BR112020000456A2 - microbiocidal oxadiazole derivatives - Google Patents

Abstract

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

Description

and D is R ', where

(i) R 'represents -C (O) N (R'º) (R'º), where:

R'º? is Cisalkyl, Ci-ahaloalkyl, cyanoCi-salkyl, hydroxyCi- 'alkyl, Ci-2alkoxyCi-.alkyl, Ci-2haloalkoxyC1: - salkyl, C3-salkenyl, C3-salquinyl, aminoCi-salkyl, amino, N, N-diCi- calkylamino, N-formyl-N-Ci-calkylamino, No. Ci-2alkylcarbonyl-N-Ci-2alkylamino, pyrrolidin-1-amino, piperidin-1-amino, morpholin-4-amino, N-Ci-2alkylaminoC1-salkyl, N , N-diCi-2alkylaminoCi-alkyl, hydroxyl, C1-alkoxy, C3-alkenyloxy, C3-uhaloalkyloxy, C3aalkynyloxy, cyclopropylCi-alkoxy; or

Ria is C3-scicloalkyl, C3-ecicloalkylCi -alkyl, phenyl, phenylCi-2zalkyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S (0) ', with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 2, 3 or 4 heteroatoms individually selected from N, O and S,

and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0), and

R '? is hydrogen, Ci-salquila, Ci-ahaloalkila, or cyclopropila, or

R'º and Rr, together with the nitrogen atom to which they are attached, form a 4- to 6-membered monocycle optionally containing a heteroatom or additional group selected from O, S, S (0) 2x, C (O) and NRº6, or

R'º and Rr, together with the nitrogen atom to which they are attached, form a spirobyclic ring system with up to 8 members optionally containing a heteroatom or additional group selected from O, C (O0), and NRº;

Rº is hydrogen, methyl, methoxy, formyl or acyl;

or

(ii) R 'represents -C (0) OR'º, where:

R'ºe is Corsalquila, Ci-ahaloalkila, cyanoCi-salquila, hydroxyCi- «alkyl, Ci-2aloxyCr-s« alkyl, Ci-2alcoxyC1; - 2alcoxyCi.alkyl, Ci-2haloalkoxyCi- «xalkyl, C3-salquila, C3-salquin , C3-2haloalkenyl, N-Ci-zalkylaminoCi-xalkyl, N, N-di-Ci-3alkylaminoCi-salkyl; or

R'º is C3-scicloalkyl, C3-scicloalkylCi-2alkyl, phenyl, phenylCi2alkyl, heterocyclyl or heterocyclyl; - 2alkyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2, or 3 members of ring independently selected from the group consisting of O, S, N or S (0) ', with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-calkyl, where the heteroaryl fraction is a aromatic ring with 5 or 6 members comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S,

and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0);

or

(iii) R 'represents -C (0) C (O) N (R'9) (R'º), where

R '* º is Cisalkyl, Ci-chaloalkyl, cyanoCi-salkyl, hydroxyCi-' alkyl, Ci-3alkoxyCrz4salkyl, Ci-2haloalkoxyC1- aalkyl, C3-salkenyl, C3a-salquinyl, hydroxyl, aminoC1-salquyl, N-salty, N-salty, N, N-diCi -alkylamino, pyrrolidin-1-amino, piperidin-1-amino, morpholin-4-amino, C1- saloxy, C3-; haloalkyloxy, C3a-xalkenyloxy, C3a- «alkynyloxy, cyclopropylCi-raloxy, (Ci -salkyl) -ON = C (H) Cixalkyl-, or

Rá is C3-scicloalkyl, C3-scicloalkylCi-2alkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2, or 3 ring members independently selected from the group consisting of O, S, N, SO2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, where the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N , O and S,

wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different,

selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl fraction is optionally substituted with 1 or 2 groups that are oxo (= 0); and R'º is hydrogen, Ci-salquila, Ciafluoroalkyl, cyclopropyl, cyclopropylmethyl; or (iv) R 'represents -C (0) C (0) OR'í, where: R'f is hydrogen, Ci-salquila, Ci-ahaloalkila, C3-salquenila, C3-salquinila, or R'f is C3-scicloalkyl, C3-ecicloalkylCi-alkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or 2 ring members independently selected from the group consisting of O, S, N, SO7z , with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S ; or (v) R 'represents -C (0) C (O0) R'9, where: R'9 is hydrogen, Ci-salquila, or cyclopropyl; or (vi) Rº represents (Ci-alkyl) -ON = C (H) -, (C1- ahaloalkyl) -ON = C (H) -, (C3-chenyl salt) -ON = C (H) -, ( C3-salquinyl) -ON = C (H) - or benzyl-ON = C (H) -; a salt or an N-oxide of it.

[0003] Surprisingly it was discovered that the new compounds of Formula (1) have, for practical purposes,

a very advantageous level of biological activity to protect plants against diseases that are caused by fungi.

[0004] According to a second aspect of the invention there is provided an agrochemical composition comprising a fungicidal effective amount of a compound of Formula (1). Such an agricultural composition may additionally comprise at least one additional active ingredient and / or an agrochemical acceptable diluent or carrier.

[0005] According to a third aspect of the invention there is provided a method to control or prevent infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidal effective amount of a compound of Formula (IL), or a composition comprising this compound as an active ingredient, it is applied to plants, their parts or their locus.

[0006] According to a fourth aspect of the invention, the use of a compound of Formula (1) as a fungicide is provided. In accordance with this particular aspect of the invention, use may exclude methods for treating the human or animal body by surgery or therapy.

[0007] As used herein, the term "halogen" or "halo" refers to fluorine (fluorine), chlorine (chlorine), bromine (bromine) or iodine (iodine), preferably fluorine, chlorine or bromine.

[0008] As used here, cyan means a -CN group.

[0009] As used herein, the term "hydroxyl" or "hydroxy" means an -OH group.

[0010] As used here, amino means a group -NH>.

[0011] As used here, acyl means a group - C (0) CH: 3.

[0012] As used here, formyl means a group - C (O0) H.

[0013] As used here, the term “Ci-salquila” refers to a straight or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing no unsaturation, having from one to five carbon atoms and which is linked to the rest of the molecule by a single bond. Cisalkyl, Ci-zalkyl and Cicalkyl must be considered accordingly. Examples of Ci-salkyl include, but are not limited to, methyl, ethyl, n-propyl, 11-methylethyl (isopropyl), n-butyl and 11-dimethylethyl (E-butyl). A "Ci-Cralkyl" group refers to the corresponding definition of Ci-Cralkyl, with the exception that such a radical is linked to the rest of the molecule by two simple bonds. Examples of C1-2 alkylene are -CH; - and -CHxCHyi-.

[0014] As used here, the term "Cisaloxy" refers to a radical of the formula -OR. where Ra is a Ci.alkyl radical as generically defined above. The terms C1- zaloxy and C1-2alkoxy must be interpreted accordingly. Examples of Cisaloxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and t-butoxy.

[0015] As used here, the term "Ci4shaloalkyl" refers to a Cisalkyl radical as generically defined above substituted with one or more equal or different halogen atoms. Examples of Ci «haloalkyl include, but are not limited to, fluoromethyl, fluoroethyl,

difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.

[0016] As used here, the term "C3-s 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 the (E) configuration or (4), having three to five carbon atoms, which is attached to the rest of the molecule by a single bond. Examples of C3-salkenyl include, but are not limited to, prop-1-enyl, ally (prop-2 -enyl) and but-11-enyl.

[0017] As used here, the term "C3z-uhaloalkenyl" refers to a C3 radical "alkenyl as generically defined above substituted with one or more equal or different halogen atoms.

[0018] As used here, the term "C3zasalquenóxi" refers to a radical of the formula -OR. in which Ra. is a C3z-1 alkenyl radical as generally defined above.

[0019] As used here, the term "C3salquinyl" refers to a radical group of straight or branched hydrocarbon chain consisting only of carbon and hydrogen atoms, containing at least one triple bond, having three to five carbon atoms, and which is linked to the rest of the molecule by a single bond. Examples of C3-salquinyl include, but are not limited to, prop-1-inyl, propargyl (prop-2-inyl).

[0020] As used here, the term "C3z4alkynoxy" refers to a radical of the formula -OR. where R. is a C3z-1alkynyl radical as generically defined above.

[0021] As used herein, the term "C3asalquinyloxyC1: - salkyl" refers to a Cisalkyl radical as generically defined above substituted with a C3-salquinyloxy group as defined above.

[0022] As used here, the term "Cic2alkoxyCisalkyl" refers to a radical of the formula Rv-O-Ra- where R, is a Ci-calkyl radical as generically defined above, and Ra is a Cisalkylene radical as generically defined above .

[0023] As used herein, the term "hydroxyCisalkyl" refers to a Cisalkyl radical as generically defined above substituted with one or more hydroxy groups. The term "hydroxyCi-ralkyl" should be considered accordingly.

[0024] As used herein, the term "cyanoCi-csalkyl" refers to a Cisalkyl radical as generically defined above substituted with one or more cyan groups.

[0025] As used herein, the term "Ci-salkylcarbonyl" refers to a radical of the formula -C (O) R. where Ra is a Cisalkyl radical as generically defined above.

[0026] As used herein, the term "Ci-calcoxyCi-calcoxyCi-salkyl" refers to a radical of the formula R.ºOR »pOR: c-, where Rv and Rc are Ci-calkylene radicals as generically defined above, and Frog. is a Cisalkyl radical as generically defined above.

[0027] As used herein, the term "N-Ci-salkylamino" refers to a radical of the formula RaNH- in which Ra. is a Ci-salquila radical as generically defined above.

[0028] As used here, the term "N, N-diCi-« xalkylamino "refers to a radical of the formula R = (Ra) N- where Ra. is a Cisalkyl radical as generically defined above.

[0029] As used herein, the term "C3aahaloalkoxy" refers to a C3- «alkoxy group as defined above substituted with one or more equal or different halogen atoms.

[0030] As used here, the term "C3a-ecicloalkyl" refers to a stable monocyclic ring radical that is saturated or partially unsaturated and contains 3 to 6 carbon atoms. C3-sCicloalkyl and Ciacicloalkyl must be interpreted accordingly. Examples of C3a-cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl and cyclohexen-3-yl.

[0031] As used herein, the term "Ca-ecicloalkylCo: - 2alkyl" refers to a C3- «ecicloalkyl ring as defined above attached to the remainder of the molecule by a C1-2alkylene radical as defined above. Examples of C3-scicloalkylC: - zalkyl include, but are not limited to, cyclopropyl-methyl and cyclobutyl-ethyl.

[0032] As used here, the term "phenylCi-zalkyl" refers to a phenyl ring attached to the remainder of the molecule by a Cicalkylene radical as defined above. Examples of phenylCi-2alkyl include, but are not limited to, benzyl.

[0033] As used herein, the term "heteroaryl" generally refers to a 5- or 6-membered monocyclic aromatic ring radical comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur. The heteroaryl radical can be linked to the rest of the molecule through a carbon atom or heteroatom. Examples of heteroaryl include, but are not limited to, furila, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl,

oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, pyridyl and indolyl.

[0034] As used herein, the term "heterocyclyl" or "heterocyclic" refers to a non-aromatic monocyclic ring with 4 to 6 members saturated or partially saturated stable, comprising 1, 2 or 3 hetero atoms individually selected from nitrogen, oxygen and sulfur. The heterocyclyl radical can be linked to the rest of the molecule via a carbon atom or hetero atom. Examples of heterocyclyl include, but are not limited to, azetidinyl, oxetanyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl and morpholinyl.

[0035] The presence of one or more possible asymmetric carbon atoms in a compound of Formula (1) means that the compounds can occur in chiral isomeric forms, that is, enantiomeric or diastereomeric forms. Atropisomers can also occur as a result of restricted rotation around a single bond. Formula (1) is intended to include all of these possible isomeric forms and their mixtures. The present invention includes all of these possible isomeric forms and mixtures thereof for a compound of Formula (I). Likewise, Formula (1) 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 (1).

[0036] In each case, the compounds of Formula (1) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form or in salt form, for example, a salt form agronomically usable or agrochemically acceptable.

[0037] N-oxides are oxidized forms of tertiary amines or oxidized forms of heteroaromatic compounds that contain nitrogen. They are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0038] The following list provides definitions, including preferential definitions, for the substituents R !, Rºà, Rô3, Ri, R5, R6, Z (including 2nd, 2nd, 23), Rº (including R as defined by R 'º, R' »”, Rise, Rd, R'º, R'f, R'9) and Rº with reference to the compounds of Formula (I) according to the invention. For any of these substituents, any of the definitions given below can be combined with any definition of any other substituent shown below or elsewhere in this document.

[0039] R !, R2º, Rà, Rº are independently selected from hydrogen or fluorine, where O, 1 or 2 of R !, R2à, Rº and Ré are fluorine.

[0040] In certain embodiments of the invention, R !, R2ày, Rê and Rº are hydrogen; Rº, R? º and Rº are hydrogen and R 'is fluorine; R! ', RR and Rº are hydrogen and Rº is fluorine; R 'and Rº are fluorine and R? and Rº are hydrogen; R! and R? are fluorine and R? and Rº are hydrogen, or R! ' and R? are hydrogen and R? º and Rº "are fluorine. Preferably, R 'to Rº are hydrogen, or R! is fluorine and R? up to Rº are hydrogen.

[0054] In some embodiments of the invention, R 'is represented by the group (vi).

[0055] (i) R 'can represent -C (O) N (R'º) (R' ”"), where: R'º? Is Cisalquila, Ci-ahaloalkila, cyanoCi-salquila, hydroxyCi- «alkyl , Ci-2alcoxyCi-salquila, Ci-2haloalkoxyC1: - salquila, C3-salquenila, C3-salquinila, aminoCi-salquila, amino, N, N-diCi-calquilamino, N-formil-N-Ci-calquilamino, Nº Ci-2alkylcarbonyl -N-Ci-calkylamino, pyrrolidin-1-amino, piperidin-1-amino, morpholin-4-amino, N-Ci-2alkylaminoC1-salkyl, N, N-diCi-2alkylaminoCi-calkyl, hydroxyl, C1-saloxy, C3asalkenyloxy , C3a-ahaloalkyloxy, C3aalkynyloxy, cyclopropylCi-alkoxy; or Ria is C3-scicloalkyl, C3-ecicloalkylCi-alkyl, phenyl, phenylCizalkyl, heterocyclyl, in which the heterocyclic fraction is a non-aromatic 4-membered ring with 4 up to 6 members , or 3 ring members independently selected from the group consisting of O, S, N or S (0) ', with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl in which the heteroaryl fraction is a aromatic ring with 5 or 6 members comprising 2, 3 or 4 heteroatoms individually selected from N, O and S, and where the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl , amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0), and RP is hydrogen , Ci-salquila, Ci-ahaloalkila or cyclopropila, or R'º and Rr, together with the nitrogen atom to which they are attached, form a 4- to 6-membered monocycle optionally containing a heteroatom or additional group selected from O, S , S (0) 2, C (O0) and NRº, or R'º and Rr, together with the nitrogen atom to which they are attached, form a spirobyclic ring system with up to 8 members optionally containing an additional heteroatom or group selected from O, C (O0), and NRº, where Rº is hydrogen, methyl, methoxy, formyl or acyl.

[0056] Preferably, Ria is Cisalkyl, Ci- 2fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, C1i- 2alkoxyCi-2ralkyl, Ci-rfluoroalkoxyCi-ralkyl, C3-aalkenyl, C3-salquinyl, aminoCi-amino -diCi-calkylamino, N-formyl-N-Ci-2alkylamino, N-C1-2alkylcarbonyl-N-C1- 2alkylamino, pyrrolidin-1-amino, piperidin-1-amino, morfolin-4-amino, N-Ci-2alkylaminoCi -2alkyl, N, N-diC1-1-2alkylaminoCi-alkyl, hydroxyl, C1-2alkoxy, C3- salkenyloxy, C3a-ahaloalkyloxy, Ca-calquinyloxy, cyclopropylCi-2alkoxy. More preferably, R '"? º is Cr salkyl, Ci-2fluoroalkyl, cyanoCi-2alkyl, hydroxyC1: - 2alkyl, Ci-2alcoxyCi-2ralkyl, Ci-2fluoroalkoxyCi-2alkyl, C3-salkenyl, C3-salquinyl, aminoCi-2 , hydroxyl, Ci-alkoxy, C3-alkenyloxy, C3- <haloalkyloxy, C3-salquinyloxy.

[0057] Preferably, R'º is C3-ecicloalkyl, C3-scicloalkylCi-alkyl, phenyl, phenylCi-alkyl, heterocyclyl, wherein the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or 2 ring members independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 2 or 3 heteroatoms individually selected from N, O and S, and in which the cycloalkyl, phenyl, heterocyclyl, or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 group which is oxo (= O).

[0058] Preferably, R '"” P is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. More preferably, R'? ” is hydrogen or methyl.

[0059] (ii) Rº can represent -C (0) OR'º, where: R'ºe is Corsalquila, Ciahaloalkila, cyanoCisalquila, hydroxyCi- «alkyl, Ci-2alcoxiCr-calquila, Ci-2alcoxiC1: - 2alcoxiCic.alquila , Ci-2haloalkoxyCi-salkyl, C3-salkenyl, C3-salquinyl, C3-uhaloalkenyl, N-Ci-zalkylaminoCi-czalkyl, N, N-di-Ci-3zalkylaminoCi-salquila; or R'º is C3-ecicloalkyl, C3-ecicloalkylC; i -alkyl, phenyl, phenylCi> zalkyl, heterocyclyl or heterocyclyl: - 2alkyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2 , or 3 ring members independently selected from the group consisting of O, S, N or S (0) ', with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-zalkyl, where the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl fraction is optionally substituted with 1 or 2 groups that are oxo (= O).

[0060] Preferably, Re is Cr-salkyl, C1- afluoroalkyl, cyanoCi -alkyl, hydroxyCi -alkyl, C1-2alkoxyCralkyl, Ci-2alkoxyCi-2alcoxyCi-calkyl, C1- 2haloalkoxyCi-2alkyl, C3-salkyl, C3-salkyl - ahaloalkenyl, N-C1-2alkylaminoCi-zalkyl, N, N-di-C1-1-2alkylaminoCi-calkyl.

