BR112020000463A2 - 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

R? º is R /, where

(i) R 'represents -N (R'º2) (R'? »), where:

R'º is hydrogen, Co-salquila, Ci-salquilcarbonila, Ci-salcoxicarbonila, Ci-aalcoxiCi-salquilcarbonila, aminocarbonila, N-Ci-salquilaminocarbonila, N, N-diC1- salquilaminocarbonila, N-Ci-salcoxiaminocarbonila, N-C1- salkyl-N-Ci-salcoxy-aminocarbonyl, Cicalkylsulfonyl, No. Ci-salkylaminosulfonyl, N, N-diCi-salkylaminosulfonyl, Ci-salkildicarbonyl, Ci-salcoxidicarbonyl, N-C1- alkalkylaminodicarbonyl, N, N-diCi-sal, -salcoxiaminodicarbonyl, N-Ci-salkyl-N-Cicsalcoxy-aminodicarbonyl, Ci-zalkylcarbonylCi-salkylcarbonyl, (Ci salkyl) -ON = C (H) Ci. «alkylcarbonyl-, or

Ra is C3a-scicloalkylcarbonyl, phenylcarbonyl, heterocyclylcarbonyl in which 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, SO; with the proviso that the heterocyclyl cannot contain 2 contiguous atoms selected from O and S, heteroarylcarbonyl 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, C3- ecicloalkylsulfonyl, or phenylsulfiphonyl,

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);

RP is hydrogen, Ci-salquila, Ci-saloxy, C1- afluoroalkyl, cyclopropyl, cyclopropylmethyl; or

R '"º and R'” ", together with the nitrogen atom to which they are attached, form a 4, 5 or 6 membered cycle or a 7 to 11 membered spirocyclic ring system optionally containing an additional heteroatom or group selected from O, S, S (0) »x, C (O) and NRº;

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

or

(ii) R 'represents - (Ci-3alkyl) -N (R'e) (R1º), where: R' "ºe is hydrogen, Ci-salquila, Ci-salquilcarbonila, haloC1i- salquylcarbonila, Ci-salcoxicarbonila, Ci -aalkoxyC1: - salkylcarbonyl, aminocarbonyl, N-C1- salkylaminocarbonyl, N, N-diCi- «xalkylaminocarbonyl, N-C1- salcoxyminocarbonyl, N-Ci-salkyl —- N-Ci-salcoxy-aminocarbonyl, Ci-salquilsulfonyl, N- C1- salkylaminosulfonyl, N, N-diCisalkylaminosulfonyl, C1- salkyl dicarbonyl, Ci-salcoxidicarbonyl, N-C1- salkylaminodicarbonyl, N, N-diCi-salkylaminodicarbonyl, N-Ci-salcoxyminodicarbonyl, N-Ci-amyl-alkoxy-Nicaragua CicalkylcarbonylCisalkylcarbonyl, C1-2alkoxycarbonylCi- «salkylcarbonyl or

R'º is C3a-scicloalkylcarbonyl, phenylcarbonyl, heterocyclylcarbonyl in which 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, SO ; with the proviso that the heterocyclyl cannot contain 2 contiguous atoms selected from O and S,

heteroarylcarbonyl in which the heteroaryl fraction is a 5- or 6-membered aromatic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, C3-cycloalkylsulfonyl or phenylsulfonyl;

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);

R'º * is hydrogen, Cisalkyl, Ci-saloxy, C1- afluoroalkyl, cyclopropyl, cyclopropylmethyl; or

(iii) R 'represents - (Ci-3zalkyl) -C (O) R'º, where: R'º is hydrogen, Ciaalkyl, hydroxyl, Cisaloxy, amino, N-Ci-salquilamino N, N-diCi-salquilamino , N-Ci-'alkoxyamino, N-Ci-salkyl-N-Ci-salcoxy-amino;

or

(iv) R 'represents - (Ci-3salkyl) - (R' ”), where R'f is halogen, cyano, hydroxyl, formyl, Cisalkyl (C = 0) O-, methoxy, Ci2fluoroalkyl or (Cisalkyl) - ON = C (H) -;

or a salt or an N-oxide of it,

with the proviso that the compound of Formula (I) is not [1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] triazol-4-yl acetate ] lmethyl,

Tert-butyl N - [[1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] triazol-4-yl] methyl] carbamate,

3- [4 - [[4- (ethoxymethyl) triazol-l1-yl] methyl] phenyl] -5- (trifluoromethyl) -1,2,4-oxadiazole, N- [1-methyl-l1- [1- [ [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] triazol-4-yl] ethyl] benzamide, or N- [2- [1 - [[4- [ 5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazol-4-yl] ethyl] acetamide.

[0003] Surprisingly, it has been 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 (I). 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 for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidal effective amount of a compound of Formula (1), 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 (IL) 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 -C (0O) CH; 3 group.

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

[0013] As used here, the term "Ciçcalquila" refers to a straight or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms and which is attached to the remainder of the molecule by a single bond. Cisalquila, Ciszalquila and Cizalquila must be considered accordingly. Examples of Ci-salquila include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl and l-dimethylethyl (t-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 -CH2CHi-.

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

[0015] As used herein, the term "Ci-« haloalkyl "refers to a Ci-zalkyl radical as generically defined above substituted with one or more equal or different halogen atoms. Examples of Cishaloalkyl include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.

[0016] As used herein, the term "CisalcoxyCisalkyl" refers to a radical of the formula R1, -O-Ra- where Rv is a Ci-salkyl radical as generically defined above, and Ra is a Ci4salkylene radical as generically defined above .

[0017] 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.

[0018] As used herein, the term "cyanoCisalkyl" refers to a Cisalkyl radical as generically defined above substituted with one or more cyan groups.

