6 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl and propyl.

[0041] Even more preferably, A is unsubstituted A-1 or unsubstituted A-4; R1 and R2 are hydrogen; R3 is methoxy; and R4 is cyclopropyl optionally substituted by 1 substituent selected from R6, where R6 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, n-propyl and iso-propyl.

[0042] Preferably, in a compound according to formula (I) of the invention: A is A-1 or A-4 optionally substituted by 1 or 2 fluorine groups; R1 and R2 are independently selected from hydrogen and methyl; and R3 and Z, together with the group -NC (= S) - to which they are attached, form a group selected from: or where X1 and X2 are -CH2- or -O-, and each group is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from cyano, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy.

[0043] More preferably, A is A-1 unsubstituted or A-4 unsubstituted; R1 and R2 are independently selected from hydrogen and methyl; and R3 and Z, together with the group -NC (= S) - to which they are attached, form a group selected from: or where X1 and X2 are -CH2- or -O-, and each group is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from C1-4alkyl (for example, methyl).

[0044] The compounds of formula (I) have a thiocarbonyl moiety and it is believed that in vivo they act as a procide for compounds of formula (II) having a carbonyl fraction (eg amide or urea) under suitable conditions (eg metabolic processes or biosynthetic transformations). 1 1

R N R N 2 O 2 O

S R A O R A F F

N N N N 3 F 3 F

Z R Z R F F (I) (II)

[0045] The compounds of the present invention can be enantiomers of the compound of the formula (I) as represented by a formula (Ia) or a formula (Ib), wherein R1 and R2 are different substituents.

(Ia) (Ib)

[0046] It is understood that, when in aqueous media, the compounds of formula (I) according to the invention can be present in a reversible balance with the corresponding covalently hydrated forms (i.e., the compounds of formula (II) and formula (I-II) 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 the compounds of formula (I).

[0047] The designations of A (including A-1, A-2, A-3 or A-4), R1, R2, R3, Z, R4, and R5 with reference to the compounds of formula (I) of the present The invention generally applies to compounds of Formula (II) and Formula (I-II), as well as to specific disclosures of combinations of A (including A-1, A-2, A-3 or A-4), R1, R2 , R3, Z, R4, and R5 as represented in Tables 1.1 to 1.11, Tables 2.1 to 2.10, or the compounds

1.1 to 1.6, according to the invention listed in Table T1 (below).

[0048] The compounds of the present invention can be prepared as shown in the following schemes 1 through 14, in which, unless stated otherwise, the definition of each variable is as defined above for a compound of formula (I).

[0049] The compounds of formula (I) can be prepared from compounds of formula (II), by reactions with a suitable sulfur source [eg elemental sulfur (S8), Lawesson's reagent or P2S5], in an acceptable solvent (for example, toluene, CH2Cl2, CHCl3, tetrahydrofuran, t-butyl methyl ether), at temperatures between 0 ° C and 100 ° C. For related examples, see Hermant, F. et al Organometallics, (2014), 33, 5643; Heyde, C. et al E. J. Org. Chem. (2000), 19, 3273. This reaction is shown in Scheme 1. 1 1

R N R N 2 O 2 O

R R S R A F F

N N N N 3 F 3 F

Z R Z R

F F (II) (I) Scheme 1

[0050] The compounds of formula (III), in which Za is hydrogen, C (O) R4, C (S) R4, or R3 and Za together with the nitrogen atom to which they are attached form a non-aromatic heterocyclyl ring 4 to 7 members containing 1 or 2 groups selected from C (O) or C (S) can be prepared from compounds of formula (V), where X is OH, OSO2Me, Cl, Br or I, preferably Br or I, by reactions with compounds of formula (IV), optionally in the presence of a base (for example, triethylamine, N, N-diisopropylethylamine, K2CO3, NaHCO3, or Na2CO3), in a suitable solvent (for example , dimethylacetamide, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, toluene or acetonitrile) at temperatures between 25 ° C and 110 ° C. In some cases, better reaction performance can be obtained by using a catalyst (for example, Bu4NHSO4, Bu4NBr, Bu4NI, NaI or 4-dimethylaminopyridine) and, optionally, with microwave irradiation. For related examples see: WO 1995/9518122 and Jpn. Kokai Tokkyo Koho, (1993), 05286936; Miyawaki, K. et al Heterocycles (2001), 54, 887; WO 2003/028729; WO 2013/066839; and WO 2017/055473. This reaction is shown in Scheme 2.

(IV) (V) (III) Scheme 2

[0051] Alternatively, the compounds of formula (I), can be obtained by coupling transformations with compounds of formula (VI) and compounds of formula (VII) in a suitable solvent (for example, dimethylformamide, dichloromethane or tetrahydrofuran). hydrofuran), at temperatures between 0 ° C and 100 ° C, and optionally in the presence of a base such as triethylamine. For examples, see WO 2004/046162. The compounds of formula (VI) are commercially available. This reaction is shown in Scheme 3.

(VI) (VII) (I) Scheme 3

[0052] Additionally, the compounds of formula (I) can be prepared from the compounds of formula (VIII) by reactions with trifluoroacetic acid, trifluoroacetic ester (e.g., methyl trifluoroacetic ester or ethyl trifluoroacetic ester), trifluoroacetic anhydride or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide), optionally in the presence of a base (for example, pyridine or 4-dimethylaminopyridine) in a suitable solvent (for example, toluene, ethyl acetate, tetrahydrofuran, 2- methyltetrahydrofuran or ethanol), at temperatures between 0 ° C and 75 ° C. For related examples, see documents WO 2003/028729, WO 2017/055473 and WO 2010/045251. This reaction is shown in Scheme 4.

(VIII) (I) Scheme 4

[0053] The compounds of formula (VIII) can be prepared from compounds of formula (IX) by reactions with a hydroxylamine hydrochloride salt or a solution of hydroxylamine in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at temperatures between 0 ° C and 80 ° C. In some cases, better reaction performance can be gained with the use of a catalyst (eg, 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 5. 1 1

R R N 2 2 OH

S R A N S R A N N N H2 3 3

Z R Z R (IX) (VIII) Figure 5

[0054] The compounds of formula (IX) can be prepared from compounds of formula (X), where Y is formyl, Cl, Br, or I, via reactions promoted by metals with a cyanide reagent, such as cyan -acetone hydrochloride, dimethylmalonitrile, K4 [Fe (CN) 6], Zn (CN) 2, NaCN, or CuCN, in a suitable solvent (for example, dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 80 ° C and 120 ° C ° C, and optionally in the presence of a metal catalyst (for example, Pd or Ni) an organomagnesium or organolithium reagent. For related examples, see Reeves, J. T. et al J. Am. Chem. Soc. (2015), 137, 9481; Ushijima, S., Togo, H. Synlett, (2010), 1067; US 2007/0155739, WO 2017/055473, and WO 2009/022746. This reaction is shown in Scheme 6.

[0055] Alternatively, compounds of formula (IX) can be prepared from compounds of formula (X), where Y is NH2, by radical nucleophilic aromatic substitution reactions using a suitable nitrite source (e.g. NaNO2 or iso-amyl nitrite), a suitable acid (for example, hydrochloric acid or HBF4), and a copper source (for example, CuCN) in an acceptable solvent, such as aqueous acetonitrile, at temperatures 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 6.

(X) (IX) Scheme 6

[0056] The compounds of formula (X), where Y is CN, NH2, Cl, Br, or I, can be prepared from compounds of formula (XI), by reactions with a suitable sulfur source [ for example, elemental sulfur (S8), Lawesson's reagent or P2S5], in an acceptable solvent (for example, CH2Cl2, tetrahydrofuran, t-butylmethyl ether), at temperatures between 0 ° C and 100 ° C. For related examples, see Hermant, F. et al Organometallics, (2014), 33, 5643; Heyde, C. et al E. J. Org. Chem. (2000), 19, 3273. This reaction is shown in Scheme 7.

(XI) (X) Scheme 7

[0057] The compounds of formula (X), where Y is formyl, CN, Cl, Br, or I, can be obtained by coupling transformations with compounds of formula (VI) and compounds of formula (XII) in a suitable solvent (for example, dimethylformamide, dichloromethane or tetrahydrofuran), at temperatures between 0 ° C and 100 ° C, and optionally in the presence of a base, such as triethylamine. For examples, see WO 2004/046162. The compounds of formula (VI) are commercially available. This reaction is shown in Scheme 8.

(VI) (XII) (X) Scheme 8

[0058] The compounds of formula (XIII), where Y is CN, Cl, Br or I, and Za is hydrogen, C (O) R4, C (S) R4, or R3 and Za together with the nitrogen atom to which they are attached form a 4- to 7-membered non-aromatic heterocyclyl ring containing 1 or 2 groups selected from C (O) or C (S) can be prepared from compounds of formula (XIV), where X is OH , OSO2Me, Cl, Br or I, preferably Br or

I, by reactions with suitable compounds of formula (IV), optionally in the presence of a base (for example, triethylamine, N, N-diisopropylethylamine, K2CO3, NaHCO3, or Na2CO3), in a suitable solvent (for example , dimethylacetamide, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, toluene or acetonitrile) at temperatures between 25 ° C and 110 ° C. In some cases, a better reaction performance can be obtained through the use of a catalyst (for example, Bu4NHSO4, Bu4NBr, Bu4NI, NaI, or 4-dimethylaminopyridine) and, optionally, with microwave irradiation. For related examples see: WO 1995/9518122 and Jpn. Kokai Tokkyo Koho, (1993), 05286936; Miyawaki, K. et al Heterocycles (2001), 54, 887; WO 2003/028729; WO 2013/066839; and WO 2017/055473. This reaction is shown in Scheme 9.

(IV) (XIV) (XIII) Scheme 9

[0059] The compounds of formula (V), where X is Cl or Br, can be prepared from compounds of formula (XV), via reactions with a suitable halogen source (eg, N-bromosuccinimide ( NBS) or N-chlorosuccinimide (NCS)) and a radical initiator (eg, PhCO2) 2 or azobisisobutyronitrile (AIBN)) in a suitable solvent, such as tetrachloromethane, at temperatures between 55 ° C and 100 ° C, optionally at presence of ultraviolet light. For related examples, see WO 2017/055473; Liu, S. et al Synthesis (2001), 14, 2078; and Kompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794, and WO 2017/055473. This reaction is shown in Scheme 10.

(XV) (V) Scheme 10

[0060] Alternatively, compounds of formula (V) where X is OH, OSO2Me, Cl, Br or I, preferably OH, can be prepared from compounds of formula (XVI) by means of reactions with trifluoroacetic acid, ester trifluoroacetic acid (for example trifluoroacetic methyl ester or trifluoroacetic ethyl ester), trifluoroacetic anhydride or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide) optionally in the presence of a 4-dimidine or pyridine based solvent (for example, toluene, ethyl acetate, tetrahydrofuran, 2-methyltetrahydrofuran or ethanol), at temperatures between 0 ° C and 75 ° C. For related examples, see WO 2003/028729, WO 2017/055473 and WO 2010/045251. This reaction is shown in Scheme 11.

(XVI) (V)

Layout 11

[0061] The compounds of formula (XVI) where X is OH, OSO2Me, Cl, Br or I, preferably OH, can be prepared from compounds of formula (XVII), by reactions with a hydroxylamine hydrochloric salt or a solution of hydroxylamine in water, optionally in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at temperatures between 0 ° C and 80 ° C. In some cases, better reaction performance can be obtained by using a catalyst (for example, 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 12.

(XVII) (XVI) Layout 12

[0062] The compounds of formula (XVII), where X is OH, OSO2Me, Cl, Br, or I, are commercially available or can be prepared from compounds of formula (XVIII), where Y is formyl, Cl , Br, or I, via reactions promoted by metals with a cyanide reagent, such as acetone cyanohydrin, dimethylmalonitrile, K4 [Fe (CN) 6], Zn (CN) 2, NaCN, or CuCN, in a solvent suitable (eg, dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 80 ° C and 120 ° C, and optionally in the presence of a metal catalyst (eg, Pd or Ni) an organomagnesium or organolithium reagent . For related examples, see Reeves, J. T. et al J. Am. Chem. Soc. (2015), 137, 9481; Ushijima, S., Togo, H. Synlett, (2010), 1067; US 2007/0155739; WO 2017/055473; and WO 2009/022746. This reaction is shown in Scheme 13.

[0063] Alternatively, compounds of formula (XVII), in which X is OH, OSO2Me, Cl, Br or I, can be prepared from compounds of formula (XVIII), in which Y is NH2, by means of reactions radical nucleophilic aromatic substitution using a suitable nitrite source (eg NaNO2 or iso-amyl nitrite), suitable acid (eg hydrochloric acid or HBF4), and a copper source (eg CuCN) in a system of acceptable solvent, such as acetonitrile and water, at temperatures 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 13.

(XVIII) (XVII) Layout 13

[0064] Alternatively, the compounds of formula (XVIII), where X is Cl, Br, I or OSO2Me and Y is formyl, NH2, Cl, Br, I, CN, or 5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl, are commercially available or can be prepared from compounds of formula (XIX), by reactions with a suitable acid source (for example, hydrochloric acid, hydrobromic acid or hydroiodic acid), or suitable halogen source (for example, tetrabromomethane, tetrachloromethane or iodine) in the presence of triphenylphosphine, or with methanesulfonyl chloride (ClSO2Me), in a suitable solvent (for example, dichloromethane), optionally in the presence of a base (for example, 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. The compounds of formula (XIX) are either commercially available or can be prepared using known methods. This reaction is shown in Scheme 14.

