BR112020000371A2 - 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

MICROBIOCIDAL OXADIAZOL DERIVATIVES

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

[0002] According to the present invention a compound of the formula (1) is provided: RR in the F R is: QD Z. nº RE RR (1)

[0003] where R !, R2, R3, Rº are independently selected from hydrogen or fluorine and where O, 1 or 2 from R !, R2, Rê and Rº are fluorine;

[0004] Rº and Rº are independently selected from hydrogen, C1.4 alkyl, C3.4 alkenyl or halogen;

[0005] Zz is selected from Z2 !, Zº or Z3; on what

[0006] Z! represents a heterocyclyl linked to C (R5) (Rº) through a CC bond, where the heterocyclyl fraction is a 5-membered non-aromatic ring that contains 1 nitrogen in the ring system and optionally comprises 1, 2 or 3 additional ring members independently selected from the group consisting of O, S, N, NRº, C (O0) or S (0)>, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S;

[0007] 7th? represents a heteroaryl linked to C (R5) (R9) through a CC bond, where the heteroaryl fraction is a 5-membered aromatic ring that contains 1 nitrogen atom in the ring system and optionally comprises 1, 2 or 3 ring members additional independently selected from the group consisting of O, S, N or NR;

[0008] R7 is hydrogen, C1.4 alkyl, C1.4 alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, alkylsulfonyl C14a, N-alkylaminosulfonyl or N, N-N-dialkylaminosulfonyl C1.2;

[0009] where for 2! and 7th, the heterocyclyl or heteroaryl fraction is: optionally substituted by 1, 2 or 3 substituents, which can be the same or different, selected from R8, or is substituted by 1 substituent selected from Rê and 1 substituent selected from phenyl or oxazolyl , or is replaced by 1 substituent selected from phenyl or oxazolyl;

[0010] Rê represents cyano, halogen, hydroxy, C1-1 alkyl, Cr4 alkenyl, C2r4 alkynyl, Cia cyanoalkyl, C1.4 haloalkyl, C2.4 haloalkyl, Cia alkoxy, C1-1 haloalkoxy, C3.4 alkenyloxy, C3 alkynyloxy -4, amino, C1-4 N-alkylamino, N, N1-4 C1-4alkylamino, C1-4alkylcarbonyl, C1-4alkoxycarbonylamino, C1-4alkylcarbonylamino, N- C1.4-alkylaminocarbonylamino, N, N-dialkylaminocarbonyl C1i4, C1.14 alkoxycarbonylamino, C2 N-alkenyl> -4-C2 aminocarbonyl. 4, N-alkynyl Cra-aminocarbonyl, N-furan-2-yl-methyl-aminocarbonyl, N-cycloalkylaminocarbonyl C3.6, N-alkoxy C1-2alkylaminocarbonyl C12, N-alkoxyminocarbonyl C14, phenylaminocarbonyl, phenylalkylaminocarbonyl Cia, N -aN-C1-α-aminocarbonyl alkyl, -C (0) OH, C1-4 alkoxycarbonylamino C1.2alkyl and N-morpholinocarbonyl;

[0011] Z3 represents a saturated, partially saturated or unsaturated 7 to 9-membered heterobicyclic ring system comprising a fragment: (i) a 5-membered non-aromatic ring containing 1 ring nitrogen or (ii) a 5-membered aromatic ring 1 ring nitrogen,

[0012] in which fragments (i) and (ii) are linked to C (R5) (R6º) through a CC link, and where the heterobicycle comprises - optionally 1 to 4 additional groups selected from O, S, N or NRº, with the proviso that the heterobicycle cannot contain 2 contiguous atoms selected from 0 eS and

[0013] where Z3 is optionally substituted by 1, 2 or 3 substituents, which can be the same or different, selected from R% º;

[0014] Rº is hydrogen, C1.4 alkyl, C1.4 alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, C14a alkylsulfonyl, N-alkylaminosulfonyl or N, N-N-dialkylaminosulfonyl C1.2; and

[0015] R! º represents cyano, halogen, hydroxy, C1-1 alkyl, C2r4 alkenyl, C2r4 alkynyl, C14 haloalkyl, C2.4 haloalkenyl, C1.4 alkoxy, C1.4 haloalkoxy, C3-1 alkenyloxy, C3 alkynyloxy. 4, N-alkylamino C1.4, N, N-dialkylamino C1-4, alkylcarbonyl C1-4, alkoxycarbonylamino C1-4, alkylcarbonylamino C1.4, N-alkylaminocarbonyl C141a, N, N-dialkylaminocarbonyl C1.4, alkoxycarbonylamino C1i4, N-cyclopropylaminocarbonyl and -C (0) OH;

[0016] or

[0017] a salt or N-oxide and

[0018] with the proviso that the compound of Formula (TI) is not 3- [4 - [(5,5-dimethyl-4H-oxazol-2-yl) methyl] phenyl] -5- (trifluoromethyl) -1 , 2,4-0xadiazole.

[0019] 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.

[0020] According to a second aspect of the invention, an agrochemical composition is provided 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.

[0021] According to a third aspect of the invention, a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms is provided, wherein a fungicidal effective amount of a compound of Formula (I), or a composition comprising this compound as an active ingredient, is applied to plants, parts of it or its locus.

[0022] 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.

[0023] As used here, the term "halogen" or "halo" refers to fluorine (fluorine), chlorine (chlorine), bromine (bromine) or iodine (iodine), preferably fluorine, chlorine or bromine.

[0024] As used here, acyl means a -C (0) CH3 group.

[0025] As used here, formyl means a group - C (O) H.

[0026] As used herein, the term "C1.4 alkyl" refers to a straight or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, containing no unsaturation, having one to four carbon atoms, and which is attached to the rest of the molecule by a single bond. C1.3 alkyl and C1.2 alkyl are to be interpreted accordingly. Examples of C1 alkyl include, but are not limited to, methyl, ethyl, n-propyl, l1- methylethyl (isopropyl), n-butyl and 1-dimethylethyl (t-butyl). A “C1.4" alkylene group refers to the corresponding definition of C1.4 alkyl, except that such a radical is attached to the rest of the molecule by two simple connections. Examples of C1.4 alkylene are -CH27- and -CH> CH> -

[0027] As used here, the term "C1.4 alkoxy" refers to a radical of the formula -ORas where Ra is a C1-4 alkyl radical as generally defined above. The terms C1.3 alkoxy and C1 alkoxy> 7 are to be interpreted accordingly Examples of C1.4 alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and t-butoxy.

[0028] As used herein, the term "C1.4 haloalkyl" refers to a C1.3 alkyl radical as generally defined above replaced by one or more the same or different halogen atoms. Examples of C1.4 haloalkyl include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.

[0029] As used herein, the term "C3.5 alkenyl" refers to a radical group of straight or branched hydrocarbon chains consisting merely of carbon and hydrogen atoms, containing at least one double bond that may have an (E) configuration or (Z), having three to five carbon atoms, which is attached to the rest of the molecule by a single bond. Examples of C3.5s alkenyl include, but are not limited to, prop-1-enyl, ally (prop- 2-enyl) and but- 1-enyl.

[0030] As used herein, the term "C3.5 alkenoxy" refers to a radical of the formula -ORs where Ra is a C3.5 alkenyl radical as generally defined above.

[0031] As used herein, the term "C3.4 alkynyl" refers to a radical group of straight or branched hydrocarbon chains consisting merely of carbon and hydrogen atoms, containing at least one triple bond, having three or four atoms carbon, and which is attached to the rest of the molecule by a single bond. Examples of Cr-6 alkynyl include, but are not limited to, prop-1-inyl, propargyl (prop-2-inyl).

[0032] As used herein, the term "C3.4 alkoxy" refers to a radical of the formula -OR. Where R. is a C3-4 alkynyl radical as generally defined above.

[0033] As used here, the term "C.1.4 alkoxy C1.4" "" refers to a radical of the formula Rr-O0-Ra- where Rv is a C1-4 alkyl radical as generally defined above, and Ra is a C1.4 alkylene radical as generally defined above.

[0034] As used here, the term "C3.5 cycloalkyl" refers to a stable, monocyclic ring radical that is saturated or partially unsaturated and contains 3 to 6 carbon atoms. C3.5 cycloalkyl and C3 cycloalkyl are to be interpreted Examples of C3-6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl and cyclohexen-3-yl.

[0035] As used herein, the term "C3-cycloalkyl C1-4alkyl" refers to a C3-6 cycloalkyl ring as defined above attached to the rest of the molecule by a C1-4 alkylene radical as defined above. Examples of C3 cycloalkyl-C13 salkyl include, but are not limited to, cyclopropyl-methyl and cyclobutyl-ethyl.

[0036] The presence of one or more possible asymmetric carbon atoms in a compound of the Formula (IT) means that the compounds can occur in chiral isomeric forms, i.e., enantiomeric or diastereoisomeric forms. Atropisomers can also occur as a result of restricted rotation around a single bond. Formula (I) 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 lactam tautomerism and keto enol tautomerism) where present. The present invention includes all possible tautomeric forms for a compound of Formula (1).

[0037] In each case, the compounds of Formula (1) according to the invention are in the free form, in the oxidized form as an N-oxide, in covalently hydrated form or in the form of salt, e.g. of agronomically usable or agrochemically acceptable salt.

[0038] N-oxides are oxidized forms of tertiary amines or oxidized forms of heteroaromatic compounds containing nitrogen. They are described for example in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0039] The following list provides definitions, including preferential definitions, for substituents Z (721, 7º and 73), RI, R2, R3, R1, Ró, R6, R7, R8, Rº and R! º with reference to the compounds of Formula (1) according to the invention. For any of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0040] R !, R2, R3, Rº are independently selected from hydrogen or fluorine, where O, 1 or 2 of R !, R2, Rà and Rº are fluorine.

[0041] In certain embodiments of the invention, Ri, R2, Rê and Rº are hydrogen; Rº, R3 and Rº are hydrogen and Rº! it is fluorine; Ri, Rº and Rº are hydrogen and Rê is fluorine; R! and R2 are fluorine and R and Rº are hydrogen; R! and R3 are fluorine and R2 and Rº are hydrogen, or R! and Rº are hydrogen and Ri and Rº are fluorine.

Preferably, R! the Rº are hydrogen.

[0042] Rº and Rº are independently selected from hydrogen, C14 alkyl (such as methyl, ethyl or isopropyl), C34 alkenyl or halogen (such as fluorine).

Preferably, Rs and Rº are both hydrogen, or R5 is hydrogen and Rº is methyl, or Rº is fluorine and Rº is methyl, Rº is fluorine and Rº is ethyl, Rs is fluorine and Ré is iso-propyl, or Rs and R6 are both fluorine. Most preferably, Rº and Rº are both hydrogen.

[0043] Zz is selected from 721, 722 or ZD3.

[0044] In certain embodiments of the invention, Z is Zl.

[0045] In certain embodiments of the invention, 2 is Z '.

[0046] In certain embodiments of the invention, 2 is Z3.

[0047] Z! represents a heterocyclyl linked to C (R5) (R $)

through a CC bond, where the heterocyclyl fraction is a 5-membered non-aromatic ring that contains 1 nitrogen in the ring system and optionally comprises 1, 2 or 3 additional ring members (and preferably optionally 1 additional ring member) independently selected from group consisting of O, S, N, NR ”, C (O0) or S (0) 2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S.

[0048] According to the invention, the compound of Formula (1) is not 3- [4 - [(5,5-dimethyl-4H-oxazol-2-yl) methyl] phenyl] -5- (trifluoromethyl) - 1,2,4-0xadiazole.

NO F [| Cr

N N F AILIS HJ; THE

[0049] 7º represents a heteroaryl linked to C (R5) (Rº) through a CC bond, in which the heteroaryl fraction is a 5-membered aromatic ring that contains 1 nitrogen atom in the ring system and optionally comprises 1, 2 or 3 additional ring members (and preferably optionally 1 or 2 additional ring members) independently selected from the group consisting of O, S, N or NR ”.

[0050] To 72! and 7, the heterocyclyl or heteroaryl fraction is: optionally substituted by 1, 2 or 3 substituents (or optionally substituted by 1 or 2 substituents or optionally substituted by 1 substituent), which can be the same or different, selected from R8, or it is replaced by 1 substituent selected from Rê and 1 substituent selected from phenyl or oxazolyl (including oxazol-2-yl) or is replaced by 1 substituent selected from phenyl or oxazolyl (including oxazol-2-yl);

[0051] Preferably 2! It's

[0052] optionally substituted by 1 or 2 substituents, which can be the same or different, selected from Rº.

[0053] Preferably, 722 is

R

AR IS DR LR e and Oe TE de

[0054] optionally substituted by 1 or 2 substituents, which can be the same or different, selected from Rº.

[0055] Z3 represents a fused, partially saturated or unsaturated 7 to 9-membered heterobicyclic ring system comprising a fragment:

[0056] a 5-membered non-aromatic ring containing 1 ring nitrogen or

[0057] an aromatic ring with 5 members containing 1 ring nitrogen,

[0058] in which fragments (i) and (ii) are linked to C (R5) (R6º) through a CC bond, and where the heterobicycle comprises - optionally 1 to 4 additional groups selected from O, S, N or NRº, with the proviso that the heterobicycle cannot contain 2 contiguous atoms selected from 0 eS and

[0059] where Z3 is optionally substituted by 1, 2 or 3 substituents, which can be the same or different, selected from R% ºº.

[0060] Z3 can be a 7-membered heterobicyclic ring system. Z3 can be an 8-membered heterobicyclic ring system. Z3 can be a 9-membered heterobicyclic ring system.

[0061] Z73 can optionally comprise 1 to 3 additional groups selected from O, S, N or NRº. Z3 can optionally comprise 1 or 2 additional groups selected from O, S, N or NRº. Z3 can optionally comprise 1 additional group selected from O, S, N or NRº.

[0062] Preferably, Z3 is AX Os Os TC) Ade and

[0063] optionally “substituted with 1, 2 or 3 substituents, which can be the same or different, selected from R% ºº.

[0064] R7 is hydrogen, C1.4 alkyl, C1.4 alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, alkylsulfonyl C14a, N-alkylaminosulfonyl or N, N-dialkylaminosulfonyl C1.2.

[0065] Preferably, Rº is hydrogen, C1-4 alkyl, C1-4 alkoxy, formyl or C1-6 alkylcarbonyl. More preferably, R7 is hydrogen, methyl or formyl, in particular, hydrogen.

[0066] Rê represents cyano, halogen, hydroxy, C1-1 alkyl, Cr4 alkenyl, C2r4 alkynyl, Cia cyanoalkyl, C1.4 haloalkyl, C2.4 haloalkyl, Cia alkoxy, C1-1 haloalkoxy, C3.4 alkenyloxy, C3 alkynyloxy -4, amino, C1-4 N-alkylamino, N, N1-4 C1-4alkylamino, C1-4alkylcarbonyl, C1-4alkoxycarbonylamino, C1-4alkylcarbonylamino, N- C1.4-alkylaminocarbonylamino, N, N-dialkylaminocarbonyl C1i4, C1-4 alkoxycarbonylamino, N> C-alkenyl .4-aminocarbonyl, N-C2-a-aminocarbonyl, N-furan-2-yl-methyl-aminocarbonyl, N-cycloalkylaminocarbonyl C3.6, N-C1-2alkylaminocarbonyl C12 , N-alkoxycarbonyl C14, phenylaminocarbonyl, phenylalkylaminocarbonyl Cia, N-C1-aN-alkoxy C1-a-aminocarbonyl, -C (0) OH,

alkoxycarbonylamino Ci.4alkyl C1.2 and N-morpholinocarbonyl.

[0067] Preferably, R8 is cyano, halogen, hydroxy, C1.4 alkyl, C> r4 alkenyl, Cr.4 alkynyl, C1-4 cyanoalkyl, Cia haloalkyl, amino, N-alkylamino Cias, N, N-dialkylamino C1.4, C1.4 alkylcarbonyl, C1 alkoxycarbonyl. 4a, N-alkylaminocarbonyl C1.4 or N, N-dialkylaminocarbonyl Cia. More preferably, Rê is hydroxy, C14 alkyl, C1-14 cyanoalkyl, C1.4 haloalkyl, amino, C1-4 alkylamino, N, N-dialkylamino C1-4, C1-4 alkylcarbonyl, C1.4 alkoxycarbonyl, C14 N-alkylaminocarbonyl or C1-4 N, N-dialkylaminocarbonyl. Even more preferably, Rê is hydroxy, C1.4 alkyl, C1.2 cyanoalkyl, C1 fluoroalkyl. 2, amino, C12 N-alkylamino, N, C12 N-dialguylamino, C1-2 alkylcarbonyl, C1-2 alkoxycarbonyl, C1.2 N-alkylaminocarbonyl or N, N-N-dialkylaminocarbonyl C1.2.

[0068] Rº is hydrogen, C1.4 alkyl, C1.4 alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, alkylsulfonyl C14a, N-alkylaminosulfonyl or N, N-dialkylaminosulfonyl C1.2.

[0069] Preferably, Rº is hydrogen, C1-4 alkyl, Coxy alkoxy, formyl or Ciaalkylcarbonyl. More preferably, Rº is hydrogen, methyl or formyl, in particular, hydrogen.

[0070] R! º represents cyan, halogen, hydroxy, alkyl

C1-1, C2r4 alkenyl, C2r4 alkynyl, C14 haloalkyl, C2.4 haloalkenyl, C1.4 alkoxy, C1.4 haloalkoxy, C3-1 alkenyloxy, C3.4 alkynyloxy, C1.4 N-alkylamino, N, N-dialkylamino C1-4, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, C1.4 alkylcarbonylamino, C141a N-alkylaminocarbonyl C1.4, N-dialkylaminocarbonyl C1.4, C1i4 alkoxycarbonylamino and -C (0) OH.

[0071] Preferably, R! º is cyano, halogen, hydroxy, C1 alkyl, Cr4 alkenyl, C2a4 alkynyl, C1 fluoroalkyl> 2, C21 haloalkenyl, Cia alkoxy, C24 fluoroalkoxy, C34 alkenyloxy, C34 alkynyloxy, C-alkylamino. 2, N, N-dialkylamino C1.2, C1 alkylcarbonyl. 2) C1> 2 alkoxycarbonyl, 2-alkylcarbonylamino —C1.2, N-C1-2 alkylaminocarbonyl, N, N-dialkylaminocarbonyl C1.2 or C1.2 alkoxycarbonylamino.

[0072] Preferably, the compound according to Formula (1) is selected from compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) ) and compounds C.1 to C.8 described in Table C (below).

[0073] The compounds of the present invention can be enantiomers of the compound of Formula (TI) as represented by a Formula (Ta) or a Formula (Ib), where Rº and R6 are different substituents.

KR in F Rê in F to RR as R

RR RR RW RR (Ta) (Ib)

[0074] It is understood that, when in aqueous media, the compounds of the formula (1) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (ie, the compounds of the formula (I-Ia) and formula (I-IIa) as shown below, which can exist in tautomeric form as the compounds of formula (I-Ib) and formula (I-IIb)) in the CF3-oxadiazole motif). This dynamic balance can be important for the biological activity of the compounds of the Formula (TI). The designations Z (721, 72 and Z3), R1, R2, R3, R4, R5, R6, R7, Rê, Rº and R! º with reference to the compounds of the formula (1) of the present invention generally apply to the compounds of Formula (I-Ia), Formula (I-IIa), Formula (I-Ib) and Formula (I-IIb), as well as specific disclosures for combinations of Z (21, 22 and Z3), R1, R2, R3 , R4, R5, R6, R7, R8, Rº and R! º as shown for compounds T-2.01 to T-2.35 to T-23.01 to T-23.35 shown in Tables 2 to 23 (below) and compounds A. l1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below).

Ro NO F Fr. RAQAT |

2. FA XK, Tt * & é 2 0) -Ho 1 sms h nd neo É R nº / F * A Fo AD SE our + z RA a e Ne É> RR and RR RR (Ha) (Hia)! theater || tautomerization | | h a F R ne RANA dr 1 p—— R AA PS À Nor F +) a AL e É SS SE 2

RR RR ER E (Hb) (Hib)

[0075] The compounds of the present invention can be prepared as shown in the following schemes 1 to 10, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (1).

