WO2008046856A2 - Fungicidal compositions - Google Patents

Abstract

Fungicidal compositions for controlling plant pathogenic fungi, comprising at least one compound of formula (I) and at least one active ingredient II, selected from the groups (A) to (F) as defined in the claims and the description, in a synergistic amount.

Description

 Fungicidal compositions

description

The present invention relates to fungicidal compositions containing as active components

1) at least one compound of the formula I.

wherein the substituents have the following meanings:

R ¹ is -hydrogen, halogen, cyano, nitro, _Ci-C8-alkyl, d-Cs-haloalkyl, d-Cs-H yd roxya I ky I, C 1 -Cs-Al koxy-C 1 -C ₈ -a I ky I, C2-C8 AI ke ny I oxy-C 1 -C ₈ -a I ky I, _{C2-C8-alkynyloxy-Ci-C 8} alkyl, C ₃ -C ₈ cycloalkyloxy-C ₈ alkyl, Ci-C ₈ - alkoxyalkyloxy-C ₈ alkyl, benzyloxy-Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -Al kinyl, _{C3-C8-haloalkynyl, Ci-C8-alkoxy,} Ci-C ₈ - haloalkoxy, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl, hydroxyimino or a group

wherein p is 1, 2, 3, 4 or 5 and # is the point of attachment to the pyrazolopyrimidine skeleton; wherein the aliphatic and alicyclic groups may contain one, two, three or four identical or different R ^a ;

-C (= W ¹ ) NH ₂ , where W ¹ means:

W ^{1 is} S, O, NH, N-OH or N-OW ² , where W ^{2 is} C 1 -C ₈ -alkyl or C ₆ -C 14 -aryl-C 1 -C ₈ -alkyl, where W ^{2 is} one, two, may contain three or four identical or different groups R ^a ;

-C (W ³ ) = N (W ⁴ ) where W ³ , W ^{4 are}

W ^{3 is} hydrogen or C 1 -C ₈ -alkyl;

W ^{4 is} C 1 -C ₈ -alkyl, phenyl or phenylamino;

wherein W ³ and W ^{4 may} each independently contain one, two, three or four identical or different groups R ^a ; -CW ⁵ (= O), where W ⁵ means:

W ^{5 is} hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, benzyl, where W ^{5 is} one, two, three or four identical or different Groups R ^a may contain;

-CONW ⁶ W ⁷ , CONW ⁷ -N (W ⁷ ) ₂ , CO-NW ⁷ -OW ⁷ , COOW ⁸ , C (S) OW ⁷ , C (O) SW ⁷ , C (S) SW ⁷ , SW ⁷ , SOOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁷ , SON (W ⁷ ) ₂ , SO ₂ N (W ⁷ ) ₂ , P (O) (OW ⁷ ) ₂ , NW ⁷ OW ⁷ , B (OW ⁷ ) ₂ , - (CW ⁷ ₂ ) ₀ - ₆ -NW ⁷ ₂ or - (CW ⁷ ₂ ) ₀ - ₆ -NW ⁷ -

NW ⁷ ₂ ; where W ⁶ , W ⁷ , W ^{8 are} each independently:

W ^{6 is} C ₁ -C 10 -alkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₆ -C ₄ -aryl, C ₆ -C ₄ -alkyl -Aryl-C 1 -C ₈ -alkyl;

W ^{7 is} hydrogen or one of the radicals mentioned at W ⁶ ;

two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ can also together form a saturated or partially unsaturated cycle having 3, 4, 5 or 6 carbon atoms, the 1 or 2 further hetero atoms selected from nitrogen, sulfur and oxygen may contain;

W ^{8 is} hydrogen, a cation, C ₁ -C ₈ -alkyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl or C ₆ -Ci4-aryl-Ci-C ₈ alkyl;

W ⁶ , W ⁷ , W ⁸ or a cycle formed from W ⁷ or W ⁷ and W ⁶ may each independently contain one, two, three or four identical or different groups R ^a ;

saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl which may contain one, two, three or four identical or different groups R ^a ;

where R ^a means:

