Thienylpyri(mi)dinylazole

1. A compound of formula (I),

an N-oxide formed with the nitrogen in the pyridine ring, or a salt thereof;

in which

X 1 represents C—H or N;

R 1 represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 8 -allenyl, C 3 -C 8 -trialkylsilyl, C 4 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, acyloxy-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, aryl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, C 1 -C 4 -alkyl-C(O)—C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C(O)—C 1 -C 4 -alkyl, heterocyclyl-C(O)—C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)O—C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C(O)O—C 1 -C 4 -alkyl, heterocyclyl-C(O)O—C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 6 -alkyl, C 5 -C 10 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more R 16 ; H; C(O)NR 17 R 18 ; C(O)R 17 ; C(O)OR 17 ; S(O) 2 R 17 ; C(S)NR 17 R 18 ; C(S)R 17 ; or S(O) 2 NR 17 R 18 ;

R 2 represents H; cyano; halogen; C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, heterocyclyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -alkoxy; C 2 -C 8 -alkynyloxy, C 1 -C 8 -alkylthio, or C 3 -C 8 -trialkylsilyl, any of which is optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, amino, dimethylamino, and methoxy; C 6 -C 14 -aryl which is optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, NH 2 , heterocyclyl, C(O)OC 1 -C 6 -alkyl, OC(O)C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, and C 6 -C 14 -aryl; C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -alkoxy, C 2 -C 8 -alkynyloxy, C 1 -C 8 -alkylthio, or C 3 -C 8 -trialkylsilyl, any of which is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, heterocyclyl, C(O)OC 1 -C 6 -alkyl, OC(O)C 1 -C 6 -alkyl, C 2 -C 4 -alkoxy, and C 6 -C 14 -aryl; heterocyclyl which is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, heterocyclyl, C(O)OC 1 -C 6 -alkyl, OC(O)C 1 -C 6 -alkyl, C 2 -C 4 -alkoxy, and C 6 -C 14 -aryl;

R 3 represents H; halogen; cyano; OR 11 ; C(O)OR 11 ; C(O)SR 11 ; C(S)OR 11 ; C(O)R 11 ; C(S)R 11 ; SR 11 ; NR 9 R 10 ; C(O)NR 11 R 20 ; C(S)NR 11 R 20 ; N(R 17 )C(O)OR 11 ; N═CH—NR 17 R 18 ; NH—CH—NR 17 R 18 ; N═CR 17 R 18 ; N(C 1 -C 6 -alkyl)-NHR 17 ; N═C(H)OR 17 ; N═C(OR 17 )R 18 ; N═C(SR 17 )R 18 ; C(═NR 17 )NR 17 R 18 ; SO(═NR 17 )R 18 ; SO 2 NR 11 R 20 ; C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 8 -alkynyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of R 16 ; or SO 2 R 11 ; with the proviso that if X 1 is N, then R 3 is not aniline;

R 4 and R 5 represent independently of each other H; F; Cl; Br; I; cyano; nitro; OH; SH; NH 2 ; C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 6 -C 14 -aryl, C 1 -C 4 -alkoxy, O—(C 6 -C 14 -aryl), S—(C 1 -C 4 -alky), S(O)—(C 1 -C 6 -alkyl), C(O)—(C 1 -C 6 -alkyl), C 3 -C 8 -trialkylsilyl, heteroaryl, or heterocyclyl, any of which is optionally substituted by one or more R 16 ; or R 4 and R 5 form, together with the carbon atoms to which they are bonded, a 5- to 8-membered ring which may contain one, two, three, or four heteroatoms selected from oxygen, sulphur, or NR 19 , which may be optionally halogen, oxygen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 3 -C 6 -cycloalkyl;

