Microbiocidal oxadiazole derivatives

Abstract

Compounds of the formula (I) ##STR00001## wherein the substituents are as defined in claim 1, useful as a pesticides, especially as fungicides.

Claims

1. A method of controlling or preventing infestation of plants by phytopathogenic microorganisms, comprising: applying to the plants, to parts thereof, or the locus thereof, a fungicidally effective amount of a compound of formula (I): ##STR00349## wherein n is 1 or 2; A.sup.1 represents N or CR.sup.1 wherein R.sup.1 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; A.sup.2 represents N or CR.sup.2, wherein R.sup.2 represents hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; A.sup.3 represents N or CR.sup.3, wherein R.sup.3 represents hydrogen or halogen; A.sup.4 represents N or CR.sup.4, wherein R.sup.4 represents hydrogen or halogen; and wherein 0 or 1 or 2 of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are N; R.sup.5 and R.sup.6 are independently selected from hydrogen, C.sub.1-4alkyl, halogen, cyano, trifluoromethyl and difluoromethyl, or R.sup.5 and R.sup.6 together with the carbon atom they share form a cyclopropyl; Z is selected from Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5 or Z.sup.6; wherein Z.sup.1 represents a heterocyclyl linked to C(R.sup.5)(R.sup.6) via a C—C bond, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which 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, NR.sup.7, C(O), or S(O).sub.2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; Z.sup.2 represents a heteroaryl linked to C(R.sup.5)(R.sup.6) via a C—C bond, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which contains 1 nitrogen atom in the ring system and optionally comprises 1, 2, or 3 additional ring members independently selected from the group consisting of O, S, N, or NR.sup.7; R.sup.7 is hydrogen, C.sub.1-4alkyl, C.sub.1-4alkoxy, formyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, N—C.sub.1-4alkylaminocarbonyl, N,N-diC.sub.1-4alkylaminocarbonyl, C.sub.1-4alkylsulfonyl, N—C.sub.1-2alkylaminosulfonyl, or N,N-diC.sub.1-2alkylaminosulfonyl; and wherein for Z.sup.1 and Z.sup.2, the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.8; R.sup.8 is cyano, halogen, hydroxy, C.sub.1-4alkyl, C.sub.2-4alkenyl, C.sub.2-4alkynyl, C.sub.1-4haloalkyl, C.sub.2-4haloalkenyl, C.sub.1-4alkoxy, C.sub.1-4haloalkoxy, C.sub.3-4alkenyloxy, C.sub.3-4alkynyloxy, N—C.sub.1-4alkylamino, N,N-diC.sub.1-4alkylamino, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, C.sub.1-4alkylcarbonylamino, N—C.sub.1-4alkylaminocarbonyl, N,N-diC.sub.1-4alkylaminocarbonyl or C.sub.1-4alkoxycarbonylamino; Z.sup.3 represents a heterocyclyl linked to C(R.sup.5)(R.sup.6) via a C—N bond, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which 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, NR.sup.9 or C(═N—O—C.sub.1-4alkyl), with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; Z.sup.4 represents a heteroaryl linked to C(R.sup.5)(R.sup.6) via a C—N bond, wherein the heteroaryl moiety is a 5-membered aromatic ring which contains 1 to 4 nitrogen atoms in the ring system; R.sup.9 is hydrogen, C.sub.1-4alkyl, C.sub.1-4alkoxy, formyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, N—C.sub.1-4alkylaminocarbonyl, or N,N-diC.sub.1-4alkylaminocarbonyl; and wherein for Z.sup.3 and Z.sup.4, the heterocyclyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.10; wherein R.sup.10 represents: (i) cyano, halogen, hydroxy, amino, C.sub.1-4alkyl, C.sub.2-4alkenyl, C.sub.2-4alkynyl, C.sub.1-4haloalkyl, C.sub.2-4haloalkenyl, C.sub.1-4alkoxy, C.sub.1-4alkoxyC.sub.1-4alkyl, C.sub.1-4haloalkoxy, C.sub.1-4alkylsulfanyl, C.sub.1-4alkylsulfinyl, C.sub.1-4alkylsulfonyl, C.sub.1-4haloalkylsulfanyl, C.sub.3-4alkenyloxy, C.sub.3-4alkynyloxy, N—C.sub.1-4alkylamino, N,N-diC.sub.1-4alkylamino, formyl, hydroxycarbonyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, C.sub.1-4alkylcarbonylamino, aminocarbonyl, N—C.sub.1-4alkylaminocarbonyl, N—C.sub.2-4alkenylaminocarbonyl, N—C.sub.2-4alkynylaminocarbonyl, N,N-diC.sub.1-4alkylaminocarbonyl, N-morpholinoaminocarbonyl, N—C.sub.1-4alkoxyaminocarbonyl, N—C.sub.1-4alkyl-N—C.sub.1-4alkoxyaminocarbonyl, C.sub.1-4alkoxycarbonylamino, C.sub.1-4alkoxycarbonylaminoC.sub.1-4alkyl, N—C.sub.1-4alkoxyC.sub.1-4alkylaminocarbonyl, phenylcarbonyloxyC.sub.1-4alkyl, phenylcarbonylaminoC.sub.1-4alkyl, C.sub.1-4alkylcarbonyloxy, C.sub.1-4haloalkylcarbonyloxy, C.sub.1-4alkylcarbonyloxyC.sub.1-4alkyl, C.sub.1-4alkylcarbonylaminoC.sub.1-4alkyl, or (C.sub.1-4alkyl).sub.3Si—; or (ii) —C(O)N(R.sup.a)(R.sup.b), wherein: R.sup.a is hydrogen, C.sub.1-4alkyl, C.sub.1-4haloalkyl, C.sub.1-4cyanoalkyl, hydroxyC.sub.1-4alkyl, C.sub.1-2alkoxyC.sub.1-4alkyl, C.sub.1-2haloalkoxyC.sub.1-4alkyl, C.sub.3-5alkenyl, C.sub.3-5alkynyl, aminoC.sub.1-4alkyl, N—C.sub.1-4alkylaminoC.sub.1-4alkyl, N,N-diC.sub.1-4alkylaminoC.sub.1-4alkyl, formyl, C.sub.1-4alkylcarbonyl, C.sub.3-4cycloalkylcarbonyl, C.sub.1-4haloalkylcarbonyl, C.sub.1-4alkylcarbonylC.sub.1-4alkyl, C.sub.1-4alkoxycarbonylC.sub.1-4alkyl, C.sub.1-4alkylcarbonyloxyC.sub.1-4alkyl, N—C.sub.1-4alkylaminocarbonylC.sub.1-4alkyl, N,N-diC.sub.1-4alkylaminocarbonylC.sub.1-4alkyl, C.sub.1-4alkylsulfanylC.sub.1-4alkyl, C.sub.1-4alkylsulfonyl, C.sub.1-4alkylsulfonylC.sub.1-4alkyl, C.sub.1-4alkylsulfonylaminoC.sub.1-4alkyl, C.sub.1-4alkoxycarbonylaminoC.sub.1-4alkyl, C.sub.1-4alkylcarbonylaminoC.sub.1-4alkyl, C.sub.1-4alkoxycarbonylaminoC.sub.1-4alkyl, or C.sub.1-4haloalkylcarbonylaminoC.sub.1-4alkyl, and R.sup.b is hydrogen, hydroxyl, C.sub.1-4alkyl, C.sub.1-4haloalkyl, C.sub.1-4cyanoalkyl, hydroxyC.sub.1-4alkyl, C.sub.1-2alkoxyC.sub.1-4alkyl, C.sub.3-4alkenyl, C.sub.3-4alkynyl, C.sub.3-4cycloalkyl, C.sub.3-4cycloalkylC.sub.1-2alkyl, C.sub.1-4alkoxy, C.sub.3-4alkenyloxy, C.sub.3-4haloalkenyloxy, or C.sub.3-4alkynyloxy; or R.sup.a and R.sup.b together with the nitrogen atom to which they are bonded, form a 4-, 5- or 6-membered cycle optionally containing an additional heteroatom or group selected from O, S, S(O).sub.2, C(O) and NR.sup.c, wherein R.sup.c is hydrogen, methyl, methoxy, formyl or acyl; or (iii) —C(O)O—R.sup.d, wherein: R.sup.d is hydrogen, C.sub.1-4alkyl, C.sub.1-4haloalkyl, C.sub.1-4cyanoalkyl, hydroxyC.sub.1-4alkyl, C.sub.1-2alkoxyC.sub.1-4alkyl, C.sub.1-2alkoxyC.sub.1-2alkoxyC.sub.1-4alkyl, C.sub.1-2haloalkoxyC.sub.1-4alkyl, C.sub.3-5alkenyl, C.sub.3-4haloalkenyl, C.sub.3-4alkenyloxyC.sub.1-4alkyl, C.sub.3-5alkynyl, C.sub.3-4alkynyloxyC.sub.1-4alkyl, N—C.sub.1-3alkylaminoC.sub.1-4alkyl, N,N-di-C.sub.1-3alkylaminoC.sub.1-4alkyl, C.sub.1-4alkoxycarbonylaminoC.sub.1-4alkyl or C.sub.1-4alkylcarbonylaminoC.sub.1-4alkyl; or wherein for Z.sup.4, the heteroaryl moiety is optionally substituted by 1 substituent selected from R.sup.11 and further optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R.sup.10; wherein R.sup.11 represents: (i) C.sub.3-8cycloalkyl, C.sub.3-8cycloalkylC.sub.1-2alkyl, N—C.sub.3-8cycloalkylaminocarbonyl, N—C.sub.3-8cycloalkylC.sub.1-2alkylaminocarbonyl, phenyl, phenylC.sub.1-2alkyl, phenoxyC.sub.1-2alkyl, phenylC.sub.1-2alkylsulfanyl, heteroaryl, heteroarylC.sub.1-2alkyl, heteroaryloxyC.sub.1-2alkyl, N-heteroarylaminocarbonyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC.sub.1-6alkyl, heterocyclylcarbonyl wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, benzodioxolyl, and wherein any of said cycloalkyl, phenyl, heteroaryl, heterocyclyl and benzodioxolyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.12; or (ii) —C(O)N(R.sup.e)(R.sup.f), wherein: R.sup.e is C.sub.3-5cycloalkyl, C.sub.3-5cycloalkylC.sub.1-2alkyl, phenyl, phenylC.sub.1-2alkyl, heterocyclyl, heterocyclylC.sub.1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O).sub.2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC.sub.1-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 groups which are oxo (═O), and R.sup.f is hydrogen, C.sub.1-4alkyl, C.sub.1-4alkoxy C.sub.1-4haloalkyl, C.sub.3-4alkenyl, C.sub.3-4alkynyl, C.sub.3-4cycloalkyl, or C.sub.3-4cycloalkylC.sub.1-2alkyl; or (iii) —C(O)O—R.sup.g, wherein: R.sup.g is C.sub.3-5cycloalkyl, C.sub.3-5cycloalkylC.sub.1-2alkyl, phenyl, phenylC.sub.1-2alkyl, heterocyclyl, heterocyclylC.sub.1-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O).sub.2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC.sub.1-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the cycloalkyl or heterocyclyl moiety is optionally substituted by 1 or 2 groups which are oxo (═O); or (iv) (C.sub.1-4alkyl)-O—N═C(R.sup.h)—, (C.sub.1-4haloalkyl)-O—N═C(R.sup.h)—, (C.sub.2-4alkenyl)-O—N═C(R.sup.h), (C.sub.2-4alkynyl)-O—N═C(R.sup.h)—, benzyl-O—N═C(R.sup.h)—, wherein R.sup.h is hydrogen or methyl; R.sup.12 is cyano, fluoro, chloro, bromo, methyl, ethyl, formyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy or ethoxycarbonyl; Z.sup.5 represents a heterobicyclyl linked to C(R.sup.5)(R.sup.6) via a C—N bond, wherein the heterobicyclyl moiety is a 7- to 10-membered saturated, partially saturated or partially aromatic fused ring system which 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, NR.sup.13, C(O) or S(O).sub.2, with the proviso that the heterobicyclyl cannot contain 2 contiguous atoms selected from O and S; Z.sup.6 represents a heterodiaryl linked to C(R.sup.5)(R.sup.6) via a C—N bond, wherein the heterdioaryl moiety is a 9-membered di-aromatic system which contains 1 to 4 nitrogen atoms in the ring system; R.sup.13 is hydrogen, C.sub.1-4alkyl, C.sub.1-4alkoxy, formyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, N—C.sub.1-4alkylaminocarbonyl, or N,N-diC.sub.1-4alkylaminocarbonyl; and wherein for Z.sup.5 and Z.sup.6, the heterobicyclyl or heterodiaryl moiety is optionally substituted by 1, 2, 3 or 4 substituents, which may be the same or different, selected from R.sup.14; R.sup.14 is cyano, halogen, hydroxy, formyl, C.sub.1-4alkyl, C.sub.2-4alkenyl, C.sub.2-4alkynyl, C.sub.1-4haloalkyl, cyanoC.sub.1-4alkyl, C.sub.2-4haloalkenyl, C.sub.1-4alkoxy, C.sub.1-4haloalkoxy, C.sub.3-4alkenyloxy, C.sub.3-4alkynyloxy, N—C.sub.1-4alkylamino, N,N-diC.sub.1-4alkylamino, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, C.sub.1-4alkylcarbonylamino, N—C.sub.1-4alkylaminocarbonyl, N,N-diC.sub.1-4alkylaminocarbonyl or C.sub.1-4alkoxycarbonylamino, and additionally oxo (═O) for Z.sup.5; or wherein for Z.sup.5 and Z.sup.6, the heterobicyclyl or heterodiaryl moiety is optionally substituted by 1 substituent selected from R.sup.15 and further optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R.sup.14; R.sup.15 is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, wherein phenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and ethoxy; or a salt or an N-oxide thereof.