R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, Ci-C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Al kinyl, C ₃ -C ₈ - haloalkynyl, C4-Cio-alkadienyl, C ₈ alkoxy, Ci-C ₈ -Halogenalk- oxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy,

C ₃ -C ₈ -haloalkynyloxy, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₃ -C ₈ -cycloalkoxy, C ₃ -C ₈ -halocycloalkoxy, C 1 -C ₈ -cycloalkenyloxy, C 1 -C 10 -cycloalkyl, C 1 -C 5 -alkylcarbonyloxy, C 1 -C ₈ -alkoxycarbonyloxy, aminocarbonyloxy, C 1 -C ₈ -alkylaminocarbonyloxy, C 1 -C -alkylaminocarbonyloxy, C 1 -C ₈ -alkylthiocarbonyloxy, C 1 -C ₈ -alkoxythiocarbonyloxy, aminothiocarbonyloxy, C 1 -C ₈ -alkylaminothiocarbonyloxy, di-C 1 -C 6 -alkylaminothiocarbonyloxy C 1 -C ₈ -

Alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothiocarbonyl, C 1 -C 6 -alkylene, oxy-C ₂ -C ₄ -alkylene, oxy-C 1 -C ₄ -alkyleneoxy, CHCH 2, imino (NHNH), (C 1 -C ₄ -alkoxy) imino (= N- (C 1 -C ₄ -alkoxy)), (C 1 -C ₄ -alkyl) -imino (= N- (C 1 -C ₄ -alkyl)), -C (= O) -A, -C ( = O) -OA, -C (= O) -N (A ') A, C (A') (= N-OA), N (A ¹ Y, N (A ') - C (= O) - A, N (A ") -C (= O) -N (A ') A, S (= O) _m -A,

S (= O) _m -OA, S (= O) _m -N (A ') A, -Si (C ₁ -C ₆ -alkyl) ₃ , phenyl, naphthyl, five, six, seven, eight a nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S; where m, A, A 'and A "mean:

m is 0, 1 or 2;

A, A ', A "independently of one another hydrogen, Ci-C ₈ alkyl, C ₂ -C ₈ alkene yl, C ₂ -C ₈ -alkyl kinyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ Cycloalkenyl, phenyl, where the organic radicals may be partially or fully halogenated and / or monosubstituted or polysubstituted by nitro, cyanoato, cyano, C 1 -C ₄ -alkoxy, and A and A may also be used together with the atoms to which they are attached represent a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S.

wherein the aliphatic, alicyclic and / or aromatic groups in

R ^{a may in} turn carry one, two or three identical or different groups R ^b :

R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, Ci-C ₈ alkyl, C ₂ -C ₈ alkene yl, C ₂ -C ₈ -alkyl kinyl, d-do-alkadienyl, C ₃ -C ₈ - cycloalkyl, C ₃ -C ₈ -CyCIo- alkenyl, Cs-do-bicycloalkyl, C ₈ alkoxy, C 2 -C ₈ alkenyloxy, C ₂ -C ₈ - alkynyloxy, C ₃ -C ₈ cycloalkoxy, C ₃ -C ₈ -cycloalkenyloxy, Aminothiocar- carbonyl, d-Cs-alkyl-carbonyloxy, d-Cs-alkylaminothiocarbonyl, di-Ci- C ₈ -alkylaminothiocarbonyl, C ₈ alkylthio, _{Ci-C8-alkylsulfinyl,} Ci-C ₈ -alkylsulfonyl, C ₆ -C ₄ -aryl, C ₆ -C ₄ -aryloxy, C ₆ -C ₄ -arylthio, C ₆ -C ₄ -aryl

Ci-Cβ-alkoxy, C6-Ci4-aryl-Ci-C6-alkyl, five to ten membered saturated, partially unsaturated or aromatic heterocycle, including tend, two, three or four heteroatoms from the group O, N and S, heterocyclyloxy, heteroaryloxy, heteroarylthio, -C (= O) -A, -C (= O) - OA, -C (= O) -N (A ') A, C (A ¹ X = N-OA), N (A') A; wherein the aliphatic, alicyclic or aromatic groups may be partially or fully halogenated and / or substituted by C 1 -C 8 -alkyl and / or C 1 -C ₈ -haloalkyl groups;

