BR112019020756A2 - OXADIAZOL DERIVATIVES MICROBICIDES - Google Patents

Abstract

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

Description

Descriptive report of the invention patent for MICROBIOCIDAL OXADIAZOL DERIVATIVES

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 that comprise 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 plant infestation, food crops collected, seeds or non-living materials, by phytopathogenic microorganisms, preferably fungi.

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

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

on what

A is:

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R ¹ and R ² are hydrogen; on what:

(i) R ³ is R ^3a , where R ^3a is hydroxyl, ethoxy, propyl, cyclopropyl or 2,2,2-trifluoroethyl; and

R ⁴ is R ^4a , where R ^4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C1-2 alkyl; or (ii) R ³ is R ^3b , where R ^3b is isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2-enyl, prop-2inyl, prop-2-enyloxy, prop-2-inyloxy , methoxyethyl, cyclopropylmethyl, or 3-oxetanyl; and

R ⁴ is R ^4b , where R ^4b is C1-4 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2-4 alkyl; and

R ⁵ is cyano, C1-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, C1-3 hydroxyalkyl, C1-3 alkoxy, C1-3 alkoxy, fluoro C1-3 C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N, N-di-alkylamino C1-3 C1-3 alkyl; or

R ⁵ represents C3-4 cycloalkyl or C34 cycloalkyl C1-2 alkyl, wherein the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclyl alkyl C1-2, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring comprising 1, 2 or 3 heteroatoms individually selected from N, 0 and S, where for R ⁵ , any portion of cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R ⁶ ;

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R ⁶ represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R ⁵ comprises a substituted C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C (0)) or sulfonyl (S (0) 2) group; or where for R ³ as defined for each of (i) and (ii), R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, form a cycle selected from 3oxo-pyrrolidinyl, pyrrolidinyl, 2 -oxo-pyrrolidinyl, azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4yl or l-piperazin-4-yl ethanone;

or a salt or N-oxide thereof;

with the proviso that the compound of Formula (I) is not: N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] morpholino-4-carboxamide ,

N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] isoxazolidine-2-carboxamide, or N-isopropylN - [[4- [5- ( trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] pyrrolidine-1-carboxamide.

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

According to a second aspect of the invention, an agrochemical composition comprising a fungicidally effective amount of a compound of Formula (I) is provided. Such an agricultural composition may comprise

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4/144 in addition, at least one additional active ingredient and / or an agrochemical acceptable diluent or carrier.

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

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

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

As used herein, cyan means a -CN group.

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

As used herein, amino means a -NH2 group.

As used here, the term C1-5 alkyl refers to a straight or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, containing no unsaturation, having one to five carbon atoms, and which is attached to the rest of the molecule by a single bond. C2-5 alkyl, C1-3 alkyl and C1-2 alkyl are to be interpreted accordingly. Examples of C1-5 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (t

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5/144 butyl). A C1-2 alkylene group refers to the corresponding definition of C1-2 alkyl, except that such a radical is attached to the rest of the molecule by two single bonds. Examples of C1-2 alkylenes are -CH2- and -CH2CH2-.

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

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

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

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

As used herein, the term C3-4 alkynyl refers to a radical group of linear or hydrocarbon chain

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6/144 branched consisting merely of carbon and hydrogen atoms, containing at least one triple bond, having three or four carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C3-4 alkynyl include, but are not limited to, prop-1-inyl, propargyl.

As used herein, the term C1-2 alkoxy C1-3 alkyl refers to the radical of formula R _y -OR _x - where R _y is a C1-2 alkyl radical as generally defined above, and R _x is an alkylene radical C1-3 as generally defined above.

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

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

As used herein, the term C1-3 alkylamino refers to a -HNR _X radical where R _x is a C1-3 alkyl radical as generally defined above.

As used herein, the term N, N-di-C 1-3 alkylamino refers to a -N (R _x ) 2 radical where R _x is the same or different C 1-3 alkyl radical as generally defined above.

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

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

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

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

As used herein, the term heterocyclyl or heterocyclic (a) refers to a stable, saturated or partially saturated, 4- to 6-membered, non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur . The heterocyclyl radical can be attached 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.

The presence of one or more possible asymmetric carbon atoms in a compound of Formula (I) means that the compounds can occur in chiral isomeric forms, that is, enantiomeric or diastereoisomeric forms. Likewise, atropisomers can also occur as a result of restricted rotation around a single bond. Formula (I) is intended to include all possible forms

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8/144 isomeric and mixtures thereof. The present invention includes all of these possible isomeric forms and mixtures thereof for a compound of Formula (I). Likewise, Formula (I) is intended to include all possible tautomers (including lactam-lactime tautomerism and keto-enol tautomerism) when present. The present invention includes all possible tautomeric forms for a compound of Formula (I).

In each case, the compounds of Formula (I) according to the invention are in the free form, in the oxidized form as a Noxide, in a covalently hydrated form, or in the form of salt, eg in a form of salt agronomically usable or agrochemically acceptable.

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

Compounds of Formula (I) that are not in accordance with the present invention are:

- N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] morpholino-4-carboxamide, and

- N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] isoxazolidine-2-carboxamide

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- N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] pyrrolidine-1-carboxamide.

The following list provides definitions, including preferred definitions, for substituents A, R ¹ , R ² , R ³ (including R ^3a and R ^3b ), R ⁴ (including R ^4a and R ^4b ), R ⁵ and R ⁶ , with reference to the compounds of Formula (I) according to the invention. For any of these substituents, any of the definitions provided below may be combined with any definition of any other substituent provided below or elsewhere in this document.

A is:

R ¹ is hydrogen.

R ² is hydrogen.

In certain embodiments of the invention (modality (i)), R ³ is R ^3a , where R ^3a is hydroxyl, ethoxy, propyl, cyclopropyl or

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2,2,2-trifluoroethyl; and R ⁴ is R ^4a , where R ^4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxyCi-3 alkyl , C3-4 cycloalkyl, or C3-4 cycloalkyl C1-2 alkyl ·

According to modality (i), preferably R ^3a is ethoxy or cyclopropyl.

According to modality (i), preferably R ^4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C34 alkynyl, C1-2 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy C1-2 alkyl, cyclopropyl or C1-2 cyclopropylalkyl · More preferably, R ^4a is C2-5 alkyl, C3-4 alkenyl or C3-4 alkynyl.

In certain embodiments of the invention (modality (ii)), R ³ is R ^3b , where R ^3b represents isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2-enyl, prop-2-inyl, prop -2-enyloxy, prop2-inyloxy, methoxyethyl, cyclopropylmethyl, or 3-oxetanyl; and R ⁴ is R ^4b , where R ^4b is C1-4 alkyl, C1-4 fluoroalkyl, Cs-4 alkenyl, Cs-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2- 4.

According to modality (ii), preferably, R ^3b is n-butyloxy, cyclopropylmethyl or 3-oxetanyl.

According to embodiment (ii), preferably, R ^4b is C1-4 alkyl, C1-2 fluoroalkyl, C1-4 cyanoalkyl, C1-4 alkoxy or 1-4 C2-4 alkoxy. More preferably, R ^4b is methyl, ethyl, C1-2 fluoroalkyl, C1-2 cyanoalkylalkyl, methoxy, ethoxy or C1-2 alkoxy C2-4 alkyl.

R ⁵ is cyano, C1-6 alkyl, C1-4 fluoroalkyl, C3-4 alkenyl, Cs-4 alkynyl, Cs-4 haloalkenyl, C1-3 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 alkoxy, C1-2 alkyl, fluoroalkoxy Ci

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11/144 C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N, N-dialkylamino C1-3 C1-3 alkyl; or

R ⁵ represents Cs-4 cycloalkyl, C3-4 cycloalkyl Ci-2 <where the cycloalkyl portion is optionally partially unsaturated, heterocyclyl, heterocyclyl alkyl Ci-2, where the heterocyclyl portion is a 4- to 6-membered non-aromatic ring comprising 1, 2 or 3 heteroatoms individually selected from N, 0 and S, where for R ⁵ , any portion of cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from of R ⁶ .

R ⁶ represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R ⁵ comprises a substituted C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C (0)) or sulfonyl (S (0) 2) group; or

Preferably R ⁵ is cyano, C1-3 alkyl, C1-3 fluoroalkyl, 63-4 alkenyl, 63-4 alkynyl, Cs-4 haloalkenyl, C1-2 cyanoalkyl, C1-2 hydroxyalkyl, C1-2 alkoxy C1-2 alkyl , fluoro C1-2 C1-2 alkyl, C1-2 aminoalkyl, N-C1-2 alkylamino C1-2 alkyl, N, N-dialkylamino C1-2 C1-2 alkyl; or R ⁵ is cyclopropyl, C1-2 cyclopropylalkyl, heterocyclyl, C1-2 heterocyclylalkyl wherein the heterocyclyl portion is a 4- to 6-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and 0, where for R ⁵ , any cycloalkyl or heterocyclyl moiety is

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12/144 optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R ⁶ .

More preferably R ⁵ is C1-3 alkyl, C1-3 fluoroalkyl, Cs-4 alkenyl, Cs-4 alkynyl, Cs-4 haloalkenyl, C1-2 cyanoalkyl, C1-2 hydroxyalkyl, C1-2 alkoxy C1-2 alkyl; or R ⁵ is cyclopropyl, C1-2 cyclopropylalkyl, heterocyclyl, C1-2 heterocyclylalkyl, wherein the heterocyclyl portion is a 4- or 5-membered non-aromatic ring comprising 1 or 2 heteroatoms individually selected from N and 0, where for R ⁵ , any cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R ⁶ .

Still more preferably, ^R5 is Ci-3 alkyl, Ci-luoroalquila f 3, 4-Cs alkenyl, C 3-4 alkynyl or C 2 cianoalquila, or R ⁵ is cyclopropyl, C 2 ciclopropilalquila <cyclopropyl which is optionally either replaced by 1 or 2 substituents, which can be the same or different, selected from R ⁶ . Even more preferably, R ⁵ is C1-3 alkyl, C1-4 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or C1-2 cyanoalkyl, or R ⁵ is cyclopropyl, C1-2 cyclopropylalkyl, where any cyclopropyl is optionally replaced by 1 or 2 substituents, which can be the same or different, selected from R ⁶ , where R ⁶ is halogen, methyl or ethyl.

where for R ³ as defined for each of (i) and (ii), R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, form a cycle selected from 3-oxopyrrolidinyl, pyrrolidinyl, 2- oxo-pyrrolidinyl,

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13/144 azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, l-methoxypiperazin-4-yl, l-methylpiperazin-4yl or l-piperazin-4-yl ethanone. Preferably, R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, form a cycle selected from morpholino or oxazinanil.

In certain embodiments of the invention, when R ³ is n-butoxy, R ⁴ can also be hydrogen.

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

It is understood that, when in aqueous media, the compounds of Formula (I) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (i.e., the compounds of Formula (I-Ia) and Formula ( I-IIa) as shown below, which can exist in tautomeric form as the compounds of formula (I-Ib) and formula (I-IIb)) in the CFs-oxadiazole motif. This dynamic balance can be important for the biological activity of the compounds of Formula (I). The designations A, R ¹ , R ² , R ³ (including R ^3a and R ^3b ), R ⁴ (including R ^4a and R ^4b ), R ⁵ and R ⁶ , with reference to the compounds of Formula (I) herein generally apply to the compounds of Formulas (II), (I-II), (I-Ia) and (I-IIa), as well as the specific disclosures of combinations of A, R ¹ , R ² , R ³ (including R ^3a and R ^3b ), R ⁴ (including R ^4a and R ^4b ), R ⁵ and R ⁶ , as represented in the compounds described in Tables 1.1 to 1.5 or as represented in the compounds described in Tables 2.1 to 2.9, or compounds 1.1 to 1.28 described in Table TI (below).

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

The compounds of formula (I) can be obtained via a coupling transformation with compounds of formula (II) and compounds of formula (III), in which X is halogen or OH, preferably halogen, in a suitable solvent (e.g. , dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 ° C and 100 ° C, and optionally in the presence of a base (eg, NaHCOs, Na2COs,

K2CO3, NaOH, triethylamine or N, N-diisopropylethylamine), or

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15/144 under conditions described in the literature for coupling urea. For examples, see WO 2003/028729, WO 2013/092943, WO 2017/055473 or WO 2014/025128. In addition, compounds of formula (I) can optionally be obtained via a coupling transformation with compounds of formula (II) and compounds of formula (III), where X is -OH, via a process that converts -OH to an improved halide leaving group, such as a chloride, for example using triphosgene, phosgene, (COC1) 2 or SOCI2, before treatment with the compounds of formula (II). The compounds of formula (III) are either commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Res. Journal (2009), 21, 133; and Crich, D., Zou, Y. J. Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 1.

Layout 1

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

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Layout 2

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

(SAW)

Layout 3

The compounds of formula (V) can be prepared from compounds of formula (VI) by treatment with a hydroxylamine hydrochloride salt or a solution of hydroxylamine in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at a temperature between 0 ° C and 80 ° C. In

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17/144 In some cases, a 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 4.

Layout 4

The compounds of formula (VI) can be prepared from compounds of formula (VII), where Y is halogen, through a reaction promoted by metals with a suitable cyanide reagent, such as Pd (0) / Zn (CN) 2 or CuCN, in a suitable solvent (eg, dimethylformamide or Nmethylpyrrolidone) at an elevated temperature between 80 ° C and 120 ° C. For related examples see US 2007/0155739 and WO

2009/022746. This reaction is shown in Scheme 5.

Layout 5

Compounds of formula (VII), where the NR ³ bond contains a directly linked unsaturated methylene segment [eg, -CH2- or -CHICs) -], can be prepared from compounds of formula (VIII) , where Y is Br or I, and R ⁴ is not equal to hydrogen, via a reaction promoted by

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18/144 base (eg, sodium hydride) with a suitable alkylating reagent (eg, methyl iodide, ethyl iodide or 2-methoxyethyl iodide), in a suitable solvent (eg, dimethylformamide or

N-methylpyrrolidone) at elevated temperature between 60 ° C

120 ° C. This reaction is shown in

Scheme

6.

R ‘

R — N

A — Y

R (VIII)

R — N

The R '

A — Y r ₃

R (VII)

Layout 6

The compounds of formula (II) in which R ¹ is hydrogen can be prepared from aldehyde compounds of formula (X), via treatment with compounds of formula (IX), in a suitable solvent, (eg, tetrahydrogen). hydrofuran or methanol) at a temperature between 25 ° C and 75 ° C followed by the addition of a reducing agent, such as NaBH4, NaBHsCN or LÍAIH4 in a suitable solvent, (eg, tetrahydrofuran or ethanol) at temperatures between 0 ° C and 25 ° C. For related examples, see Gazzola, C. and Kenyon, GL Journal of Labeled Compounds and Radiopharmaceuticals, (1978), 15,

181 and WO 2017/055473. This reaction is shown in Scheme 7.

Layout 7

Alternatively, compounds of formula (II) can be prepared from compounds of formula (XI), in which

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X is Cl, Br, I, OH or OSO2Me, through treatment with amines of formula (IX) in a suitable solvent (eg, tetrahydrofuran) at a temperature between 25 ° C and 60 ° C. For related examples, see Miyawaki, K. et al.

Heterocycles (2001), 54, 887, WO 2003/028729, WO 2017/055473 and WO 2013/066839. This reaction is shown in Scheme 8.

Layout 8

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

(XII) (XI)

Layout 9

The compounds of formula (VII), where Y is halogen or CN, can be obtained via coupling transformation with compounds of formula (XIII) and compounds of formula (III), in

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20/144 that X is halogen or OH, preferably halogen, in a suitable solvent (eg, dimethylformamide, dichloromethane, tetrahydrofuran or 2-methyltetrahydrofuran), preferably at a temperature between 0 ° C and 100 ° C , and optionally in the presence of a base (e.g., NaHCOs, Na2CO ₃ , K2CO3, NaOH, triethylamine or N, N-diisopropylethylamine), or under conditions described in the literature for coupling urea. In addition, compounds of formula (VII) can optionally be obtained via a coupling transformation with compounds of formula (XIII) and compounds of formula (III), where X is OH, via a process that converts -OH to a leaving group improved halide, such as a chloride, for example using triphosgene, phosgene, (COC1) 2 or SOCI2, before treatment with the compounds of formula (XIII). The compounds of formula (III) are either commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Res. Journal (2009), 21, 133; and Crich, D., Zou, YJ Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 10.