2. The method according to claim 1, wherein A.sup.1 is N or CR.sup.1 wherein R.sup.1 is hydrogen, chloro, fluoro, methyl, methoxy or trifluoromethyl, and A.sup.2, A.sup.3 and A.sup.4 are C—H.

3. The method according to claim 1, wherein A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are C—H.

4. The method according to claim 1, wherein A.sup.3 is CR.sup.3 and R.sup.3 is halogen, and A.sup.1, A.sup.2 and A.sup.4 are C—H.

5. The method according to claim 1, wherein R.sup.5 and R.sup.6 are hydrogen, or R.sup.5 is hydrogen and R.sup.6 is methyl.

6. The method according to claim 1, wherein Z is Z.sup.4.

7. The method according to claim 6, wherein the heteroaryl moiety of Z.sup.4 is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.10; R.sup.10 is cyano, halogen, hydroxy, amino, C.sub.1-4alkyl, C.sub.1-4haloalkyl, C.sub.1-4alkoxy, C.sub.1-4alkoxyC.sub.1-4alkyl, C.sub.1-4alkylsulfanyl, C.sub.1-4haloalkylsulfanyl, N,N-diC.sub.1-4alkylamino, formyl, hydroxy carbonyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, C.sub.3-4alkenyloxycarbonyl, C.sub.3-4alkynyloxycarbonyl, aminocarbonyl, N—C.sub.1-4alkylaminocarbonyl, N—C.sub.3-4alkenylaminocarbonyl, N—C.sub.2-4alkynylaminocarbonyl, N,N-diC.sub.1-4alkylaminocarbonyl, N-morpholinoaminocarbonyl, N—C.sub.1-4alkoxyaminocarbonyl, N—C.sub.1-4alkyl-N—C.sub.1-4alkoxyaminocarbonyl, N—C.sub.1-4alkoxyC.sub.1-4alkylaminocarbonyl, phenylcarbonylaminoC.sub.1-4alkyl, C.sub.1-4alkylcarbonyloxyC.sub.1-4alkyl, C.sub.1-4alkylcarbonylaminoC.sub.1-4alkyl, C.sub.1-4alkoxycarbonylaminoC.sub.1-4alkyl, or (C.sub.1-4alky).sub.3Si—; or Z.sup.4 is optionally substituted by 1 substituent selected from R.sup.11 and further optionally substituted by 1 or 2 substituents selected from R.sup.10; wherein R.sup.11 is C.sub.3-6cycloalkyl, C.sub.3-6cycloalkylC.sub.1-2alkyl, N—C.sub.3-6cycloalkylaminocarbonyl, N—C.sub.3-6cycloalkylC.sub.1-2alkylaminocarbonyl, C.sub.3-4cycloalkoxycarbonyl, C.sub.3-4cycloalkylC.sub.1-2alkoxycarbonyl, phenyl, phenylC.sub.1-2alkyl, phenoxyC.sub.1-2alkyl, phenylC.sub.1-2alkylsulfanyl, N-phenylaminocarbonyl, heterocyclyl, heterocyclylcarbonyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1, 2, or 3 ring members independently selected from the group consisting of O, S, N or S(O).sub.2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, heteroarylC.sub.1-2alkyl, heteroaryloxyC.sub.1-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, benzodioxolyl, and wherein any of said cycloalkyl, phenyl, heterocyclyl, heteroaryl and benzodioxolyl moieties are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.12; and R.sup.12 is fluoro, chloro, bromo, methyl, ethyl, or methoxy.

8. The method according to claim 6, wherein Z.sup.4 is pyrazolyl, imidazolyl or triazolyl, wherein pyrazolyl, imidazolyl or triazolyl are optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R.sup.10; or pyrazolyl, imidazolyl or triazolyl are optionally substituted by 1 substituent selected from R.sup.11 and are further optionally substituted by 1 substituent selected from R.sup.10.

9. The method according to claim 8, wherein Z.sup.4 is pyrazol-1-yl, 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl, wherein pyrazol-1-yl is optionally substituted by 1 substituent selected from R.sup.10 or R.sup.11, wherein R.sup.10 is hydroxy carbonyl, methoxycarbonyl, ethoxy carbonyl, n-propoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, methoxyethylaminocarbonyl, propargylaminocarbonyl, N-morpholinoaminocarbonyl, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N-methyl-N-methoxyaminocarbonyl or N-methoxyaminocarbonyl, and R.sup.11 is cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl or cyclohexylaminocarbonyl; and 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl is optionally substituted by 1 substituent selected from R.sup.10 or R.sup.11, wherein R.sup.10 is cyano, ethynyl, fluoro, chloro, methyl, ethyl, trifluoromethyl, methoxy, ethoxycarbonyl or ethoxymethyl, and R.sup.11 is cyclopropyl.

10. The method according to claim 1, wherein Z is Z.sup.6 selected from indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl.

11. The method according to claim 10, wherein: indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl is optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R.sup.14, wherein R.sup.14 is cyano, halogen, hydroxy, formyl, C.sub.1-4alkyl, C.sub.1-4haloalkyl, C.sub.1-4alkoxy, C.sub.1-4alkylcarbonyl, or C.sub.1-4alkoxycarbonyl; or indolyl, indazolyl, benzimidazolyl, pyrrolopyridinyl or triazolopyridinyl is optionally substituted by 1 substituent selected from R.sup.15 and further optionally substituted by 1 or 2 substituents selected from R.sup.14, wherein R.sup.15 is pyridinyl, benzodioxolyloxy, phenoxy or phenylsulfanyl, wherein phenoxy and phenylsulfanyl are optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from chloro, fluoro, bromo, methyl, ethyl, methoxy and ethoxy.