R ² is hydrogen, halogen, cyano, Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} Ci-C ₈ -AIk- oxy, _{Ci-C8-haloalkoxy, Ci-C8} alkylthio, Ci-C ₈ - alkylsulfinyl, Ci-C ₈ alkyl sulfonyl, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl; wherein R ² may contain one, two, three or four identical or different groups R ^a

X is hydrogen, halogen, hydroxy, cyano, N (A ') A, C ₈ alkoxy, Ci-C ₈ genalkoxy -HaIo-, _Ci-C8 alkylthio, _{Ci-C8-alkylsulfinyl,} Ci-C ₈ alkylsulfonyl, Ci-C ₈ - alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -

Alkynyl, C ₃ -C ₈ haloalkynyl, _{cyano-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl;}

Y is a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and

Sulfur, wherein the heterocycle is unsubstituted or substituted with one, two, three or four identical or different substituents L;

Phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L;

where L means:

L is halogen, cyano, nitro, hydroxy, cyanato (OCN), C ₈ alkyl, C ₈ - haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Alkynyl, C ₃ -C ₈ -

Haloalkynyl, C ₄ -Cio-alkadienyl, C ₄ -Cio-Halogenalkadienyl, Ci-C ₈ -AIk- oxy, _{Ci-C8-haloalkoxy, Ci-C8-alkylcarbonyloxy,} Ci-C ₈ alkylsulfonyl oxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy, C ₂ - C ₈ haloalkynyloxy, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ - cycloalkenyl , _C3-C8 halocycloalkenyl, _C3-C8 cycloalkoxy, C3-C6

Cycloalkenyloxy, hydroxyimino-Ci-C ₈ alkyl, Ci-Cβ alkylene, oxy-C ₂ -C ₄ - alkylene, oxy-Ci-C ₄ alkyleneoxy, C ₈ -Alkoximino-C ₈ alkyl, C ₂ -C ₈ -AIk- enyloximino-Ci-C ₈ alkyl, C ₂ -C ₈ -Alkinyloximino-Ci-C ₈ alkyl, S (= O) _n A ^1, C (= O) A ^2, C (= S) A ² , NR ⁵ R ⁶ , NR ⁵ -C = OR ⁶ , C (= N-OR ⁷ ) (NR ⁸ R ⁹ ), C (= N-NR ¹⁰ R ¹¹ ) (NR ¹² R ¹³ ) or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from Group oxygen, nitrogen and sulfur; where n, A ¹ , A ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ^{13 are}

nθ, 1 or 2;

A ^{1 is} hydrogen, hydroxy, C ¹ -C 8 -alkyl, C ¹ -C 5 -haloalkyl, amino,

Ci-Cs-alkylamino or di-Ci-Cs-alkylamino,

A ² A ¹ wherein one of said groups or NR ⁵ R ^6, C 2 -C 8 alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl, C ₃ -C ₈ haloalkynyl, d-

Cs-alkoxy, Ci-Cs-haloalkoxy, C2-C8-alkenyloxy, C ₂ -C ₈ - haloalkenyloxy, C ₂ -C 8 alkynyloxy, C ₃ -C ₈ haloalkynyloxy, Cs-Cs-cycloalkyl, C ₃ -C ₈ -Halocycloalkyl, C ₃ -C ₈ -cycloalkoxy, Cs-Cs-halocycloalkoxy;

R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₅ -haloalkyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Cs-Cs-cycloalkyl, _{C3-C8-halocycloalkyl,} C3-Cs-cycloalkenyl or C3-C mean ₈ halocycloalkenyl .