(XIX) (XVIII) Layout 14

[0065] As already indicated, surprisingly it has now been discovered that the compounds of formula (I) of the present invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0066] The compounds of formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for plant pest control or in non-living materials for the control of microorganisms that cause deterioration or potentially organisms harmful to man. The new compounds are distinguished by their excellent activity at low application rates, by being well tolerated by plants and by being environmentally safe. They have very useful healing, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy pests that occur on plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) from different crops of useful plants, while also protecting those parts of plants that grow later, for example, of phytopathogenic microorganisms.

[0067] The present invention relates additionally to a method for controlling or preventing infestation of plants or plant propagating material and / or collected food crops susceptible to microbial attack by treating plants or plant propagating material and / or collected food crops , wherein an effective amount of a compound of formula (I) is applied to plants, parts thereof or their locus.

[0068] It is also possible to use compounds of formula (I) as a fungicide. The term "fungicide", as used herein, designates a compound that controls, modifies or prevents the growth of fungi. The term "fungicidal effective amount", when used, means the amount of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Control or modification effects include all deviations from natural development, such as death, retardation and the like, and prevention includes a barrier or other defensive formation on or over a plant to prevent fungal infection.

[0069] It may also be possible to use compounds of formula (I) as curative agents for the treatment of plant propagating material, for example seeds, such as fruits, tubers or grains, or plant cuttings, to protect 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 the 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), by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention also relates to such methods of treating plant propagating material and to the plant propagating material so treated.

[0070] Additionally, the compounds of formula (I) can be used to control fungi in related areas, for example, in the protection of mechanical materials, including technical products related to wood and wood, in food storage, in hygiene management.

[0071] Additionally, the invention could be used to protect non-living materials from fungal attack, for example, construction wood, wall panels and paint.

[0072] 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 disease vectors, as well as phytopathogenic bacteria and viruses, are for example: Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii , Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp.

Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonosporph sp. 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.

[0073] The compounds of formula (I) can be used for example in grass, ornamental plants, such as flowers, shrubs, leafy or evergreen trees, for example conifers, as well as for injection into trees, pest management and the like .

[0074] Within the scope of the present invention, target crops and / or useful plants to be protected typically comprise perennial and annual crops, such as berries, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (maize), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar beet and fodder, coffee, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, for example Bermuda grass, blue grass, agrostis, centipede grass, fescue, ryegrass, Saint Augustine grass and Zoysia grass; aromatic herbs such as basil, borage, chives, coriander, lavender, levistical, mint, oregano,

parsley, rosemary, sage and thyme; legumes, for example beans, lentils, peas and soy; hard-shelled fruits, for example almond, cashew, peanut seed, hazelnut, peanut, pecan, pistachio and walnut; palms, for example palm oil; ornamental plants, for example flowers, shrubs and trees; other trees, for example cocoa, coconut, olive and rubber; vegetables, for example asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomatoes; and vines, for example grapes.

[0075] The term "useful plants" is to be understood as including also useful plants that have been made tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, eg primisulfuron , prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-chiquimate-3-phosphate synthase) inhibitors, GS (glutamine synthase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional methods of improvement or modification genetics. An example of a crop that has been made tolerant to imidazolinones, for example, imazamox, by conventional breeding methods (mutagenesis) is the Clearfield® summer rape (Canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic engineering methods include varieties of glyphosate and glufosinate resistant maize, commercially available under the trademarks RoundupReady®, Herculex I and LibertyLink®.

[0076] The term "useful plants" should be understood as also including useful plants that have been thus transformed by the use of recombinant DNA techniques, which are capable of synthesizing one or more selectively active toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[0077] Examples of such plants are: YieldGard (a variety of more that expresses a CryIA toxin (b)); YieldGard Rootworm (a variety of maize that expresses a CryIIIB toxin (b1)); YieldGard Plus (a variety of more that expresses a CryIA toxin (b) and a CryIIIB toxin (b1)); Starlink (a variety of maize that expresses a Cry9 toxin (c)); Herculex I (a variety of more that expresses a CryIF toxin (a2) and the enzyme phosphinothricin N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B (a cotton variety that expresses a CryIA toxin (c)); Bollgard I (a cotton variety that expresses a CryIA toxin (c)); Bollgard II® (a cotton variety that expresses a CryIA toxin (c) and a CryIIA toxin (b)); VIPCOT (a cotton variety that expresses a VIP toxin); NewLeaf (a potato variety that expresses a CryIIIA toxin); NatureGard Agrisure® GT Advantage (glyphosate tolerance characteristic GA21), Agrisure® CB Advantage (corn borer (CB) Bt11 characteristic), Agrisure® RW (corn rootworm characteristic) and Protecta.

[0078] The term "cultures" is to be understood as also including culture plants that have been so transformed by the use of recombinant DNA techniques in order to be able to synthesize one or more selectively acting toxins, as they are known, by example, toxin-producing bacteria, especially those of the genus Bacillus.

[0079] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins of Bacillus cereus or Bacillus popilliae, or insecticidal proteins of Bacillus thuringiensis, such as δ-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A, or insecticidal proteins of 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 toxins from Streptomycetes, plant lectins, such as pea lectins, barley lectins or white bell lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, more RIP, abrina, lufina, saporina or briodina; steroid metabolism enzymes,

such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA reductase, ion channel blockers, such as sodium or calcium channel blockers, juvenile hormone esterase, hormone receptors diuretics, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0080] Additionally, in the context of the present invention, δ-endotoxins, for example Cry1Al, Cry1Ac, Cry1F, Cry1Fa2, Cry2Al, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, are to be understood Vip2, Vip3 or Vip3A, also expressly 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, for example, a truncated Cry1Ab, are known. In the case of modified toxins, one or more naturally occurring toxin amino acids are replaced. In such amino acid substitutions, preferably non-naturally occurring 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 ).

[0081] 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.

[0082] 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.

[0083] The toxin contained in transgenic plants gives plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), double-winged insects (Diptera) and butterflies (Lepidopterans).

[0084] Transgenic plants containing one or more genes that encode an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard (variety of maize that expresses a Cry1Ab toxin); YieldGard Rootworm (variety of maize that expresses a Cry3Bb1 toxin); YieldGard Plus (variety of maize that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink (variety of maize that expresses a Cry9C toxin); Herculex I (variety of maize that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin-N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B (cotton variety that expresses a Cry1Ac toxin); Bollgard I (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac toxin and a Cry2Ab toxin); VipCot (cotton variety that expresses a Vip3A and a Cry1Ab toxin); NewLeaf (potato variety that expresses a Cry3A toxin); NatureGard, Agrisure® GT Advantage (characteristic tolerant to glyphosate GA21), Agrisure® CB Advantage (characteristic of corn borer (CB) Bt11) and Protecta. Additional examples of such transgenic crops are:

[0085] 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 made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. More Bt11 also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonia.

[0086] 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 made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 corn also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

[0087] 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. More that has been made resistant to insects by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by inserting a cathepsin G protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

[0088] 4. More MON 863 from Monsanto Europe S.A. 270- 272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02/9. MON 863 expresses a Cry3Bb1 toxin and is resistant to certain Coleopteran insects.

[0089] 5. Monsanto Europe S.A. IPC 531 cotton 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96/02.

[0090] 6. More 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00/10. More genetically modified for the expression of the Cry1F protein to achieve resistance to certain Lepidoptera insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

[0091] 7. More NK603 × MON 810 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of hybrid maize varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. Maize NK603 × MON 810 transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium sp., Which confers tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki that confers tolerance to certain Lepidoptera, including the European corn borer.

[0092] The compounds of formula (I) can be used to control or prevent phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi), in soybean plants.

[0093] In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins, such as delta-endotoxins, for example, Cry1Ac (Bt Cry1Ac protein). Consequently, this may include transgenic soybean plants comprising the MON87701 event (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (see, for example, the reference in paragraph [008] to Intacta soybean RR2 PROTM)), event MON87751 (U.S. Patent Application Publication No. 2014/0373191) or DAS-81419 event (U.S. Patent No. 8632978 and related applications and patents).

[0094] Other transgenic soybean plants may comprise the event SYHT0H2 - tolerance to HPPD (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (US Pat. No. 7,632,985 and related patents and orders), event MON87708 - dicamba tolerance (US Patent Application Publication No. 2011/0067134 and related patents and orders), event DP-356043-5 - glyphosate tolerance and ALS (Patent Application Publication US No. 3 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (US Patent Application Publication No. 2008/0320616 and related applications and patents), event DP-305423-1 -

tolerance to ALS (US Patent Application Publication No. 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolerance (US Patent Application Publication No. 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 - ALS tolerance (WO 2010/080829 and related orders 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 - tolerance to ALS and GU262 - tolerance to glufosinate or SYHT04R event - tolerance to HPPD.

[0095] The compounds of formula (I) can be used to control or prevent phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi), in soybean plants. In particular, certain varieties of Elite soy plants are known in the scientific literature where stacks of the R gene, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been introgressed in the plant's genome, see, for example: "Fighting Asian Soybean Rust ", Langenbach C, et al, Front Plant Science 7 (797) 2016).

[0096] An elite plant is any plant in an elite line, in such a way that an elite plant is a plant representative of an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to soybean farmers or breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, Ill., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex., USA); JG 03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R; and P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Ind., USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S007-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. Ia., USA); or Armor 4744 (Armor Seed, LLC, Ar., USA).

[0097] Thus, in an additionally preferred embodiment, the compounds of formula (I) are used to control Phakopsora pachyrhizi, (including their fungicide-resistant strains, as described below) in varieties of Elite soy plants where the R gene stacks ,

conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, were introgressed in the plant genome. Numerous benefits can be expected as a result of such use, for example, improved biological activity, an advantageous or broader spectrum of activity (including sensitive and resistant strains of Phakopsora pachyrhizi), an increased safety profile, improved crop tolerance, synergistic interactions or enhancing properties, improved onset of action or residual activity of longer duration, a reduction in the number of applications and / or a reduction in the application rate of compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thus allowing beneficial resistance management practices, reduced environmental impact and reduced operator exposure.

[0098] Strains of Phakopsora pachyrhizi resistant to fungicides have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following classes of fungicidal modes of action being observed: steroid demethylation inhibitors (DMI), external quinone (QoI) inhibitors and succinate dehydrogenase (SDHI) inhibitors. See, for example: "Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms." Schmitz HK et al, Pest Manag Sci (2014) 70: 378-388; "First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi" Simões K et al, J Plant Dis Prot (2018) 125: 21-2; "Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes". Klosowski AC et al, Phytopathology (2016) 106: 1278-1284; "Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi". Klosowski AC et al, Pest Manag Sci (2016) 72: 1211-1215.

[0099] Thus, in a preferred embodiment, the compounds of formula (I) are used to control Phakopsora pachyrhizi which are resistant to one or more fungicides from any of the following MoA fungicidal classes: sterol demethylation inhibitors (DMI), inhibitors of external quinoa (QoI) and succinate dehydrogenase (SDHI) inhibitors.

[0100] The term “locus”, as used herein, designates fields in, or on, which plants are grown, or where seeds of cultivated plants are sown, or where the seeds will be placed in the soil. It includes soil, seeds and seedlings, as well as established vegetation.

[0101] The term "plants" refers to all the physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[0102] It is understood that the term "plant propagation material" denotes generative parts of the plant, such as seeds, that 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 can be mentioned. Germinated plants and young plants that are to be transplanted after germination or after emergence from the soil can also be mentioned. These young plants can be protected before transplantation by total or partial immersion treatment. Preferably, "plant propagation material" is understood to denote seeds.

[0103] The compounds of formula (I) can be used in unmodified form or, preferably, in conjunction with adjuvants conventionally employed in the formulation technique. For this purpose, emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dust, granules and also encapsulations, for example, in polymeric substances can be conveniently formulated in a known manner. As with the type of compositions, the application methods, such as spraying, atomizing, dusty, dispersing, coating or spilling, 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 tackifiers, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0104] Suitable carriers and adjuvants, for example for agricultural use, can be solid or liquid and are useful substances in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, stickiness promoters, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.

[0105] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-sedimentation agents and dispersing agents and may additionally include a wetting agent to enhance the activity as well as a defoamer and a crystal growth inhibitor. In use, these concentrates are diluted with water and usually 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.

[0106] Wettable powders are in the form of finely divided particles that rapidly disperse in water or other liquid vehicles. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include Fuller earth, kaolin clays, silica and other readily moist organic or inorganic solids. Wettable powders normally contain 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0107] 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 vehicle, such as xylene, heavy aromatic naphthas, isophorone and others non-volatile organic solvents. In use,

these concentrates are dispersed in water or another liquid and usually 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.

[0108] Granular formulations include both extruded and relatively coarse particles and are usually applied without dilution to the area where treatment is required. Typical carriers for granular formulations include sand, Fuller earth, atapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, 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 normally contain 5% to 25% of active ingredients that may include surfactants such as heavy aromatic naphthas, kerosene and other fractions of petroleum or vegetable oils; and / or adherents such as dextrins, glue or synthetic resins.

[0109] Dusts are free-flowing mixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids that act as dispersants and carriers.

[0110] Microcapsules are typically droplets or granules of the active ingredient encased in an inert porous shell that allows the enclosed material to escape into the vicinity 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 can include a solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form within the granule pores. The granules typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter. The granules are formed by extrusion, agglomeration or pelletizing or occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, atapulgite 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 xanthate.

[0111] 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 can also be used, in which the active ingredient is dispersed in a finely divided form due to the vaporization of a dispersing solvent vehicle with a low boiling point.