12. The method according to claim 1, wherein the compound of formula (I) is part of an agrochemical composition.

13. The method according to claim 12, wherein the agrochemical composition further comprises at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

14. The method according to claim 1, wherein applying is to the plant.

15. The method according to claim 1, wherein applying is to the locus thereof.

Description

EXAMPLES

(1) The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

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

(3) Throughout this description, temperatures are given in degrees Celsius (° C.) and “mp.” means melting point. LC/MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method (Methods A, B and C) is as follows:

(4) The Description of the LC/MS Apparatus and the Method A is:

(5) SQ Detector 2 from Waters

(6) Ionisation method: Electrospray

(7) Polarity: positive and negative ions

(8) Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650

(9) Mass range: 100 to 900 Da

(10) DAD Wavelength range (nm): 210 to 500

(11) Method Waters ACQUITY UPLC with the following HPLC gradient conditions:

(12) (Solvent A: Water/Methanol 20:1+0.05% formic acid and Solvent B: Acetonitrile+0.05% formic acid)

(13) TABLE-US-00002 Time Flow rate (minutes) A (%) B (%) (ml/min) 0 100 0 0.85 1.2 0 100 0.85 1.5 0 100 0.85
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60° C.
The Description of the LC/MS Apparatus and the Method B is:
SQ Detector 2 from Waters
Ionisation method: Electrospray
Polarity: positive ions
Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700
Mass range: 140 to 800 Da
DAD Wavelength range (nm): 210 to 400
Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water/Methanol 9:1+0.1% formic acid and Solvent B: Acetonitrile+0.1% formic acid)

(14) TABLE-US-00003 Time Flow rate (minutes) A (%) B (%) (ml/min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60° C.
The Description of the LC/MS Apparatus and the Method C is:
SQ Detector 2 from Waters
Ionisation method: Electrospray
ACQUITY H Class UPLC, Mass Spectrometer from Waters
Polarity: positive and Negative Polarity Switch
Scan Type MS1 Scan
Capillary (kV) 3.00, Cone (V) 40.00, Desolvation Temperature (° C.) 500, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 1000
Mass range: 0 to 2000 Da
DAD Wavelength range (nm): 200 to 350
Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water+, 0.1% formic acid and Solvent B: Acetonitrile)

(15) TABLE-US-00004 Time Flow rate (minutes) A (%) B (%) (ml/min) 0 70 30 0.5 0.05 70 30 0.5 0.8 5 95 0.5 1.8 5 95 0.5 2.45 70 30 0.5 2.50 70 30 0.5
Type of column: Waters ACQUITY UPLC BEH C.sub.18; Column length: 50 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.7 micron; Temperature: 35° C.

(16) Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.

Formulation Examples

(17) TABLE-US-00005 Wettable powders a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% sodium lignosulfonate  5%  5% — sodium lauryl sulfate  3% —  5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid  5% 10% 10% Kaolin 62% 27% —

(18) The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

(19) TABLE-US-00006 Powders for dry seed treatment a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — 20%

(20) The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

(21) Emulsifiable Concentrate

(22) TABLE-US-00007 active ingredient [compound of formula (I)] 10% octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether  4% (35 mol of ethylene oxide) Cyclohexanone 30% xylene mixture 50%

(23) Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

(24) TABLE-US-00008 Dusts a) b) c) Active ingredient  5%  6%  4% [compound of formula (I)] Talcum 95% — — Kaolin — 94% — mineral filler — — 96%

(25) Ready-for-use dusts are 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 dressings for seed.

(26) Extruder Granules

(27) TABLE-US-00009 Active ingredient 15% [compound of formula (I)] sodium lignosulfonate  2% Carboxymethylcellulose  1% Kaolin 82%

(28) The active ingredient is mixed and ground with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

(29) Coated Granules

(30) TABLE-US-00010 Active ingredient [compound of formula (I)]  8% polyethylene glycol (mol. wt. 200)  3% Kaolin 89%

(31) The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

(32) Suspension Concentrate

(33) TABLE-US-00011 active ingredient [compound of formula (I)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

(34) The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

(35) Flowable Concentrate for Seed Treatment

(36) TABLE-US-00012 active ingredient [compound of formula (I)]   40% propylene glycol   5% copolymer butanol PO/EO   2% tristyrenephenole with 10-20 moles EO   2% 1,2-benzisothiazolin-3-one  0.5% (in the form of a 20% solution in water) monoazo-pigment calcium salt   5% Silicone oil  0.2% (in the form of a 75% emulsion in water) Water 45.3%

(37) The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

(38) Slow-Release Capsule Suspension

(39) 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 polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.

(40) The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns.

(41) The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

List of Abbreviations

(42) AIBN=azobisisobutyronitrile DMF=dimethylformamide DIPEA=N,N-di-isopropylethylamine EtOAc=ethyl acetate HCl=hydrochloric acid mp=melting point ° C.=degrees Celsius MeOH=methyl alcohol NaOH=sodium hydroxide NBS=N-bromosuccinimide min=minutes RT=room temperature h=hour(s) TFAA=trifluoroacetic acid anhydride THF=tetrahydrofuran t.sub.R=retention time (in minutes) LC/MS=Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)

Example 1: This Example Illustrates the Preparation 3-[4-(imidazol-1-ylmethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound 1.18 of Table T1)

(43) ##STR00018##

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

(44) ##STR00019##

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

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

(46) ##STR00020##

(47) To a stirred solution of N′-hydroxy-4-methyl-benzamidine (38.7 g, 0.25 mol) in 2-methyltetrahydrofuran (750 mL) was added TFAA at 0° C. The reaction mixture was stirred at 15° C. for two hours and then diluted with water. The organic layer was separated, washed successively with sodium bicarbonate solution, ammonium chloride solution, water, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was subjected to flash chromatography over silica gel (750 g pre-packed column) with heptane/EtOAc 99:1 to 90:10 to afford the title compound as a clear oil, which solidified after storage.

(48) LC/MS (Method A) retention time=1.15 minutes, mass not detected.

(49) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

(50) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.41 (s).

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

(51) ##STR00021##

(52) A stirred mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in tetrachloromethane (480 mL) under argon was heated to 70° C. AIBN (4.03 g, 24 mmol) was added and the reaction mixture stirred at 65° C. for 18 hours. The mixture was cooled to RT and diluted with dichloromethane and water and the layers were separated. The organic layer was washed with sodium bicarbonate solution, dried over sodium sulfate, filtered and evaporated to dryness.

(53) The crude residue was subjected to flash chromatography over silica gel (750 g pre-packed column) with cyclohexane/EtOAc 100:0 to 95:5 to afford the title compound as a white solid mp: 58-63° C.

(54) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

(55) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.32 (s).

(56) 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole was isolated as by-product as a white solid mp: 61-66° C.

(57) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

(58) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.34 (s).

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

(59) ##STR00022##

(60) To a stirred 1:9 ratio mixture of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole and 3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (10.2 g) in acetonitrile (95 mL), water (1.9 mL) and DIPEA (6.20 ml, 35.7 mmol) was added diethylphosphite (4.7 mL, 35.7 mmol) at 5° C. The mixture was stirred at 5-10° C. for two hours, water and 1M HCl was added and acetonitrile evaporated under reduced pressure. The white slurry was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, and filtered. The solvent was removed under reduced pressure and the resultant crude residue subjected to flash chromatography over silica gel (40 g pre-packed column) with cyclohexane/EtOAc 99:1 to 9:1 to afford 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

(61) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

(62) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.32 (s).

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

(63) A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (100 mg, 0.31 mmol), imidazole (1.5 equiv., 0.46 mmol), and potassium carbonate (2 equiv., 0.62 mmol) in acetonitrile (3.0 mL) was heated in a microwave oven for 30 minutes at 120° C. Solids were removed by filtration and washed with ethyl acetate and the mother liquors evaporated to give a crude residue. Further solvent was removed under reduced pressure and the resultant residue purified by flash chromatography over silica gel (cyclohexane:EtOAc eluent gradient 1:0 to 0:1) to afford 3-[4-(imidazol-1-ylmethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole as a yellow solid. LC/MS (Method A) retention time=0.69 minutes, 295 (M+H). mp: 45-55° C.

(64) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.22 (d, 2H), 7.61 (d, 2H), 7.28 (d, 2H), 7.14 (s, 1H), 5.20 (s, 2H).

(65) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.39 (s).

Example 2: This Example Illustrates the Preparation 3-[4-[(4-cyclopentyltriazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound 1.24 of Table T1)

(66) ##STR00023##

(67) A solution of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (153 mg, 0.49 mmol) was dissolved in dimethylformamide (1.5 mL), isopropanol (1 mL) and water (1 mL). To the resultant white suspension was introduced sodium azide (64 mg), copper (II) sulfate (28 mg), and copper cyanide (18 mg). To the fine beige suspension was introduced ethynyl cyclopentane (0.06 mL) and triethylamine (1 mL) and the light green, cloudy solution was stirred over night at RT. The mixture was poured into a separatory funnel containing water and EtOAc, the layers were separated, and the aqueous fraction was then extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated under reduced pressure to afford the crude as a green oil. The crude was subject to combiflash chromatography over silicagel (heptane:EtOAc eluent gradient 99:1 to 1:1) to afford 3-[4-[(4-cyclopentyltriazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole as a white solid. LC/MS (Method A) retention time=1.10 minutes, 364 (M+H). mp: 117-119° C.

(68) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.12 (d, 2H), 7.39 (d, 2H), 7.22 (s, 1H), 5.57 (s, 1H), 3.18 (m, 1H), 2.09 (m, 2H), 1.75 (m, 2H), 1.70 (m, 4H).

(69) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.39 (s).

Example 3: This Example Illustrates the Preparation of 3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound 1.42 of Table T1 below)

(70) ##STR00024##

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

(71) ##STR00025##

(72) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid (4.00 g, 15.0 mmol) was suspended in dichloromethane (90 mL) DMF (0.01 mL, 0.150 mmol) was added followed by oxalyl chloride (1.46 mL, 16.5 mmol). The mixture was heated at reflux for 2 hours. The mixture was evaporated under reduced pressure to afford 4.15 g of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride as a yellow solid.