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

K2C03, CsXC0; z or NaH) in a suitable solvent (eg, dimethylformamide or tetrahydrofuran) at a temperature between 25 ºC and 110 ºC. In some cases, a better reaction performance can be gained by using a catalyst (eg, NaI or 4-dimethylaminopyridine) and with microwave irradiation. For related examples see: WO 2013/132253 and Garcia, M. et al. Org. Biomol. Chem. (2004), 11, 1633. This reaction is shown in Scheme 1. RR —o F 3 o F x Re + ZH -> Z ”RR RR 0) (1) RR OR Scheme 1

[0077] In addition, compounds of formula (1), where preferably n is 1, can be prepared from compounds of formula (IV) by treatment with trifluoroacetic anhydride in the presence of a base (e.g., pyridine or 4-dimethylaminopyridine) in a suitable solvent, such as tetrahydrofuran or ethanol, at a temperature between 25 ºC and 75 ºC. For related examples see WO 2003/028729 and WO 2010/045251. This reaction is shown in Scheme 2.

3 —OH

R N RR NO F à nº |! 1 ? R N F Z 4 a R Zz a Ré Rê 2 so R

RW RR (V) (O) Diagram 2

[0078] The compounds of formula (IV) can be prepared from compounds of formula (V) by treatment with a hydroxylamine hydrochloride in the presence of a base, such as triethylamine, in a suitable solvent, such as methanol, at a temperature between 0 ºC and 100 ºC. For related examples see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268 and WO 2013/066838. This reaction is shown in Scheme 3. 8 R 3 oH

N R N Rº Gr Rº

NH? RR Z RR S 6 2 RR R EX Re (V) (IV) Figure 3

[0079] The compounds of the formula (V) can be prepared from compounds of the formula (VI), where Y is Br or I, through reaction promoted by metals with a suitable cyanide reagent, such as Pd (0) / ZnN (CN), or CUuCN, in a suitable solvent (eg, dimethylformamide or N-

methylpyrrolidone) at an elevated temperature between 100 ºC and 120 ºC. For related examples see US 2007/0155739 and WO 2009/022746. This reaction is shown in Scheme 4.

RR 1 R N R Y Rº Jr Z 4 R —— Z. 4 RR Rô 2 R R R Re Re (1) (V) Diagram 4

[0080] The compounds of the formula (VI), where preferably n is 1, can be prepared from compounds of the formula (VII), where X is a halogen, preferably Cl, Br or IL, through treatment with compounds of formula (III), in the presence of a base (eg, K2C03, CsXC0; z or NaH) in a suitable solvent (eg, dimethylformamide or tetrahydrofuran) at a temperature between 25 ºC and 110 ºC . In some cases, a better reaction performance can be obtained by using a catalyst (eg, NaI or 4-dimethylaminopyridine) and with microwave irradiation. For related examples see: WO 2013/132253 and Garcia, M. et al. Org. Biomol. Chem. (2004), 11, 1633. This reaction is shown in Scheme 5.

RR Rê and SE Z — H + ——-—-—-— X. Rº Z. nº

RR RR RR RX (D) (VI) (VV) Figure 5

[0081] The compounds of the formula (II), where ne le X is Cl or Br, can be prepared from compounds of the formula (VIII), by treatment with a halogen source (eg, N-bromosuccimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator (eg, (PhCO2), or azobisisobutyronitrile (AIBN)) in a suitable solvent, such as tetrachloromethane, at temperatures between 55 º and 100 ºC in the presence of ultraviolet light. For related examples see Liu, S. et al. Synthesis (2001), 14, 2078 and Kompella, A. et al. Org. Proc. Res. Dev. (2012), 16, 1794. This reaction is shown in Scheme 6. RR or RR NO F

F R F Rº DT H Rº x Ré RR Re Rós 2 (VI) (1) Diagram 6

[0082] Alternatively, compounds of formula (II) can be prepared from compounds of formula (IX)

by treatment with trifluoroacetic anhydride in the presence of a base (for example, pyridine or 4-dimethylaminopyridine) in a suitable solvent, such as tetrahydrofuran or ethanol, at a temperature between 25 ºC and 75 ºC. For related examples see WO 2003/028729 and WO 2010/045251. This reaction is shown in Scheme 7. Ro NO "R NO F Rº NH, Rº | ZA! -. X RR x RR

RR RR RR () (1) Figure 7

[0083] The compounds of formula (IX) can be prepared from compounds of formula (X) by treatment with a hydroxylamine hydrochloride salt in the presence of a base, such as triethylamine, in a suitable solvent, such as methanol, at a temperature between 0 ºC and 100 ºC. For related examples see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268 and WO 2013/066838. This reaction is shown in Scheme 8.

R RR NOW

N R R R NH, x R to OX R R x Rê R Re Rn x) (IX)

Layout 8

[0084] The compounds of the formula (VII), where Y is Br, IT or CNexXéCcCl, Br or Tl, are commercially available or can be prepared from compounds of the formula (XI), by treatment with a halogen source ( eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator, such as (PhCO02) 2 or azobisisobutyronitrile (AIBN), in the presence of ultraviolet light, in a suitable solvent, such as tetrachloromethane, at temperatures between 55 ºC and 100 ºC. For related examples see Liu, S. et al. Synthesis (2001) 14, 2078 and Kompella, A. et al. Org. Proc. Res. Dev. (2012), 16, 1794. This reaction is shown in Scheme 9.

R R —— = á R * Rº RR ks PR RR 4S RR (XI) (VI) Figure 9

Alternatively, compounds of formula (VII), where n is 1 and X is Cl, Br, I or 0SO0XMe and Y is Br, IT or CN, are commercially available or can be prepared from compounds of the formula (XII), by treatment with a halogen source (eg, CCl3Br, CCla or I2) in the presence of triphenylphosphine, or with methanesulfonyl chloride

(C1S02Me), in a suitable solvent (eg, dichloromethane) at a temperature between 0 ºC and 100 ºC. For related examples see Liu, H. et al. Bioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A. et al. Bioorg. Med. Chem. Lett. (2001), 1, 3161. The compounds of the formula (XII) are commercially available. This reaction is shown in Scheme 10. 3 Rº À Y 1 F

R Y Nos Do R Rô Rê Ré kS Re (XI) (VI) Diagram 10

[0086] As already indicated, surprisingly, it has now been discovered that the compounds of Formula (I) of the present invention have, for practical purposes, a very advantageous level of biological activity to protect plants against diseases that are caused by fungi.

[0087] The compounds of Formula (1) can be used in the agricultural sector and related areas of use, eg as active ingredients to control plant pests or in non-living materials to control microorganisms that cause deterioration or potentially harmful organisms to the man. The new compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants and by being environmentally safe. They have very useful healing, preventive and systemic properties and can be used to protect 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, flowers, leaves, stems, tubers, roots) from different crops of useful plants, while at the same time also protecting those parts of plants that grow later, eg from phytopathogenic microorganisms.

[0088] The present invention additionally relates to a method to control or prevent infestation of plants or plant propagating material and / or collected food crops susceptible to microbial attack by treating plants or plant propagating material and / or food crops collected in which an effective amount of a compound of Formula (1) is applied to plants, their parts or their locus.

[0089] It is also possible to use compounds of Formula (TI) 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" where used means the amount of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. The effects of controlling or modifying 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.

[0090] It may also be possible to use compounds of Formula (1) as covering agents for the treatment of plant propagating material, eg, seed, such as fruits, tubers or grains, or plant cuttings, for the 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: the 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 to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention also relates to such methods of treating plant propagation material and to the plant propagation material so treated.

[0091] Furthermore, the compounds of the Formula (TI) 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.

[0092] Additionally, the invention could be used to protect non-living materials from fungal attack, eg, construction wood, wall panels and paint.

[0093] The compounds of the Formula (TI) 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:

[0094] Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora Spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F.

OXysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporiisto spp, Hemp 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 PP. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas SPpp, 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 Sspp. 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 sporunm, Storospora sp. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

[0095] The compounds of Formula (1) can be used for example in peat, ornamental plants such as flowers, shrubs, trees with broad or perennial leaves, for example conifers, as well as for tree injection, pest management and the like .

[0096] Within the scope of the present invention, target crops and / or useful plants to be protected typically comprise perennial and annual crops, such as berries, for example blackberries, blueberries, cranberries, raspberries and strawberries;

cereals, for example barley, maize (maize), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar beet and fodder, coffee, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, for example Bermuda grass, blue grass, agrostis, centipede grass, fescue, ryegrass, Saint Augustine grass and Zoysia grass; aromatic herbs such as basil, borage, chives, coriander, lavender, levistico, mint, oregano, parsley, rosemary, sage and thyme; legumes, for example beans, lentils, peas and soy; dried fruits, for example almond, cashew, peanut seed, hazelnut, peanut, pecan, pistachio and walnut; palms, for example palm oil; ornamental plants, for example flowers, shrubs and trees; other trees, for example cocoa, coconut, olive and rubber; “vegetable products, for example asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, baby pumpkin, rhubarb, spinach and tomato; and vines, for example grapes.

[0097] The term "useful plants" is to 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, eg primisulfurone, prosulfurone and trifloxysulfurone, EPSPS inhibitors (5-enol-pyrovil-chiquimate-3-phosphate synthase), GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional methods of breeding or genetic manipulation. An example of a crop that has been made tolerant to imidazolinones, eg imazamox, by conventional breeding methods (mutagenesis) is the Clearfieldº summer rape (Canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic manipulation methods include varieties of glyphosate and glufosinate resistant maize, commercially available under the trademarks RoundupReadyº, Herculex IT and LibertyLinkº.

[0098] The term "useful plants" is to be understood as also including useful plants that have been so transformed by the use of recombinant DNA techniques that they are able to synthesize one or more selectively active toxins, such as are known, for example, to from bacteria that produce toxins, especially those of the Bacillus genus.

[0099] Examples of such plants are: YieldGard (variety of apples that expresses a CryIA toxin (b)); YieldGard Rootworm (variety of maize that expresses a CryIIIB toxin (b1)); YieldGard Plus (more variety that expresses a CryIA toxin (b) and a CryIIIB toxin (bl1)); Starlink (more variety that expresses a Cry9 toxin (c)); Herculex I (variety of maize that expresses a CryIF toxin (a2) and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B (cotton variety that expresses a CryIA (c) toxin); Bollgard 1 (cotton variety that expresses a CryIA toxin (c)); Bollgard IIº (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); NatureGard Agrisureº GT Advantage (glyphosate tolerant trait GA21), Agrisureº CB Advantage (trait of corn borer (CB) Bt11), Agrisureº RW (trait of corn rootworm) and Protecta

[00100] The term "cultures" is to be understood as also including culture plants that have been so transformed by the use of recombinant DNA techniques that they are able to synthesize one or more selectively active toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[00101] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from

Bacillus cereus or Bacillus popilliae; or Bacillus thuringiensis insecticidal proteins, such as 6 endotoxins, e.g., CrylAb, CrylAc, Cryl1F, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (Vip), eg, Vipl, Vip2, Vip3 or Vip3A; or insecticidal proteins from nematode colonizing bacteria, for example Photorhabdus spp., or Xenorhabdus Sspp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect specific neurotoxins; toxins produced by fungi, such as Streptomyces toxins, plant lectins, such as pea lectins, barley lectins, or white bell lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, corn RIP, abrina, lufina, saporina or briodina; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[00102] Additionally, in the context of the present invention, they are to be understood as 65-endotoxins, 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 are known, for example a truncated CrylAb. In the case of modified toxins, one or more naturally occurring toxin amino acids are replaced. In such amino acid substitutions, preferably non-naturally occurring protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin G recognition sequence is inserted into a Cry3A toxin (see WO 03/018810 ).

[00103] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-AO 374 753, W093 / 07278, WO95 / 34656, EP-AO 427 529, EP-A-451 878 and WO 05/032073.

[00104] 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.

[00105] The toxin contained in transgenic plants gives plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), double-winged insects (Diptera) and butterflies (Lepidoptera).

[00106] Transgenic plants are known to contain one or more genes that encode an insecticidal resistance and express one or more toxins and some of them are commercially available. Examples of such plants are: YieldGard (variety of maize that expresses a Cryl1Ab toxin); YieldGard Rootworm (more variety that expresses a Cry3Bb1 toxin); YieldGard Plus (variety of apples that expresses a CrylAb toxin and a Cry3Bbl); Starlink (more variety that expresses a Cry9C toxin); Herculex I (variety of maize that expresses a CrylFa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NUCOTN 33B (cotton variety that expresses a Cryl1Ac toxin); Bollgard IT (cotton variety that expresses a CrylAc toxin); Bollgard IIº (cotton variety that expresses a CrylAc toxin and a Cry2Ab); VipCot (cotton variety that expresses a Vip3A toxin and a CrylAb); NewLeaf (potato variety that expresses a Cry3A toxin); NatureGard, Agrisureº GT Advantage (glyphosate tolerant trait GA21), Agrisureº CB Advantage (trait tolerant to corn borer (CB) Bt11) and Protecta. Additional examples of such transgenic crops are:

[00107] Maís Bt11 from Syngenta Seeds SAS, Chemin de 1 Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. More Bt11 also expresses the PAT enzyme transgenically to achieve tolerance to the herbicide glufosinate ammonium.

[00108] Maís Bt176 from Syngenta Seeds SAS, Chemin de 1 Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96/05/10. Genetically modified Zea mays that has been made resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. More Bt1l76 also expresses - transgenically the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium.

[00109] More MIRG604 from Syngenta Seeds SAS, Chemin 1 Hobit 27, F-31 790 St. Sauveur, France, registration number

C / FR / 96/05/10. More that has been made resistant to insects by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by inserting a cathepsin G protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

[00110] Maís 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.

[00111] Cotton IPC 531 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96/02.

[00112] More 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00/10. More genetically modified for the expression of the CrylF protein to achieve resistance to certain Lepidoptera insects and the PAT protein to achieve tolerance to the herbicide glufosinate ammonium.

[00113] Maís NK603 x MON 810 from Monsanto Europe S.A. 270- 272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of hybrid maize varieties conventionally improved by crossing the genetically modified varieties NK603 and MON 810. Maís NK603 x MON 810 transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium Sp.,

which gives tolerance to the herbicide Roundupº (contains glyphosate), and also a toxin CrylAb obtained from Bacillus thuringiensis subsp. kurstaki that confers tolerance to certain Lepidotera, including the European corn borer.

[00114] The compounds of Formula (1) (including any of compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below)) in accordance with the present invention can be used in the control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

[00115] In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, e.g., CrylAc (protein CrylAc Bt). Accordingly, this may include transgenic soybean plants comprising the MON87701 event (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 Al (eg, see paragraph [008], reference to Intact soy) RR2 PRO "M)), event MON87751 (U.S. Patent Application Publication No. 2014/0373191) or DAS-81419 event (U.S. Patent No. 8632978 and related applications and patents).

[00116] Other transgenic soybean plants may comprise the SYHTOH2 event - tolerance to HPPD (U.S. Patent Application Publication

No. 2014/0201860 and related orders and patents), event MON89788 - glyphosate tolerance (U.S. Pat.

No. 7,632,985 and related patents and orders), event MON87708 - dicamba tolerance (U.S. Patent Application Publication

At the.

US 2011/0067134 and related orders and patents), event DP- 356043-5 - glyphosate tolerance and ALS (U.S. Patent Application Publication

At the.

US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (U.S. Patent Application Publication

At the.

US 2008/0320616 and related orders and patents), event DP-305423-1 - tolerance to ALS (U.S. Patent Application Publication

At the.

US 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolerance (U.S. Patent Application Publication

At the.

US 2008/0196127 and related applications and patents), event DAS- 40278-9 - tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011/022469, WO 2011/022470, WO 2011/022471 and related applications and patents) , event 127 - tolerance to ALS (WO 2010/080829 and related orders and patents), event GTS 40-3-2 - tolerance to glyphosate, event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, event FG72 - tolerance to glyphosate and isoxaflutole, event BPS-CV127-9 - tolerance to ALS and GU262 - tolerance to glufosinate or event SYHTO4R - tolerance to HPPD.

[00117] 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 plants transgenic soybeans as described above), may exhibit a synergistic interaction between the active ingredients.

[00118] Additionally, to date, no cross-resistance has been observed between the compounds of Formula (TI) (including any of compounds A.1 to A.60 described in Table A (below), compounds B.1 to B .30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below)) and the current fungicide solutions used to control Phakopsora pachyrhizi.

[00119] In fact, fungal 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: steroid demethylation inhibitors (DMI) , external quinone (QoI) inhibitors and succinate dehydrogenase (SDHI) inhibitors. See for example: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors,

and corresponding resistance mechanisms ”. Schmitz HK et al., Pest Manag Sci (2014) 70: 378-388; “First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhyizi" 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.

[00120] Thus, in a preferred embodiment, the compounds of Formula (1) (including any of compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below)), or fungicidal compositions according to the present invention comprising a compound of Formula (TI), are used to control Phakopsora pachyrhizi which are resistant to one or more fungicides of any of the following classes of MoA fungicides: sterol demethylation inhibitors (DMI), external quinoa inhibitors (QoI) and succinate dehydrogenase inhibitors (SDHI).

[00121] The compounds of Formula (1) (including any of compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (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 cells of the R gene, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, were introgressed in the plant's genome, see for example: “Fighting Asian Soybean Rust" , Langenbach C, et al., Front Plant Science 7 (797) 2016).

[00122] An elite plant is any plant in an elite line, such that an elite plant is a plant representative of an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to soybean farmers or breeders include: AGOO8O2, AOSG8, AGO9N2, Al923, AG2403, A2824, A3704, A4324, A5404, AG5903, AGG6202 AGO934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AGG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPRO144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, Ill., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex.,

USA); JG O03R501, 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, POOST22R2; PI6TI17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T721R; and P56TO03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG477I1NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Ind., USA); SOO-K5, S11-L2, S28-Y2, S43-B1, S53-Al, S76-L9, S78-G6, SOPOI-M2; SOO7-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; S58-24; 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).

Thus, in an additional preferred embodiment, the compounds of Formula (TI) (including any of the compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below)), or fungicidal compositions according to the present invention comprising a compound of Formula (TI), are used to control Phakopsora pachyrhizi ( including their fungicide-resistant strains, as outlined above) in varieties of Elite soy plants where R gene cells, conferring a degree of immunity or resistance to

Phakopsora pachyrhizi specific, were introgressed in the plant genome. Numerous benefits can be expected to follow from such use, eg 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 longer-lasting residual activity, a reduction in the number of applications and / or a reduction in the rate of application of compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thus allowing for beneficial resistance management practices, reduced environmental impact and reduced operator exposure.

[00124] The term "locus" as used here means fields in or on which plants are grown 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.

[00125] The term "plants" refers to all the physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stems, foliage and fruits.

[00126] The term "plant propagation material" is understood to denote generative parts of the plant, such as seeds, that can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Germinated plants and young plants that are to be transplanted after germination or after emergence from the soil can also be mentioned. These young plants can be protected before transplantation by total or partial immersion treatment. Preferably, "plant propagation material" is understood to denote seeds.

[00127] The compounds of Formula (II) 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, e.g., in polymeric substances. As with the type of compositions, the application methods, such as spraying, atomizing, dusty, dispersing, coating or spilling, are chosen according to the intended objectives and the prevailing circumstances. The compositions may also contain additional adjuvants such as stabilizers, defoamers, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations to obtain special effects.

[00128] Suitable carriers and adjuvants, eg for agricultural use, can be solid or liquid and are useful substances in formulation technology, eg natural or regenerated mineral substances, solvents, dispersants, wetting agents, stickiness promoters, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.

[00129] 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.

[00130] Wettable powders are in the form of finely divided particles that readily disperse in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include Fuller earth, kaolin clays, silica and other readily moist organic or inorganic solids. Wettable powders typically contain 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[00131] 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.

[00132] Granular formulations include both extruded and relatively coarse particles and are usually applied without dilution in the region where treatment is desired. 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.

[00133] Dusts are mixtures by free flowing addition of the active ingredient with finely divided solids such as talc, clays, flours and other organic or inorganic solids that act as dispersants and carriers.

[00134] Microcapsules are typically droplets or granules of the active ingredient encased in an inert porous shell that allows the escaped 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 may 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 1 centimeter and preferably from 1 to 2 millimeters in diameter. The granules are formed by extrusion, agglomeration or pearlization or occur naturally. Examples of such materials are vermiculite, sintered clay, kaolin, atapulgite clay, sawdust and granular coal. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthate.