<') (XIII) (VII)

Layout 10

Alternatively, compounds of formula (VII), in which

Y is halogen or CN, can be prepared from compounds of formula (XIII) via treatment with triphosgene

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21/144 in a suitable solvent (eg 1,2-dichloroethane, acetonitrile, ethyl acetate, chloroform or toluene) followed by the addition of suitable aminonucleophils of formula (IX), in the presence of a suitable base, such as triethylamine . This reaction is shown in Scheme 11.

Layout 11

The compounds of formula (XIII), where Y is halogen or CN, can be prepared from compounds of Formula (XIV), where X is Cl, Br, I, OH or 0SO2Me, via treatment with amines of Formula ( IX), in the presence of a suitable base, such as NaHCOs, Na2COs, K2CO3 or NaH in a suitable solvent, such as dimethylformamide, N-methylpyrrolidine or acetonitrile, at a temperature between 0 ° C and 100 ° C. In some cases, better reaction performance can be gained through the use of a catalyst (eg, BU4NHSO4, Bu4NBr, BU4NI, NaI or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887.

This reaction is shown in Scheme 12.

Η rq \ - 2 \

N — H + R) —A — Y 3 //

RX (IX) (XIV)

Layout 12 \

R — j — A — Y

HN \ r ₃ (XIII)

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

R, Fh \ 2 \

R — j — A — Y ------ ► R — 4 — A — Y

ΗX (XV) (XIV)

Layout 13

Alternatively, compounds of formula (XIV), where X is Cl, Br, I or OSCUMe and Y is halogen or CN, are both commercially available and can be prepared from compounds of formula (XVI) via treatment with a suitable acid source (eg, hydrochloric acid, hydrobromic acid or iodic acid), or a suitable halogen source (eg, tetrabromomethane, tetrachloromethane or iodine) optionally in the presence of triphenylphosphine, or with methanesulfonyl chloride (ClSCUMe ), in a suitable solvent (eg, dichloromethane), at temperatures between 0 ° C and 100 ° C. For related examples, see Liu, H. et al Bioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A.

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23/144 et al Bioorg. Med. Chem. Lett. (2001), 1, 3161. Compounds of formula (XVI) are commercially available. This reaction is shown in Scheme 14.

R \ Ry \ 2 \

R — j — A — Y ------ ► R — 4 — A — Y

HOX

W (XIV)

Layout 14

In addition, compounds of formula (VII), where Y is halogen or CN, can be prepared from compounds of formula (XIV), where X is Cl, Br, I, or OSCQMe and Y is halogen or CN , via treatment with ureas of formula (XVII) in the presence of a base (eg, triethylamine, N, N-diisopropylethylamine, K2CO3, NaHCOs, or Na2COs) in a suitable solvent (eg, dimethylacetamide, tetra- hydrofuran, 2methyltetrahydrofuran, acetone, or acetonitrile) at a temperature between 0 ° C and 90 ° C. In some cases, better reaction performance can be gained by using a catalyst (eg, BU4NHSO4, Bu4NBr, BU4NI, NaI, or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887, WO 2003/028729, and WO 2013/066839. This reaction is shown in Scheme 15.

R (XVII) (XIV)

Layout 15

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The compounds of formula (XVII), can be prepared from amine compounds of formula (IX) via treatment with triphosgene, optionally in a suitable solvent (eg, water, acetonitrile, ethyl acetate, tetrahydrofuran, chloroform, or toluene) via the addition of a suitable aminonucleophile of formula (IV), in the presence of a suitable base (eg, pyridine, triethylamine, K2CO3, NaHCOs, Na2COs), and at a temperature between 0 ° C and 25 ° Ç. This reaction is shown in Scheme 16.

(IV) (IX) ⁰ (XVII)

Layout 16

Alternatively, the compounds of formula (XVII) can be obtained through a coupling transformation with amine compounds of formula (IX) and compounds of formula (III), where X is halogen, or OH, preferably halogen, in a suitable solvent ( e.g., dimethylformamide, acetonitrile, dichloromethane, or tetrahydrofuran), preferably at a temperature between 25 ° C and 100 ° C, and optionally in the presence of a base (eg, K2CO3, triethylamine, or N, N-diisopropylethylamine), or under conditions described in the literature for coupling urea. For examples, see WO 2003/028729. In addition, compounds of formula (XVII) can optionally be obtained via a coupling transformation with compounds of formula (IX) and compounds of formula (III), where X is OH, via a process that converts -OH into a leaving group improved halide, such as a chloride, for example using triphosgene, phosgene, (COC1) 2,

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25/144 or SOCI2, before treatment with the compounds of formula (IX). The compounds of formula (III) are either commercially available or prepared using known methods. For related examples, see: Nelson, T. D et al. Tetrahedron Lett. (2004), 45, 8917; Senthil, K. et al. Pest. Res. Journal (2009), 21, 133; and Crich, D., Zou, Y. J. Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme 17.

O O (ill) (i> 9 (xvii)

Layout 17

In addition, compounds of formula (I) can be prepared from compounds of formula (XI), where X is halogen or OSChMe via treatment with ureas of formula (XVII) in the presence of a base (e.g. , triethylamine, N, N-diisopropylethylamine, K2CO3, NaHCOs, or Na2COs) in a suitable solvent (eg, dimethylacetamide, tetrahydrofuran, 2methyltetrahydrofuran, acetone, toluene or acetonitrile) at a temperature between 0 ° C and 90 ° C. In some cases, better reaction performance can be gained by using a catalyst (eg, BU4NHSO4, Bu4NBr, BU4NI, NaI, or 4-dimethylaminopyridine) or optionally with microwave irradiation. For related examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887, WO 2003/028729, and WO 2013/066839. This reaction is shown in Scheme 18.

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Alternatively, compounds of Formula (XI), where X is hydrogen, OH, SO2Me, Cl, Br, or I, can be prepared from compounds of Formula (XVIII) by treatment with trifluoroacetic anhydride or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide) in the presence of a base (eg, pyridine or 4-dimethylaminopyridine) in a suitable solvent, (eg, ethyl acetate, tetrahydrofuran, 2-methyl- tetrahydrofuran, or ethanol), at a temperature between 0 ° C and 75 ° C. For related examples, see WO 2003/028729, WO 2017/055473, and WO 2010/045251.

This reaction is shown in Scheme 19.

(XVIII)

Layout 19

The compounds of Formula (XVIII), where X is hydrogen, OH, OSO2Me, Cl, Br or I, can be prepared from compounds of Formula (XIX) by treatment with a hydroxylamine hydrochloride salt or a hydroxylamine solution in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at a temperature between 0 ° C and 80 ° C. In some cases, better reaction performance can be gained

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27/144 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 20.

^R \ ^R \ \ 2 \ / ^0H

R 2 A- = N ----- ► R) A—

X * nh ₂ (X> X) (xviii)

Layout 20

The compounds of formula (XIX), in which C is hydrogen, OH, OSO2Me, Cl, Br, or I, can be prepared from compounds of formula (XIV), in which Y is halogen, via reaction promoted by metals with a suitable cyanide reagent, such as Pd (0) / Zn (CN) 2 or CuCN, in a suitable solvent (eg, dimethylformamide or N-methylpyrrolidone) at an elevated temperature between 100 ° C and 120 ° C. For related examples see US 2007/0155739 and WO 2009/022746. This reaction is shown in Scheme 21.

_R ; 4 \ 2 \ r ² _ \ - _A -Y ------ ► R —- A — N

X (XIV) (XIX)

Layout 21

Compounds of Formula (XIV), where X is Cl, Br, I or OSO2Me and Y is halogen or CN, are either commercially available or can be prepared from compounds of Formula (XX), where Y is halogen or CN, via treatment with a suitable acid source (eg, hydrochloric acid, hydrobromic acid, or iodic acid), or with a suitable halogen source (eg, CClsBr, CCI4 or I2) in the presence

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28/144 triphenylphosphine, or with methanesulfonyl chloride (ClSCUMe), in a suitable solvent, (eg, dichloromethane) at a temperature between 0 ° C and 100 ° C. For related examples, see Liu, H. et al Bioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A. et al Bioorg. Med. Chem. Lett. (2001), 1, 3161. The compounds of formula (XX) are either commercially available or prepared using known methods. This reaction is shown in Scheme 22.

^R \ ^R \ \ 2 \

R ² \ AY ------ ► R) A — Y

HOX (XX) (XIV)

Layout 22

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

The compounds of formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for the control of plant pests or in non-living materials for the control of microorganisms that cause deterioration or organisms potentially harmful to man. The new compounds are distinguished by 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 various cultivated plants. The compounds of

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Formula (I) can be used to inhibit or destroy pests that occur on plants or parts of plants (fruit, flowers, leaves, stems, tubers, roots) from different crops of useful plants, while also protecting those parts of plants that grow later, eg from phytopathogenic microorganisms.

The present invention further relates to a method for controlling or preventing infestation of harvested plants or plant propagating material and / or food crops susceptible to microbial attack, by treating plants or propagating material of harvested plants and / or food crops , in which an effective amount of a compound of Formula (I) is applied to plants, their parts or their locus.

It is also possible to use compounds of Formula (I) as a fungicide. The term fungicide, as used herein, means a compound that controls, modifies or prevents the growth of fungi. The term fungicidal effective amount, when used, means the amount of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. 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.

It may also be possible to use compounds of Formula (I) as curative agents for the treatment of plant propagating material, eg seeds, such as fruits, tubers or grains, or plant cuttings, for protection

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30/144 against fungal infections, as well as against phytopathogenic fungi that occur in the soil. The propagation material can be treated with a composition comprising a compound of Formula (I) before planting: a seed, for example, can be treated before being sown. The active compounds of Formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example, to the seedbed during sowing. The invention also relates to such methods of treating plant propagating material and to the plant propagating material so treated.

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

In addition, the invention could be used to protect non-living materials from fungal attack, eg, construction wood, wall panels and paint.

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

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31/144 spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. inclusing 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.

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32/144 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, Stagonosporphylorum, Stagonosporphylphorum, Stagonosporphylphorus, Stagonosporphylphalum, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

The compounds of Formula (I) can be used for example in peat, ornamental plants, such as flowers, shrubs, trees with broad or perennial leaves, for example conifers, as well as for tree injection, pest management and the like.

Within the scope of the present invention, target crops and / or useful plants to be protected typically comprise perennial and annual crops, such as berries, for example.

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33/144 example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, corn (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, levistico, 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.

Useful plants should be understood to also include useful plants that have been made tolerant to herbicides, such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, eg primisulfurone, prosulfurone and trifloxysulfurone, inhibitors of EPSPS (5-enol-pyrovilchiquimate-3-phosphate synthase), GS inhibitors (glutamine

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34/144 synthetase) or PPO (protoporphyrinogenoxidase) inhibitors) as a result of conventional methods of genetic improvement or modification. An example of a crop that has been made tolerant to imidazolinones, eg imazamox, by conventional breeding methods (mutagenesis) is the Clearfield® summer rapeseed (Canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate and glufosinate resistant maize varieties, commercially available under the trademarks RoundupReady®, Herculex I® and LibertyLink®.

Useful plants should be understood as also including useful 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, for example, from bacteria that produce toxins, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (variety of corn that expresses a CrylA toxin (b)); YieldGard Rootworm® (variety of corn that expresses a CrylIIB toxin (bl)); YieldGard Plus® (variety of maize that expresses a CrylA toxin (b) and a CrylIIB toxin (bl)); Starlink® (variety of corn that expresses a Cry9 toxin (c)); Herculex I® (variety of corn that expresses a CryIF toxin (a2) and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA (c) toxin); Bollgard I® (cotton variety that expresses a CrylA (c) toxin); Bollgard II® (cotton variety that

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35/144 expresses a CrylA toxin (c) and a CrylIA toxin (b)); VIPCOT ® (cotton variety that expresses a VIP toxin); NewLeaf ® (potato variety that expresses a CrylIIA toxin); NatureGard®Agrisure® GT Advantage (glyphosate tolerance trait GA21), Agrisure® CB Advantage (trait of borer borer (CB) Btll), Agrisure® RW (trait of corn rootworm) and Protecta®.

The term cultures is to be understood as including also culture plants that have been transformed in such a way by the use of recombinant DNA techniques, which are able to synthesize one or more selectively active toxins, as they are known, for example, from bacteria producing toxins, especially those of the Bacillus genus.

Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δendotoxins, e.g., CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vipl, Vip2 , Vip3 or Vip3A; or insecticidal proteins from bacteria colonizing nematodes, 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 Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or white bell lectins; agglutinins;

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36/144 proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, maize RIP, abrina, lufina, saporina or briodina; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDPglycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COα-reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

Additionally, in the context of the present invention, δ-endotoxins should be understood, for example, CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C or vegetative insecticidal proteins (Vip), for example, Vipl, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of these proteins (see, for example, WO 02/15701). Truncated toxins are known, for example a truncated CrylAb. 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, as, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into a Cry3A toxin (see WO 03 / 018810).

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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.

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. Cryox-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.

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).

Transgenic plants are known to contain one or more genes that encode an insecticidal resistance and express one or more toxins and some of them are commercially available. Examples of such plants are: YieldGard® (variety of corn that expresses a CrylAb toxin); YieldGard Rootworm® (variety of corn that expresses a Cry3Bbl toxin); YieldGard Plus® (variety of maize that expresses a CrylAb toxin and a Cry3Bbl); Starlink® (variety of corn that expresses a Cry9C toxin); Herculex I® (variety of corn that expresses a CrylFa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonia); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a toxin

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CrylAc); Bollgard II® (cotton variety that expresses a CrylAc toxin and a Cry2Ab); VipCot® (cotton variety that expresses a Vip3A toxin and a CrylAb); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (glyphosate trait GA21), Agrisure® CB Advantage (trait corn borer (CB) Btll) and Protecta®.

Additional examples of such transgenic crops are:

1. Maíz Btll of Syngenta Seeds SAS, Chemin de 1'Hobit 27, F31 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 nonagrioid.es) by transgenic expression of a truncated CrylAb toxin. Maize Btll also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

2. Maíz Btl76 from Syngenta Seeds SAS, Chemin de 1'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 CrylAb toxin. The Btl76 corn also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

3. Maíz MIR604 from Syngenta Seeds SAS, Chemin de 1'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Maiz that has been made resistant to insects by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by inserting a sequence

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39/144 cathepsin G protease recognition. The preparation of such transgenic maize plants is described in WO 03/018810.

4. Maiz 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 Cry3Bbl toxin and is resistant to certain Coleoptera insects.

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

6. Maize 1507 of Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00/10. Genetically modified maize for the expression of the CrylF protein to achieve resistance to certain Lepidopteran insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

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

The compounds of Formula (I) (including any compound described in Tables 1.1 to 1.5 or Tables 2.1 to 2.9, or a compound 1.1 to 1.28 described in Table TI (below) can be used in the control or prevention of diseases

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40/144 phytopathogenic, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as deltaendotoxins, e.g., CrylAc (Bt CrylAc protein). Consequently, this can 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 Al (see, eg, paragraph [008] reference to Intacta RR2 PRO ™ soybeans), event MON87751 (U.S. Patent Application Publication No. 2014/0373191) or DAS-81419 event (U.S. Patent No. 8632978 and related applications and patents).