[0061] Preferably, R'º is C3-ecicloalkyl, C3-ecicloalkylCi-alkyl, phenyl, phenylCi-2alkyl, heterocyclyl or heterocyclylCiszalkyl, wherein the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or 2 members of ring independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-alkyl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl , formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl fraction is optionally substituted with 1 group which is oxo (= O).

[0062] (iii) R 'can represent -C (0) C (O) N (R'9) (R'º), where R'º is Cisalquila, Ci-ahaloalkila, cyanoCi-salquila, hydroxyCi- « alkyl, C1-3alkoxyCr-, C1-2haloalkoxyC1 alkyl: - salkyl, C3-salkenyl, C3-salquinyl, hydroxyl, aminoC1-salkyl, N-CisalkylaminoCi-salkyl, N, N-diCicalkylamino, pyrrolidinid-l-amino, pyrrolidinid-l-amino, 1-amino, morpholin-4-amino, C1-saloxy, C3-ahaloalkyloxy, C34alkenyloxy, C3aalkynyloxy, cyclopropylCi-2alkoxy, (Cisalkyl) -ON = C (H) Cisalkyl-, or RI is C3-cycloalkyl; i-2alkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2, or 3 ring members independently selected from the group consisting of O, S, N, SO7z, with the provided that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S,

wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0); and R7º is hydrogen, Cisalkyl, Ciafluoroalkyl, cyclopropyl, cyclopropylmethyl.

[0063] Preferably, Rd is Ci-salquila, C1a- 2fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, C1- 2alkoxyCzalkyl, Ci-dhaloalcoxyCi-alkalkyl, C3a-calkenyl, C3-salquinyl, hydroxyl, amino-hydroxy, amino -2alkylaminoC; 1- 2alkyl, N, N-diCi-2alkylamino, pyrrolidin-1-amino, piperidin-1-amino, morpholin-4-amino, Cisaloxy, C3-ahaloalkyloxy, C3-aalkenyloxy, C3-aalkynyloxy, cyclopropyl , (Cisalkyl) -ON = C (H) Cisalkyl-. More preferably, R'º is Crisalquila, Ci-2fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-alkyl, CizalcoxyCralquila, C1- 2haloalcoxyCi-2alkyl, C3-calkenen, Caaalquinyl, hydroxyl, aminoCi-alkyl-alkali-N-cycloalkyl, N-alkali , Ca-uhaloalkyloxy, C3a'alkenyloxy, C3aalkynyloxy.

[0064] Preferably, R'º is C3-ecicloalkyl, C3-ecicloalkylC; i-cralkyl, phenyl, heterocyclyl, wherein the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or 2 independently selected ring members from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S, in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 group which is oxo (= O).

[0065] Preferably, R '"º is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. More preferably, R'º is hydrogen or methyl.

[0066] (iv) R 'can represent -C (0) C (0) OR' ”, where: R'f is hydrogen, Ci-salquila, Ci-ahaloalkila, C3-salquenila, C3-salquinila, or Rf is C3-scicloalkyl, C3-scicloalkylCi-2alkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or 2 ring members independently selected from the group consisting of O, S, N, SO2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S.

[0067] Preferably, R'f is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl, C3-walkenyl or C3-salquinyl.

[0068] Preferably, R '"is C3-ecicloalkyl, C3-secycloalkylCi-alkyl, phenyl, heterocyclyl, wherein the heterocyclyl fraction is a non-aromatic ring with 5 to 6 members comprising 1 or 2 ring members independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S.

[0069] (v) R 'can represent -C (O) C (O) R'% 9, where R'º is hydrogen, Ci-salquila, or cyclopropila.

[0070] Preferably, R'º is hydrogen, methyl, ethyl, n-propyl, or cyclopropyl.

[0071] (vi) Rº can represent (Ci-xalkyl) -ON = C (H) -, (Ci-ahaloalkyl) -ON = C (H) -, (C3-chenyl salt) -ON = C (H) , (C3-salquinyl) -ON = C (H) - or benzyl-ON = C (H) -, preferably (C1-2alkyl) -ON = C (H) -, (C1-2 fluoroalkyl) -ON = C ( H) -, (C3-salkenyl) -ON = C (H) -, (C3salquinyl) -ON = C (H) - or benzyl-O- N = C (H) -, and more preferably (C1-2alkyl) -ON = C (H) - or (Ci-afluoroalkyl) -ON = C (H) -.

[0072] Preferably, the compound according to Formula (I) is selected from a compound 1.1 to 1.10 described in Table T1 (below), or a compound 2.1 to 2.80 described in Table T2 (below).

[0073] The compounds of the present invention can be enantiomers of the compound of Formula (1) as represented by a Formula (Ia) or a Formula (Ib), where Rº and Rº are different substituents.

Rê ”- 1 2 Ç

R N F

Z nº D Ls 2 0) no ||:

RN F CN F | IS 1 | rs 1 R>

R N OHF N OHF H + H z a z

R Ss L6

RE RP R R (Fla) (Hla) | | tautomerization | | 3 o F

KR HINO F RO HNA F R SN on E N OHF + z Z. né RÊ RR pP RR RR (1-lb) (Hb)

[0075] The compounds of the present invention can be prepared as shown in the following schemes 1 through 12, in which, unless stated otherwise, the definition of each variable is as defined above for a compound of formula (1).

[0076] The compounds of formula (1) can be prepared from compounds of formula (II), where X is a halogen, preferably Cl, Br or I, by treatment with

[0086] The compounds of the formula (IA), in which Z represents Z !, 2º or Z3 and Rº-Nu-H represents HOR'º, HOR '”, HN (R'29) R' * P or HN (R 'º) R' "ºe, can be obtained by an amide coupling transformation with compounds of the formula (IB) and nucleophiles of the formula (XIII), by activating the carboxylic acid function of the compounds of the formula (IB), a process that it usually occurs by converting the -OH of the carboxylic acid into a good labile group, such as a chloride group, for example, using (COCl)> or SOCl ;, before treatment with the nucleophiles of the formula (XIII), preferably in a solvent suitable (for example, dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 ° C and 100 ° C, and optionally in the presence of a base such as triethylamine or N, N-diisopropylethylamine, or under conditions described in the literature for an ester or amide coupling.

For examples, see WO 2003/028729. Compounds of the formula (XIII) 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 11.

for the man. The new compounds are distinguished by their excellent activity at low application rates, by being well tolerated by plants and by being environmentally safe. They have very useful healing, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of Formula (1) can be used to inhibit or destroy pests that occur in plants or parts of plants (fruit, blooms, leaves, stems, tubers, roots) from different crops of useful plants, while protecting, for example, of phytopathogenic microorganisms, also those parts of plants that grow later.

[0090] The present invention further relates to a method to control or prevent infestation of plants or plant propagating material and / or harvested food crops susceptible to microbial attack by treating plants or plant propagating material and / or food crops harvested, in which an effective amount of a compound of Formula (1) is applied to plants, their parts or their locus.

[0091] It is also possible to use compounds of Formula (1) as a fungicide. The term "fungicide", as used here, 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 able to produce 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.

[0092] It may also be possible to use compounds of Formula (1) as covering agents for the treatment of plant propagating material, for example, seed, such as fruits, tubers or grains, or plant cuttings, for protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of Formula (I) before planting: seed, for example, can be covered before being sown. The active compounds of Formula (I) can also be applied to grains (coating), by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied at the planting site when the propagation material is being planted, for example, in the seed groove during sowing. The invention also relates to such methods of treating plant propagating material and to the plant propagating material so treated.

[0093] Furthermore, the compounds of Formula (1) 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 the storage of food, in the management of hygiene.

[0094] Additionally, the invention can be used to protect non-living materials from fungal attack, for example, construction wood, wall panels and paint.

[0095] 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:

[0096] Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including (CC. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechspor 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, Leptographic, Leptographic, Leptograph spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp.

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

Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora .nodorum, Stemphylium spp ,. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp.

including V. inaequalis, Verticillium spp, and Xanthomonas spp.

[0097] The compounds of Formula (I) can be used, for example, in grass, ornamental plants such as shrub flowers, leafy or evergreen trees, for example, conifers, as well as for injection into trees, pest management and similar.

[0098] 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 plants, for example, blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example, barley, maize (maize), millet, oats, rice, rye, sorghum, triticale and wheat; fibrous 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, levistic, mint, oregano, parsley, rosemary, sage and thyme; legumes, for example, beans, lentils, peas and soy; nuts, for example, almond, cashew, peanut seed, hazelnut, peanut, pecan, pistachio and walnut; palm trees, for example, oil palm; ornamental plants, for example, flowers, shrubs and trees; other trees, for example,

cocoa, coconut, olive and rubber; vegetables, for example, asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato, and vines, for example, grapes .

[0099] The term "useful plants" should be understood as also including useful plants that have been made tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfifuron, prosulfuron and trifloxysulfuron, EPSPS inhibitors (5-enol-pyrovil-chiquimate-3-phosphate synthase), GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, for example, imazamox, by conventional breeding methods (mutagenesis) is the summer rape clearfieldo (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 RoundupReadyo, Herculex IO and LibertyLinkoO.

[0100] The term "useful plants" should be understood as also including useful plants that have been thereby transformed by the use of recombinant DNA techniques that are capable of synthesizing one or more selectively active toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[0101] Examples of such plants are: YieldGardO (more variety that expresses a CryIA toxin (b)); YieldGard Rootworm8 (more variety that expresses a CryIIIB toxin (bl)); YieldGard Plus8 (more variety that expresses a CryIA toxin (b) and a CryIIIB toxin (bl)); Starlink & (variety of more that expresses a Cry9 toxin (c)); Herculex IO (variety of maize expressing a CryIF toxin (a2) and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B8 (cotton variety that expresses a CryIA toxin (c)); Bollgard IO (cotton variety that expresses a CryIA toxin (c)); Bollgard IIO (cotton variety that expresses a CryIA toxin (c) and a CryIIA toxin (b)); VIPCOTO (cotton variety that expresses a VIP toxin); NewLeaf & 8 (potato variety that expresses a CryIIIA toxin); NatureGardO Agrisureêo GT Advantage (glyphosate tolerance trait GA21), Agrisureo CB Advantage (trait of corn borer (CB) Btl1), Agrisure6 RW (trait of corn rootworm) and Protecta € Q.

[0102] The term "cultures" should be understood to also include culture plants that have been transformed by the use of recombinant DNA techniques so that they are able to synthesize one or more selectively acting toxins, as they are known, for example, of bacteria that produce toxins, especially those of the genus Bacillus.

[0103] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins of Bacillus cereus or Bacillus popilliae, or insecticidal proteins of Bacillus thuringiensis, such as ô & - endotoxins, for example, CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vipl, Vip2, Vip3 or Vip3A, or insecticidal proteins of nematode colonizing bacteria, for example, Photorhabdus spp. or Xenorhabdus sSPpPp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect specific neurotoxins; toxins produced by fungi, such as toxins from Streptomycetes, plant lectins, such as pea lectins, barley lectins or white bell lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, more RIP, abrina, lufina, saporina or briodina; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA reductase, ion channel blockers, such as sodium or calcium channel blockers, hormone juvenile esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0104] Additionally, in the context of the present invention, ô-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, also expressly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of these proteins (see, for example, WO 02/15701). Truncated toxins, for example, a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid substitutions, preferably non-naturally occurring protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03/018810 ).

[0105] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-AO 374 753, WO93 / 07278, WO95 / 34656, EP-AO 427 529, EP-A-451 878 and WO 05/032073.

[0106] The processes for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI type and their preparation are known, for example, from WO 95/34656, EP-A-O 367 474, EP-A-O 401 979 and WO 90/13651.

[0107] 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 and commonly found in beetles (Coleoptera), double-winged insects (Diptera) and butterflies (Lepidoptera).

[0108] Transgenic plants that contain one or more genes that encode an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGardo (variety of maize that expresses a CrylAb toxin); YieldGard Rootworm8O (variety of more that expresses a Cry3Bbl toxin); YieldGard Plus8 (more variety that expresses a CrylAb toxin and a Cry3Bbl); StarlinkO (variety of maize that expresses a Cry9C toxin); Herculex IO (variety of maize that expresses a CrylFa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NUCOTN 33B8 (cotton variety that expresses a CrylAc toxin); Bollgard IO (cotton variety that expresses a CrylAc toxin); Bollgard IIG (cotton variety that expresses a CrylAc toxin and a Cry2Ab); VipCotO (cotton variety that expresses a Vip3A toxin and a CrylAb); NewLeaf & o (potato variety that expresses a Cry3A toxin); NatureGardO, Agrisureo GT Advantage (glyphosate tolerant trait GA21), Agrisure6 CB Advantage (trait of corn borer (CB) Btll) and Protecta € O.

[0109] Additional examples of such transgenic crops are:

1. Bt11 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 st. Sauveur, France, registration number

C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Btl11 corn also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

2. Bt176 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Btl76 corn also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

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

4. MON 863 maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02/9. MON 4863 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. Corn 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00/10. Corn genetically modified for the expression of the CrylF protein to achieve resistance to certain Lepidoptera insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

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

[0110] The compounds of Formula (1) (including any of compounds 1.1 to 1.10 described in Table T1 (below) or compounds 2.1 to 2.80 described in Table T2 (below) according to the present invention can be used in the control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

[0111] In particular, transgenic soybean plants express toxins, for example, insecticidal proteins such as delta-endotoxins, for example, CrylAc (protein CrylAc Bt). Accordingly, they may include transgenic soybean plants comprising the MON87701 event (see U.S. Patent No.

8,049,071 and related applications and patents, as well as WO 2014/170327 Al (for example, see paragraph [008], reference to Intacta RR2 PRO soy "" "), event MON87751 (US Patent Application Publication No. 2014/0373191 ) or DAS-81419 event (US Patent No. 8632978 and related applications and patents).

[0112] Other transgenic soybean plants may comprise the SYHTOH2 event - tolerance to HPPD (US Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (US Pat. No. 7,632,985 and orders and related patents), event MON87708 - dicamba tolerance (US Patent Application Publication No. US 2011/0067134 and related orders and patents), event DP-356043-5 - glyphosate tolerance and ALS (Patent Application Publication US No. 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (US Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP-305423-1 - tolerance ALS (US Patent Application Publication No. US 2008/0312082 and related applications and patents), event ASS47-127 - glufosinate tolerance (US Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS-40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011/022469, WO 2011/022470, WO 2011/022471 and related applications and patents), event 127 - ALS tolerance (WO 2010/080829 and related applications and patents) , event GTS 40-3-2 - tolerance to glyphosate, event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate,

event FG72 - tolerance to glyphosate and isoxaflutole, event BPS-CV127-9 - tolerance to ALS and GU262 - tolerance to glufosinate or event SYHTO4R - tolerance to HPPD.

[0113] Under certain circumstances, the compounds of Formula (1) according to the present invention, when used in the control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants (in particular any of the transgenic soybean plants as described above), may exhibit a synergistic interaction between the active ingredients.

[0114] Additionally, to date, no cross-resistance has been observed between the compounds of Formula (1) (including any of the compounds 1.1 through 1.10 described in Table T1 (below) or compounds 2.1 through 2.80 described in Table T2 (below )) and current fungicide solutions used to control Phakopsora pachyrhizi.

[0115] Indeed, fungicide-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following classes of fungicidal modes of action being observed: sterol demethylation inhibitors ( DMI), external quinone inhibitors (QolI) and succinate dehydrogenase (SDHI) inhibitors. See for example: "Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms." Schmitz HK et al., Pest Manag Sci (2014) 70: 378-388; "First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi" Simões K et al, J Plant Dis Prot (2018) 125: 21-

2; "Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes". Klosowski AC et al., Phytopathology (2016) 106: 1278-1284; "Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi". Klosowski AC et al., Pest Manag Sci (2016) 72: 1211-1215.

[0116] Thus, in a preferred embodiment, the compounds of Formula (1) (including any of the compounds

1.1 through 1.10 described in Table T1 (below) or compounds

2.1 to 2.80 described in Table T2 (below)), or fungicidal compositions according to the present invention comprising a compound of Formula (I), are used to control Phakopsora pachyrhizi that are resistant to one or more fungicides of any of the following MoA classes fungicides: sterol demethylation inhibitors (DMI), external quinone inhibitors (QolI) and succinate dehydrogenase inhibitors (SDHI).

[0117] The compounds of Formula (1) (including any of compounds 1.1 to 1.10 described in Table T1 (below) or compounds 2.1 to 2.80 described in Table T2 (below) or fungicidal compositions according to the present invention comprising a compound of Formula (I) can be used to control or prevent phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants. In particular, certain varieties of Elite soybean plants are known in the scientific literature where stacks of the R gene, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, were introgressed into the plant's genome, see,

for example: “Fighting Asian Soybean Rust”, Langenbach C, et al., Front Plant Science 7 (797) 2016).

[0118] An elite plant is any plant in an elite line, so an elite plant is a plant representative of an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to soybean farmers or breeders include: AGOO802, AO868, AGO902, Al923, AG2403, A2824, A3704, A4324, AS404, AG5903, AG6202 AGO934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231l (Asgrow Seeds, Des Moines, Iowa, USA); BPRO144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, Ill., USA); DKBl7- 51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex., USA); JG O0O3R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90MO01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, POO8T22R2; PI6T17R2; P22T69R; P25T51R; P34TO7R2; P35T58R; P39T67R; P47T36R; P46T21R; and PS6TO03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Ind., USA); SOO-K5, S11-L2, S28-Y2, S43-Bl, S53-Al, S76-L9, S78-G6, SOO009-M2; SOO07-Y4; SO4-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and S78-GG6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. Ia., USA); or Armor 4744 (Armor Seed, LLC, Ar., USA).