[00135] Other formulations useful for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble in the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprayers, in which the active ingredient is dispersed in finely divided form as a result of the vaporization of a dispersing solvent carrier with a low boiling point, can also be used.

[00136] 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.

[00137] 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 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, 1-ethylene hexanol , 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, triacet glycerol, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, iso-octane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl islamethyl acetate, methyl islamethyl acetone, methyl islamethyl acetone methyl, 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, high molecular weight alcohols, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for diluting concentrates.

[00138] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, atapulgite clay, Kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller earth, bark cottonseeds, wheat flour, soy flour, pumice stone, wood flour, nutshell flour and lignin.

[00139] A wide range of surfactants is advantageously employed in both 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 ethoxylate C 18g-nonylphenol ethoxylate; products of the addition of alkylene alcohol-oxide, such as C 16 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.

[00140] 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.

[00141] In addition, 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.

[00142] The pesticide agents referred to here using their common name are known, for example, from “The Pesticide Manual", 15th Ed. British Crop Protection Council

2009.

[00143] 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 in, for example, United States Patent No. US 6,919,298 and include, for example,

salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[00144] 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, which influence plant growth. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired in conjunction with additional carriers, surfactants or application-promoting adjuvants commonly employed in the formulation technique.

[00145] 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 (I) or at least one preferred individual compound as defined here, in the free form or in the form of agro-chemically usable salt, and at least one of the aforementioned adjuvants.

[00146] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one Formula (II) compound, 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).

[00147] The compound of Formula (1) can be the only active ingredient of a composition or it can be mixed by addition with one or more additional active ingredients such as a pesticide, fungicide, synergistic agent, herbicide or plant growth regulator where appropriate. An additional active ingredient can, in some cases, result in unexpected synergistic activities.

[00148] 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, benzamide fungicides, , benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, diphenyl bridged fungicides, carbamate fungicides, carbanylate fungicides, conazole fungicides, copper fungicides,

dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolan fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, fungicides, oregano fungicides -in, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxalin fungicides, strobilurin, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, uzine fungicides and urea fungicides.

[00149] 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-yl) -amide -1-methyl-11H-pyrazol-4-carboxylic, methoxy- [1-methyl-2- (2,4,6-trichlorophenyl) -ethyl] -amide of 3-difluoromethyl-11-methyl-11H-pyrazole- Acid 4-carboxylic, (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl) -amide

1-methyl-3-difluoromethyl-1H-pyrazol-4-carboxylic (1072957- 71-1), 1-methyl-3-difluoromethyl-1H-pyrazole (4'-methylsulfanyl-biphenyl-2-yl) -amide -4-carboxylic acid, [2- (2,4-dichloro-phenyl) -2-methoxy-1-methyl-ethyl] 1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid, ( 5-Chloro-2,4-dimethyl-pyridin-3-yl) - (2,3,4-trimethoxy-6-methyl-phenyl) - methanone, (5-Bromo-4-chloro-2-methoxy-pyridin- 3-yl) - (2,3,4-trimethoxy-6-methyl-phenyl) -methanone, 2-12 - [(E) -3- (2,6-Dichloro-phenyl) -l-methyl-prop- 2-en- (E) -ylideneamino- oxymethyl] -phenyl) -2 - [(Z) -methoxy-imino] -N-methyl-acetamide, 3- [5- (4-Chloro-phenyl) -2,3 -dimethyl-isoxazolidin-3-yl] -pyridine, (E) -N-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxy-iminoacetamide, 4-bromo-2-cyano-N , N-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide, a- [N- (3-chloro-2,6-xylyl) -2-methoxyacetamido] - i-butyrolactone, 4-chloro-2-cyano-N, N -dimethyl-5-p-tolylimidazole-1-sulfonamide, N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide, N- (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-triazole-1 -yl) -cycloheptanol, 2- (1-tert-butyl) -1- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) - propan-2-ol, 2 ' , 6 '-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazol-5-carboxanilide, 1-imidazolyl-l- (4' -chlorophenoxy) -3,3-dimethylbutan-2- one, methyl (E) -2- [2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl] 3-methoxyacrylate, (E) -2- [2- [6- (2-thioamidophenoxy) methyl pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2- [2- [6- (2-fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, (E) -2 - [2- [6- (2,6-difluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] methyl phenyl] -3-methoxyacrylate, (E) -2- [2- [3- (5-methylpyrimidin-2-yloxy) -phenoxy] phenyl] -3-methyl methoxyacrylate, (E) -2- [2 - methyl [3- (phenylsulfonyloxy) phenoxy] phenyl-3-methoxyacrylate, (E) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate methyl, methyl (E) -2- [2-phenoxyphenyl] -3-methoxyacrylate, methyl (E) -2- [2- (3,5-dimethyl-benzoyl) pyrrol-1-yl] -3-methoxyacrylate , Methyl (E) -2- [2- (3-methoxyphenoxy) phenyl] -3-methoxyacrylate, (E) -2 [2- (2-phenylethen-1-1yl) -phenyl] -3-methoxyacrylate , (E) -2- [2- (3,5-dichlorophenoxy) pyridin-3-yl] -3-methyl methoxyacrylate, (E) -2- (2- (3- (1,1,2,2 methyl-tetrafluoroethoxy) phenoxy) phenyl) -3- methoxyacrylate, (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methyl-methoxyacrylate, (E) -2- ( Methyl 2- (4-phenoxypyridin-2-yloxy) phenyl) -3-methoxyacrylate, (E) -2- [2- (3-n-propyloxy-phenoxy) phenyl] 3-methyl methoxyacrylate, (E) - Methyl 2- [2- (3- isopropyloxyphenoxy) phenyl] -3-methoxyacrylate, (E) - 2- [2- [3- (2- fluorophenoxy) phenoxy] phenyl] -3-methoxyacrylate - methyl, (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-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) phenyl] -3-methyl methoxyacrylate, (E) - 2-12- [6- (6- methylpyridin-2-yloxy) pyrimidin-4-yloxy] phenyl) -3-methyl methoxy-acrylate, (E), (E) -2-f 2- (3-methoxyphenyl) methyloximinomethyl] -phenyl) -3-methoxyacrylate methyl, (E) -2-12- (6- (2-azidophenoxy) -pyrimidin-4-yloxy] phenyl) -3-methyl methoxyacrylate, (E), (E) -2-12- [6- methyl phenylpyrimidin-4-1yl) -methyloximinomethyl] -phenyl) -3-methoxyacrylate, (E), (E) -2-12 - [(4-chlorophenyl) - methyloximinomethyl] -phenyl) -3-methoxyacrylate, ( E) - 2-12- [6- (2-n-propylphenoxy) -1,3,5-triazin-4-yloxy] phenyl ); - methyl 3-methoxyacrylate, (E), (E) -2-12 - [(3-nitrophenyl) methyloximinomethyl] phenyl) -3-methylmethoxyacrylate, 3-chloro-7- (2-aza-2 , 7,7-trimethyl-oct-3-en-5 -ine), 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, alcohol

3-iodo-2-propynyl, 4-chlorophenyl-3-iodopropargyl formaldehyde, 3-bromo-2,3-diiodine-2-propenyl ethyl, 2,3,3-tri-iodoalyl alcohol, alcohol of 3-bromo-2,3-diiodine-2-propenyl, 3-iodo-2-propynyl n-butylcarbamate, 3-iodine-3-iodine-n-hexylcarbamate, 3-iodine-cyclohexyl carbamate 2-propynyl, 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-trimethyleneditiazolinone, 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, ampropylfos, anilazine asomato, aureofungin, azaconazole, azafendine, azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomil, benquinox, bentalurone, bentiavalicarb, bentiazol, benzalconium chloride, benzoxin, benzamine, benzamine , betoxazine, biloxazole, binapacril, biphenyl, bitertanol, bitionol, bixafen, blasticidin-S, boscalide, bromotalonil,

bromuconazole, bupyrimate, butiobate, butylamine calcium polysulfide, captafol, captan, carbamorph, carbendazim, carbendazim hydrochloride, carboxine, carpropamide, carvone, CGA41396, CGA41397, quinomethion, chitosan, chlorobenthemethyl, chlorobenthemethyl, chloranhydrone chlorothalonil, chlorozolinate, clozolinate, climbazol, clotrimazole, clozilacone, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, sulfate copper, copper talate, copper zinc chromate and Bordeaux mixture, cresol, cufranebe, cuprobam, cuprous oxide, cyazofamide, cyclamfuramide, cycloheximide, cyflufenamide, cymoxanil, cyprendazole, cyproconazole, ciprodinil, decozentine, dazone, dehydroacetic acid, di-2-pyridyl disulfide 1,1'-dioxide, diclofluanide, diclomezine, diclone, dichlorane, dichlorophene, diclozoline, diclobutr azole, diclocimete, dietofencarb, diphenoconazole, difenzoquate, diflumetorim, 0.0-diisopropyl-S-benzyl thiophosphate, dimefluazole, dimethaclone, dimetconazole, dimetomorph, dimethyrimol, diniconazole, diniconazole, diniconazole, dinobazone dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrithione, disulfiram, ditalymph, dithianone, dithioether, dodecyldimethyl ammonium chloride, dodemorph, dodicine, dodine,

doguadine, drazoxolone, edifenfos, enestroburine, epoxiconazole, etaconazole, etem, etaboxam, ethirimol, ethoxyquin, ethylicin, (Z) -N-benzyl-N ([methyl (methyl-thioethylideneamino-oxicarbonyl) amino] thio-alanium-thio-alanium-thio-alanium-thio-alanium-thio-alanium] thio) ethyl, etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenexamide, fenitropane, fenoxanil, fenpiclonil, fenpicoxamide, fenpropidine, fenpropimorfe, fenpimone, flaminamide, flaminamine, flaminamine flumetover, flumorfe, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flussulfamide, flutanil, flutolanil, flutriafol, fluxpyroxade, leaflet, formaldehyde, fosetil, fuberidazol, fururilur, fururalil, fururalil, fururalil gliodine, griseofulvin, guazatin, halachrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydrargafene, hydroxy-isoxazole, himexazole, imazalil, su imazalil lfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezine, iodocarb, ipconazol, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanylbutyl, isopropyl, isopropyl, isopropyl, isoprotiolane, isoprotiolan, LY248908, mancozebe, mandipropamide, manebe, mebenil, mecarbinzide, mefenoxam,

mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercury chloride, meptildinocape, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole, methanesulfocarb, metfuroxam, methyl bromide, methylamide, zinc methylamine, isothiocyanate, isothiocyanate, isothiocyanate metrafenone, metsulfovax, milnebe, moroxidine, myclobutanil, myclozoline, nabam, natamycin, neoasozine, nickel dimethyldithiocarbamate, nitrostirene, nitrotal-iso-propyl, nuarimol, octyline, offurace, organomercurine, oxoxytrin, oroxin, oroxypramine, oroxin, or oxin-copper, oxolinic acid, oxpoconazole, oxycarboxine, parinol, pefurazoate, penconazole, pencicurone, penflufen, pentachlorophenol, pentiopyrade, fenamacril, phenazine oxide, phosphiphen, phosethyl-Al, phosphoric acids, phthaoxine, pituoxide, picoxy , polyoxrim, poliram, probenazol, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proq uinazide, protiocarb, protioconazole, pidiflumetofen, piracarbolide, piraclostrobin, pyramethrostrobin, pyramoxystrobin, pyrazophos, pyribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyrimethoxy, quiroquinone, pyrochloride, quiroxin, pyrochloride, pyroquinone, pyrochloride, quiroxin , quintozene, rabenzazole,

santonine, silkxane, siltiofam, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, sultropene, tebuconazole, tebfloquine, keyboardophthalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluoride, thiadifluoride, thiadifluoride methyl, thioquinox, take, thiadinyl, thymibenconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimefone, triadimenol, triamiphos, triarimol, triazbutyl, triazoxide, tricyclazole, tridemorphine, trifloxytrazine, trifloxytrazol, trifloxytrol, trifloxytrol, trifloxytrol, trifloxytrol, trifloxytrazole valifenalate, vapam, vinclozoline, zarilamide, zineb, ziram and zoxamide.

[00150] 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 e EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO0-9522552. 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 clorsulone, and cestocides, such as praziquantel and epsiprantel.

[00151] The compounds of the invention can be used in combination with derivatives and analogs of the paraherquamide / marcfortin class of anthelmintic agents, as well as antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE- 19520936.

[00152] 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 0 382 173 and EP O 503 538.

[00153] The compounds of the invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenurone; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.

[00154] 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 there.

[00155] Other examples of such biologically active compounds with which the compounds of the invention can be used in combination include but are not restricted to the following:

[00156] Organophosphates: Aphosphate, azametiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusaphos, chlorethoxyphos, chlorpyrifos, chlorfenvinfos, chlormefos, demetone, demetona-S-methyl, demetona-s-metonone-S-metilsone-dialsone , dichlorvos, dicrotofos, dimetoato, disulfotona, etione, etetoprofos, etrinfos, famfur fenamifos, fenitrotiona, fensulfotiona, fentiona, flupirazofos, fonofos, formionea, fostiazato, heptenofos, isazofos, methazione, methoxyamide, isation, methaylation, isoxation, methaylation, isoxation, methaylation, isoxation, methoxy, parationa, mevinfos, monocrotofos, nalede, ometoate, oxidemetone-methyl, paraoxone, parationa, parationa-methyl, fentoate, fosalone, phospholane, phosfocarb, phosmetho, phosphamidone, forato, foxime, pirimifos, pirimifos-methyl, propenofos, propenofos protiofos, piraclofos, pyridapentiona,

quinalfos, sulprofos, temefos, terbufos, tebupirinfos, tetrachlorvinfos, timetona, triazofos, triclorfona, vamidotiona.

[00157] 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.

[00158] 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.

[00159] Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, fluphenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, chlorophyzine, triflazoline, triflazoline, triflazole, triflazole b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxifene, methoprene (including S-methoprene), phenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

[00160] Other antiparasitic agents: acequinocila, amitraz, AKD-1022, ANS-118, azadiractin, Bacillus turingiensis, bensultape, biphenazate, binapacryl, bromopropylate, BTG- 504, BTG-505, canfeclor, cartape, chlorobenzide, chlorobrenzide, chlorobenzylate, chlorobenzylate, chlorobenzyl , clothianidin, cyromazine, diaclodene, diafentiurone, DBI-3204, dinactin, di-hdroxymethyldihydroxypyrrolidine, dinobutone, dinocape, endosulfan, etiprol, etofenprox, phenazaquin, flumite, MTI- 800, fliroxin, flaminophen, fluoroxime , fluproxifene, halofenprox, hydramethylnone, IKI-220, canemite, NC-196, neem protector, nidinorterfuran, nitanpirame, SD-35651, WL-108477, pyridine, propargite, protrifenbute, pimetrozine, pyridine, pyridine, pyridine, pyridine, pyridine, pyrimide -195, RH-0345, RH-2485, RYI-210, S $ -1283, Ss-1833, SI-8601,

silafluofeno, silomadina, spinosade, tebufenpirade, tetradifone, tetranactin, thiaclopride, thiocyclamide, thiametoxame, tolfenpirade, triazamate, trietoxispinosine, trinactin, verbutine, vertalec, YI-5301.

[00161] Biological agents: Bacillus thuringiensis 5ssp aizawai, kurstaki, Bacillus thuringiensis endotoxin delta, baculovirus, entomopathogenic bacteria, viruses and fungi.

[00162] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[00163] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprol, cefquinome, florfenicol, buserelin, cefovecin, trefovecin, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefovinine, trefoquinone .

[00164] 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 compounds T-2.01 to T-2.35 to T-23.01 to T-23.35 shown in Tables 2 to 23 (below) or of compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below).

[00165] an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,

[00166] an acaricide selected from the group of substances consisting of 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC name / Chemical Abstracts) (1059) + TX, 2-fluoro-N-methyl-N-l1-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, amidionine (870) + TX, amidoflumete [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenic 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, butocarboxy (103) + TX, butoxycarboxy (104) + TX, butylpyridabene (alternative name) + TX, polysulfide calcium (IUPAC name) (111) + TX, canfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothione (947) + TX, CGA 50'439 (development code) (125) + TX, quinomethionate (126) + TX, chlorobenside (959) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorophenetole ( 968) + TX, chlorophensone (970) + TX, chlorfensulfide (971) + TX, chlorfenvinfos (131) + TX, chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiurone (978) + TX, chloropropylate (983 ) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, cine rina I (696) + TX, cinerina II (696) + TX, cinerines (696) + TX, clofentezina (158) + TX, closantel (alternative name) [CCN] + TX, coumafos (174) + TX, crotamitone ( alternative name) [CCN] + TX, crotoxifos (1010) + TX, cufranebe (1013) + TX, cyantoate (1020) + TX, kyflumetophen (No.

Reg.

CAS: 400882-07-7) + TX, cyhalothrin (196) + TX, cyiexatin (199) + TX, cypermethrin (201) + TX, DCPM (1032) + TX, DDT (219) + TX, demefiona (1037) + TX, deflate-O (1037) + TX, deflate-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O- methyl (224) + TX, demetone-S (1038) + TX, demetone-S-methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diaphentiurone (226) + TX, dialects (1042) + TX, diazinona

(227) + TX, diclofluanide (230) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicofol (242) + TX, dicrotofos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinobutone (269) + TX, dinocape (270 ) + TX, dinocape-4 [CCN] + TX, dinocape-6 [CCN] + TX, dinoctone (1090) + TX, dinopentone (1092) + TX, dinosulfone (1097) + TX, dinoterbone (1098) + TX, dioxationa (1102) + TX, diphenylsulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfotone (278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothionin (1121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethione (309) + TX, methyl ethoate (1134) + TX, ethoxazole (320) + TX, etrinfos (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, fensona (1157) + TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX , fluacripyrim (360) + TX, fluazurone (1166) + TX, flubenzimine (1167) + TX, flucicloxurone (366) + TX, flucitrinate (367) + TX, fluenethyl (1169) + TX, flufenoxurone (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formothione (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, isocarbophos (alternative name) (473) + TX, O- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name ) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmine I ( 696) + TX, jasmine II (696) + TX, jodfenfos (1248) + TX, lindane (430) + TX, lufenurone (490) + TX, malationa (492) + TX, malonobene (1254) + TX, mecarbam ( 502) + TX, mephospholane (1261) + TX, messulfene (alternative name) [CCN] + TX, metacryphs (1266) + TX, metamidophos (527) + TX, methidathione (529) + TX, metiocarb (530) + TX , methomyl (531) + TX methyl bromide (537) + TX, metolcarb (550) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin — approx (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, nitrilacarb complex 1: 1 chloride Zinc (1313) + TX, NNI-0101

(compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxideprofos (1324) + TX, oxisulfotone (1325) + TX, pp'- DDT (219) + TX, parathione (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, fencaptona (1330) + TX, fentoate (631) + TX, forato ( 636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosphamidone (639) + TX, foxim (642) + TX, pyrimiphos-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, propetanfos (673) + TX, propoxur (678) + TX, protidationa (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridafentiona (701) + TX, pyrimidifene (706) + TX, pyrimitate (1370) + TX, 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-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpirade (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinfos (777) + TX, tetradifone (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, tiafenox (alternative name) + TX, thiocarbox (1431) + TX, tiofanox (800) + TX, thiometone (801) + TX, thioquinox (1436) + TX, thuringian (alternative name) [CCN] + TX, triamiphos (1441) + TX, triaratene (1443) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, trichlorphone (824) + TX, triphenophones (1455) + TX, trinactin (alternative name) (653) + TX, vamidothione (847) + TX, vaniliprol [CCN] and YI-5302 (composite code) + TX,

[00167] 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,

[00168] 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,

[00169] an avicide selected from the group of substances consisting of chloralose (127) + TX, endrine (1122) + TX, fentiona (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX,

[00170] a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN ] + TX, dichlorophene (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafene (alternative name) [CCN] + TX, casugamycin (483) + TX, hydrated casugamycin hydrochloride (483) + TX, nickel bis (dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapirin (580) + TX, octilinone (590) + TX, oxolinic acid ( 606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, sesquisulfate - streptomycin (744) + TX, keyboard software (766) ) + TX, and thiomersal (alternative name) [CCN] + TX,