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

(73) ##STR00026##

(74) A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride from Step 1 (4.15 g, 14.6 mmol) in dichloromethane (20 mL) was added drop wise at room temperature to a stirred solution of N-methoxymethanamine (1.10 g, 17.5 mmol) and triethylamine (3.10 ml, 21.8 mmol) in dichloromethane (80 mL). The mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into water extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, and filtered. The solvent was removed under reduced pressure and the resultant crude residue was subjected to flash chromatography over silica gel (heptane:EtOAc eluent gradient 9:1 to 65:35) to afford 4.12 g of N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide as a solid. LC/MS (Method A) retention time=0.97 minutes, 302 (M+H).

(75) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.18 (d, 2H), 7.84 (d, 2H), 3.56 (s, 3H), 3.40 (s, 3H).

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

(76) ##STR00027##

(77) In a 75-mL multi neck flask equipped with stirrer, thermometer at −78° C. under argon, DIBAL-H, 1.0M in toluene (16 mL, 16.0 mmol) was added drop-wise to a solution of N-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (4.10 g, 13.3 mmol) in 2-methyltetrahydrofuran (90 mL). The mixture was stirred two hours at −78° C. and for one hour temperature was let increase to 0° C. Complete conversion observed by LC-MS. The mixture was quenched by drop wise addition of sat. ammonium chloride solution. Precipitation of a white solid occurred. 4 M HCl was added until full solubilisation. The mixture was extracted thrice with ethyl acetate. Combined organics were dried over magnesium sulfate and evaporated to afford the crude as beige solid. The crude was subject to combiflash chromatography over silica gel (heptane:EtOAc eluent gradient 99:1 to 90:10) to afford 2.93 g of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde as a white solid, mp: 40-50° C.

(78) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 10.12 (s, 1H), 8.31 (d, 2H), 8.05 (d, 2H).

(79) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.29 (s).

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

(80) ##STR00028##

(81) In a 50 mL flask dried and under argon, 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (1.36 mol) was dissolved in THF (10 mL) and cooled to −78° C. via a dry ice acetone bath. To this solution was introduced dropwise methyl magnesium bromide (0.70 mL, 2.03M in diethyl ether). The mixture was stirred for 1 h at −78° C. and then was quenched with a saturated aqueous ammonium chloride solution. The dry ice bath was removed, and the reaction was stirred at rt 5 min. it was then extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated under reduced pressure to afford the crude as a colourless oil. The crude was subject to combiflash chromatography over silicagel (heptane:EtOAc eluent gradient 99:1 to 1:1) to afford 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol as a white solid.

(82) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.12 (d, 2H), 7.54 (d, 2H), 5.00 (s, 1H), 1.54 (d, 3H).

(83) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.31 (s).

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

(84) ##STR00029##

(85) In a 50 mL flask dried and under argon, 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (1.36 mol) was dissolved in dichloromethane (10 mL). To this solution was introduced manganese oxide (40.6 mmol) and the heterogenous mixture was stirred for overnight at RT. The reaction solution was then filtered over a pad of celite and after washings with dichloromethane the combined organics were concentrated under reduced pressure to afford crude 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone as a white solid which was used directly without further purification.

(86) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.24 (d, 2H), 8.12 (d, 2H), 2.67 (s, 1H), 1.56 (d, 3H).

(87) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.39 (s).

Step 6: Preparation of 4-methyl-N-[(D)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamide

(88) ##STR00030##

(89) In a 50 mL flask dried and under argon, 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone (1.05 mol) was dissolved in methanol (10 mL). To this solution was introduced 4-methylbenzenesulfonohydrazide (1.16 mmol) and the resultant white suspension was stirred for overnight at RT. The reaction solution was then concentrated under reduced pressure to afford crude 4-methyl-N-[(E)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamide as a white solid which was used directly without further purification.

(90) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.12 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H), 7.60 (s.sub.br, 1H), 7.36 (d, 2H), 2.44 (s, 3H), 2.17 (s, 3H).

(91) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.34 (s).

Step 7: Preparation of 3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

(92) In a 10 mL flask dried and under argon, 4-methyl-N-[(E)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethylideneamino]benzenesulfonamide (0.47 mol) was dissolved in dioxane (1.4 mL). To this solution was introduced 2-methoxypyridine boronic acid (0.71 mmol) and the resultant beige suspension was stirred for 3 h at 110° C. After cooling to RT, the reaction solution was then concentrated under reduced pressure and the crude was subject to combiflash chromatography over silicagel (cyclohexane:EtOAc eluent gradient 99:1 to 4:1) to afford 3-[4-[1-(6-methoxy-3-pyridyl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole as a yellow oil.

(93) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.07 (d, 1H), 8.03 (d, 2H), 7.38 (d, 1H), 7.36 (d, 2H), 6.69 (d, 1H), 4.18 (q, 1H), 3.92 (s, 3H), 1.67 (d, 3H).

(94) .sup.19F NMR (400 MHz, CDCl.sub.3) δ ppm: −65.38 (s).

Example 4: This Example Illustrates the Preparation of 3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound 1.303 of Table T1 below)

(95) ##STR00031##

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

(96) ##STR00032##

(97) To a solution of 1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (1.15 g, 4.45 mmol) in dichloromethane (15 ml.) cooled to 0° C. using an ice bath was added tribromophosphane (0.465 ml, 4.90 mmol) over 30 minutes and the reaction mixture was stirred for 1.5 hrs. Then, an ice bath was used to cool the contents and a 10% sodium metabisulphite (50 ml) was introduced. After 15 minutes, the aqueous layer was extracted with dichloromethane and the total combined organic layer was washed with water and dried over Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resultant crude residue was purified by combiflash chromatography over silica gel using cyclohexane as eluent to afford pure 3-[4-(1-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1 g, 71% yield) as white solid.

(98) .sup.1H NMR (400 MHz, DMSO-d6) δ ppm: 8.07 (m, 2H), 7.75 (m, 2H), 5.76 (s, 1H), 5.59 (q, 1H), 2.02 (d, 3H).

Step 2: Preparation of 3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

(99) 3-[4-(1-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (150 mg, 0.47 mmol), 3,5-dimethylpyrazole (0.07 g, 0.70 mmol) and potassium carbonate (0.130 g, 0.93 mmol) were dissolved in acetonitrile (5 ml.) in a microwave vial. The mixture was then heated in the microwave at 100° C. for 30 minutes. The reaction mixture was diluted with water (20 ml.) and extracted with ethyl acetate. The total combined organic layer was washed with brine solution, dried over anhydrous Na.sub.2SO.sub.4, filtered, and concentrated at reduced pressure. The resultant crude residue was purified by combiflash chromatography over silica gel (cyclohexane:EtOAc eluent gradient 92:8) to afford pure 3-[4-[1-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (55 mg, 35%) as a light yellow gummy mass. LC/MS (Method C) retention time=1.61 minutes, 337 (M+H).

(100) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.04 (d, 2H), 7.25 (m, 2H), 5.87 (s, 1H), 5.41 (q, 1H), 2.30 (s, 3H), 2.12 (s, 3H), 1.95 (d, 3H).

Example 5: This Example Illustrates the Preparation of 3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound 1.309 of Table T1 Below)

(101) ##STR00033##

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

(102) ##STR00034##

(103) To a solution of 4-(2-bromoethyl)benzonitrile (2.0 g, 9.5 mmol) in ethanol (32 mL) was added hydroxylamine hydrochloride (2 equiv., 19 mmol) followed by triethylamine (4.5 equiv., 43 mmol). The reaction contents were allowed to stir at ambient temperature for 12 hrs and the volatiles were then removed at reduced pressure. The resultant crude mass was dissolved in tetrahydrofuran (60 mL), cooled to 0° C. using an ice bath and trifluoroacetic anhydride (3 equiv., 29 mmol) was slowly introduced followed by the dropwise addition of pyridine (4 equiv., 38 mmol) at 0° C. After warming to 25° C. and stirring for 5 hours the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate. The combined total organic layer was washed with 1N HCl and brine solution. The organic layer thus obtained was dried over anhydrous Na.sub.2SO.sub.4, filtered, and concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography over silica gel using 30% ethyl acetate in hexane as eluent to afford pure 3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.75 g, 57% yield) as colourless gummy mass.

(104) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.09 (d, 2H), 7.39 (d, 2H), 3.62 (t, 2H), 3.26 (t, 2H).

Step 2: Preparation of 3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

(105) 3-[4-(2-Bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.150 g, 0.467 mmol), 3,5-dimethyl-1H-pyrazole (1.5 equiv., 0.701 mmol) and potassium carbonate (0.30 g, 0.934 mmol) were dissolved in acetonitrile (5 mL) in a microwave vial and the mixture was heated in the presence of microwaves irradiation for 30 min at 100° C. Then the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate. The total combined organic layer was washed with water and brine solution. The organic layer thus obtained was dried over anhydrous Na.sub.2SO.sub.4, filtered, and concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography over silica gel using 30% ethyl acetate in hexane as eluent to afford pure 3-[4-[2-(3,5-dimethylpyrazol-1-yl)ethyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.03 g, 16% yield) as a colorless gummy mass. LC/MS (Method C) retention time=1.67 minutes, 337 (M+H).

(106) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.03 (m, 2H), 7.19 (m, 2H), 5.73 (s, 1H), 4.21 (t, 2H), 3.21 (t, 2H), 2.28 (S, 3H), 1.88 (s, 3H).

Example 6: This Example Illustrates the Preparation of Ethyl 1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazolyl]phenyl]ethyl]pyrazole-4-carboxylate (Compound 1.310 of Table T1 below)

(107) ##STR00035##

(108) 3-[4-(2-Bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.150 g, 0.467 mmol) and ethyl 1H-pyrazole-4-carboxylate (0.03 g, 0.08 mmol) were suspended in acetonitrile (1 mL) and potassium carbonate (0.30 g, 0.934 mmol) was introduced and the mixture was stirred for 16 hours. Then the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate. The total combined organic layer was washed with water and brine solution. The organic layer thus obtained was dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography over silica gel using 30% ethyl acetate in hexane as eluent to afford pure ethyl 1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]pyrazole-4-carboxylate (0.03 g, 20% yield) as a white solid. MP: 108-110° C. LC/MS (Method C) retention time=1.57 minutes, 381 (M+H).