Other transgenic soybean plants may comprise the SYHT0H2 event - tolerance to HPPD (US Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (US Patent No. 7,632,985 and applications and related patents), event MON87708 - dicamba tolerance (US Patent Application Publication No. US 2011/0067134 and related patents and applications), event DP356043-5 - glyphosate tolerance and ALS (US Patent Application Publication N ° US 2010/0184079 and related applications and patents), event A2704-12 - tolerance to glufosinate (US Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP305423-1 - ALS tolerance ( U.S. Patent Application Publication No. US 2008/0312082 and related patents and applications), event A5547-127 - glufosinate tolerance

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41/144 (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see documents WO 2011/022469, WO 2011 / 022470, WO 2011/022471, and related applications and patents), event 127 - tolerance to ALS (WO 2010/080829 and related applications and patents), event GTS 40-3-2 glyphosate tolerance, event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, event FG72 tolerance to glyphosate and isoxaflutole, event BPS-CV127-9 tolerance to ALS and GU262 - tolerance to glufosinate or event SYHT04R - tolerance to HPPD.

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

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

The term plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for 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 must be transplanted after germination or after emergence from the soil, can also

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42/144 be mentioned. These young plants can be protected before transplantation through total or partial immersion treatment. Preferably, plant propagation material is understood to denote seeds.

The compounds of Formula (I) can be used in an unmodified form or, preferably, in conjunction with adjuvants conventionally employed in the formulation technique. For this purpose, they can be conveniently formulated in a known manner in emulsifiable concentrates, coated pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wetting powders, soluble powders, dust, granules and also encapsulations, eg in substances polymeric. As with the type of the 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 can also contain other adjuvants such as stabilizers, defoamers, viscosity regulators, binders or tackifiers, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

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 described, for example, in WO 97/33890.

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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 can additionally include a wetting agent to enhance 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.

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

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

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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 clays, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, sawdust, cobs crushed corn, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials that absorb or can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients that may include surfactants, such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and / or adhesives, such as dextrins, glue or synthetic resins.

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

Microcapsules are typically droplets or granules of the active ingredient encased in an inert porous shell that allows the release of the encased material to the vicinity at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The closed liquid typically constitutes 50 to 95% of the weight of the capsule

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45/144 and may include a solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form within the granule pores. The granules typically range from 1 millimeter to 1 centimeter and preferably from 1 to 2 millimeters in diameter. The granules are formed by extrusion, agglomeration or compression, or they occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, atapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other 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, in which the active ingredient is dispersed in a finely divided form as a result of the vaporization of a dispersing solvent carrier with a low boiling point, can also be used.

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.

Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, oil

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46/144 vegetable, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N, N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, ether dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol ether, ether ether ethylene glycol methyl, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isopropylben, isopropylben o, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n -octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monoethyl ether, p-xylene, toluene, triethyl acid, triethylene phosphate, triethylene xylenesulfonic, paraffin, mineral oil, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol,

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47/144 isopropanol and high 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.

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, seed pods. cotton, wheat flour, soy flour, pumice stone, wood flour, nutshell flour and lignin.

A wide variety of surfactants are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can have anionic, cationic, non-ionic or polymeric character and can and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Surface active agents include salts of alkyl sulfates, such as lauryl diethanolammonium sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenolalkylene oxide addition products, such as nonylphenol-C.sub ethoxylate. 18 nonylphenol; alcohol-alkylene oxide addition products, such as tridecyl-ethoxylate alcohol C.sub. 16; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as

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48/144 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.

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.

In addition, 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 in conjunction with the compositions of the invention, or mixed, for example, in the spray tank. These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

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

In addition, the compositions of the invention can also be applied with one or more inductors of systemically acquired resistance (SAR inducer). 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-Smetila.

The compounds of Formula (I) are normally used in the form of agrochemical compositions, and can be applied to the crop area or plant to be treated, simultaneously or successively with additional compounds. These additional compounds can be eg fertilizers or micronutrient donors or other preparations, which influence plant growth. These 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, usually employed in the formulation technique .

The compounds of Formula (I) can be used in the form of compositions (fungicides) to control or protect against phytopathogenic microorganisms, comprising as active ingredient at least one compound of Formula (I) or at least one individual compound preferred as on here

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50/144 defined, in free form or in the form of agrochemically usable salt, and at least one of the aforementioned adjuvants.

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

The compound of Formula (I) can be the only active ingredient in a composition or it can 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.

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, benzanide fungicides benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides

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51/144 dicarboximide, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolan fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, oregano fungicides, oregano fungicides oxatiin, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxin fungicides, quinoxin fungicides , sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides and urea fungicides.

Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1-methylH-pyrazolo-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5- il) -amide, 3difluoromethyl-1-methyl-1H-pyrazolo-4-carboxylic acid methoxy- [1 methyl-2- (2,4,6-trichlorophenyl) -ethyl] -amide, 1-methyl3-difluoromethyl-1H acid -pyrazolo-4-carboxylic (2dichloromethylene-3-ethyl-1-methyl-indan-4-yl) -amide (107295771-1), 1-methyl-3-difluoromethyl-1H-pyrazole-4carboxylic acid (4'-methylsulfanyl -biphenyl-2-yl) -amide, 1methyl-3-difluoromethyl-4H-pyrazolo-4-carboxylic acid [2- (2,4 dichloro-phenyl) -2-methoxy-1-methyl-ethyl] -amide, ( 5-chloro-2,4dimethyl-pyridin-3-yl) - (2,3,4-trimethoxy-6-methyl-phenyl) Petition 870190098775, of 10/02/2019, p. 64/162

52/144 methanone, (5-Bromo-4-chloro-2-methoxy-pyridin-3-yl) - (2,3, 4-trimethoxy-6-methyl-phenyl) -methanone, 2- {2 - [(E) -3- (2,6dichloro-phenyl) -l-methyl-prop-2-en- (E) -ilideneaminooxymethyl] -phenyl} -2 - [(Z) -methoxy-imino] -N-methyl-acetamide, 3 [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, (E) -N-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2 -methoxyiminoacetamide, 4-bromo-2-cyano-N, N-dimethyl-6trifluoromethylbenzimidazole-1-sulfonamide, a- [N- (3-chloro-2,6-6-xylyl) -2-methoxyacetamido] -i-butyrolactone, 4 -chloro-2-cyano-Ν, Ν-dimethyl-5-p-tolylimidazolo-1-sulfonamide, Nalyl-4, 5, -dimethyl-2-trimethylsilylthiophene-3-carboxamide, N (1-cyano-1,2-dimethylpropl) -2- (2,4-dichlorophenoxy) propionamide, N- (2-methoxy-5-pyridyl) cyclopropanecarboxamide, (. H—.) - cis-1- (4-chlorophenyl) -2- (1H1,2,4 -triazol-1-yl) -cycloheptanol, 2- (1-tert-butyl) -1- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) -propan-2-ol, 2 ', 6' dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3thiazol-5-carboxanilide, 1-imidazolyl-l- (4'-chlorophenoxy) 3,3-dimethylbut an-2-one, (E) -2- [2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl] methyl 3-methoxyacrylate, (E) -2- [2- [6- (2- methyl thioamidophenoxy) pyrimidin-4yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2 - Methyl [2- [6- (2,6-difluorophenoxy) pyrimidin-4yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [3 (pyrimidin-2-yloxy) phenoxy] phenyl] - Methyl 3-methoxyacrylate, (E) -2- [2- [3- (5-methylpyrimidin-2-yloxy) phenoxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [3 ( methyl phenylsulfonyloxy) phenoxy] phenyl-3-methoxyacrylate, (E) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate

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53/144 methyl, (E) -2- [2-phenoxyphenyl] -3-methyl methoxyacrylate, (E) -2- [2- (3,5-dimethyl-benzoyl) pyrrol-l-yl] -3 -methyl methoxyacrylate, (E) -2- [2- (3-methoxyphenoxy) phenyl] -3-methyl methoxyacrylate, (E) -2 [2- (2-phenylethen-1-yl) -phenyl] -3methoxyacrylate methyl, (E) -2- [2- (3,5dichlorophenoxy) pyridin-3-yl] -3-methyl methoxyacrylate, (E) -2- (2- (3- (1,1,2,2 methyl-tetrafluoroethoxy) phenoxy) phenyl) -3methoxyacrylate, (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methyl methoxyacrylate, (E) -2- (2- (4- methyl phenoxypyridin-2-yloxy) phenyl) -3-methoxyacrylate, (E) -2- [2- (3-n-propyloxy-phenoxy) phenyl] 3 methyl methoxyacrylate, (E) —2— [2— (3 - methyl isopropyloxyphenoxy) phenyl] -3-methoxyacrylate, (E) 2- [2- [3- (2-fluorophenoxy) phenoxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [2- (3 methyl-ethoxyphenoxy) phenyl] -3-methoxyacrylate, (E) -2- [2- (4-tert-butyl-pyridin-2-yloxy) phenyl] -3 methyl methoxyacrylate, (E) -2- [2- [3- (3-cyanophenoxy) phenoxy] phenyl] -3-methyl-methoxyacrylate, (E) 2- [2 - [(3-methyl-pyridin-2-yloxymethyl) phenyl] -3 methyl-methoxyacrylate, (E) -2- [2- [6- (2-methyl-phenoxy) pyrimidin-4yloxy] phenyl] -3-methyl-methoxyacrylate, (E) -2- [2- (5-bromopyridin Methyl -2-yloxymethyl) -phenyl] -3-methoxyacrylate, (E) -2- [2- (3- (3-iodopyridin-2-yloxy) phenoxy) phenyl] -3-methylmethoxyacrylate, (E) -2- [2- [6- (2-chloropyridin-3yloxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E), (E) -2- [2- (5,6-dimethylpyrazin-2ylmethyloximinomethyl) methyl phenyl] -3-methoxyacrylate, (E) 2- {2- [6- (6-methylpyridin-2-yloxy) pyrimidin-4-yloxy] phenyl} -3methoxyacrylate methyl, (E), (E) - 2— {2- (3methoxyphenyl) methyloximinomethyl] -phenyl} -3-methoxyacrylate

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54/144 methyl, (E) —2 - {2 - (6- (2-azidophenoxy) -pyrimidin-4yloxy] phenyl} -3-methyl methoxyacrylate, (E), (E) —2— {2— [ 6— methyl phenylpyrimidin-4-yl) -methyloximinomethyl] -phenyl} -3methoxyacrylate, (E), (E) -2- {2 - [(4-chlorophenyl) methyloximinomethyl] -phenyl} -3-methoxyacrylate, ( AND)-

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-methoxyacrylate, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in), 2,6-dichloro -N- (4-trifluoromethylbenzyl) -benzamide, alcohol of

3-iodo-2-propynyl, 4-chlorophenyl-3-iodopropargyl formaldehyde, 3-bromo-2,3-diiodo-2propenyl ethyl, 2,3,3-triiodoalyl alcohol, 3-bromo2,3- alcohol diiodo-2-propenyl, 3-iodo-2-propynyl n-butylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexyl-carbamate, 3-iodine-2-propynyl phenylcarbamate; phenol derivatives, such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, ophenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 5-hydroxy- 2 (5H) -furanone; 4,5dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5trimethyleneditiazolinone, 4,5-dichloro- (3H) -1,2-dithiol-3ona, 3,5-dimethyl-tetrahydro-1,3,5-thiadiazino- 2-thione, N- (2-p-chlorobenzoylethyl) -hexaminium chloride, acibenzolar, acipetaques, alanicarb, albendazole, aldimorph, alicine, allyl alcohol, ametoctradine, amisulbrome, amobame, ampropylfos, anilazine, aomatopozone, aureus, azureofac , azithyram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanyl, benomyl, benquinox,

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55/144 bentalurone, bentiavalicarb, bentiazole, benzalkonium chloride, benzamacrila, benzamorph, benzohydroxamic acid, benzovindiflupir, berberine, betoxazin, biloxazole, binapacril, biphenyl, bitertanol, bitionol, bromo-bromine, bromo-bromine, blastic, bastice butiobate, calcium and butylamine polysulfide, captafol, captan, carbamorph, carbendazim, carbendazim, carbendazim hydrochloride, carboxine, carpropamide, carvone, CGA41396, CGA41397, chinomethionate, chitosan, clobentiazone, chloramide, chloramide, chloranhydrone chlorozolinate, clozolinate, climbazol, clotrimazole, clozilacon, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate , copper talate, copper zinc chromate and Bordeaux mixture, cresol, cufranebe, cuprobame, cuprous oxide, ciazo famida, cyclamfuramide, cycloheximide, cyflufenamide, cymoxanil, cyipendazole, cyproconazole, cyprodinil, dazomete, debacarb, decafentin, dehydroacetic acid, disulfide 1, di-2-pyridyl dioxide, diclofluanine, diclofluanane, diclofluanane, diclofluanane, diclofluanane dichlorophen, diclozoline, diclobutrazol, diclocimet, dietofencarb, diphenoconazole, difenzoquate, diflumetorime, 0, O-diisopropyl-S-benzyla, dimefluazole, dimethaclone, dimetconazole, dimethoxazole, dinomethamine, dinethazole, dimethoxazole, dinethazone dinocapo, dinoctona, dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrithione, disulfirame, ditalymph, dithianone, dithioeter, dodecyl dimethyl ammonium chloride,

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56/144 dodemorfe, dodicin, dodino, doguadino, drazoxolone, edifenfos, enestroburine, epoxiconazole, etaconazole, eteme, etaboxam, ethirimol, ethoxyquin, ethylicin, (Z) -N-benzyl-N ([methyl (methylene-oxide) methylene-thioquinoline-thioquinoline) amino] thio) -ethyl-halaninate, etridiazole, famoxadone, phenamidone, phenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fen-hexamide, phenitropane, phenoxanil, fenpiclonil, fenpicoxamide, fenpropidina, fenpropidina, fenpropidina, fenpropimina, fenpropidina, fenpropidina, fenpropidina, fenpropido , ferbame, ferimzone, fluaziname, fludioxonil, flumetover, flumorfe, flupicolide, fluopyramid, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, fluutretil, fluoxetamide, fluoxetamide, fluoxetamide , furconazole, furfural, furmeciclox, furofanato, gliodina, griseofulvina, guazatina, halacrinato, hexa chlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexiltiofos, hi drargafen, hydroxyisoxazole, himexazole, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezine, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, isopran, isopropyl, isopropyl, ipropion, ipro , cresoximmetila, LY186054, LY211795, LY248908, mancozebe, mandipropamide, manebe, mebenilla, mecarbinzida, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercury chloride, methoxyl, methiloxane, methoxazole, methoxazole, methoxazole, methoxan, metfuroxam, methyl bromide, iodide

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57/144 methyl, methyl isothiocyanate, methyramine, methiram-zinc, metominostrobin, metrafenone, metsulfovax, milnebe, moroxidine, myclobutanyl, miclozoline, nabame, natamycin, neoasozine, nickel, nitrostin, nitrostin, nitrostin, nitrostin, nitrostin, nitrostin , ofurace, organomercurium compounds, orisastrobin, ostol, oxadixyl, oxasulfurone, oxatiapiproline, ooxine-copper, oxolinic acid, oxpoconazole, oxycarboxine, parinol, pefurazoate, penconazole, pencicurone, penhufen, pentachlorophenol, pentachlorophenol, pentachlorophenol, phenoxyphenol, pentachlorophenol, pentachlorophenol fosetila-Al, phosphorous acids, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxime, polyamide, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazide, protiocarb, pyridine, pyridyl, pyridyl, pyridine, protiocarb, pyridine, protiocarb, pyridine, protiocarb, pyridine, protiocarb, pyridine, protiocarb, pyridine, pyridine , pyramethrostrobin, piraoxystrobin, pyrazophos, pyribencarb, pyridinitrile, pirifenox, pyrimethanil, pyriophene na, piroquilone, piroxiclor, piroxifur, pyrrolnitrina, quaternary ammonium compounds, quinacetol, quinazamide, quinconazole, quinomethionate, quinoxyphene, quintozene, rabenzazole, santonine, silkxane, silthiophen, simeconazole, sipconazole, sulphoxenoline, pentachloramine, pentachloramine, streptofloramine , tebuconazole, tebfloquine, chaveoftalame, tecnazene, tecorame, tetraconazole, thiabendazole, thiadifluoride, ticiofene, tifluzamide, 2- (thiocyanomethyl), benzothiazole, thiofanatemethyl, thioquinox, thiadinyl, thiadinyl, thiadinyl, thiadinyl, tiadofin, triamiphos, triarimol, triazbutyl, triazoxide,

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58/144 tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforin, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozoline, zarilamide, zine, zirame, and zoxamide.