[0112] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the types of formulations described above are well known to those skilled in the art.

[0113] Liquid vehicles that can be used 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, 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 - 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 ol, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methylisoamylketone,

methylisobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol ( PEG400), propionic acid, propylene glycol, propylene glycol monoethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, methanol, acetyl, acetate , ethanol, isopropanol and higher molecular weight alcohols, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for diluting concentrates.

[0114] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, atapulgite clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller earth, bark cottonseeds, wheat flour, soy flour, pumice stone, wood flour, nutshell flour and lignin.

[0115] A wide range of surfactants is advantageously employed in said liquid and solid compositions, especially those designed to be diluted with a vehicle before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surfactants include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as C 18 nonylphenol-ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl-ethoxylate alcohol 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 lauryl trimethylammonium 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.

[0116] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light blocking agents, compatibilizing agents, antifoaming agents , sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, flavorings, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0117] Furthermore, in addition, other biocidal active ingredients or compositions can be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these additional active ingredients can be formulated together with the compositions of the invention or mixed, for example, in the spray tank. These biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0118] Pesticide agents are referred to here using their common name, being known, for example, from “The Pesticide Manual”, 15th Edition, British Crop Protection Council 2009.

[0119] Additionally, the compositions of the invention can also be applied with one or more inductors of systemically acquired resistance ("SAR" inductor). SAR inducers are known and described, for example, in United States Patent No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0120] The compounds of the formula (I) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated,

simultaneously or in succession with additional compounds. These additional compounds can be, for example, fertilizers or micronutrient donors or other preparations, which influence plant growth. They can also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired in conjunction with additional carriers, surfactants or application-promoting adjuvants commonly employed in the formulation technique.

[0121] The compounds of the formula (I) can be used in the form of compositions (fungicides) for control or protection against phytopathogenic microorganisms, comprising as active ingredient at least one compound of the formula (I) or at least one preferred individual compound as defined here, in free form or in agrochemically usable salt form, and at least one of the aforementioned adjuvants.

[0122] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier and optionally an adjuvant. An acceptable agricultural carrier is, for example, a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition can comprise at least one or more active compounds as a pesticide, for example, an active fungicidal active ingredient in addition to the compound of formula (I).

[0123] The compound of formula (I) may be the only active ingredient in a composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator, where appropriate . An additional active ingredient can, in some cases, result in unexpected synergistic activities.

[0124] 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, arylphenyl ketone fungicides, benzamide fungicides, benzanidide, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, fungicides, fungicides dithiolane, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphate fungicides, organo-tin fungicides, oxatiin fungicides, oxazole fungicides, phenyl fungicides, fungalides python ol, pyridine fungicides, pyrimidine fungicides,

pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazoline fungicides, thiazolidine fungicides, thiocarbamatic fungicides, thiocarbamatic fungicides triazine, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0125] Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4 -methane-naphthalen-5-yl) -amide, 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid methoxy- [1-methyl-2- (2,4,6-trichlorophenyl) -ethyl] - amide, 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl) -amide (1072957-71-1), acid 1- methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-4H-pyrazol-4-carboxylic acid [2- (2, 4-dichloro-phenyl) -2-methoxy-1-methyl-ethyl] -amide, (5-Chloro-2,4-dimethyl-pyridin-3-yl) - (2,3,4-trimethoxy-6-methyl -phenyl) - methanone, (5-Bromo-4-chloro-2-methoxy-pyridin-3-yl) - (2,3,4-trimethoxy-6-methyl-phenyl) -methanone, 2- {2- [ (E) -3- (2,6-Dichloro-phenyl) -1-methyl-prop-2-en- (E) -ylideneaminooxymethyl] - phenyl} -2 - [(Z) -methoxyimino] -N-methyl- acetamide, 3- [5- (4-Chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyri dine, (E) - N-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxy-

iminoacetamide, 4-bromo-2-cyano-N, N-dimethyl-6-trifluoromethyl-benzimidazole-1-sulfonamide, α- [N- (3-chloro-2,6-xylyl) -2-methoxyacetamido] -i-butyrolactone, 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide, N-allyl-4,5, -dimethyl-2-trimethylsilylthiophene-3-carboxamide, N- (l-cyano- 1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propionamide, N- (2-methoxy-5-pyridyl) - cyclopropane carboxamide, (. + -.) - cis-1- (4-chlorophenyl) - 2- (1H-1,2,4-triazol-1-yl) -cycloheptanol, 2- (1-tert-butyl) -1- (2-chlorophenyl) -3- (1,2,4-triazole-1 -yl) -propan-2-ol, 2 ', 6'- dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 1-imidazolyl-1- (4' -chlorophenoxy) - 3,3-dimethylbutan-2-one, (E) -2- [2- [6- (2- cyanophenoxy) pyrimidin-4-yloxy] phenyl] 3-methyl methoxyacrylate, (E) -2 - Methyl [2- [6- (2-thioamidophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2- fluorophenoxy) pyrimidin-4-yloxy] methyl phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2,6-difluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate methyl, (E) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [2- [3- (5-methylpyrimidin- Methyl 2-yloxy) -phenoxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (phenyl-sulfonyloxy) phenoxy] methyl-3-methoxyacrylate, (E) -2- [ Methyl 2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate, (E) -2- [2-phenoxyphenyl] -3-methyl methoxyacrylate, (E) -2- [2- (3 , Methyl 5-dimethyl-benzoyl) pyrrol-1-yl] -3-methoxyacrylate, (E) -2- [2- (3-methoxyphenoxy) phenyl] -3-methyl-methoxyacrylate, (E) -2 [2 - (2-phenyleten-1-yl) -phenyl] -3-

methyl methoxyacrylate, (E) -2- [2- (3,5-dichlorophenoxy) pyridin-3-yl] -3-methyl methoxyacrylate, (E) -2- (2- (3- (1,1, Methyl 2,2-tetrafluoroethoxy) phenoxy) phenyl) -3-methoxyacrylate, (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methyl methoxyacrylate, (E) -2 - methyl (2- (4-phenoxypyridin-2-yloxy) phenyl) -3-methoxyacrylate, (E) -2- [2- (3-n-propyloxy-phenoxy) phenyl] 3-methyl methoxyacrylate, (E ) Methyl -2- [2- (3-isopropyloxyphenoxy) phenyl] -3-methoxyacrylate, (E) - 2- [2- [3- (2-fluorophenoxy) phenoxy] phenyl] -3-methoxyacrylate, ( E) -2- [2- (3-ethoxyphenoxy) phenyl] -3-methyl methoxyacrylate, (E) -2- [2- (4-tert-butyl-pyridin-2-yloxy) phenyl] -3-methoxyacrylate methyl, (E) -2- [2- [3- (3- cyanophenoxy) phenoxy] phenyl] -3-methyl methoxyacrylate, (E) - 2- [2 - [(3-methyl-pyridin-2- methyl yloxymethyl) phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-methyl-phenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2 - Methyl [2- (5-bromo-pyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate, (E) -2- [2- (3- (3-iodopyridin-2-yloxy) fe noxi) methyl phenyl] -3- methoxyacrylate, (E) -2- [2- [6- (2-chloropyridin-3-yloxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) , (E) -2- [2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl) phenyl] -3-methyl-methoxyacrylate, (E) - 2- {2- [6- (6-methylpyridin-2-yloxy ) methyl pyrimidin-4-yloxy] phenyl} -3-methoxy-acrylate, (E), (E) -2- {2- (3-methoxyphenyl) methyloximinomethyl] -phenyl} -3-methoxyacrylate, (E) - Methyl 2- {2- (6- (2-azidophenoxy) -pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, (E), (E) -2- {2- [6-

methyl phenylpyrimidin-4-yl) -methyloximinomethyl] -methyl} -3-methoxyacrylate, (E), (E) -2- {2 - [(4-chlorophenyl) -methyloximinomethyl] -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) methyloximinomethyl] phenyl} -3-methyl-methoxyacrylate, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in) , 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formaldehyde, 3-bromo-2,3-diiodo-2- ethylcarbamate propenyl, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl n-butylcarbamate, 3-iodine-2-propynyl n-hexylcarbamate, cyclohexyl 3-iodo-2-propynyl 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-benzoditiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro- (3H) -1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1, 3,5-thiadiazine-2-thione, N- (2-p-chlorobenzylethyl) chloride - hexaminium, acibenzolar, acipetacs, alanicarb, albendazole, aldimorf, allicin, allyl alcohol, ametoctradin, amisulbrom, amobam, ampropylphos, anilazine, anilazine , aureofungin, azaconazole, azafendin, azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanyl, benomile, benquinox, bentaluron,

bentiavalicarb, bentiazole, benzalkonium chloride, benzamacril, benzamorf, benzohydroxamic acid, benzovindiflupir, berberine, betoxazin, biloxazole, binapacrila, biphenyl, bitertanol, bitionol, bixafen, blasticidin-butyl, bromo, bromil, bromo calcium, captafol, captan, carbamorf, carbendazim, carbendazim hydrochloride, carboxin, carpropamide, carvone, CGA41396, CGA41397, quinomethionate, chitosan, clobentiazone, chloraniformetan, chloranil, chlorphenazole, chloroneb, chloropiczin, chloropicrin, chloropicrin, chlorotropic clozilacon, copper-containing compounds, such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper talate, copper chromate copper and zinc and Bordeaux mixture, cresol, cufraneb, cuprobam, cuprous oxide, cyzofamide, cyclamfuramide, cycloheximide, ciflufenamid a, cymoxanil, cipendazole, cyproconazole, ciprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, di-2-pyridyl 1,1'-dioxide disulfide, diclofluanid, diclomezine, diclone, dicloran, dichlorofen, dicloquinoline, diclozoline, diclozoline , diphenoconazole, difenzoquat, diflumetorim, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimetconazole, dimetomorf, dimetirimol, diniconazole, diniconazole-M, dinobutone, dinocap, dinosaur, dinosaur, dinosaur, dinosaur, dinosaur , dipyrithione,

disulfiram, ditalimphos, ditianon, dithioether, dodecyl dimethyl ammonium chloride, dodemorf, dodicin, dodine, doguadine, drazoxolon, edifenfos, enestroburin, epoxiconazole, etaconazole, etem, etaboxy-ethoxy-ethoxy, ethanol, ethanol; Ethyl N ([methyl (methylthioethylideneamino-oxycarbonyl) amino] thio) -ß-alaninate, etridiazole, famoxadone, fenamidone, phenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamide, fenitropan, fenoxil, phenoxy, phenoxyl, phenoxy, phenoxyl, phenoxy, phenoxyl, phenoxy fenpropimorf, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorf, flupicolide, fluopiram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusilanfluid, fluusulfan, formaldehyde, fosetila, fuberidazole, furalaxil, furametpir, furcarbanila, furconazole, furfural, furmeciclox, furofanato, gliodin, griseofulvin, guazatina, halacrinato, hexachlorobenzene, hexachlorobut adiene, hexachlorophene, hexaconazole, hexylthiophes, hydrargafen, hydroxyisoxazole, himexazole, imazalil, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine, inezin, iodocarb, ipodazypropyl, iodine, carbone, iodine, carbone isothianyl, isovaledione, izopamphos, casugamycin, kresoxim-methyl, LI186054, LI211795, LI248908, mancozeb, mandipropamide, maneb, mebenila, mecarbinzid, mefenoxam, mefentrifluconazole, mepanipil, chloramyl, meprep, meprep, methyl , metam, metazoxolon, metconazole, metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxidine, miclobutanil, nemalamino, niclamino, niclamino, nickel, nitrostirene, nitrotal-iso-propyl, nuarimol, octylinone, ofurace, organ compounds omercurium, orisastrobin, ostol, oxadixil, oxasulfuron, oxatiapiprolin, oxin-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencicuron, penflufen, pentachlorophenol, pentiopirid, phenoxyldine, phenoxycrine, phenoxycrine, phosphorus, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxyrin, polamen, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazide, protiocarb, protioconazole, pidifactrin, pidifactrol, pidifactrin , pyrazophos, pyribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyrophenone, piroquilon, pyroxychlor, pyroxyfur, pyrrolnitrine, quaternary ammonium compounds, quinacetol, quinazamide, quinconazole, quinometion, quinoxifen, quintoxazole, silatonazole, siloxane sodium pentachlorophenate, spiroxamine, streptomycin, streptomycin, sulfur, south tropen, tebuconazole, tebfloquine, keyboardoftalam, tecnazene, weave, tetraconazole,

thiabendazole, thiadifluor, ticiofen, tifluzamide, 2- (thiocyanomethylthio) benzothiazole, thiofanate-methyl, thioquinox, tiram, thiadinyl, timibenconazole, thioximide, tolclofos-methyl, tolylfluanid, triadimefia, triadimide, triadimide, triadol, triadol , trifloxystrobin, triflumazole, triforin, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozoline, zarilamide, zineb, ziram and zoxamide.

[0126] The compounds of the invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the class of macrocyclic lactone compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP-357460, EP- 444964 and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include 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, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include fluquicides such as triclabendazole and clorsulon, and cestocides such as praziquantel and epsiprantel.

[0127] The compounds of the invention can be used in combination with derivatives and analogs of the class of paraherquamide / marcfortin anthelmintic agents, as well as antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE-19520936 .

[0128] The compounds of the invention can be used in combination with derivatives and analogs of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173 and EP 0 503 538.

[0129] 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.