(109) .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 8.05 (m, 2H), 7.96 (s, 1H), 7.69 (s, 1H), 7.23 (m, 2H), 4.41 (t, 2H), 4.28 (q, 2H) 3.30 (t, 2H), 1.33 (m, 3H).

(110) The following general procedure was performed in a combinatorial fashion using appropriate building blocks (compounds of Formulae (II) and (III)) to provide the compounds of Formula (I). The compounds prepared via the following combinatorial protocol were analyzed using LC/MS Method B.

(111) ##STR00036##

(112) By way of exemplification, 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.03 mmol in 1000 μL acetonitrile) were transferred to microwave vials containing amine derivative of formula (II) (0.03 mmol), potassium carbonate (0.06 mmol), and were stirred under microwaves irradiation at 120° C. for 20 minutes in the parallel microwave apparatus. The solvent was removed under a stream of nitrogen. The resultant crude residues were solubilized in a mixture of MeOH (250 μL) and DMA (500 μL) and directly submitted for preparative LC/MS purification which provided the compounds of formula (I). Structures of Isomers were assigned by NMR techniques.

(113) TABLE-US-00013 TABLE T1 Melting point (mp) and/or LC/MS data (retention time (t.sub.R)) for compounds of Formula (I): Mass charge LCMS t.sub.R [M + Me- mp Entry Compound name Structure (min) H].sup.+ thod (° C.) 1.1 3-[4-[[4-(1-ethyl-3- methyl-pyrazol-4- yl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 116.2- 118.2 1.2 3-[4-[[4-(1-ethyl-5- methyl-pyrazol-4- yl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 138.3- 140.1 1.3 3-[4-[(5-phenyltriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.08 272.3 A 1.4 3-[4-[(4-phenyltriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 161.5- 164.4 1.5 3-[4-[(4- cyclopropyltriazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 115.5- 117.2 1.6 3-[4-[[4-(3- methylimidazol-4- yl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 108.7- 110.3 1.7 [1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]triazol- 4-yl]methyl acetate 157.4- 160.4 1.8 3-[4-[[4-(3- thienyl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 160.2- 163.9 1.9 tert-butyl N-[[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]triazol-4- yl]methyl]carbamate 134.7- 136.9 1.10 3-[4-[(5,5-dimethyl- 4H-oxazol-2- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.71 326.2 A 1.11 3-[4-[[4- (ethoxymethyl)triazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 115.7- 117.6 1.12 3-[4-[[4-(4- methoxyphenyl)triazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 187.7- 196.2 1.13 3-[4-[[4-(4- fluorophenyl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 185.3- 189 1.14 3-[4-[[4-(p-tolyl)triazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 200.6- 204.2 1.15 3-[4-[(3,5- dimethylpyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 53-58 1.16 3-[4-(pyrazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 36-41 1.17 3-[4-[[3,5- bis(difluoromethyl) pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 53-58 1.18 3-[4-(imidazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 45-55 1.19 3-[4-(1,2,4-triazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.30 296.1 B 72-77 1.20 3-[4-[[5-methyl-3- (trifluoromethyl)pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 1.17 377.4 A 1.21 5-(trifluoromethyl)-3- [4-[[3- (trifluoromethyl)pyrazol- 1-yl]methyl]phenyl]- 1,2,4-oxadiazole 1.14 363.2 A 1.22 3-[4-[[4-(2- pyridyl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 160.2- 162.4 1.23 3-[4-[[4-(3- pyridyl)triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 159.8- 163.1 1.24 3-[4-[(4- cyclopentyltriazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 117.9- 118.8 1.25 trimethyl-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]triazol- 4-yl]silane 87.8- 89.5 1.26 3-[4-[(4-isobutyltriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 113.9- 115.7 1.27 3-[4-[(4-tert- butyltriazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 90.4- 92.3 1.28 3-[4-[[4- (phenoxymethyl)triazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 103.2- 104.9 1.29 3-[4-[[4-[(5-chloro-3- methoxy-2-pyridyl) oxymethyl]triazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 109.9- 113.3 1.30 N-[1-methyl-1-[1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]triazol- 4-yl]ethyl]benzamide 157.6- 161.9 1.31 3-[4-[[4-[1-(2,6- diethylphenyl)-5- methyl-pyrazol-4- yl]triazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.32 3-[4-(triazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.33 296.1 B 107.6- 109.5 1.33 3-[4-(triazol-2- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 105.4- 107.9 1.34 3-[4-(benzotriazol-2- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.85 346.1 B 112.4- 116.6 1.35 3-[4-(benzotriazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.67 346.1 B 142.3- 143.2 1.36 methyl 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate 1.50 354.1 B 122.8- 124.4 1.37 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate 1.35 354.1 B 174- 177.2 1.38 5-(trifluoromethyl)-3- [4-[[5-(trifluoromethyl)- 1,2,4-triazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole 1.09 405.2 A 1.39 5-(trifluoromethyl)-3- [4-[[3-(trifluoromethyl)- 1,2,4-triazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole 1.69 364.1 B 68.2- 70.1 1.40 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile 1.56 321.1 B 1.41 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile 120- 124 1.42 3-[4-[1-(6-methoxy-3- pyridyl)ethyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 1.26 350 A 1.43 dimethyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4,5-dicarboxylate 1.48 411.2 B 1.44 3-[4-[(4-iodopyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.83 421.1 B 1.45 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4,5-dicarbonitrile 1.59 345.2 B 1.46 3-[4-[(4,5- dichloroimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.76 363.1 B 1.47 3-[4-[(2- phenylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.14 371.2 B 1.48 5-(trifluoromethyl)-3- [4-[[2- (trifluoromethyl) benzimidazol-1- yl]methyl]phenyl]- 1,2,4-oxadiazole 1.93 413.2 B 1.49 3-[4-[(2- bromoimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.54 373.1 B 1.50 1-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]indol- 3-yl]ethanone 1.80 386.2 B 1.51 6-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]indole- 3-carbaldehyde 1.85 386.2 B 1.52 3-[4-[(5-methylindol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.05 358.2 B 1.53 3-[4-[(2- methylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.91 309.2 B 1.54 3-[4-[(6-fluoroindol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 2.05 362.2 B 1.55 5-(trifluoromethyl)-3- [4-[[4-(trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 1,2,4-oxadiazole 1.84 363.2 B 1.56 3-[4-[(2- isopropylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.03 337.2 B 1.57 5-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]indole- 3-carbaldehyde 1.75 402.2 B 1.58 2-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] benzimidazol-2- yl]acetonitrile 1.61 384.2 B 1.59 1-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrrol-2-yl]ethanone 1.80 336.2 B 1.60 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrrole- 3-carbonitrile 1.70 319.2 B 1.61 ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl] pyrazole-4-carboxylate 1.71 367.2 B 120- 130 1.62 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrrole- 2-carbaldehyde 1.73 322.2 B 1.63 3-[4-[(2- ethylbenzimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.24 373.2 B 1.64 3-[4-[(6-chloroindol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 00 2.14 378.2 B 1.65 3-[4-[[2-(4- fluorophenyl)imidazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 01 1.18 389.2 B 1.66 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]indole- 4-carboxylate 02 1.98 402.2 B 1.67 3-[4-[(4-chloropyrazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 03 1.77 329.2 B 1.68 methyl 2-methyl-5- (trifluoromethyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrrole- 3-carboxylate 04 1.96 434.4 B 1.69 3-[4-[(2,4,5- tribromoimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 05 1.98 528.5 B 1.70 2-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]indole- 3-carbaldehyde 06 1.81 386.2 B 1.71 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 2-carbaldehyde 07 1.46 323.2 B 1.72 3-[4-[(2-bromo-4,5- dichloro-imidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 08 1.97 441.0 B 1.73 3-[4-[[2-(4- pyridyl)benzimidazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 09 1.59 422.3 B 1.74 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]-5,6- dihydrocyclopenta[c] pyrrol-4-one 0 1.61 348.2 B 1.75 3-[4-[(5-methoxyindol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.91 374.2 B 1.76 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 4-carbonitrile 1.57 320.2 B 1.77 3-[4-[(4-bromopyrazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.80 373.1 B 1.78 3-[4-[(2,4- dimethylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.92 323.1 B 1.79 3-[4-[(4- bromoimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.55 373.0 B 1.80 ethyl 5-methyl-3-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl] imidazole-4- carboxylate 1.47 381.2 B 1.81 1,3-dimethyl-7-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] purine-2,6-dione 1.43 407.2 B 1.82 3-[4-[(4- phenylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.26 371.2 B 1.83 3-[4-[(4- methylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.88 309.1 B 1.84 ethyl 4-phenyl-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazole- 3-carboxylate 0 1.92 443.2 B 1.85 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 3-carbaldehyde 1.53 323.1 B 1.86 3-[4-(indazol-2- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.73 345.1 B 1.87 3-[4-(indazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.86 345.2 B 1.88 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4-carboxylate 1.34 353.1 B 1.89 methyl 3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4-carboxylate 1.42 353.1 B 1.90 5-(trifluoromethyl)-3- [4-[[4-(trifluoromethyl) imidazol- 1-yl]methyl]phenyl]- 1,2,4-oxadiazole 1.63 363.1 B 1.91 3-[4-[(4-bromo-2- methyl-imidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.53 387.0 B 1.92 3-[4-[(6-chloro-5- fluoro-benzimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.53 387.0 B 1.93 5-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 3-carbonitrile 1.74 397.1 B 1.94 3-[4-[(4- chlorobenzimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.71 334.1 B 1.95 3-[4-[(7- chlorobenzimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.67 379.1 B 1.96 3-[4-[(4-iodoimidazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.52 421.0 B 1.97 3-[3-methoxy-4-(1,2,4- triazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.38 325.1 B 102- 106 1.98 3-[4-(1,2,4-triazol-1- ylmethyl)-3- (trifluoromethyl) phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 1.53 363.1 B 1.99 3-[3-chloro-4-(1,2,4- triazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.44 329.0 B 63-71 1.100 3-[3-chloro-4-[(3,5- dimethylpyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.89 356.1 