The compounds of the invention can also be used in combination with anthelmintic agents. Such anti-helminthic 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-4444964 and EP-5929464 and EP-5929464 and EP-5944964 and EP-5929464 . 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 imidazotrazors and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include fluquicides, such as triclabendazole and clorsulone, and cestocides, such as praziquantel and epsiprantel.

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

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59/144

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 anti-helminthic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053 , WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173 and EP 0 503 538.

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

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

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

Organophosphates: Aphosphate, azametiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chloropyriphos, chlorophenvinphos, chloromephos, demetone, demetone-S-methyl, demetone-S-methylsulfone, dialectic dicrotophos, dimetoate, disulfotone, ethione, etoprofós, etrinfós, fanfur, fenamiphos, fenitrothione, fensulfothione, fentiona, flupirazofós, phonofós, formothione, fostiazato, heptenofós, isazofós, isothioato, isoxationa, methazione, malation

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60/144 metamidophos, metidationa, methyl-parathione, mevinfós, monocrotofós, nalede, ometoate, oxidemetona-methyl, paraoxone, parathione, parathione-methyl, fentoate, fosalone, phospholane, phosfocarb, fosmete, phosphamidone, pyrimimos, pyrimimos, pyrimos, -methyl, profenofós, propafós, proetanfós, protiofós, piraclofós, pyridapentiona, quinalfós, sulprofós, temefós, terbufós, tebupirinfós, tetrachlorvinfós, timetona, triazofós, trichlorofone, vamidothione. Carbamates: alanicarb, aldicarb, 2sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloetocarb, etiofencarb, phenoxycarb, fentiocarb, furatiocarb, HCN-801, isoprocar, carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

Pyrethroids: acrinatin, alethrin, alfamethrin, (E) (1R) -cis-2,2-dimethyl-3- (2-oxothiolan-3ilidenomethyl) 5-benzyl-3-furylmethyl cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, acipermethrin, beta-cypermethrin, bioalethrin, bioalethrin (isomer (S) -cyclopentyl), biormethrin, bifentrin, NCI85193, cycloprotrin, cyhalothrin, cytitrine, cyphenothrin, deltamethrin, empentrine, esfenvalerate, etofenprox, fletrine, phenatrutrin, flufin, fenflin isomer D), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transflutrin, theta-cypermethrin,

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61/144 silafluofeno, t-fluvalinato, teflutrina, tralometrina, Zetacipermetrina.

Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, triflumurine, dihydrofluorohydrate, dihydrofluorohydrate, diuretic acid; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxifene, methoprene (including S-methoprene), phenoxycarb; d) inhibitors of lipid biosynthesis: spirodiclofen.

Other antiparasitic agents: acequinocila, amitraz, AKD1022, ANS-118, azadiractin, Bacillus turingiensis, bensultape, biphenazate, binapacrilla, bromopropylate, BTG504, BTG-505, camphorchlor, cardpe, chlorobenzilate, chlorodime, chlorodime, chlorodime diafentiurone, DBI-3204, dinactin, di-hdroxymethyldihydroxypyrrolidine, dinobutone, dinocape, endosulfan, etiprol, etofenprox, phenazaquin, flumite, MTI- 800, fenpyroxy, fluacripyrine, flubenzoxin, flufen, fluorohydride IKI-220, canemite, NC-196, neem protector, nidinorterfuran, nitanpirame, SD-35651, WL-108477, pyridine, propargite, protrifenbute, pymetrozine, pyridabeme, pyrimidipheme, NC-1111, R-195, RH0345, RH- 2485, RYI-210, S-1283, S-1833, SI-8601, silafluofene silomadin spinosade tebufenpirade tetradifone tetranactin thiaclopride thiocyclame

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62/144 thiamethoxam, tolfenpirade, triazamate, triethoxyspinosine, trinactin, verbutine, vertalec, YI-5301.

Biological agents: Baciilus thuringiensis ssp aizawai, kurstaki, Baciilus thuringiensis endotoxin delta, baculovirus, entomopathogenic bacteria, viruses and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penetamato, moloxicame, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazeprila, pyriprol, cefquinoma, florfenicol, buserelin, cefovecin, trachyltin, trachlorhydrate, trachyltin, trachyltin, trachyltin, trachyltin, trachyltin, trachyltin, trachyltin, trichloramine, trachyltin, trichlorhydrate.

The following mixtures of the compounds of Formula (I) with active ingredients are preferred. The abbreviation TX designates a compound selected from the group consisting of the compounds described in Tables 1.1 to 1.5, Tables 2.1 to 2.9 or Table TI (compounds 1.1 to 1.28) (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-Nmeti-N1-naphthylacetamide (IUPAC name) (1295) + TX, 4 sulfone -chlorophenyl and phenyl (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprol [CCN] + TX, acrinatrine (9) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, alpha-cypermethrin (202) + TX, amidithione (870) + TX,

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63/144 amidoflumete [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, oxide arsenious (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotine (46) + TX, nitrogen (889) + TX, benomyl (62) + TX, benoxafós (alternative name) [CCN] + TX, benzoxide (71) + TX, benzyl benzoate (name IUPAC) [CCN] + TX, biphenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclene (918)

+ TX, bromophos (920) + TX, bromophos-ethyl (921) + TX bromopropylate (94) + TX, buprofezin (99) + TX butocarboxime (103) + TX, butoxycarboxime (104) + TX

butylpyridaben (alternative name) + TX, calcium polysulphide (IUPAC name) (ill) + TX, campheclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, chlorobenside (959) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964) + TX , chlorophenapyr (130)

+ TX, chlorophenetole (968) + TX, chlorophensone (970) + TX, chlorophensulfide (971) + TX chlorofenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuforme (977) + TX, chloromethiurone (978) + TX, chloropropylate (983) + TX, chloropyrifos (1 45) + TX, chloropyrifos-methyl (146) + TX, chlorothiophos (994) + TX cine rina I (696) + TX, cinerina II (696) + TX, cinerinas (696) + TX, clofentezine (158) + TX,

closantel (alternative name) [CCN] + TX, coumafós (174) +

TX, crotamitone (alternative name) [CCN] + TX, crotoxiphos

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64/144 (1010) + TX, cufranebe (1013) + TX, cyantoate (1020) + TX, ciflumetofeno (CAS No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefiona (1037) + TX, demefiona-0 (1037) + TX, demefiona-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-0 (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S -methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialiphos (1042) + TX, diazinone (227) + TX, diclofluanide (230) + TX, dichlorvos (236 ) + TX, diclifós (alternative name) + TX, dicofol (242) + TX, dicrotofós (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimetoate (262) + TX, dinactin (name alternative) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobutone (269) + TX, dinocape (270) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinocton (1090) + TX, dinopentone (1092) + TX, dinosulfone (1097) + T X, dinoterbone (1098) + TX, dioxationa (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfyrame (alternative name) [CCN] + TX, disulfotone (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothione (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethione (309) + TX, etoate-methyl (1134) + TX, ethoxazole (320) + TX, etrinfós (1142) + TX, fenazaflor (1147) + TX, phenazaquime (328) + TX, fenbutatin oxide ( 330) + TX, phenothiocarb (337) + TX, fenpropatrin (342) + TX, fenpirade (alternative name) + TX, fenpyroximate (345) + TX, fensona (1157) + TX, fentrifanila (1161) + TX, fenvalerato ( 349) + TX, fipronil (354) + TX, fluacripyrim (360) + TX,

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65/144 fluazurome (1166) + TX, flubenzimine (1167) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formione (1192) + TX, formparanate (1193) + TX, gammaHCH (430) + TX, gliodine (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (lUPAC / Chemical Abstracts) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, 0 (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, Jasmine I (696) + TX, Jasmine II (696) + TX, Iodophenphos (1248) + TX, Lindane (430) + TX, Lufenurone (490) + TX, Malathi (492 ) + TX, malonobene (1254) + TX, mecarbame (502) + TX, mefosfolane (1261) + TX, messulfe no (alternative name) [CCN] + TX, metacriphos (1266) + TX, metamidophos (527) + TX, methidathione (529) + TX, metiocarb (530) + TX, methomyl (531) + TX, methyl bromide ( 537) + TX, metolcarb (550) + TX, mevinfós (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotofós (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, nalede (567) + TX, NC-184 (compound code) + TX, NC-512 (code compound) + TX, nifluridide (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1: 1 zinc chloride (1313) + TX, NNI-0101

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66/144 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxisulfotone (1325) + TX, pp'-DDT (219) + TX, parathione (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, phosmet (638) + TX, phosphamidone (639) + TX, foxime (642) + TX, pyrimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofós (662) + TX, promacila (1354) + TX, propargita (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidationa (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridafentiona (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, quinalfós (711) + TX, quintiofós (1381) + TX, R-1492 (code of development (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, escradano (1389) + TX, sebufós (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, sulfirame (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotepe (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau- fluvalinate (398) + TX, tebufenpirada (763) + TX, TEPP (1417) + TX, terbame (alternative name) + TX, tetrachlorvinfós (777) + TX, tetradifone (786) + TX, tetranactin (alternative name) (653 ) + TX, tetrasul (1425)

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67/144 + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiophanox (800) + TX, thiometone (801) + TX, thioquinox (1436) + TX, turingiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, trichlorophone (824) + TX, triphenophos (1455) + TX, trinactin (alternative name ) (653) + TX, vamidothione (847) + TX, vaniliprol [CCN] and YI-5302 (compound code) + TX, an algaecide selected from the group of substances consisting of betoxazine [CCN] + TX, copper dioctanoate ( IUPAC name) (170) + TX, copper sulphate (172) + TX, cybutrin [CCN] + TX, diclone (1052) + TX, dichlorophene (232) + TX, endothal (295) + TX, fentine (347) + TX, hydrated lime [CCN] + TX, nabame (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, an anthelmintic selected from the subs group 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,

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68/144 fentiona (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of l-hydroxy-lH-pyridine-2 -thione (IUPAC name) (1222) + TX, 4- (quinoxalin-2ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, dioctanoate copper (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, phenaminosulfine (1144) + TX, formaldehyde (404) + TX, hydrargafene (alternative name) [CCN] + TX, casugamycin (483) + TX, nickel hydrated casugamycin hydrochloride (483) + TX, bis (dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapirin (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, sodium sesquisulfate

streptomycin (744) + TX, keyboardoftalame (766) + TX, and thiomersal (name an agent alternative) [CCN] + TX, biological selected from group in substances consisting in Adoxophyes orana GV (name

alternative) (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)

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69/144 (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,

Petition 870190098775, of 10/02/2019, p. 82/162

70/144 multicapsid nuclear polyhedrosis virus from Spodoptera exigua (scientific name) (741) + TX, Steinernema bibionis

(alternative name) i (742) + TX, Steinernema carpocapsae (name alternative) (742) + TX, Steinernema feltiae (name alternative) (742) + TX, Steinernema glaseri (name alternative) (742) + TX, Steinernema riobrave (name alternative) (742) + TX, Steinernema riobravis (name alternative) (742) + TX, Steinernema scapterisci (name

alternative) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA It is 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 , diflubenzurone (250) + TX, dimatife (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methotype [CCN] + TX, methyl afolate [CCN] + TX, slurry [CCN] + TX, penflurone (alternative name) [CCN] + TX, tepa [CCN] + TX, thio-hempa (alternative name) [CCN] + TX, tiotepa (alternative name) [ CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

Petition 870190098775, of 10/02/2019, p. 83/162

71/144 an insect pheromone selected from the group of substances consisting of (E) -dec-5-en-l-yl acetate with (E) -dec-5-en-l-ol (IUPAC name) ( 222) + TX, (E) tridec-4-en-l-yl acetate (IUPAC name) (829) + TX, (E) -6-methyl-hept2-en-4-ol (IUPAC name) (541 ) + TX, (E, Z) ~ tetradeca-4,1O-dien-l-yl acetate (IUPAC name) (779) + TX, (Z) -dodec-7-en-l-yl acetate (name IUPAC) (285) + TX, (Z) hexadec-11-enal (IUPAC name) (436) + TX, (Z) hexadec-11-en-l-yl acetate (IUPAC name) (437) + TX, (Z) hexadec-13-en-l1-in-l-yl acetate (IUPAC name) (438) + TX, (Z) -icos13-en-10-one (IUPAC name) (448) + TX, ( Z) -tetradec-7-en-lal (IUPAC name) (782) + TX, (Z) -tetradec-9-en-l-ol (IUPAC name) (783) + TX, (Z) -tetradec acetate -9-en-l-yl (IUPAC name) (784) + TX, (7E, 9Z) acetate -dodeca-7,9-dien-l-yl (IUPAC name) (283) + TX, ( 9Z, 11E) -tetradeca-9,11dien-l-ila (IUPAC name) (780) + TX, (9Z, 12E) acetate tetradeca-9,12-dien-l-ila (IUPAC name) (781) + TX, 14methyloctadec-l-eno (IUPAC name) (545) + TX, 4-methylnonan-5ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alfamultistriatina (alternative name) [CCN] + TX, brevicomina (alternative name) [ CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemona (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8 acetate -en-l-ila (IUPAC name) (286) + TX, dodec-9-en-l-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-l acetate -ila (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalina (alternative name) [CCN] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) +

Petition 870190098775, of 10/02/2019, p. 84/162

72/144

TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX , litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl-eugenol (alternative name) ( 540) + TX, muscalure (563) + TX, octadeca acetate-2,13-dien-l-ila (IUPAC name) (588) + TX, octadeca acetate-3,13-dien-l-ila (name IUPAC) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine ( alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-l-ila acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure Bi (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc -call (alternative name) [CCN] + TX, an insect repellent selected from the group of substances consisting of 2- (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, dimethyl phthalate [CCN] + TX, ethylhexanediol (1137) + TX,

Petition 870190098775, of 10/02/2019, p. 85/162

73/144 hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, an insecticide selected from the group of substances consisting of 1 -dichloro-l-nitroethane (name lUPAC / Chemical Abstracts) (1058) + TX, 1, 1-dichloro-2,2bis (4-ethylphenyl) ethane (IUPAC name) (1056), + TX, 1,2dichloropropane (name lUPAC / Chemical Abstracts) (1062) + TX,

1.2- dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1-bromo-2-chloroethane (lUPAC / Chemical name

Abstracts) (916) + TX, 2,2,2-trichloro-1- (3,4dichlorophenyl) ethyl acetate (IUPAC name) (1451) + TX, 2,2dichlorovinyl 2-ethylsulfinylethylmethyl phosphate (IUPAC name) (1066 ) + TX, 2- (1,3-dithiolan-2-yl) phenyl dimethylcarbamate (lUPAC / Chemical Abstracts name) (1109) + TX, 2- (2butoxyethoxy) ethyl thiocyanate (lUPAC / Chemical Abstracts name) (935 ) + TX, 2- (4,5-dimethyl-1,3-dioxolan-2yl) phenyl (name lUPAC / Chemical Abstracts) methylcarbamate (1084) + TX, 2- (4-chloro-3,5-xylyloxy) ethanol ( IUPAC name) (986) + TX, diethyl 2-chlorovinyl phosphate (IUPAC name) (984) + TX, 2imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindane-

1.3- dione (IUPAC name) (1246) + TX, 2-methyl (prop-2-inyl) aminophenyl methyl (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX , 3bromo-l-chloroprop-l-ene (IUPAC name) (917) + TX, 3-methyl-l-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl methylcarbamate (prop -2inyl) amino-3,5-xylyl (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-l-enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, Acephate (2) + TX,