[0130] The compounds of the invention can be used in combination with terpene alkaloids, for example, those described in International Patent Application Publications Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.

[0131] Other examples of such biologically active compounds with which the compounds of the invention can be used in combination include the following, but are not restricted to these:

[0132] Organophosphates: Aphosphate, azametiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chlorpyrifos, chlorfenvinfos, chlormefos, demeton, demeton-S-methyl, demeton-S-meton-de-dialon-s-metilson-dialsone , dichlorvós, dicrotofos, dimetoato, disulfoton, etion, etetoprofos, etrinfos, fanfur, fenamifos, fenitrotion, fensulfotion, fention, flupirazofos, fonofos, formotion, fostiazato, heptenofos, isazofos, isothioid, methoxy, methoxylation, isoxation, isoxation, methalation -paration, mevinfos, monocrotofos, naled, ometoate, oxidometon-methyl, paraoxon, paration, paration-methyl, fentoate, fosalone, phospholane, phosfocarb, fosmet, phosphamidon, forato, foxima, pirimiphos, pirimifos-methyl, profenofos, propafos, propafos, propafos, propafos , protiofos, piraclofos, piridapention, quinalfos, sulprofos, temefos, terbufos, tebupirinfos, tetrachlorvinfos, timeton, triazofos, triclorfona, vamidotion.

[0133] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloetocarb, etiofencarb, phenoxycarb, fentiocarb, furatiocarb, HCN-801, isoprocarb, 5 -m- cumenylbutyryl (methyl) carbamate, oxamyl, pyrimicarb, propoxur, tiodicarb, thiophanox, triazamate, UC-51717.

[0134] Pyrethroids: acrinatin, alethrin, alfamethrin, (E) - (1R) -cis-2,2-dimethyl-3- (2-oxothiolan-3-

ilidenomethyl) 5-benzyl-3-furylmethyl cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, α-cypermethrin, beta-cypermethrin, bioalectrin, bioalethrin (isomer (S) -cyclopentyl), biormethrin, cycloprotine, bifentrine, 85- cyhalothrin, cytitrine, cyphenothrin, deltamethrin, empentrin, sphenolvalerate, etofenprox, fenflutrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cialethrin, permethrin, pretrothyrin, permethrin, permethrin, permethrin, permethrin, pretrothyrin, permethrin, pretrothyrin resmethrin, tetramethrin, transflutrin, theta-cypermethrin, silafluofen, t-fluvalinate, teflutrin, tralometrine, Zeta-cypermethrin.

[0135] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, chlorofluorine, triflazoline, triflazoline; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyphene, methoprene (including S-methoprene), phenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0136] Other antiparasitic agents: acequinocila, amitraz, AKD-1022, ANS-118, azadiractin, Bacillus turingiensis, bensultape, biphenazate, binapacryl, bromopropylate, BTG-504, BTG-505, canfeclor, cartape, chlorodenzema, chlorodiene ,

clothianidin, cyromazine, diaclodene, diafentiurone, DBI-3204, dinactin, di-hdroxymethyldihydroxypyrrolidine, dinobutone, dinocape, endosulfan, etiprol, etofenprox, phenazaquin, flumite, MTI- 800, flake, fluoride, flaminophen, fluorimine, fluoro, fluproxifene, halofenprox, hydramethylnone, IKI-220, canemite, NC-196, neem protector, nidinorterfuran, nitanpyram, SD-35651, WL-108477, pyridine, propargite, protrifenbute, pimetrozine, pyridine, pyridine, pyrim, 195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosade, tebufenpirade, tetradifone, tetranactin, thiaclopride, thiocyclamide, thiamethoxam, tolfenpirade, triazamate, trisoxine, tri trinactin, verbutin, vertalec, YI-5301.

[0137] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis endotoxin delta, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0138] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0139] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprol, cefquinoma, florfenicol, buserelin, cefoviprine, trefohydrate, cefovecin, trefovinine, trefovinine, cefovecin, trefovinine, cefovecin, trefohydrate .

[0140] The following mixtures of the compounds of formula (I) with active ingredients are preferred. The abbreviation “TX” means a compound selected from the group consisting of the compounds represented in Tables 1.1 to

1.11, Tables 2.1 to 2.10, or compounds 1.1 to 1.6 according to the invention listed in Table T1 (below): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX, an acaricide selected from the group of substances consisting of 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC / Chemical Abstracts name) (1059) + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprol [CCN] + TX, acrinatrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidition (870) + TX, amidoflumet [CCN ] + TX, amidothioate (872) + TX, amiton (875) + TX, amitone hydrogenoxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenious oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotine (46) + TX, nitrogen (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [ CCN] + TX, benzoxide (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, biphenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name ) + TX, broflanilide [1207727-04-5] + TX, bromocyclene (918) + TX, bromophos (920) + TX, bromophos-ethyl

(921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxy (103) + TX, butoxycarboxy (104) + TX, butylpyridabene (alternative name) + TX, calcium polysulfide (IUPAC name) ( 111) + TX, canfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbofenotion (947) + TX, CGA 50'439 (development code) ( 125) + TX, quinomethionate (126) + TX, clorbenside (959) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorphenethol (968) + TX, chlorfensone (970) + TX, chlorfensulfide (971) + TX, chlorfenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos ( 145) + TX, chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, clofentezine (158) + TX , closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamiton (alternative name) [CCN] + TX, crot oxyphos (1010) + TX, cufraneb (1013) + TX, cyantoate (1020) + TX, kyflumetophen (Reg.

CAS NO .: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX , demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX , demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialiphos (1042) + TX, diazinon (227) + TX, dichlofluanide (230) + TX, dichlorvos (236) + TX,

diclifos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimetoate (262) + TX, dinactin (alternative name) (653 ) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxation (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram ( alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endotion ( 1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, etion (309) + TX, ethoate-methyl (1134) + TX, ethoxazole (320) + TX, etrimphos (1142) + TX, phenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropatrin (342) + TX, fenpirad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacripyrim (360) + TX, fluazuron (1166) + TX, flubenzimine ( 1167) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) ) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, range- HCH (430) + TX, gliodine (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate

(IUPAC name / Chemical Abstracts) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, O- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, Jasmine I (696) + TX, Jasmine II (696) + TX, Jodfenfos (1248) + TX, Lindane (430) + TX , lufenuron (490) + TX, malation (492) + TX, malonobene (1254) + TX, mecarbam (502) + TX, mefosfolane (1261) + TX, messulfene (alternative name) [CCN] + TX, metacryphs (1266 ) + TX, metamidophos (527) + TX, metidation (529) + TX, metiocarb (530) + TX, methomyl (531) + TX methyl bromide (537) + TX, metolcarb (550) + TX, mevinfos (556 ) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotofos (561) + TX, morfotion (1300) + TX , moxidectin (alternative name) [CCN] + TX, nalede (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nif luridide (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb complex and zinc chloride 1: 1 (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxisulfoton (1325) + TX, pp'-DDT (219) + TX , paration (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencaptona (1330) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, fosmet (638) + TX, phosphamidon (639) + TX, foxime

(642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX , promacil (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX , pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridafention (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, quinalfos (711) + TX , quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, escradano (1389) + TX, sebufos (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, sulfotep (753) + TX, sulf ofre (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpirade (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinfos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, tiafenox (alternative name) + TX, thiocarboxime (1431) + TX, tiofanox (800) + TX, thiometon (801) + TX, thioquinox (1436) + TX, thuringian (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, triphenophos (1455) + TX, trinactin

(alternative name) (653) + TX, vamidotion (847) + TX, vaniliprol [CCN] and YI-5302 (compound code) + TX, an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, dioctanoate copper (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutrin [CCN] + TX, diclone (1052) + TX, dichlorophene (232) + TX, endotal (295) + TX, fentine (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) ( 347) and triphenyltin hydroxide (IUPAC name) (347) + TX, an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomato (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [ CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrine (1122) + TX , fention (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (name IUPAC) (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, dodicin (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafene (alternative name) [CCN] + TX, casugamycin (483) + TX, hydrochloride hydrate nickel casugamycin (483) + TX, nickel bis (dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapirin (580) + TX, octyline (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquininosulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, keyboard software (766) + TX, and thiomersal (alternative name) [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani ( alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide ( scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp.

israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri ( alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (name (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 (made available by Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA and known under the trade name Taegro®) + TX, a soil sterilizer selected from the group of substances consisting of iodomethane (IUPAC name) ( 542) and methyl bromide (537) + TX, a chemosterilizer selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methotepa [CCN] + TX, methyl afolate [ CCN] + TX, morzide [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thioempa (alternative name) [CCN] + TX, tiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

an insect pheromone selected from the group of substances consisting of (E) -dec-5-en-1-yl acetate with (E) -dec-5-en-1-ol (IUPAC name) (222) + TX, (E) - tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E) -6-methyl-hept- 2-en-4-ol (IUPAC name) (541) + TX, (E, Z) acetate - tetradeca-4,10-dien-1-yl (IUPAC name) (779) + TX, (Z) -dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z) - hexadec-11-enal (IUPAC name) (436) + TX, (Z) acetate - hexadec-11-en-1-yl (IUPAC name) (437) + TX, (Z) - hexadec-13-en-11-in-1-yl acetate (IUPAC name) (438) + TX, (Z) -icos- 13-en-10-one (IUPAC name) (448) + TX, (Z) -tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z) -tetradec-9-en-1-ol (IUPAC name) (783) + TX, acetate (Z) -tetradec-9-en-1-yl (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) acetate - tetradeca-9,12-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, brevicomine ( alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemona (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, acetate dodec-8-en-1-yl (IUPAC name) (286) + TX, dodec-9-en-1-yl (IUPAC name) acetate (287) + TX, dodeca-8 + TX, 10 acetate -dien-1-ila (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name)

[CCN] + TX, front (alternative name) [CCN] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II ( alternative name) (421) + TX, grandlure III (alternative name) (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, methylphenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca acetate-2.13 -dien-1-ila (IUPAC name) (588) + TX, octadeca-3,13-dien-1-ila acetate (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, s ulcatol (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, a repellent of insects selected from the group of substances consisting of 2- (octyllium) ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate

(IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, phthalate dimethyl [CCN] + TX, ethylhexanediol (1137) + TX, hexamide [CCN] + TX, methoxy-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] + picaridin [CCN] + TX , an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC / Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis (4-ethylphenyl) ethane (name IUPAC) (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, methylphosphate 2,2-dichlorovinyl and 2-ethylsulfinylethyl (IUPAC name) (1066) + TX, 2- (1,3-dithiolan-2-yl) phenyl (IUPAC / Chemical Abstracts name) dimethylcarbamate (1109) + TX, 2- (2-butoxyethoxy) ethyl thiocyanate (IUPAC / Chemical Abstracts name) (935) + TX, 2- (4,5-dimethyl-1,3-dioxolan-2-yl) phenyl methylcarbamate (IUPAC name / Chemical Abstracts) (1084) + TX, 2- (4-chloro-3,5-xylyloxy) ethanol (IUPAC name) (986) + TX, 2-chlorovinyladiethyl phosphate (IUPAC name) (984) + TX, 2 - imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindane- 1,3-dione (IUPAC name) (1246) + TX, 2-methyl (prop-2-inyl) aminophenyl methylcarbamate (IUPAC name) (1284 ) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-

bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl (prop- 2- inyl) amino-3,5-xylyl (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin ( 1) + TX, Acephate (2) + TX, Acetamipride (4) + TX, Acetion (alternative name) [CCN] + TX, Acetoprol [CCN] + TX, Acrinatrin (9) + TX, Acrylonitrile (IUPAC name) ( 861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, aldrin (864) + TX, aletrine (17) + TX, alosamidine (alternative name) [CCN] + TX , alixicarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidition (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amitone hydrogenoxalate (875) + TX, amitraz (24) + TX, anabasin (877) + TX, atidation (883) + TX, AVI 382 ( compound code) + TX, AZ 60541 (compound code) + TX, azadiractin (alternative name) (41) + TX, azametiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, nitrogen (889) + TX, Bacillus delta endotoxins thuringiensis (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC / Chemical Abstracts name) (892) + TX, bartrine [CCN] + TX, Bayer 22 / 190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (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, bioethanometrine [CCN] + TX, biopermetrin (908) + TX, bioresmethrin (80) + TX, bis (2-chloroethyl) ether (IUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (name alternative) + TX, bromfenvinfos (914) + TX, bromocyclene (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb ( 924) + TX, buprofezina (99) + TX, butacarb (926) + TX, butatiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxin (104) + TX, butylpyridabene (name alternative) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, canfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / Chemical Abstracts name) (945) + TX, t carbon etrachloride (IUPAC name) (946) + TX, carbofenotion (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725 ) + TX, chlorobicyclene (960) + TX, chlorodane (128) + TX, chlorodecone (963) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorfenapyr ( 130) + TX, chlorofenvinfos (131) + TX, chlorfluazuron (132) + TX, chlorephes (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfox (989) + TX, chloroprazophos (990 ) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX,

chlortiofos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, cis-resmethrin (alternative name) + TX, schismethrin (80 ) + TX, clocitrine (alternative name) + TX, cloetocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [ CCN] + TX, copper oleate [CCN] + TX, coumafos (174) + TX, coumitoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (1010) + TX, crufomato (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanophenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cyclethrin [ CCN] + TX, cycloprotrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cytoate (name alternative) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX , dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037 ) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton -S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialiphos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapton (1050) + TX, diclofention (1051) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicresil (alternative name) [CCN] + TX, dicrotofos (243) + TX, dicyclanil

(244) + TX, dieldrin (1070) + TX, 5-methylpyrazol-3-yl diethyl phosphate (IUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX , dimeflutrin [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, diophenolane (1099) + TX , dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxation (1102) + TX, disulfotone (278) + TX, dichrophos (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, empentrine (292) + TX, endosulfan (294) + TX, endotion (1121) + TX, endrine (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epophenonane (1124 ) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etafos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, etion (309) + TX, etiprol (310 ) + TX, etoate-methyl (1134) + TX, etoprofos (312) + TX, ethyl format (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, etrimphos (1142) + TX, EXD (1143) + TX, famfur ( 323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, phenlorafos (1148) + TX, fenetacarb (1149) + TX, fenflutrina (1150) + TX, fenitrotion

(335) + TX, phenobucarb (336) + TX, phenoxacrim (1153) + TX, phenoxycarb (340) + TX, phenpiritrin (1155) + TX, fenpropatrin (342) + TX, fenpirad (alternative name) + TX, fensulfotion (1158) + TX, fention (346) + TX, fention-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendiamide (Reg.