[0119] Thus, in an additional preferred embodiment, the compounds of Formula (I) (including any of compounds 1.1 through 1.10 described in Table T1 (below) or compounds 2.1 through 2.80 described in Table T2 (below)), or compositions Fungicides according to the present invention comprising a compound of Formula (1), are used to control Phakopsora pachyrhizi (including its fungicide resistant strains, as outlined above) in varieties of Elite soy plants in which R gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, were introgressed in the plant genome. Numerous benefits can be expected to result from such use, for example, improved biological activity, an advantageous or broader spectrum of activity (including sensitive and resistant strains of Phakopsora pachyrhizi), an increased safety profile, improved crop tolerance, synergistic interactions or enhancing properties, improved onset of action or residual activity of longer duration, a reduction in the number of applications and / or a reduction in the application rate of compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thus allowing beneficial resistance management practices, reduced environmental impact and reduced operator exposure.

[0120] The term “locus” as used here means fields in which or on which plants are growing or where seeds of cultivated plants are sown or where seed will be placed in the soil. It includes soil, seeds and seedlings, as well as established vegetation.

[0121] The term "plants" refers to all the physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[0122] It is understood that the term "plant propagation material" means generative parts of the plant, such as seeds, that can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example, potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Germinated plants and young plants that will be transplanted after germination or after emergence from the soil can also be mentioned. These young plants can be protected before transplantation by total or partial immersion treatment. Preferably, "plant propagation material" is understood to mean seeds.

[0123] The compounds of Formula (1) 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 wettable emulsions, soluble powders, dust, granules and also encapsulations, for example, in polymeric substances. Like 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 additional adjuvants such as stabilizers, defoamers, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations to obtain special effects.

[0124] Suitable carriers and adjuvants, for example, for agricultural use, can be solid or liquid and are substances useful in formulation technology, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackiness promoters, thickeners , binders or fertilizers. Such carriers are described, for example, in WO 97/33890.

[0125] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may additionally include a wetting agent to increase 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.

[0126] Wettable powders are in the form of finely divided particles that rapidly disperse in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include Fuller's soil, kaolin clays,

silicas and other organic or inorganic solids readily moistened. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0127] 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 solvents " non-volatile organic compounds. In use, these concentrates are dispersed in water or another liquid and usually applied as a spray to the area to be treated. The amount of active ingredient can vary from 0.5% to 95% of the concentrate.

[0128] Granular formulations include both extruded and relatively coarse particles and are usually applied without dilution to the area where treatment is required. Typical carriers for granular Formulations include sand, Fuller earth, atapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials that absorb or can be coated with the active compound. Formulations

Granulars 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.

[0129] 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.

[0130] Microcapsules are typically droplets or granules of the active ingredient encased in an inert porous shell that allows the enclosed material to escape into the vicinity at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and can include 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 11 cm and preferably 1 to 2 millimeters in diameter. The granules are formed by extrusion, agglomeration or pelletizing, or they occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, atapulgite clay, sawdust and granular coal. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,

polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0131] Other formulations useful for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprayers can also be used, in which the active ingredient is dispersed in finely divided form due to the vaporization of a dispersing solvent carrier with a low boiling point.

[0132] 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.

[0133] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, ether ether diethylene glycol methyl, N, N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethyl-hexanol, carbon, 1.1-

trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol, hexane, hexane, glycerol, hexane, hexane isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methylisoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl chloride, octane methylene, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monoethyl ether, p - xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isoprop anol and higher molecular weight alcohols, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is usually the carrier of choice for diluting concentrates.

[0134] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, atapulgite clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller earth, bark cottonseeds, wheat flour, soy flour, pumice stone, wood flour, nutshell flour and lignin.

[0135] A wide range of surfactants is advantageously employed in said liquid and solid compositions, especially those designed to be diluted with a carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surfactants include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol Cisg-ethoxylate; alcohol-alkylene oxide addition products, such as C1-6 tridecyl alcohol ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di (2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

[0136] 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, agents - “antifoaming agents , sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, flavorings, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0137] Additionally, yet, 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 biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0138] Pesticide agents are referred to here using their common name; they are known, for example, from “The Pesticide Manual”, 15th Edition British Crop Protection Council 2009.

[0139] Additionally, the compositions of the invention can also be applied with one or more inductors of systemically acquired resistance ("SAR" inductor). SAR inducers are known and described, for example, in United States Patent No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0140] The compounds of Formula (II) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or successively with additional compounds. These additional compounds can be, for example, fertilizers or micronutrient donors or other preparations that influence plant growth. They can also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired in conjunction with additional carriers, surfactants or application-promoting adjuvants commonly employed in the formulation technique.

[0141] The compounds of Formula (1) 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 (II) or at least one preferred individual compound as defined here, in free form or in the form of agrochemically usable salt, and at least one of the aforementioned adjuvants.

[0142] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of the Formula (LI), an agriculturally acceptable carrier and optionally an adjuvant. An acceptable agricultural carrier is, for example, a carrier that is suitable for agricultural use. Agricultural conveyors 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 (1).

[0143] The compound of Formula (I) may be the only active ingredient in a composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator, where appropriate . An additional active ingredient can, in some cases, result in unexpected synergistic activities.

[0144] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzanidide, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, fungicides, fungicides dithiolane, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorus fungicides, organotinned fungicides, oxatiin fungicides, oxazole fungicides, phenyl fungicides, fungalides python ol, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazole fungicides , thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

Examples of suitable additional active ingredients also include the following: (3-difluoromethyl-1-acid) (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl) -amide 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid methyl-1H-pyrazol-4-carboxylic acid, methoxy- [1-methyl-2- (2,4,6-trichlorophenyl) -ethyl] -amide , 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl) (1072957- 71-1), (4 ' 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid-methylsulfanyl-biphenyl-2-yl, [2- (2,4-dichloro-phenyl) -2-methoxy-1-methyl- 1-methyl-3-difluoromethyl-4H-pyrazol-4-carboxylic acid ethyl] -amide, (5-Chloro-2,4-dimethyl-pyridin-3-yl) - (2,3,4-trimethoxy-6 -methyl-phenyl) - methanone, (5-Bromo-4-chloro-2-methoxy-pyridin-3-yl) - (2,3,4-trimethoxy-6-methyl-phenyl) -methanone, 2- (2 - [(E) -3- (2,6- Dichloro-phenyl) -l-methyl-prop-2-en- (E) -ylidenoamino-

oxymethyl] -phenyl) -2 - [(Z2) -methoxyimino] -N-methyl-acetamide, 3- [5- (4-Chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] - pyridine, (E) -N-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxyiminoacetamide, 4-bromo-2-cyano-N, N-dimethyl-6- trifluoromethylbenzimidazole-1 -sulfonamide, a- [N- (3-chloro-2,6-xylyl) -2-methoxyacetamido] -yl-butyrolactone, 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-l -sulfonamide, N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide, N- (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propionamide, N- (2 -methoxy-5-pyridyl) -cyclopropanecarboxamide, (. + -.) - cis- 1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-11-yl) -cycloheptanol, 2 - (1-tert-butyl) -1- (2-chlorophenyl) -3- (1,2,4-triazol-1-11) - propan-2-ol, 2 ', 6'-dibromo-2-methyl -4-trifluoromethoxy-4'-trifluoromethyl-l1,3-thiazol-5-carboxanilide, l1-imidazolyl-1- (4'-chlorophenoxy) -3,3-dimethylbutan-2-one, (E) -2- [ Methyl 2- [6- (2- cyanophenoxy) pyrimidin-4-yloxy] phenyl] 3-methoxyacrylate, (E) -2- [2- [6- (2-thioamidophenoxy) pyrimidin-4-yl xi] methyl phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [ Methyl 2- [6- (2,6-di-fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] methyl phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (S-methylpyrimidin-2-yloxy) - phenoxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [2 - methyl [3- (phenyl-sulfonyloxy) phenoxy] phenyl-3-methoxyacrylate, (E) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methyl-methoxyacrylate, (E) Methyl -2- [2-phenoxyphenyl] -3-methoxyacrylate, (E) -2- [2- (3,5-dimethyl-benzoyl) pyrrol-11-yl] -3-methyl methoxyacrylate, (E) - Methyl 2- [2- (3-methoxyphenoxy) phenyl] -3-methoxyacrylate, (E) -2- [2- (2-phenyleten-1-yl) -phenyl] -3-methoxyacrylate, (E) -2- [2- (3,5-dichlorophenoxy) pyridin-3-yl] -3-methyl methoxyacrylate, (E) -2- (2- (3- (1,1,2,2-tetrafluoroethoxy) phenoxy ) methyl phenyl) -3- methoxyacrylate, (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3 -methyl methoxyacrylate, (E) -2- (2- (4-phenoxypyridin-2-yloxy) phenyl) -3-methyl methoxyacrylate, (E) -2- [2- (3-n-propyloxy-phenoxy) methyl phenyl] -3- methoxyacrylate, (E) -2- [2- (3-isopropyloxyphenoxy) phenyl] -3-methyl methoxyacrylate, (E) - 2- [2- [3- (2-fluorophenoxy) phenoxy ] methyl phenyl] -3-methoxyacrylate, (E) -2- [2- (3-ethoxyphenoxy) phenyl] -3-methyl methoxyacrylate, (E) -2- [2- (4-tert-butyl-pyridin) Methyl -2-yloxy) phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (3- cyanophenoxy) phenoxy] phenyl] -3-methyl methoxyacrylate, (E) - 2- [2 - Methyl [(3-methyl-pyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-methyl-phenoxy) pyrimidin-4-yloxy] phenyl] - Methyl 3-methoxyacrylate, (E) -2- [2- (5-bromo-pyridin-2-yloxymethyl) phenyl] -3-methyl-methoxyacrylate, (E) -2- [2- (3- (3- methyl iodopyridin-2-yloxy) phenoxy) phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-chloropyridin-3-yloxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate methyl, (E), (E) -2- [2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl) f methyl enyl] -3-methoxyacrylate, (E) - 2- (2- [6- (6-methylpyridin-2-yloxy) pyrimidin-4-yloxy] phenyl);) - methyl 3-methoxy acrylate, ( E), (E) -2- (2- (3-methoxyphenyl) methyloximinomethyl] -phenyl) -3-methyl-methoxyacrylate, (E) -2- (2- (6- (2-azidophenoxy) -pyrimidin-4 - methyl yloxy] phenyl) -3-methoxyacrylate, (E), (E) -2- (2- [6-

methyl phenylpyrimidin-4-1yl) -methyloximinomethyl]; - methyl 3-methoxyacrylate, (E), (E) -2- (2- [(4-chlorophenyl) -methyloximinomethyl] -phenyl) -3-methoxyacrylate , (E) - 2- (2- [6- (2-n-propylphenoxy) -1,3,5-triazin-4-yloxy] phenyl) -3-methyl methoxyacrylate, (E), (E) - 2- (2 - [(3-nitrophenyl) methyloximinomethyl] phenyl) -3-methyl-methoxyacrylate, 3-chloro-7- (2-aza-2,7,7T-trimethyl-oct-3-en-5-ino ), 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargylformal, 3-bromo-2,3-di-iodo-2 ethylcarbamate -propenyl, 2,3,3-triiodiodoalyl alcohol, 3-bromo-2,3-diiodine-2-propenyl alcohol, 3-iodine-2-propynyl n-butylcarbamate, 3-iodine n-hexylcarbamate -2-propynyl, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenylcarbamate; phenol derivatives, such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4- chlorophenol, 5-hydroxy-2 (5H) -furanone; 4,5-dichlorodithiazolinone, 4,5-benzoditiazolinone, 4,5-trimethylenedithiazolinone, 4,57 dichloro- (3H) -1,2-dithiol-3-one, 3,5-dimethyl-tetrahydro-1,3 , 5-thiadiazine-2-thione, N- (2-p-chlorobenzylethyl) -hexamine chloride, acibenzolar, acipetacs, alanicarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradine, amisulbrom, amobam, ampropylphos, aniline, aniline aureofungin, azaconazole, azafendine, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanyl, benomyl, benquinox, bentaluron, bentiavalicarb, bentiazole, benzalkonium chloride,

benzamacril, benzamorph, benzohydroxamic acid, benzovindiflupir, berberine, betoxazine, biloxazole, binapacril, biphenyl, bitertanol, bitionol, bixafen, blasticidin-S, boscalide, bromotalonil, bromuconazole, bupyrimalt, butane, polypeptide, butylate, polypeptide, butylate , carbamorph, carbendazim, carbendazim hydrochloride, carboxine, carpropamide, carvone, CGA41396 CGA41397, quinomethionate, chitosan, clobentiazone, chloraniformethane, chloranil, chlorphenazol, chloroneb, chloropicrin, chloro-chloro, chloro-chloro, chloro such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper talate, copper and zinc chromate and Bordeaux mixture, cresol, cufranebe, cuprobam, cuprous oxide, cyzofamide, cyclamfuramide, cycloheximide, cyflufenamide, cymoxanil, cipendazole, cyproconazole, ciprod inyl, dazomete, debacarb, decafentin, dehydroacetic acid, di-2-pyridyl disulfide 1,1'-dioxide, diclofluanide, diclomezine, diclone, dichloran, dichlorophene, diclozoline, diclobutrazol, diclocimet, dietofencarb, difenatol, difenoconazole O, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimetconazole, dimetomorph, dimethyrimol, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, diphenylamine, diphenylamine, diphenylamine ditalimphos, dithianon, dithioether, dodecyldimethylammonium chloride, dodemorph, dodicin, dodine, doguadine, drazoxolon, edifenfos, enestroburin,

epoxiconazole, etaconazole, etem, etaboxam, ethirimol, ethoxyquin, ethylicin, (Z) -N-benzyl-N - ([methyl (methylthioethylideneamino-oxycarbonyl) amino] thio) -ethylalaninate, etridiazol, famoxadone, phenoxadone, famoxadone, phenoxadone , fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenexamide, fenitropane, fenoxanil, fenpiclonil, fenpicoxamide, fenpropidina, fenpropimorfe, fenpirazamine, fentina acetate, fentine hydroxide, flimicam, flimidone, flimidone, flimidone , fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flussulfamide, flutanil, flutolanil, flutriafol, fluxpyroxade, leaflet, formaldehyde, fosetil, fuberidazole, furalaxil, furametpir, furcarbanil, furconazol, furconazol, furconazol, furconazol, furconazol, furconazol , hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydrargafene, hydroxy-isoxazole, himexazole, imazalil, imazalil sulfate, imibenconazole, iminoctadine, t iminoctadine riacetate, inezine, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanylbutyl carbamate, isoprothiolan, isopirazam, isotianil, isovaledione, izopamz2, izopamz2, mebenyl, mecarbinzide, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercury chloride, meptildinocape, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole metasulfide, methomethoxy, methoxylamine, bromide -zinc,

metominostrobin, metrafenone, metsulfovax, milnebe, moroxidine, myclobutanil, myclozoline, nabam, natamycin, neoasozine, nickel dimethyldithiocarbamate, nitrosstyrene, nitrotal-iso-propyl, nuarimol, octilin, oxyturin, oxyturin, oxyuron, oxide oxatiapiproline, oxin-copper, oxolinic acid, oxpoconazole, oxycarboxine, parinol, pefurazoate, penconazole, pencicuron, penflufen, pentachlorophenol, pentiopyrade, fenamacril, phenazine oxide, phosdiphen, phosethyl-aldehyde, pitubide, phosphate acid, phosphoric acid, phosphoric acid , polyoxin D, polyoxrim, poliram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propynabe, propionic acid, proquinazide, protiocarb, protioconazole, pidiflumetofen, piracarbolide, pyraclostrobin, pyretoxyrobin, pyretoxyrazyrine, pyrethyrobrazyrine , pyriophenone, piroquilon, piroxiclor, piroxifur, pyrrolnitrina, ammonium compounds q uaternary, quinacetol, quinazamide, quinconazole, quinomethionate, quinoxifene, quintozene, rabenzazole, santonine, silkxane, siltiofam, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, sultropene, tebuconamol, tebuconazol, tebuconazol, tebuconazol, tebuconazol, tebuconazole thiabendazole, thiadifluorine, thiocophene, thifluzamide, 2- (thiocyanomethylthio) benzothiazole, thiophanate-methyl, thioquinox, thiamine, thiadinyl, thymibonconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimefon, triadimide, triadimide, triadimide , trifloxystrobin, triflumazole,

triforin, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozoline, zarilamide, zineb, ziram and zoxamide.

[0145] The compounds of the invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the class of macrocyclic lactone compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP-357460, EP- 444964 and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxybendazole, parbendazole and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include fluquicides, such as triclabendazole and clorsulon, and cestocides, such as praziquantel and epsiprantel.

[0146] The compounds of the invention can be used in combination with derivatives and analogs of the class of paraherquamide / marcfortin anthelmintic agents, as well as antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE-19520936 .

[0147] 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 active anthelmintic cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP O 626 375, EP O 382 173, WO 94/19334, EP O 382 173 and EP O 503 538.

[0148] The compounds of the invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.

[0149] The compounds of the invention can be used in combination with terpene alkaloids, for example, those described in International Patent Application Publications Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.

[0150] Other examples of such biologically active compounds with which the compounds of the invention can be used in combination include the following, but are not restricted to these: Organophosphates: acephate, azametiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos -ethyl, cadusaphos, chlorethoxyphos, chlorpyrifos, chlorfenvinfos, chlormphs, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialiphos, diazinon, dichlorvos, dichrotophos, dimetoate, disulfoton, etion, etoprofos, fenifos, fenfosam, fenetros, , fensulfotion, fention, flupirazofos, formotion fonofos, fostiazato, heptenofos, isazofos, isothioato, isoxation, malation, metacrifos, metamidofos, metidation, methyl-paration, mevinfos, monocrotofos, nalede, metetoate, paremoxation, paremoxation, paroxoxation methyl, phentoate, fosalone, phospholane, fosfocarb, fosmet, fosfamidon, forato, foxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proetamfos, protiofos, piraclofos, piridapention, quinalfos, sulprofos, tem efos, terbufos, tebupirimfos, tetrachlorvinfos, timeton, triazofos, triclorfon, vamidotion.