Petition 870190098775, of 10/02/2019, p. 86/162

74/144 acetamipride (4) + TX, acetione (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, alf a-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidithione (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasin (877) + TX, atidationa (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadiractin (alternative name) (41) + TX, azametiphos (42) + TX, azinfosethyl (44) + TX, azinfosmethyl (45) + TX, nitrogen ( 889) + TX, Bacillus thuringiensis delta-endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (no me lUPAC / Chemical Abstracts) (892) + TX, bartrine [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58 ) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioalectrin (78) + TX, S-cyclopentenyl isomer of bioalectrin (alternative name) (79) + TX, bioethanometrine [CCN] + TX, biopermetrin (908) + TX, bioresmethrin (80) + TX, bis (2-chloroethyl) ether (IUPAC name) ( 909) + TX, bif rif lurona (83) + TX, borax (86) + TX, brof envalerato (alternative name) + TX, bronf envinfós (914) + TX, bromocyclene (918) + TX, bromo-DDT ( alternative name) [CCN]

Petition 870190098775, of 10/02/2019, p. 87/162

75/144 + TX, bromophos (920) + TX, bromophosethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butatiofós (927) + TX, butocarboxime (103) + TX, butonate (932) + TX, butoxycarboxime (104) + TX, butylpyridabene (alternative name) + TX, cadusafós (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphochlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (lUPAC name / Chemical Abstracts) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenothione (947) + TX, carbosulfan (119) + TX, cartape (123) + TX, cartape hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclene (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964 ) + TX, chlorethoxyphos (129) + TX, chlorophenapyr (130) + TX, chlorofenvinphos (131) + TX, chlorfluazurome (132) + TX, cl ormefós (136) + TX, chloroform [CCN] + TX, chloropicrina (141) + TX, chlorfoxime (989) + TX, chlorprazophos (990) + TX, chloropyriphos (145) + TX, chloropyriphos-methyl (146) + TX , chlorothiophos (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, coumafós (174) + TX, coumitoato (1006) + TX, crotamitona (alternative name) [CCN] + TX, crotoxifós (1010) + TX, crufomato (1011 ) + TX, cryolite

Petition 870190098775, of 10/02/2019, p. 88/162

76/144 (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanophenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cyclethrin [CCN ] + TX, cycloprotine (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, dazomete (216) + TX, DDT ( 219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefiona (1037) + TX, demefiona-0 (1037) + TX, demefiona-S (1037) + TX, demetona (1038) + TX , demetone-methyl (224) + TX, demetone-0 (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialiphos (1042) + TX, diamidaphos (1044) + TX, diazinone (227) + TX, dicapton (1050) + TX, diclofentiona (1051) + TX, dichlorvos (236) + TX, diclifós (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanyl (244) + TX, dieldrin (1070) + TX, 5-methylpyrazol-3-yl diethyl phosphate ( IUPAC name) (1076) + TX, diflubenzurone (250) + TX, dilor (alternative name) [CCN] + TX, dimeflutrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimetoate ( 262) + TX, dimethrin (1083) + TX, dimethylinfin (265) + TX, dimethylane (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprope (1093) + TX , dinosame (1094) + TX, dinosebe (1095) + TX, dinotefuran (271) + TX, diophenolane (1099) + TX, dioxabenzofós (1100) + TX, dioxacarb (1101) + TX, dioxationa (1102) + TX, disulfotone (278) + TX, dithyrophos (1108) +

Petition 870190098775, of 10/02/2019, p. 89/162

77/144

TX, DNOC (282) + TX, doramectin (name alternative) [CCN] + TX, DSP (1115) + TX, ecdysterone (name alternative) [CCN] + TX, El 1642 (development code) (1118) + TX,

emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endothionin (1121) + TX, endrine (1122) + TX , EPBP (1123) + TX, EPN (297) + TX, epophenonane (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esf envalerato (302) + TX, etafós (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethione (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, etrinfós (1142) + TX, EXD (1143) + TX, fanfur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, fenencaphos (1148) + TX, fenetacarb (1149) + TX, fenflutrina (1150) + TX, fenitrothione (335) + TX, fenobucarb (336) + TX, fenoxacrime (1153) + TX, fenoxicarb (340) + TX, fenpiritrina (1155) + TX, fenpropatrina (342) + TX , fenpi rade (alternative name) + TX, fensulfothione (1158) + TX, fentiona (346) + TX, fentiona-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendiamide (No. CAS Reg .: 272451-65-7) + TX, flucofurone (1168) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenorim [CCN] + TX, flufenoxurone (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, phonophos (1191) + TX, formethanate (405 ) + TX, formethanate hydrochloride (405) +

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78/144

TX, formothione (1192) + TX, formparanate (1193) + TX, phosmethylane (1194) + TX, phospirate (1195) + TX, phostiazate (408) + TX, fostietane (1196) + TX, furatiocarb (412) + TX , furetrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamaHCH (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, hexaflumurone (439) + TX, HHDN (864) + TX, hydramethylnone (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquincarb (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, isophenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, 0- (methoxyminothiophosphoryl) is salicylate opropyl (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathione (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmine I (696) + TX , Jasmine II (696) + TX, iodophenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [ CCN] + TX, quelevano (1249) + TX, quinoprene (484) + TX, lambda-cyhalotin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250 ) + TX, lindane (430) + TX, lyrinphos (1251) + TX, lufenurone (490) + TX, lithidathione (1253) + TX, mcumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (name IUPAC) (640) + TX, malathion (492) + TX, malonobene (1254)

Petition 870190098775, of 10/02/2019, p. 91/162

79/144 + TX, mazidox (1255) + TX, mecarbame (502) + TX, mecarphone (1258) + TX, menazone (1260) + TX, mefosfolane (1261) + TX, mercury chloride (513) + TX, mesulfenphos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacryphos (1266) + TX, metamidophos (527) + TX, methanesulfonyl fluoride (name lUPAC / Chemical Abstracts) (1268) + TX, methidathione (529) + TX, metiocarb (530) + TX, metocrotofós (1273) + TX, metomila (531) + TX, methoprene (532) + TX, methoxy-butyl (1276) + TX, methotrine (alternative name) (533) + TX, methoxychloride (534) + TX, methoxy enozide (535) + TX, methyl bromide (537) + TX , methyl isothiocyanate (543) + TX, methyl chloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metoflutrin [CCN] + TX, metolcarb (550) + TX, methoxyzone (1288) + TX , mevinfós (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafo x (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nalede (567) + TX, naphthalene (lUPAC / Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nitiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1: 1 zinc chloride ( 1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novalurone (585) + TX, noviflumurone (586) + TX, ethylphosphonothioate

Petition 870190098775, of 10/02/2019, p. 92/162

80/144

0-5-dichloro-4-iodophenyl Q-ethyl (IUPAC name) (1057) + TX, 0.0-diethyl-0-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name ) (1074) + TX, 0, Q-diethyl-Q-6methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, 0.0, O 'dithiopyrophosphate, O'-tetrapropyl ( IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxemetone-methyl (609) + TX, oxideprofos (1324) + TX , oxydisulfotone (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathione (615) + TX, parat ion-methyl (616) + TX, penflurone (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, fencaptona (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmete (638) + TX, phosnichlor (1339) + TX, phosphamidon a (639) + TX, phosphine (IUPAC name) (640) + TX, foxime (642) + TX, phoxymethyl (1340) + TX, pyrimetafós (1344) + TX, pirimicarb (651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX , potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidofós (1349) + TX, profenofós (662) + TX, proflutrina [CCN] + TX, promacila (1354) + TX, promecarb (1355) + TX, propafós (1356) + TX, propetanfós (673) + TX, propoxur (678) + TX, protidationa

Petition 870190098775, of 10/02/2019, p. 93/162

81/144 (1360) + TX, protiofós (686) + TX, protoato (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, piraclofós (689) + TX, pyrazofós (693) + TX , pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalil (700) + TX, pyridafentiona (701) + TX, pyrimidiphene (706) + TX, pyrimitate (1370) + TX, pyriproxyphene (708) + TX, kassia (alternative name) [CCN] + TX, quinalphos (711) + TX, quinalphos-methyl (1376) + TX, quinothione (1380) + TX, quintiofós (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, ryan (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX , sabadila (alternative name) (725) + TX, escradano (1389) + TX, sebufós (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI- 0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (name lUPAC / Chemical 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, spirotetramate (CCN) + TX, sulcofurone (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotepe (753) + TX, sulfuryl fluoride (756) + TX,

Petition 870190098775, of 10/02/2019, p. 94/162

82/144 sulprofós (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpirada (763) + TX, tebupirinfós (764) + TX, teflubenzurone (768) + TX, teflutrina (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teraletrina (1418) + TX, terbame (alternative name) + TX, terbufós (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinfós (777) + TX, tetramethrin (787) + TX, tetacipermethrin (204) + TX, thiaclopride (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrofós (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocycline hydrogen oxalate (798) + TX, thiodicarb (799 ) + TX, thiophanox (800) + TX, thiometone (801) + TX, thionazine (1434) + TX, thiosultime (803) + TX, thiosultult sodium (803) + TX, thuringensin (alternative name) [CCN] + TX, tolfenpirade (809) + TX, tralometrine (812) + TX, transflutrin (813) + TX, transpermetrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, trichlorophone (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronate ( 1452) + TX, triphenophos (1455) + TX, triflumurone (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidothione (847) + TX, vaniliprol [CCN] + TX, veratridine (name alternative) (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, zolaprofós (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprol [736994-63-19] + TX, chlorantraniliprol [500008-45-7] + TX, cyienopyraphene

Petition 870190098775, of 10/02/2019, p. 95/162

83/144 [560121-52-0] + TX, ciflumetofeno [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, spinetorame [18716640-1 + 187166-15-0] + TX, spirotetramate [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0] + TX, meperflutrin [915288-13-0] + TX, tetramethylflutrine [84937-88- 2] + TX, triflumezopyrime (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 , methocarb (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 (name lUPAC / Chemical Abstracts) (1045) + TX, 1,2-dichloropropane (name l UPAC / Chemical Abstracts) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3dichloropropene (233) + TX, 3,4-dioxide -dichlorotetrahydrothiophene (lUPAC / Chemical Abstracts name) (1065) + TX, 3 (4-chlorophenyl) -5-methylrodanine (IUPAC name) (980) + TX,

Petition 870190098775, of 10/02/2019, p. 96/162

84/144 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, benomile ( 62) + TX, but ilpiridabene (alternative name) + TX, cadusafós (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrina (141) + TX , chloropyrifos (145) + TX, cloetocarb (999) + TX, cytokinins (alternative name) (210)

+ TX, dazomete (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafós (1044) + TX, diclofentiona (1051) + TX, diclifós (name alternative) + TX, dimethoate (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, fenpirade (alternative name) + TX, fensulfothione (1158) + TX, phostiazate (408) + TX, fostietano (1196) + TX, furfural (alternative name) [CCN] + TX , GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (name alternative) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, potassium metam (alternative name) (519) + TX, metamesode (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 (name alternative) (565) + TX, NC-184 (compound code) + TX, oxamyl (602)

Petition 870190098775, of 10/02/2019, p. 97/162

85/144 + TX, phorate (636) + TX, phosphamidone (639) + TX, phosphocarb [CCN] + TX, sebufós (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbame (alternative name) + TX, terbufós (773) + TX, tetrachlorothiophene (lUPAC / Chemical Abstracts name) (1422) + TX, tiafenox (alternative name) + TX, thionazine (1434) + TX, triazofós (820 ) + TX, triazurone (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX, a nitrification inhibitor selected from the group of substances consisting of potassium 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 (name IUPAC) (1246) + TX, 4- (quinoxalin-2ylamino) benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX , arsenious oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide ( 444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumaclor (1004) + TX, coumafurila (1005) + TX, coumatetralila (175) + TX , crimidine (1009) + TX, difenacoum (246) + TX, difetialone (249) + TX, difacinone (273) + TX,

Petition 870190098775, of 10/02/2019, p. 98/162

86/144

ergocalciferol (301) + TX, flocoumafeno (357) + TX fluoroacetamide (379) + TX, flupropadine (1183) + TX

flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, fosacetime (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinurone (1371) + TX, escilirosida (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444 ) + TX, sodium fluoroacetate (735) +

TX, strychnine (745) + TX, sulfate thallium [CCN] + TX, warfarin (851) and phosphide in zinc (640) + TX, an agent synergistic selected a leave of the group of substances consisting piperonylate in 2- (2-

butoxyethoxy) ethyl (IUPAC name) (934) + TX, 5- (1,3benzodioxol-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, diazinone (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, metiocarb (530) + TX, pyridin-4

Petition 870190098775, of 10/02/2019, p. 99/162

87/144 amine (IUPAC name) (23) + TX, thiram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and zirame (856) + TX, a virucide selected from the group of substances consisting of 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, octyline (590) and thiophanate -methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole [865318-97-4] + TX, amisulbrome [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzovindiflupir [1072957-71-1] + TX, bitertanol [7058536-3] + 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 [23841011-2] + TX, epoxiconazole [106325 -08-0] + TX, fenbuconazole [114369-43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, fluxpyroxade [90720431-3] + TX, fluopyram [658066-35- 4] + TX, phenaminstrobin [366815-39-6] + TX, isofetamide [875915-78-9] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08-1] + TX, isothianyl [224049-04-1] + TX, mandestrobin [173662-97-0 ] (can be prepared according to the procedures described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30

Petition 870190098775, of 10/02/2019, p. 100/162

88/144

4] + TX, penflufen [494793-67-8] + TX, penconazole [6624688-6] + 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, triadimefone [43121-43-3] + TX, triadimenol [55219-653] + TX, triflumizole [99387-89-0] + TX, triticonazole [13198372-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [6016888-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [4148343-6] + TX, dimethyrimol [5221-53-4] + TX, ethirimol [2394760-6] + TX, dodemorph [1593-77-7] + TX, phenpropidine [6730600-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43- 3] + TX, cyprodinil [121552-61-2] + TX, mepanipyrime [110235-47-7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [7473817-3] + TX, fludioxonila [131341 -86-1] + TX, fluindapyr [1383809-87-7] + TX, benalaxyl [71626-11-4] + TX, furalaxyl [57646-30-7] + TX, metala xila [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomila [17804- 35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX , chlozolinate [84332-86-5] + TX, diclozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16 -8] + TX, vinclozoline [50471-44-

8] + TX, boscalida [188425-85-6] + TX, carboxine [5234-68 4] + TX, fenfurame [24691-80-3] + TX, flutolanil [66332-96 5] + TX, flutianila [958647-10-4] + TX, mepronila [55814-41 0] + TX, oxycarboxine [5259-88-1] + TX, pentiopirade [183675

82-3] + TX, tifluzamide [130000-40-7] + TX, guazatin

Petition 870190098775, of 10/02/2019, p. 101/162

89/144 [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, orizastrobin [24859316-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, piraoxystrobin [86258811-2 ] + TX, ferbame [14484-64-1] + TX, mancozebe [8018-017] + TX, manebe [12427-38-2] + TX, metamil [9006-42-2] + TX, propineb [12071- 83-9] + TX, thiram [137-26-8] + TX, zinebe [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX , captano [133-06-2] + TX, dichlofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folet [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, dinocape [131-72 -6] + TX, nitrotal-isopropyl [ 10552-74-6] + TX, edifenfós [17109-49-8] + TX, iprobenfós [26087-47-8] + TX, isoprothiolan [50512-35-1] + TX, phosdifene [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofós-methyl [57018-049] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX , bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloronebe [2675-77-6] + TX, chlorothalonil [1897 -45-6] + TX, cyflufenamide [180409-60-3] + TX, cymoxanil [5796695-7] + TX, diclone [117-80-6] + TX, diclocimete [139920-32

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90/144

4] + TX, diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, dietofencarb [87130-20-9] + TX, dimetomorph [11048870-5] + TX, SYP-LI90 (Flumorfe) [211867-47-9] + TX, dithianone