[00171] 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 Ssubesp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis Ssubesp. 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 qglaseri (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 FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA and known under the registered name Taegroº) + TX,

[00172] a soil sterilizer selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,

[00173] a chemosterilizer selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzurone (250) + TX, dimatife ( alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl afolate [CCN] + TX, slurry [CCN] + TX, penflurone (alternative name) [CCN] + TX, tepa [CCN] + TX, thioempa (alternative name) [CCN] + TX, tiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN ] and uredepa (alternative name) [CCN] + TX,

[00174] an insect pheromone selected from the group of substances consisting of (E) -dec-5-en-l1-yl acetate with

(E) -dec-5-en-1-0l (IUPAC name) (222) + TX, (E) acetate - tridec-4-en-l1-yl (IUPAC name) (829) + TX, (E ) -6-methyl-hept- 2-en-4-0l (IUPAC name) (541) + TX, (E, Z) acetate - tetradeca-4,10-dien-l1-yl (IUPAC name) (779 ) + TX, (Z) -dodec-7-en-l-yl acetate (IUPAC name) (285) + TX, (Z) - hexadec-11-enal (IUPAC name) (436) + TX, acetate (Z) - hexadec-11-en-1-yl (IUPAC name) (437) + TX, (Z) acetate - hexadec-13-en-l11-in-1-yl (IUPAC name) (438) + TX, (Z) -icos- 13-en-10-0na (IUPAC name) (448) + TX, (Z) -tetradec-7-en-l- al (IUPAC name) (782) + TX, (Z ) -tetradec-9-en-l-ol (IUPAC name) (783) + TX, (Z) acetate -tetradec-9-en-l1-yl (IUPAC name) (784) + TX, (7E acetate) , 9Z) -dodeca-7,9-dien-l-yl (IUPAC name) (283) + TX, (972,11E) -tetradeca-9,11- dien-1-yl acetate (IUPAC name) (780 ) + TX, (9Z, 12E) acetate - tetradeca-9,12-dien-l1-yl (IUPAC name) (781) + TX, 14-methyloctadec-l-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-mu ltistriatina (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-l1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-l-yl acetate (IUPAC name) (287 ) + TX, dodeca-8 + TX, 1l0-dien-l-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) ( 317) + TX, eugenol (alternative name) [CCN] + TX, frontal (alternative name) [CCN] + TX, gossiplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name ) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca acetate-2,13-dien-l1-ila (IUPAC name) (588) + TX, octadeca acetate-3,13-dien-l1-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-l11-en-1-ila acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B> (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call ( alternative name) [CCN] + TX,

[00175] 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 (TUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, phthalate dimethyl [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] + picaridin [CCN] + TX ,

[00176] an insecticide selected from the group of substances consisting of l1-dichloro-l-nitroethane (IUPAC / Chemical Abstracts name) (1058) + TX, 1,1-dichloro-2,2-bis (4-ethylphenyl) ethane ( IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (IUPAC name / Chemical Abstracts) (916) + TX, 2,2,2-trichloro-1- (3,4-dichlorophenyl) ethyl acetate (IUPAC name) (1451) + TX, phosphate 2,2-dichlorovinyl-2-ethylsulfinylethylmethyl (IUPAC name) (1066) + TX, 2- (1,3-dithiolan-2-yl) phenyl (IUPAC / Chemical Abstracts name) (1109) + TX, thiocyanate dimethylcarbamate 2- (2-butoxyethoxy) ethyl (IUPAC / Chemical Abstracts name) (935) + TX, 2- (4,5-dimethyl-1,3-dioxolan-2- methylcarbamate)

il) phenyl (IUPAC / Chemical Abstracts name) (1084) + TX, 2- (4-chloro-3,5-xylyloxy) ethanol (IUPAC name) (986) + TX, 2-chlorovinyladiethyl phosphate (IUPAC name) ( 984) + TX, 2-imidazolidone (IUPAC name) (1225) + TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 2-methyl (prop-2-inyl) aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-l-ene (IUPAC name) (917) + TX, 3- dimethylcarbamate methyl-1-phenylpyrazol-5-yl (IUPAC name) (1283) + TX, 4-methyl (prop-2-inyl) amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, dimethylcarbamate 5,5-dimethyl-3-oxocyclohex-l1-enyl (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamipride (4) + TX, acetione (alternative name ) [CCN] + TX, acetoprol [CCN] + TX, acrinatrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, aldrin (864) + TX, alethrin (17) + TX, alosamidine (name alternative) [CCN] + TX, alixicarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidithione (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasin (877) + TX, atidathione (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX,

azadiractin (alternative name) (41) + TX, azametiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, nitrogen (889) + TX, Bacillus thuringiensis delta endotoxins (name alternative) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC / Chemical Abstracts name) (892) + TX, bartrine [CCN] + TX, Bayer 22/1900 (code (development)) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultape (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioalethrin (78) + TX, S-cyclopentenyl isomer of bioalethrin (alternative name) (79) + TX, bioethanometrine [CCN] + TX, biopermetrin (908) + TX, bioresmethrin (80) + TX, bis (2-chloroethyl) ether (IUPAC name) (909) + TX, bistriflurone (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bronfenvinfos (914) + TX, bromocyclene (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, 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,

canfeclor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC / Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name ) (946) + TX, carbophenothione (947) + TX, carbosulfan (119) + TX, cartape (123) + TX, cartape hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, clorbicicleno ( 960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlorodimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorofenapyr (130) + TX, chlorofenvinfos (131) + TX, chlorfluazurone (132) + TX, chlorephes (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorfoxin (989) + TX, chlorprazophos (990) + TX, chlorpyrifos ( 145) + TX, chlorpyrifos-methyl (146) + TX, chlortiofos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerines (696) + TX , cis-resmethrin (alternative name) + TX, cyismetrin (80) + TX, clocitrine (alternative name) + TX, cloetocarb (9 99) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumafos (174) + TX, coumitoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxifos (1010) + TX, crufomato (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanophenphos (1019) + TX, cyanophos (184) + TX, cyantoate

(1020) + TX, cyclethrin [CCN] + TX, cycloprotrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine ( 209) + TX, cytoate (alternative name) [CCN] + TX, d- limonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomete (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demefiona (1037) + TX, demefa-O (1037) + TX, demefiona-S (1037) + TX, demetone (1038) + TX, demetone-methyl (224) + TX, demetone-O (1038) + TX, demetone-O-methyl (224) + TX, demetone-S (1038) + TX, demetone-S -methyl (224) + TX, demetone-S-methylsulfone (1039) + TX, diafentiurone (226) + TX, dialiphos (1042) + TX, diamidafos (1044) + TX, diazinone (227) + TX, dicapton (1050) ) + TX, diclofentiona (1051) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicresil (alternative name) [CCN] + TX, dicrotofos (243) + TX, dicyclanil (244) + TX , dieldrin (1070) + TX, phosphat that of diethyl-5-methylpyrazol-3-yl (IUPAC name) (1076) + TX, diflubenzurone (250) + TX, dilor (alternative name) [CCN] + TX, dimeflutrin [CCN] + TX, dimefox (1081) + TX, dimethane (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimethylane (1086) + TX, dinax (1089) + TX, dinex-diclexin (1089 ) + TX, dinoprope (1093) + TX, dinosam (1094) + TX, dinosebe (1095) + TX, dinotefuran (271) + TX, diophenolane (1099) + TX,

dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxationa (1102) + TX, disulfotone (278) + TX, dichrophos (1108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endothionin (1121) + TX, endrine (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epophenonane (1124) + TX, eprinomectin (alternative name) [CCN] + TX, sphenvalerate (302) + TX, etafos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethione (309) + TX, etiprol (310) + TX, etoate-methyl (1134) + TX, etoprofos (312) + TX, ethyl format (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, dibromide ethylene (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrymphs (1142) + TX, EXD (1143) + TX, fa nfur (323) + TX, fenamiphos (326) + TX, fenazaflor (1147) + TX, fenencaflor (1148) + TX, fenetacarb (1149) + TX, fenflutrina (1150) + TX, fenitrothione (335) + TX, fenobucarb (336) + TX, phenoxacrim (1153) + TX, phenoxycarb (340) + TX, phenpiritrin (1155) + TX, fenpropatrin (342) + TX, fenpirade (alternative name) + TX, fensulfothione (1158) + TX, fention (346) + TX, fentiona-ethyl [CCN] + TX, fenvalerate (349) + TX, Tfipronil (354) + TX, flonicamide (358) + TX,

flubendiamide (No.

Reg.

CAS .: 272451-65-7) + TX, flucofurone (1168) + TX, flucicloxuron (366) + TX, flucitrinate (367) + TX, TfTluenethyl (1169) + TX, flufenerin [CCN] + TX, flufenoxurone (370 ) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, Tphonophos (1191) + TX, formethanate (405) + TX, formethanate hydrochloride (405) + TX, formothionate (1192) + TX, formparanate (1193) + TX, phosmethylane (1194) + TX, phospirate (1195) + TX, fostiazate (408) + TX, fostietan (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, hexaflumurone (439) + TX, HHDN (864) + TX, hydramethylnone (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hiquincarb (1223) + TX, imidacloprid (458) + TX, imiprotrine (460) + TX, indoxacarb (465) + TX, iodomethane (IUPAC name) (542) + TX, IPSP (1229) + TX, isazophos ( 1231) + TX, isobenzane (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrine (1235) + TX, isophenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX , 0- (methoxyminothiophosphoryl) isopropyl salicylate (IUPAC name) (473) + TX, isoprothiolane (474) +

TX, isothioate (1244) + TX, isoxathion (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, kelevane (1249) + TX, quinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lympho (1251) + TX, lufenurone (490) + TX, litidationa (1253) + TX, m-cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malationa (492) + TX, malonobene ( 1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarphone (1258) + TX, menazone (1260) + TX, mephospholane (1261) + TX, mercury chloride (513) + TX, mesulfenphos ( 1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, metacryphs (1266) + TX, metamidophos (527) + TX, methanesulfonyl fluoride (IUPAC / Chemical Abstracts name) (1268) + TX, methidathione (529) + TX, metiocarb (530) + TX, metocrotophos (1273) + TX, methomyl (531) + TX methoprene (532) + TX, methoxy-butyl (1276) + TX, methotrine (alternative name) (533) + TX, methoxychloride (534) + TX, methoxyphenido (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metoflutrin [CCN] + TX, metolcarb (550) + TX, methoxyzone (1288) + TX, mevinfos (556) + TX, mexacarbato (1290) + TX, milbemectin (557) + TX, milbemycin — approximate (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294 ) + TX, monocrotofos (561) + TX, morphotion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naphthalophos (alternative name) [CCN] + TX, nalede (567) + TX, naphthalene (name IUPAC / Chemical Abstracts) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (code compound) + 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, novalurone ( 585) + TX, noviflumurone (586) + TX, OOO-5-dichloro-4-iodophenyl-O-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, 0.0-diethyl-O-4-methyl phosphorothioate -2-0x0-2H-chromen-7-yl (IUPAC name) (1074) + TX, 0.0-diethyl-0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, 0.0,0 'dithiopyrophosphate, 0'-tetrapropyl (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, ometoate (594) + TX, oxamyl (602) + TX, oxometomethyl-methyl (609) + TX, oxideprofos (1324) + TX, oxisulfotone (1325) + TX,

Pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathione (615) + TX, parathione-methyl (616) + TX, penflurone (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX , fencaptona (1330) + TX, phenothrin (630) + TX, phentoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phospholane (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidone (639) + TX, phosphine (IUPAC name) (640) + TX, foxim (642) + TX, foxim-methyl (1340) + TX, pyrimetafos (1344) + TX, pyrimicarb ( 651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, pralethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alt name alternative) [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, propetanfos (673) + TX, propoxur (678) + TX, protidationa (1360) + TX, protiofos (686) + TX, protoate (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, pyridabene (699) + TX, pyridalil (700) + TX, pyridafentiona (701) + TX, pyrimidiphene (706) + TX , pyrimitate (1370) + TX, pyriproxyphene (708) + TX, quássia (alternative name) [CCN] + TX, quinalfos (711) + TX, quinalfos-methyl (1376) + TX, quinothione (1380) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (code development) (723) + TX, RU 25475 (development code) (1386) + TX, ryan (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725 ) + TX, escradano (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-000O9 (compound code) + TX, SI-0205 (compound code) + TX, SI-O404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (design code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC / Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX , sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sofamide (1402) + TX, spinosad (737) + TX, spiromesifene (739) + TX, spirotetramate (CCN) + TX, sulcofurone (746) +

TX, sulcofurone-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, tebufenpirade (763) + TX, tebupirinfos (764) + TX, teflubenzurone ( 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, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, ticrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiophanox (800) + TX, thiometone (801) + TX, thionazine (1434) + TX, tiossultape (803) + TX, thiosultape-sodium (803) + TX, thuringensin (alternative name) [CCN] + TX, tolfenpi rade (809) + TX, tralometrine (812) + TX, transflutrin (813) + TX, transpermetrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazurone (alternative name) + TX, trichlorphone (824) + TX, trichlormethophos-3 (alternative name) [CCN] + TX, trichloronate (1452) + TX, triphenophos (1455) + TX, triflumurone (835) + TX, trimetacarb ( 840) + TX, triprene (1459) + TX, vamidothole (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, cyantraniliprol [736994-63-19 + TX , chlorantraniliprol [500008-45-7] + TX, cyienopyraphene [560121-52-0] + TX, cyflumetophen [400882-07-7] + TX, pyrifluquinazone [337458-27-2] + TX, espinetoram [187166-40 - 1 + 187166-15-0] + TX, spirotetramate [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprol [704886-18-0] + TX, meperflutrin [915288-13 -0] + TX, tetramethylflutrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/092115) + TX,

[00177] a molluscicide selected from the group of substances consisting of bis (tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloetocarb (999) + TX , copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, metiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamina (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, oxide tributyltin (913) + TX, triphenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprol [394730- 71 -31] + TX,

[00178] a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane "(IUPAC / Chemical Abstracts name) (1045) + TX, 1,2- dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 1,1- 3,4-dichlorotetrahydrothiophene dioxide (IUPAC / Chemical Abstracts name) (1065) + TX, 3- (4-chlorophenyl) -5-methylrodanine (IUPAC name) (980) + TX, 5-methyl-6- acid thioxo-1,3,5-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, chloropicrina (141) + TX, chlorpyrif os (145) + TX, cloetocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomete (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, diclofentiona (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, fensulfothione (1158) + TX, phostiazate (408) + TX, Tfostietano (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ivermectin (alternative name ) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphone (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam sodium (519 ) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, composition of Myrothecium verrucaria ( alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidone (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, tiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazurone (alternative name) + TX , xylenols [CCN] + TX, YI-5302 (compound code) and zeatin

(alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,

[00179] a nitrification inhibitor selected from the group of substances consisting of potassium ethyl xanthate [CCN] and nitrapirin (580) + TX,

[00180] 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 ,

[00181] a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4- (quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX , alpha-hydrochlorine [CCN] + TX, aluminum phosphide (640) + TX, antu (880) + TX, arsenious oxide (882) + TX, barium carbonate (891) + TX, bistiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorofacinone (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, range-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, phosphide d and magnesium (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, fosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinurone (1371) + TX, esciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX , sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX,

[00182] 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-hexyl cycle -hex-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,

[00183] an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinone (227) + TX, dicyclopentadiene

(chemical name) (1069) + TX, guazatin (422) + TX, guazatin acetates (422) + TX, metiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, draw ( 804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

[00184] a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,

[00185] a wound protector selected from the group of substances consisting of mercuric oxide (512) + TX, octylinone (590) and thiophanate-methyl (802) + TX,

[00186] and biologically active compounds selected from the group consisting of ametoctradine [865318-97-4] + TX, amisulfon [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzovindiflupir [1072957-71 -1] + TX, bitertanol [70585- 36-3] + TX, bixafen [581809-46-3] + TX, bromuconazole [116255-48-2] + TX, coumoxystrobin [850881-70-8] + TX, cyproconazole [94361-06-5] + TX, diphenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [238410-11-2] + TX, epoxiconazole [106325-08- 0] + TX, fenbuconazole [114369-43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, 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, mandestrobin [173662-97- 0] (can be prepared according to the procedures described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0 ] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30- 4] + TX, penflufen [494793-67-8] + TX, penconazole [66246- 88-6] + TX, protioconazole [ 178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [112281-77-3] + TX, triadimefone [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, carbendazin [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, clozolinate [84332-86-5] + TX, diclozoline [24201-58-9 ] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, 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 fProc.

BCPC, Congr.

Int., 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, entered [9006- 42-2] + TX, propineb [ 12071-83-9] + TX, remove [137-26-8] + TX, zineb [12122-67-7] + TX, remove [137-30-4] + TX, captafol [2425-06-1] + TX, captano [133-06-2] + TX, diclofluanide

[1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folet [133-07-3] + TX, tolylfluanide [731-27-1] + TX, Bordeaux mixture [8011-63 -0] + TX, copper hydroxide [20427-59-2] + TX, copper oxychloride [1332-40-7] + TX, copper sulfate [7758-98-7] + TX, copper oxide [1317 -39-1] + TX, maneuver [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocape [131-72-6] + TX, nitrotal-isopropyl [10552-74 -6] + TX, buildings [17109-49-8] + TX, iprobenphs [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, bentiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, quinomethionate [2439-01-2] + TX, 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, diclocimete [139920-32-4] + TX , diclomezine [62865-36-5] + TX, dichlorane [99-30-9] + TX, dietofencarb [87130-20-9] + TX, dimetomorph [110488-70-5] + TX, SYP-LI90 (Flumorfe) [211867-47-9] + TX, dithianone [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, fluopicolid [239110-15-7] + TX , flusulfamide [106917-52-6] + TX, fenexamide [126833-17-8] +

TX, fosetil-aluminum [39148-24-8] + TX, himexazole [10004-44-1] + TX, Iprovalicarb [140923-17-7] + TX, IKF-916 (Cyzofamide) [120116-88-3] + TX, casugamycin [6980-18-3] + TX, metasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencicurone [66063-05-6] + TX, phthalide [27355 -22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [11113-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazide [189278-12-4] + TX, pidiflumetofen [1228284-64-7] + TX, pyramethostrobin [915410-70-7] + TX, pyrokylone [57369-32-1] + TX, pyrophenone [688046- 61-9] + TX, pyribencarb [799247-52-2] + TX, pyrisoxazole [847749-37-5] + TX, quinoxifene [124495- 18-7] + TX, quintozene [82-68-8] + TX , sulfur [7704-34-9] + TX, Timorex Gold! "(plant extract containing tea tree oil from the Stockton Group) + TX, tebufloquine [376645- 78-2] + TX, thiadinyl [223580-51- 6] + TX, triazoxide [72459- 58-6] + TX, tolprocarb [911499-62-2] + TX, triclopyricarb [902760-40-1] + TX , tricyclazole [41814-78-2] + TX, triforin [26644-46-2] + TX, validamycin [37248-47-8] + TX, valiphenalate [283159-90-0] + TX, zoxamide (RH7281) [ 156052- 68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, fenamacrila + TX, silkxane [874967-67- 6] + TX, <trinexapac-ethyl [95266-40-3] + TX, (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methane-naphthalen-5-

il) 3-difluoromethyl-1-methyl-1H-pyrazol-4- acid amide

carboxylic acid (disclosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3 ', 4', 5'-trifluoro-biphenyl-2-yl) disclosed in WO 2006/087343) + TX, [(35, 4R, 4aR, 65.6aS, 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, 11Hnafto [2,1-b] pyran [3,4-e] pyran-4-yl] methyl-cyclopropanecarboxylate [915972-17-7] + TX and 1,3,5-trimethyl- N- (2-methyl-1-oxopropyl) -N- [ 3- (2-methylpropyl) -4- [2,2,2-trifluoro-1-methoxy-1- (trifluoromethyl) ethyl] phenyl] -1H-pyrazol-4-carboxamide [926914-55-8] + TX,