[0019] As used here, the term "Cisalkylcarbonyl" refers to a radical of the formula -C (O) R. where Ra is a Cisalkyl radical as generically defined above.

[0020] As used herein, the term "Ci-zalcoxyCi-alkoxyC: - salkyl" refers to a radical of the formula R. = ORvORc-, where Rv and Rc are Ci-calkylene radicals as generically defined above, and Ra. is a Cisalkyl radical as generically defined above.

[0021] As used here, the term "Cisxalkoxycarbonyl" refers to a radical of the formula RaOC (0) -, where Ra is a Cisalkyl radical as generically defined above.

[0022] As used herein, the term "N-Cisalkylamino" refers to a radical of the formula RaNH- where Ra is a Ci-salkyl radical as generically defined above.

[0023] As used herein, the term "N, N-diCi-salkylamino" refers to a radical of the formula Ra (Ra) N- where Ra is a Ci-salkyl radical as generically defined above.

[0024] 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 C3-ecicloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl and cyclohexen-3-yl.

[0025] As used here, the term "heteroaryl" generically refers to a 6-membered monocyclic aromatic ring radical comprising 1 or 2 individually selected heteroatoms of 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, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyrimidyl and pyridyl.

[0026] As used herein, the term "heterocyclyl" or "heterocyclic" refers to a non-aromatic monocyclic ring with 4 to 6 saturated or partially saturated stable members, 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,

hydrothiopyranil, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl and morpholinyl.

[0027] 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 (1). Likewise, Formula (1) is intended to include all possible tautomers (including lactam-lactime tautomerism and tautomerism. “Keto-enol), when present. The present invention includes all possible tautomeric forms for a compound of Formula (1).

[0028] 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.

[0029] 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.

[0030] According to the invention, the compound of Formula (I is not:

N- [2- [1 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] imidazol-4-yl] Jetyl] acetamide.

[0031] The following list provides definitions, including preferred definitions, for the substituents Z, R !, R ?, Ri, Ri, R5, Rº and Rº (R '(Re, R'º, Ric, Rd, Re, R1E )) 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.

[0032] R !, R2º, Rà, Rº are independently selected from hydrogen or fluorine, where 0, 1 or 2 of Rl, R2, Rº and Rº are fluorine.

[0033] In certain embodiments of the invention, R !, R2à, Rà and R $ are hydrogen; Rº, R? À and Rº are hydrogen and R! it is fluorine; R !, R? and Rº are hydrogen and Rº is fluorine; R! and R2 are fluorine and Rê and Rº are hydrogen; R 'and R? are fluorine and R? and Rº are hydrogen, or R 'and R are hydrogen and Rº and Rº are fluorine. Preferably, R! up to Rº are hydrogen, or R! is fluorine and R? up to Rº are hydrogen.

[0034] Rº and Rº independently represent hydrogen or methyl. Preferably, Rº and Rº are both hydrogen, or Rº is hydrogen and Rº is methyl. Most preferably, Rº and Rº are both hydrogen.

[0035] Z represents a heteroaryl group linked to C (Rº) (R $) via a CN bond, where the heteroaryl is a 5-membered aromatic ring selected from pyrazolyl, 3,5-dimethylpyrazolyl, 1,2,3- triazolyl, 1,2,4-triazolyl, imidazolyl or tetrazolyl and is replaced with a single group Rº.

Rz is R7.

R7 can represent -N (R7a) (R7b), where: R7a is hydrogen, C2-5alkyl, Cl-5alkylcarbonyl, Cl-4alkoxycarbonyl, Cl-4alkoxyCtCl-4alkylcarbonyl, aminocarbonyl, N-Cl-4alkylaminocarbonyl, N, N-diCl - 4alkylaminocarbonyl, N-Cl-4alkoxyminocarbonyl, N-Cl1- 4alkyl-N-Cl-4alkoxy-aminocarbonyl, Ccl-4alkylsulfonyl, N-Cl-4alkylaminosulfonyl, N, N-diCl-4alkylaminosulfonyl, Cl-4-alkylidic -Cl-4alkylaminodicarbonyl, N, N-diCl- 4alkylaminodicarbonyl, N-Cl-4alcoxiaminodicarbonyl, N- Cl-4alkyl-N-Cl-4alkoxy-aminodicarbonyl, cl- 2alkylcarbonylCl-4alkylcarbonyl, (Cl-4-Alkyl) (H) Cl-4alkylcarbonyl-, or R7la is C3-6cycloalkylcarbonyl, phenylcarbonyl, heterocyclylcarbonyl in which 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 heterocyclyl cannot contain 2 contiguous atoms selected from O and S, heteroarylcarbonyl in which the heteroaryl fraction is a 5- or 6-membered aromatic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, C3-6cycloalkylsulfonyl, or phenylsulfonyl, in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl 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 R7b is hydrogen, Cl-4alkyl, Cl-4alkoxy, Cl-4fluoroalkyl, cyclopropyl, cyclopropylmethyl; or R7a and R7b, together with the nitrogen atom to which they are attached, form a 4, 5 or 6 membered cycle or a 7 to 11 membered spirocyclic ring system optionally containing a heteroatom or additional group selected from O, S , S (0) 2, C (O) and NR8.

[0037] Rº is hydrogen, methyl, methoxy, formyl or acyl.