[3347-22-6] + TX, etaboxame [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, phenamidone [161326-34- 7] + TX, phenoxani la [115852-48- -7] + TX, fentina [668-34-8] + TX, ferinzona [89269-64-7] + TX, fluaziname

[79622-59-6] + TX, fluopicolid [239110-15-7] + TX, flussulfamide [106917-52-6] + TX, phenhexamide [126833-178] + TX, phosethyl aluminum [39148-24 -8] + TX, himexazole [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (cyzofamide) [120116-88-3] + TX, casugamycin [6980-18- 3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencicurone [66063-05-6] + TX, phthalide [27355-22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12-4 ] + TX, pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyrokylone [57369-32-1] + TX, pyrophenone [688046-61-9] + TX, pyribencarb [ 799247-52-2] + TX, pyrisoxazole [847749-37-5] + TX, quinoxyphene [12449518-7] + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX , Timorex Gold ™ (plant extracts containing tree oil from the Stockton Group) + TX, tebufloquine [376645-78-2] + TX, thiadinyl [22358 0-51-6] + TX, triazoxide [72459-58-6] + TX, tolprocarb [911499-62-2] + TX, triclopyricarb [902760-40-1] + TX, tricyclazole [41814-782] + TX , triforin [26644-46-2] + TX, validamycin [3724847-8] + TX, valiphenalate [283159-90-0] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamide [374726- 62-2] +

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TX, isopyrazame [881685-58-1] + TX, phenamacryl + TX, silkxane [874967-67-6] + TX, trinexapac-ethyl [95266-40-3] + TX, (9-dichloromethylene-1,2, 3-Difluoromethyl-1-methyl-1Hpyrazol-4-carboxylic acid 3,4-tetrahydro-1,4-methanonaphthalen-5-yl (disclosed in WO 2007/048556) + TX, (3 ', 3difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid 4 ', 5'-trifluoro-biphenyl-2-yl (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, 12bdeca-hydro-6,12-dihydroxy-4 , 6a, 12b-trimethyl-ll-oxo-9- (3pyridinyl) -2H, llHnafto [2,1-b] pyran [3,4-e] pyran-4-yl] methylcyclopropanecarboxylate [915972-17-7] + TX and 1,3,5-trimethylN- (2-methyl-1-oxopropyl) -N- [3- (2-methylpropyl) -4- [2,2,2trifluoro-1-methoxy-l- (trifluoromethyl) ethyl ] phenyl] -1Hpyrazolo-4-carboxamide [926914-55-8] + TX, or a biologically active compound selected from the group consisting of N - [(5-chloro-2-isopropylphenyl) methyl] -N-cyclopropyl- 3- (difluoromethyl) -5-fluoro-1methyl-pyr azole-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6Dimethi-1H, 5H- [1,4] dithiine [2,3-c: 5.6 -c '] dipyrrol1,3,5,7 (2H, 6H) -tetrone (can be prepared according to the procedures described in WO 2011/138281) + TX, 6-ethyl-5,7dioxo-pyrrole [4,5 ] [1,4] dithiine [1,2-c] isothiazole-3carbonitrile + TX, 4- (2-bromo-4-fluoro-phenyl) -N- (2-chloro-6fluoro-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, 1,3trimethyl-indan-4 -yl) -1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO

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2012/084812) + TX, CAS 850881-30-0 + TX, Ι, (-dioxide of 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] -2methoxy-N-methyl-acetamide + TX, 3- (4,4- difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl) quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2- [2-fluoro-6 - [(8 -fluoro-2-methyl-3quinolyl) oxy] phenyl] propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, 2 [2 - [(7,8-difluoro-2 -methyl-3-quinolyl) oxy] -6-fluorophenyl] propan-2-ol (can be prepared according to the procedures described in WO 2011/081174) + TX, oxatiapiproline + TX [1003318-67-9], N - [6 - [[[((1-methyltetrazol-5-yl) -phenyl-methylene] amino] oxymethyl] -2pyridyl] tert-butyl carbamate + TX, N- [2- (3,4difluorophenyl) phenyl] -3- ( trifluoromethyl) pyrazine-2carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3 (difluoromethyl) -1-methyl-N - [(3R) -1,1,3-trimethylindan-4yl] pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, N- [2methyl-1 - [[((4-methylbenzoyl) amino] methyl] propyl] carbamate

2,2,2-trifluoroethyl + TX, (2RS) -2- [4- (4-chlorophenoxy) - a, a, a-trifluoro-o-tolyl] -1- (1H-1,2,4-triazole -l-yl) propan-2ol + TX, (2RS) -2- [4- (4-chlorophenoxy) -a, a, a-trifluoro-otolyl] -3-methyl-1- (1H-1,2, 4-triazol-1-yl) butan-2-ol + TX, 2 (difluoromethyl) -N - [(3R) -3-ethyl-1,1-dimethyl-indan-4yl] pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N- [3ethyl-1,1-dimethyl-indan-4-yl] pyridine-3-carboxamide + TX,

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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] methanesulfonate - [3,5bis (difluoromethyl) pyrazol-1-yl] acetyl] -4-piperidyl] thiazol4-yl] -4,5-dihydroisoxazol-5-yl] -3-chloro-phenyl] (can be prepared from according to the procedures described in WO 2012/025557) + TX, N- [6 - [[(Z) - [(l-methylthetrazol-5-yl) phenyl-methylene] amino] oxymethyl] -2-pyridyl] carbamate but3-inyl (can be prepared according to the procedures described in WO 2010/000841) + TX, 2 - [[3- (2-chlorophenyl) -2 (2,4-difluorophenyl) oxiran-2-yl] methyl] -4H-1,2,4-triazol-3thione (can be prepared according to the procedures described in WO 2010/146031) + TX, N - [[5- [4- (2,4dimethylphenyl) triazol-2-yl ] -2-methyl-phenyl] methyl] methyl carbamate + TX, 3-chloro-6-methyl-5-phenyl-4- (2,4, 6trifluorophenyl) pyridazine (can be prepared according to procedures described in WO 2005/121104) + TX, 2- [2 chloro-4- (4-chlorophenoxy) phenyl] -1- (1,2,4-triazol-1-yl) propan2-ol (can be prepared according to with the procedures described in WO 2013/024082) + TX, 3-chloro-4- (2,6difluorophenyl) -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-phenylpyridazine-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-4yl] pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2011/162397) + TX, 3Petition 870190098775, of 02/10 / 2019, p. 106/162

94/144 (difluoromethyl) -N- (7-fluoro-1,2,3-trimethyl-indan-4-yl) -1methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012 / 084812) + TX, 1 [2- [[1- (4-chlorophenyl) pyrazol-3-yl] oxymethyl] -3-methyl-phenyl] 4-methyl-tetrazol-5-one (can be prepared according to procedures described in WO 2013/162072) + TX, 1-methyl-4 [3-methyl-2 - [[2-methyl-4- (3,4,5-trimethylpyrazol-lil) phenoxy] methyl] phenyl] tetrazole- 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- (4-phenoxyphenyl) methyl N, 3-dimethyl-pent-3-enamide + TX, (4-phenoxyphenyl) methyl + TX, N- (5chloro-2-isopropylbenzyl) -N-cyclopropyl-3-amino-6-methylpyridine-3-carboxylate - (difluoromethyl) -5fluoro-1-methylpyrazol-4-carboxamide [1255734-28-1] (can be prepared according to the procedures described in WO 2010/130767) + TX, 3- (difluoromethyl) -N - [( R) -2,3-dihydro-

1,1,3-trimethyl-1H-inden-4-yl] -1-methylpyrazol-4-carboxamide [1352 994-67-2] + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl ) -N- ethyl-N-methyl-formamidine + TX, Ν '- [4- (4,5-dichloro-thiazol-2yloxy) -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-dimethylphenyl] -N-ethyl-N-methyl-formamidine + TX,

^u (fenpicoxamide [517875-34-2]) +

TX (as described in WO 2003/035617), 2- (difluoromethyl) N- (1,1, 3-trimethylindan-4-yl) pyridine-3-carboxamide + TX, 2

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95/144 (difluoromethyl) -N- (3-ethyl-1,1-dimethyl-indan-4-yl) pyridine3-carboxamide + TX, 2- (difluoromethyl) -N- (1,1-dimethyl-3propyl-indan -4-yl) pyridine-3-carboxamide + TX, 2 (difluoromethyl) -N- (3-isobutyl-1,1-dimethyl-indan-4yl) 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, in which each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and / or WO 2016/139189.

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

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Most of the active ingredients described above are referred to earlier by a so-called common name, the relevant ISO common name or another common name being used in individual cases. If the designation is not a common name, the nature of the designation used instead is given in curly brackets for the particular compound; in that case the name IUPAC, the name lUPAC / Chemical Abstracts, a chemical name, a traditional name, a compound name or a development code is used or, if neither of these designations nor a common name is used, a alternate name. In CAS Registry it means the Chemical Abstracts Registration Number.

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

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

Mixtures comprising a compound 1.1 to 1.28 described in Table TI or a compound of Formula (I) described in Tables 1.1 to 1.5 or tables 2.1 to 2.9 (below) and one or more active ingredients as described above can be applied, for example , in a single ready-mix form, in a combined spray mixture composed of separate formulations of the components of the individual active ingredients, such as a mixing tank, and in a combined use of the individual active ingredients when applied in a sequential manner, ie , one after the other within a reasonably short period, such as a few hours or days. The order of application of the compound of Formula (I) selected from those described in Tables 1.1 to 1.5 or 2.1 to 2.9 (below), or Table TI (below), and the active ingredient (s) such as described above, is not essential to the practice of the present invention.

The compositions according to the invention may also comprise additional solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example coconut oil, rapeseed oil or epoxidized soybean oil), defoamers, for example oil silicone, preservatives, viscosity regulators,

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98/144 binders and / or adhesives, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

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

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

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

Means of control or prevention that reduce infestation by microorganisms or phytopathogenic or deteriorating organisms that are potentially harmful to man, especially fungal organisms, to such a degree that an improvement can be demonstrated.

A preferred method for controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which comprises the application of a compound of Formula (I), or an agrochemical composition containing at least one of compounds, is the 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) can also penetrate the plant through the roots via the soil (systemic action) by soaking the plant's locus with a Formulation

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100/144 liquid, or by applying the compounds in solid form to the soil, eg in granular form (application to soil). In irrigated rice crops, such granules can be applied to the irrigated rice field. The compounds of Formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

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

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 10 mg to 1 g of active substance per kg of seeds.

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

Suitably, a composition comprising a compound of Formula (I) according to the present invention is applied preventively, which means before the

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101/144 disease development, or dressing, which means after disease development.

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 capable of flowing for treatment seed (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 emulsifiable concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a microemulsion (ME), an oil dispersion (OD), an oil miscible fluid (OF), an oil miscible liquid (OL), a concentrate soluble (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wetting powder (WP) or any technically possible formulation in combination with agriculturally acceptable adjuvants.

Such compositions can be produced in a conventional manner, eg by mixing the active ingredients with appropriate formulation aggregates (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, antifreeze, adherents, thickeners and compounds that provide adjuvant effects). Conventional slow release formulations can also be employed when effectiveness is desired

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102/144 lasting. Particularly, Formulations to be applied in spray forms, such as water dispersible concentrates (eg EC, SC, DC, OD, SE, EW, EO and the like), wetting powders and granules, may contain surfactants as wetting agents and dispersants and other compounds that provide adjuvant effects, for example, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, a lignin sulfonate, a fatty alkyl sulfate, and an ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed cover formulation is applied in a manner known per se to the seeds using the combination of the invention and a diluent in the form of a suitable seed cover form, e.g., as an aqueous suspension or in a dry powder form. having good adhesion to the seeds. Such seed cover formulations are known in the art. Seed cover formulations can contain the individual active ingredients or the combination of active ingredients in an encapsulated form, eg as slow release capsules or microcapsules.

In general, formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of agriculturally acceptable surfactant, and from 10 to 99.99% of solid or liquid 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. The concentrated forms of the compositions generally contain, between about 2 and 80%, preferably between about 5

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103/144 and 70% by weight of active agent. The application forms of the formulation can for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Although commercial products are preferably formulated as concentrates, the end user will normally employ diluted formulations.

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

Table 1.1: This table discloses 22 specific compounds of formula (T-1):

where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is hydroxy and NR ⁴ (R ⁵ ) is as defined below in Table 1.

Each of Tables 1.2 to 1.5 (which follow Table 1.1) makes 22 individual compounds of formula (ΤΙ) available in which A, R ¹ , R ² , and R ³ are as specifically defined in Tables 1.2 to 1.5, which are refer to Table 1, where -NR ⁴ (R ⁵ ) is specifically defined.

Table 1

Compost the number -NR ⁴ (R ⁵ ) Compost the number -NR ⁴ (R ⁵ ) 1,001 azetidinyl 1,012 N-ethoxy-N- isopropylamino 1,002 N- [2- (dimethylamino) ethyl] -N-methylamino 1,013 N-cyclopropyl-Netylamino

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1,003 N- (2-cyanoethyl) -Netylamino 1,014 oxazolidinyl 1,004 N- (cyclopropylmethyl) - N-propylamino 1,015 N-methyl-N-prop-2inylamino 1,005 N, N- (di-2- methoxyethyl) amino 1,016 N-ethoxy-N- methylamino 1,006 N-methyl-N- cyanomethylamino 1,017 N-methyl-N-2,2,2trifluoroethylamin o 1,007 N-methyl-N-prop-2enylamino 1,018 N-2-methoxyethyl-Nmethylamino 1,008 N, N-diethylamino 1,019 N-oxetan-3-yl-N- methoxyamino 1,009 isoxazolidinyl 1,020 N- cyclopropylmethyl- N-methylamino 1,010 N, N- (di-prop-2enyl) amino 1,021 N-cyclopropylethyl- N-methylamino 1,011 N-cyclopropyl-N (2.2- difluoroethyl) amino 1,022 N-ethyl-N- methylamino

Table 1.2: This table discloses 22 specific compounds of formula (Tl), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is ethoxy and -NR ⁴ (R ⁵ ) is as defined above in Table 1.

Table 1.3: This table discloses 22 specific compounds of formula (Tl), where A is 1,4-phenylene, R ¹ and R ² are

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105/144 hydrogen, R ³ is propyl and -NR ⁴ (R ⁵ ) is as defined above in Table 1.

Table 1.4: This table discloses 22 specific compounds of formula (Tl), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is cyclopropyl and -NR ⁴ (R ⁵ ) is as defined above in Table 1.

Table 1.5: This table discloses 22 specific compounds of formula (Tl), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is 2,2,2-trifluoroethyl and -NR ⁴ (R ⁵ ) is as defined above in Table 1.

Table 2.1: This table discloses 23 specific compounds of formula (T-2):

where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is isopropyl and NR ⁴ (R ⁵ ) is as defined below in Table 2.

Each of Tables 2.2 to 2.9 (which follow Table 2.1) makes available 23 individual compounds of the formula (T2) in which A, R ¹ , R ² , and R ³ are as specifically defined in Tables 2.2 to 2.9, which refer to Table 2, where -NR ⁴ (R ⁵ ) is specifically defined.

Table 2

Compost the number -NR ⁴ (R ⁵ ) Compost the number -NR ⁴ (R ⁵ ) 2,001 azetidinyl 2,013 N-cyclopropyl-Netylamino

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2,002 N- [2- (dimethylamino) ethyl] -N-methylamino 2,014 oxazolidinyl 2,003 N- (2-cyanoethyl) -Netylamino 2,015 N-methyl-N-prop-2inylamino 2,004 N- (cyclopropylmethyl) - N-propylamino 2,016 N-ethoxy-N- methylamino 2,005 N, N- (di-2methoxyethyl) amino 2,017 N-methyl-N-2,2,2trifluoroethylamin o 2,006 N-methyl-N- cyanomethylamino 2,018 N-2-methoxyethyl-Nmethylamino 2,007 N-methyl-N-prop-2- enilamino 2,019 N-oxetan-3-yl-N- methoxyamino 2,008 N, N-diethylamino 2,020 N- cyclopropylmethyl- N-methylamino 2,009 isoxazolidinyl 2,021 N-lcyclopropylethylN-methylamino 2,010 N, N- (di-prop-2enyl) amino 2,022 N-ethyl-N- methylamino 2 . 011 N-cyclopropyl-N (2.2- difluoroethyl) amino 2,023 N, N-dimethylamino 2,012 N-ethoxy-N- isopropylamino

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Table 2.2: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is isobutyl and -NR ⁴ (R ⁵ ) is as defined above in Table 2.