R 6 represents H; halogen; OH; nitro; cyano; C(O)NR 11 R 20 ; C(O)OR 11 ; SO 2 R 11 ; SR 11 ; S(O)R 11 ; C(S)R 11 ; C(S)NR 11 R 20 ; SO 2 NR 11 R 20 ; NR 9 R 10 ; N═CR 17 R 18 ; C(═NR 17 )R 18 ; OR 11 ; C(O)SR 11 ; C(S)OR 11 ; C(O)OC(O)R 11 ; C(O)R 11 ; N(R 17 )C(O)R 11 ; N(R 17 )C(O)OR 11 ; N═C—NR 17 R 18 ; N(C 1 -C 6 -alkyl)-NR 17 ; N═C(H)OR 17 ; N═C(OR 17 )R 18 ; N═C(SR 17 )R 18 ; C(═NR 17 )NR 17 R 18 ; SO(═NR 17 )R 18 ; SO 2 NR 11 R 20 ; or C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C(O)—C 1 -C 6 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -halogenalkoxy, C 1 -C 6 -alkylsulphenyl, C 1 -C 6 -alkylsulfanyl, C 3 -C 8 -trialkylsilyl, C 6 -C 10 -aryl, heteroaryl, heterocyclyl, or C 6 -C 10 -aryloxy, any of which is optionally substituted by one or more R 16 ;

R 7 represents H; halogen; cyano; nitro; C 1 -C 6 -alkyl; C 3 -C 6 -cycloalkyl; C 2 -C 6 -alkenyl; C 2 -C 6 -alkynyl; C 5 -C 10 -aryl; heteroaryl; heterocyclyl;

or R 6 and R 7 form, together with the carbon atoms to which they are bonded, a 5- to 7-membered ring which may contain one, two, three, or four heteroatoms selected from oxygen, sulphur, or NR 19 , and which may be optionally substituted with one or more substituents selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, halogen, hydroxyl, amino, cyano, and nitro;

R 8 represents H; halogen; cyano; C 1 -C 6 -alkyl; C 3 -C 6 -cycloalkyl; C 2 -C 6 -alkenyl; C 2 -C 6 -alkynyl; C 6 -C 10 -aryl; heteroaryl; heterocyclyl;

or R 7 and R 8 form, together with the carbon atoms to which they are bonded, a 5- to 7-membered ring which may contain one, two, three, or four heteroatoms selected from oxygen, sulphur, or NR 19 , and which may be optionally substituted with one or more substituents selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, halogen, hydroxyl, amino, cyano, and nitro;

R 9 and R 10 represent H; C(S)R 14 ; C(O)R 14 ; SO 2 R 14 ; C(O)OR 14 ; OR 14 ; C(O)NR 14 R 15 ; C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, OH, cyano, C 1 -C 6 -alkyl, O—C(O)R 17 , O—P(O)(OR 17 ) 2 , O—B(OR 17 ) 2 , and O—(C 1 -C 4 -alkyl); or C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 6 -C 14 -aryl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl, or heteroaryl-C 1 -C 6 -alkyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, OH, cyano, C 1 -C 6 alkyl, O—C(O)R 17 , O—P(O)(OR 17 ) 2 , O—B(OR 17 ) 2 , and O—(C 1 -C 4 -alkyl);

R 11 and R 20 represent H; C(S)R 12 ; C(O)R 12 ; SO 2 R 12 ; C(O)OR 12 ; OR 12 ; C(O)NR 12 R 13 ; or C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one more substituents selected from the group consisting of F, Cl, Br, OH, cyano, C 1 -C 6 -alkyl, O—C(O)R 17 , O—P(O)(OR 17 ) 2 , O—B(OR 17 ) 2 , and O—(C 1 -C 4 -alkyl);

R 12 and R 13 represent H; or C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, carbonyl, cyano, C 1 -C 6 -alkyl, and C 1 -C 4 -alkoxy;

R 14 and R 15 represent H; C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, cyano, methoxy, nitro, trifluoromethyl, and difluoromethyl; C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 6 -C 14 -aryl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl, or heteroaryl-C 1 -C 6 -alkyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, cyano, methoxy, nitro, trifluoromethyl, difluoromethyl, C 1 -C 6 -alkyl, O—C(O)R 17 , O—P(O)(OR 17 ) 2 , O—B(OR 17 ) 2 , and O—(C 1 -C 4 -alkyl); or C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 6 -alkyl, O—C(O)R 17 , O—P(O)(OR 17 ) 2 , O—B(OR 17 ) 2 , or O—(C 1 -C 4 -alkyl);

R 16 represents OH; F; Cl; Br; I; cyano; NH—C(O)R 17 ; NR 17 R 18 ; C(O)R 17 ; C(O)OR 17 ; C(O)NR 17 R 18 ; SO 2 R 17 ; OC(O)R 17 ; or C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy, S—(C 1 -C 4 -alkyl), O—(C 3 -C 8 -cycloalkyl), S—(C 3 -C 8 -cycloalkyl), C 6 -C 14 -aryl, O—(C 6 -C 14 -aryl), S—(C 6 -C 14 -aryl), heterocyclyl, or heteroaryl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, carbonyl, cyano, C 1 -C 6 -alkyl, and C 1 -C 4 -alkoxy;