CAS.

No.: 272451- 65-7) + TX, flucofuron (1168) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenerin [CCN] + TX, flufenoxuron ( 370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, phosmethylane (1194) + TX, phospirate (1195) + TX, fostiazate (408) + TX, fostietane (1196) ) + TX, furatiocarb (412) + TX, furetrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX , heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquin carb (1223) + TX, imidacloprid (458) + TX, imiprotrine (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, isofenfos (1236) + TX, isolane

(1237) + TX, isoprocarb (472) + TX, O- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, isoprotiolan (474) + TX, isothioate (1244) + TX, isoxation (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmine I (696) + TX, jasmine II (696) + TX, jodfenfos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, hormone juvenile II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevane (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, arsenate lead [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimphos (1251) + TX, lufenuron (490) + TX, litidation (1253) + TX, methylcarbamate m-cumenyl (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malation (492) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbam ( 502) + TX, mecarfon (1258) + TX, menazon (1260) + TX, mefosfolane (1261) + TX, mercury chloride (513) + TX, mosulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, metacryphs (1266) + TX, metamidophos (527) + TX, methanesulfonyl fluoride (IUPAC / Chemical Abstracts name) (1268) + TX, metidation (529) + TX, metiocarb (530) + TX, metocrotophos (1273) + TX, methyl (531) + TX, methoprene (532 ) + TX, methoxy-butyl (1276) + TX, methotrine (alternative name) (533) + TX, methoxychloride (534) + TX, methoxyphenidide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX,

metoflutrin [CCN] + TX, metolcarb (550) + TX, methoxyzone (1288) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN ] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphotion (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, nitenpiram (579) + TX, nitiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb complex and chloride zinc 1: 1 (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, O-5- dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, O phosphorothioate, O-diet il-O-4-methyl-2-oxo-2H-chromen-7-yl (IUPAC name) (1074) + TX, O phosphorothioate, O-diethyl-O-6-methyl-2-propylpyrimidin-4-yl (IUPAC name) (1075) + TX, O, O, O´ dithiopyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxidemeton-methyl (609) + TX, oxideprofos (1324) + TX, oxisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX , paration (615) + TX, paration-methyl (616) + TX, penfluron (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, fencaptona (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, fosmet (638) + TX, fosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (IUPAC name) ( 640) + TX, foxim (642) + TX, foxim-methyl (1340) + TX, pyrimetafos (1344) + TX, pirimicarb (651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorinated dicyclopentadiene isomers (IUPAC name) (1346) + TX, polychlorinated terpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidofos (1349) + TX, profenofos (662) + TX, proflutrin [CCN] + TX, promacil (1354) + TX, promecarb (1355) + TX, propafos (1356) + TX, propetanfos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protiofos (686) + TX, protoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, piraclofos (689) + TX, pyrazophos (693) + TX , pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridine (700) + TX, pyridafention (701) + TX, pyrimidiphene (706) + TX, pyrimitate (1370) + TX, pyriproxyphene (708) + TX, kassia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfos-methyl (1376) + TX, quinotion (1380) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX,

rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX , riânia (alternative name) (1387) + TX, rianodina (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradano (1389) + TX, sebufos (alternative name) + TX, selamectina (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 name Abstracts) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sofamide ( 1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramat (CCN) + TX, s ulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils ( alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpirade (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, teflutrin (769) + TX, temefos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinfos (777) + TX, tetramethrin (787) + TX, tit

cypermethrin (204) + TX, thiaclopride (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800) + TX, thiometon (801) + TX, thionazine (1434) + TX, tiossultap (803) + TX, thiossultap-sodium ( 803) + TX, turingiensin (alternative name) [CCN] + TX, tolfenpirade (809) + TX, tralometrine (812) + TX, transflutrin (813) + TX, transpermetrin (1440) + TX, triamphos (1441) + TX , triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, triphenofos (1455) + TX, triflumuron (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidotion (847) + TX, vaniliprol [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994 -63-19] + TX, chlorantraniliprol [500008-45-7] + TX, cyienopyraphene [560121-52-0] + TX, cyflumetophen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, espinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0] + TX, meperflutrin [915288-13-0] + TX, tetramethylflutrin

[84937-88-2] + TX, triflumezopyrima (disclosed in WO 2012/092115) + TX, a molluscicide selected from the group of substances consisting of bis (tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN ] + TX, calcium arsenate [CCN] + TX, cloetocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name ) (352) + TX, metaldehyde (518) + TX, metiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, tiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprol [394730- 71-3] + TX, a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo -3-chloropropane (IUPAC / Chemical Abstracts name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts name) (1065) + TX, 3- (4-chlorophenyl) -5-methylrodanine (IUPAC name) (980) + TX, 5-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, aldoxicarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrina (141) + TX, chlorpyrifos (145) + TX, cloetocarb (999 ) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, diclofention (1051) + TX, diclifos (alternative name) + TX, dimetoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, etoprofos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpirad (alternative name) + TX, fensulfotion (1158) + TX, fostiazate (408) + TX, fostietano ( 1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + T X, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarfon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, composition of Myrothecium verrucaria (alternative name) (565) + TX, NC-184 (compound code) + TX , oxamil (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosfocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad ( 737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422) + TX, tiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compost code o) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethyl xanthate [CCN] and nitrapirin (580) + TX, a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX, a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, alpha- hydrochlorine [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenious oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX, brodifacoum (89 ) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumaclor (1004) + TX, coumafurila (1005) + TX, coumatetralila (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difetialona (249) + TX, difacinone (273) + TX, ergocalciferol

(301) + TX, flocoumafene (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX , norbormide (1318) + TX, fosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindona (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, esciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX, a synergist selected from the group of substances consisting of 2- (2-butoxyethoxy) ethyl piperonylate (IUPAC name) (934) + TX, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolina (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose ( 127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatin (422) + TX, acetates guazatin (422) + TX, metiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, strip (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a wound protector selected from the group of substances consisting of mercuric oxide ( 512) + TX, octylinone (5 90) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of ametoctradine [865318-97-4] + TX, amisulfon [348635-87-0] + TX, azaconazole [60207-31-0 ] + TX, benzovindiflupir [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, diphenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [238410-11-2] + 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, fluxpyroxad [907204-31-3] + 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, Isotian ila [224049-04-1] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures described in WO 2010/093059) + TX,

mefentrifluconazole [1417782-03-6] + TX, metconazole [125116- 23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30- 4] + TX, penflufen [494793-67-8] + TX, penconazole [66246-88-6] + TX, protioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534- 96-3] + TX, tetraconazole [112281-77-3 ] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancimidol [ 12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethyrimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemorf [1593-77-7] + TX, phenpropidine [67306-00-7] + TX, fenpropimorf [67564-91-4] + TX, spiroxamine [118134 -30- 8] + TX, tridemorf [81412-43-3] + TX, cyprodinil [121552- 61-2] + TX, mepanipirim [110235-47-7] + TX, pyrimethanil [53112-28-0] +TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, fluindapyr [1383809-87-7] + TX, benalaxyl [71626-11-4] + TX, furalaxila [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, benomile [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148 -79-8] + TX, clozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, boscalide [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, oxycarboxine [5259-88-1] + TX, pentiopirad [183675-82-3] + TX, tifluzamide [130000- 40-7] + TX, guazatin [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, cresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orisastrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, piraoxystrobin [862588-11-2 ] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, entered [9006-42-2] + TX, propineb [ 12071-83-9] + TX, remove [137-26-8] + TX, zineb [12122-67-7] + TX, remove [137-30-4] + TX, captafol [2425-06- 1] + TX, captana [133-06-2] + TX, dichlofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, leaflet [133-07-3] + TX, tolylfluanide [731 -27-1] + TX, bordeaux mixture [8011- 63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317-39-1] + TX, maneuver [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131 -72-6] + TX, nitrotal-isopropyl [10552-74-6] + TX, buildings [17109- 49-8] + TX, iprobenfos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457- 18-6] + TX, tolclofos-methyl [57018-04-9] + TX,

acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [57966-95- 7] + TX, diclone [117-80-6] + TX, diclocimet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, dietofencarb [87130-20-9] + TX, dimetomorf [110488-70-5] + TX, SYP-LI90 (Flumorf) [211867-47-9] + TX, dithianon [3347- 22-6] + TX, etaboxam [ 162650-77-3] + TX, etridiazole [2593-15-15] + TX, famoxadone [131807-57-3] + TX, phenamidone [161326-34-7] + TX, phenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferinzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolid [239110-15-7] + TX, flussulfamide [106917 -52-6] + TX, phenhexamide [126833-17- 8] + TX, phosethyl aluminum [39148-24-8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17 -7] + TX, IKF-916 (Cyzofamide) [12011 6-88-3] + TX, casugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencicuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [11113- 80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606 - 41-1] + TX, proquinazide [189278-12-4] + TX, pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyroquinone [57369-32-1] + TX, pyrophenone [688046-61-9] + TX, pyribencarb [799247-52-2] + TX, pyrisoxazole [847749-37- 5] + TX, quinoxifene [124495-18-7] + TX, quintozene [82- 68- 8] + TX, sulfur [7704-34-9] + TX, Timorex GoldTM (plant extract containing tea tree oil from the Stockton Group) + TX, tebufloquine [376645-78-2] + TX, thiadinyl [ 223580-51- 6] + TX, triazoxide [72459-58-6] + TX, tolprocarb [911499- 62-2] + TX, triclopyricarb [902760-40-1] + TX, tricyclazole [41814-78-2] + TX, triforin [26644-46-2] + TX, validamycin [37248-47-8] + TX, valiphenalate [283159-90-0] + TX, zoxami da (RH7281) [156052-68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, phenamacryl + TX, silkxane [874967-67-6] + TX , trinexapac-ethyl [95266-40-3] + TX, 3-difluoromethyl acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl) -amide -1-methyl-1H-pyrazole-4-carboxylic (disclosed in WO 2007/048556) + TX, (3´, 4´, 5´-trifluoro-biphenyl-2-yl) -amide of 3-difluoromethyl-1 acid - methyl-1H-pyrazolo-4-carboxylic (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, 11Hnafto [2,1-b] pyran [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-pyrazole-4- carboxamide [926914-55-8] + TX. or a biologically active compound selected from the group consisting of N - [(5-chloro-2-isopropyl-phenyl) methyl] - N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6- Dimethyl-1H, 5H- [1,4] dithionine [2,3-c: 5,6-c ' ] dipirrol-

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-pyrrole [4,5] [ 1,4] dithiine [1,2-c] isothiazole-3-carbonitrile + TX, 4- (2-bromo-4-fluoro-phenyl) -N- (2-chloro-6-fluoro-phenyl) - 2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedures described in WO 2012/031061) + TX, 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl -indan-4-yl) -1-methyl-pyrazolo-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 1,1-dioxide 3- (3,4-dichloro-1,2-thiazol-5-ylmethoxy) -1,2-benzothiazole (can be prepared according to the procedures described in WO 2007/129454) + TX, 2- [2- [(2,5-dimethylphenoxy) methyl] phenyl] -2-methoxy-N-methyl-acetamide + TX, 3- (4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1- il) 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] propa n-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, 2- [2 - [(7,8-difluoro-2-methyl-3-quinolyl) oxy] -6- fluoro-phenyl] propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, oxatiapiproline + TX [1003318-67-9], N- [6 - [[[(1- methylthetrazol-5-yl) -phenyl-methylene] amino] oxymethyl] -2-pyridyl] tert-butyl 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] pyrazolo-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX , N- [2-methyl-1 - [[((4-methylbenzoyl) amino] methyl] propyl] 2,2,2-trifluoroethyl 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- methanesulfonate dihydroisoxazol-5-yl] -3-chloro-f enyl] (can be prepared according to the procedures described in WO 2012/025557) + TX, N- [6 - [[(Z) - [(1-methyltetrazol-5-yl) - phenyl-methylene] amino] oxymethyl ] -2-pyridyl] but-3-inyl 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-triazolo-3-thione (can be prepared according to the procedures described in WO 2010/146031) + TX, N - [[5- [4- (2,4-dimethylphenyl) triazol-2-yl] -2-methyl-phenyl] methyl] 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-triazole- 1-yl) propan-2-ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenyl- pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4- (2,6-difluorophenyl) -6-methyl-5-phenyl-pyridazine-3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774) + TX, (R) -3- (difluoromethyl) -1-methyl-N- [1,1,3-trimethylindan-4-yl] pyrazolo-4-carboxamide (can be prepared according to the procedures described in the document in WO 2011/162397) + TX, 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-indan-4-yl) -1-methyl-pyrazole -4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1- [2 - [[1- (4-chlorophenyl) pyrazol-3-yl] oxymethyl] -3-methyl- phenyl] -4-methyl-tetrazole- 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-methylpyrazolo-4-carboxamide [1255734-28-1] (can be prepared according to the procedures described in WO

2010/130767) + TX, 3- (difluoromethyl) -N - [(R) -2,3-dihydro- 1,1,3-trimethyl-1H-inden-4-yl] -1-methylpyrazolo-4 -carboxamide [1352994-67-2] + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N- ethyl-N-methyl-formamidine + TX, N' - [4- (4, 5-dichloro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N -ethyl-N-methyl-formamidine + TX, N '- [4- (4,5-dichloro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX,

(phenpicoxamide [517875-34-2] (as described in WO 2003/035617)) + TX, N - {[3- (acetyloxy) -4-methoxy-2-pyridyl] carbonyl} -L-alaninate (1S ) -2,2-bis (4-fluorophenyl) -1-methylethyl [1961312-55-9] (as described in WO 2016/122802) + TX, 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.