[0038] Preferably, R'1º is Cisalkylcarbonyl, C17- aalkoxycarbonyl, Ci-salcoxyCisalkylcarbonyl, aminocarbonyl, N-Ci-salkylaminocarbonyl, N, N-diC1- salkylaminocarbonila, N-Ci-salcoxiaminocarbonila, N-C-a1- Al- -salcoxy-aminocarbonyl, Cialkylsulfonyl, No. Ci-salkylaminosulfonyl, N, N-diCi-salkylaminosulfonyl, Ci-salkildicarbonyl, Ci-salcoxidicarbonyl, N, N-C1- salkylaminodicarbonyl, N, N-diCiyl-salquyl -aminodicarbonyl, N-N-diCiyl-salkylaminodicarbonyl Ci-salkyl-N-Cisalcoxy-aminodicarbonyl, Ci-calkylcarbonylCi-salkylcarbonyl, (C1-salkyl) -ON = C (H) Ci-salkylcarbonyl-. More preferably, Ra is Ci-calkylcarbonyl, C1-3zalcoxycarbonyl, Ci-2alkoxyCi-2alkylcarbonyl, aminocarbonyl, N-Ci-salkylaminocarbonyl, N, N-diC1-salkylaminocarbonyl, N-Ci-salcoxiaminocarbonyl, N-C1- 2-alkyl -alkoxy-aminocarbonyl, Cicalkylsulfonyl, N- C1-2alkylaminosulfonyl, N, N-diCi-2alkylaminosulfonyl, Ci-2alkylcarbonyl, Ci-calcoxidicarbonyl, N-C1- 2alkylaminodicarbonyl, N, N-di-alkoxy-alkali -C1i-2alkyl-N-C1-alkoxy-

aminodicarbonyl, C1-2alkylcarbonylC1-2alkylcarbonyl, (C1-2alkyl) -O-N = C (H) C1-alkylcarbonyl-.

[0039] Preferably, R '"º is C3-« gcycloalkylcarbonyl, phenylcarbonyl, heterocyclylcarbonyl wherein the heterocyclyl fraction is a 5- or 6-membered non-aromatic ring comprising 1 or 2 ring members independently selected from the group consisting of O, S and N, with the proviso that the heterocyclyl cannot contain 2 contiguous atoms selected from O and S, heteroarylcarbonyl 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 , Ca-cycloalkylsulfonyl, or phenylsulfonyl, in which the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety 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).

[0040] In some embodiments of the invention, preferably Ra is C1-salkylcarbonyl, C1-alkoxycarbonyl, C1-salcoxyCisalkylcarbonyl, aminocarbonyl, N-C1-salkylaminocarbonyl, N, N-diC1-salkylaminocarbonyl, N-Ci-salcooxycarbonyl, N-C - aalkyl-N-Ci-saloxy-aminocarbonyl, Cisalkylsulfonyl, C3-ecicloalkylcarbonyl, phenylcarbonyl or heteroarylcarbonyl in which the heteroaryl fraction is an aromatic ring with 5 members comprising 1 or 2 heteroatoms individually selected from N, O and S, and in which the cycloalkyl fraction,

phenyl or heteroaryl 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. More preferably, Ra is C1-salkylcarbonyl, C1-alkoxycarbonyl, C1-2alkoxyC1: - 2alkylcarbonyl, aminocarbonyl, N-C1-2alkylaminocarbonyl, N, N-diCi -alkylaminocarbonyl, N-C1i- 2-Alkoxycarbonyl, N-C1-1-N-C1-2 Ci-alkoxy-aminocarbonyl, Ci-alkalkylsulfonyl, cyclopropylcarbonyl, phenylcarbonyl or imidazolylcarbonyl.

[0041] Preferably, R '? ” is hydrogen or methyl.

[0042] -R 'can represent - (Ci-szalkyl) -N (R'o) (R *%), where: R'ºe is hydrogen, Ci-salquila, Ci-salquilcarbonila, haloCi- «salquilcarbonila, Ci -aalkoxycarbonyl, Ci-saloxyC1; - salkylcarbonyl, aminocarbonyl, N-C1- salkylaminocarbonyl, N, N-diCi- 'xalkylaminocarbonyl, N-C1- salcoxyminocarbonyl, N-Ci-salquyl-N-Cisalcoxy-aminocarbonyl, Ci-salinyl, -C1- salkylaminosulfonyl, N, N-diCisalkylaminosulfonyl, C1- salkyl dicarbonyl, Ci-salcoxidicarbonyl, N-C1- aalkylaminodicarbonyl, N, N-diCi-salkylaminodicarbonyl, N-Ci-salcoxyminodicarbonyl, or N-Ci-sal-alkalyl aminodicarbonyl, Ci-calkylcarbonylCi-salkylcarbonyl, C1- 2 alkoxycarbonylCi-salkylcarbonyl or R'º is C3a-scicloalkylcarbonyl, phenylcarbonyl, in which the heterocyclyl fraction is a non-aromatic ring with 4 or 6 members that comprises 1 to 3 members, comprising 1 to 3 members ring independently selected from the group consisting of O, S, N, SOz with the proviso that the heterocyclyl cannot c onter 2 contiguous atoms selected from O and S, heteroarylcarbonyl 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, C3 scicloalkylsulfonyl or phenylsulfonyl; 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 R'º * is hydrogen, Cisalkyl, Ci-saloxy, C1- afluoroalkyl, cyclopropyl, cyclopropylmethyl.

[0043] Preferably, R 'can represent - (C1- 2 alkyl) -N (R'º) (R'º).