Table 2.3: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is prop-2-enyl and -NR ⁴ (R ⁵ ) is as defined above in Table 2.

Table 2.4: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is prop-2-inyl and -NR ⁴ (R ⁵ ) is as defined above in Table 2.

Table 2.5: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is propyloxy and -NR ⁴ (R ⁵ ) is such as defined above in Table 2.

Table 2.6: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is butyloxy and -NR ⁴ (R ⁵ ) is such as defined above in Table 2.

Table 2.7: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is methoxyethyl and -NR ⁴ (R ⁵ ) is such as defined above in Table 2.

Table 2.8: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are hydrogen, R ³ is cyclopropylmethyl and -NR ⁴ (R ⁵ ) is such as defined above in Table 2.

Table 2.9: This table discloses 23 specific compounds of formula (T-2), where A is 1,4-phenylene, R ¹ and R ² are

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108/144 hydrogen, R ³ is oxetan-3-yl and -NR ⁴ (R ⁵ ) is as defined above in Table 2.

EXAMPLES

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

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

Throughout the present description, temperatures are given in degrees Celsius (° C) and m.p. means melting point. LC / MS stands for Liquid Chromatography Mass Spectroscopy and the description of the devices and method (Methods A, B and C) is as follows:

The description of the LC / MS device and method A is: Waters SQ 2 detector

Ionization method: Electrospray

Polarity: positive and negative ions

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Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00,

Source Temperature (° C) 150, Desolvation Temperature (° C) 350, Cone Gas Flow (L / Hr) 0, Desolvation Gas Flow (L / Hr) 650 Mass range: 100 to 900 Da

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 Solvent B: Acetonitrile + acid 0.05% formic) Time THE (%) B (% ) Flow rate (mL / min) (minutes) 0 100 0 0.85 1.2 0 100 0.85 1.5 0 100 0.85

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

The description of the LC / MS device and method B is: Waters SQ 2 detector

Ionization method: Electrospray

Polarity: positive ions

Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00,

Source Temperature (° C) 150, Desolvation Temperature (° C) 400, Cone Gas Flow (L / Hr) 60, Desolvation Gas Flow (L / Hr) 700 Mass range: 140 to 800 Da

DAD wavelength range (nm): 210 to 400

Waters UPLC ACQUITY method with the following HPLC gradient conditions

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(Solvent A: Water / Methanol 9: 1 + 0.1% formic acid Solvent B : Acetonitrile Ί- acid 0.1% formic) Time Α (%) B (% ) Flow rate (mL / min) (minutes) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75

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

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

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

The description of the LC / MS device and method D is: Waters SQ 2 detector

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Ionization method: Electrospray

Polarity: positive ions

Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00,

Source Temperature (° C) 150, Desolvation Temperature (° C) 400, Cone Gas Flow (L / Hr) 60, Desolvation Gas Flow (L / Hr) 700 Mass range: 140 to 800 Da

DAD wavelength range (nm): 210 to 400

Waters UPLC ACQUITY method with the following HPLC gradient conditions

(Solvent A: Water / Methanol 9: 1, acid 0.1% formic and Solvent B : Acetonitrile, formic acid 0.1%) Time THE (%) B (%) Flow rate (minutes) (mL / min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75

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

Where necessary, the enantiomerically pure final compounds can be obtained from racemic materials as appropriate, via standard physical separation techniques such as reverse chiral chromatography, or through stereoselective synthetic techniques, eg using chiral starting materials.

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Formulation Examples

Wetting powders The) B) ç) Active ingredient [composed of 25% 50% 75% Formula (I)] sodium lignosulfonate 5% 5% - Sodium lauryl sulfate 3% - 5% diisobutylnaphthalenesulfonate of - 6% 10% sodium polyethylene glycol ether of phenol - 2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27% - The active ingredient is completely mixed with adjuvants and the mixture is completely crushed into a mill appropriate, resulting in wetting powders that can be diluted with water to give suspensions concentration desired. Powders for seed treatment a The) B) ç) 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% - Baby powder - - 20%

active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a mill

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113/144 suitable, originating powders that can be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of 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% mixture of xylenes 50%

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

Dust The) B) ç) Active ingredient [5% compound 6% 4% Formula (I)] Baby powder 95% - - Kaolin - 94% - mineral filling - - 96% Ready-made dust to use are obtained by mixture of active ingredient with the carrier and crushing the mixture in

a suitable mill. These powders can also be used for dry seed coating.

Extruder granules

Active ingredient [15% compound

Formula (I)] 2% sodium lignosulfonate

Carboxymethylcellulose 1%

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Kaolin 82% active ingredient is mixed and crushed with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

Coated granules

Active ingredient [8% compound

Formula (I)] polyethylene glycol (p. Mol. 3%

200)

Kaolin 89%

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

Suspension concentrate

Active ingredient [compound of Formula 40% (I)] propylene glycol 10% polyethylene glycol ether 6% nonylphenol (15 mol ethylene oxide)

10% sodium lignosulfonate

Carboxymethylcellulose 1%

Silicone oil (in the form of an emulsion 1% to 75% in water)

Water 32%

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by diluting with water. Using these dilutions, live plants as well as

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Flowable concentrate for seed treatment Active ingredient [compound of Formula (I)] 40% propylene glycol 5% butanol PO / EO copolymer 2% tristyrene phenol 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 an emulsion at 0.2% 75% in water)

Water 45.3%

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by diluting with water. Using these 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 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.

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

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.

The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for that purpose.

List of abbreviations

AIBN = azobisisobutyronitrile BOP-C1 = acid bis (2-oxo-oxazolidide) chloride

phosphoric

CDI = carbonyl di-imidazole DCE = 1,2-dichloroethane D CM = dichloromethane DIPEA = N, N-diisopropylethylamine DMA = dimethylacetamide DMF = dimethylformamide EtOAc = ethyl acetate EtOH = ethyl alcohol HC1 = hydrochloric acid Federal Police = melting point Me OH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide TFAA = trifluoroacetic acid anhydride THF = tetrahydrofuran

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

Example 1: This example illustrates the preparation of Ncyclopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] oxazinane-2-carboxamide (Compound 1.4 from Table Ti)

Step 1: Preparation of N'-hydroxy-4-methyl-benzamidine

NH ₂

To a suspension of 4-methylbenzonitrile (35 g, 0.29 mol) in ethanol (220 ml) and water (440 ml) were added at room temperature hydroxylamine hydrochloride (41.1 g, 0.58 mol), carbonate potassium (65.4 g, 0.47 mol) and 8 hydroxyquinoline (0.22 g, 1.5 mmol). The reaction mixture was heated to 80 ° C for 4 hours. The mixture was cooled to room temperature and diluted with 2N HCl to pH 8. The volatiles were removed under reduced pressure and the reaction contents were filtered, washed with water, and dried under vacuum to provide 39.1 g of the title compound. LC / MS (Method A) retention time = 0.23 minutes, 151.0 (M + H).

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Step 2: Preparation of 3- (p-tolyl) -5- (trifluoromethyl) -1,2,4oxadiazole

To a solution of N'-hydroxy-4-methyl-benzamidine (38.7 g, 0.25 mol) in 2-methyl-tetrahydrofuran (750 ml) was added TFAA at 0 ° C. The reaction mixture was stirred at 15 ° C for two hours and then diluted with water. The organic layer was separated, washed successively with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride, water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (gradient eluent heptane / EtOAc 99: 1 to 90:10) to give 54.1 g of the title compound as a clear oil, which solidified after storage. LC / MS (Method A) retention time = 1.15 minutes, mass not detected.

^Χ Η NMR (400 MHz, CDCl ₃ ) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65.41 (s).

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

A mixture of 3- (p-tolyl) -5- (trifluoromethyl) -1,2,4oxadiazole (56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in

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119/144 tetrachloromethane (480 ml) under argon was heated to 70 ° C. AIBN (4.03 g, 24 mmol) was added and the reaction mixture was stirred at 65 ° C for 18 hours. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 100: 0 to 95: 5) to provide 44.7 g of the title compound as a white oil, mp: 58- 63 ° C.

^X H NMR (400 MHz, CDCl ₃ ) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 32 (s).

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

^X H NMR (400 MHz, CDCl3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 34 (s).

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

To a mixture of 1: 9 ratio of 3— [4 - (bromomethyl) phenyl] -5- (trifluoromethyl) -1,2,4-oxadiazole and 3 [4- (dibromomethyl) phenyl] -5- (trifluoromethyl) - 1,2,4-oxadiazole (10.2 g) in acetonitrile (95 ml), water (1.9 ml) and DIPEA (6.20

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120/144 ml, 35.7 mmol) diethylphosphite (4.7 ml, 35.7 mmol) was added at 5 ° C. The mixture was stirred at 5-10 ° C for two hours, 1M HCl was added and the volatiles were removed under reduced pressure. The resulting white paste was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (eluent gradient cyclohexane: EtOAc 99: 1 to 9: 1) to give 7.10 g of the title compound as a white solid, mp: 58 -63 ° C.

^X H NMR (400 MHz, CDCls) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 32 (s).

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

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

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

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A solution of 3- [4- (bromomethyl) phenyl] -5 (trifluoromethyl) -1,2,4-oxadiazole (2.50 g, 8.1 mmol) in dichloromethane (5 ml) was added over 2 hours at temperature environment to a solution of cyclopropanamine (3.7 g, 65 mmol) and N-ethyl-N-isopropyl-propan-2-amine (1.4 mL, 8.1 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 30 minutes, poured into water and then extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 1: 1) to give 1.18 g of the title compound as a white solid. , LC / MS (Method A) retention time = 0.71 minutes, 300 (M + H).

! H NMR (400 MHz, CDCl ₃ ) δ ppm: 8.06 (d, 2H), 7.49 (d, 2H), 3.92 (s, 2H), 2.18 (m, 1H), 1 , 85 (s 1, 1H), 0.42 (m, 2H), 0.39 (m, 2H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 36 (s).

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

In a dry container, under argon, triphosgene (41 mg) was dissolved in 1,2-dichloroethane (5 mL). The clear solution was cooled to 0 ° C. Then a solution

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122/144 of oxazinane hydrochloride (43 mg) and triethylamine (0.1 ml) in 1,2-dichloroethane (2.5 ml) was added at 0 ° C. The reaction mixture was stirred for 4 hours at room temperature. Then, a solution of N - [[4- [5- (trifluoromethyl) -1, 2,4oxadiazol-3-yl] phenyl] methyl] cyclopropanamine (40 mg) and N, Ndiethylethanamine (0.04 mL) in 1 , 2-dichloroethane (2.5 ml) was added. The resulting mixture was stirred for 18 hours at room temperature. Then, aqueous sodium bicarbonate was added to the reaction mixture. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated. The crude residue was purified by chromatography on silica gel using a cyclohexane / ethyl acetate gradient to give 52 mg of the title compound as a clear oil.

^X H NMR (400 MHz, CDCl ₃ ) δ ppm: 8.08 (d, 2H), 7.44 (d, 2H), 3.93 (m, 2H), 3.51 (m, 2H), 2 , 70 (m, 1H), 1.81 (m, 2H), 1.72 (m, 2H), 0.72 (m, 4H).

Example 2: This example illustrates the preparation of the intermediate N- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] methanamine.

CHo /

A solution of 3- [4- (bromomethyl) phenyl] -5 (trifluoromethyl) -1,2,4-oxadiazole (15 g, 46.9 mmol) in THF (20 mL) was added dropwise at temperature room to a 2M solution of methylamine in THF (120 mL, 234.5 mmol). The mixture was stirred at room temperature for 24

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123/144 hours. The solvent was removed under reduced pressure and the resulting crude material was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 1: 1) to give 10.3 g of the title compound as a transparent oil. LC / MS (Method A) retention time = 0.58 minutes, 258 (M + H).

^Χ Η NMR (400 MHz, CDCl ₃ ) δ ppm: 8.08 (d, 2H), 7.47 (d, 2H), 3.84 (s, 2H), 2.48 (s, 3H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 39 (s).

Example 3: This example illustrates the preparation of the 2,2,2-trifluoro-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] ethanamine intermediate.

HN

I F

F

To a solution of 3- [4- (bromomethyl) phenyl] -5 (trifluoromethyl) -1,2,4-oxadiazole (1.5 g, 4.69 mmol) in dichloromethane (10 mL) was added dropwise N -ethyl-Nisopropyl-propan-2-amine (0.82 mL, 4.69 mmol) followed by 2,2,2-trifluoroethanamine (2.94 mL, 37.5 mmol). The reaction mixture was stirred at room temperature for 24 hours, was poured into water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude residue was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 0: 1) to give 1.53 g of the title compound as a clear oil .

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124/144! Η NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.51 (d,

2H), 4.00 (s, 2H), 3.22 (q, 2H), 1.71 (s, 1H).

Example 4: This example illustrates the preparation of the intermediary

N-propoxy-1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3 yl] phenyl] methanamine

A solution of 3- [4- (bromomethyl) phenyl] -5 (trifluoromethyl) -1,2,4-oxadiazole (1.30 g, 4.06 mmol) in dichloromethane (10 mL) was added dropwise to a solution of O-propylhydroxylamine hydrochloride (3.74 g, 32.5 mmol) and DIPEA (6.40 mL, 36.6 mmol) in dichloromethane (6 mL). The reaction mixture was stirred at room temperature for 24 hours, poured into water and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the resulting crude material was purified by flash chromatography on silica gel (eluent gradient cyclohexane / EtOAc 1: 0 to 1: 1) to give 0.92 g of the title compound as a transparent oil. LC / MS (Method A) retention time = 1.12 minutes, 302 (M + H).

^X H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.02 (d, 2H), 5.70 (s 1, 1H), 4.11 (s, 2H), 3 , 59 (m, 2H), 1.52 (m, 2H), 0.86 (s, 3H).

¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 33 (s).

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Example 5: preparation of 1-ethoxy-3-methyl-3-prop-2-ynyl-l [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methyl] urea (Compound 1.1 of Table Ti)

Step 1: Preparation of N-ethoxy-1- [4- [5- (trifluoromethyl)

1,2,4-oxadiazol-3-yl] phenyl] methanamine

A stirred solution of 3- [4- (bromomethyl) phenyl] -5 (trifluoromethyl) -1,2,4-oxadiazole (2.50 g, 7.82 mmol) in dichloromethane (10 mL) was added dropwise to the at room temperature to a stirred solution of o-ethylhydroxylamine hydrochloride (6.10 g) and N-ethyl-N-isopropyl-propan2-amine (12.3 ml). The mixture was stirred at room temperature for 24 hours. Then, a second portion of o-ethylhydroxylamine hydrochloride (6.10 g) and N-ethyl-Nisopropyl-propan-2-amine (12.3 mL) was added and the mixture was stirred at room temperature for 72 hours . Then, the reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under pressure

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126/144 was reduced and the resulting crude residue was purified by flash chromatography on silica gel (cyclohexane gradient: ethyl acetate) to give 2.03 g of the title compound as a yellow oil.

^X H NMR (400 MHz, CDCl ₃ ) δ ppm: 8.09 (d, 2H), 7.52 (d, 2H), 5.72 (s 1, 1H), 4.11 (s, 2H), 3.68 (q, 2H), 1.10 (t, 3H).