B 1.101 3-[3-fluoro-4-(1,2,4- triazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.35 313.1 B 52-63 1.102 3-[4-[(3,5- dimethylpyrazol-1- yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.89 356.1 B 50-56 1.103 3-[4-[(4- bromoimidazol-1- yl)methyl]-3- (trifluoromethyl) phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 1.99 440.0 B 1.104 dimethyl 1-[[2-chloro- 4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl] imidazole- 4,5-dicarboxylate 0 1.60 444.0 B 1.105 3-[3-chloro-4-[(2,4- dimethylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.02 356.1 B 1.106 1-[[2-chloro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4,5-dicarbonitrile 1.69 378.0 B 1.107 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-chloro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.69 405.9 B 1.108 methyl 1-[[2-chloro-4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate 1.48 387.0 B 1.109 3-[3-chloro-4-[(4- methylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.99 342.0 B 1.110 3-[4-(benzimidazol-1- ylmethyl)-3-chloro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.46 378.0 B 1.111 3-[3-chloro-4-[(4- chloropyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.91 362.0 B 1.112 3-[3-chloro-4- (imidazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.93 328.0 B 1.113 3-[3-chloro-4-[[5-(4- chlorophenyl)tetrazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.92 440.0 B 1.114 3-[3-chloro-4-[(4- iodopyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.97 453.9 B 1.115 3-[4-[(4-bromopyrazol- 1-yl)methyl]-3-chloro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.94 405.9 B 1.116 3-[4-[(5- bromoimidazol-1- yl)methyl]-3-methoxy- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.38 402.0 B 1.117 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-methoxy- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.62 402.0 B 1.118 dimethyl 1-[[2-fluoro- 4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole- 4,5-dicarboxylate 1.52 428.1 B 1.119 1-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4,5-dicarbonitrile 1.62 362.1 B 1.120 3-[4-[(4- bromoimidazol-1- yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.60 390.0 B 1.121 3-[4-[(4,5- dichloroimidazol-1- yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.80 380.0 B 1.122 methyl 1-[[2-fluoro-4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carboxylate 1.40 371.1 B 1.123 3-[3-fluoro-4-[(2- methylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.93 326.1 B 1.124 3-[3-fluoro-4-[(4- methylimidazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 0.95 326.1 B 1.125 3-[3-fluoro-4- (pyrrolo[2,3-b]pyridin- 7-ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.97 362.1 B 1.126 3-[4-(benzimidazol-1- ylmethyl)-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.33 362.1 B 1.127 3-[4-[(4-chloro-3,5- dimethyl-pyrazol-1- yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.99 374.1 B 1.128 3-[4-[(4-chloropyrazol- 1-yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.82 346.0 B 1.129 3-[3-fluoro-4- (imidazol-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.89 312.1 B 1.130 3-[4-[[5-(4- chlorophenyl)tetrazol- 1-yl]methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.84 424.0 B 1.131 3-[3-fluoro-4-[(4- iodopyrazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.87 438.0 B 1.132 3-[4-[(4-bromopyrazol- 1-yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.84 390.0 B 1.133 dimethyl 1-[[5-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-2- pyridyl]methyl] imidazole- 4,5-dicarboxylate 1.30 411.1 B 1.134 3-[6-[(2,4- dimethylimidazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 0.83 323.1 B 1.135 1-[[5-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-2- pyridyl]methyl] imidazole- 4,5-dicarbonitrile 1.44 345.1 B 1.136 3-[6-[(4- bromoimidazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.74 397.1 B 1.137 3-[6-[(4,5- dichloroimidazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.56 363.0 B 1.138 methyl 1-[[5-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-2- pyridyl]methyl]-1,2,4- triazole-3-carboxylate 1.16 354.1 B 1.139 3-[6-[(2- methylimidazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.77 309.1 B 1.140 3-[6-[(3,5- dimethylpyrazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.49 323.1 B 1.141 3-[6-(imidazol-1- ylmethyl)-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.72 295.1 B 1.142 3-[6-[[5-(4- chlorophenyl)tetrazol- 2-yl]methyl]-3-pyridyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 1.89 407.1 B 1.143 3-[6-(1,2,4-triazol-1- ylmethyl)-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.06 296.1 B 1.144 3-[6-[(4-iodopyrazol-1- yl)methyl]-3-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.56 373.0 B 1.145 3-[4-[(2,4- dimethylimidazol-1- yl)methyl]-3-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.01 340.1 B 1.146 5-(trifluoromethyl)-3- [4-[(3,4,5- trimethylpyrazol-1- yl)methyl]phenyl]- 1,2,4-oxadiazole B 99.4- 102 1.147 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 4-carboxylic acid 0.83 323.1 B 182- 192 1.148 N-cyclopropyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 4-carboxamide 1.44 345.1 B 189- 194 1.149 N,N-dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 4-carboxamide 124- 129 1.150 N-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazole- 4-carboxamide 156- 161 1.151 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4-carbaldehyde 1.26 323.1 B 1.152 3-[4-[[5-(2- bromophenyl)tetrazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.77 451.1 B 1.153 3-[4-[[5-(2- bromophenyl)tetrazol- 2-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.98 451.1 B 1.154 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]imidazole- 4-carbonitrile 0 1.41 320.1 B 1.155 3-[4-[(5,6- dichlorobenzotriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.98 414.1 B 1.156 N-[2-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] imidazol-4- yl]ethyl]acetamide 0.86 380.2 B 1.157 4-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrrolo [3,2-b]pyridine-2- carbonitrile 1.02 370.1 B 1.158 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrrolo [3,2-b]pyridine-2- carbonitrile 1.58 370.1 B 1.159 3-[4-[[6-(4- bromophenyl)sulfanyl- 5-chloro-benzotriazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.31 566.0 B 1.160 3-[4-[[5-(4- bromophenyl)sulfanyl- 6-chloro-benzotriazol- 2-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.46 566.0 B 1.161 ethyl 5-(4- chlorophenyl)-2- (trifluoromethyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole- 4-carboxylate 2.08 545.2 B 1.162 ethyl 5-(4- chlorophenyl)-2- (trifluoromethyl)-3-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole- 4-carboxylate 2.27 545.2 B 1.163 3-[4-[[5-chloro-6-(4- methoxyphenoxy) benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.06 502.2 B 1.164 3-[4-[[5-chloro-6-(4- methoxyphenoxy) benzotriazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 00 2.21 502.2 B 1.165 3-[4-[[5-(4- fluorophenyl)-3- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 01 2.14 457.2 B 1.166 3-[4-[[3-(4- fluorophenyl)-5- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 02 2.25 457.2 B 1.167 3-[4-[[5-(2,4- difluorophenyl)-3- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 03 2.14 475.2 B 1.168 3-[4-[[3-(2,4- difluorophenyl)-5- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 04 2.31 475.2 B 1.169 methyl 5-(2,5- difluorophenyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazole- 3-carboxylate 05 1.89 465.2 B 1.170 methyl 5-(2,5- difluorophenyl)-2-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazole- 3-carboxylate 06 2.22 465.2 B 1.171 5-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazol-3-ol 07 1.40 325.1 B 1.172 3-[4-[[5-(4- methoxyphenyl)-3- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 08 2.14 469.2 B 1.173 3-[4-[[3-(4- methoxyphenyl)-5- (trifluoromethyl) pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 09 2.22 469.2 B 1.174 3-[4-[[4-(4- chlorophenyl)-2- (difluoromethylsulfanyl) imidazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 2.08 487.1 B 1.175 3-[4-[(6-bromo-4,5- dimethyl-benzotriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.08 452.1 B 1.176 3-[4-[(6-bromo-4,5- dimethyl-benzotriazol- 2-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.27 452.1 B 1.177 3-[4-[[6-(1,3- benzodioxol-5-yloxy)- 5-chloro-benzotriazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.03 516.2 B 1.178 3-[4-[[5-(1,3- benzodioxol-5-yloxy)- 6-chloro-benzotriazol- 2-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.19 516.1 B 1.179 3-[4-[[4-chloro-5-(4- fluorophenoxy) benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.03 490.1 B 1.180 3-[4-[[7-chloro-6-(4- fluorophenoxy) benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.12 490.2 B 1.181 3-[4-[[4-chloro-5-(4- fluorophenoxy) benzotriazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.19 490.1 B 1.182 ethyl 5-(4- chlorophenyl)-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]-2- (trifluoromethylsulfanyl) imidazole-4- carboxylate 2.13 577.1 B 1.183 ethyl 5-(4- chlorophenyl)-3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]-2- (trifluoromethylsulfanyl) imidazole-4- carboxylate 2.30 577.1 B 1.184 ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] benzotriazole-5- carboxylate 0 1.84 418.2 B 1.185 ethyl 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] benzotriazole-5- carboxylate 2.00 418.2 B 1.186 ethyl 5-cyclopropyl-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazole- 3-carboxylate 1.87 407.2 B 1.187 ethyl 5-cyclopropyl-2- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazole- 3-carboxylate 2.08 407.2 B 1.188 ethyl 5-phenyl-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl] imidazole- 4-carboxylate 1.72 443.2 B 1.189 ethyl 5-phenyl-3-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] imidazole- 4-carboxylate 1.83 443.2 B 1.190 3-[4-[[2-methyl-6- (trifluoromethyl) benzimidazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.69 427.2 B 1.191 3-[4-[[2-methyl-5- (trifluoromethyl) benzimidazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.73 427.2 B 1.192 methyl 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] indazole-4-carboxylate 1.80 403.2 B 1.193 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] indazole-4-carboxylate 1.87 403.2 B 1.194 6-fluoro-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] indazole-3-carbonitrile 0 1.94 388.1 B 1.195 3-[4-[[4-chloro-6- (trifluoromethyl) benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.03 448.1 B 1.196 3-[4-[[7-chloro-5- (trifluoromethyl) benzotriazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.09 448.1 B 1.197 3-[4-[[4-chloro-6- (trifluoromethyl) benzotdazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0.00 448.1 B 1.198 3-[4-[(4,5- dimethylbenzotriazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.88 374.2 B 1.199 3-[4-[(4,5- dimethylbenzotriazol- 2-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.06 374.2 B 1.200 5-(trifluoromethyl)-2- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine 1.56 379.1 B 1.201 3-[4-[[5-(p- tolyl)tetrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.78 387.2 B 