R ⁸ and R ⁹ , R ¹⁰ and R ¹¹ and / or R ¹² and R ¹³ may also together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which is unsubstituted or is substituted with one, two, three or four identical or different substituents R ^a ;

where L can carry one, two, three or four identical or different groups R ^L ;

R ^{L is} halogen, cyano, C ₁ -C ₈ -alkoxy, C ₂ -C 8 -alkenyloxy, C ₂ -C 5 -alkenyloxy, C ₁ -C ₈ -cycloalkyl, C ₁ -C ₈ -cycloalkenyl, C ₁ -C ₈ -cycloalkyloxy, C ₃ -C ₈ - cycloalkenyloxy, Ci-Cs-alkoximino, C ₂ -C ₈ -Alkenyloxyimino, C ₂ -C ₈ -Alkin- yloxyimino, Ci-C ₈ -Alkoximino-C ₈ alkyl, C ₂ -C ₈ -Alkenyloximino Ci- -C ₈ alkyl, C ₂ -C ₈ alkynyloximino-Ci-C ₈ alkyl;

-Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, Cs-Cio-cycloalkyl, C ₃ -C ₀ -cycloalkenyl or an imino group; where these radicals can carry one, two, three or four identical or different groups R ^a and / or two substituents bonded to the same or adjacent atoms or ring atoms for C ₁ -C 6 -alkylene, oxy-C ₂ -C 4 -alkylene or oxy -Ci-C4-alkyleneoxy can stand; Z NR ³ R ⁴ , where R ³ and R ^{4 are}

R ³ Ci-C ₈ alkyl, Ci-Cβ-haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ haloalkenyl, C2-C8-alkynyl, Cs-Cs haloalkynyl, C4-Cio-alkadienyl, C4 -Cio-haloalkadienyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8-alkynyloxy, Cs-Cs-haloalkynyloxy, C3-C8-cycloalkyl, Cs -Cs-halogenocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-halogeno-cycloalkenyl, Cs-Cs-cycloalkoxy, Cs-Cs-halogenocycloalkoxy, Cs -dubi-cycloalkyl, amino, Ci-Cs-alkylamino, di-d C 1 -C 6 -alkylamino, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S;

R ^{4 is} hydrogen, hydroxy or one of the meanings given for R ³ ;

R ³ and R ⁴ may also together with the nitrogen atom to which they are attached form a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two or three further heteroatoms from the group O, N and S as ring members may contain; in which

R ³ and / or R ⁴ or a heterocycle formed from R ³ and R ⁴ may carry one, two, three or four identical or different groups R ^a and / or two substituents bound to adjacent ring atoms for d-

Cβ-alkylene, oxy-C 2 -C 4 -alkylene or oxy-C 1 -C 4 -alkylenoxy;

or an agriculturally acceptable salt thereof; and

at least one active ingredient II selected from groups A) to F):

A) Azoles selected from bitertanol, bromuconazole, cyproconazole, difenocynazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole,

Triadimefon, Triadimenol, Tebuconazole, Tetraconazole, Triticonazole, Prochorazole, Pefurazoate, Imazalil, Triflumizole, Cyazofamide, Benomyl, Carbendazim, Thiabendazole, Fuberidazole, Ethaboxam, Etridiazole, Hymexazole, Azaconazole, Diniconazole-M, Oxpoconazole, Paclobutrazole, Uniconazole, 1- (4-chlorophenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol and imazalil sulfate; B) strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, (2-chloro-5- [1- (3-methylbenzyl-oxyimino) - ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho ( Methyl 2,5-dimethyl-phenyl-oxymethylene) -phenyl) -3-methoxyacrylate, 2- (2- (6- (3-chloro-2-methyl-phenoxy) -5-fluoropyrmidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide and methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclo-propane-carboxymethyl-sulfanyl-methyl) -phenyl) -acrylate;

C) Carboxylic acid amides selected from carboxin, benalaxyl, benodanil, boscalid, fenfuram, fenhexamide, flutolanil, furametpyr, mepronil, metaldaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro - phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-methanesulfonyl-amino-3-methyl-butyramide, N- (2- [4- [3- (4-chloro-phenyl ) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methylbutyramide, 3- (4-