[0151] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloetocarb, etiofencarb, phenoxycarb, fentiocarb, methacrocarb, methoxy, 5-carcinyl, isoprocarb, 5 -m- cumenylbutyryl (methyl) carbamate, oxamil, pyrimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

[0152] Pyrethroids: acrinatin, alethrin, alfamethrin, (E) - (1R) -cis-2,2-dimethyl-3- (2-oxothiolan-3-ylidenomethyl) 5-benzyl-3-furylmethyl, bifenthrin, cyclopropanecarboxylate beta-cyfluthrin, cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioalethrin, bioalethrin (isomer (S) -cyclopentyl), biormethrin, bifenthrin, NCI- 85193, cycloprotrin, cyhalothrin, cyttrin, cyphenothrin, emtenthetrin, emptametrine, deltametrine, deltametrine, emptamethine, fenflutrin, fenpropatrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin,

tetramethrin, transflutrin, theta-cypermethrin, silafluofen, t-fluvalinate, teflutrin, tralometrine, Zeta-cypermethrin

[0153] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas clorfluazuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, chlorofluorine, triflazoline, triflazurine, triflazoline, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine, triflazurine. b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxifene, methoprene (including smethoprene), phenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0154] Other antiparasitic agents: acequinocil, amitraz, AKD-1022, ANS-118, azadiractin, Bacillus thuringiensis, bensultap, biphenazate, binapacril, bromopropylate, BTG-504, BTG-505, camfeclor, cartap, chlorfenzyme, chlorobenzide , clothianidin, cyromazine, diaclodene, diafentiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, etiprol, etofenprox, phenazaquin, flumite, MTI-800, flpyroxin, fluorimine, fluorimine, fluorimine , fluproxifene, halofenprox, hydramethylnon, IKI-220, canemite, NC-196, Neemgard, nidinorterfuran, nitenpiram, SD-35651, WL-108477, pyridine, propargite, protrifenbute, pimetrozine, pyridine, 11-pyridine, pyridine, pyridine, 11 , RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpirade, tetradifon, tetranactin,

thiacloprid, thiocyclam, thiamethoxam, tolfenpirade, triazamate, triethoxyspinosine, trinactin, verbutine, vertalec, YI-5301.

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

[0155] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0156] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprol, cefquinoma, florfenicol, buserelin, cefovantine, cefovecin, trefovecin, trefovinine, cefovecin, trefovinine, cefovecin, trefovina, .

[0157] The following mixtures of the compounds of the formula (1) with active ingredients are preferred. The abbreviation “TX” means a compound selected from the group consisting of the compounds represented in Tables 1.1A through 1.8A, Tables 1.1B through 1.8B, Tables 2.1A through 2.3A, Tables 2.1B through 2.3B (below), or a compound 1.1 to 1.10 described in Table T1 (below) or a compound 2.1 to 2.80 described in Table T2 (below).

an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX, an acaricide selected from the group of substances consisting of 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (IUPAC name) ( 910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC / Chemical Abstracts name) (1059) + TX, 2-fluoro-N-

methyl-Nl-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinatrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidition (870) + TX, amidoflumete [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogenoxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenious oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotine (46) + TX, nitrogen (889) + TX , benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoxide (71) + TX, benzyl benzoate (IUPAC name) [CCN] + TX, biphenazate (74) + TX, bifenthrin (76) + TX, binapacril (907) + TX, brofenvalerate (alternative name) + TX, bromocyclene (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) + TX, bup rofezin (99) + TX, butocarboxy (103) + TX, butoxycarboxy (104) + TX, butylpyridabene (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbofenotion (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, clorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorophenethol (968) + TX, chlorophensone (970) + TX, chlorfensulfide (971) + TX, chlorfenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX,

chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, clofentezina (158) + TX, closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (1010) + TX, cufranebe (1013) + TX, cyantoate (1020) + TX, cyphlumetophen (Reg.

CAS: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefion ( 1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton- O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialects (1042 ) + TX, diazinon (227) + TX, diclofluanide (230) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicofol (242) + TX, dicrotofos (243) + TX, dienochlor (1071 ) + TX, dimefox (1081) + TX, dimetoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobuton (269) + TX, dinocape (270) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon ( 1098) + TX, dioxation (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram (no me alternative) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endotion ( 1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, etoate-methyl

(1134) + TX, ethoxazole (320) + TX, etrimphos (1142) + TX, phenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropatrin (342) + TX, fenpirade (alternative name) + TX, fenpyroximate (345) + TX, fenson (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacripyrim (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, gamma- HCH (430) + TX, gliodine (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC name / Chemical Abstracts) (1216) + TX, hexithiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophones (alt name (473) + TX, Oo- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, Jasmine I (696) + TX, Jasmine II (696) + TX, jodfenfos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malation (492) + TX, malonobene (1254) + TX, mecarbam (502) + TX, mephosfolan (1261) + TX, messulfene (alternative name) [CCN] + TX, methacrifos (1266) + TX, metamidophos (527) + TX, metidation (529) + TX, metiocarb (530) + TX, methyl (531) + TX, bromide methyl (537) + TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293 ) + TX, monocrotofos (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, nalede (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nicomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb complex 1: 1 c zinc loride (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxisulfoton (1325) + TX, pp'-DDT (219) + TX, paration (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencaptona (1330) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmete (638) + TX, phosphamidon (639) + TX, foxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacil (1354 ) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protoate (1362) + TX, pyrethrin LI (696) + TX, pyrethrin II ( 696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX, pyridafention (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, quinalfos (711) + TX, quintiofos (1381 ) + TX, R -1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, escradano (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sofamide (1402) + TX, spirodiclofen (738) + TX, spiromesifene (739) + TX, SSI-

121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotepe (753) + TX, sulfur (754) + TX, SZI-l21 (code of development) (757) + TX, tau-fluvalinate (398) + TX, tebufenpirad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinfos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, tiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiophanox (800) + TX, tiometon (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorphon (824 ) + TX, triphenophones (1455) + TX, trinactin (alternative name) (653) + TX, vamidotion (847) + TX, vaniliprol [CCN] and YI-5302 (compound code) + TX,

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

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

[CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737 ) and thiophanate (1435) + TX,

an avicide selected from the group of substances consisting of chloralose (127) + TX, endrine (1122) + TX, fention (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX,

a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX , dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafene (alternative name) [CCN] + TX, casugamycin ) + TX, hydrated casugamycin hydrochloride (483) + TX, nickel bis (dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapirin (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinolinosulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, keyboard software (766) + TX, and thiomersal (alternative name) [CCN] + TX,

a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) +

TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani ( alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide ( scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus montrouzieri ( alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (name (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, Bacillus subtilis var. amyloliquefaciens Strain FZB24 (made available by Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA and known by the trade name TaegroO) + TX,

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

a chemosterilizer selected from the group of substances consisting of afolate [CCN] + TX, bisazir

(alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiote [CCN] + TX, methyl afolate [CCN] + TX, morzide [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX , thio-hempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

an insect pheromone selected from the group of substances consisting of (E) -dec-5-en-l-yl acetate with (E) -dec-5-en-l1-0l (IUPAC name) (222) + TX, (E) - tridec-4-en-l-yl acetate (IUPAC name) (829) + TX, (E) -6-methyl-hept- 2-en-4-0l (IUPAC name) (541) + TX, (E, Z) acetate - tetradeca-4,10-dien-l-yl (IUPAC name) (779) + TX, (Z) -dodec-7-en-l-yl acetate (IUPAC name) (285) + TX, (Z) - hexadec-ll1-enal (IUPAC name) (436) + TX, (Z2) - hexadec-l1-en-l-yl acetate (IUPAC name) (437) + TX, (Z2) - hexadec-13-en-l1-in-l1-yl acetate (IUPAC name) (438) + TX, (Z) -icos- 13-en-l10-one (IUPAC name) (448) + TX, (Z) -tetradec-7-en-l- al (IUPAC name) (782) + TX, (Z) -tetradec-9-en-l-ol (IUPAC name) (783) + TX, acetate (Z) -tetradec-9-en-l-yl (IUPAC name) (784) + TX, (7E, 9Z) -dodeca-7,9-dien-l-yl acetate (IUPAC name) (283) + TX, (9Z, 11E) -tetradeca-9,11- dien-l-yl acetate (IUPAC name) (780) + TX, (9Z, 12E) acetate - tetradeca-9,12-dien-l1-ila (IUPAC name) (781) + TX, 14- methyloc tadec-l-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (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-en-l-yl acetate (IUPAC name) (286) + TX, dodec-9-en-l1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, acetate 10-dien-l-ila (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN ] + TX, front (alternative name) [CCN] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name ) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (name alternative) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methylphenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2 acetate , 13-dien-l-ila (IUPAC name) (588) + TX, octadeca-3,13-dien-l-ila (IUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, orictalure (alternative name) (317) + TX, ostramona (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidine (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-l1-en-l1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B; (alternative name) (839) + TX, trimedlure B>

(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, 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 l-dichloro-l-nitroethane (IUPAC / Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis (4-ethylphenyl) ethane (IUPAC name) (1056), + TX, 1.27 dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, l-bromo-2 -chloroethane (IUPAC / Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1- (3,4-dichlorophenyl) ethyl acetate (IUPAC name) (1451) + TX, 2,2-methylphosphate -dichlorovinyl and 2-ethylsulfinylethyl (IUPAC name) (1066) + TX, 2- (1,3-dithiolan-2-yl) phenyl (IUPAC / Chemical Abstracts name) (1109) + TX, 2- (thiocyanate) dimethylcarbamate 2- butoxyethoxy) ethyl (IUPAC / Chemical Abstracts name) (935 + TX, 2- (4,5-dimethyl-1,3-dioxolan-2-yl) methylcarbamate phenyl (IUPAC / Chemical Abstracts name) (1084) + TX, 2- (4-

chloro-3,5-xylyloxy) ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerilindan - 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, 3-bromo-l-chloroprop-l-ene (IUPAC name) (917) + TX, 3-methyl-l-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, methylcarbamate 4-methyl (prop-2-inyl) 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, acetamipride (4) + TX, acetion (alternative name) [CCN] + TX, acetoprol [CCN] + TX, acrinatrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, aldrin (864) + TX, aletrine (17) + TX, alosamidine (alternative name ) [CCN] + TX, alixicarb (866) + TX, alpha-cypermetry na (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidition (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogenoxalate (875) + TX, amitraz (24) + TX, anabasin (877) + TX, atidation (883) + TX, AVI 382 (compound code) + TX, AZ 60541 ( compound code) + TX, azadiractin (alternative name) (41) + TX, azametiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, nitrogen (889) + TX, delta endotoxins from Bacillus thuringiensis (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX,

barium polysulfide (IUPAC name / 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, bioallethrin (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, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (914) + TX, bromocyclene (918) + TX, bromo-DDT (name alternative) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butatiofos (927) + TX, butocarboxy (103) + TX, butonate (932) + TX, butoxycarboxy (104) + TX, butylpyridabene (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camfeclor (941) + TX, carbanolate (943) + TX , carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbofenotion (947) + TX , carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclene (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorfenapyr (130) + TX,

chlorofenvinfos (131) + TX, clorfluazuron (132) + TX, chlorhefos (136) + TX, chloroform [CCN] + TX, chloropicrina (141) + TX, chlorfoxin (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, chromafenozide (150) + TX, cinerin IL (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, cis-resmethrin (alternative name) + TX, schismetrin (80) + TX, clocitrine (alternative name) + TX, cloetocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumafos (174) + TX, coumitoate (1006) + TX, crotamiton (alternative name) [CCN ] + TX, crotoxifos (1010) + TX, crufomato (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanophenphos (1019) + TX, cyanophos (184) + TX, cyantoate (1020) + TX, cyclethrin [CCN] + TX, cycloprotrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cytate (alternative name) [CCN] + TX, d-limonene (alternative name) [CCN] + TX , d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefion (1037) + TX, demefion-O (1037) + TX, demefion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton -O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfone (1039) + TX, diafentiuron (226) + TX, dialysis ( 1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapton (1050)

+ TX, diclofention (1051) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicresil (alternative name) [CCN] + TX, dicrotofos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl phosphate and 5-methylpyrazol-3-yl (IUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimeflutrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinfos (265) + TX, dimethylan (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinosebe (1095) + TX, dinotefuran (271) + TX, diophenolan (1099) + TX, dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxation (1102) + TX, disulfoton (278) + TX, dichrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX , EMPC (1120) + TX, empentrine (292) + TX, endosulfan (294) + TX, endotion (1121) + TX, endrine (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epophenonan (1124) + TX, eprinomectin (alternate name) [CCN] + TX, sphenvalerate (302) + TX, etafos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, etion (309) + TX, etiprol (310) + TX, etoate-methyl (1134) + TX, etoprofos (312) + TX, ethyl format (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, dibromide ethylene (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimphos (1142) + TX, EXD (1143) + TX , famfur (323) + TX, fenamiphos (326) +

TX, fenazaflor (1147) + TX, phenclorphos (1148) + TX, fenetacarb (1149) + TX, fenflutrina (1150) + TX, fenitrotion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX , phenoxycarb (340) + TX, phenpiritrin (1155) + TX, fenpropatrin (342) + TX, fenpirade (alternative name) + TX, fensulfotion (1158) + TX, fention (346) + TX, fention-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamide (358) + TX, flubendiamide (CAS. Of Reg.

CAS: 272451-65-7) + TX, flucofuron (1168) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenerin [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, phonophos (1191) + TX, formethanate (405) + TX , formethanate hydrochloride (405) + TX, formotion (1192) + TX, formparanate (1193) + TX, phosmethylan (1194) + TX, phospirate (1195) + TX, phostiazate (408) + TX, fostietane (1196) + TX, furatiocarb (412) + TX, furetrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquinc arbe (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, o- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, isoprothiolan (474) + TX, isothioate (1244) + TX, isoxation (480) + TX, ivermectin (alternative name) [CCN] + TX, Jasmine I (696) + TX, Jasmine II (696) + TX, jodfenfos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimphos (1251) + TX, lufenuron (490) + TX, litidation (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malation ( 492) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarfon (1258) + TX, menazon (1260) + TX, mephosphola no (1261) + TX, mercury chloride (513) + TX, messulfenphos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam potassium (alternative name) (519) + TX, metam -sodium (519) + TX, methacrifos (1266) + TX, metamidophos (527) + TX, methanesulfonyl fluoride (IUPAC / Chemical Abstracts name) (1268) + TX, metidation (529) + TX, metiocarb (530) + TX, metocrotofos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methotrine (alternative name) (533) + TX, methoxychlor (534) + TX , methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methyl chloroform (alternative name) [CCN] + TX, methylene chloride [CCN] +

TX, metoflutrin [CCN] + TX, metolcarb (550) + TX, methoxyzone (1288) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nalede (567) + TX, naphthalene (IUPAC / Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpiram (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, novaluron (585) + TX , noviflumuron (586) + TX, O-5-dichloro-4-iodophenyl ethyl phosphonothioate and O-ethyl (IUPAC name) (1057) + TX, phosphorothioate of O, O-diethyl and O-4-methyl-2-oxo-2H-chromen- 7-yl (IUPAC name) (1074) + TX, O phosphorothioate, O-diethyl and O-6-methyl-2-propylpyrimidin -4-yl (IUPAC name) (1075) + TX, 0.0,0 'dithiopyrophosphate, O'-tetrapropyl (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxidemeton-methyl (609) + TX, oxideprofos (1324) + TX, oxisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [ CCN] + TX, paration (615) + TX, paration-methyl (616) + TX, penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH

60-38 (development code) (1328) + TX, fencaptona (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, fosmete (638) + TX, fosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (IUPAC name) (640) + TX, foxim (642) + TX, foxim-methyl (1340 ) + TX, pyrimetaphos (1344) + TX, pirimicarb (651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychlorinated terpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II ( alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidofos (1349) + TX, profenofos (662) + TX, proflutrina [CCN] + TX, promacil (1354) + TX, promecarbe (1355) + TX, propafos (1356) + TX, propetamfos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protiofos (686) + TX, prot oato (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclofes (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalil (700) + TX, pyridafention (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, pyriproxifene (708) + TX, quássia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfosmethyl (1376) + TX, quinotion (1380) + TX, quintiofos (1381) + TX, R- 1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryan (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadila (alternative name) (725) + TX, escradano (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (code compound) + TX, SI-O0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, arsenite sodium [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC / Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sofamide (1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotepe (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils ( alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpirad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, teflutrin (769) + TX, temefos (770) + TX, TEPP (1417) + TX, teralethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinfos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiaclopride (791 ) + TX, tiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX,

thiocyclam hydrogenoxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800) + TX, thiometon (801) + TX, thionazine (1434) + TX, tiossultap (803) + TX, thiossultap-sodium (803) + TX, thuringianensin (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, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, triphenophos ( 1455) + TX, triflumuron (835) + TX, trimetacarb (840) + TX, triprene (1459) + TX, vamidotion (847) + TX, vaniliprol [CCN] + TX, veratridine (alternative name) (725) + TX , veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name ) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantr aniliprol [736994-63-19 + TX, chlorantraniliprol [500008-45-7] + TX, cyienopyraphene [560121-52-0] + TX, cyphlumetophen [400882-07-7] + TX, pyrifluquinazone [337458-27-2 ] + TX, espinetoram [187166-40-1 1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0 ] + TX, meperflutrin [915288-13-0] + TX, tetramethylflutrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/092115) + TX,

a molluscicide selected from the group of substances consisting of bis (tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate

[CCN] + TX, cloetocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metalldehyde (518) + TX, metiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name ) (347) + TX, pyriprole [394730- 71-3) + TX,

a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (name - IUPAC / Chemical Abstracts) (1045) + TX, 1,2-dichloropropane (name IUPAC / Chemical Abstracts) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 1,1-1-dioxide 3 , 4-dichlorotetrahydrothiophene (IUPAC / Chemical Abstracts name) (1065) + TX, 3- (4-chlorophenyl) -5-methylrodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-l acid , 3,5-thiadiazinan-3-ylacetic (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprol [CCN] + TX, alanicarb (15 ) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridabene (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (14 5) + TX, cloetocarb