Step 2: Preparation of 1-ethoxy-3-methyl-3-prop-2-ynyl-1 - [[4 [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] urea

N-ethoxy-1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3yl] phenyl] methanamine (50 mg) was dissolved in dichloromethane (0.52 ml) and N, N-dimethylformamide ( 0.17 mL). This suspension was added, at room temperature, in an ICD portion (45 mg). The suspension slowly became a clear solution. The mixture was stirred for 1 hour at room temperature. Then, N-methylpropyl-2-in-1-amine (63 mg) was added to the reaction mixture at room temperature. The mixture was stirred for 18 hours at room temperature. Then, water and ethyl acetate were added to the mixture and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude residue was purified by chromatography on silica gel using a cyclohexane / ethyl acetate gradient to give 25 mg of the title compound as a clear oil. LC / MS (Method A) retention time = 1.11 minutes, 383 (M + H).

^X H NMR (400 MHz, CDCl3) δ ppm: 8.10 (d, 2H), 7.55 (d, 2H), 4.63 (s, 2H), 4.16 (d, 2H), 3, 81 (q, 2H), 3.08 (s, 3H), 2.28 (t, 1H), 1.17 (t, 3H).

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127/144 ¹⁹ F NMR (400 MHz, CDCl3) δ ppm: -65, 36 (s).

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

As an example, acid derivatives of formula (III) (0.0375 mmol in 375 pL of DMA) were transferred to a 96-slot deep well plate (DWP96) containing the derivatives [[5- (trifluoromethyl) -1, 2,4-oxadiazol-3yl] aryl] methanamine of formula (II) (0.03 mmol) and DIPEA (0.09 mmol) in 250 pL of DMA, followed by the addition of dissolved BOP-C1 (0.06 mmol) in DMA (250 pL). The DWP was sealed and stirred at 50 ° C for 18 hours. The solvent was removed under a stream of nitrogen. The resulting crude residues were solubilized in a mixture of MeOH (250 pL) and DMA (500 pL) and directly subjected to purification by preparative LC / MS which provided the compounds of formula (I) in yields of 10-85%.

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

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As an example, portions of triphosgene (5.94 mg) in DCE (0.3 mL) were transferred at 0 ° C to a 96-slot deep well plate (DWP96) containing amine derivatives [HN (R ⁴ ) R ⁵ ] of formula (IV) (0.05 mmol) and triethylamine (0.12 mmol) in 200 µl DMA. The reaction mixtures were stirred at room temperature for 30 minutes, then derivatives of [[5 (trifluoromethyl) -1,2,4-oxadiazol-3-i1] aryl] methanamine of formula (II) (0.05 mmol) were added and triethylamine (0.12 mmol) in 200 µl DMA. The DWP was sealed and stirred at rt for 18 hours. The DCE was removed under the Barkey station. The crude residues were solubilized in a mixture of MeOH (200 pL) and DMA (600 pL) and directly subjected to purification by preparative LC / MS that provided the compounds of formula (I) in yields of 10-85%.

Where necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate, using standard physical separation techniques such as reverse chiral chromatography, or through stereoselective synthetic techniques, (eg using starting chiral). Table Ti: Melting point data (mp) and / or retention times (Tr) for compounds according to Formula (I):

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Ent da

Compound name

Pasta

Meto

Structure (min) charge [M + H] of mp (° C) oxadiazol-3-yl] phenyl] met [il] urea [N- [cyclopropyl- j N - [[4- [5- I (trifluoromethyl ) -l, 2,4- I oxadiazol-3-ΐ yl] phenyl] methyl] oxazinane ΐ -2- I carboxamide ΐ 1- I (cyanomethyl) j -l-methyl-3- j (oxetan-3- [il) -3 - [[4- I [5- I (trifluorome j til) -l, 2,4oxadiazol-3-j] phenyl] met [il] urea [

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Ent Name T _r Pasta frog of Structure (min) charge gives compound [M + H]

Meto

1.6

1.8 mp (° C)

1 (cyanomethyl)

-3-ethoxy-lmethyl-3- [[4 - [5 (trifluorome

383

1.11 oxadiazol-3yl] phenyl] met 1-allyl-3ethoxy-1 [5oxadiazol-3yl] phenyl] met [[4- [5yl] isoxazoli methyl-3- [[4 (trifluorome

1.27

455

N-ethoxy-N (trifluorome oxadiazol-3yl] phenyl] met

1.20

399

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Ent Name Pasta T _r Method Federal Police frog of Structure charge (min) of (° C) gives compound [M + H] ................ dino-2- carboxamide

l-butoxy-31.9 (cyclopropyl methyl) -3propyl-1 [[4- [5 (trifluorome

F- ¹⁴ ^

F F

1.98

415 oxadiazol-3yl] phenyl] met

Ιοί clopropil1- (2,2 [[4- [5oxadiazole-3difluoroethyl) -3-ethoxy-3 (trifluorome

0.97

396 il] phenyl] met

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Goes into

Compound name 1-ethoxy-3,3diethyl-1 [[4- [5 (trifluorome oxadiazol-3yl] phenyl] met

1 (cyclopropyl methyl) -3ethoxy-1propyl-3 [[4- [5 (trifluorome oxadiazol-3yl] phenyl] met bis (2l- [[4- [5oxadiazole-3Pasta

Meto

Structure

l-ethoxy-3,3methoxyethyl) (trifluorome

1.75 (min)

1.71

1.91 charge [M + H]

384

385

387 mp (° C)

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Goes into

Compound name il] phenyl] met

1 (cyanomethyl)

-3cyclopropyl1-methyl-3 [[4- [5 (trifluorome oxadiazol-3yl] phenyl] met l-allyl-31-methyl-3 [[4- [5yl] phenyl] met

Pasta

Meto

Structure

cyclopropyl (trifluorome oxadiazol-3-

(min)

1.98

1.93 charge [M + H]

411

435 mp (° C)

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Ent

Name

Pasta T _r Method Structure charge (min) of [M + H]

mp (° C) of the compound ra

NcyclopropylN- [[4- [5 (trifluorome

387

1.1

D oxadiazol-32 yl] phenyl] methyl] isoxazole dino-2carboxamide

1-butoxy3,3-bis (2methoxyethyl) l - [[4- [5439

1.1 (trifluorome

D

1,3diciclopropi

1-1- (2,2difluoroethyl

1.1

447

1.83

D) -3 - [[4- [52 (trifluorome oxadiazole-3oxadiazole-3yl] phenyl] met

1.95

2.19

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Goes into

1.2

Compound name il] phenyl] met

Ιl - [[4- [5il] phenyl] met

Ιοί clopropil3 (cyclopropyl methyl) -3propyl-1 [[4- [5 (trifluorome oxadiazol-3yl] phenyl] met

Pasta

Meto

Structure οί clopropil3,3-diethyl (trifluorome oxadiazol-3-

ί

(min)

1.67

1.89 charge [M + H]

380

381 mp (° C)

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Ent

Name

Pasta

Meto pf do

Load structure (min) of compound (° C) [M + H]

Ιοί clopropil3,3-bis (2methoxyethyl) 1.2 l- [[4- [5 (trifluorome ethyl-1 - [[4 [51.2

D

407

D l-butoxy-3 (cyanomethyl)

-3-methyl-1 [[4- [51.2

431 (trifluorome

1.91

D oxadiazol-3yl] phenyl] met oxadiazol-3illfenillmet l-butoxy-3 (trifluorome oxadiazol-3illfenillmet

383

1.77

1.96

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Goes into

1.2

1.2

1.2

Name

Pasta

Meto pf do

Charge structure (min) of (° C) [M + H] compound l-allyl-3-butoxy-1methyl-3- [[4 - [5 (trifluorome

383

1.95

D oxadiazol-3yl] phenyl] met

N-butoxy-N [[4- [5 (trifluorome oxadiazol-3yl] phenyl] methyl] isoxazole dino-2carboxamide

1-butoxy3,3-dietill - [[4- [5 (trifluorome oxadiazol-3yl] phenyl] met

423

2.15

D

413

2, 13

D

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Goes into

Compound name

T _r Pasta Method Federal Police Structure (min) charge of (° C) .................................................. ............................. ........................ [M + H] .................. ................

l-butoxy-3cyclopropyl3- (2,2 - difluoroethyl

1.2) -! - [[4- [5 (trifluorome

1.96

387 tyl) -1,2,4oxadiazol-3yl] phenyl] met l-butoxy-31.2 l - [[4- [5til) -1,2,4yl] phenyl] met cyclopropyl (trifluorome oxadiazole-3-

1.93

412

BIOLOGICAL EXAMPLES:

General examples of tests on leaf discs in well plates:

Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. Leaf discs or segments are placed in multi-well plates (24-well format) on water agar. The leaf discs are sprayed with a solution

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140/144 test before (preventive) or after (curative) inoculation. The compounds to be tested are prepared as solutions in DMSO (maximum 10 mg / mL), which are diluted to the appropriate concentration with 0.025% Tween20 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 or check leaf segments is then calculated.

General examples of liquid culture tests on well plates:

Mycelia fragments or suspensions of a fungus conidia, freshly prepared from liquid cultures of the fungus or from cryogenic storage, are directly mixed in nutrient broth. DMSO solutions of the test compound (maximum 10 mg / mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 pL of that solution are pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spores / mycelium fragments is then added to generate a final concentration of the tested compound. 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 in relation to the untreated check is calculated.

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Example 1: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / preventive on leaf discs (brown rust)

Leaf segments of wheat cv. Kanzler were placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf discs were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19 ° C and 75% relative humidity (ur) 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 control disease, compared with no treatment, when an appropriate level of damage caused by the disease appears in untreated leaf foliar segments (7 to 9 days after application).

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.

Compounds (from Table T1) 1.1, 1.4, 1.6, 1.7, 1.8, 1.11, 1.14, 1.15, 1.16, 1.19, 1.21, 1.22, 1.23 and 1.28.

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

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

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142/144 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 a climate-controlled chamber, and the activity of a compound was evaluated as a percentage control of the disease, compared with no treatment, when an appropriate level of damage caused by the disease appears in untreated leaf control segments (6 to 8 days after application).

The compounds following 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.

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

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

Leaf soy discs are placed on water-agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the leaf discs are inoculated by spraying with a spore suspension on the lower leaf surface. After an incubation period in a 24-36 hour air-conditioned chamber in the dark at 20 ° C and 75% ur, the leaf disks are kept at 20 ° C with 12 h of light / day and ur at 75%. The activity of a compound is evaluated

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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.

Compounds (from Table T1) 1.1, 1.4, 1.6, 1.7, 1.11, 1.15, 1.16 and 1.19.

Example 4: Fungicidal activity against a liquid culture of G1 omerella lagenarium (Colletotrlchum lagenarium) / cucumber / preventive (Anthracnose)

The conidia of the cryogenic storage fungus are mixed directly in nutrient broth (PDB - potato dextrose broth). 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 growth inhibition is determined photometrically 3 to 4 days after application.

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

Compounds (from Table T1) 1.1, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15,

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1.16, 1.17, 1.18, 1.19, 1.21, 1.22, 1.23, 1.24, 1.25, 1.25

1.26, 1.27 and 1.28.

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Claims (13)

CLAIMS: 1. Compound of formula (I):

on what A is:

R ¹ and R ² are hydrogen; where (i) R ³ is R ^3a , where R ^3a is hydroxyl, ethoxy, propyl, cyclopropyl or 2,2,2-trifluoroethyl; and R ⁴ is R ^4a , where R ^4a is C2-5 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-3 cyanoalkyl, C2-4 alkoxy, C1-2 alkoxy C1-3 alkyl, C3-4 cycloalkyl or C3-4 cycloalkyl C1-2 alkyl; or (ii) R ³ is R ^3b , where R ^3b is isopropyl, butyl, isobutyl, sec-butyl, propyloxy, butyloxy, prop-2enyl, prop-2-inyl, prop-2-enyloxy, prop-2-inyloxy , methoxyethyl, cyclopropylmethyl or 3-oxetanyl; and R ⁴ is R ^4b , where R ^4b is C1-4 alkyl, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C2-4 alkyl; and R ⁵ is cyano, C1-5 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl, C3-4 haloalkenyl, C1-3 cyanoalkyl, Petition 870190098775, of 10/02/2019, p. 158/162 2/4 C1-3 hydroxyalkyl, C1-2 alkoxy C1-3 alkyl, C1-3 fluoroalkoxy C1-3 alkyl, C1-3 aminoalkyl, N-C1-3 alkylamino C1-3 alkyl or N, N-di-C1-3 alkylamino C1-3 alkyl; or R ⁵ represents C3-4 cycloalkyl or C3-4 cycloalkyl C1-2 alkyl, where the cycloalkyl moiety is optionally partially unsaturated, heterocyclyl or heterocyclyl C1-2, wherein the heterocyclyl moiety is a non-aromatic 4 to 6 ring members comprising 1, 2 or 3 heteroatoms individually selected from N, 0 and S, where for R ⁵ , any portion of cycloalkyl or heterocyclyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected at from R ⁶ ; R ⁶ represents cyano, halogen, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy; and wherein when R ⁵ comprises a substituted C3-4 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C (0)) or sulfonyl (S (0) 2) group; or where for R ³ as defined for each of (i) and (ii), R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, form a cycle selected from 3oxo-pyrrolidinyl, pyrrolidinyl, 2 -oxo-pyrrolidinyl, azetidinyl, iso-oxazolidinyl, oxazolidinyl, morpholino, oxazinanyl, 1-methoxypiperazin-4-yl, 1-methylpiperazin-4yl or l-piperazin-4-yl ethanone; or a salt or N-oxide thereof; with the proviso that the compound of Formula (I) is not: Petition 870190098775, of 10/02/2019, p. 159/162 3/4 N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] morpholino-4-carboxamide, N-isopropyl-N - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol3-yl] phenyl] methyl] isoxazolidine-2-carboxamide or Nisopropyl-N - [[4- [5- (trifluoromethyl ) -1,2,4-oxadiazol-3yl] phenyl] methyl] pyrrolidine-1-carboxamide. A compound according to claim 1, wherein R ^3a is ethoxy or cyclopropyl. A compound according to either of claims 1 or 2, wherein R ^4a is C2-5 alkyl, C3-4 alkenyl or C3-4 alkynyl. A compound according to claim 1, wherein R ^3b & n-butyloxy, cyclopropylmethyl or 3-oxetanyl. A compound according to either of claims 1 or 4, wherein R ^4b is C1-4 alkyl, C1-2 fluoroalkyl, C1-4 cyanoalkyl, C1-4 alkoxy or C1-4 alkoxy C24 alkyl · A compound according to any one of claims 1, 4 or 5, wherein R ^4b is methyl, ethyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, methoxy, ethoxy or C1-2 alkoxy 2-4 alkyl. A compound according to any one of claims 1, 2, 3, 4, 5 or 6, wherein R ⁵ is C1-3 alkyl, C1-3 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or cyanoalkyl C1-2, or R ⁵ is cyclopropyl or C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R ⁶ . A compound according to any one of claims 1, 2, 3, 4, 5, 6 or 7, wherein R ⁵ is C 1 alkyl Petition 870190098775, of 10/02/2019, p. 160/162 4/4 3, C1-2 fluoroalkyl, C3-4 alkenyl, C3-4 alkynyl or C1-2 cyanoalkyl, or R ⁵ is cyclopropyl or C1-2 cyclopropylalkyl, wherein any cyclopropyl is optionally substituted by 1 or 2 substituents, which can be the same or different, selected from R ⁶ , where R ⁶ is halogen, methyl or ethyl. A compound according to any one of claims 1, 2 or 4, wherein R ⁴ and R ⁵ , together with the nitrogen atom to which they are attached, form a cycle selected from morpholino or oxazinanyl. An agrochemical composition comprising a fungicidal effective amount of a compound of Formula (I), as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8 or 9. A composition according to claim 10, further comprising 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, in which a fungicidally effective amount of a compound of Formula (I), as defined in any of claims 1, 2, 3, 4, 5, 6, 7, 8 or 9, or a composition comprising that compound as an active ingredient, is applied to plants, their parts or their locus. 13. Use of a compound of Formula (I), as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8 or 9, as a fungicide.