[0141] References in square brackets behind the active ingredients, for example [3878-19-1] refer to the Chemical Abstracts Registration Number. The mixing partners described above are known. When the 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 under the entry number given in curly brackets above above for the particular compound; for example, the compound "abamectin" is described under the entry number (1). When added above in this document "[CCN]" to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible over the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprol" is described at http://www.alanwood.net/pesticides/acetoprole.html.

[0142] Most of the active ingredients described above are referred to here above by a so-called “common name”, with the relevant “common name ISO” or another “common name” used in individual cases. If the designation is not a “common name”, the nature of the designation used instead is provided in curly brackets for the particular compound; in that case the IUPAC name, the IUPAC / Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” are used or, if neither of these designations is used nor a “common name”, an “alternative name” is used. “Reg. CAS No. ”means the Chemical Abstracts Registration Number.

[0143] The mixture of active ingredients of the compounds of formula (I) selected from a compound represented in Tables 1.1 to 1.11, Tables 2.1 to 2.10, or the compounds 1.1 to 1.6 according to the invention listed in Table T1 (below), it is 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 between 5: 1 and 1: 5, with a special preference being given to a ratio of 2: 1 to 1: 2, and equally being preferred a ratio of 4: 1 to 2: 1, above all in a ratio of 1: 1, or 5: 1, or 5: 2, or 5: 3, or 5: 4, or 4: 1, or 4: 2, or 4: 3, or 3: 1, or 3: 2, or 2: 1, or 1: 5, or 2: 5, or 3: 5, or 4: 5, or 1: 4, or 2: 4, or 3: 4, or 1: 3, or 2: 3, or 1: 2, or 1: 600, or 1: 300, or 1: 150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1: 6000, or 1: 3000, or 1: 1500, or 1: 350, or 2: 350, or 4: 350, or 1: 750, or 2: 750, or 4: 750. These mixing ratios are by weight.

[0144] Mixtures as described above can be used in a method for pest control, which comprises applying a composition comprising a mixture as described above to pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

[0145] Mixtures comprising a compound represented in Tables 1.1 to 1.11, Tables 2.1 to 2.10, or compounds 1.1 to 1.6 according to the invention listed in Table T1 (below), and one or more active ingredients as described above can be applied, for example, in a simple “ready mix” form, in a combined spray mix, composed of separate formulations of the components of the isolated active ingredients, such as a “tank mix”, and in a combined use of the active ingredients when applied sequentially, that is, one after the other, in a reasonably short period, such as a few hours or days. The order of application of a compound represented in Tables 1.1 to 1.11, Tables 2.1 to

2.10, or the compounds 1.1 to 1.6 according to the invention listed in Table T1 (below), and the active ingredient (s) described above, is not essential for the practice of the present invention.

[0146] 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 soy oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0147] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example, by grinding, sieving and / or compression of a solid active ingredient and in the presence of at least one auxiliary, for example, by intimate mixing and / or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of compounds (I) for the preparation of these compositions are also a subject of the invention.

[0148] Another aspect of the invention relates to the use of a compound of the formula (I) or of a preferred individual compound as defined herein, of a composition comprising at least one compound of the formula (I) or at least one compound preferred individual as defined above, or a fungicidal or insecticidal mixture comprising at least one compound of the formula (I) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as described above, for control or preventing plant infestation, for example, useful plants, such as crop plants, their propagating material, for example, seeds, collected cultures, for example, collected food crops or non-living materials by insects or phytopathogenic microorganisms, preferably organisms fungal.

[0149] An additional aspect of the invention relates to a method for controlling or preventing an infestation of plants, for example, useful plants, such as crop plants, propagating material, for example, seeds, harvested crops, for example, harvested food crops, or non-living materials by insects or phytopathogens or spoilage micro-organisms or organisms potentially harmful to humans, especially fungal organisms, comprising the application of a compound of formula (I) or a preferred individual compound as defined above as an active ingredient for plants, parts of plants or their locus, propagating material for them, or any part of non-living materials.

[0150] Control or prevention means reducing infestation by phytopathogenic microorganisms or that cause deterioration or organisms that are potentially harmful to man, especially fungal organisms, to such an extent that an improvement is demonstrated.

[0151] A preferred method of controlling or preventing the infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects that comprise the application of a compound of the formula (I), or an agrochemical composition that contains at least one of the aforementioned compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I)

they can also penetrate the plant through the roots through the soil (systemic action), by soaking the plant's locus with a liquid formulation or by applying the compounds in the solid form in the soil, for example, in the granular form (application in 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.

[0152] A formulation, for example a composition containing the compound of the formula (I) and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of the formula (I) can be prepared in a known manner, typically by mixing intimate and / or grinding of the compound with diluents, for example solvents, solid carriers and, optionally, surfactant compounds (surfactants).

[0153] Advantageous application rates usually range from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, more preferably from 20 g to 600 g a.i./ha. When used as a seed drenching agent, convenient dosages range from 10mg to 1g of active substance per kg of seeds.

[0154] 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 seeds, preferably 0.01 to 10 g per kg of seeds, are generally sufficient .

[0155] Suitably, a composition comprising a compound of formula (I) according to the present invention is applied preventively, meaning before disease development, or curatively, meaning after disease development.

[0156] The compositions of the invention can be used in any conventional form, for example in the form of a double pack, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a concentrate suitable for flow for seed treatment (FS), a seed treatment solution (LS), a water-dispersible powder for seed treatment (WS), a suspension of seed treatment capsules (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a microemulsion (ME), an oil dispersion (OD), an oil miscible fluid (OF), an oil miscible liquid (OL ), a 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 technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0157] Such compositions can be produced in a conventional manner, for example by mixing the active ingredients with appropriate formulation aggregates (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, antifreeze, adhesives, thickeners and compounds that provide adjuvant effects). Conventional slow release formulations can also be employed where long-term efficacy is desired. In particular, formulations to be applied to spray forms, such as water-dispersible concentrates (eg EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as agents wetting and dispersing agents, and other compounds that provide adjuvant effects, for example the condensation product of formaldehyde with naphthalenesulfonate, an alkylarylsulfonate, a lignin sulfonate, an ethoxylated alkyl grease and alkylphenol sulfate and an ethoxylated fatty alcohol.

[0158] A seed coating formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in the form of a suitable seed covering formulation, for example, as an aqueous suspension or in a form of dry powder with good adhesion to the seeds. Such formulations for seed curing are known in the art. Seed-curing formulations can contain the individual active ingredients or the combination of active ingredients in encapsulated form, for example as slow-release capsules or microcapsules.

[0159] In general, the 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 inert formulation agents and adjuvant (s) ) wherein the active agent consists of at least the compound of formula (I) optionally in conjunction with other active agents, particularly microbiocides or preservatives or the like. Concentrated forms of compositions generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Forms of application of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of active agent. While commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

[0160] Although it is preferable to formulate commercial products as concentrates, the end user will normally use diluted formulations.

[0161] Table 1.1: This table discloses 29 specific compounds of the formula (T-1): (T-1) where A is:

R1 and R2 are hydrogen, R3 is methoxy, and Z is as defined below in Table 1.

[0162] Each of Tables 1.2 to 1.11 (which follows Table 1.1) makes available 29 individual compounds of formula (T-1) in which A, R1, R2 and R3 are as specifically defined in Tables 1.2 to 1.11, which refer to Table 1, where Z is specifically defined. Table 1 Compound Compound

Z Z no. cyclopropyl tetrahydrofuran-3-

1,001 1,016 ila 1-chlorocycloprop-1-N-3-oxo-

1,002 1,017 ila pyrrolidinyl 1-cyanocycloprop-1- N-pyrrolidinyl

1,003 1,018 ila 1-fluorocycloprop- N-2-oxo-

1,004 1,019 1-yl pyrrolidinyl 1-methylcycloprop-1- N-azetidinyl

1,005 1,020 ila 1- N-iso-oxazolidinyl

1,006 trifluoromethylcyclo 1,021 prop-1-yl 1-hydroxycycloprop- N-oxazolidinyl

1,007 1,022 1-line

1-methoxycycloprop- N-morpholinyl

1,008 1,023 1-yl 2,2- N-oxazinanyl

1,009 dichlorocycloprop-1- 1,024 ila 2,2- N-1-methoxypiperazin-

1,010 difluorocycloprop- 1,025 4-yl 1-yl 2,2- N-1-methylpiperazin-

1,011 dimethylcycloprop-1- 1,026 4-yl cyclobutyl ethanone of N-1-

1,012 1,027 piperazin-4-ila

1,013 cyclopentyl 1,028 N-piperidinyl

1,014 cyclohexyl 1,029 N-2-oxo-piperidinyl tetrahydrofuran-2-

1,015 ila

[0163] Table 1.2: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is methoxy, and Z is as defined above in Table 1.

[0164] Table 1.3: This table discloses 29 specific compounds of the formula (T-1) where A is:

R1 and R2 are hydrogen, R3 is methoxy, and Z is as defined above in Table 1.

[0165] Table 1.4: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is methoxy, and Z is as defined above in Table 1.

[0166] Table 1.5: This table discloses 29 specific compounds of the formula (T-1) where A is: and R1 and R2 are hydrogen, R3 is methoxy, and Z is as defined above in Table 1.

[0167] Table 1.6: This table discloses 29 specific compounds of the formula (T-1) where A is: and R1 is hydrogen, R2 is methyl and R3 is methoxy, and Z is as defined above in Table 1.

[0168] Table 1.7: This table discloses 29 specific compounds of the formula (T-1) where A is: and R1 is hydrogen, R2 is methyl and R3 is methoxy, and Z is as defined above in Table 1.

[0169] Table 1.8: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is 2,2-difluoroethoxy, and Z is as defined above in Table 1.

[0170] Table 1.9: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is 2,2-difluoroethoxy, and Z is as defined above in Table 1.

[0171] Table 1.10: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is ethoxy, and Z is as defined above in Table 1.

[0172] Table 1.11: This table discloses 29 specific compounds of the formula (T-1) where A is: R1 and R2 are hydrogen, R3 is ethoxy, and Z is as defined above in Table 1.

[0173] Table 2.1: This table discloses 28 specific compounds of the formula (T-2):

(T-2) where A is: R1 and R2 are hydrogen, and Za is as defined below in Table

two.

[0174] Each of Tables 2.2 to 2.7 (which follow Table 2.1) makes available 28 individual compounds of formula (T-2) in which A, R1, R2 and R3 are as specifically defined in Tables 2.2 to 2.10, which refer to Table 2, where Za is specifically defined. Table 2 Compound Compound Za Za No. 5 - isoxazolidine-3-thione

2,001 (trifluoromethyl) pyrrole 2015 lidina-2-thione 5- 5-oxa-6-

2.002 (difluoromethyl) pyrrole 2,016 azaspiro [2.4] heptane-idine-2-thione 7-thione 3-methylpyrrolidine-2- 1-methoxy-

2,003 2,017 imidazolidine-2-thione 4-methylpyrrolidine-2- 1-methylimidazolidine-

2,004 2,018 thion 2-thion

5-methylpyrrolidine-2- 4-

2,005 thion 2,019 azaspiro [2.5] octane-5-thione pyrrolidine-2-thione 5-

2,006 2,020 azaspiro [2.5] octane- 4-thione

2,007 azetidine-2-thione 2,021 azepano-2-thione 4- 3,3-

2,008 azaspiro [2.4] heptane- 2,022 dimethylpiperidine-2- 5-thionione 5- 6,6-

2,009 azaspiro [2.4] heptane-2,023 dimethylpiperidine-2- 4-thionione 4,4- 1-

2,010 dimethylisoxazolidine- 2,024 methoxyhexahydropyrimi 3-thione dina-2-thione 5,5- 1-

2,011 dimethylisoxazolidine- 2,025 methylhexahydropyrimid 3-thionine-2-thione 3,3-morpholine-3-thione

2,012 dimethylpyrrolidine-2- 2,026 thion 5,5-oxazinan-3-thion

2,013 dimethylpyrrolidine-2- 2,027 thion 5-ethyl-5-methyl-piperidine-2-thione

2,014 2,028 isoxazolidine-3-thione

[0175] Table 2.2: This table discloses 28 specific compounds of the formula (T-2) where A is: R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0176] Table 2.3: This table discloses 28 specific compounds of the formula (T-2) where A is: R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0177] Table 2.4: This table discloses 28 specific compounds of the formula (T-2) where A is: R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0178] Table 2.5: This table discloses 28 specific compounds of the formula (T-2) where A is: and R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0179] Table 2.6: This table discloses 28 specific compounds of the formula (T-2) where A is: and R1 is hydrogen, R2 is methyl and Za is as defined above in Table 2.