(999) + TX, cytokinins (alternative name) (210) + TX, dazomete (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, diclofention (1051) + TX, diclifos (alternative name) + TX, dimetoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [ CCN] + TX, etoprofos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpirade (alternative name) + TX, fensulfotion (1158) + TX, fostiazate (408) + TX, fostietano (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarfon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, mi lbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, composition of Myrothecium verrucaria (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamil ( 602) + TX, phorate (636) + TX, phosphamidon (639) + TX, fosfocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX,

YI-5302 (compound code) and zeatin (alternative name (210) + TX, fluensulfone [318290-98-1] + TX,

a nitrification inhibitor selected from the group of substances consisting of potassium ethyl xanthate [CCN] and nitrapirin (580) + TX,

a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,

a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, alpha- 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, coumafuril (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, diphthialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafene (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magn phosphide osmium (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, matt (1336) + TX, phosphine (IUPAC name) (640) + TX,

phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, escilirosida (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide ( 444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,

a synergist selected from the group of substances consisting of 2- (2-butoxyethoxy) ethyl piperonylate (IUPAC name) (934) + TX, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex- 2-enona (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolina (1394 ) and sulfoxide (1406) + TX,

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

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

a wound protector selected from the group of substances consisting of mercuric oxide (512) + TX, octyline (590) and thiophanate-methyl (802) + TX,

and biologically active compounds selected from the group consisting of ametoctradine [865318-97-4] + TX, amisulbrom [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzovindiflupir [1072957-71-1] + TX, bitertanol [70585-36-3] + TX, bixafen [581809-46-3] + TX, bromuconazole [116255- 48-2] + TX, coumoxystrobin [850881-70-8] + TX, cyproconazole [94361 -06-5] + TX, diphenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [238410-11-2] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369- 43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluqguinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674- 21-0] + TX, fluxpyroxade [907204-31-3] + TX, fluopyram [658066-35-4] + TX, phenaminstrobin [366815-39-6] + TX, isofetamide [875915-78-9] + TX , hexaconazole [79983-71- 4) + TX, imazalil [35554-44-0] + TX, imibenconazole [86598- 92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08 -1] + TX, isothianyl [224049-04-1] + TX, mandestrobi na [173662-97-0] (can be prepared according to the procedures described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [125116- 23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30-4] + TX, penflufen [494793-67-8] + TX, penconazole [66246-88-6 ] + TX, protioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [ 149508-90-7] + TX, tebuconazole [107534-

96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX , triticonazole [131983-72-7] + TX, ancimidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43 -6] + TX, dimethyrimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, phenpropidine [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552- 61-2] + TX, mepanipirim [110235-47- 7] + TX, pyrimethanil [53112-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, fluindapyr [1383809-87-7] + TX, benalaxyl [71626-11-4] + TX, furalaxil [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48 -3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-7 9-8] + TX, clozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX , procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, boscalide [188425-85-6

+ TX, carboxine [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332-96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814 -41-0] + TX, oxycarboxine [5259-88-1] + TX, pentiopyrade [183675-82-3] + TX, tifluzamide [130000-40- 7] + TX, guazatin [108173-90-6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961- 52-4] + TX, enestroburin (Proc.

BCPC, Int.

Congr.,

Glasgow, 2003, 1, 93) + TX, fluoxastrobin [361377-29-9] + TX, cresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517- 21-7] + TX, orisastrobin [248593-16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, piraoxystrobin [862588-11-2] + TX , ferbam [14484-64-1] + TX, mancozebe [8018-01-7] + TX, manebe [12427-38-2] + TX, met [9006- 42-2] + TX, propineb [12071-83 -9] + TX, remove [137-26-8] + TX, zinebe [12122-67-7] + TX, remove [137-30-4] + TX, captafol [2425-06-1] + TX, captana [133-06-2] + TX, dichlofluanide [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-07-3] + TX, tolylfluanide [731-27- 1] + TX, Bordeaux mixture [8011-63-0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758- 98 -7] + TX, copper oxide [1317-39-1] + TX, maneuver [53988- 93-5] + TX, oxine-copper [10380-28-6] + TX, dinocape [131-72- 6 ] + TX, nitrotal-isopropyl [10552-74-6] + TX, edifenfos [17109-49-8] + TX, iprobenfos [26087-47-8] + TX, isoprothiolan [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18- 6] + TX, tolclofos-methyl [57018-04- 9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35- 7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, chloronebe [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX , cyflufenamide [180409-60-3] + TX, cymoxanil [57966-95- 7] + TX, diclone [117-80-6] + TX, diclocimet [139920-32-4] + TX, diclomezine [62865-36 -5] + TX, dichloran [99-30-9] + TX, dietofencarb [87130-20-9] + TX, dimetomorph [110488-70- 5] + TX, SYP-LI90O (Flumorf) [211867-47- 9] + TX, dithianon

[3347-22-6] + TX, etaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, phenamidone [161326-34-7 ] + TX, phenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [ 239110-15-7] + TX, flussulfamide [106917-52-6] + TX, fenexamide [126833-17-8] + TX, fosetyl 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, pencicuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [ 11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12-4] + TX, pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyrokylone [57369-32-1] + TX, pyrophenone [688046-61-9] + TX, pyribencarb [799247-52-2] + TX, pyrisoxazole [847749 -37-5] + TX, quinoxifene [124495-18-7]) + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX, Timorex Gold "" (plant extract containing oil from the Stockton Group tea) + TX, tebufloquine [376645- 78-2] + TX, thiadinyl [223580-51-6] + TX, triazoxide [72459- 58-6] + TX, tolprocarb [911499-62-2] + TX, triclopyricarb [902760-40-1] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, valiphenalate [283159- 90-0] + TX, zoxamide (RH7281) [156052- 68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, fenamacril + TX, silkxane [874967 -67-6] + TX, trinexapac-ethyl [95266-40-3] + TX, (9-

3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-yl (disclosed in WO 2007 / 048556) + 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3 ', 4', 5 ', 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, 12b -decahydro-6,12-dihydroxy-4,6a, 12b-trimethyl-11-0x0-9- (3-pyridinyl) -2H, 11l1H-naphtho [2,1-b] pyran [3,4 -e] pyran-4-yl] 1-methyl-cyclopropanecarboxylate [915972-17-7] + TX and 1,3,5-trimethyl-N- (2-methyl-1-oxopropyl) -N- [3- (2- methylpropyl) -4- [2,2, 2-trifluoro-1-methoxy-1- (trifluoromethyl) ethyl] phenyl] -1H-pyrazol-4-carboxamide [926914-55-8] + TX,

or a biologically active compound selected from the group consisting of N- [(5-chloro-2-isopropyl-phenyl) methyl] - N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-pyrazole-4- carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6- Dimethyl-1H, 5H- [1,4] dithiine [2,3-c: 5,6-c '] dipyrrol- 1,3,5,7 (2H, 6H) -tetrone (can be prepared according to the procedures described in Wo 2011/138281) + TX, 6-ethyl-5,7-dioxo-pyrrole [4 , 5] [1,4] dithiine [1,2-c] isothiazole-3-carbonitrile + TX, 4- (2-bromo-4-fluoro-phenyl) -N- (2-chloro-6-fluoro -phenyl) -2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedures described in WO 2012/031061) + TX, 3- (difluoromethyl) -N- (7-fluoro-1,1 , 3-trimethyl-indan-4-yl) -1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 1 3- l1-dioxide

(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole (can be prepared according to the procedures described in the document in WO 2007/129454) + TX, 2- [2- [ (2,5-dimethylphenoxy) methyl] phenyl] -2-methoxy-N-methyl-acetamide + TX, 3- (4, 4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl ) quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2- [2-fluoro-6 - [(8-fluoro-2-methyl-3-quinolyl) oxy] phenyl] propan- 2- ol (can be prepared according to the procedures described in WO 2011/081174) + TX, 2- [2 - [(7,8-difluoro-2-methyl-3-quinolyl) oxy] -6-fluoro- phenyl] propan-2-0l (can be prepared according to the procedures described in WO 2011/081174) + TX, oxatiapiproline + TX [1003318-67-9], N- [6 - [[[(1-methyltetrazole- 5-yl) -phenyl-methylene] amino] oxymethyl] -2-pyridyl] tert-butyl carbamate + TX, N- [2- (3,4-difluorophenyl) phenyl] -3- (trifluoromethyl) pyrazine-2- carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3- (difluoromethyl) -l-methyl-N - [(3R) -1,1,3-trimethylindan-4-yl] pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX , N- [2-methyl-1 - [[((4-methylbenzoyl) amino] methyl] propyl] 2,2,2-trifluoroethyl carbamate + TX, (2RS) -2- [4- (4-chlorophenoxy) - a, a, a-trifluoro-o-tolyl] -1- (1H-1,2,4-triazol-11-yl) propan-2-ol + TX, (2RS) -2- [4- (4- chlorophenoxy) -a, a, a-trifluoro-o-tolyl] -3-methyl-l- (1H-1,2,4-triazol-1-yl) butan-2-ol + TX, 27 (di-fluoromethyl) -N - [(3R) -3-ethyl-1,1, 1,1-dimethyl-indan-4-yl] pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N- [3-

ethyl-1,1-dimethyl-indan-4-yl] pyridine-3-carboxamide + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N-ethyl-N-methyl-formamidine + TX , N '- [4- (4,5-dichlorothiazol-2-yl) oxy-2,5-dimethyl-phenyl] - N-ethyl-N-methyl-formamidine (can be prepared according to the procedures described in WO 2007/031513) + TX, [2- [3- [2- [1- [2- [3,5-bis (di fluoromethyl) pyrazol-1-yl] acetyl] -4-piperidyl] thiazol-4-yl ] -4,5-dihydroisoxazol-5-yl] -3-chlorophenyl] methanesulfonate (can be prepared according to the procedures described in WO 2012/025557) + TX, N- [6 - [[(2 ) - [(I-methyltetrazol-5-yl) -phenyl-methylene] amino] oxymethyl] -2-pyridyl] carbamate but-3-inyl (can be prepared according to the procedures described in WO 2010/000841) + TX, 2 - [[3- (2-chloropheni] l) -2- (2,4-difluorophenyl) oxiran-2-yl] 1methyl] -4H-1,2,4-triazole-3-thione (can be prepared according to the procedures described in WO 2010/146031) + TX, N - [[5- [4- (2,4-dimethylphenyl) triazol-2-yl] -2-methyl-phenyl] methyl] methyl carbamate + TX, 3-chloro-6-methyl-5-pheni l-4- (2,4,6-trifluorophenyl) pyridazine (can be prepared according to the procedures described in WO 2005/121104) + TX, 2- [2-chloro-4- (4-chlorophenoxy) phenyl] - 1- (1,2,4-triazol-1-yl) propan-2-ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro-4- (2,6- difluorophenyl) -6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4- (2,6-difluorophenyl) -6-methyl-5-phenyl-pyridazine -3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774 + TX, (R) -3- (difluoromethyl) -l-methyl-N- [1,1,3-trimethylindan- 4-yl ] pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2011/162397) + TX, 3- (di-fluoromethyl) -N- (7-fluoro-1, 1,3-trimethyl-indan-4 -yl) -1- methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1- [2 - [[1- (4-chlorophenyl) pyrazole-3- yl] oxymethyl] -3-methyl-phenyl] - 4-methyl-tetrazole-5 -one (can be prepared according to the procedures described in WO 2013/162072) + TX, 1-methyl-4- [3-methyl-2 - [[2-methyl-4- (3,4,5-trimethylpyrazole -l1- yl) phenoxy] 1methyl] phenyl] tetrazol-5-one (can be prepared according to the procedures described in WO 2014/051165) + TX, (Z, 2E) -5- [1- (4-chlorophenyl ) pyrazol-3-yl] oxy-2-methoxyimino-N, 3-dimethyl-pent-3-enamide + TX, (4-phenoxyphenyl) methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX, N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methylpyrazol-4-carboxamide [1255734-28-1] (can be prepared according to procedures described in WO 2010/130767) + TX, 3- (difluoromethyl) -N - [(R) -2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl] -l -methylpyrazol-4-carboxamide [1352994-67-2] + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N- ethyl-N-methyl-formamidine + TX, N' - [4 - (4,5-dichloro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX, N '- (2,5-dimethyl-4-phenoxy- phenyl) -N-ethyl-N-methyl-formamidine + TX, N '- [4- (4,5-dic loro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX,

ho o DA o o “o

Í QRO

SN o (phenpicoxamide [517875-34-2]) + TX (as described in WO 2003/035617), 2- (difluoromethyl) -N- (1,1,3-trimethylindan-4-yl) pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N- (3-ethyl-1,1-dimethyl-indan-4-yl) pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N- (1,1-dimethyl -3- propyl-indan-4-yl) pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N- (3-isobutyl-1,1-dimethyl-indan-4-yl) pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N - [(3R) - 1,1,3-trimethylindan-4-yl) pyridine-3-carboxamide + TX, 2- (difluoromethyl) -N - [(3R) -3- ethyl-1,1-dimethyl-indan-4-yl] pyridine-3-carboxamide + TX, and 2- (difluoromethyl) -N - [(3R) - 1,1-dimethyl-3-propyl-indan-4- il] pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and / or WO 2016/139189.

[0158] 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 the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], are described therein under the entry number given in parentheses here above 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 can be accessed via the internet [A. Wood; "Compendium of Pesticide Common Names", Trademark O 1995-2004]; for example, the compound “acetoprol” is described at http://www.alanwood.net/pesticides/acetoprole.html.

[0159] Most of the active ingredients described above are referred to here above by a so-called “common name”, with the relevant “common name ISO” or another “common name” used in individual cases. If the designation is not a “common name”, the nature of the designation used instead is given in curly brackets for the particular compound; in that case the name IUPAC, the name IUPAC / Chemical Abstracts, a “chemical name”, a “traditional name”, a “compound name” or a “development code” are used or, if neither of these designations is used nor a “common name”, an “alternative name” is used. “No. CAS Registry ”means the Chemical Abstracts Registration Number.

[0160] The mixture of active ingredients of the compounds of formula (1) selected from a compound represented in Tables 1.1A to 1.8A, Tables 1.1B to 1.8B, Tables 2.1A to 2.3A, Tables 2.1B to 2.3B (below ), or in compounds

1.1 through 1.10 described in Table T1 (below) or the compounds

2.1 to 2.80 described in Table T2 (below) preferably in a mixing ratio from 100: 1 to 1: 6000, especially from 50: 1 to 1:50, more especially in a ratio from 20: 1 to 1:20, still more especially from 10: 1 to 1:10, most especially between 5: 1 and 1: 5, with special preference being given to a ratio from 2: 1 to 1: 2, and a ratio from 4: 1 to 2: 1 being equally preferred, above all in a ratio of 1: 1, or 5: 1, or 5: 2, or 5: 3, or 5: 4, or 4: 1, or 4: 2, or 4: 3, or 3: 1, or 3: 2, or 2: 1, or 1: 5, or 2: 5, or 3: 5, or 4: 5, or 1: 4, or 2: 4, or 3: 4, or 1: 3, or 2: 3, or 1: 2, or 1: 600, or 1: 300, or 1: 150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1: 6000, or 1: 3000, or 1: 1500, or 1: 350, or 2: 350, or 4: 350, or 1: 750, or 2: 750, or 4: 750. These mixing ratios are by weight.

[0161] The mixtures as described above can be used in a method for pest control which comprises the application of a composition comprising a mixture as described above in the pests or in their environment, with the exception of a method for the treatment of human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

[0162] Mixtures comprising a compound shown in Tables 1.1A through 1.8A, Tables 1.1B through

1.8B, Tables 2.1A through 2.3A, Tables 2.1B through 2.3B (below), or a compound 1.1 through 1.10 described in Table T1 (below) or a compound 2.1 through 2.80 described in Table T2 (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 isolated active ingredient components, such as a “tank mix”, and in a combined use of the isolated active ingredients when applied in a sequential manner, that is, one after another within a reasonably short period, such as a few hours or days. The order of application of the compounds represented in Tables 1.1A through 1.8A, Tables 1.1B through

1.8B, Tables 2.1A through 2.3A, Tables 2.1B through 2.3B (below), or a compound 1.1 through 1.10 described in Table T1 (below) or a compound 2.1 through 2.80 described in Table T2 (below), and do ( s) active ingredient (s) described above is not essential for the practice of the present invention.

[0163] The compositions according to the invention can also comprise additional solid or liquid auxiliaries, such as stabilizers, for example, non-epoxidized or epoxidized vegetable oils (for example, coconut oil, rapeseed oil or epoxidized soy oil) , defoamers, for example, silicone oil, preservatives, viscosity regulators, binders and / or adhesives, fertilizers or other active ingredients to obtain specific effects, for example, bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

[0164] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example, by grinding, sieving and / or compression of a solid active ingredient and in the presence of at least one auxiliary, for example, by intimate mixing and / or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of compounds (I) for the preparation of these compositions are also a subject of the invention.

[0165] Another aspect of the invention relates to the use of a compound of Formula (I) or an individual compound "preferred as defined herein, a composition comprising at least one compound of Formula (1) or at least one individual compound preferred as defined above or a fungicidal or insecticidal mixture comprising at least one compound of Formula (1) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as described above, to control or prevent 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.

[0166] 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, their propagating material, for example, seeds, crops harvested, for example, crops foodstuffs harvested, or from non-living materials, by insects or by phytopathogenic microorganisms or that cause deterioration or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of Formula (II) or a preferred individual compound as defined above as an active ingredient in plants, parts of plants or their locus, propagating material or any part of non-living materials.

[0167] Control or prevention means reduction of infestation by phytopathogenic microorganisms or that cause deterioration or organisms potentially harmful to man, especially fungal organisms, to such an extent that an improvement is demonstrated.