[0044] Preferably, R'º is Ci-salkylcarbonyl, haloC1-salkylcarbonyl, Ci-salcoxycarbonyl, Ci-aalkoxyC1- salkylcarbonyl, aminocarbonyl, N-C1- salkylaminocarbonyl, N, N-diCisalkylaminocarbonyl, N-C1-saloxy, N-C1-saloxy -salkyl-N-Cicsalcoxy-aminocarbonyl, Cisalkylsulfonyl, N-C1- salkylaminosulfonyl, N, N-diCi- «alkylaminosulfonyl, C1- salkylcarbonyl, Ci-salcoxidicarbonyl, N-C1- asalkylaminodicarbonyl, N, N-diCyl -Ci-salcoxiaminodicarbonyl, or N-Cisalkyl-N-Cisalcoxy-aminodicarbonyl, C1-alkylcarbonylCi-salkylcarbonyl or C1-2alkoxycarbonylCi- «alkylcarbonyl. More preferably,

R'º is Ci-salkylcarbonyl, haloCi-2alkylcarbonyl, C1-zalcoxycarbonyl, Ci-2alcoxyCi-alkylalkylcarbonyl, aminocarbonyl, N-Ci-2ralkylaminocarbonyl, N, N-diC1- 2alkylaminocarbonyl, N-Ci-2-alkoxy, N-Ci-2-alkoxy N-C1-alkoxy-aminocarbonyl, C1-alkylsulfonyl, N-C1-2alkylaminosulfonyl, N, N-diCi-2alkylaminosulfonyl, C1-2alkylldicarbonyl, Ci-2alkoxycarbonyl, N-C1-2alkylaminodicarbonyl, N, N-diC1, N, N-diC1 C1-2alkoxyminodicarbonyl, N-C1-1-2alkyl-N-C1-alkoxy-aminodicarbonyl, C1-2alkylcarbonylCi -alkylcarbonyl or C1-2alkoxycarbonylCi -alkylcarbonyl.

[0045] In some embodiments of the invention, preferably, R 'is Ci-salkylcarbonyl, haloC1-salkylcarbonyl, Ci-salcoxycarbonyl, Ci-aalkoxyC1: - salkylcarbonyl, aminocarbonyl, N-C1- asalkylaminocarbonyl, N, N-diCi-salylaminocarbonyl C1-salkylsulfonyl, Ci-salkylcarbonyl, Cr-salcoxidicarbonyl, Ci-calkylcarbonylCi-salkylcarbonyl, C1- 2alcoxycarbonylCi-salkylcarbonyl, C3-ecicloalkylcarbonyl, phenylcarbonyl, heterocyclylcarbonyl which is a heterocyclylcarbonyl member which is a 5-membered heterocyclyl ring with a 5-membered heterocyclyl of ring independently selected from the group consisting of O, S, N, with the proviso that the heterocyclyl cannot contain 2 contiguous atoms selected from O and S, heteroarylcarbonyl in which the heteroaryl fraction is a 5-membered aromatic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, where the cycloalkyl, phenyl, heterocyclyl or heteroaryl fraction is optionally substituted with a single substance selected hydroxyl, formyl, acyl,

cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy. More preferably, R'º is Ci-salkylcarbonyl, haloCi-ralkylcarbonyl, Ci- 3-alkoxycarbonyl, Ci-2-alkoxyCi-ralkylcarbonyl, aminocarbonyl, N-Ci-2-alkylaminocarbonyl, N, N-diC1- 2alkylaminocarbonyl, Ci-2, C-2 -2alkoxycarbonyl, C1-2alkylcarbonylCi -alkylcarbonyl or CizalcoxycarbonylC1- 2alkylcarbonyl, cyclopropylcarbonyl, phenylcarbonyl optionally substituted (for example, in position 4) with a single substituent selected from hydroxyl, formyl, acyl, cyan, chlorine, halide (for example, chlorine or fluorine) methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy or difluoromethoxy, furanylcarbonyl (for example, furan-2-ylcarbonyl) or isoxazolylcarbonyl (for example, isoxazol-S5-ylcarbonyl).

[0046] Preferably, R'º is hydrogen or methyl.

[0047] -R 'can represent - (Ci-3alkyl) -C (O) R'º, where: R' "º is hydrogen, Cisalkyl, hydroxyl, Cisaloxy, amino, N-Ci-salkylamino N, N- diCi-salkylamino, N-C1-saloxyamino, N-C1-salkyl-N-C1-3 alkoxy-amino.

[0048] Preferably, R '"º is hydrogen, Cyzalkyl, hydroxyl, C1-2alkoxy, amino, N-C1-2alkylamino N, N-diC1i 2alkylamino, N-Ci-2alkcoxyamino, N-Ci-2alkyl-N-Ci- calcoxy-amino. More preferably, R '"º is hydrogen, methyl, ethyl, iso-propyl, hydroxyl, Ci-calcoxy or amino.

[0049] -R '? can represent - (Ci-3alkyl) - (R '”), where: R'f is halogen, cyano, hydroxyl, formyl, Ci-aalkyl (C = 0) O-, methoxy, Ci-2fluoroalkyl or (Ci- salkyl) -ON = C (H) -. Preferably, R'f is chlorine, fluorine, cyano, hydroxyl,

formyl, C1-2alkyl (C = 0) O-, methoxy, C1-fluoroalkyl or (C1-2alkyl) -O-N = C (H) -.

[0050] In some embodiments of the invention, R 'may represent -N (R'º) (R' »).

[0051] In some embodiments of the invention, R 'may represent - (Ci-3zalkyl) -N (R's9) (R'º).

[0052] In some embodiments of the invention, R 'may represent - (Ci-3alkyl) -C (O) R'º.

[0053] In some embodiments of the invention, R 'may represent - (Ci-3alkyl) - (R').

[0054] The Ci-zalkyl fragment defined for R 'as - (C1-3alkyl) -N (R'e) (R1º), can preferably be Ci-2alkylene or Car3alkylene, or individually a methylene, ethylene or n-propylene group .

[0055] The Ci-zalkyl fragment defined for R 'as - (C1-3alkyl) -C (O) R'º, may preferably be C1-alkylene or Cr-3alkylene, or individually a methylene, ethylene or n-propylene group .