[0180] Table 2.7: This table discloses 28 specific compounds of the formula (T-2) where A is: and R1 is hydrogen, R2 is methyl and Za is as defined above in Table 2.

[0181] Table 2.8: This table discloses 28 specific compounds of the formula (T-2) where A is: R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0182] Table 2.9: This table discloses 29 specific compounds of the formula (T-2) where A is: R1 and R2 are hydrogen, and Za is as defined above in Table

two.

[0183] Table 2.10: This table discloses 28 specific compounds of the formula (T-2) where A is:

R1 and R2 are hydrogen, and Za is as defined above in Table

two.

EXAMPLES

[0184] The following Examples serve to illustrate the invention.

[0185] The compounds of the invention can be distinguished from known compounds by virtue of their greater effectiveness at low rates of application, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower rates of application if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0186] The compounds of formula (I) can have any number of benefits including, inter alia, advantageous levels of biological activity to protect plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, increased biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties or increased biodegradability).

[0187] Throughout this description, temperatures are presented in degrees Celsius (° C) and "mp." means melting point. LC / MS stands for Liquid Chromatography coupled to

Mass spectrometry, and the description of the apparatus and method A is as follows: The description of the LC / MS apparatus and method A is: Waters SQ 2 detector Ionization method: Electrospray Polarity: Capillary positive and negative ions (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 / h) 0 , Desolvation Gas Flow (L / h) 650 Mass range: 100 to 900 From DAD wavelength range (nm): 210 to 500 Waters UPLC ACQUITY method with the following HPLC gradient conditions: (Solvent A: Water / Methanol 20: 1 + 0.05% formic acid and Solvent B: Acetonitrile + 0.05% formic acid) Time (minutes) A (%) B (%) Flow rate (mL / min) 0 100 0 0.85 1.2 0 100 0.85 1.5 0 100 0.85

[0188] Column type: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Column internal diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 ° C.

[0189] When necessary, the enantiomerically pure final compounds can be obtained from racemic materials as appropriate via standard physical separation techniques such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg using chiral starting materials. Formulation Examples Wettable powders a) b) c) Active ingredient [composed of 25% 50% 75% formula (I)] sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% diisobutyl naphthalenesulfonate - 6 % 10% sodium phenol polyethylene glycol ether - 2% - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 10% kaolin 62% 27% -

[0190] The active ingredient is carefully mixed with the adjuvants and the mixture is carefully ground in a suitable mill, creating wettable powders that can be diluted with water to provide suspensions of the desired concentration. Powders for seed treatment aa) b) c) dry Active ingredient [composed of 25% 50% 75% formula (I)] light mineral oil 5% 5% 5% highly dispersed silicic acid 5% 5% - kaolin 65% 40 % -

Talc - - 20%

[0191] The active ingredient is carefully mixed with the adjuvants and the mixture is carefully ground in a suitable mill, giving rise to powders that can be used directly for seed treatment. Emulsifiable concentrate active ingredient [compound of the formula 10% (I)] 3% octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 4% mol of oxide ethylene) cyclohexanone 30% xylene mixture 50%

[0192] Emulsions of any required dilution, which can be used to protect plants, can be obtained from this concentrate by dilution with water. Dusts a) b) c) Active ingredient [compound of the formula 5% 6% 4% (I)] Talc 95% - - Kaolin - 94% - mineral filler - - 96%

[0193] Ready-to-use dust is obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed coating.

Extruder granules Active ingredient [compound of 15% formula (I)] 2% sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0194] 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 draft. Coated granules Active ingredient [compound of formula 8 (I)]% polyethylene glycol (mol. 3,200)% Kaolin 89%

[0195] The finely crushed active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. In this way, coated, non-dusty granules are obtained. Suspension concentrate Active ingredient [compound of the formula (I)] 40% propylene glycol 10% polyethylene glycol nonylphenolic ether (15 6 mol% ethylene oxide) Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of an emulsion a 1% 75% in water)

Water 32%

[0196] 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, spilling or immersion. Flowable concentrate for seed treatment Active ingredient [compound of formula (I)] 40% propylene glycol 5% butanol PO / EO copolymer 2% tristyrenophenol with 10-20 moles of 2% EO 1,2-benzisothiazolin-3-one ( in the form of a 0.5% 20% solution in water) 5% monoazo pigment calcium salt Silicone oil (in the form of a 0.2% emulsion 75% in water) 45.3% water

[0197] 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, spilling or immersion.

Suspension of Slow Release Capsules

[0198] 28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate mixture (8: 1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is reached. 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.

[0199] The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The Capsule Suspension Formulation contains 28% of the active ingredients. The average diameter of the capsules is 8-15 microns.

[0200] The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for this purpose. List of Abbreviations: AIBN = azobisisobutyronitrile brs = broad singlet DMF = dimethylformamide DMA = dimethylacetamide DIPEA = N, N-diisopropylethylamine EtOAc = ethyl acetate HCl = hydrochloric acid pf = melting point

° C = degrees Celsius MeOH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide min = minutes ta = room temperature h = hour (s) TFAA = trifluoroacetic acid anhydride THF = tetrahydrofuran Tr = retention time (in minutes) LC / MS = Liquid Chromatography-Mass Spectrometry (description of the apparatus and methods used for LC / MS analysis is provided above) Preparation Examples

[0201] Using the synthetic techniques described both above and below, the compounds of formula (I) can be prepared accordingly. Example 1: This example illustrates an alternative preparation of N-methoxy-N- [1- [5- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] -2-thienyl] ethyl] cyclopropanecarbothioamide ( Compound 1.2 from Table T1) Step 1: Preparation of N-methoxycyclopropanecarboxamide

[0202] To a solution of O-methylhydroxylamine (0.80 g, 21.8 mmol) and potassium carbonate (0.52 mL, 2.88 mmol) in ethyl acetate (7.7 mL) cooled by ice bath medium, cyclopropanecarbonyl chloride (2.0 g, 18.2 mmol) was introduced dropwise over 30 minutes. The ice bath was removed and after the contents had been stirred for 2 hours, EtOH (5 ml) was introduced and the contents were stirred for an additional 30 minutes. The solids were filtered and then dried under vacuum to provide 2.14 g of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 11.13 (s, 1H), 3.57 (s, 3H), 1.34 (m, 1H), 0.87 (m, 1H), 0 , 68 (m, 3H). Step 2: Preparation of N- [1- (5-cyano-2-thienyl) ethyl] -N- methoxy-cyclopropanecarboxamide

[0203] To a solution of N-methoxycyclopropanecarboxamide (0.18 g, 1.02 mmol) in acetonitrile (2 mL) was introduced with lithium hydroxide (0.04 g, 1.85 mmol) followed by 5- (1 -bromoethyl) thiophene-2-carbonitrile (0.2 g, 5.50 mmol). The reaction was heated to 60 ° C for 16 hours, then it was cooled to 25 ° C and quenched with water. The contents were extracted with ethyl acetate and the combined total organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting impure was purified by flash chromatography with silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 7: 3) to give 0.20 g of the title compound as a white solid. mp: 109-112 ° C.

1H NMR (400 MHz, CDCl3) δ ppm: 7.49 (d, 1H), 7.02 (d, 1H), 5.85 (s, 1H), 3.75 (s, 3H), 2.05 (m, 1H), 1.70 (m, 2H), 1.05 (m, 2H), 0.89 (m, 2H). Step 3: Preparation of N- [1- [5- [N'-hydroxycarbamimidoyl] -2-thienyl] ethyl] -N-methoxy-cyclopropanecarboxamide

[0204] To a solution of N- [1- (5-cyano-2-thienyl) ethyl] -N-methoxy-cyclopropanecarboxamide (0.20 g, 0.80 mmol) and EtOH (2.5 mL) was introduced hydroxylamine hydrochloride (0.11 g, 1.60 mmol) and trimethylamine (0.22 mL, 1.60 mmol). The reaction was then heated to 80 ° C for 2 hours, cooled to 25 ° C, and concentrated under reduced pressure and dried under vacuum to provide 0.24 g of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.60 (ls, 1H), 7.30 (d, 1H), 6.95 (d, 1H), 5.87 (s, 2H), 5 , 70 (s, 1H), 3.65 (s, 3H), 2.10 (m, 1H), 1.55 (d, 3H), 0.82 (m, 4H). Step 4: Preparation of N-methoxy-N- [1- [5- [5- (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] -2-thienyl] ethyl] cyclopropanecarboxamide

[0205] To a crude solution of N- [1- [5- [N'-hydroxycarbamimidoyl] -2-thienyl] ethyl] -N-methoxy-cyclopropanecarboxamide (0.80 mmol) in tetrahydrofuran (2.4 ml) cooled via an ice bath, trifluoroacetic anhydride (0.17 ml, 1.20 mmol) was added. The reaction mixture was stirred at 25 ° C overnight and then diluted with saturated NaHCO3, extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography on silica gel (eluent gradient cyclohexane: EtOAc 99: 1 to 7: 3) to provide 0.24 g of the title compound as a white amorphous solid. LC / MS (Method A) retention time = 1.13 minutes, mass charge not detected. 1H NMR (400 MHz, CDCl3) δ ppm: 7.76 (d, 1H), 7.09 (d, 1H), 5.95 (s, 1H), 3.75 (s, 3H), 2.10 (m, 1H), 1.70 (m, 3H), 1.05 (m, 2H), 0.85 (m, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.36 (s). Step 5: Preparation of N-methoxy-N- [1- [5- [5- (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] -2-thienyl] ethyl] cyclopropanecarbothioamide

[0206] To a solution of N-methoxy-N- [1- [5- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] -2-thienyl] ethyl] cyclopropanecarboxamide (0.090 g, 0.27 mmol) in toluene (1 mL), phosphorus pentasulfide (0.07 g, 0.31 mmol) was introduced and the reaction was heated to reflux.

After 4 hours, the content was allowed to reach 25 ° C, then poured into a mixture of water and ethyl acetate.

The layers were separated, the organic layer was dried over sodium sulfate, concentrated under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (gradient eluent cyclohexane / EtOAc 1: 0 to 6: 4) to give 0.04 g of the title compound as a yellow gum.

LC / MS (Method A) retention time = 1.22 minutes, 378 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 7.76 (d, 1H), 7.25 (d, 1H), 3.75 (s, 3H), 2.55 (m, 1H), 1.80 (m, 3H), 1.70 (m, 1H), 1.55 (m, 1H), 1.35 (m, 1H), 1.05 (m, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.36 (s). Example 2: This example illustrates the preparation of 1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] piperidine-2-thione (Compound 1.5 from Table T1)

Step 1: Preparation of 4 - [(2-oxo-1-piperidyl) methyl] benzonitrile

[0207] A solution of 4- (bromomethyl) benzonitrile (2.0 g, 10.2 mmol), piperidin-2-one (1.04 g, 10.5 mmol), and potassium carbonate (1.41 g , 10.2 mmol) in acetonitrile (20 mL) was heated to 85 ° C for 20 hours. After cooling to 25 ° C, the solvent was removed under reduced pressure and the residue obtained was dissolved in ethyl acetate and washed with water. The organic layer was then dried over sodium sulfate and concentrated under reduced pressure. The crude yellow residue obtained was purified by flash chromatography on silica gel (eluent gradient cyclohexane: EtOAc 9: 1 to 0: 1) to provide 0.28 g of the title compound as a yellow oil. LC / MS (Method A) retention time = 0.71 minutes, 215 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 7.62 (d, 2H), 7.36 (d, 2H), 4.64 (s, 2H), 3.22 (m, 2H), 2.49 (t, 2H), 1.82 (m, 4H). Step 2: Preparation of N-hydroxy-4 [(2-oxo-1-piperidyl) methyl] benzamidine

[0208] To a heterogeneous solution of hydroxylamine hydrochloride (0.27 g 3.9 mmol) and ethanol (33 mL) was added triethylamine (0.55 mL, 3.92 mmol) at 25 ° C. The resulting suspension was allowed to stir for 30 minutes after which 4 - [(2-oxo-1-piperidyl) methyl] benzonitrile (0.28 g, 1.31 mmol) was introduced and the reaction mixture heated to a temperature of 50 ° C for 18 hours. The volatiles were removed under reduced pressure and the crude reaction mixture resumed in the next step without further purification or characterization. LC / MS (Method A) retention time = 0.24 minutes, 248 (M + H). Step 3: Preparation of 4 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] morpholin-3-one

[0209] To a crude N-hydroxy-4 - [(2-oxo-1-piperidyl) methyl] benzamidine (320 mg, 1.29 mmol) in tetrahydrofuran (2 mL) was added dropwise trifluoroacetic anhydride (0.27 mL, 1.94 mmol) at 25 ° C. After stirring overnight, the solvent was removed under reduced pressure, giving rise to an orange oil which was dissolved in a minimal amount of dichloromethane and then washed with a saturated aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate, filtered, and the volatiles were removed under reduced pressure. The crude residue was purified by combiflash chromatography on silica gel (cyclohexane eluent gradient: EtOAc 99: 1 to 9: 1) to give 265 mg of the title compound as a clear oil, which solidified at 4 ° C. mp: 31 - -34 ° C. LC / MS (Method A) retention time = 0.99 minutes, 326 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.07 (d, 2H), 7.41 (d, 2H), 4.68 (s, 2H), 3.24 (m, 2H), 2.50 (m, 2H), 1.83 (m, 4H).