Chloro-phenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylaminopropionic acid methyl ester, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-bromo-biphenyl- 2-yl) amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5 carboxylic acid N- (4'-chloro-3'-fluoro-biphenyl-2-yl) -amide, 3

Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl) phenyl) amide, benalaxyl-M, metalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-

(1,1,1-trimethyl-indan-4-yl) -nicotinamide, N- (2- (1,3-dimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4 carboxamide, N- (4'-chloro-3 ', 5-difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- Chloro-3 ', 5-difluoro-biphenyl-2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (cis-2-bicyclopropyl-2-yl-phenyl) -3 difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (trans-2-bicyclopropyl) -yl-phenoxy-S-difluoromethyl-1-methyl-1H-pyrazole-carboxamide, fluopyram, N-butyl (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide, penthiopyrad and 1-

Methyl-pyrazol-4-ylcarboxanilide of the formula III

wherein the substituents have the following meanings:

X is hydrogen or fluorine;

R ^{1 is} C ¹ -C ₄ -alkyl or C ¹ -C ₄ -haloalkyl; R ^{2 is} hydrogen or halogen;

R ^3, R ⁴ and R ⁵ are independently hydrogen, cyano, nitro, halogen, _{Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy,} Ci-C ₄ - haloalkoxy, _Ci-C4- Alkylthio or C 1 -C ₄ haloalkyl;

Heterocyclic compounds selected from fluazinam, pyrifenox,

Bupirimat, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforin, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozoline, famoxadone, fenamidone, octhilinone, probenazole, 5 Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, anilazine, diclomethine , Pyroquilone, proquinazide, tricyclazole, the compound of formula IV (2-butoxy-6-iodo-3-propyl-chromen-4-one)

Acibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1 - sulphonic acid

2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-di-carbonitrile, N- (1- (5-bromo-3-chloropyridine) 2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichloro-nicotinamide, diflumetorim, nitrapyrin, Dodemorph acetate, fluoroimide, blasticidin-S, quinomethionate, debacarb, difenzoquat, difenzoate methyl sulfate, oxolinic acid, piperine and an azolopyrimidin-7-ylamine of the formula VI

where the substituents have the following meanings:

E ^{1 is} C ₃ -Ci2 alkyl, C ₂ -C ₂ -alkenyl, C ₅ -C ₂ -alkoxyalkyl, C ₃ -C ₆ cycloalkyl,

Phenyl or phenyl-C 1 -C 4 -alkyl; E ² Ci-Ci2-alkyl, _C2-Ci2 alkenyl, Ci-C ₄ haloalkyl or -C ₄ alkoxy- -AI

C 1 -C ₄ -alkyl; wherein the aliphatic groups in E ¹ and / or E ^{2 in} turn carry one, two, three or four identical or different groups R ^a , which are independently selected from: R ^a halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl , C1-C10-

Haloalkyl, C ₃ -C ₈ cycloalkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, -C ₆ - alkoxy, Ci-Ce-alkylthio, alkoxy-CRCE CRCE-alkyl, and NR ^A R ^B; in which

R ^A , R ^B independently of one another are hydrogen or C 1 -C 6 -alkyl; where the cyclic groups in E ¹ and / or R ^a may carry one, two, three identical or different groups R ^b , which are selected independently of one another from: R ^{b is} halogen, cyano, hydroxyl, mercapto, nitro, NR ^A R ^B , Ci-Cio-alkyl,

C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl and C ₁ -C ₆ -alkoxy; E ^{3 is} hydrogen, halogen, cyano, NR ^A R ^B , hydroxyl, mercapto, CrC ₆ -

Alkyl, CRCE haloalkyl, C ₃ -C ₈ cycloalkyl, -C ₆ alkoxy, Ci-Ce-alkylthio, C ₃ -Cs -alkoxy-CyClOaI, C ₃ -C 8 cycloalkylthio, carboxyl, formyl, CrCio-alkylcarbonyl, C ₁ -C 10 -alkoxycarbonyl, C ₂ -C 10 -alkenyloxycarbonyl, C ₂ -C 10 -alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio and C ₁ -C ₆ -alkyl-S (O) _m -; m is 0, 1 or 2;