[00187] 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-4-1yl) -1-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX , 3- (3,4-dichloro-1,2-thiazol-5-ylmethoxy) -1l 1,1-dioxide, 2-benzothiazole (can be prepared according to procedures described in WO 2007/129454) + TX, 2- [2 - [(2,5-dimethylphenoxy) methyl] phenyl] -2-methoxy-N-methyl-acetanide + 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, oxatiapiprolina + TX [1003318- 67-9], N- [6 - [[[(1-methylthetrazol-5-yl) -phenyl-methylene] lamino] oxymethyl] -2-pyridyl] tert-butyl carbamate + TX, N- [2- ( 3,4- difluorophenyl) phenyl] -3- (trifluoromethyl) pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3- (difluoromethyl) -1-methyl-N- [(3R) -1,1,3-trimethylindan-4-yl] pyrazole-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-1-yl) propan-2-ol + TX, (2RS) -2- [4- (4- chlorophenoxy) -a, a, a-trifluoro-o-tolyl] -3-methyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol + TX, 2- (difluoromethyl) -N - [(3R) -3-ethyl-1,1-dimethyl-indan-4-ill] lpiridine-3-carboxamide + TX, 2- (difluoromethyl) -N- [3-ethyl-1,1-dimethyl -indan-4-yl] pyridine-3-carboxamide + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N-ethyl-N-methyl-formamidine + TX, N' - [4- (4,5-dichlorothiazol-2-yl) oxy-2,5-dimethyl-phenyl] - N-ethyl-N-methyl-formamidine (can be prepared according to the procedures described in WO 2007/031513) + TX, [2- [3- [2- [1- [2- [3,5-bis (difluoromethyl) pyrazol-1-yl] acetyl] -4-piperidyl] thiazol-4-yl] -4,5- methanesulfonate dihydroisoxazol-5-yl] -3-chloro-phenyl] (can be prepared according to the procedures described in WO 2012/025557) + TX, N- [6 - [[(Z) - [(1-methyltetrazole -5-yl) - phenyl-methylene] amino] oxymethyl] -2-pyridyl] but-3-inyl carbamate (can be prepared according to the procedures described in WO 2010/000841) + TX, 2 - [[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -4H-1,2,4-triazol-3-thione (can be prepared from according to the procedures described in WO 2010/146031) + TX, N - [[5- [4- (2,4-dimethylphenyl) triazol-2-yl] -2-methyl-phenyl] methyl] methyl carbamate + TX , 3-chloro-6-methyl-5-phenyl-4- (2,4,6-trifluorophenyl) pyridazine (can be prepared according to the procedures described in WO 2005/121104) + TX, 2- [2-

chloro-4- (4-chlorophenoxy) phenyl] -1- (1,2,4-triazol-1-yl) propan-2-0l (can be prepared according to the procedures described in WO 2013/024082) + TX , 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4- (2,6- difluorophenyl) -6-methyl-5-phenyl-pyridazine-3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774) + TX, (R) -3- (difluoromethyl) -1-methyl-N - [1,1,3-trimethylindan-4-yl] pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2011/162397) + TX, 3- (difluoromethyl) -N- (7-fluoro -1,1,3-trimethyl-indan-4-yl) -1l-methyl-pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1- [2- [ [1- (4-chlorophenyl) pyrazol-3-yl] oxymethyl] -3-methyl-phenyl] - 4-methyl-tetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072) + TX, l1-methyl-4- [3-methyl-2 - [[2-methyl- 4- (3,4,5-trimethylpyrazole-1-

il) phenoxy] methyl] phenyl] tetrazol-5-one (can be prepared according to the procedures described in WO 2014/051165) + TX, (Z, 2E) -5- [1- (4-chlorophenyl) pyrazole- (4-Phenoxyphenyl) methyl (4-phenoxyphenyl) oxy-2-methoxy-imino-N, 3-dimethyl-pent-3-enamide + TX, 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 the procedures described in WO 2010/130767) + TX, 3- (difluoromethyl) -N - [(R) -2,3-dihydro- 1,1,3-trimethyl-1H-inden-4-1yl] -1-methylpyrazole- 4-carboxamide [1352994-67-2] + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) -N- ethyl-N-methyl-formamidine + TX, N' - [4- (4 , 5-dichloro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX, N '- (2,5-dimethyl-4-phenoxy-phenyl) - N-ethyl-N-methyl-formamidine + TX, N '- [4- (4,5-dichloro-thiazol-2-yloxy) -2,5-dimethyl-phenyl] -N-ethyl-N-methyl-formamidine + TX, De L o DA ro à N o

[00188] (fenpicoxamide [517875-34-2]) + TX (as described in WO 2003/035617), 2- (difluoromethyl) -N- (1,1,3-trimethylindan-4-yl) pyridine-3- carboxamide + TX, 2- (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-ill] lpyridine-3-carboxamide + TX and 2- (difluoromethyl) -N - [(3R) -

1,1-dimethyl-3-propyl-indan-4-yl) pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and / or WO 2016/139189.

[00189] References in parentheses before the active ingredients, eg [3878-19-1] refer to the Chemical Abstracts Registration number. The mixing partners described above are known. Where the active ingredients are included in the “The Pesticide Manual" [The Pesticide Manual - The World Compendium; Thirteenth Edition; Editor: CDS Tomlin; The British Crop Protection Council] are described there under the entry number given between curly brackets previously for the particular compound; for example, the compound "abamectin" is described under the entry number (1). Where "[CCN]" is previously added to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names" , which is accessible via the internet [A. Wood; Compendium of Pesticide Common Names, Trademark O 1995-2004]; for example, the compound “acetoprol” is described under the Internet address http: // www. alanwood.net/pesticides/acetoprole.html.

[00190] Most of the active ingredients described above are referred to earlier 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 this case, the IUPAC name, the IUPAC / Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” are used or, if none is used of these designations nor a “common name”, an “alternative name” is used. "At the. CAS Reg. ”Means the Chemical Abstracts Registration Number.

[00191] The active ingredient mixture of the compounds of formula (1) selected from a compound selected from compounds T-2.01 to T-2.35 to T-23.01 to T-23.35 shown in Tables 2 to 23 (below) or compounds A .1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below), preferably in a mixing ratio of 100: 1 to 1: 6000, especially from 50: 1 to 1:50, more especially in a ratio of 20: 1 to 1:20, even more especially from 10: 1 to 1:10, especially 5: 1 and 1: 5, with a special preference being given to a ratio of 2: 1 to 1: 2, and a ratio of 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.

[00192] The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to pests or their environment, with the exception of a method for treating the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

[00193] Mixtures comprising a compound selected from compounds T-2.01 to T-2.35 to T-23.01 to T-23.35 shown in Tables 2 to 23 (below) or compounds A.l1 to A.60 described in Table A ( below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below) and one or more active ingredients as described above can be applied, for example, in a unique “ready-mix” form, in a combined spray mixture made up of separate formulations of the components of unique active ingredients, such as a “tank mix”, and in a combined use of the unique active ingredients when applied in a sequential manner, ie, one after the other with a relatively short period, such as a few hours or days. The order of application of a compound selected from compounds T-2.01 to T-2.35 to T-23.01 to T-23.35 shown in Tables 2 to 23

(below) or compounds A.1 to A.60 described in Table A (below), compounds B.1 to B.30 described in Table B (below) and compounds C.1 to C.8 described in Table C (below), and the active ingredient (s) as described above, is not essential to the operation of the present invention.

[00194] 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 tackifiers, fertilizers or other active ingredients to achieve specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[00195] 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 (TI) for the preparation of these compositions are also a subject of the invention.

[00196] Another aspect of the invention relates to the use of a compound of Formula (TI) or an individual compound "preferred as defined here, 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 (I) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as described above, to control or prevent infestation from plants, eg, useful plants such as crop plants, their propagating material, eg, seeds, collected cultures, eg, collected food crops, or non-living materials by insects or microorganisms, preferably fungal organisms.

[00197] An additional aspect of the invention relates to a method of controlling or preventing an infestation of plants, eg, useful plants such as crop plants, their propagating material, eg, seeds, collected crops, eg, food cultures collected, or from non-living materials by insects or phytopathogenic microorganisms or that cause deterioration or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of Formula (1) 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.

[00198] Means of controlling or preventing means reducing infestation by phytopathogenic microorganisms or that cause deterioration that is potentially harmful to man, especially fungal organisms, to such an extent that an improvement is demonstrated.

[00199] A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, Or insects that comprises the application of a compound of Formula (1), or an agrochemical composition that contains at least one of those 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 through 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, e.g. , in granular form (application to the soil). In irrigated rice crops, such granules can be applied to the irrigated rice field. The compounds of Formula (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.

[00200] A formulation, e.g., a composition containing the compound of Formula (I) and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of Formula (1), 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.

[00201] Advantageous application rates are normally 5ga2kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, more preferably from 20 g to 600 g a.i./ha. When used as a seed drenching agent, convenient dosages are 10 mg to 1 g of active substance per kg of seeds.

[00202] When the combinations of the present invention are used to treat seeds, rates of 0.001 to 50 g of a compound of Formula (1) per kg of seed, preferably from 0.01 to 10 g per kg of seed, are generally sufficient .

[00203] Suitably, a composition comprising a compound of Formula (I) according to the present invention is applied preventively, meaning before disease development, or curatively, meaning after disease development.

[00204] 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 concentrate suitable for 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 seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a suspension for capsules (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.

[00205] Such compositions can be produced in a conventional manner, eg by mixing the active ingredients with appropriate formulation aggregates (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, antifreeze, adhesives, thickeners and compounds that provide adjuvant effects). Likewise, conventional slow-release formulations can be employed where long-term efficacy is desired. In particular, Formulations to be applied to spray forms, such as water-dispersible concentrates (eg, EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvant effects, eg, the condensation product of formaldehyde with naphthalene sulfonate, an alkylarylsulfonate, a lignin sulfonate, a fatty alkyl sulfate, and an ethoxylated alkylphenol and an ethoxylated alkylphenol ethoxylated fatty alcohol.

[00206] A seed coating formulation is applied in a manner known per se to the seeds employing the combination of the invention and a formulation diluent for adequate seed coverage, e.g., as an aqueous suspension or in a dry powder form with good adherence to seeds. Such seed cover formulations are known in the art. Seed cover formulations can contain the single active ingredients or the combination of active ingredients in an encapsulated form, eg as slow release capsules or microcapsules.

[00207] In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% of agriculturally acceptable surfactant and 10 to 99.99% of inert and solid or liquid formulation adjuvant (s) , the active agent consisting of at least the compound of Formula (TI) 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 for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight, of active agent. While commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

[00208] While it is preferable to formulate commercial products as concentrates, the end user will normally use diluted formulations.

[00209] Table 1 (below) discloses 35 combinations (compounds 1.01 to 1.35) of the substituents R1, R2, R3, R4, Rº and Rº according to compounds as defined for Formula (T). Formula (T) corresponds to formula (1) as defined for the present invention.

RR nº F F | ZE Z «is RR R mn

[00210] Each of Tables 2 to 23 (following Table 1) makes available 35 additional individual compounds of formula (T) in which Z is as specifically defined in Tables 2 to 23 (Formulas T-2 to T-23 ), which refer to Table 1 where R !, R2, R3, R4, R & and R6 are specifically defined. Table 1: Rº R2? R3 Rº Rô no.

Rº R2 R3 Rº R5 no.

Compound Rº R2? R3 Rº R no.

[00211] Table 2: This table discloses compounds T-2.01 to T-2.35 of the formula (T-2), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1.

FNA RNA 1 | Dr? “Nd ON R N F YA | o N RÉ RR RR (T-2)

[00212] Table 3: This table discloses compounds T-3.01 to T-3.35 of the formula (T-3), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1.

He RNA F e. | Dr == N N E So Rº RR RR (T-3)

[00213] Table 4: This table discloses compounds T-4.01 to T-4.35 of the formula (T-4), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1. Ro NO F Rº / D + 1 OH; 3C: - is 6 RR R (T-4)

[00214] Table 5: This table discloses compounds T-5.01 to T-5.35 of the formula (T-5), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1. H3C CH; n.eN o

A º - O kN R N F NR ADL OA: s N F

NO nº 5 '6 HC R R 2 3 R (T-5)

[00215] Table 6: This table discloses compounds T-6.01 to T-6.35 of the formula (T-6), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1.

N == Rº NO F

ON RAD OA S F AT THE

RR 6 He R R 2 3 R (T-6)

[00216] Table 7: This table discloses compounds T-7.01 to T-7.35 of the formula (T-7), which are a compound of the formula (1) in which R !, Rº, R3, Rº, Rº and R6 have the specific meanings given in Table 1. =. and RNA F x Rº | Dr s N E

AT THE

R 5 '6 RR 2 nsº R (T-7)

[00217] Table 8: This table discloses compounds T-8.01 to T-8.35 of the formula (T-8), which are a compound of the formula (1) in which R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1.

F F Ro NO F F.% n | Er s N FE

NO Rº 5 6 RR 2 H3º R (T-8)

[00218] Table 9: This table discloses compounds T-9.01 to T-9.35 of the formula (T-9), which are a compound of the formula

(1) where R !, Rº, R3, R4, Rº and R6 have the specific meanings given in Table 1.

CC o RN F = R | Dr Ss N nº Ê Pr KR 6 n and R RR? (T-9)

[00219] Table 10: This table discloses the compounds T-

10.01 to T-10.35 of the formula (T-10), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1. n and RNA F 3 R | Dr +: 7

N> A RR 5 6

RR He KR (T-10)

[00220] Table 11: This table discloses the compounds T-

11.01 to T-11.35 of the formula (T-11), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1.

RNA F À | Dr DOS N r - Rº H3; C 57 6 COR RR (T-11)

[00221] Table 12: This table discloses the compounds T-

12.01 to T-12.35 of the formula (T-12), which are a compound of the formula (1) in which R !, Rº? º, R3, R4, R & and R6 have the specific meanings given in Table 1. Hz3C.

ms P RNA F

ATA

N RR RR RR (T-12)

[00222] Table 13: This table discloses the compounds T-

13.01 to T-13.35 of the formula (T-13), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1.

RNA F N, i

R He RR RR (T-13)

[00223] Table 14: This table discloses the compounds T-

14.01 to T-14.35 of the formula (T-14), which are a compound of the formula (1) in which R !, R2, R3, R4, Ró and R6 have the specific meanings given in Table 1.

Fa RN F N: s

R HE R RR RR (T-14)

[00224] Table 15: This table discloses the compounds T-

15.01 to T-15.35 of the formula (T-15), which are a compound of the formula (1) in which R !, R2, R3, R4, Ró and R6 have the specific meanings given in Table 1.

meo PR IS N:

R He R R RR (T-15)

[00225] Table 16: This table discloses the compounds T-

16.01 to T-16.35 of the formula (T-16), which are a compound of the formula (1) in which R !, R2, R3, R4, Ró and R6 have the specific meanings given in Table 1.

A A NE NO:

R He R RR (T-16)

[00226] Table 17: This table discloses the compounds T-

17.01 to T-17.35 of the formula (T-17), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1.

F

F RNA F i / Rº Dr == N N F x -

N RR 6 RR RR (T-17)

[00227] Table 18: This table discloses the compounds T-

18.01 to T-18.35 of the formula (T-18), which are a compound of the formula (1) in which R !, R2, R3, R4, Ró and R6 have the specific meanings given in Table 1.

F CH RNA; R | Dr A "o No. 5 '6

RR RR ot (T-18)

[00228] Table 19: This table discloses the compounds T-

19.01 to T-19.35 of the formula (T-19), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1. H3C. : bV P RN F

N

F n oO RR 5 6 RR RR (T-19)

[00229] Table 20: This table discloses the compounds T-

20.01 to T-20.35 of the formula (T-20), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1. and F RNA F Rº ! DZ RR RR RR (T-20)

[00230] Table 21: This table discloses the compounds T-

21.01 to T-21.35 of the formula (T-21), which are a compound of the formula (1) in which R !, R2, R3, R4, Ró and R6 have the specific meanings given in Table 1. es Ro NO F Rº ! Z: the Rº RR R (T-21)

[00231] Table 22: This table discloses the compounds T-

22.01 to T-22.35 of the formula (T-22), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1. m and PN R 2 o RR RR RR (T-22)

[00232] Table 23: This table discloses the compounds T-

23.01 to T-23.35 of the formula (T-23), which are a compound of the formula (1) in which R !, R2, R3, R4, R & and R6 have the specific meanings given in Table 1. Rê Ss R. rr RF

NA VA SN '

RR R R (T-23)

EXAMPLES

[00233] The following Examples serve to illustrate the invention.

[00234] The compounds of the invention can be distinguished from known compounds by virtue of their greater effectiveness at low rates of application, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower rates of application if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[00235] 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).

[00236] Throughout this description, temperatures are given in degrees Celsius (ºC) and "mp." means melting point. LC / MS stands for Liquid Chromatography and Mass Spectroscopy and the description of the devices and method (Method A) is as follows: The description of the LC / MS device and method A is:

[00237] The spectra were recorded on a Waters Mass Spectrometer (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range : 30 V, Extractor: 2.00 V, Source Temperature: 150 ºC, Desolvation Temperature: 350 ºC, Cone Gas Flow: 50 L / h, Desolvation Gas Flow: 650 L / h, Mass Range : 100 to 900 Da) and a Waters UPLC Acquity: Binary pump, heated column compartment, diode array detector and ELSD detector. Column: UPLC HSS T3 by Waters, 1.8 um, 30 x 2.1 mm, Temp: 60 ºC, DAD wavelength range (nm): 210 to 500, Solvent Gradient: A = water + MeOH a 5% + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH; gradient: B at 10-100% in 1.2 min; Flow (mL / min) 0.85. The description of the LC / MS device and method B is:

[00238] The spectra were recorded on a spectrometer of

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

[00239] Where necessary, the 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, eg, use of chiral starting materials. Formulation Examples Wettable Powders a) b) Cc)

Active ingredient [composed of 25% 50% 75% Formula (1)] sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% diisobutylnaphthalenesulfonate - 6% 10% sodium phenol polyethylene glycol ether - 2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27% -

[00240] The active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a suitable mill, creating wettable powders that can be diluted with water to give suspensions of the desired concentration.

Powders for seed treatment aa) b) Cc) dry Active ingredient [25% compound 50% 75% Formula (1)] light mineral oil 5% 5% 5% highly dispersed silicic acid 5% 5% - Kaolin 65% 40 % - Talc - - 20%

[00241] The active ingredient is completely mixed with the adjuvants and the mixture is completely crushed in a suitable mill, creating powders that can be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of Formula 10% (1)] 3% octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 4 mol% of oxide ethylene) cyclohexanone 30% xylene mixture 50%

[00242] Emulsions of any required dilution can be obtained, which can be used to protect plants, from this concentrate by dilution with water.

Dusts a) b) Cc) Active ingredient [5% compound 6% 4% Formula (1)] Talc 95% - - Kaolin - 94% - mineral filling - - 96%

[00243] 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 coatings.

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

[00244] 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 (1)] 8% polyethylene glycol (p. Mol. 200) 3% Kaolin 89%

[00245] The finely crushed active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this way. Suspension concentrate Active ingredient [compound of Formula (1)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 6 mol% ethylene oxide) 10% sodium lignosulfonate

Carboxymethylcellulose 1% Silicone oil (in the form of a 1% emulsion 75% in water) Water 32%

[00246] The finely crushed active ingredient is intimately “mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by diluting 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.

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

[00247] The finely crushed active ingredient is intimately “mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by diluting with water. Using such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, spilling or immersion. Suspension of Slow Release Capsules

[00248] 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 complete.

[00249] The suspension of capsules obtained is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The Capsule Suspension Formulation contains 28% of the active ingredients. The average diameter of the capsules is 8-15 microns.

[00250] The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

List of Abbreviations: AIBN = azobisisobutyronitrile DMF = dimethylformamide DIBAL-H = diisobutyl aluminum hydride DIPEA = N, N-diisopropylethylamine EtOAc = ethyl acetate HCl = hydrochloric acid mp = melting point ºC = degrees Celsius MeOH = methyl alcohol NaOH = sodium hydroxide NBS = N-bromosuccinimide min = minutes TA = room temperature h = hour (s) TFAA = trifluoroacetic acid anhydride Preparation Examples Example 1: This example illustrates the preparation of 3 - [[4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methyl] -1,2,4-ethyl oxadiazol-5-carboxylate (Compound A.15 from Table A)

F F H; 3C Da A o N = o N

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

F OF N AS NADIA.