R 17 and R 18 represent C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, or benzyl, any of which is optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, OH, and cyano; H; or aryl;

R 19 represents H, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C(S)R 14 , C(O)R 14 , SO 2 R 14 , or C(O)OR 14 ;

with the proviso that the compound of formula (I) is not 4-[3-(2-thienyl)-1H-pyrazol-4-yl]quinoline or phenyl substituted 4-phenyl-6-[1-phenyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyrimidine-2(1H)-thiones.

2. The compound of claim 1 ,

in which

X 1 represents CH or N;

R 1 represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, —CH═CHCH 3 , —C≡CCH 3 , but-2-en-1-yl, but-3-en-2-yl, but-2-yn-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —CH═C═CH 2 , trimethylsilyl, tert-butyldimethylsilyl, cyclohexenyl, methoxymethyl, ethoxymethyl, methoxyethyl, tert-butoxy-methyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methylacetate, ethylacetate, pyridin-2-ylmethyl, pyridin-3-ylmethyl, pyridin-4-ylmethyl, (1,3-thiazol-5-yl)methyl, (1,3-thiazol-4-yl)methyl, (1,3-thiazol-3-yl)methyl, (1,3-oxazol-5-yl)methyl, (1,3-oxa-4-yl)methyl, (1,3-oxa-3-yl)methyl, phenylmethyl, phenylethyl, methylthio, ethylthio, n-propylthio, iso-propylthio, tertbutylthio, n-butylthio, sec-butylthio, iso-butylthio, methylthioalkyl, phenyl, benzyl, naphthalenyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydro-pyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, or morpholine, any of which is optionally substituted with one or more R 16 ; H; C(O)NR 17 R 18 ; C(O)R 17 ; C(O)OR 17 ; S(O) 2 R 17 ; C(S)NR 17 R 18 ; C(S)R 17 ; or S(O) 2 NR 17 R 18 ;

R 2 represents H; cyano; Br; Cl; F; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —CH 2 CH═CH 2 , —C≡CH, —C≡CCH 3 , —CH 2 C≡CH, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, —O—CH 2 C≡CH, methylthio, ethylthio, n-propylthio, iso-propylthio, tertbutylthio, n-butylthio, sec-butylthio, iso-butylthio, or trimethylsilyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, cyano, amino, dimethylamino, and methoxy;

R 3 represents H; F; Cl; Br; cyano; OR 11 ; C(O)OR 11 ; C(O)R 11 ; NR 9 R 10 ; C(O)NR 11 R 20 ; N═C(OR 17 )R 18 ; N═C(SR 17 )R 18 ; SO(═NR 17 )R 18 ; N(C 1 -C 6 -alkyl)-NHR 17 ; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —C 2 C≡CH, —C≡CH, —CH═CHCH 3 , —C≡CCH 3 , but-2-en-1-yl, but-3-en-2-yl, but-2-yn-1-yl, phenyl, or benzyl, any of which is optionally substituted by one or more R 16 ;

R 4 and R 5 represent independently of each other H; F; Cl; Br; cyano; nitro; OH; SH; or methyl, ethyl, cyclopropyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, phenyl, or methoxy, any of which is optionally substituted with one or more R 16 ;

or R 4 and R 5 form, together with the carbon atoms to which they are bonded, a 5- to 8-membered ring which may contain one, two, three, or four heteroatoms selected from oxygen, sulphur, or NR 19 , which may be optionally substituted by one or more F, Cl, Br, oxygen, cyano, methyl, ethyl, methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy, or cyclopropyl;

R 6 represents H; F; Cl; Br; OH; nitro; cyano; C 2 -alkynyl; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, tertbutylthio, n-butylthio, sec-butylthio, or iso-butylthio, any of which is optionally substituted by one or more R 16 ;

R 7 represents H, F, Cl, Br, cyano, nitro, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, or —C≡CH;