19F NMR (400 MHz, CDCl3) δ ppm: -65.34 (s). Step 4: Preparation of 1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] piperidine-2-thione

[0210] To a suspension of 4 - [[4- [5- (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] morpholin-3-one (0.10 g, 0.31 mmol) in toluene (1 mL), phosphorus pentasulfide (0.075 g, 0.34 mmol) was introduced and the reaction was heated to reflux. After 2 hours, the content was allowed to reach 25 ° C, then poured into a mixture of water and ethyl acetate. The layers were separated, the organic layer was dried over sodium sulfate, concentrated under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 1: 1) to provide 0.09 g of the title compound as a yellow solid. mp 92-95 ° C. LC / MS (Method A) retention time = 1.11 minutes, 342 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.10 (d, 2H), 7.50 (d, 2H), 5.42 (s, 2H), 3.42 (m, 2H), 3.15 (m, 2H), 1.91 (m, 2H), 1.80 (m, 2H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.34 (s). Example 3: This example illustrates the preparation of 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-thione ( Compound 1.6 from Table T1).

Step 1: Preparation of 4 - [(5,5-dimethyl-3-oxo-isoxazolidin-2-yl) methyl] benzonitrile

[0211] To a solution of 5,5-dimethylisoxazolidin-3-one (1.00 g, 8.7 mmol) in dimethylacetamide (5 mL) was added sodium carbonate (0.84 g, 7.8 mmol), water (5 ml) and 4- (bromomethyl) benzonitrile (1.8 g, 9.1 mmol). The contents were then heated to 85 ° C for 3.5 hours. After cooling to 25 ° C, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was then dried over sodium sulfate and concentrated under reduced pressure to give 1.75 g of the title compound. LC / MS (Method A) retention time = 0.80 minutes, 231 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 7.64 (d, 2H), 7.42 (d, 2H), 4.73 (s, 2H), 2.64 (m, 2H), 1.26 (s, 6H). Step 2: Preparation of 4 - [(5,5-dimethyl-3-oxo-isoxazolidin-2-yl) methyl] -N-hydroxy-benzamidine

[0212] To a heterogeneous solution of hydroxylamine hydrochloride (0.36 g 5.21 mmol) and ethanol (5 mL) was added triethylamine (0.53 mL, 5.21 mmol) at 25 ° C. The resulting suspension was allowed to stir for 30 minutes after which 4 - [(5,5-dimethyl-3-oxo-isoxazolidin-2-yl) methyl] benzonitrile (1.00 g, 4.34 mmol) was introduced and the reaction mixture heated to 50 ° C for 6 hours. The volatiles were removed under reduced pressure and the crude reaction mixture was taken up in the next step without further purification or characterization. LC / MS (Method A) retention time = 0.27 minutes, 264 (M + H). Step 3: Preparation of 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-one

[0213] To a solution of crude 4 - [(5,5-dimethyl-3-oxo-isoxazolidin-2-yl) methyl] -N-hydroxy-benzamidine (1.0 g, 3.61 mmol) in acetate of ethyl (20 ml) pyridine (0.44 ml, 5.41 mmol) was added at 25 ° C. After 10 minutes, CF3COCl gas (0.530 g, 3.97 mmol) was added via gentle bubbling. After 2 hours, the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered, and the volatiles were removed under reduced pressure. The crude residue was purified by combiflash chromatography on silica gel (eluent gradient cyclohexane: EtOAc 99: 1 to 9: 1) to give 1.27 g of the title compound as a clear oil which solidified during storage. mp: 51 - -54 ° C. LC / MS (Method A) retention time = 1.04 minutes, 342 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.14 (d, 2H), 7.55 (d, 2H), 5.23 (s, 2H), 2.82 (s, 2H), 1.44 (s, 6H). Step 4: Preparation of 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-thione

[0214] To a suspension of 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-one (0, 10 g, 0.29 mmol) in toluene (1 mL), phosphorus pentasulfide (0.072 g, 0.32 mmol) was introduced and the reaction was heated to reflux. After 2 hours, the content was allowed to reach 25 ° C, then poured into a mixture of water and ethyl acetate. The layers were separated, the organic layer was dried over sodium sulfate, concentrated under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (eluent cyclohexane / EtOAc gradient 1: 0 to 1: 1) to give 0.09 g of the title compound as a yellow gum. LC / MS (Method A) retention time = 1.16 minutes, 358 (M + H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.12 (d, 2H), 7.55 (d, 2H), 5.25 (s, 2H), 3.20 (s, 3H), 1.30 (s, 6H). 19F NMR (400 MHz, CDCl3) δ ppm: -65.33 (s).

[0215] When necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate, using standard physical separation techniques such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, (for example, using chiral starting materials). Table T1: Melting point data (mp) and / or retention times (TR) for compounds according to formula (I): Mass Ent- Tr Mét- PF Compound name Structure charged (min) ode (° C) every N-methoxy-N - [[4- [5- (trifluoromethyl) -1,2,4-

1.1 1.20 358 Oxadiazol-3-yl] phenyl] methyl] and iclopropanocarbon thioamide N-methoxy-N- [1- [5- [5- (trifluoromethyl)

1.2 -1,2,4- 1,22 378 Oxadiazol-3-yl] - 2-thienyl] ethyl] cycl

Mass Ent- Tr Mét- PF Compound name Structure charged (min) anode (° C) opropanocarbothio amide 1 - [[4- [5- (trifluoromethyl) -1,2,4- Non-oxadiazole-3-

1.3 detectable] phenyl] methyl] pyrololidin-2-thionon 5,5-dimethyl-2- [[4- [5- (trifluoromethyl) -1,2,4- 73 -

1.4 oxadiazol-3- 76 yl] phenyl] methyl] i soxazolidine-3-thione 1 - [[4- [5- (trifluoromethyl) 92 -

1.5 -1,2,4- 95 oxadiazol-3-yl] phenyl] methyl] p

Mass Ent- Tr Mét- PF Compound name Structure charged (min) anode (° C) every iperidine-2-thionon 5,5-dimethyl-2- [[4- [5- (trifluoromethyl) -1,2, 4-

1.6 oxadiazol-3- 1.16 358 A] phenyl] methyl] i-soxazolidine-3-thione

BIOLOGICAL EXAMPLES

[0216] Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. The disks or cut leaf segments are placed in multi-well plates (24-well format) on water agar. The leaf discs are sprayed with a test solution before (preventive) or after (dressing) inoculation. The compounds to be tested are prepared as solutions in DMSO (max. 10 mg / mL) which are diluted to the appropriate concentration with 0.025% Tween20 just 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 assessment of the disease level is performed 3 to 14 days after inoculation, depending on the pathosystem. The percentage of disease control in relation to untreated leaf discs or control segments is then calculated. General examples of liquid culture tests on well plates:

[0217] Fragments of mycelia or conidium suspensions 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 are pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spore / mycelium fragments is then added to generate a final concentration of the tested compound. The test plates are incubated in the dark at 24 ° C and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and the percentage of antifungal activity is calculated in relation to the untreated control. Example 1: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / preventive on leaf discs (brown rust)

[0218] 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. The leaf discs were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19 oC and relative humidity (ur) of 75% under a light regime of 12 hours of light / 12 hours of darkness in a climate-controlled chamber and the activity of a compound was evaluated as a percentage of control of the disease compared to no treatment when an appropriate level of damage caused by the disease appears in untreated leaf-checking segments (7 to 9 days after application).

[0219] The following compounds at 200 ppm in the applied formulation provide at least 80% disease control in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[0220] Compounds (from Table T1) 1.1, 1.2, 1.4, 1.5 and

1.6. Example 2: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / dressing on leaf discs (brown rust)

[0221] Leaf segments of wheat cv. Kanzler are placed on agar in multi-well plates (24-well format). The leaf segments are then inoculated with a spore suspension of the fungus. 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. The leaf segments were incubated at 19 ° C and 75% relative humidity under a 12-hour light / 12-hour dark regime in an air-conditioned chamber and the activity of a compound was evaluated as a percentage of disease control in comparison with no treatment when an appropriate level of damage caused by the disease appears in untreated leaf foliages (6 to 8 days after application).

[0222] The following compounds at 200 ppm in the applied formulation provide disease control of at least 80% in this test compared to untreated control leaf discs under the same conditions, which show extensive disease development.

[0223] Compounds (from Table T1) 1.1, 1.2, 1.4, 1.5, and 1.6. Example 3: Fungicidal activity against Phakopsora pachyrhizi / soy / preventive on leaf discs (Asian soybean rust)

[0224] Soy leaf disks 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, the leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in an air-conditioned chamber of 24-36 hours in the dark at 20 ° C and 75% ur, the leaf discs are kept at 20 ° C with 12 h of light / day and 75% ur. The activity of a compound is assessed as a percentage of disease control compared to the absence of treatment when an appropriate level of damage caused by the disease appears on untreated leaf foliar discs (12 to 14 days after application).

[0225] The following compounds at 200 ppm in the applied formulation provide disease control of at least 80% in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[0226] Compounds (from Table T1) 1.1, 1.2, 1.4, 1.5, and 1.6. Example 4: Fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liquid / cucumber / preventive culture (Anthracnose)

[0227] Conidia of the cryogenic storage fungus are directly mixed in nutrient broth (PDB - potato broth and dextrose). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 ° C and the inhibition of growth is determined photometrically 3 to 4 days after application.

[0228] The compounds that follow 20 ppm in the applied formulation provide at least 80% disease control in this test compared to the untreated control under the same conditions, which has extensive disease development.

[0229] Compounds (from Table T1) 1.1, 1.2, 1.4, 1.5, and 1.6.

Claims (13)

1. Compound of formula (I): (I) characterized by the fact that A is A-1, A-2, A-3 or A-4; (A-1) (A-2) (A-3) (A-4) and A-1, A-2, A-3 or A-4 are optionally substituted by one or two independently selected halogen groups; R1 and R2 are independently selected from hydrogen, methyl and cyan; or R1 and R2, together with the carbon atom to which they are attached, form a cyclopropyl ring; R3 is hydroxy, C1-4alkoxy or C1-3haloalkoxy; Z is R4, where R4 is C3-6cycloalkyl or heterocyclyl, where the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms or groups selected individually from N, NR5, O and S; wherein the cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R6; R6 is cyano, halogen, hydroxy, amino, methyl, ethyl, propyl, cyclopropyl, prop-2-enyl, prop-2-inyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, prop-2-enyloxy, prop-2- inyloxy, N-methylamino, N, N-dimethylamino, methylcarbonyl, methoxycarbonyl, formylamino, N-methylaminocarbonyl, N, N-dimethylaminocarbonyl or methoxycarbonylamino; and wherein Z can optionally contain 1 group selected from C (O) or S (O) 2; and R5 represents hydrogen, methyl, methoxy, formyl or acyl. or R3 and Z, together with the group -NC (= S) - to which they are attached, form a 4- to 7-membered non-aromatic heterocyclyl ring, wherein the heterocyclyl optionally comprises 1 or 2 additional members of the ring independently selected from N, O, S, C (O) and S (O) 2, with the proviso that the heterocyclyl ring cannot contain 2 contiguous atoms selected from O and S, and the heterocyclyl is optionally substituted by 1 or 2 substituents, which they can be the same or different, selected from cyan, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy; or the heterocyclyl formed by R3 and Z is replaced by a C3-6cycloalkyl group to form a spirocycle; or a salt or an N-oxide thereof. 2. A compound according to claim 1, characterized by the fact that A is A-1 optionally substituted by 1 or 2 fluorine groups, or A is unsubstituted A-4. A compound according to any one of claims 1 and 2, characterized by the fact that R1 and R2 are independently selected from hydrogen and methyl. Compound according to any one of claims 1, 2 and 3, characterized by the fact that R3 is C1-4alkoxy. Compound according to any one of claims 1, 2, 3 and 4, characterized by the fact that R3 is methoxy. Compound according to any one of claims 1, 2, 3, 4 and 5, characterized by the fact that R4 is C3-4cycloalkyl optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyan, halogen, hydroxy, amino, methyl, ethyl and propyl. A compound according to any one of claims 1, 2, 3, 4, 5 and 6, characterized by the fact that R4 is cyclopropyl optionally substituted by 1 substituent selected from R6, in which R6 is selected from cyano, halogen, hydroxy, amino, methyl, ethyl, n-propyl and isopropyl. A compound according to any one of claims 1, 2 and 3, characterized by the fact that R3 and Z, together with the group -N-C (= S) - to which they are attached, form a group selected from: where X1 and X2 are -CH2- or -O-, and each group is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyano, halogen, hydroxy, amino, C1-4alkyl, C1-4haloalkyl and C1-4alkoxy. 9. Compound according to claim 8, characterized by the fact that R3 and Z, together with the group -NC (= S) - to which they are attached, form a group selected from: where X1 and X2 are - CH2- or -O-, and each group is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from cyano, halogen, hydroxy, amino, methyl, ethyl, C1-2 fluoroalkyl, methoxy and ethoxy. 10. Agrochemical composition characterized by the fact that it comprises a fungicidal effective amount of a compound, as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8 and 9. 11. Composition according to claim 10, characterized in that it additionally comprises at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier. 12. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized by the fact that a fungicidal effective amount of a compound, as defined in any of claims 1, 2, 3, 4, 5, 6, 7, 8 and 9, or a composition comprising this compound as an active ingredient, is applied to plants, their parts or their locus. 13. Use of a compound, as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8 and 9, characterized by the fact that it is used as a fungicide.