[00251] Under argon, to a solution of 3- [4- (bromomethyl) phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole (CAS 2093101-98-3; 1.0 g) in acetonitrile ( 10.0 mL) trimethylsilylformonitrile (420 mg) was added. Then, the mixture was cooled to 0 ° C and tetrabutylammonium hydrofluoride (1 M in THF, 4.2 ml) was added dropwise to the mixture. The yellow solution was then stirred at room temperature for 3 hours. Ice and water were added to the slightly exothermic reacted mixture. Then, the phases were separated and the aqueous layer was extracted twice with ethyl acetate, the organic layers were washed with water and then with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by chromatography using a cyclohexane / ethyl acetate gradient to give the title compound (0.82 g, 99% yield) as a white solid.

[00252] LC / MS (Method A) retention time = 1.01 minutes, 252 (M-H in negative mode).

[00253] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.18 (d, 2H), 7.54

(d, 2H), 3.88 (s, 2H).

[00254] 19F NMR (400 MHz, CDCl3) 5 ppm: -65.35 (s). Step 2: Preparation of N'-hydroxy-2- [4- [5- (trifluoromethyl) - 1,2,4-0xadiazol-3-yl] phenyl] acet-amidine “LCD F Not YA N — o F

[00255] 2- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl Jacetonitrile (100 mg) was dissolved in ethanol (1 mL) in a reflux condenser , then hydroxylamine hydrochloride (82 mg) was added, followed by N, N-diethylethanamine (0.165 ml). The mixture was stirred and heated to reflux for 4 hours. Almost total conversion was observed by LC / MS. An additional portion of hydroxylamine hydrochloride (27 mg) and N, N-diethylethanamine (0.055 ml) was added and the mixture was stirred for an additional 12 hours at 80 ° C. Then, heating was stopped and the reaction was allowed to cool to room temperature. The solvent was evaporated under reduced pressure to obtain a yellowish gum (113 mg). The crude product was used as such for the next step without further purification.

[00256] LC / MS (Method A) retention time = 0.66 minutes, 285 (M-H in negative mode).

Step 3: Preparation of ethyl 3 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -1,2,4-o0xadiazol-5-carboxylate

F F H3ãC Da A o = AN (O> o N

[00257] Under argon, to a solution of N'-hydroxy-2- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl crude Jacet-amidine (113 mg) in tetrahydrofuran (1.6 mL) was added dropwise with ethyl 2-chloro-2-0x0-acetate (162 mg). The mixture was stirred at room temperature for one day. Then, the solvent was evaporated. The residue was purified by chromatography using a cyclohexane / ethyl acetate gradient to give the title compound (91 mg, 63% yield) as a white solid.

[00258] Retention time: tr = 1.12min, M + H + = 369

[00259] LC / MS (Method A) retention time = 1.12 minutes, 369 (M + H).

[00260] 1 H NMR (400 MHz, CDCl 3) 5 ppm: 8.18 (d, 2H), 7.58 (d, 2H), 4.55 (q, 2H), 4.30 (s, 2H) , 1.47 (t, 3H).

[00261] 19F NMR (400 MHz, CDCl3) 5 ppm: -66.15 (s). Example 2: This example illustrates the preparation of N-propyl-3- [[4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methyl] -

1,2,4-0xadiazole -5-carboxamide (Compound A.1 from Table A)

F F ON à A N ON o o N

[00262] To a solution of ethyl 3 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -1,2,4-0xadiazol-5-carboxylate (Example 1, 85 mg) in ethanol (0.36 ml) propan-1-amine (8.3 mg) was added. The mixture was stirred at reflux temperature for 30 minutes. Then, the solvent was evaporated and the residue was purified by chromatography using a cyclohexane / ethyl acetate gradient to give the title compound (50 mg, 93% yield) as a white solid.

[00263] LC / MS (Method A) retention time = 1.07 minutes, 382 (M + H).

[00264] 'H NMR (400 MHz, CDCl3) 5 ppm: 8.20 (d, 2H), 7.76 (d, 2H), 7.00 (s, 1H, wide), 4.25 (s, 2H), 3.44 (q, 2H), 1.65 (m, 2H), 1.00 (t, 3H).

[00265] 19F NMR (400 MHz, CDCl3) 5 ppm: -66.16 (s). Example 3: This example illustrates the preparation of 3- [4 - [(2-methylthiazol-4-yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4-oxadiazole (Compound A.2 from Table A )

HJC no o F - Step 1: Preparation of 3- [4- (2-nitroprop-1-enyl) phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole

[00266] At 10 ° C, nitroethane (4.30 g) was added dropwise to a stirred solution of 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] benzaldehyde (CAS 2093101- 98-3; 2.00 9g) and ammonium acetate (1.58 g) in acetic acid (16.0 mL). The mixture was stirred at 100 ° C for 90 minutes. Then the mixture was allowed to cool to room temperature and was poured into cold water (200 ml), then ethyl acetate (100 ml) was added. The organic phase was washed successively with water (2 x 100 ml), saturated aqueous sodium bicarbonate solution (2 x 100 ml) and water (100 ml). The organic phase was separated and dried over anhydrous magnesium sulfate and evaporated to give the title compound (2.35 9, 88% yield) as a yellow oil which crystallized upon standing. The crude product was pure enough for the next step without further purification.

[00267] In order to obtain a pure sample, the crude product (200 mg) was subjected to flash chromatography on silica gel (4 g pre-packaged column) with a 100: 0 cyclohexane / ethyl acetate gradient 95: 5 as eluent. The fractions with the pure product were combined and evaporated. 130 mg of pure product was recovered as a light yellow solid, mp = 75-88 ° C.

[00268] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.22 (d, 2H), 8.10 (s, 1H), 7.58 (d, 2H), 2.47 (s, 3H)

[00269] 21ºF NMR (400 MHz, CDCl3) 5 ppm: -65.33 (s). Step 2: Preparation of 1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] propan-2-one CH; VS F

AQ IT IS

[00270] A solution of 3- [4- (2-nitroprop-11-enyl) phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole (0.96 g) in trifluoroacetic acid (12 mL) was stirred vigorously at 75 ° C (reflux). Powdered iron (0.65 g) was added in one portion and the mixture was stirred 1 h at reflux. Then, the reaction mixture was cooled to 0 ° C, filtered over celite and the solvent evaporated. Then, water was added and the mixture was extracted three times with dichloromethane. The combined organic phases were washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane / ethyl acetate 99: 1 to 8: 2 as eluent. Fractions with the pure product were combined and evaporated to give the title compound (0.33 g, 41% yield) as an orange solid.

[00271] LC / MS (Method A) retention time = 1.04 minutes, 271 (M + H).

[00272] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.12 (d, 2H), 7.40 (d, 2H), 3.82 (s, 2H), 2.25 (s, 3H)

[00273] 21ºF NMR (400 MHz, CDCl3) 5 ppm: -65.33 (s). Step 3: Preparation of 1-bromo-3- [4- [5- (trifluoromethyl) - 1,2,4-0xadiazol-3-yl] phenyl] propan-2-one. Br AR F

F

[00274] 1- [4- [5- (Trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] propan-2-one (2.00 g) was dissolved in acetic acid (6.2 mL ). A solution of HBr in acetic acid (33%, 2.0 ml) was added dropwise at room temperature. Then, bromine (2.4 g) and the reaction mixture was added dropwise. The resulting thick, dark brown suspension was stirred for 3 hours at room temperature. Then, acetone (12 ml) was added and the solution was stirred for 5 hours at room temperature. The solvent was evaporated and extracted with dichloromethane and water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel using a cyclohexane / ethyl acetate gradient as the eluent. Thus, the title compound was obtained as a pale yellow solid (1.80 g, 70% yield).

[00275] LC / MS (Method A) retention time = 1.10 minutes, 347 (M-H in negative mode).

[00276] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.12 (d, 2H), 7.42 (d, 2H), 4.10 (s, 2H), 3.98 (s, 2H) Step 4: Preparation of 3- [4- [(2-methylthiazol-4-yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4-0xadazole H; 3C N — OF -

[00277] Bromo-3- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] propan-2-one (200 mg) was dissolved in ethanol (9 ml). Then, thioacetamide (47 mg) was added and the resulting solution was heated to reflux for 18 hours. Then, the solvent was evaporated and the residue was purified by chromatography on silica gel using a cyclohexane / ethyl acetate gradient as eluent. . Thus, the title compound was obtained as a solid (112 mg, 60% yield), mp = 46.1-48.2 ° C.

[00278] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.08 (d, 2H), 7.42 (d, 2H), 6.71 (s, 1H), 4.19 (s, 2H), 2.71 (s, 3H)

Example 4: This example illustrates the preparation of 3- [4- [1- fluoro-1- (3-methylisoxazol-5-yl) ethyl] phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole (Compound A.3 of Table A) H3C NS F o F CH; Step 1: Preparation of 1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] prop-2-en-1-ol Ho F A;

AO TJ F

[00279] To a solution of 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] benzaldehyde (CAS 2093101-98-3; 1.60 g) in tetrahydrofuran (22.0 ml) at -78 ºC under argon, vinylmagnesium bromide (1.00 mol / L solution in tetrahydrofuran, 9.91 ml) was added. The reaction mixture was stirred for 40 minutes at -78 ° C. Then, the reaction mixture was quenched by adding a saturated aqueous solution of ammonium chloride and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water, then with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel using cyclohexane / ethyl acetate as the eluent to give the title compound (0.60 g,

33%) as a white solid.

[00280] LC / MS (Method A) retention time = 1.03 minutes, 271 (M + H).

[00281] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.15 (d, 2H), 7.60 (d, 2H), 6.07 (m, 1H), 5.44 (d, 1H), 5.30 (m, 2H).

[00282] 21ºF NMR (400 MHz, CDCl3) 5 ppm: -65.34 (s). Step 2: Preparation of (3-methyl-4,5-dihydroisoxazol-5-yl) - [4- [5- (tri fluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl methanol

HO o F AA, H3C

[00283] To a solution of 1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] prop-2-en-1-ol (100 mg) in dichloromethane (3 , 70 ml) propan-2-ol (0.094 ml) was added. The solution was cooled to 0 ºC under argon followed by the addition of ethylmagnesium bromide in THF (1.00 mol / L in tetrahydrofuran, 1.11 ml). The reaction mixture was stirred for 30 minutes at 0 ° C and a solution of N-hydroxyacetimidoyl chloride (45 mg) in dichloromethane (1.5 ml) was added slowly. The reaction mixture was gradually warmed to room temperature and stirred for 12 hours. A saturated solution of NH.Cl was then added, and the solution was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel using cyclohexane / ethyl acetate as the eluent to give the title compound (40 mg, 33% yield) as a white solid. LC / MS and 1H NMR show a mixture of diastereoisomers in a ratio close to 1: 1.

[00284] LC / MS (Method A) retention time = 0.93 and 0.94 minutes, 328 (M + H).

[00285] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.07 (d, 2H), 7.50 and 7.48 (two d, together 2H), 5.10 and 4.60 (two d, together 1H), 4.74 and 4.68 (two m, together 1H), 2.90 (m, 1H), 2.72 and 2.58 (two m, together 1H), 1.92 and 1.90 (two s, together 3H).

[00286] 19F NMR (400 MHz, CDCl3) 5 ppm: -65.33 (s). Step 3: Preparation of (3-methylisoxazol-5-yl) - [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methanone o

KUIDIE = N = F He Ro A.

[00287] To a solution of (3-methyl-4,5-dihydroisoxazol-5-yl) - [4- [5- (tri-fluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methanol (110 mg) in toluene (6.7 ml) manganese (IV) oxide (584 mg) was added. The reaction mixture was heated for 2 hours at reflux. Then the mixture was allowed to cool to room temperature, was filtered through a pad of celite, washed with dichloromethane / methanol 9/1 and concentrated. The residue was purified by chromatography on silica gel using cyclohexane / ethyl acetate as the eluent to give the title compound (60 mg, 55% yield) as a white solid.

[00288] LC / MS (Method A) retention time = 1.12 minutes, 324 (M + H).

[00289] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.30 (s, 4H), 6.94 (s, 1H), 2.45 (s, 3H).

[00290] 19F NMR (400 MHz, CDCl3) 5 ppm: -65.25 (s). Step 4: Preparation of 1- (3-methylisoxazol-5-yl) -1- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl ethanol Ho, FA: N 7> the RO. and

F

[00291] (3-Methylisoxazol-5-1yl) - [4- [5- (trifluoromethyl) - 1,2,4-0xadiazol -3-yl] phenyl methanone (400 mg) was dissolved in tetrahydrofuran (5 ml ) and cooled to -78 ºC. Methylmagnesium chloride (3.0 mol / L solution in tetrahydrofuran, 1.8 mL) was added slowly. The mixture was stirred at -78 ° C for 75 minutes, then allowed to warm to room temperature, saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate.

The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude residue was purified by chromatography on silica gel, using a cyclohexane / ethyl acetate gradient as the eluent, to give the title compound as an oil (186 mg, 47% yield).

[00292] LC / MS (Method A) retention time = 1.01 minutes, 381 (M + H + acetonitrile).

[00293] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.10 (d, 2H), 7.64 (d, 2H), 6.05 (s, 1H), 3.35 (wide s, 1H) , 2.30 (s, 3H) 1.96 (s, 3H).

Step 5: Preparation of 3- [4- [1-fluoro-1- (3-methylisoxazol-5-yl) ethyl] phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole H3C NO F [2- € Er the F CH;

[00294] Under an argon atmosphere, a solution of 1- (3-methylisoxazol-5-yl) -1- [4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] -phenyl ] ethanol (55 mg) in dichloromethane (3 mL) is cooled to 0 ºC. N-ethyl-N- (trifluorosulfanyl) ethanamine (44 mg) was added and the mixture was allowed to warm up to room temperature. After 2 hours, the mixture is poured into saturated aqueous sodium bicarbonate, extracted with ethyl acetate, the organic phase dried over anhydrous sodium sulfate, filtered and evaporated. The residue is purified by chromatography on silica gel, using a gradient from pure cyclohexane to cyclohexane / ethyl acetate (95: 5) as the eluent. Thus, the title compound was obtained as a colorless oil (34 mg, 62% yield).

[00295] LC / MS (Method A) retention time = 1.16 minutes, 342 (M + H).

[00296] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.17 (d, 2H), 7.62 (d, 2H), 6.10 (s, 1H), 2.32 (s, 3H), 2.13 (d, 3H).

[00297] 19F NMR (400 MHz, CDCl3) 5 ppm: -65.35 (s), -141.39 (s). Example 5: This example illustrates the preparation of 3- [4 - [(2,4-dimethylthiazol-5-yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4-oxadiazole (Compound A.13 of Table A) H3C k N — O

FE NES / A - N F

E H3C Step 1: Preparation of 3 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] pentane-2,4-dione

FE N. F H3C NS o Y F HC N — O

[00298] To a stirred solution of pentane-2,4-dione (245 mg) in acetonitrile (16 ml), potassium carbonate (341 mg) was added in portions at room temperature. The white suspension was stirred for 15 min. Then, a solution of 3- [4- (bromomethyl) phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole (CAS 2093101-98-3; 500 mg) in acetonitrile (2 ml) was added. The resulting mixture was heated to reflux overnight, then allowed to cool to room temperature, filtered to remove the solids, and the filtrate was concentrated under reduced pressure to give a brown oil. This residue was purified by chromatography on silica gel, using a cyclohexane / ethyl acetate gradient as the eluent. Thus, the title compound was obtained as a yellow oil (243 mg, 46% yield). Tautomeric forms (keto- and enol forms) are visible in LC / MS and NMR.

[00299] LC / MS (Method A) retention time = 1.07 and 1.17 minutes, both 325 (M-H in negative mode). Step 2: Preparation of 3-bromo-3 - [[4- [5- (trifluoromethyl) - 1,2,4-0xadiazol-3-yl] phenyl] methyl] -pentane-2,4-dione F

N F

ACO SN o N — O H3C

[00300] In a mortar, 3 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] pentane-2,4-dione (300 mg) was ground in together with N-bromosuccinimide (165 mg) for 5 minutes. The mixture first solidified and then melted again. The oil was left to stand for 1 hour. Then, the reaction mixture was extracted with water and dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel, using a cyclohexane / ethyl acetate gradient as the eluent. Thus, the title compound was obtained as a colorless oil (294 mg, 78% yield).

[00301] LC / MS (Method A) retention time = 1.19 minutes, 405, 407 (M + H).

[00302] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.08 (d, 2H), 7.41 (d, 2H), 3.60 (s, 2H), 2.31 (s, 6H) Step 3: Preparation of 3-bromo-4- [4- [5- (trifluoromethyl) - 1,2,4-0xadiazol-3-yl] phenyl] butan-2-one

H3C Br Dr

[00303] Silica gel (5.0 g) was suspended in dichloromethane (70 ml). To this suspension, a solution of chlorosulfonic acid (1.5 ml) in dichloromethane (10 ml) was added dropwise with a syringe. The mixture was stirred for 20 minutes at room temperature. Then, a solution of 3-bromo-3 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -pentane-2,4-dione (2.0 9g) in dichloromethane (10 ml) was added dropwise, and the reaction mixture was stirred for 2 hours at room temperature. Then, the reaction mixture was filtered over a small amount of silica gel and evaporated. Thus, the title compound was obtained in pure form as a yellow oil (1.63 g, 91% yield).

[00304] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.07 (d, 2H), 7.38 (d, 2H), 4.50 (t, 1H), 3.53 (dd, 1H), 3.23 (dd, 1H), 2.37 (s, 3H). Step 4: Preparation of 3- [4 - [(2,4-dimethylthiazol-5-yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole H3C N — O - N F

F H3C

[00305] 3-Bromo-4- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] butan-2-one (300 mg) was dissolved in ethanol (10 ml) . Then, thioacetamide (68 mg) was added and the solution was heated to reflux for 18 hours. Then, the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, using a cyclohexane / ethyl acetate gradient as the eluent. Thus, the title compound was obtained as a white solid

(89 mg, 31% yield), mp = 88-91 ° C.

[00306] LC / MS (Method A) retention time = 1.15 minutes, 340 (M + H).

[00307] 'H NMR (400 MHz, CDCl3) 5 ppm: 8.05 (d, 2H), 7.32 (d, 2H), 4.10 (s, 2H), 2.62 (s, 3H) , 2.36 (s, 3H). Example 6: This example illustrates the preparation of 5- (trifluoromethyl) -3- [4 - [[5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] 1methyl] phenyl] -1,2,4 -o0xadiazole (Compound A.21 from Table A)

F F

F AO Step 1: Preparation of 4- (2-amino-2-hydroxy-imino-ethyl) -N'-hydroxy-benzamidine

CD in ”N = oH

[00308] In a flask equipped with a condenser, 4- (cyanomethyl) benzonitrile (100 mg) was dissolved in ethanol (1.8 ml), then hydroxylamine hydrochloride (147 mg) was added, followed by N, N-diethylethanamine ( 0.294 ml). The reaction was stirred and heated to reflux for 2 hours. Then, heating was stopped and the reaction was allowed to cool to room temperature. The solvent was evaporated under reduced pressure to obtain a white gum. The crude product was used as such for the next step without further purification.

[00309] LC / MS (Method A) retention time = 0.17 minutes, 209 (M + H). Step 2: Preparation of 5- (trifluoromethyl) -3- [4 - [[5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] methyl] phenyl] -1,2,4- oxadiazole

F F

[00310] Under argon, a solution of crude 4- (2-amino-2-hydroxyimino-ethyl) -N'-hydroxy-benzamidine (146 mg) in tetrahydrofuran (2.8 ml) dropwise (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate (0.293 ml). The mixture was stirred at room temperature for one day. Then, the solvent was evaporated and the residue was purified by chromatography using a cyclohexane / ethyl acetate gradient to give the title compound (72 mg, 28% yield) as a colorless oil.

[00311] LC / MS (Method A) retention time = 1.20 minutes, 363 (M-H in negative mode).

[00312] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.13 (d, 2H), 7.52

(d, 2H), 4.30 (s, 2H).