A is CH or N;

Carbamates selected from Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavalicarb, Propamocarb, N- (1- (1 - (4-cyanophenyl) ethanesulfonyl-but - 2-yl) carbamic acid (4-fluorophenyl) ester, 3- (4-chloro-phenyl-3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino-propanoic acid methyl ester of the formula VII

and carbamato oxime ethers of the formula VIII j

Z is N or CH;

Metasulfocarb and propamocarb hydrochloride;

F) Other fungicides selected from guanidine, dodin, iminoctadine, iminoctadin triacetate, guazatine, guazatine acetate, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithionon, isoprothiolane, organometallic compounds : Fentin Salts, Organophosphorus Compounds: Edifenphos, Iprobenfos, Fosetyl, Fosetyl Aluminum, Phosphoric Acid and Their Salts, Pyrazophos, Tolclofosmethyl, Organochlorine Compounds: Chlorothalonil, Dichlofluanid, Flusulfamide, Hexachlorobenzene, Phthalide, Pencycuron, Quintozene, Thiophanate

Methyl, tolylfluanid, Inorganic agents: Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur, others: cyflufenamide, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine, iminoctadine tris (albesilat), casagicycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its

Salts, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide, diclorane, nitrothal-isopropyl, tecnazene, biphenyl, bronopol, diphenylamine, mildiomycin, oxine-copper, prohexadione Calcium, N- (cyclopropylmethoxyimino- (6-difluoro-methoxy-2,3-difluoro-phenyl) -methyl) -2-phenyl-acetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -

2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N -methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine and N' - (5-difluoromethyl-2-methyl- 4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine;

in a synergistically effective amount.

In addition, the invention relates to a method for controlling harmful fungi with a composition of at least one compound I and at least one of the active compounds II, the use of the compound (s) I with active ingredient (s) II for the preparation of such compositions and agents and seeds containing them Contain compositions. With a view to reducing the application rates and broadening the spectrum of action of the compounds I and the active compounds II, the object of the present invention was to provide possibilities whereby an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied active substances, can be achieved.

Accordingly, the compositions of the compounds I and the active compounds II defined above were found. It has also been found that it is possible to combat harmful fungi more effectively in the simultaneous, joint or separate application of at least one compound I and of at least one of the active compounds II or the compound (s) I and at least one of the active compounds II with the individual compounds alone (synergistic compositions).

The compounds of the formula I used as component 1), their preparation and their action against harmful fungi are generally known from the literature (WO 02/48151, WO 04/000844, WO 05/000851, WO 05/056555, WO 05/056556, WO 05/056557, WO 05/056558, WO 05/056559, WO 05/082907). These compounds are known for controlling harmful fungi.

The active compounds II mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are mostly commercially available:

Benalaxyl, methyl N- (phenylacetyl) -N- (2,6-xylyl) -DL-alaninate (DE 29 03 612); Metalaxyl, methyl N- (methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (GB 15 00 581);

Ofurace, (RS) -α- (2-chloro-N-2,6-xylylacetamido) -γ-butyrolactone [CAS RN 58810-48-3];

Oxadixyl, N- (2,6-dimethylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide (GB

20 58 059);

Aldimorph, "4-alkyl-2,5 (or 2,6) -dimethylmorpholine" containing 65-75% 2,6-dimethylmorpholine and 25-35% 2,5-dimethylmorpholine containing more than 85% 4- dodecyl

2,5 (or 2,6) -dimethylmorpholine, wherein "alkyl" also includes octyl, decyl, tetradecyl and hexadecyl having a cis / trans ratio of 1: 1 [CAS RN 91315-15-0];

Dodin, 1-dodecylguanidinium acetate (Plant Dis. Rep. 41, p.1029 (1957));

Dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 1198125); Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE-A 27 52 096);