[0168] A preferred method to control or prevent an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects that comprises the application of a compound of Formula (I), or an agrochemical composition that contains at least one of the aforementioned compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of Formula (1) can also penetrate the plant through the roots via the soil (systemic action), by soaking the plant's locus with a liquid formulation, or by applying the compounds in solid form to the soil, by example, in granular form (application to the soil). In irrigated rice crops, such granules can be applied to the irrigated rice field. The compounds of Formula (1) 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.

[0169] A formulation, for example, a composition containing the compound of Formula (1) and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of Formula (I), can be prepared in a known manner, typically by intimate mixing and / or grinding the compound with diluents, for example, solvents, solid carriers and, optionally, surfactant compounds (surfactants).

[0170] Advantageous application rates are normally 5 g / kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg of a.i./ha, more preferably from 20 g to 600 g of a.i./ha. When used as a seed drenching agent, convenient dosages are 10 mg to 1 gq of active substance per kg of seeds.

[0171] 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 .

[0172] Suitably, a composition comprising a compound of Formula (1) according to the present invention is applied preventively, meaning before disease development, or curatively, meaning after disease development.

[0173] The compositions of the invention can be employed in any conventional form, for example, in the form of a double pack, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a suitable concentrate to flow for seed treatment (FS), a seed treatment solution (LS), a water dispersible powder for seed treatment (WS), a suspension for seed treatment capsules (CF), a gel for treatment of seeds seeds (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG) , an emulsion, water in oil (EO), an emulsion, oil in water (EW), a microemulsion (ME), an oil dispersion (OD), an oil miscible fluid (OF), an oil miscible liquid ( OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0174] Such compositions can be produced in a conventional manner, for example, by mixing the active ingredients with appropriate formulation aggregates (diluents, solvents, fillers and, optionally, other formulation ingredients such as surfactants, biocides, antifreeze, adhesives , thickeners and compounds that provide adjuvant effects). Conventional slow release formulations can also be employed when long-term efficacy is desired. Particularly, Formulations to be applied to spray forms, such as water-dispersible concentrates (eg EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants 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.

[0175] A seed treatment formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in the form of a formulation suitable for seed treatment, for example, as an aqueous suspension or in a powder form dry with good adhesion to seeds. Such seed treatment formulations are known in the art. Seed treatment formulations can contain the active ingredients alone or the combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[0176] In general, formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of agriculturally acceptable surfactant and 10 to 99.99% of inert solid or liquid formulation agents and adjuvant (s) ), wherein the active agent consists of at least the compound of Formula (1) 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 and 70% by weight, of active agent. Forms of application of the formulation may contain, for example, from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of the active agent. Although commercial products are preferably formulated as concentrates, the end user will normally use diluted formulations.

2,2,2- 2,2,2- 1A.007 1A.045 trifluoroethoxy trifluoroethanamino 1A.009 benzizóxt - fiacoms prop-2-in-l1-amino cyclopropylmetanami 1A.010 phenoxy 1A.048 in N-methylaceto-1A. 012 prop-2-enyloxy 1A.050 hydrazide (2,2-1A.013 2,2-dimethylpropoxy 1A.051 dichlorocyclopropyl methanamino N-methylpropan-2- 1A.014 cyclohexoxy 1A.052 amino tetrahydrofuran-1A. 016 1A.054 methanamino 3-yloxy 1A.019 butaninizns - fine prop-2-en-l1-amino 1A.021 xetananizoxes - fiascoous 2-propanylamino 1,1-dimethyl- 1A.022 2-methoxyethoxy 1A.060 hydrazine

O-ethyl-1A.023 1A.061 N-ethylethylamino hydroxylamino 2-methylpropan-1-1- 1A.025 2-propoxy 1A.063 amino 2-methylpropan-2- 1A.026 ethoxy 1A.064 amino N-methylformyl-1A. 029 1A.067 aniline hydrazide 2,2-dimethylpropan- 1A.030 1A.068 phenylmethanamino l1-amino O- (prop-2- 1A.031 1A.069 cyclopentanamino enyl) hydroxylamino IN 1- 1A.032 (cyclopropylmethyl) 1A. 070 cyclopropylethanamin propan-l1-amino o- 2- 1A.033 (cyclopropylmethyl) (1A.071 [amino (methyl) amino] hydroxylamino ethyl acetate N-5- 1A.034 azonospiro [2.4] h / 1A.072 N -isoxazolidine eptane

N-cyclopropyl-N-IN 1A.035 (2,2- 1A.073 ethylcyclopropanamin difluoroethyl) amino fame Ei, O- (prop-2- 1A.036 (cyclopropylmethyl) [1A.074 inyl) hydroxylamino hydroxylamino N - o- (2,2,2- 1A.037 methylcyclopropan- | 1A.075 trifluoroethyl) hydro amino xylamino O- (2,2- 1A.038 difluoroethyl) hydro xylamino

[0180] Table 1.2A: This table reveals 75 specific compounds of the formula (T-1A) in which R ?, Rà, Ri, Rº, and Rº are hydrogen, R! is fluorine, and R “Nu is as defined above in Table 1A.

[0181] Table 1.3A: This table reveals 75 specific compounds of the formula (T-1A) where R !, R ?, Ri, Rº, and Ré are hydrogen, Rº is fluorine, and R “Nu is as defined above in Table 1A.

[0182] Table 1.4A: This table reveals 75 specific compounds of the formula (T-1A) where Rº, Ré, Rº, and Rº are hydrogen, R! and Rº are fluorine, and Rº-Nu is as defined above in Table 1A.

[0183] Table 1.5A: This table reveals 75 specific compounds of the formula (T-1A) where Rà, Ri, Rº, and Rº are hydrogen, R 'and R? º are fluorine, and Rº-Nu is as defined above in Table 1A.

Table 1B Compound Compound Rº-Nu Rº-Nu no. at the. 1B.001 ficiopentéxs - fa. 039 piperidin-1-amino 1B.003 cyclopropylmethoxy 1B.041 O-methyl- 1B.004 3-fluoropropoxy 1B.042 hydroxylamino 1B.006 pentéxi -> became N-methylethylamino 2,2,27 1B.007 2,2,2 -trifluoroethoxy 18,045 trifluoroethanamino 1B.009 pensizóa - be. 047 prop-2-in-1-amino cyclopropylmethanamin 1B.010 phenoxy 1B.048 o N-methylaceto- 1B.012 prop-2-enyloxy 1B.050 hydrazide (2.27 1B.013 2,2-dimethylpropoxy 1B.051 dichlorocyclopropyl) m ethanamino N-methylpropan-2- 1B.014 cyclohexoxy 1B.052 amino tetrahydrofuran-3- 1B.016 1B.054 methanamino yloxy 1B.019 pucoininens - - fincoso prop-2-en-l-amino 1,1-dimethyl- 1B.022 2-methoxyethoxy 1B.060 hydrazine 1B.023 O-ethylhydroxylamino 1B.061 N-ethylethylamino 2-methylpropan-1-1- 1B.025 2-propoxy 1B.063 amino 2-methylpropan- 2- 1B.026 ethoxy 1B.064 amino N-methylformyl- 1B.029 1B.067 aniline hydrazide 2,2-dimethylpropan-1- 1B.030 1B.068 phenylmethanamino amino

O- (prop-2- 1B.031 1B.069 cyclopentanamino enyl) hydroxylamino No. cyclopropyl-1- 1B.032 (cyclopropylmethyl) pr 18.070 ethanamino opan-l1-amino [9 2- 1B.033 (cyclopropylmethyl) hi | 1B. 071 [amino (methyl) amino] to droxylamino ethyl ketate N-5- 1B.034 azonospiro [2.4] hep | 1B.072 N-isoxazolidine tano N-cyclopropyl-N-IN = 1B.035 (2.2-1B .073 ethylcyclopropanamino difluoroethyl) amino o- O- (prop-2- 1B.036 (cyclopropylmethyl) hi | 1B.074 inyl) hydroxylamino droxylamino IN 0- (2,2,2- 1B.037 methylcyclopropanamin (18,075 trifluoroethyl) hydrox o ilamino o- (2,2- 1B.038 difluoroethyl) hydroxy lamino

[0189] Table 1.2B: This table reveals 75 specific compounds of the formula (T-1B) in which R? º, Rà, Ri, Ró, and R6 are hydrogen, R! is fluorine, and R “Nu is as defined above in Table 1B.

[0190] Table 1.3B: This table reveals 75 specific compounds of the formula (T-1B) in which, R !, R? À, Rº, Rº, and Rº are hydrogen, R? º is fluorine, and R-Nu is as defined above in Table 1B.

[0191] Table 1.4B: This table reveals 75 specific compounds of the formula (T-1B) in which Rº, Ri, Ri, and Rº are hydrogen, R! and Rº are fluorine, and Rº-Nu is as defined above in Table 1B.

[0192] Table 1.5B: This table reveals 75 specific compounds of the formula (T-1B) where Rà, Ri, Rº, and Rº are hydrogen, R 'and R? º are fluorine, and Rº-Nu is as defined above in Table 1B.

[0193] Table 1.6B: This table reveals 75 specific compounds of the formula (T-1B) where R !, R ?, R? º Ré, and Rº are hydrogen, Rº is methyl, and Rº-Nu is as defined above in Table 1B.

[0194] Table 1.7B: This table reveals 75 specific compounds of the formula (T-1B) where R !, Rºà, Rº and Rº are hydrogen, Rº and Rº are fluorine, and Rº-Nu is as defined above in Table 1B .

[0195] Table 1.8B: This table reveals 75 specific compounds of the formula (T-1B) in which Rà, Rà, Rº and Rº are hydrogen, R! and R “are fluorine, and Rº-Nu is as defined above in Table 1B.

[0196] Table 2.1A: This table reveals 6 specific compounds of the formula (T-2A):

EXAMPLES

[0204] The following Examples serve to illustrate the invention.

[0205] The compounds of the invention can be distinguished from known compounds by virtue of the greater effectiveness at low application rates, which can be verified by the skilled person using the experimental procedures outlined in the Examples, using lower application rates, if necessary , for example, 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0206] The compounds of Formula (1) can have any number of benefits including, inter alia, advantageous levels of biological activity to protect plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous activity spectrum, an increased safety profile (including improved crop tolerance), improved physico-chemical properties or increased biodegradability).

[0207] Throughout this description, temperatures are presented in degrees Celsius (ºC) and "mp." means melting point. LC / MS stands for Liquid Chromatography - Mass Spectrometry and the description of the apparatus and method (Methods A, BC and D) is as follows: The description of the LC / MS device and method A is: Waters Method SQ 2 detector ionization: Electrospray Polarity: positive and negative ions

Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (ºC) 150, Desolvation Temperature (ºC) 350, Gas Flow in the Cone (L / h) O, Desolvation Gas Flow (L / h) 650 Mass range: 100 to 900 Da DAD (nm) wavelength range: 210 to 500 Waters UPLC ACQUITY method with the following HPLC gradient conditions: ( Solvent A: Water / Methanol 20: 1 + 0.05% formic acid and Solvent B: Acetonitrile + 0.05% formic acid Time (minutes) A (3%) B (%) Flow rate (mL / min )

o 100 [o 0.85

1.2 or 100 0.85

1.5 o 100 0.85 Column type: UPLC ACQUITY HSS T3 by Waters; Column length: 30 mm; Column internal diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 “C.

The description of the LC / MS apparatus 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 (ºC) 150, Desolvation Temperature (ºC) 400, Cone Gas Flow (L / h) 60, Desolvation Gas Flow (L / h) 700 Mass Range: 140 to 800 Da Range Wavelengths of DAD (nm): 210 to 400

Waters UPLC ACQUITY method with the following HPLC gradient conditions (Solvent A: Water / Methanol 9: 1 + 0.1% formic acid and Solvent B: Acetonitrile + 0.1% formic acid Time (minutes A (3 %) B (3%) Flow rate (mML / min)

o 100 [9 0.75

2.5 or 100 0.75

2.8 or 100 0.75

3.0 100 [o 0.75 Column type: UPLC ACQUITY HSS T3 from Waters; Column length: 30 mm; Column internal diameter: 2.1 mm; Particle Size: 1.8 microns; Temperature: 60 “C.

The description of the LC / MS apparatus and method C is: Waters SQ 2 detector Ionization method: UPLC electrospray Class H ACQUITY, Waters Mass Spectrometer Polarity: Positive and Negative Polarity Switch Scanning type MS1 Capillary Scan (KV ) 3.00, Cone (V) 40.00, Desolvation Temperature (ºC) 500, Cone Gas Flow (L / h) 50, Desolvation Gas Flow (L / h) 1000 Mass range: O to 2000 From DAD wavelength range (nm): 200 to 350 Waters UPLC ACQUITY method with the following HPLC gradient conditions (Solvent A: Water + 0.1% formic acid and Solvent B: Acetonitrile)

Time (minutes) A (%) B (%) Flow rate (mML / min) [70 30 0.5 0.05 70 30 0.5 0.8 5 95 0.5 1.8 5 95 0.5 2.45 70 30 0.5 2.50 70 30 0.5 Column type: UPLC BEH C18 ACQUITY by Waters; Column length: 50 mm; Column internal diameter: 2.1 mm; Particle Size: 1.7 microns; Temperature: 35 “C.

The description of the LC / MS apparatus and method D is: Instrumentation: - Mass Spectrometer: Agilent 6410 HPLC Triple Quadripole Mass Spectrometer: Agilent 1200 Series HPLC with Quaternary Gradient Optimized Mass Parameter: - Ionization method: Electrospray ( ESI) Polarity: Positive and Negative Polarity Sweep Sweep Type: Capillary MS2 Sweep (KV): 4.00 Fragmenter (V): 100.00 Gas Temperature (* C): 350 Gas Flow (L / min): 11 Nebulizer gas (psi): 45 Mass range: 110 to 1000 Da

Optimized Chromatographic Parameter: - Gradient conditions with Solvent A: Water with 0.1% formic acid: Acetonitrile:: 95: 5 v / ve Solvent B: Acetonitrile with 0.1% formic acid Time (minutes) A (%) B (8%) Flow rate (mL / min) [9 90 10 1.8 0.9 o 100 1.8 1.8 [o 100 1.8 2.2 90 10 1.8 2.5 90 10 1 , 8 PDA wavelength range: 210 to 400 nm; Column: KINETEX EVO C18; Column length: 50 mm; Column internal diameter: 4.6 mm; Particle Size: 2.6 microns; Temperature: 40 ҼC.

[0208] When necessary, enantiomerically pure final compounds can be obtained from racemic materials as appropriate through standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, for example, using starting chiral.

Formulation Examples Wettable powders a) b) c) Active ingredient [25% compound 50% 758% Formula (1)] sodium lignosulfonate 55% 5% - sodium lauryl sulfate 38% - 5% diisobutyl naphthalenesulfonate - 6% 108% sodium polyethylene glycol phenolic ether - 2% - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 108% Kaolin 62% 278% -

[0209] The active ingredient is extensively mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, giving rise to wettable powders that can be diluted with water to give suspensions with the desired concentration.

Powder for seed treatment aa) b) Cc) dry Active ingredient [25% compound 50% 758% Formula (1)] light mineral oil 58% 5% 5% highly dispersed silicic acid 5% 58% - Kaolin 65% 40 3% - Talc - - 20%

[0210] The active ingredient is extensively mixed with the adjuvants, and the mixture is extensively crushed in a suitable mill, giving rise to powders that can be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of Formula 10% (1)) polyethylene glycol 3 8% octylphenolic ether (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 38% castor oil polyglycolic ether (35 4% mol% oxide ethylene)

Cyclohexanone 30% mixture of xylenes 50 8%

[0211] Emulsions of any required dilution, which can be used to protect plants, can be obtained from this concentrate by dilution with water.

Dusts a) b) c) Active ingredient [compound of 5 8% [0 4% Formula (1)] Talc 95% - - Kaolin - 94% - mineral filler - - 9%

[0212] Ready-to-use dust is obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed films.

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

[0213] The active ingredient is mixed and crushed with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in a draft.

Coated granules Active ingredient [compound of Formula 8 (1)] AND polyethylene glycol (p. Mol. 3 200)% Kaolin 89 &%

[0214] The finely ground active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. In this way, coated, non-dusty granules are obtained.

Suspension concentrate Active ingredient [compound of Formula (1)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 6 & mol% ethylene oxide) Sodium lignosulfonate 10% Carboxymethyl cellulose 138 Silicone oil (in the form of an emulsion a 1% 75% in water) Water 32%

[0215] The finely crushed active ingredient is intimately mixed with the adjuvants, giving rise to a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, spilling or immersion.

Flowable concentrate for seed treatment Active ingredient [compound of Formula (1)] 40% propylene glycol 55% butanol PO / EO 2% copolymer

triestyrenophenol with 10-20 moles EO 28% 1,2-benzisothiazolin-3-one (in the form of a 0.5 8% 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 8

[0216] The finely ground active ingredient is intimately mixed with the adjuvants, giving rise to a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, spilling or immersion. Suspension for Slow Release Capsules

[0217] 28 parts of a combination of the compound of Formula I are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / polymethylene polyphenylisocyanate mixture (8: 1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is reached. To this emulsion is added a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water. The mixture is stirred until the polymerization reaction is completed.

[0218] The suspension for capsules obtained is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The Suspension Formulation for capsules contains 28% of the active ingredients. The average diameter of the capsules is 8-15 microns.

[0219] The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for this purpose.

Abbreviation list: AIBN = azobisisobutyronitrile BOP-Cl = phosphoric acid bis (2-oxo-oxazolidide) chloride DMF = dimethylformamide DIBAL-H = diisobutylaluminum hydride DIPEA = N, N-diisopropylethylamine EtOAcC = ethyl acetate HCl = hydrochloric acid mp = melting point ºc = degrees Celsius MeoOH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide min = minutes TA = room temperature h = hour (s) TFAA = trifluoroacetic acid anhydride THF = tetra -hydrofuran tr = retention time (in minutes LC / MS = Liquid Chromatography Mass Spectrometry (description of the apparatus and methods used for LC / MS analysis is presented above)

followed by 1H-imidazole-4-carbaldehyde (0.1 g, 11 mmol) and the system was stirred at room temperature for 3 hours. Then, the reactor was diluted with water (10 ml), extracted with ethyl acetate and the total combined organic layer was washed with brine solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by column chromatography (eluent gradient dichloromethane: methanol 95: 5) and 0.075 gq of 3 - [[4- [5- (trifluoromethyl) -1,2,4- oxadiazole-3- were isolated yl] phenyl] methyl] imidazole-4-carbaldehyde. LC / MS (Method C) retention time = 1.41 minutes, (M + H) not detected.