[0056] The C1-3alkyl fragment defined for R 'as - (C1-zalkyl) - (R'!) Can preferably be C1-2 alkylene or C2-alkylene, or individually a methylene, ethylene or n-propylene group.

[0057] Preferably, the compound according to Formula (1) is selected from a compound 1.1 to 1.56 described in Table T1 (below).

[0058] The compounds of the present invention can be enantiomers of the compound of Formula (I) as represented by a Formula (Ia) or a Formula (Ib), where Rº and Rº are different substituents.

invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0075] The compounds of Formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for plant pest control or in non-living materials for the control of microorganisms that cause deterioration or potentially organisms harmful to man. The new compounds are distinguished by their excellent activity at low application rates, by being well tolerated by plants and by being environmentally safe. They have very useful healing, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of the Formula (IT) can be used to inhibit or destroy the pests that occur in plants or parts of plants (fruit, flowers, leaves, stems, tubers, roots) from different cultures of useful plants, while protecting, for example, of phytopathogenic microorganisms, also those parts of plants that grow later.

[0076] The present invention additionally relates to a method for controlling or preventing 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 (I) is applied to plants, their parts or their locus.

[0077] It is also possible to use compounds of Formula (I) 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.

[0078] 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 (1) before planting: seed, for example, can be covered before being sown. The active compounds of Formula (1) 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 material of propagation is being planted, for example, in the seed groove during sowing, the invention also relates to such methods of treatment of plant propagation material and to the plant propagation material thus treated.

[0079] 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.

[0080] Additionally, the invention can be used to protect non-living materials from fungal attack, for example, construction wood, wall panels and paint.

[0081] The compounds of Formula (1) 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:

[0082] 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, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp.

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

[0083] The compounds of Formula (I) can be used, for example, in grass, ornamental plants such as flowers, shrubs, leafy or evergreen trees, for example, conifers, as well as for injection into trees, management of pests and the like.

[0084] 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, eg almond, cashew, peanut seed, hazelnut,

peanuts, pecans, pistachios and walnuts; 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 .

[0085] The term "useful plants" should be understood to also include useful plants that have been made tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, 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.

[0086] 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.

[0087] Examples of such plants are: YieldGard8O (variety of apples that expresses a CryIA toxin (b)); YieldGard Rootworm & (more variety that expresses a CryIIIB toxin (bl)); YieldGard Plus8 (more variety that expresses a CryIA toxin (b) and a CryIIIB toxin (bl)); Starlink & (more variety that expresses a Cry9 toxin (c)); Herculex IO (variety of maize that expresses a CryIF toxin (a2) and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuUuCOTN 33B8 (cotton variety that expresses a CryIA toxin (c)); Bollgard IO (cotton variety that expresses a CryIA toxin (c)); Bollgard IIGO (cotton variety that expresses a CryIA toxin (c) and a CryIIA toxin (b)); VIPCOT & (cotton variety that expresses a VIP toxin); NewLeaf & (potato variety that expresses a CryIIIA toxin); NatureGardO Agrisureo GT Advantage (trait of tolerance to glyphosate GA21), AgrisureG CB Advantage (trait of corn borer (CB) Btl1), Agrisure6 RW (trait of corn rootworm) and Protecta € O.

[0088] 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.

[0089] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from

Bacillus cereus or Bacillus popilliae, or insecticidal proteins from Bacillus thuringiensis, such as —8-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 from nematode-colonizing bacteria, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect specific neurotoxins; toxins produced by fungi, such as 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.

[0090] 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 Cry3AO055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03/018810 ).

[0091] 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.

[0092] 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.

[0093] 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).

[0094] 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 Rootworm8 (more variety that expresses a Cry3Bbl toxin); YieldGard Plus & (variety of apples 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); NuUuCOTN 33B8 (cotton variety that expresses a CrylAc toxin); Bollgard IO (cotton variety that expresses a CrylAc toxin); Bollgard IIO (cotton variety that expresses a CrylAc toxin and a Cry2Ab); VipCotO (cotton variety that expresses a Vip3A toxin and a CrylAb); NewLeaf & (potato variety that expresses a Cry3A toxin); NatureGardO, Agrisureo GT Advantage (glyphosate tolerant trait GA21), Agrisure6o CB Advantage (trait of corn borer (CB) Btll1) and Protecta €.

[0095] Additional examples of such transgenic crops are:

1. Btll 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. Bt1l1l maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

2. Btl76 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 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, Maize MON 863 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02/9. MON 863 expresses a Cry3Bbl toxin and is resistant to certain Coleoptera insects.

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

6. Corn 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-ll160 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.

[0096] The compounds of Formula (1) (including any of the compounds 1.1 through 1.56 described in Table T1 (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.

[0097] 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 US 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).

[0098] 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 SYHTO4R event - tolerance to HPPD.

[0099] Under certain circumstances, the compounds of Formula (I) 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.

[0100] Additionally, to date, no cross-resistance has been observed between the compounds of Formula (1) (including any of the compounds 1.1 through 1.56 described in Table T1 (below)) and the current fungicidal solutions used to control Phakopsora pachyrhizi .

[0101] 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.

[0102] Thus, in a preferred embodiment, the compounds of Formula (1) (including any of compounds 1.1 through

1.56 described in Table T1 (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 of fungicides : sterol demethylation inhibitors (DMI), external quinone inhibitors (QolI) and succinate dehydrogenase inhibitors (SDHI).