1.202 3-[4-[[5-(p- tolyl)tetrazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.03 387.2 B 1.203 N,N-dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine 1.44 339.2 B 1.204 ethyl 3- (difluoromethyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 0 1.82 417.2 B 1.205 ethyl 5- (difluoromethyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.97 417.2 B 1.206 3-[4-[(3-propylsulfanyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.76 370.1 B 1.207 3-[4-[(5-propylsulfanyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.82 370.1 B 1.208 3-[4-[(3-ethylsulfanyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.64 356.1 B 1.209 3-[4-[(5-ethylsulfanyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.70 356.1 B 1.210 4-chloro-5-(4- chlorophenyl)-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carbonitrile 2.18 464.1 B 1.211 4-chloro-5-(4- chlorophenyl)-2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carbonitrile 2.30 464.2 B 1.212 3-[4-[(3- benzylsulfanyl-1,2,4- triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.83 418.2 B 1.213 3-[4-[(3- benzylsulfanyl-1,2,4- triazol-4- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.89 418.2 B 1.214 5-methoxy-2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine 0 1.24 341.1 B 1.215 5-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine 1.32 341.1 B 1.216 3-[4-[[4-chloro-5-(2,2- difluoro-1,3- benzodioxol-4-yl)-3- methyl-pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.22 499.1 B 1.217 3-[4-[[4-chloro-3-(2,2- difluoro-1,3- benzodioxol-4-yl)-5- methyl-pyrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.26 499.1 B 1.218 3-(4-chlorophenyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carbonitrile 2.07 430.1 B 1.219 ethyl 2-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazol-3-yl]pyridine-3- carboxylate 1.72 444.2 B 1.220 3-[4-[[4-chloro-5-(2,4- dichlorophenyl)-3- (trifluoromethyl)pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 2.37 541.1 B 1.221 3-[4-[[4-chloro-3-(2,4- dichlorophenyl)-5- (trifluoromethyl)pyrazol- 1-yl]methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 2.46 541.1 B 1.222 5-(difluoromethyl)-2- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazol-3-amine 1.38 361.1 B 1.223 5-(4-methoxyphenyl)- 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-3-carbaldehyde 2.01 429.2 B 1.224 ethyl 5-propyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] imidazole-4-carboxylate 0 1.64 409.2 B 1.225 ethyl 5-propyl-3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] imidazole-4-carboxylate 1.67 409.2 B 1.226 3-[4-(1,2,4-triazol-4- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.13 296.1 B 1.227 4-[2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]tetrazol- 5-yl]benzaldehyde 1.81 401.2 B 1.228 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] indazole-3-carbonitrile 1.91 370.1 B 1.229 3-[4-[[4-(4- chlorophenyl)imidazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.53 405.1 B 1.230 3-[4-[[5-(4- chlorophenyl)tetrazol- 1-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.81 407.1 B 1.231 3-[4-[[5-(4- chlorophenyl)tetrazol- 2-yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.08 407.1 B 1.232 3-[4-[(5-bromo-3- methoxy-1,2,4-triazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.66 404.1 B 1.233 3-[4-[(3-bromo-5- methoxy-1,2,4-triazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.73 404.1 B 1.234 3-[4-[[5-(4-bromo-3- methyl- phenyl)tetrazol-1- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.94 465.1 B 1.235 3-[4-[[5-(4-bromo-3- methyl- phenyl)tetrazol-2- yl]methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 2.21 465.1 B 1.236 methyl 5-cyclopropyl- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.80 393.2 B 1.237 methyl 3-cyclopropyl- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.85 393.2 B 1.238 methyl 3- (methoxymethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.60 397.2 B 1.239 methyl 5- (methoxymethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.73 397.2 B 1.240 5-(2,6-difluorophenyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carbonitrile 1.84 433.0 B 1.241 5-(2,6-difluorophenyl)- 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carbonitrile 1.98 433.1 B 1.242 ethyl 3- (trifluoromethyl)-1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.93 435.2 B 1.243 3-[4-[(3-chloropyrazol- 1-yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.75 329.1 B 1.244 3-[4-(triazolo[4,5- b]pyridin-4- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 1.11 347.1 B 1.245 3-[4-(triazolo[4,5- b]pyridin-1- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.42 347.1 B 1.246 3-[4-(triazolo[4,5- b]pyridin-2- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.56 347.1 B 1.247 3-[4-(triazolo[4,5- b]pyridin-3- ylmethyl)phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.60 347.1 B 1.248 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 122- 129 1.249 N-(cyclopropylmethyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 195- 200 1.250 N-(2-methoxyethyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 132- 142 1.251 N-prop-2-ynyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 145- 155 1.252 ethyl 1-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 131- 135 1.253 3-[4-[(3,5- dimethylpyrazol-1- yl)methyl]-2-fluoro- phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.08 341 A 1.254 3-[4-[(6-methoxy-3- pyridyl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 0 A 1.255 1-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile 120- 123 1.256 2-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl]- 1,2,4-triazole-3- carbonitrile 1.03 337 (M − H) A 1.257 1-[[6-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-3- pyridyl]methyl]-1,2,4- triazole-3-carbonitrile 105- 108 1.258 2-[[6-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-3- pyridyl]methyl]-1,2,4- triazole-3-carbonitrile 0.89 322 A 1.259 N,N-diethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 86-96 1.260 N-methoxy-N-methyl- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 102- 112 1.261 morpholino-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazol-4-yl]methanone 125- 135 1.262 ~{tert}-butyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 81-91 1.263 isopropyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 1.13 381 A 1.264 propyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 00 105- 115 1.265 2- (dimethylamino)ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxylate 01 60-70 1.266 ~{N}-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 02 128- 138 1.267 ~{N}-ethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 03 166- 176 1.268 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrazole-4-carboxamide 04 0.86 338 A 1.269 ethyl 1-[[6-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]-3- pyridyl]methyl] pyrazole-4-carboxylate 05 88-90 1.270 methyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxylate 06 154- 156 1.271 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]triazole- 4-carboxylic acid 07 208- 210 1.272 N-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 08 0.92 352 C 1.273 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrazole- 4-carbaldehyde 09 91-96 1.274 N-ethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 0 193- 195 1.275 N-methoxy-N-methyl- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 135- 137 1.276 ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxylate 134- 136 1.277 N-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 198- 200 1.278 isopropyl 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxylate 146- 148 1.279 methyl 3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxylate 103- 107 1.280 N,N-dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 168- 170 1.281 N-(4-methoxyphenyl)- 1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 205- 207 1.282 N-(4-chlorophenyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 233- 235 1.283 N-(4-pyridyl)-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 204- 206 1.284 3-[5-[(3,5- dimethylpyrazol-1- yl)methyl]-2-pyridyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 0.95 324 A 1.285 N-methoxy-1-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl] methyl]pyrazol- 4-yl]methanimine 88-98 1.286 N-ethoxy-1-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrazol- 4-yl]methanimine 80-120 1.287 N-propoxy-1-[1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl] phenyl]methyl]pyrazol- 4-yl]methanimine 60-95 1.288 N-isopropoxy-1-[1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazol- 4-yl]methanimine 1.14; 1.16 Mass not detected A 1.289 N-benzyloxy-1-[1-[[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazol- 4-yl]methanimine 75-85 1.290 N-prop-2-ynoxy-1-[1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]methyl]pyrazol- 4-yl]methanimine 57-63 1.291 N-methyl-3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] triazole-4-carboxamide 222- 224 1.292 N-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] pyrrolidin-3-imine 1.10 341 B 1.293 N-methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] piperidin-4-imine 1.04 355 B 1.294 3-[4-[(5- methylsulfonyl-1,2,4- triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 0 119.2- 119.8 1.295 3-[4-[(5-methylsulfinyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 71.2- 73.7 1.296 3-[4-[(3- methylsulfonyl-1,2,4- triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 145.4- 146.4 1.297 3-[4-[(3-methylsulfinyl- 1,2,4-triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 114.4- 115.2 1.298 3-[4-[(5- methylsulfanyl-1,2,4- triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 72- 73.2 1.299 3-[4-[(3- methylsulfanyl-1,2,4- triazol-1- yl)methyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 88- 90.4 1.300 3-[4-(1- piperidylmethyl)phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 0.75 313 A 1.301 4-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] morpholine 0.68 315 A 1.302 3-[4- (thiomorpholinomethyl) phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 54.5- 56.6 1.303 3-[4-[1-(3,5- dimethylpyrazol-1- yl)ethyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.61 337 C 1.304 ethyl 1-[1-[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]ethyl] pyrazole-4-carboxylate 0 1.61 381 C 1.305 3-[4-[(4- methylsulfonylpiperazin- 1-yl)methyl]phenyl]- 5-(trifluoromethyl)- 1,2,4-oxadiazole 111.1- 114.9 1.306 2,6-dimethyl-4-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] morpholine 0.76; 0.81 343 A 1.307 (2R,6S)-2,6-dimethyl- 4-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] morpholine 0.76 343 A 1.308 (2R,6R)-2,6-dimethyl- 4-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]methyl] morpholine 0.81 343 A 1.309 3-[4-[2-(3,5- dimethylpyrazol-1- yl)ethyl]phenyl]-5- (trifluoromethyl)-1,2,4- oxadiazole 1.67 337 C 1.310 ethyl 1-[2-[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-yl] phenyl]ethyl]pyrazole- 4-carboxylate 1.57 381 C 108- 110 1.311 ethyl 1-[2-fluoro-2-[4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl]ethyl]pyrazole- 4-carboxylate 145- 147 1.312 2-morpholino-2-[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]phenyl]acetonitrile 1.07 339 A