[00313] 19F NMR (400 MHz, CDCl3) 5 ppm: -65.40 (s). Example 7: This example illustrates the preparation of 5-methyl-4- [[4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methyl] -1H-pyrazol-3-ol (Compound A.22 from Table A) N. oH N — O EO dé = NF H3C F

[00314] In a microwave flask, 3- [4- (bromomethyl) phenyl] -5- (trifluoromethyl) -1,2,4-0xadiazole (CAS 2093101-98-3; 150 mg), 5-methyl -1H-pyrazol-3-ol (68 mg) and potassium carbonate (130 mg) were added to acetonitrile (4.6 ml). The resulting white suspension was heated in the microwave for 15 min at 110 ° C. Then, the solids were removed by filtration, washed with ethyl acetate and the combined filtrates evaporated. The residue was purified by preparative reverse phase HPLC. Thus, the title compound was obtained as a solid (12 mg, 8% yield), mp = 129.1-142.3 ° C.

[00315] LC / MS (Method A) retention time = 0.91 minutes, 325 (M + H).

[00316] 'H NMR (600 MHz, CDCl3) 5 ppm: 7.90 (d, J = 8.2 Hz, 2H), 7.25 (d, J = 8.2 Hz, 2 H), 3, 67 (s, 2H), 2.07 (s, 3 H).

[00317] 2 * C NMR (151 MHz, CDCL3) 5 ppm: 168.9 (s, 1 CO), 165.7 (q, J = 44 Hz, 1 C), 160.5 (s, 1 C) , 144.9 (s, 1 CO),

142.7 (s, 1C), 128.8 (s, 2 C), 127.7 (s, 2 C), 122.7 (s, 1 Cc), 116.0 (q, J = 274 Hz, 1 C), 101.5 (s, 1 C), 27.4 (s, 1 CO), 10.6 (s, 1 C). Example 8: This example illustrates the preparation of 5- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl] methyl] -4,5-dihydroisoxazol-3-carboxylate ethyl (Compound B.1 of Table B) Ro FE o wo Step 1: Preparation of 4-allyl-N-hydroxy-benzamidine AX "N = oH

[00318] To a solution of 4-allyl benzonitrile (2.0 g) in ethanol (56 ml) was added an aqueous solution of hydroxylamine (50%, 3.4 ml). The reaction mixture was stirred for 18 hours at 55 ° C. Ethanol was evaporated under reduced pressure and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give the title compound as a white solid. The crude product thus obtained was used for step 2 without further purification.

[00319] 'H NMR (400 MHz, CDCl3) 5 ppm: 7.50 (d, 2H), 7.14 (d, 2H), 6.60 (s, broad, 1H), 5.88 (m, 1H), 5.05 (m, 1H) 5.00 (m, 1H), 4.92 (s, broad, 2H), 3.32 (d, 2H). Step 2: Preparation of 3- (4-allylphenyl) -5- (trifluoromethyl) - 1,2,4-0xadiazole

F = N. F N — O

[00320] To a solution of 4-allyl-N-hydroxy-benzamidine (2.50 g) in tetrahydrofuran (42.6 ml) was added dropwise (2,2,2-trifluoroacetyl) 2,2, 2-trifluoroacetate (2.81 ml). The reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was quenched by adding a saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (3.8 g) as a yellow solid. The crude product thus obtained was used for step 3 without further purification.

[00321] 'H NMR (400 MHz, CDCl3) 5 ppm: 8.00 (d, 2H), 7.30 (d, 2H), 5.93 (m, 1H), 5.09 (m, 2H) , 3.40 (d, 2H).

[00322] 1st F NMR (400 MHz, CDCl3) 5 ppm: -65.38 (s). Step 3: Preparation of 5 - [[4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -4,5-dihydroisoxazol-3-

ethyl carboxylate Ro F E Ao o Nº

[00323] To a solution of 3- (4-allylphenyl) -5- (trifluoromethyl) -1,2,4-0xadiazole (200 mg) in ethyl acetate (3.93 ml) was added 2-chloro-2- hydroxyimino-ethyl acetate (131 mg) followed by sodium bicarbonate (218 mg). The reaction mixture was stirred for 1 day at room temperature. Then, the mixture was filtered and the residue washed with ethyl acetate. The combined filtrates were concentrated and purified by chromatography on silica gel using cyclohexane / ethyl acetate as the eluent to give the title compound (250 mg, 86% yield) as a white solid.

[00324] LC / MS (Method A) retention time = 1.12 minutes, 370 (M + H).

[00325] 'H NMR (400 MHz, CDCl3) 5 ppm: 8.00 (d, 2H), 7.32 (d, 2H), 5.02 (m, 1H), 4.25 (q, 2H) , 3.20 (dd, 1H), 3.08 (dd, 1H), 2.93 (dd, 1H), 2.88 (dd, 1H), 1.28 (t, 3H).

[00326] 1st F NMR (400 MHz, CDCl3) 5 ppm: - 65.35 (s). Example 9: This example illustrates the preparation of 3- [4- [5- (trifluoromethyl) -1,2,4-0xadiazol-3-yl] phenyl methyl] imidazo [2,1-b] thiazol-6-carboxylate methyl

(Compound C.3 of Table C) "Ss, the NE

L F

[00327] To a solution of 1-bromo-3- [4- [5- (trifluoromethyl) - 1,2,4-0xadiazol -3-yl] phenyl] propan-2-one (Example 3, Step 3; 1 , 0 g), in ethanol (17 mL), methyl 2-thioxo-1,3-dihydroimidazole-4-carboxylate (525 mg) was added at room temperature, then the resulting solution was heated after reflux for 2 hours . Then the mixture was allowed to cool to room temperature, the solvent evaporated, and the residual solid was suspended in 2,2,2-trifluoroacetate (2,2,2-trifluoroacetyl) (8.0 mL) under cooling with a water bath. The mixture was stirred at room temperature for 3 days, then the solvent evaporated, the residual brown oil was added dropwise to water. The aqueous suspension was made basic by the addition of potassium carbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on silica gel, using a gradient from dichloromethane (100%) to dichloromethane / methanol (92: 8) as a solvent. Thus, the title compound (0.92 g, 79% yield) was obtained with a solid.

[00328] LC / MS (Method A) retention time = 1.04 minutes, 409 (M + H).

[00329] 1H NMR (400 MHz, CDCl3) 5 ppm: 8.25 (d, 2H), 7.86 (s, 1H), 7.44 (d, 2H), 6.63 (s, 1H), 4.20 (s, 2H), 3.92 (s, 3H).

[00330] 1ºF NMR (400 MHz, CDCl3) 5 ppm: - 65.36 (s). Table A: Melting point data (mp) and / or LC / MS (retention time (tr)) for compounds of Formula (1): Methane loading Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.1 N-propyl-3 - [[4- r

F [5- Da 1.07 382 A ks o (trifluoromethyl LT "

HN -1,2,4- (oxadiazol-3-yl] phenyl] methyl] -1,2,4- oxadiazole-5-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.23- [4 - [(2- 46, No methylthiazole-4- A 1- - F

N yl) methyl] phenyl] Y f 48, -5- 2 (trifluoromethyl) -1,2,4- oxadiazole A.33- [4- [1-fluoro- F Ne 1.16 342 A = A 1- ( 3- R vo and methylisoxazol-5-yl) ethyl] phenyl] - 5- (trifluoromethyl) -1,2,4- oxadiazole A.43- [4- [1-fluoro- F No 1.21 356 A 1- (3- -, OA

SE F methylisoxazole-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS 5-yl) propyl] phenyl 1-5- (trifluoromethyl) -1,2,4-oxadiazole A.53- [4- [1-fluoro-Fne 1,26 370 A 2-methyl-1- (3 - = A So and methylisoxazol-5-yl) propyl] phenyl 1-5- (trifluoromethyl) -1,2,4- oxadiazole A.6 N - [[4-methyl-5-ne and 102 = F [[4- [5- A - A 8 (trifluoromethyl &, -

A -1,2,4- O 104

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS oxadiazol-3- 8 yl] phenyl] methyl] thiazol-2-yl] methyl] carbam tert-butyl A.72- [4-methyl-5- Ne 95

AF [[4-15- and DA: (trifluoromethyl XX 97,) -1,2,4- 1 oxadiazol-3-yl] phenyl] methyl] thiazol-2-yl] Jacetonitrile A.83- [4 - [( 4-methyl- No 181 0 2-0xazol -2-yl- A 12 thiazol-5- S - yl) methyl] phenyl] 185 -5- 2

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS (trifluoromethyl) -1,2,4- oxadiazole A.93- [4 - [[4-methyl- Ne 1.27 394 A

2. DA SF Ff (trifluoromethyl À,) thiazol-5-yl] 1methyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole A.13- [4- [fluoro- F N. 1,11 . 328 A> F o (3- Ç & O A (So and methylisoxazol-5-yl) methyl] phenyl] -5- (trifluoromethyl

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS) -1,2,4- oxadiazole A.13- [4- [difluoro- et Ne 63 1 G- & 7 A. So F methylisoxazol-64 5-yl) methyl] phenyl] -5- (trifluoromethyl) - 1,2,4- oxadiazole A.14-methyl-5 - [[4- N, 1.19 398 AX (O> F 2 [5- * À (trifluoromethyl oo) -1,2,4- oxadiazole-3 - yl] phenyl] methyl] thiazol-2-carboxylate

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS ethyl A.13- [4 - [(2,4- No 88 3 dimethylthiazole- IDA: -

SS F 5- Y 91 il) methyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole A.13- [4 - [(4- No 1.12 326 AAY <A Ff 4 methylthiazole-5 - and Das il) methyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.13 - [[4- [5- er 1.12 369 A

F (trifluoromethyl dd o Oo k ee OO o oxadiazol-3-) yl] phenyl] methyl] -1,2,4-oxadiazol-5-ethyl carboxylate A.13- [4 - [(4-methyl- Ne. 80, 6 2-phenyl-thiazol-YA O Aa 1- 5- & S 83, yl) methyl] phenyl] 9 -5- (trifluoromethyl) -1,2,4- oxadiazole

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.13- [4 - [(2-ethyl- Ne 1.20 354 A 7 4-methyl-thiazole-YA O.

X F 5- yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole A.1N, 4-dimethyl-5- Ne 200 and F 8 [[4- [5- A - do -

NY F (trifluoromethyl x 220) -1,2,4-oxadiazol-3-yl] phenyl] methyl] thiazol-2-amine A.14-methyl-5 - [[4- No 0.86 341 A

A ”Ss Ad (trifluoromethyl no.) -1,2,4-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS oxadiazol-3-yl] phenyl] methyl] thiazol-2-amine A.25- et 1.25 377 A

F O (trifluoromethyl Da [M-H] -

F ON SN) -3- [4- [1- [5- ES in

F (trifluoromethyl mode) -1,2,4- negati oxadiazol-3-yl ylmethyl] phenyl] - 1,2,4-0xadiazole A.25- rr 1.20 363 A

F 1 (trifluoromethyl = [M-H] -

FF ON SN) -3- [4 - [[5- AA) in

F (trifluoromethyl mode) -1,2,4- negati oxadiazol-3-yl] 1methyl] phenyl] -1,2,4-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS oxadiazole A.2 5-methyl-4 - [[4- Ne. 129 2 [5- = - Ace to 7 oH F (trifluoromethyl -) -1,2,4- 142 oxadiazol-3- 3 yl] phenyl] methyl] -1H-pyrazol-3-ol A.2 N-prop -2-inil- No

PF 3 5 - [[4- [5- FROG IS (trifluoromethyl) -1,2,4- oxadiazole-3- 0.98 378 A il] phenyl] methyl] -1,2,4- oxadiazole-3- carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.2 N-ethyl-N-methyl- Na 4 2 - [[4- [5-. as (trifluoromethyl) -1,2,4- o 1,7 397,01 B oxadiazole-3-LF

Fyl] phenylmethyl] Ff thiazol-4-carboxamide A.2 N-prop-2-ynyl- = o 2 - [[4- [5- Hds à (trifluoromethyl) -1,2,4- o 1,65 392 97 B oxadiazole-3 READ

Phyl] phenyl methyl] Ff thiazole-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.2 N-tert-butyl-2- N o 6 [[4- [5- "(trifluoromethyl%) -1,2,4- Ns 1,94 411,03 B oxadiazol-3- Da il) phenyl methyl] “À; thiazole-4-carboxamide A.2N- (2- oo 7 furylmethyl) -2- Dx [[4- [5- a (trifluoromethyl) -1,2,4- + 1,78 435,01 B oxadiazol-3-Fryl] phenyl] methyl] thiazol-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.2 N-cyclopentyl- 8 2 - [[4- [5- Q Pp (trifluoromethyl A

SS) -1,2,4- 1,91 423,04 B oxadiazole-3 o? ; e-N il] phenyl] methyl] Á

FF thiazole-4-carboxamide A.2 N-methoxy-2 - [[4- - o 9 [5- Hs Ss (trifluoromethyl) -1,2,4- [E 1,51 384,97 B oxadiazole-3- READ

Phyl] phenyl methyl] Ff thiazole-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.3 N-ethoxy-2 - [[4- Yo, o Ace (trifluoromethyl O) -1,2,4- o 1,6 398,99 B oxadiazole-3- READ

F ill] phenylmethyl] Fr thiazol-4-carboxamide A.3 N-cyclobutyl-2- 1 [[4- [5- q,

H (trifluoromethyl as) -1,2,4- 1,83 409,01 B oxadiazol-3- <- yl] phenyl] methyl] dd thiazol-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.3 N-benzyl-2 - [[4- 2 [5- $ |

HNLO (trifluoromethyl DS

NW 1-1,2,4- ADA FP 1,89 445,04 B oxadiazol-3-yl] phenyl] methyl] thiazol-4-carboxamide A.3 N-phenyl-2 - [[4- F, 3 [ 5- es S (trifluoromethyl Q, N) -1,2,4- LL? 1.95 431.02 B oxadiazol-3-yl] phenyl] methyl] thiazol-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.3N, N-diethyl-2- —n o 4 [[4- [5- IA as (trifluoromethyl) -1,2,4- o 1,81 411.04 B oxadiazole-3- Va

F illfenillmetil] Ff thiazole-4-carboxamide A.3 N-isobutyl-2- [[4- [5-! o (trifluoromethyl o) -1,2,4- o 1,88 411.04 B oxadiazole-3 Pa

F ill] lfenillmetil] Fr thiazol-4-carboxamide

Load Méto Ent tr da mp Name of rad Structure (min) mass (ºC compound q of a 4 + H1 +

LCMS A.3N-allyl-2 - [[4- t% X o 6 [5- n (trifluoromethyl *) -1,2,4- o 1,73 394,99 B oxadiazol-3-Fº ill] phenylmethyl] Fr thiazol-4-carboxamide A.3 N-cyclohexyl-FE,

O F 7 2 - [[4- [5- O. es (trifluoromethyl “x o

É) -1,2,4- 2,01 437,06 B oxadiazol-3-yl] phenyl] methyl] thiazole-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.3 N-methoxy-N- - o 8 methyl-2 - [[4- [5-. as (trifluoromethyl) -1,2,4- o 1,62 398,99 B oxadiazole-3-LF

Fyl] phenylmethyl] Ff thiazole-4-carboxamide A.3 N-isopropyl-2- À o 9 [[4- [5- A (trifluoromethyl O) -1,2,4- Ns 1,78 397 B oxadiazole- 3- ryl] phenyl] methyl] "À; thiazole-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.4 N- (2,2-

IN O dimethylpropyl) - A 2 - [[4- [5- o (trifluoromethyl -1,2,4- Da 1.98 425.05 B oxadiazol-3-Fryl] phenyl] methyl] thiazole-4-carboxamide A .4 N-sec-butyl-2- A o 1 [[4- [5- A (trifluoromethyl O) -1,2,4- Nes 1,88 411,03 BB oxadiazol-3- Da yl] phenyl methyl] “À; thiazole-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.4 N, N-dimethyl-2- RO o A F 2 [[4- [5- Hage

V (trifluoromethyl) -1,2,4- 1,58 382,99 B oxadiazol-3-yl] phenyl] methyl] thiazol-4-carboxamide A.4 N- (2- RF Ls by 3 methoxyethyl) -2- o / AQ [[4- [5- (trifluoromethyl 80) -1,2,4- 7 oxadiazol-3- 85 yl] phenyl] methyl] thiazol-4-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.4 N-ethyl-2 - [[4- Fº FL to 4 [5- L ”o

SÁ LO (trifluoromethyl 73) -1,2,4- 1,65 382,99 B - oxadiazol-3- 80 yl] phenyl] methyl] thiazol-4-carboxamide A.4 N-methyl-2 - [[4- The. Ps Da 5 ”AD (trifluoromethyl 148) -1,2,4- 1,57 368,97 B - oxadiazol-3- 152 yl] phenyl] methyl] thiazol-4-carboxamide A.4 N-cyclopropyl- $ ex 6 2 - [[4- [5- DATA 1.68394.99 B (trifluoromethyl

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS) -1,2,4- oxadiazol-3-yl] phenyl] methyl] thiazol-4-carboxamide A.42 - [[4- [5- nt 7 (trifluoromethyl AA LO) -1,2,4- oxadiazole -3- 1.13 384 Ethyl A] phenyl] methyl] thiazole-4-carboxylate A.4 N-cyclopropyl- OA, | F 8 5 - [[4- [5- Po E E 124 (trifluoromethyl) -1,2,4-130 oxadiazol-3-yl] phenyl] methyl]

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS -1,2,4- oxadiazole-3-carboxamide A.4 acid 5 - [[4- [5- O,

N NA 9 (trifluoromethyl & aa oH o) -1,2,4- oxadiazole-3- 0.84 341 A yl] phenyl] methyl] -1,2,4-oxadiazole-3-carboxylic A.55 - [[ 4- [5- 1

F O (trifluoromethyl VA No) -1,2,4- Ç 145 oxadiazol-3-yl] phenyl] methyl] 152 -1,2,4-oxadiazol-3-carboxylate

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS ethyl A.53- [4- (ti 1-4- [4- (thiazo No, 1 ylmethyl) phenill- FA - AX

SN 5- 1.09 312 A (trifluoromethyl) -1,2,4- oxadiazole A.53- [4- [1-fluoro- F Ne = F 2 3-methyl-1- (3- & - A

N methylisoxazol-5-yl) but-3- 1,26 382,5 A enyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole A.5 N-propyl-2 - [[4- RF o 3 [5- ÃO e "x 1.78 397.01 B (trifluoromethyl) -1,2,4-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS oxadiazol-3-yl] phenyl] methyl] thiazol-4-carboxamide A.5 acid 2 - [[4- [5- Ré g - 4 (trifluoromethyl AA Sis) -1,2,4- oxadiazole-3- 0 , 98 356 Ayl] phenyl] methyl] thiazol-4-carboxylic A.52- [4 - [[4- [5- = F (trifluoromethyl A Ad) -1,2,4- R 98, oxadiazole-3- 1- yl] phenyl] methyl] 100 thiazol-2-yl] Jacetonitrile

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.5 N - [[4 - [[4- [5- No., = X F 6 (trifluoromethyl A A

SN F) -1,2,4- q, AMK 76, oxadiazol-3- 8-yl] phenyl] methyl] 78, thiazol-2- 2 yl] methyl] carbam tert-butyl A.53- [4 - [(2- DN.

A A 7 phenylthiazole-4 FA of SN 72, il) methyl] phenyl] Ó 3 - -5- 75, (trifluoromethyl 1) -1,2,4- oxadiazole

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS A.54 - [[4- [5- [[4- [o 8 (trifluoromethyl to Sed) -1,2,4- Lx 93, oxadiazol-3- 6 - yl] phenyl] methyl] 95, thiazole- 2- 1 ethyl carboxylate A.54 - [[4- [5- No mm AA + 113 9 (trifluoromethyl O, x 7) -1,2,4- Ns oxadiazol-3- 115 yl] phenyl] methyl] 1st thiazol-2-amine A.6N-methyl-4 - [[4- N 126

A O A O [5- s fr 9º (trifluoromethyl Hm -) -1,2,4- 128 oxadiazole-3- 3

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS il] phenyl] methyl] thiazol-2-amine Table B: Melting point data (mp) and / or LC / MS (retention time (tr)) for compounds of Formula (1): Methane loading mp Name of rad Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS B.1 5 - [[4- [5- F 1.12. 370 A

F (trifluorome -

SO useful) -1,2,4- N; o oxadiazol-3- + r illfeniltimet - 27º il] -4,5-dihydroisoxazo 1-3-carboxylate

Load Méto Ent tr da mp Name of rad (min) mass (ºC composed of a) [MH]:)

Ethyl LCMS B.25- 104

FF (trifluorome X - the tilde) -3- [4- N 106 [[13- À o (trifluorome e) = n

F til) -4,5-di- F hydroisoxazo 1-5-yl] methyl] phenyl] -1,2,4-oxadiazole B.3 3- [4- (3- 54 O: (ethyl-4, 5- X - Ss o di- N 57 hydroisoxazo 9 1-5- N yl) methyl] phenyl] -5-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS (trifluorome til) -1,2,4- oxadiazole B.4 3- [4- (3- 77

FF (methyl-4,5-A - = di- N 80 hydroisoxazo

O 1-5- = N yl) methyl] phenyl] -5- (trifluoromethyl) -1,2,4- oxadiazole B.5 N-ethyl-N-

Ç methyl-5 - [[4- ATX, E + F 1.66383.07 B (trifluoromethyl) -1,2,4- oxadiazole-3-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS il] phenyl metyl] -4,5-dihydroisoxazo 1-3-carboxamide B.6 N-prop-2- o N vo = N inyl-5 - [[4- TO

FF (trifluoromethyl) -1,2,4-oxadiazole-3- 1,58 379,04 Byl] phenyl] methyl] -4,5-dihydroisoxazo 1-3-carboxamide B.7 N-tert- O

W-butyl-5 - [[4- 4% 1.85 397.1 B [5- 2.