[0103] The compounds of Formula (1) (including any of compounds 1.1 to 1.56 described in Table T1 (below)) or fungicidal compositions according to the present invention comprising a compound of Formula (1) can be used in the control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants. In particular, certain varieties of Elite soy plants are known in the scientific literature where stacks of the R gene, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been introgressed in the plant's genome, see, for example: “Fighting Asian Soybean Rust” , Langenbach C, et al., Front Plant Science 7 (797) 2016).

[0104] 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 AG7231 (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 O03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, 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, SOO0O9-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-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. Ia., USA), or Armor 4744 (Armor Seed, LLC, Ar., USA).

[0105] Thus, in an additional preferred embodiment, the compounds of Formula (I) (including any of the compounds

1.1 through 1.56 described in Table T1 (below)), or fungicidal compositions 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 from Elite soy plants in which R gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, were introgressed in the plant's 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.

[0106] 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.

[0107] The term "plants" refers to all the physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[0108] It is understood that the term "plant propagating 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.

[0109] The compounds of Formula (I) can be used in an unmodified form or, preferably, in conjunction with adjuvants conventionally employed in the formulation technique. For this purpose, they can be conveniently formulated in a known manner in emulsifiable concentrates, coated pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, 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.

[0110] 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.

[0111] 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.

[0112] Wettable powders are in the form of finely divided particles that disperse quickly in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include Fuller earth, kaolin clays, silica and other readily moistened organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0113] 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.

[0114] Granular formulations include both extruded and relatively coarse particles and are usually applied without dilution to the area where treatment is required. Typical carriers for granular Formulations include sand, Fuller earth, atapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials that absorb or can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients which may include surfactants such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils, and / or adhesives such as dextrins, glue or synthetic resins.

[0115] Dusts are free-flowing mixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids that act as dispersants and carriers.

[0116] 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 usually porous granules with porous membranes sealing the granule pore openings,

retaining the active species in liquid form within the pores of the granules. The granules typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter. The granules are formed by extrusion, agglomeration or pelletizing, or 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 xanthate.

[0117] 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.

[0118] 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.

[0119] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane,

cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecan, hexadecane, hexadecane, hexadecane , isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methylisoamylketone, methylisobutyl ketone, methyl laurate, octane methyl act, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monoethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, ethanol, 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.

[0120] 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.

[0121] 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 Cl8-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.

[0122] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light blocking agents, compatibilizing agents, antifoaming agents, agents sequestrants, neutralizing agents and buffers, corrosion inhibitors, dyes, flavorings, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0123] 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.

[0124] Pesticide agents are referred to here using their common name; are known, for example, from “The

Pesticide Manual ”, 15th Edition British Crop Protection Council 2009.

[0125] 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.

[0126] The compounds of Formula (1) 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.

[0127] 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 the free form or in the form of agrochemically usable salt, and at least one of the aforementioned adjuvants.

[0128] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of Formula (IL), 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 (1I).

[0129] The compound of Formula (1) 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.

[0130] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzanidide, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, fungicides, fungicides dithiolane,

furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphate fungicides, organo-tinned fungicides, oxatiin fungicides, oxazole fungicides, phenylsulfide fungicides, pyrolysis, fungicides pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazol fungicides, thiazole fungicides, thiazole fungicides thiocarbamate, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0131] Examples of suitable additional active ingredients also include the following: (3-difluoromethyl acid (9-dichloromethylene-1,2,3,4-tetrahydro-1, 4-methane-naphthalen-5-yl1) -amide -l-methyl-1H-pyrazol-4-carboxylic acid, methoxy- [l1-methyl-2- (2,4,6-trichlorophenyl) -ethyl] -amide of 3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl) -amide of 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (1072957- 71-1), 1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl) -amide, [2- (2,4-dichloro-phenyl) -2-methoxy-1 1-methyl-3-difluoromethyl-4H-pyrazol-4-carboxylic acid -methyl-ethyl] -amide, (5-Chloro-2,4-dimethyl-pyridin-3-yl) - (2,3,4- trimethoxy-6-methyl-phenyl) - methanone, (5-Bromo-4-chloro-2-methoxy-pyridin-3-yl) - (2,3,4-