R 8 represents H; F; Cl; Br; cyano; methyl; ethyl; n-propyl; iso-propyl; n-butyl; iso-butyl; sec-butyl; tert-butyl; n-pentyl; cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; CH═CH 2 ; —CH 2 CH═CH 2 ; —CH 2 C≡CH; —C≡CH;

or R 7 and R 8 form, together with the carbon atoms to which they are bonded, a 5- to 7-membered ring which may contain one, two, three, or four heteroatoms selected from oxygen, sulphur, or NR 19 , which may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, F, Cl, Br, hydroxyl, amino, cyano, and nitro;

R 9 and R 10 represent H; C(S)R 14 ; C(O)R 14 ; SO 2 R 14 ; C(O)OR 14 ; OR 14 ; C(O)NR 14 R 15 ; or C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, heterocyclyl, or heteroaryl, ary of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, OH, cyano, methyl, methoxy substituted methyl, ethyl, isopropyl, sec-butyl, iso-butyl, tert-butyl, cyclopropyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, —CH═CH═CH 3 , —C≡CCH 3 , but-2-en-1-yl, but-3-en-2-yl, but-2-yn-1-yl, phenyl, oxetanyl, methylcyclopropyl, and benzyl;

R 11 and R 20 represent H; C(S)R 12 ; C(O)R 12 ; SO 2 R 12 ; C(O)OR 12 ; OR 12 ; C(O)NR 12 R 13 ; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, O—C(O)Me, O—C(O)Et, O—P(O)(OMe) 2 , O—B(OMe) 2 , O—B(OEt) 2 , methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy substituted methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, or phenyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, OH, and cyano;

R 12 and R 13 represent H; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, or phenyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, carbonyl, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl or methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, and tert-butoxy;

R 10 and R 15 represent methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, or phenyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, cyano, methoxy, nitro, trifluoromethyl, difluoromethyl, cyclopropylmethyl, benzyl, 3-thienyl, 2-thienyl; or hydrogen;

R 16 represents OH; F; Cl; Br; I; cyano; NH—C(O)R 17 ; NR 17 R 18 ; C(O)R 17 ; C(O)OR 17 ; C(O)NR 17 R 18 ; SO 2 R 17 ; or methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, phenyl, methoxy, ethoxy, tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 2-piperazinyl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, or pyrazin-2-yl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, I, OH, carbonyl, cyano, methyl, ethyl, and methoxy;

R 17 and R 18 represent methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, or benzyl, any of which is optionally substituted by one or more substituents selected from the group consisting of F, Cl, Br, OH, and cyano; or H;

R 19 represents H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH═CH 2 , —CH 2 CH═CH 2 , —CH 2 C≡CH, —C≡CH, C(S)R 14 , C(O)R 14 , SO 2 R 14 , or C(O)OR 14 ;

an N-oxide formed with the nitrogen in the pyridine ring, or a salt thereof.

3. The compound of claim 1 ,

in which

X 1 represents CH or N;

R 1 represents H, methyl, ethyl, propan-2-yl, isobutyl, butan-2-yl, 2-methylpropyl, 3-methylbut-2-en-1-yl, 4-methylpentan-2-yl, 3-methylbutyl, 2,2-dimethylpropyl, pentan-3-yl, terbutyl, 4-methylpentan-2-yl, 3-dimethylbutan-2-yl, 3-methylbutan-2-yl, 2,2,2-trifluoroethyl, 2-chloroethyl, 2-fluoroethyl, 2-methoxyethyl, methoxymethyl, 1-methoxypropan-2-yl, 2-(trifluoromethoxy)ethyl, cyanomethyl, benzyl, 2-phenylethyl, —CH 2 C(O)OEt, tetrahydrofuran-2-ylmethyl, ethylmorpholine, 3-dimethylamino-2-methylpropyl, allyl, 3,3-dichloroprop-2-en-1-yl, but-3-en-2-yl, prop-2-yn-1-yl, but-2-yn-1-yl, cyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, (2,2-dichlorcyclopropyl)methyl, cyclopropylmethyl, cyanoethyl, 2,2-difluoroethyl, ethoxyethyl, orthocyanobenzyl, orthofluorobenzyl, methoxyethoxyethyl, trifluoromethoxyethyl, cyclopropylmethyl, tetrahydro-2H-pyran-2-yl, phenyl, 2-fluorobenzyl, acetyl, ethoxycarbonyl, methylsulfonyl, isopropylaminocarbonyl, 2-cyanoethyl, 2,2-difluoroethyl, 2-ethoxyethyl, cyclopropylmethyl, 2-cyanobenzyl, or 2,3-difluorobenzyl;