BIOLOGICAL EXAMPLES

(114) General Examples of Leaf Disk Tests in Well Plates:

(115) Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse. The cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar. The leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation. Compounds to be tested are prepared as DMSO solutions (max. 10 mg/ml) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying. The inoculated leaf disks or segments are incubated under defined conditions (temperature, relative humidity, light, etc.) according to the respective test system. A single evaluation of disease level is carried out 3 to 14 days after inoculation, depending on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.

(116) General Examples of Liquid Culture Tests in Well Plates:

(117) Mycelia fragments or conidia suspensions of a fungus prepared either freshly from liquid cultures of the fungus or from cryogenic storage, are directly mixed into 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 is pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound. The test plates are incubated in the dark at 24° C. and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.

Example 1: Fungicidal Activity Against Puccinia recondita f. Sp. Tritici/Wheat/Leaf Disc Preventative (Brown Rust)

(118) Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19° C. and 75% relative humidity (rh) under a light regime of 12 hours light/12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 to 9 days after application).

(119) The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

(120) Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.15, 1.16, 1.18, 1.19, 1.21, 1.22, 1.23, 1.24, 1.25, 1.26, 1.27, 1.28, 1.29, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.37, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.52, 1.53, 1.55, 1.56, 1.57, 1.58, 1.60, 1.61, 1.62, 1.63, 1.65, 1.67, 1.73, 1.74, 1.75, 1.76, 1.79, 1.80, 1.81, 1.82, 1.83, 1.85, 1.86, 1.87, 1.88, 1.89, 1.90, 1.91, 1.93, 1.94, 1.95, 1.96, 1.99, 1.101, 1.102, 1.105, 1.107, 1.108, 1.109, 1.112, 1.118, 1.119, 1.120, 1.121, 1.122, 1.123, 1.124, 1.125, 1.126, 1.128, 1.129, 1.131, 1.132, 1.133, 1.135, 1.136, 1.137, 1.139, 1.141, 1.144, 1.145, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151, 1.154, 1.156, 1.157, 1.158, 1.171, 1.174, 1.186, 1.192, 1.193, 1.200, 1.203, 1.204, 1.206, 1.207, 1.208, 1.209, 1.212, 1.213, 1.214, 1.215, 1.219, 1.222, 1.224, 1.226, 1.229, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239, 1.240, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.249, 1.250, 1.251, 1.252, 1.253, 1.254, 1.255, 1.256, 1.259, 1.260, 1.261, 1.262, 1.263, 1.265, 1.266, 1.267, 1.268, 1.269, 1.270, 1.271, 1.273, 1.274, 1.275, 1.276, 1.277, 1.278, 1.279, 1.280, 1.281, 1.282, 1.283, 1.285, 1.286, 1.287, 1.288, 1.289, 1.290, 1.292, 1.294, 1.295, 1.296, 1.297, 1.298, 1.299, 1.301, 1.302, 1.303, 1.304, 1.305, 1.306, 1.308, 1.310 and 1.312.

Example 2: Fungicidal Activity Against Puccinia recondita f. Sp. Tritici/Wheat/Leaf Disc Curative (Brown Rust)

(121) Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are then inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19° C. and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19° C. and 75% relative humidity under a light regime of 12 hours light/12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 to 8 days after application).

(122) The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

(123) Compounds (from Table T1) 1.1, 1.2, 1.3, 1.5, 1.6, 1.8, 1.9, 1.10, 1.11, 1.15, 1.16, 1.18, 1.19, 1.22, 1.23, 1.25, 1.26, 1.27, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.38, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.49, 1.54, 1.55, 1.56, 1.61, 1.62, 1.67, 1.71, 1.76, 1.77, 1.78, 1.79, 1.80, 1.81, 1.82, 1.83, 1.85, 1.86, 1.87, 1.88, 1.89, 1.90, 1.91, 1.93, 1.96, 1.97, 1.99, 1.101, 1.102, 1.118, 1.119, 1.120, 1.121, 1.123, 1.124, 1.128, 1.129, 1.131, 1.132, 1.133, 1.134, 1.135, 1.136, 1.137, 1.141, 1.143, 1.144, 1.145, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151, 1.154, 1.156, 1.174, 1.192, 1.200, 1.203, 1.206, 1.207, 1.208, 1.209, 1.213, 1.214, 1.215, 1.219, 1.222, 1.226, 1.229, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.253, 1.254, 1.255, 1.256, 1.258, 1.259, 1.260, 1.261, 1.263, 1.264, 1.265, 1.266, 1.267, 1.268, 1.269, 1.270, 1.271, 1.272, 1.273, 1.274, 1.275, 1.277, 1.279, 1.280, 1.281, 1.283, 1.285, 1.287, 1.288, 1.290, 1.291, 1.292, 1.293, 1.294, 1.295, 1.296, 1.297, 1.298, 1.299, 1.302 1.303, 1.304, 1.305, 1.306 and 1.312.

Example 3: Fungicidal Activity Against Phakopsora pachyrhizi/Soybean/Leaf Disc Preventative (Asian Soybean Rust)

(124) Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leaf disc are kept at 20° C. with 12 h light/day and 75% rh. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 to 14 days after application).

(125) The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.

(126) Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.9, 1.10, 1.11, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.24, 1.25, 1.26, 1.27, 1.28, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.39, 1.40, 1.41, 1.42, 1.43, 1.49, 1.56, 1.59, 1.61, 1.79, 1.85, 1.86, 1.87, 1.88, 1.90, 1.91, 1.93, 1.96, 1.99, 1.101, 1.102, 1.129, 1.136, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151, 1.152, 1.153, 1.154, 1.156, 1.157, 1.158, 1.171, 1.174, 1.177, 1.184, 1.185, 1.186, 1.187, 1.190, 1.192, 1.193, 1.194, 1.195, 1.198, 1.200, 1.201, 1.203, 1.204, 1.205, 1.206, 1.207, 1.208, 1.209, 1.212, 1.213, 1.214, 1.215, 1.219, 1.222, 1.223, 1.224, 1.226, 1.227, 1.228, 1.229, 1.230, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239, 1.240, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.252, 1.253, 1.256, 1.259, 1.260, 1.261, 1.263, 1.264, 1.265, 1.266, 1.267, 1.268, 1.270, 1.273, 1.274, 1.275, 1.276, 1.277, 1.278, 1.279, 1.280, 1.283, 1.285, 1.286, 1.288, 1.290, 1.303, 1.304, 1.305, 1.306, 1.310 and 1.312.

Example 4: Fungicidal Activity Against Glomerella lagenarium (Colletotrichum lagenarium) Liquid Culture/Cucumber/Preventative (Anthracnose)

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

(128) The following compounds at 20 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control under the same conditions, which show extensive disease development.

(129) Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.23, 1.24, 1.25, 1.26, 1.27, 1.28, 1.29, 1.30, 1.32, 1.33, 1.34, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.51, 1.52, 1.54, 1.55, 1.56, 1.57, 1.58, 1.59, 1.60, 1.61, 1.62, 1.63, 1.64, 1.65, 1.66, 1.67, 1.68, 1.69, 1.70, 1.72, 1.73, 1.74, 1.75, 1.76, 1.77, 1.79, 1.80, 1.81, 1.82, 1.83, 1.84, 1.85, 1.86, 1.87, 1.88, 1.89, 1.90, 1.91, 1.92, 1.93, 1.94, 1.95, 1.96, 1.97, 1.98, 1.99, 1.100, 1.101, 1.102, 1.103, 1.104, 1.106, 1.107, 1.108, 1.109, 1.110, 1.111, 1.112, 1.113, 1.114, 1.115, 1.116, 1.117, 1.118, 1.119, 1.120, 1.121, 1.122, 1.124, 1.126, 1.127, 1.128, 1.129, 1.130, 1.131, 1.132, 1.133, 1.135, 1.136, 1.137, 1.138, 1.140, 1.142, 1.143, 1.144, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151, 1.152, 1.154, 1.157, 1.158, 1.171, 1.174, 1.184, 1.185, 1.186, 1.188, 1.189, 1.190, 1.191, 1.192, 1.193, 1.194, 1.198, 1.200, 1.203, 1.204, 1.205, 1.206, 1.207, 1.208, 1.209, 1.212, 1.213, 1.214, 1.215, 1.219, 1.222, 1.223, 1.224, 1.226, 1.227, 1.228, 1.229, 1.232, 1.233, 1.236, 1.237, 1.238, 1.239, 1.240, 1.243, 1.244, 1.245, 1.246, 1.247, 1.248, 1.249, 1.250, 1.251, 1.252, 1.253, 1.254, 1.255, 1.256, 1.257, 1.258, 1.259, 1.260, 1.261, 1.262, 1.263, 1.264, 1.265, 1.266, 1.267, 1.268, 1.269, 1.270, 1.273, 1.274, 1.275, 1.276, 1.277, 1.278, 1.279, 1.280, 1.281, 1.283, 1.284, 1.285, 1.286, 1.287, 1.288, 1.289, 1.290, 1.292, 1.294, 1.295, 1.296, 1.297, 1.298, 1.299 1.302. 1.303, 1.304, 1.305, 1.306, 1.307, 1.309 and 1.312.

Example 5: Fungicidal Activity Against Uromyces viciae-Fabae/Field Bean/Leaf Disc Preventative (Faba-Bean Rust)

(130) Field bean leaf discs are placed on water agar in multiwell plates (96-well format) and 10 μl of the formulated test compound diluted in acetone and a spreader pipetted onto the leaf disc. Two hours after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. The leaf discs are incubated in a climate cabinet at 22° C. with 18 hour day and 70% relative humidity. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 days after application).

(131) The following compounds at 100 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf discs under the same conditions, which show extensive disease development.

(132) Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, and 1.20.