[0235] 'H NMR (400 MHz, CDCl3) 3 ppm: 9.90 (s, 1H), 8.24 (m, 2H), 7.70 (m, 2H), 7.29 (m, 2H) , 5.60 (m, 2H)

[0236] 1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-4-carbaldehyde was isolated as a by-product (0.068 g) LC / MS (Method C) retention time = 1.37 minutes, (M + H) not detected.

[0237]! H NMR (400 MHz, CDCl3) 5 ppm: 9.90 (s, 1H), 8.25 (m, 2H), 7.75 (m, 2H), 7.29 (m, 2H) , 5.60 (m, 2H) Step 5: Preparation of N- (2,2-difluoroethoxy) -1-1- [1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazole-3- il] phenyl] methyl] imidazol-4-yl] metanimine

[0238] To a solution of 1 - [[4- [5- (trifluoromethyl) - 1,2,4-0oxadiazol-3-yl] phenyl] methyl] imidazole-4-carbaldehyde (0.1 g, 0.3 mmol) in ethanol (6 mL) O- (2,2-difluoroethyl) hydroxylamine hydrochloride (0.1 g, 0.9 mmol) and sodium acetate were added. The reaction mixture was stirred overnight. The volatiles were removed under reduced pressure, 20

[0245] To a suspension of methyl 1 - [[4- [5- (trifluoromethyl) - 1,2,4-0oxadiazol-3-yl] phenyl] methyl] imidazole-4-carboxylate (0.8 g, 2 , 27 mmol) in methanol (32 mL) cooled to 0 ° C via an ice bath, barium hydroxide octahydrate (1.43 g, 6.8 mmol) in water (26 mL) was added. The reaction mixture was stirred at room temperature for 12 hours. The reaction was diluted with water, the volatiles were removed under reduced pressure, and extracted with ethyl acetate. The aqueous layer was acidified to pH = 2 with 1M aqueous HCl extracted with EtOAc and the total combined organic layer was washed with brine, dried over Naz2SO4s, filtered and concentrated under reduced pressure, giving 0.35 g of the title compound. in the form of a white powder. LC / MS (Method A) retention time = 0.37 minutes, (M + H) not detected.

[0246] 'H NMR (400 MHz, DMSO-ds) 5 ppm: 8.04 (m, 3H) 7.94 (m, 1H), 7.48 (m, 2H), 5.37 (s, 2H ) Step 3: Preparation of propyl 1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-4-carboxylate

[0247] To 1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-4-carboxylic acid (100 mg, 0.29 mmol) dissolved in propan-1-ol (6 ml) was added thionyl chloride (0.011 ml, 0.15 mmol) at room temperature. The reaction mixture was stirred at 70 ° C for 12 hours. Then, the reactor was diluted with ice water (10 mL), extracted with ethyl acetate, brine solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure and gave 0.075 g of the title compound as a solid. light brown. mp: 248 - 250 "C.

Table T1: Melting point data (mp) and / or retention times (trg) for compounds 1.1 through 1.10 according to Formula (1): Method load Name of mass pf Input Compound structure (min) | [M + H] (ºC)

LCMS + N-methoxy- 1- [1 - [[4- [5-7 (trifluor

Fomethyl) - '

N FF 1,2,4-

1.1 oxadiazole S 1.39 352 D À 7 —3- N yl) phenyl] NA methyl] imidazol-4-yl] methanine N-methoxy- [32 - F 1- [3 - [[4 x (

N [5- t Ff 91 -

1.2 Ox trifluor 93 (ts omethyl) - N 1,2,4-

Load of Method Name of mass pf Input Compound structure (min) [M + H] (o)

R LCMS oxadiazol -3-yl] phenyl] methyl] imidazol-4-yl] methanamine N-ethoxy- 1- [1 - [[4- [5- (trifluor; omethyl) - SA 1,2,4-

1.3 oxadiazole (> 1.35 366 D —3- H illfenia] NQ methyl] imidazol-4-yl] methanine

Load of Method Name of mass pf Input Compound structure (min) [M + H] (o)

LCMS + N- (2,2-difluoroe toxi) -l- [1 - [[4- [5- NO +; A (trifluor N EFE omethyl) - 70 -

1.4 1,2,4- (> N 72 oxadiazole

F so RA

Phyl] phenyl] methyl] imidazol-4-yl]) methanamine N-ethoxy- 1- [3 - [[4- nO E [5- 1 PA, the

1.5 (trifluor DX 97 omethyl) - N 1,2,4- oxadiazole

Load of Method Name of mass pf Input Compound structure (min) [M + H] (o)

LCMS + -3- yl] phenyl] methyl] imidazole-4-illmethanine N- (2,2-difluoroe toxi) -l- [3 - [[4- [5- (trifluoromethyl) - F PA aa CG 6s -

1.6 1,2,4- O. SS 67 oxadiazole N —3- yl] phenyl] methyl] imidazole-4-yl] methanamine

Load of Method Name of mass pf Input Compound structure (min) [M + H] (o)

LCMS + 1 - [[4- [5- (trifluoromethyl) - 1,2,4- neo E + oxadiazole 4? & -3- 248 -

1.9 il] phenyl] PR 250 methyl] imia a propyl dazol-4-carboxylate N-cyclopropyl-1 - [[4- [5- SO, (trifluor O o

1.10 <q o me 0.93 378 A omethyl) - F

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

Load of Method Name of mass pf Input Compound structure (min) [M + H] (o)

LCMS + methyl] imidazole-4-carboxami from Table T2: Melting point data (mp) and / or retention times (trg) for compounds 2.1 to 2.80 according to Formula (1): tr Load, LCMS pf Input Name of (min) da | Method (ºC) Structure compound mass [M + H] o

2.1 N-methyl- 2EQ, 1.22 352.06 B 157, H í bl 1 - [[4- [5- No F 5 - (trifluor 160, omethyl) - 8 1,2,4- oxadiazole -3- yl] phenyl) methyl] imidazole-4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

H

2.2 N-methyl- Se 1.05 352.06 B 3 - [[4- [5- EO (trifluor Otomethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-4- carboxami da

2.3 DE No. 165 cycloprop - yl-3 - [[4- O 170 [5- b (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.4 3 - [[4- [5- A E (trifluor A 93 omethyl) - e 1,2,4- À + oxadiazol-3-yl] phenyl] methyl] imidazole-4-ethyl carboxylate

2.5 N-ethoxy-Sn 157 3 - [[4- [5- Tea - (trifluor o 159 omethyl) - AT 1,2,4- oxadiazol -3-yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.6 N-ethoxy- ON 156 1 - [[4- [5- IS F 2 (trifluor 160 omethyl) - n A 1,2,4- o N oxadiazol -3-yl] phenyl] methyl] imidazole-4- carboxami da

2.7 N- (1- RA FF 1,327. 420 D cycloprop Tea iletil) - N-methyl-EA, 3 - [[4- [5- (trifluor omethyl) - 1,2,4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed by mass [M + H] oxadiazol-3-yl) phenyl] methyl] imidazole-4-carboxami da

2.8 1 - [[4- [5- A 150 (trifluor IS ”a - omethyl) - P 154 1,2,4- PR, oxadiazol-3-yl] phenyl] methyl] imidazole-4-ethyl carboxylate

F

2.9 1 - [[4- [5- SS 112 (trifluoromethyl) - 5 114 1,2,4-? oxadiazole tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed of methyl [M + H] -3- yl) phenyl] methyl] imidazole-2-methyl carboxylate

2.10 1 - [[4- [5- Y x 74 - (trifluor vor 76 omethyl) - NA 1,2,4- CX oeN oxadiazol -3-yl] phenyl] methyl] imidazole-2-ethyl carboxylate

2.11 SR No. 128 cycloprop Tea - il-1 - [[4- PP 131 and QA (trifluor tr Load, LCMS pf Input Name of (min) da Method | (ºC) Structure compound mass [M + H] omethyl) - 1 , 2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-2-carboxamide

2.12 N-ethoxy- 5 »VE 129 1 - [[4- [5- Tea - (trifluor o 132 omethyl) - Qro 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole-2-carboxami da tr Load, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2.13 N- (1- WS 1.52) 420 D cycloprop Tea ilethyl) - N-methyl-AA, 1 - [[4- [5- (trifluoromethyl) - 1,2,4- oxadiazol -3- yl ] phenyl] methyl] imi dazol-2-carboxami da

2.14 - 1 - [[4- [5- A, 160 (trifluor o - omethyl) - E 162 1,2,4- SO> oxadiazol-3-yl] phenyl) methyl] imidazole-4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed by mass [M + H] carboxylate of (3-cyclopropylisoxazo 1-5-yl) methyl

2.15. 1 - [[4- [5- to 111 (trifluorine FS - omethyl) - SL 113 1,2,4- / ADS oxadiazole S -3-yl] phenyl] methyl] imidazole-4-carboxyl of 2.2 , 2- ethyl trifluoro

2.16 N- (2,2- SIA 150 difluoroe - toxi) -1- AE 152 [[4- [5-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] (trifluoromethyl) - 1,2,4- oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxamide

2.17 N-sec- C 1.51 394.10 B butyl-1- H o [[4- [5- DS (trifluoromethyl) - F OS 1,2,4- PA oxadiazol -3-yl] phenyl) methyl ] imi dazol-4-carboxami da tr Load, LCMS pf Entry Name of (min) da Method | (ºC) Composite structure mass [M + H]

2.18 - N- (2.2- NX 1.63 408.12 B dimethylpr H opyl) -1- X [[4- [5- (trifluor & OS omethyl) - PAL 1,2,4- oxadiazole -3- il] phenyl] methyl] imi dazol-4-carboxami da

2.19 —N-) - 1.42 380.08 B isopropyl s o 1 - [[4- 1 [5-. F (PAL trifluor omethyl) - 1,2,4-oxadiazol -3-yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.20 - N-methoxy- and 1.17 382.05 B N-methyl- "o 1 - [[4- [5- [O (trifluoromethyl) - AX 1,2,4-oxadiazol -3-yl] phenyl ] methyl] imi dazol-4-carboxami da

2.21 N, No. —N (1.18 366.05 B dimethyl- SD 1 - [[4- [5- (trifluor & OS omethyl) - PA 1,2,4- oxadiazole tr Load, LCMS pf Entry Name of ( min) da Method | (ºC) Structure compound mass [M + H] -3-yl) phenyl] methyl] imidazole-4-carboxami da

2.22 N-cyclo-OQ, 1.64 420.13 B hexyl-1- “o L [[4- [5- OS: (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl ] imi dazol-4-carboxami da

2.23 N-ethyl-l1-) 1.31 366.06 B [[4- [5- 'o (trifluor 1d omethyl) - OS

F 1,2,4- PAL tr Load, LCMS pf Input Name (min) of Method | (ºC) Structure composed by mass [M + H] oxadiazol-3-yl) phenyl] methyl] imidazole-4-carboxami da

2.24 N-allyl-1- $ 1.38 378.07 B [[4- [5- HN (trifluor A º omethyl) - ú 1,2,4- F-oxadiazole PAL -3-yl] phenyl] methyl] imi dazol-4- carboxami da tr Load, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2.25 N- “% 1.52 394.10 B isobutyl- o 1 - [[4- [5- SD (trifluoromethyl) - 5 OS 1,2,4- PAD oxadiazol -3-yl] phenyl] methyl] imi dazol-4-carboxami da

2.26 —N, N- Lt 1.41 394.13 B diethyl-l1- o [[4- [5- CP (trifluor

Fomethyl) - PAL 1,2,4-oxadiazol-3-yl] phenyl) methyl] imidazole-4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

2.27 N-phenyl- A, 1.63 414.09 B 1 - [[4- [5- “o L (trifluor OS" omethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imi dazol-4-carboxami da

2.28 N-benzyl- 1.57 428.08 B 1 - [[4- [5- A (trifluor H or omethyl) - DS 1,2,4- oxadiazole -3-

RD il) phenyl] É E methyl] imi Ff dazol-4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

2.29 N- 1.47 392.09 B cyclobuti 1-1 - [[4- ss [5- OS (trifluor FS 1 omethyl) - PA 1,2,4-oxadiazol -3-yl] phenyl] methyl] imi dazol-4-carboxami da

2.30 N-propyl- $ 1.42 380.09 B 1 - [[4- [5- HN o (trifluor «DN omethyl) - 1,2,4- F-oxadiazole PAL -3- yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.31 - N-methoxy 1,21 368,06 B 1 - [[4- [5- o (trifluor 1) omethyl) - OS

F 1,2,4- PAL oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxamide

2.32 N- o 1.54 406.11 B cyclopent HN il-1 - [[4- o [5- OS (trifluor s5 2 omethyl) - PA 1,2,4- oxadiazole tr Load, LCMS pf Entry Name of ( min) of Method | (ºC) Structure compound mass [M + H] -3-yl) phenyl] methyl] imidazole-4-carboxamide

2.33 morpholino Ff 1.25 408.26 B nie IS [5- (trifluoromethyl) - N 1,2,4- ”oxadiazole O -3- yl] phenyl) methyl] imidazole-4-ill] methane in tr Load, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2.34 N- (2- Co 1,47 418,07 B furylmeti & 1) -1 - [[4- o (5th IF (trifluoromethyl) - A 1,2,4-oxadiazol -3- yl] phenyl] methyl ] imi dazol-4-carboxami da

2.35 - N-tert-XY 1.56 394.10 B butyl-l1- ace o [[4- [5- o (trifluor O

Fomethyl) - A 1,2,4-oxadiazol-3-yl] phenyl] methyl] imi Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] dazol-4-carboxami da

2.36 N-prop-2- Y 1.34 376.07 B inyl-1- H [14- [5- th º is (trifluoromethyl) - F OS 1,2,4- PAL oxadiazol -3-yl] phenyl ] methyl] imi dazol-4-carboxami da

2.37 - N-ethyl-N-? 1.29 380.09 B methyl-l1- 7 o [[4- [5- CP (trifluor

À F ometil) - PAL 1,2,4- oxadiazole -3-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed of mass [M + H] yl] phenyl) methyl] imidazole-4-carboxami da

2.38 - N-sec- CSS 1.76 394.41 B butyl-l- O [[4- [5- PAS (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole -2- carboxami

NH

2.39 N- (2.2- EA 1.88 408.42 B dimethylpr, OS opi1) -1- PA [[4- [5- (trifluoromethyl) -

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-2-carboxami da

2.40 No. a te 1.66 380.06 B isopropyl Pa -1 - [[4- PAT [5- (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole-2- carboxami da tr Load, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2.41 - Nometoxi- Dog 1.37 382.05 B o N-methyl-OS 1 - [[4- [5- PAT (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imi dazol-2- carboxami da

2.42 NNW NO 1.33 366.07 E dimethyl-OS 9 1 - [[4- (5-PAX (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole-2-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

2.43 - N-methyl- PC 1.43 352.08 B 1 - [[4- [5- O

F (PAL trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-2-carboxamide

2.44 N-cyclo-O. 1.91 420.43 B hexyl-1-NH [[14- [5-es (trifluoromethyl) - 1,2,4-oxadiazole N À -3- A yl] phenyl] methyl ] imi tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] dazol-2-carboxami da

2.45 N-ethyl-1-So 1.54 366.06 B [14- [5-OS (trifluor AX omethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-2-carboxami gives

2.46 - N-allyl-1-GE 1.61 378.07 B [[4- [5- r OS (PAL trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imit Load , LCMS pf Entry Method (min) name | (ºC) Structure compound mass [M + H] dazol-2-carboxami da

2.47 SO # 1.77 394.11 B isobutyl-, FA 1- (14-152 PA (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-2-carboxamide

2.48 —N, N- A was 1.55 394.10 B diethyl-1-TOA

F [[4- [5- AX (trifluoromethyl) - 1,2,4- oxadiazole -3-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed of mass [M + H] yl] phenyl) methyl] imidazole-2-carboxami da

2.49 N-phenyl- O. 1.87 414.09 B 1 - [[4- [5- NH (trifluor A D omethyl) - 1,2,4- oxadiazole

N -3- N U

Fyl] phenyl] F methyl] imidazole-2-carboxamide

2.50 N-benzyl- A 1.78 428.10 B 1 - [[4- [5- HO (trifluorine omethyl) - "” EN, 1,2,4->; FTF oxadiazole -3-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed of mass [M + H] yl] phenyl) methyl] imidazole-2-carboxami da

2.51 N- GS o 1.72 392.10 B cyclobutyl FA Lina PAL [5- (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl) methyl] imidazole-2-carboxamide

2.52 N-propyl- GE 1.66 380.10 B 1 - [[4- [5- r OS (trifluor FAN omethyl) - 1,2,4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed by mass [M + H] oxadiazol-3-yl) phenyl] methyl] imidazole-2-carboxami da

2.53 N-methoxy 1.39 368.04 B 1 - [[4- [5- OS (trifluor AX omethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-2- carboxami da

N H

2.54 No. o 1.80 406.27 B cyclopent r i1-1 - [[4- PAL [5- (trifluor tr Load, LCMS pf Input Name of (min) da Method | (ºC) Structure compound mass [M + H ] omethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-2-carboxamide

2.55 morpholino FF 1.36 408.06 B - [1 - [[4- e.