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -4,5-dihydroisoxazo 1-3-carboxamide B.8 N- (2-furylmethyl) - So & 5 - [[4- [5- a (trifluoromethyl) -1,2,4- oxadiazole-3- 1,7 421,05 Byl] phenyl] methyl] -4,5-dihydroisoxazo 1-3- carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS B.9 morpholino-

F [5 - [[4- [5- / PF WN (trifluoromethyl) -1,2,4- oxadiazole-3-1 1.56 411.08 B il] phenyl] met O il] -4.5- di- 0 hydroisoxazo 1-3-yl] methanone B.10N- OPTA, cyclopentyl- “. 5 - [[4- [5- (trifluoromethyl) -1,2,4- 1,82 409,1 B oxadiazol-3-yl] phenyl] methyl] -4,5-dihydroisoxazo

Load Méto Ent Name of b & m rad Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS 1-3- carboxamide B.11N-methoxy-5- mm [14- [5- AE OD (trifluorome 2a tyl) -1,2,4-oxadiazol-3-yl] phenyl] met 1.46 371.03 ) Is useful] -4,5-dihydroisoxazo 1-3-carboxamide B.12N-ethoxy-5-o | [14- [5- RED (trifluorome pº useful) -1,2,4- 1,54 385,08 B oxadiazol-3-yl] phenyl] metyl] -4,5-di-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS hydroisoxazo 1-3- carboxamide B.13N- E

TA cyclobutyl- 'If FF f 5 - [[4- [5- (trifluoromethyl) -1,2,4- oxadiazole-3- 1,75 395,08 Byl] phenyl] methyl] -4,5- dihydroisoxazo 1-3-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS B.14N-benzyl-5- [[4- [5- O, (trifluorome HNN

Z til) -1,2,4- oxadiazol-3- 1,81 431,08 B il] phenyl] met i1) -4,5-di- DO “ps o hydroisoxazo 1-3-carboxamide B.15N-phenyl -5- O.

NH [[4- [5- As,: (trifluorome Ne

NO tilde) -1,2,4- oxadiazole-3- 1,86 417,06 B yl] phenyl] methyl] -4,5-dihydroisoxazo 1-3-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS carboxamide B.16N, N-diethyl ADO, (trifluorome SD useful) -1,2,4-oxadiazol-3- 1,76 397,1 Byl] phenyl] methyl] -4,5-di- hydroisoxazo 1-3- carboxamide B.17N-isobutyl-

W 5 - [[4- [5- RETO, (trifluorome a. Tyl) -1,2,4- 1,79 397,1 B oxadiazol-3-yl] phenyl] methyl] -4,5-di- hydroisoxazo

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS 1-3- carboxamide B.18N-allyl-5- o (14-05- AE (trifluorome useful salt) -1,2,4-oxadiazole-3- 1,64 381,06 Byl] phenyl] methyl ] -4,5-dihydroisoxazo 1-3-carboxamide B.19N-ethyl-5-

W [[4- [5- O TO (trifluorome is useful) -1,2,4- 1,59 369,06 B oxadiazol-3-yl] phenyl] methyl] -4,5-di-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS hydroisoxazo 1-3-carboxamide B.20N-methoxy-N-

AO methyl-5 - [[4- M From [5- aa (trifluorome til) -1,2,4- oxadiazole-3- 1,61 385,07 Byl] phenyl] methyl] -4,5-di - hydroisoxazo 1-3-carboxamide B.21N-isopropyl-goods. TO, (trifluorome Fº 1.7 383.07 B til) -1,2,4- oxadiazole-3-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS il] phenyl methyl] -4,5-dihydroisoxazo 1-3-carboxamide B.22N- (2,2- FIO,

Ç no À dimethylpropi AR & S 1) -5 - [[4- [5- q (trifluoromethyl) -1,2,4- oxadiazole-3- 1,89 411.11 B il] phenyl] methyl] -4 , 5-dihydroisoxazo 1-3-carboxamide B.23N-sec-butyl-FIO,

AX sas & 1.79 397.1. B (trifluorome q

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS tyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] -4,5-dihydroisoxazo 1-3-carboxamide B.244-hydroxy-2- FR [[4- [5- AA AA (trifluoromethyl) -1,2,4-oxadiazole-3- 1.04 402 A useful] phenyl] methyl] -5H-thiazole-ethyl 4-carboxylate

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS B.25N, N-dimethyl- nº 5 - [[4- [5- PA, $ e »ER (trifluoromethyl) -1,2,4- 101 oxadiazol-3- 1,57 369,06 B - il ] phenyl] met 104 yl] -4,5-dihydroisoxazo 1-3-carboxamide B.26N-methyl-5-O. [[4- [5- PA É No ma (useful trifluorome) -1,2 , 4- 155 oxadiazol-3- - yl] phenyl] met 159 yl] -4,5-dihydroisoxazo 1-3-

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS carboxamide B.27N-propyl-5- o.

VW [[4- [5- PA, FD Ar (trifluorome LL Not useful) -1,2,4- 124 oxadiazole-3- 1,69 383,07 B - yl] phenyl] met 128 il] -4,5 -di- hydroisoxazo 1-3- carboxamide B.28N- PQ,:: NF cyclopropyl- "q EE 5 - [[4- [5- 136 (trifluorome 1.61 381.06 B - tyl) -1.2, 4- 141 oxadiazol-3-yl] phenyl] methyl] -4,5-di-

Load Méto Ent tr da mp Name of rad (min) mass (ºC composed of a) [MH]:)

LCMS hydroisoxazo 1-3- carboxamide B.29acid 5 - [[4- F

F [5- A

RO (trifluorome N til) -1,2,4- 162 oxadiazol-3- - 47 "yl] phenyl] met 164 yl] -4,5-dihydroisoxazo 1-3-carboxylic B.303- [4- [ (5.5- No pre-dimethyl-4H- e - A oxazole -2- 1.73 326.2 A yl) methyl] phenyl] -5- (trifluorome

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS til) -1,2,4- oxadiazole Table C: Melting point data (mp) and / or LC / MS (retention time (tr)) for compounds of Formula (1):

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS C.1 N- Fr 160 and cyclopropyl- JO - O, NA 3 - [[4- [5- O 164 DD Ads (trifluorome useful) -1,2,4- oxadiazol-3-yl] phenyl] methyl ] limidazo [2,1-b] ltiazole-6-carboxamide

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS C.2 acid 3 - [[4- sr 0.93 395 A ne k [5- AS Og (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl] methyl] limidazo [2, 1-b] ltiazole-6-carboxylic

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS Cc.3 3 - [[4- [5- o £ 1.04 409 A

AA DAYS (methyl trifluorome) -1,2,4-oxadiazol-3-yl] phenyl] methyl] limidazo [2,1-b] methyl thiazole-6-carboxylate

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS C.4 3- [4- It is no; 1.05 352 A NATO WO: (imidazo [2,1 = F b] [1,3,4] thia diazol-6-ylmethyl) pheni 11-5- (trifluoromethyl) -1,2,4- oxadiazole C .5 3- [4 - [(2-; r 0.98 365 AU Dr methylimidazo ta: [2,1-blthiazol-6-yl) methyl] phenyl] -5- (trifluorome useful) -1,2, 4- oxadiazole

Load Méto Ent Name of b & m rad Structure (min) mass (ºC composed of a) [MH]:)

LCMS Cc.6 3- [4 - [(2- tu 1.09 366 A methylimidazo 2 [2,1- b1 [1,3,4] thia diazol-6-yl) methyl] phenyl] -5- ( trifluoromeyl) -1,2,4- oxadiazole C.7 3- [4 - [(3-: o 0.98 365 A methylimidazo Lat [2,1-blthiazol-6- yl) methyl] phenyl] -5 - (trifluorome tyl) -1,2,4- oxadiazole

Load Méto Ent tr da mp Rad name Structure (min) mass (ºC composed of a) | [MHH] * +)

LCMS Cc.8 3- [4-; no rf 0.95 351 A (imidazo [2.1 Que Tt -bltiazol-6-ylmethyl) pheni 11-5- (trifluorome tyl) -1,2,4- oxadiazole

BIOLOGICAL EXAMPLES

[00331] General examples of leaf disc tests in well plates:

[00332] 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 (curative) 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 level of disease is carried out 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.

[00333] General examples of liquid culture tests on well plates:

[00334] Fragments of Mycelia or suspensions of conidia of a fungus freshly prepared from liquid cultures of the fungus or from cryogenic storage are directly mixed in nutrient broth. DMSO solutions of the test compound (max. 10 mg / mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 µl of this solution are pipetted into a microtiter plate (96 well format). The nutrient broth containing the spores — fungal / mycelium fragments is then added to give 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)

[00335] 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 (rh) at 75% under a light regime of 12 hours of light / 12 hours of darkness in an air-conditioned chamber and the activity of a compound was evaluated as a percentage of control of the disease compared to no treatment when an appropriate level of damage from the disease appears in untreated leaf control segments (7 to 9 days after application).

[00336] The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[00337] (Compounds from Table A) A.2, A.3, A.7, A.10O, A.12, A.14, A.18, A.23, A.24, A.25, A .26, A.27, A.28, A.29, A.30, A.31, A.32, A.33, A.34, A.35, A.36, A.37, A.38 , A.39, A.40, A.41, A.42, A.43, A.44, A.45, A.46, A.47, A.48, A.S1, A.52, A .53, A.54, A.55, A.58, A.59, A.60

[00338] (Compounds from Table B) B.3, B.4, B.5, B.6, B.7, B.8, B.9, B.10, B.11, B.12, B .13, B.14, B.15, B.16, B.18, B.19, B.20, B.21, B.22, B.24, B.25, B.26, B.27 , B.28, B.29, B.30

[00339] (Compounds from Table C) C.1, C.2, C.3, C.4, C.5, C.6, C.7, C.8. Example 2: Fungicidal activity against Puccinia recondita f. sp. tritici / wheat / dressing on leaf discs (brown rust)

[00340] 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 an air-conditioned 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 damage caused by the disease appears in untreated leaf control segments (6 to 8 days after application).

[00341] The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[00342] (Compounds from Table A) A.2, A.3, A.10, A.13, A.14, A.17, A.18, A.19, A.23, A.24, A .25, A.29, A.34, A.35, A.36, A.38, A.39, A.42, A.43, A.44, A.45, A.46, A.48 , A.49, A.51, A.53, A.55, A.59, A.60.

[00343] (Compounds from Table B) B.3, B.4, B.5, B.9, B.19, B.25, B.26, B.30.

[00344] (Compounds from Table C) C.2, C.4, C.5, C.6, C.7, Cc.8.

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

[00345] Soybean leaf discs are placed on water-agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, 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 rh at 75%, the leaf discs are kept at 20 ºC with 12 h of light / day and rh at 75%. The activity of a compound is assessed as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears in untreated leaf control discs (12 to 14 days after application).

[00346] The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test compared to untreated leaf control discs under the same conditions, which show extensive disease development.

[00347] (Compounds from Table A) A.10, A.13, A.14, A.23, A.24, A.42, A.43, A.44, A.45, A.46, A .47, A.48, A.51, A.53, A.56, A.59, A.60.

[00348] (Compounds from Table B) B.3, B.4, B.25, B.26, B.27, B.28, B.30.

[00349] (Compounds from Table C) C.4, C.7, C.8.

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

[00350] 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.

[00351] The following compounds at 20 ppm in the applied formulation give at least 80% disease control in this test compared to the untreated control under the same conditions, which shows extensive disease development.

[00352] (Compounds from Table A) A.2, A.3, A.4, A.5, A.7, A.8, A.9, A.10, A.11, A.12, A .13, A.14, A.16, A.17, A.18, A.19, A.22, A.23, A.24, A.25, A.26, A.27, A.28 , A.29, A.30, A.31, A.33, A.34, A.35, A.36, A.38, A.39, A.40, A.41, A.42, A .43, A.44, A.45, A.46, A.47, A.48, A.49, A.50, A.51, A.52, A.53, A.54, A.55 , A.59, A.GO.

[00353] (Compounds from Table B) B.1, B.3, B.4, B.5, B.6, B.7, B.8, B.9, B.10, B.11, B .12, B.13, B.16, B.17, B.18, B.19, B.20, B.21, B.22, B.23, B.24, B.25, B.26 , B.27, B.28, B.29, B.30.

[00354] (Compounds from Table C) C.1, C.2, C.3, C.4, C.5, C.6, C.7, C.8.

Claims (15)

CLAIMS: 1. Compound of formula (1): Ro NO F Z. R RR RR (1) characterized by the fact that Ri, R2, R3, Rº are independently selected from hydrogen or fluorine and in which 0, 1 or 2 of R! , R2, Rà and Rº are fluorine; Rº and Rº are independently selected from hydrogen, C1.4 alkyl, C3.4 alkenyl or halogen; Z is selected from 721, 7º or 73; where Z! represents a heterocyclyl linked to C (R5) (R6s) through a CC bond, where the heterocyclyl fraction is a 5-membered non-aromatic ring that contains 1 nitrogen in the ring system and optionally comprises 1, 2 or 3 additional ring members independently selected from the group consisting of O, S, N, NR7, C (O0) or S (0)>, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; 7th? represents a heteroaryl linked to C (R5) (R6) through a CC bond, where the heteroaryl fraction is a 5-membered aromatic ring that contains 1 nitrogen atom in the ring system and optionally comprises 1, 2 or 3 ring members additional independently selected from the group consisting of O, S, N or NR; Rº is hydrogen, C1i4 alkyl, Cia alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, C14a alkylsulfonyl, C12 N-alkylaminosulfonyl or N, N-dialkyl1-alkyl .2; in that, for 2! and 7th, the heterocyclyl or heteroaryl fraction is: optionally substituted by 1, 2 or 3 substituents, which can be the same or different, selected from R8, or is replaced by 1 substituent selected from Rº and 1 substituent selected from phenyl or oxazolyl or is replaced by 1 substituent selected from phenyl or oxazolyl; Rê represents cyano, halogen, hydroxy, C1.4 alkyl, C2.4 alkenyl, C2.4 alkynyl, C1-4 cyanoalkyl, C1-1 haloalkyl, Cia haloalkenyl, Cia alkoxy, Cia haloalkoxy, C3-14 alkenyloxy, C3 alkynyloxy. 4, amino, C1.4 N-alkylamino, C1-4 N, N-dialkylamino, C1.4 alkylcarbonyl, C1-14 alkoxycarbonyl, C1-14 alkylcarbonylamino, C1-s, N-alkylaminocarbonyl C1-4, N, N-dialkylaminocarbonyl C1-4 , C1.4 alkoxycarbonylamino, C2-14-N-alkenyl C2-4, N-alkynyl C2-4-aminocarbonyl, N-furan-2-yl-methyl-aminocarbonyl, N-cycloalkylaminocarbonyl C3-6, N-alkoxy C1 - 2 C1alkylaminocarbonyl> 2, N-alkoxyminocarbonyl C1a1, phenylaminocarbonyl, phenylalkylaminocarbonyl Cia, N-C1-a-N-alkyl C1-a-aminocarbonyl, -C (0) OH, C1-4 alkoxycarbonylamino C1.2 and N-morpholinocarbonyl; Z3 represents a fused, partially saturated or unsaturated 7 to 9-membered heterobicyclic ring system comprising a fragment: (i) a 5-membered non-aromatic ring containing 1 ring nitrogen or (ii) a 5-membered aromatic ring containing 1 or 2 ring nitrogen, where fragments (1) and (ii) are linked to C (R5) (R6) via a CC bond, and where the heterobicycle comprises - optionally 1 to 4 additional groups selected from O, S, N or NRº, with the proviso that the heterobicycle cannot contain 2 contiguous atoms selected from 0 eS and in which Z? it is optionally substituted by 1, 2 or 3 substituents, which can be the same or different, selected from Ro; Rº is hydrogen, C1i4 alkyl, Cia alkoxy, formyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, N-alkylaminocarbonyl C1.4, N, N-dialkylaminocarbonyl C1i4, C14a alkylsulfonyl, C12 N-alkylaminosulfonyl or N, N-dialkyl1-alkyl .2; and R! º represents cyan, halogen, hydroxy, C1i4 alkyl, alkenyl C2.4, alkynyl C2-4, haloalkyl C1-4, haloalkenyl Cr-14, alkoxy Cia, haloalkoxy Cia, alkenyloxy C34, alkynyloxy C3.4, N-alkylamino C1.4, N, N-dialkylamino C1-4, C1-4alkylcarbonyl, C1-4alkoxycarbonylamino C1.4, N-alkylaminocarbonyl C141a, N, N-dialkylaminocarbonyl C1.4, alkoxycarbonylamino C1-4 ,, N-cyclopropylaminocarbonyl and -C (0) OH; or a salt or N-oxide thereof and provided that the compound of Formula (1) is not 3- [4 - [(5,5-dimethyl-4H-oxazol-2-yl) methyl] phenyl] -5 - (trifluoromethyl) -1,2,4-0xadiazole. 2. Compound according to claim 1, characterized by the fact that R! the Rº are hydrogen. 3. A compound according to any one of claims 1 and 2, characterized by the fact that Rº and Ré are hydrogen. Compound according to any one of claims 1, 2 and 3, characterized by the fact that Z is Z2 !. 5. Compound according to claim 4, characterized by the fact that 2! is selected from: optionally substituted by 1 or 2 substituents, which can be the same or different, selected from Rº. 6. Compound according to any one of the claims 4 and 5, characterized by the fact that Rê is independently selected from hydroxy, C1-6 alkyl, C1-14 cyanoalkyl, C1-4 haloalkyl, amino, N-C1-4 alkylamino, N, N-C1-4 alkylamino, C1-alkylcarbonyl. 4, C1 alkoxycarbonyl. 4a, N-alkylaminocarbonyl C1.4 or N, N-Nalkylaminocarbonyl C1-4. Compound according to any one of claims 1, 2 and 3, characterized by the fact that Z is 22. 8. Compound, according to claim 7, characterized by the fact that 7º is selected from: R O — N Ss N N e e e 4X and N N Ss o optionally substituted by 1 or 2 substituents, which can be the same or different, selected from Rº. Compound according to any one of claims 7 and 8, characterized by the fact that R8 is independently selected from hydroxy, C1-6 alkyl, C1-14 cyanoalkyl, C1-1- haloalkyl, amino, N-C1-4 alkylamino, N , N-dialkylamino C1.4, alkylcarbonyl C1.4, alkoxycarbonyl C1. 4a, N-alkylaminocarbonyl C1.4 or N, N-Nalkylaminocarbonyl C1-4. 10. Compound according to any one of claims 1, 2 and 3, characterized by the fact that 2 is 23. A compound according to claim 10, characterized by the fact that Z3 is: X and Ss Ss As (= (Os e) TA Ne optionally substituted with 1, 2 or 3 substituents, which can be the same or different, selected from RX, 12. Agrochemical composition characterized by the fact that it comprises a fungicidal effective amount of a compound of Formula (1), 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 of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized by the fact that a fungicidal effective amount of a compound of Formula (1), 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 (1), as defined in any one of claims 1, 2, 3, 4, 5, 6, 7, 8, 9, and 11, characterized in that it is as a fungicide.