R 2 represents H, cyano, cyclopropyl, methyl, Br, methylthio, trimethylsilyl, methyl, prop-1-ynyl, propyl, F, or Cl;

R 3 represents H, Cl, Br, cyano, isopropylcarbamoyl, methoxy, propylamine, dimethylamino, hydrazine, benzylamino, amino, acetylamino, prop-2-yn-1-ylamino, N-Bis(cyclopropylcarbonyl)amino, N-benzyl-N-isopropylcarbonylamino, n-propionylamino, isobutyrylamino, (cyclobutylcarbonyl)amino, (cyclopropylcarbonyl)amino, (methoxyacetyl)amino, 2-methoxypropanoyl, (2-methylbutanoyl)amino, but-2-enoylamino, prop-2-enoylamino, 3-(dimethylamino)prop-2-enoyl]amino, (3,3,3-trifluoropropanoyl)amino, 3,3-difluoropropanoylamino, 2-(cyclopropylethynyl), (cyclopropylacetyl)amino; (3-methylbutanoyl)amino, 2-hydroxypropanoylamino, acetylacetamido, 3-oxetanylamino, cyclopropylamino, benzoylamino, 2,2-dimethylpropanoylamino, (3-thienylcarbonyl)amino, (2-thienylcarbonyl)amino, isopropylamino, allylamino, cyclopropylmethylamino, 1-methyl-2-methoxyethylamino, 1-methylpropylamino, or formamido;

R 4 represents H;

R 5 represents H;

R 6 represents H, Cl, F, acetyl, N-butylcarboxamido, methyl, cyano, C 2 -C 8 -alkynyl, or C 3 -C 8 -cycloalkyl;

R 7 represents H or Cl;

R 8 represents H or Cl;

an N-oxide formed with the nitrogen in the pyridine ring, or a salt thereof.

4. The compound of claim 1 ,

in which

X 1 represents CH or N;

R 1 represents propan-2-yl, butan-2-yl, 2-methylpropyl, prop-2-yn-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, 2,2,2-trifluoroethyl, 2-fluorobenzyl, 2-(trifluoromethoxy)ethyl, 2-fluoroethyl, ethyl, but-1-en-3-yl, cyanomethyl, 3-pentyl, 2-chloroethyl, methoxymethyl, 2-cyanoethyl, 2,2-difluoroethyl, 2-ethoxyethyl, cyclopropylmethyl, 2-cyanobenzyl, 2,3-difluorobenzyl, or methyl;

R 2 represents H, methyl, or prop-1-ynyl;

R 3 represents H, acetylamino, n-propionylamino, isobutyrylamino, (cyclopropylcarbonyl)amino, (methoxyacetyl)amino, 2-methoxypropanoylamino, (2-methylbutanoyl)amino, but-2-enoylamino, prop-2-enoylamino, 3-(dimethylamino)prop-2-enoylamino, 3,3,3-trifluoropropanoylamino, 3,3-difluoropropanoylamino, amino, (cyclobutylcarbonyl)amino, (cyclopropylacetyl)amino, (3-methylbutanoyl)amino, 2-hydroxypropanoylamino, acetylacetamido, 3-oxetanylamino, cyclopropylamino, benzoylamino, or 2,2-dimethylpropanoylamino;

R 4 represents H;

R 5 represents H;

R 6 represents Cl or F;

R 7 represents H; and

R 8 represents H;

an N-oxide formed with the nitrogen in the pyridine ring, or a salt thereof.

5. A composition comprising at least one compound of formula (I) according to claim 1 and at least one extender or surfactant for controlling phytopathogenic harmful and mycotoxin producing fungi.

6. A method for controlling unwanted microorganisms, comprising applying one or more compounds of formula (I) according to claim 1 to a plant, plant part, or surroundings of a plant.

7. A method for controlling phytopathogenic harmful and mycotoxin producing fungi, comprising applying one or more compounds of formula (I) according to claim 1 to the microorganisms, their habitat, or both.

8. A composition comprising at least one compound of formula (I) according to claim 1 and an extender, surfactant, or both, for controlling unwanted microorganisms.

9. A method for treating transgenic plants comprising applying one or more compounds of formula (I) according to claim 1 to a plant, plant part, surroundings of a plant, or a mixture thereof.

10. A compound of claim 1 , which is