trimethoxy-6-methyl-phenyl) -methanone, 2- (2 - [(E) -3- (2,6-Dichloro-phenyl) -l-methyl-prop-2-en- (E) -ylideneamino-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-l- 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- [2 - [6- (2- cyanophenox i) methyl pyrimidin-4-yloxy] phenyl] 3-methoxyacrylate, (E) -2- [2- [6- (2-thioamidophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E ) Methyl -2- [2- [6- (2- fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2,6-di-fluorophenoxy ) methyl pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] phenyl] -3-methoxyacrylate, (E) - 2- [2- [3- (S-methylpyrimidin-2-yloxy) -phenoxy] phenyl] -3-methyl-methoxyacrylate, (E) -2- [2- [3- (phenyl-sulfonyloxy) phenoxy] phenyl- Methyl 3-methoxyacrylate, methyl (E) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate, (E) -2- [2-phenoxyphenyl] -3-methoxyacrylate methyl, (E) -2- [2- (3,5-dimethyl-benzoyl) pyrrol-1-yl] -3-methyl-methoxyacrylate, (E) -2- [2- (3-methoxyphenoxy) phenyl] - Methyl 3-methoxyacrylate, (E) -2- [2- (2-phenylethen-1-yl) -phenyl] -3-methyl methoxyacrylate, (E) -2- [2- (3,5-dichlorophenoxy) methyl pyridin-3-yl] -3-methoxyacrylate, (E) -2- (2- (3- (1,1,2,2-tetrafluor methyl ethoxy) phenoxy) phenyl) -3- methoxyacrylate, (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methyl methoxyacrylate, (E) -2- (2 - methyl (4-phenoxypyridin-2-yloxy) phenyl) -3-methoxyacrylate, (E) -2- [2- (3-n-propyloxy-phenoxy) phenyl] -3-methyl methoxyacrylate, (E) - Methyl 2- [2- (3- isopropyloxyphenoxy) phenyl] -3-methoxyacrylate, (E) - 2- [2- [3- (2-fluorophenoxy) phenoxy] phenyl] -3-methoxyacrylate, (E) Methyl -2- [2- (3-ethoxyphenoxy) phenyl] -3-methoxyacrylate, (E) -2- [2- (4-tert-butyl-pyridin-2-yloxy) phenyl] -3-methoxyacrylate , Methyl (E) -2- [2- [3- (3- cyanophenoxy) phenoxy] phenyl] -3-methoxyacrylate, (E) - 2- [2- [(3-methyl-pyridin-2-yloxymethyl) methyl phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-methyl-phenoxy) pyrimidin-4-yloxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [ 2- (5-bromo-pyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate, (E) -2- [2- (3- (3-iodopyridin-2-yloxy) phenoxy) phenyl] -3- methyl methoxyacrylate, (E) -2- [2- [6- (2-chloropyridin-3-yloxy) pyrimi methyl din-4-yloxy] phenyl] -3-methoxyacrylate, (E), (E) -2- [2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl) phenyl] -3-methoxyacrylate, (E ) - 2- (2- [6- (6-methylpyridin-2-yloxy) pyrimidin-4-yloxy] phenyl);) - methyl 3-methoxy-acrylate, (E), (E) -2- (2 - methyl (3-methoxyphenyl) methyloximinomethyl] -phenyl) -3-methoxyacrylate, (E) -2- (2- (6- (2-azidophenoxy) -pyrimidin-4-yloxy] phenyl) -3-methoxyacrylate , (E), (E) -2- (2- [6-

methyl phenylpyrimidin-4-1i1l1) -methyloximinomethyl] phenyl) -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-in) , 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-diiodo-2-propenyl alcohol, 3-iodo-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, 4,5-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, ampropylfas, anilazine, anilazine , aureofungin, azaconazole, azafendine, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl- M, benodanyl, benomyl, benquinox, bentaluron, bentiavalicarb, bentiazole, benzalkonium chloride, benzamacryl, benzzamacryl, benzamacril, benz

benzovindiflupir, berberine, betoxazine, biloxazole, binapacril, biphenyl, bitertanol, bitionol, bixafen, blasticidin-S, boscalide, bromotalonil, bromuconazole, bupyrimide, butiobate, butylamine and carbendazimide, carbendazimide, carbendam, carbendam, carbendam, carbendam, carbendam carboxine, carpropamide, carvone, CGA41396, CGA41397, quinomethionate, chitosan, clobentiazone, chloraniformethane, chloranil, chlorphenazole, chloroneb, chloropicrin, chlorothalon, chlorozolinate, clozolinate, climbazol, copper chloride, chloroacylate, such compounds , copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper talate, copper and zinc chromate and Bordeaux, cresol, cufranebe, cuprobam, cuprous oxide mixture , cyzofamide, cyclamfuramide, cycloheximide, cyflufenamide, cymoxanil, cyipendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, des acid idroacetic, di-2-pyridyl disulfide 1,1'-dioxide, diclofluanide, diclomezine, diclone, dichloran, dichlorophene, diclozoline, diclobutrazol, diclocimet, dietofencarb, diphenoconazole, difenzoquat, diflumetorim, diofo-phosphate -propyl-S-benzyl, dimefluazole, dimethaclone, dimetconazole, dimetomorph, dimethyrimol, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, dipyrione, disulfiram, dithimethyl, dithimethyl, dithimethyl, dithimethyldi dodemorfe, dodicin, dodine, doguadine, drazoxolon, edifenfos, enestroburin, epoxiconazole, etaconazole, etem, etaboxam, ethirimol, ethoxyquin, ethylicin, (Z) -N-benzyl-N - ([methyl (methyl-

ethyl thioethylideneaminooxycarbonyl) amino] thio) -fB-alaninate, etridiazole, famoxadone, fenamidone, phenaminosulf, fenapanil, phenarimol, fenbuconazole, fenfuram, fenexamide, fenitropane, phenoxanil, phenoxyphenate, phenoxyphenide, phenoxyphenide, phenoxyphenide, phenoxyphenide, phenoxyphenide, phenoxyphenide , fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorfe, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flussulfamide, flutanil, flutolanil, floxydexyl, fluorohydride, fluorohydrate furametpir, furcarbanil, furconazole, furfural, furmeciclox, furofanato, gliodina, griseofulvina, guazatina, halachrinato, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexiltiofos, hydrargafene, iodine, hydroxy-isoxazol, hydroxy-hexazol iminoctadine, inezine, iodocarb, ipconazole, ipfentrifluconazole iprobenfos, iprodione, iproval icarb, isopropanylbutyl carbamate, isoprothiolane, isopirazam, isothianil, isovaledione, izopamphos, casugamycin, cresoxim-methyl, LY186054, LY211795, LY248908, mancozebe, mandipropamide, mezzanine, manebe, manequin, mercury, meptildinocape, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, methandenone, methanol, methilone, methanol myclozoline, nabam, natamycin, neoasozine, nickel dimethyldithiocarbamate, nitrostyrene,