N [5- = (trifluor * omethyl) - the 1,2,4-oxadiazol-3-yl] phenyl) methyl] imidazol-2-yl] methane in the load, LCMS pf Entry Name of (min) da Method | (ºC) Composite structure mass [M + H]

2.56 N- (2- EO 1.68 418.06 B furylmeti: OS 1) -1-114- PA [5- (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imi dazol-2- carboxami da

H

2.57 - N-tert- x 1.82 394.09 B butyl-1- O [[4- [5- AX (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] im Load, LCMS pf Input Name (min) of Method | (ºC) Structure compound mass [M + H] dazol-2-carboxami da

2.58 - N-prop-2 CLA 1.54 376.03 B inyl-1-, O (14ets5o PA (trifluoromethyl) - 1,2,4-oxadiazol —3-yl] phenyl] methyl] imidazole-2 - carboxami da

2.59 - N-ethyl-N- AX 1.43 380.07 B methyl-1- FA [[4- [5- AT (trifluoromethyl) - 1,2,4- oxadiazole —3-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed of mass [M + H] yl] phenyl) methyl] imidazole-2-carboxami da

2.60 N-sec- O 1.33 394.29 B butyl-3-Aa [[4- [5-PA (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole- 4- carboxami of

2.61 N- (2.2- 4 EX 1.46 408.51 B dimethylpr, A opi1) -3- PA [[4- [5- (trifluoromethyl) -

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-4-carboxami da

2.62 N- ES te 1.23 380.07 B isopropyl O -3 - [[4- PAT [5- (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole-4 - carboxami da tr Cargo, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2.63 - Nometoxi- ACTION 1.21 382.06 B N-methyl-OS '3 - [[4- [5- PAT (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imi dazol-4-carboxami da

2.64 —N, N- UNA 1.01 366.05 B dimethyl- A 3 - [[4- [5- AT (trifluoromethyl) - 1,2,4- oxadiazol -3-yl] phenyl) methyl] imidazole -4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

2.65 N-cyclo-O. 1.47 420.12 B hexyl-3-NH [[4- [5- dO (trifluoromethyl) - 1,2,4-oxadiazole N À -3- and yl] phenyl] methyl ] imi dazol-4-carboxami da

2.66 - N-ethyl-3- How 1.14 366.06 B Manisso OS (trifluor PAL omethyl) - 1,2,4- oxadiazol-3-yl] phenyl] methyl] imi Load, LCMS pf Entry Name of ( min) of Method | (ºC) Structure compound mass [M + H] dazol-4-carboxami da

2.67 N-allyl-3-QDO 1.22 378.06 B [[4- [5- r OS (PAN trifluoromethyl) - 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazole-4 - carboxami from "

2.68 —N- Do 1.35 394.09 B isobutyl- OS 3 - [[4- [5- AX (trifluoromethyl) - 1,2,4- oxadiazol -3-yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.69 N, N- Pa Co 1.22 394.09 B diethyl-3 Pa

F [[4- [5- PAL (trifluoromethyl) - 1,2,4- oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxami da tr Load, LCMS pf Entry Name of (min) da Method | (ºC) Composite structure mass [M + H]

2.70 N-phenyl- O. 1.50 414.07 B 3 - [[4- [5- NH (trifluor AA nO omethyl) - 1,2,4- oxadiazole

N -3- No

Fyl] phenyl] F methyl] imidazole-4-carboxamide

2.71 - N-benzyl- O 1.42 428.48 B 3- [04- [52- red (trifluoromethyl) - A. 1,2,4-. ; FF oxadiazol -3- yl] phenyl] methyl] imidazole-4-carboxami da tr Load, LCMS pf Entry Name (min) of Method | (ºC) Composite structure mass [M + H]

2,712 No. Oo 1.31 392.09 B cyclobuti, OS 1-3 ita PA [5- (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxamide

2.713 - N-propyl- O 1.25 380.07 B 3 - [[4- [5- r OS (trifluor PAL omethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole- 4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] carboxami da

2.14 - Nometoxi- How 1.09 368.04 B 3 - [[4- [5- OS (trifluor AX omethyl) - 1,2,4-oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxami gives

H

2,715 N- o 1.37 406.09 B cyclopentr i1-3 - [[4- PAL [5- (trifluoromethyl) - 1,2,4- oxadiazol -3-yl] phenyl]

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure compound mass [M + H] methyl] imidazole-4-carboxami da

2.76 morpholino FF 1.05 408.24 B - [3 - [[4- E

N [5- - (trifluoromethyl) - O o 1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazol-4-yl] lmethane in

2.77 N- (2- SS 1.31 418.44 B furilmeti, O 1) -3-114- PA [5- (trifluoromethyl) - 1,2,4-

tr Load, LCMS pf Entry Name (min) of Method | (ºC) Structure composed by mass [M + H] oxadiazol-3-yl) phenyl] methyl] imidazole-4-carboxami da

H

2.78 N-tert-Dix 1.35 394.26 B butyl-3-, OS (raise PA (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imidazole-4-carboxami da

2.79 N-prop-2 RNA 1.19 376.04 B inyl-3-, O (14-152 PA (trifluor tr Charge, LCMS pf Input Name of (min) da Method | (ºC) Structure compound mass [M + H] omethyl) - 1,2,4- oxadiazol -3-yl] phenyl] methyl] imidazole-4-carboxamide

2.80 N-ethyl-N- [as No. 1.13 380.07 B methyl-3- [[4- [5- PAT (trifluoromethyl) - 1,2,4-oxadiazol -3-yl] phenyl) methyl] imi dazol-4-carboxami da

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

[0251] Leaf discs or leaf segments of various plant species are cut from plants grown in a greenhouse. The disks or cut leaf segments are placed in multi-well plates (24-well format) on water-agar. The leaf discs are sprayed with a test solution before (preventive) or after (dressing) inoculation. The compounds to be tested are prepared as solutions in DMSO (max. 10 mg / ml) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying. The inoculated leaf discs or segments are incubated under defined conditions (temperature, relative humidity, light, etc.), according to the respective test system. A single assessment of the disease level is performed 3 to 14 days after inoculation, depending on the pathosystem. The percentage of disease control in relation to untreated leaf discs or control segments is then calculated.

General examples of liquid culture tests on well plates:

[0252] Fragments of mycelia or conidium suspensions of a fungus, freshly prepared from liquid cultures of the fungus or from cryogenic storage, are directly mixed in nutrient broth. DMSO solutions of the test compound (max. Mg / mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 µl of this solution are pipetted into a microtiter plate (96 well format). The nutrient broth containing the fungal spore / mycelium fragments is then added to generate a final concentration of the tested compound. The test plates are incubated in the dark at 24 ºC 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 control is calculated.

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

[0253] Leaf segments of wheat cv. Kanzler were placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf discs were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19 ºC and relative humidity (ur) of 75% under a light regime of 12 hours of light / 12 hours of darkness in a climate-controlled chamber and the activity of a compound was evaluated as a percentage of control of the disease compared to no treatment when an appropriate level of lesions caused by the disease appears in untreated leaf control segments (7 to 9 days after application).

[0254] The following compounds at 200 ppm in the applied formulation resulted in disease control of at least 80%

in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[0255] Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4,

1.5, 1.6, and 1.7.

[0256] Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4

2.5, 2.6, 2.8, 2.9, 2.10, 2.11, 2.12, 2.14, 2.15, 2.16

2.17, 2.18, 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25, 2.26

2.27, 2.28, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35, 2.36

2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.43, 2.44, 2.45, 2.46,

2.47, 2.48, 2.49, 2.50, 2.51, 2.52, 2.53, 2.54, 2.56, 2.57,

2.58, 2.59, 2.60, 2.61, 2.62, 2.63, 2.64, 2.65, 2.66, 2.67,

2.68, 2.69, 2.70, 2.71, 2.72, 2.73, 2.74, 2.75, 2.77, 2.78,

2.79, and 2.80.

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

[0257] Leaf segments of wheat cv. Kanzler are placed on agar in multi-well plates (24-well format). The leaf segments are then inoculated with a spore suspension of the fungus. The plates were stored in the dark at 19 ºC and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19 ºC 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 of disease control compared to absence of treatment when an appropriate level of lesions caused by the disease appears in untreated leaf control segments (6 to 8 days after application).

[0258] The following compounds at 200 ppm in the applied formulation resulted in disease control of at least 80% in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[0259] Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4

1.5, 1.6, and 1.7.

[0260] Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4

2.5, 2.6, 2.8, 2.9, 2.11, 2.12, 2.15, 2.16, 2.17, 2.19,

2.20, 2.21, 2.23, 2.24, 2.25, 2.26, 2.29, 2.30, 2.31, 2.32,

2.33, 2.35, 2.36, 2.37, 2.42, 2.43, 2.56, 2.57, 2.58, 2.59

2.62, 2.63, 2.64, 2.66, 2.67, 2.69, 2.72, 2.73, 2.79, and

2.80.

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

[0261] Soybean leaf discs are placed on agar water in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in an air-conditioned chamber of 24-36 hours in the dark at 20 ºC and 75% ur, the leaf discs are kept at 20 ºC with 12 h of light / day and 75% ur. The activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of lesions caused by the disease appears in untreated leaf control discs (12 to 14 days after application).

[0262] The following compounds at 200 ppm in the applied formulation gave disease control of at least 80% in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[0263] Compounds (from Table T1) 1.1, 1.3, 1.4, and 1.7.

[0264] Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4

2.6, 2.8, 2.9, 2.11, 2.12, 2.14, 2.17, 2.18, 2.19, 2.20,

2.21, 2.22, 2.23, 2.24, 2.25, 2.29, 2.30, 2.31, 2.32, 2.33,

2.34, 2.35, 2.36, 2.37, 2.40, 2.42, 2.43, 2.45, 2.46, 2.52,

2.53, 2.58, 2.59, 2.62, 2.66, 2.67, 2.72, 2.74, 2.75, and

2.79.

Example 4: Fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liquid / cucumber / preventive culture (Anthracnose)

[0265] Conidia of the cryogenic storage fungus are directly mixed in nutrient broth (PDB - potato broth and dextrose). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 ° C and growth inhibition is measured photometrically 3 to 4 days after application.

[0266] The following compounds at 20 ppm in the applied formulation provide disease control of at least 80%

in this test compared to untreated control under the same conditions, which show extensive disease development.

[0267] Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4,

1.5, 1.6, and 1.7.

[0268] Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4,

2.5, 2.6, 2.8, 2.10, 2.11, 2.12, 2.13, 2.14, 2.15, 2.16,

2.17, 2.18, 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25, 2.26,

2.27, 2.28, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35, 2.36,

2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.43, 2.44, 2.45, 2.46,

2.47, 2.48, 2.50, 2.51, 2.52, 2.53, 2.54, 2.55, 2.56, 2.57,

2.58, 2.59, 2.60, 2.61, 2.62, 2.63, 2.64, 2.65, 2.66, 2.67,

2.68, 2.69, 2.70, 2.71, 2.72, 2.73, 2.74, 2.75, 2.77, 2.78,

2.79, and 2.80.

81379 FF 2/7

Ria is C3-scicloalkyl, C3-ecicloalkylCi-alkyl, phenyl, phenylCi-alkyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2 or 3 ring members independently selected from the group consisting of in O, S, N or S (0) ,, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 2 , 3 or 4 heteroatoms individually selected from N, O and S,

and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0), and

R '"? is hydrogen, Cisalkyl, Ci-shaloalkyl or cyclopropyl, or

R'º and Rr, together with the nitrogen atom to which they are attached, form a 4- to 6-membered monocycle optionally containing a heteroatom or additional group selected from O, S, S (0) 2, C (O0) and NR, or

R'º and Rr, together with the nitrogen atom to which they are attached, form a spirobyclic ring system with up to 8 members optionally containing a heteroatom or additional group selected from O, C (O0) and NRº;

Rº is hydrogen, methyl, methoxy, formyl or acyl;

or

81379 FF 3/7

(ii) R 'represents -C (0) OR'º, where:

R'ºe is Corsalquila, Ci-chaloalquila, cyanoCi-salquila, hydroxyCi-salquila, Ci-2alkoxyC; calkyl, Ci-2alcoxyC1: - 2alcoxyCi.alkyl, Ci-2haloalkoxyCi- «xalkyl, C3-salquinyl, C3-salquinyl, C3-salquin haloalkenyl, N-Ci-zalkylaminoCi-xalkyl, N, N-di-Ci-zalkylaminoCi-salkyl; or

R'º is C3-scicloalkyl, C3-scicloalkylCi-2alkyl, phenyl, phenylCi2zalkyl, heterocyclyl or heterocyclylC1-2alkyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2 or 3 ring members independently selected from the group consisting of O, S, N or S (0) »with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl or heteroarylCi-calkyl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S,

and in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which can be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, cyclopropyl or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted with 1 or 2 groups that are oxo (= 0O);

or

(iii) R 'represents -C (O) C (O) N (R'º%) (R'º), where

R'º is Cisalquila, Ci-ahaloalkila, cyanoCi-salquila, hydroxyCi- «alkyl, Ci-3zalcoxyCrz-, alkyl, Ci-2haloalkoxyC1- salquila, C3-salquila, C3-salquinila, hydroxila, aminoCi-

81379 FF 4/7 salkyl, N-CisalkylaminoCi-csalkyl, N, N-diCi-calkylamino, pyrrolidin-1-amino, piperidin-1-amino, morpholin-4-amino, C1-saloxy, C3a-ahaloalkyloxy, C3aalkyloxy, C3alkenyl , cyclopropylCi-alkoxy, (Ci-salkyl) -ON = C (H) Ci- «xalkyl-, or

R'º is C3-ecicloalkyl, C3-ecicloalkylC; i-calkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1, 2 or 3 ring members independently selected from the group consisting of in O, S, N, SOx, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, in which the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S,

wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy , or the cycloalkyl or heterocyclyl fraction is optionally substituted with 1 or 2 groups that are oxo (= 0); and

R7º is hydrogen, Cisalkyl, Ciafluoroalkyl, cyclopropyl, cyclopropylmethyl;

or

(iv) R 'represents -C (0) C (0) -OR'í, where:

R'f is hydrogen, Ci-salquila, Ciashaloalkila, C3-salquenila, C3a-salquinila, or

R'f is C3-ecicloalkyl, C3-ecicloalkylC; i-calkyl, phenyl, heterocyclyl, where the heterocyclyl fraction is a non-aromatic ring with 4 to 6 members comprising 1 or

Claims (15)

81379 FF 5/7 2 ring members independently selected from the group consisting of O, S, N, SO7z, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, where the heteroaryl fraction is an aromatic ring with 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N, O and S; or (v) R 'represents -C (0) C (O) R'º9, where: R'º is hydrogen, Ci-salquila or cyclopropila; listen? represents (Ci-asalkyl) -ON = C (H) -, (C1- 1haloalkyl) -ON = C (H) -, (C3-salt keni1) -ON = C (H) -, (C3-salquinyl) - ON = C (H) - or benzyl-ON = C (H) -; a salt or an N-oxide of it. 2. Compound according to claim 1, characterized by the fact that R! ' up to Rº are hydrogen. 3. A compound according to any one of claims 1 and 2, characterized by the fact that Rº and Rº are hydrogen. Compound according to any one of claims 1, 2 and 3, characterized by the fact that Rº 'represents - C (O) N (R2) (R' ”). Compound according to any one of claims 1, 2, 3 and 4, characterized by the fact that R'º is Ciasalquila, Ci-2rfluoroalkyl, cyanoCizalquila, hydroxyCizalquila, C1 2alcoxyCi-2alkyl, CiofluoroalcoxyCizalquila, Casalquenila, C3 , aminoCi-alkyl, amino, hydroxyl, C-calcoxy, C3a-salkenyloxy, C3a-uhaloalkyloxy, Casalquinyloxy. A compound according to any one of claims 1, 2, 3, 4 and 5, characterized by the fact that RP is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. 81379 FF 6/7 Compound according to any one of claims 1, 2 and 3, characterized by the fact that R 'represents - C (0) OR. A compound according to any one of claims 1, 2 and 3 or 7, characterized by the fact that R'º is C> - salquila, Ci-sfluoroalkyl, cyanoCi-2alkyl, hydroxyC1: - 2alkyl, Ci-calcoxyCralquila, C1-alkoxyC1-alkoxyCicalkyl, C1-2haloalkoxyC1-alkylalkyl, C3aalkenyl, C3a4alkynyl, C3- ahaloalkenyl, N-Ci1-2alkylaminoCi-zalkyl, N, N-di-C1- 2alkylaminoCi-calkyl. Compound according to any one of claims 1, 2 and 3, characterized by the fact that R 'represents - C (0) C (O) N (R'9) (R'º) where: R' º is Ciasalquila, Cicfluoroalkyl, cyanoCi-zalkyl, hydroxyCi-calkyl, Ci-2calcoxyCzalquila, Ci-2haloalcoxyC1- 2alkyl, C3-aalkenyl, C3a-ialquinyl, hydroxyl, aminoC1- 2-Alkyl, C-alkyl-Alkyl, C-alkyl ahaloalkyloxy, C3asalkenyloxy, C3a4salquinyloxy, and R'ºe is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. Compound according to any one of claims 1, 2 and 3, characterized in that R 'represents (C1- 2 alkyl) -ON = C (H) -, (Ci-afluoroalkyl) -ON = C (H ) -, (C3-salkenyl) -ON = C (H) -, (C3asalquinyl) -ON = C (H) - or benzyl-O- N = C (H) -. A compound according to any one of claims 1, 2 and 3 or 10, characterized by the fact that R 'represents (Ci-2alkyl) -ON = C (H) - or (Ci-rfluoroalkyl) -ON = C ( H)-. 12. Agrochemical composition characterized by the fact that it comprises a fungicidal effective amount 81379 FF 7/7 of a compound of Formula (I), as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 11. 13. Composition according to claim 12, characterized in that it additionally comprises at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier. 14. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized by the fact that a fungicidal effective amount of a compound of Formula (II), as defined in any of claims 1, 2, 3, 4 , 5, 6, 7, 8, 9, 10 and 11, or a composition comprising this compound as an active ingredient, is applied to plants, their parts or their locus. 15. Use of a compound of Formula (II), as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8, 9, and 11, characterized by the fact that it is used as a fungicide.