nitrotal-iso-propyl, nuarimol, octylinone, ofurace, organomercury compounds, orysstrobin, ostol, oxadixil, oxasulfuron, oxatiapiproline, oxin-copper, oxolinic acid, oxpoconazole, oxycarboxine, parinol, pefurazoate, penconazole, pentconazole, pentconazole, pentconazole, pentconazole, , fenamacril, phenazine oxide, phosdiphene, phosethyl-Al, phosphorus acids, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxyrin, polamen, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propaminazoline, propinequinone, propamine, propinequinone , protiocarb, protioconazole, pidiflumetofen, piracarbolide, piraclostrobin, pyramethrostrobin, piraoxystrobin, pyrazophos, pyribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyriophenone, piroquilon, pyroxyquinone, pyroxymethyl, quinoxyron, pyroxymethrol, pyroxymethyl, pyroxymethrol quintozene, rabenzazole, santonin, silkxane, Ssiltiofam, simeconazole, sipconazole, pentachlor sodium phenate, spiroxamine, streptomycin, sulfur, sultropene, tebuconazole, tebfloquine, keyboardoftalam, tecnazene, tecoram, tetraconazole, tiabendazole, thiadifluor, ticiofene, tifluzamide, 2- (thiocyanomethyl) thiothiazine, thiomethanol, thiofanazole, thiofanazole, thiofanazole, thiozone , thioximide, tolclofos-methyl, tolylfluanide, triadimefon, triadimenol, triamiphos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforin, triflumizol, triflumizine, triticonazole, valitazoline, tritazazine, tritazazine, valicon , ziram and zoxamide.

[0132] 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 EpP-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 clorsulony, and cestocides, such as praziquantel and epsiprantel.

[0133] 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 .

[0134] The compounds of the invention can be used in combination with derivatives and analogs of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO

93/19053, WO 93/25543, EP O 626 375, EP O 382 173, WO 94/19334, EP O 382 173 and EP O 503 538.

[0135] 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.

[0136] 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.

[0137] 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: aphosphate, azametiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos -ethyl, cadusaphos, chlorethoxyphos, chlorpyrifos, chlorfenvinfos, chlormphs, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialiph, diazinon, dichlorvos, dichrotophos, dimetoate, disulfoton, etion, etoprofos, fenifos, fenifos, fenifos, fenifos, fenifos, fenifos, fenifos, fenofos, , fensulfotion, fention, flupirazofos, formotion fonofos, fostiazato, heptenofos, isazofos, isothioato, isoxation, malation, metacrifos, metamidofos, metidation, methyl-paration, mevinfos, monocrotofos, nalede, metetoate, paremoxation, paremoxation, paroxoxation methyl, fentoate, fosalone, phospholane, fosfocarb, fosmet, fosfamidon, phorate, foxim, pyrimiphos, pyrimiphos-methyl,

profenofos, propafos, proetamfos, protiofos, piraclofos, piridapention, quinalfos, sulprofos, temefos, terbufos, tebupirimfos, tetrachlorvinfos, timeton, triazofos, triclorfon, vamidotion.

[0138] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloetocarb, ethiofencarb, phenoxycarb, fentiocarb, methacrocarb, methoxy, 5-carcinyl, isoprocarb, 5 -m- cumenylbutyryl (methyl) carbamate, oxamil, pyrimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

[0139] 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, tetrahydrin, tetrahydrin, tetrahydrin, tetrahydrin, fluvalinate, teflutrin, tralometrine, zeta-cypermethrin.

[0140] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas chlorfluazuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,

teflubenzuron, triflumuron, buprofezin, diophenolane, hexitiazox, ethoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; cc) juvenoids: pyriproxyphene, methoprene (including s-methoprene), phenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[0141] Other antiparasitic agents: acequinocil, amitraz, AKD-1022, ANS-118, azadiractin, Bacillus thuringiensis, bensultap, biphenazate, binapacril, bromopropylate, BTG-504, BTG-505, camfeclor, cartap, chlorfenzyme, chlorobenzylate, 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, silomadin, spinosad, tebufenpirade, tetradifon, tetranactin, thiaclopride, thiocyclam, tiametoxam, tolfenpirade, triazaine, triaxine, triethoxine , verbutina, ve rtalec, YI-5301.

[0142] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis endotoxin delta, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0143] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0144] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinoma, florfenicol, buserelin, cefovantin, cefovecine, trefovinine, trefovinine, cefovecin, trefovinine, cefovecin, trefovina, .

[0145] The following mixtures of the compounds of formula (1) with active ingredients are preferred. The abbreviation “TX” means a compound selected from the group consisting of the compounds represented in Tables 1.1 through 1.6 and Tables

2.1 through 2.6 (below), or compounds 1.1 through 1.56 described in Table T1 (below).

[0146] 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 (name IUPAC) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC name / Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N1-naphthylacetamide (IUPAC name) (1295) + TX, 4 - chlorophenylphenylsulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocil (3) + TX, acetoprol [CCN] + TX, acrinatrine (9) + TX, aldicarb (16) + TX, aldoxicarb (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, arsenous 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, buprofezin (99) + TX, butocarboxim (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, clordimeform ( 964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorophenetol (968) + TX, chlorophensone (970) + TX, chlorfensu lfeto (971) + TX, chlorfenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chlorometiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos -methyl (146) + TX, chlortiofos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (1010) + TX, cufranebe (1013) + TX, cyantoate (1020) + TX, kyphlumetophen (Reg. No.

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, dialiphos (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 (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [ CCN] + TX, endosulfan (294) + TX, endotion ( 1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, etion (309) + TX, ethoate-methyl (1134) + TX, ethoxazole (320) + TX, etrimphos (1142) + TX, phenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, 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, hexitiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbofos (alternative 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, mefosfolan (1261) + TX , messulfene (alternative name) [CCN] + TX, methacrifos (1266) + TX, metamidophos (527) + TX, metidation (529) + TX, metiocarb (530) + TX, methyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milb emicina oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (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, complex nitrilacarb 1: 1 zinc chloride (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamil (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,