Fenpropidin, (RS) -I - [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (DE-A 27 52 096);

Guazatine, composition of the reaction products obtained from the amidation of technical lminodi (octamethylene) diamine containing various guanidines and polyamines [CAS RN 108173-90-6];

Iminoctadin, 1, 1 '-lminodi (octamethylene) diguanidine Congr. Plant Pathol., 1, p. 27

(1968); Spiroxamine, (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842);

Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 1 164 152);

Pyrimethanil, 4,6-dimethylpyrimidin-2-yl-phenylamine (DD-A 151 404);

Mepanipyrim, (4-methyl-6-prop-1-ynyl-pymidin-2-yl) -phenylamine (EP-A 224 339); Cyprodinil, (4-cyclopropyl-6-methyl-pyridin-2-yl) -phenylamine (EP-A 310550);

Cycloheximide, 4 - {(2R) -2 - [(1S, 3S, 5S) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl} piperidine-2,6-dione [CAS RN 66- 81-9];

Griseofulvin, 7-chloro-2 ', 4,6-trimethoxy-6'-methylspiro [benzofuran-2 (3H), 1'-cyclohex-2'-ene] -3,4'-dione [CAS RN 126-07 -8th]; Kasugamycin, 3-O- [2-amino-4- [carboxymiminomethyl) amino] -2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl] -D-chiro-inositol [CAS RN 6980-18- 3];

Natamycin, (8E, 14E, 16E, 18E, 20E) - (1R, 3S, 5R, 7R, 12R, 22R, 24S, 25R, 26S) -22- (3-amino-3,6-dideoxy- β-D-mannopyranosyloxy) -1,3,26-trihydroxy-12-methyl-10-oxo-6,1 1, 28-trioxatricyclo [22.3.1.0 ⁵⁷ ] octacosa-8,14,16,18,20-pentaenes 25-carboxylic acid [CAS RN 7681-93-8];

Polyoxyn, 5- (2-amino-5-O-carbamoyl-2-deoxy-R ^c -xylonamido) -1- (5-carboxy-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1 yl) -1, 5-dideoxy-.beta.-D-allofuranuronic acid [CAS RN

22976-86-9];

Streptomycin, 1,1 '- {1-R ^C - (1,3,5 / 2,4,6) -4- [5-deoxy-2-O- (2-deoxy-2-methylamino-α-R ^c - glucopyranosyl) -3-C-formyl-α-R ^c -lyxofuranosyloxy] -2,5,6-trihydroxycyclohex-1, 3-ylene} diguanidine (J. Am. Chem. Soc., 69: 1234 (1947 ));

Bitertanol, β - ([1, 1'-biphenyl] -4-yloxy) -α- (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol

(DE-A 23 24 020);

Bromuconazole, 1 - [[4-bromo-2- (2,4-dichlorophenyl) tetrahydro-2-furanyl] methyl] -1H-1, 2,4-triazole (Proc. 1990 Br. Crop. Prot. Conf. -Pests Dis., Vol. 1, p. 459);

Cyproconazole, 2- (4-chlorophenyl) -3-cyclopropyl-1 - [1, 2,4] triazole-1-yl-butan-2-ol

(US 4,664,696);

Difenoconazole, 1 - {2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl- [1,3-dioxolan-2-ylmethyl} -1 H- [1,2,4] triazole ( GB-A 2 098 607); Diniconazole, (βE) -β - [(2,4-dichlorophenyl) methylene] -α- (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol 8, p. 575);

Enilconazole (imazalil), 1- [2- (2,4-dichlorophenyl) -2- (2-propenyloxy) ethyl] -1H-imidazole

(Fruits 28, p. 545, 1973);

Epoxiconazole, (2RS, 3SR) -1 - [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1H-1,2,4-triazole (EP-A 196 038);

Fenbuconazole, α- [2- (4-chlorophenyl) ethyl] -α-phenyl-1H-1, 2,4-triazole-1-propanenitrile

(Proc., 1988, Br. Crop Prot. Conf.-Pests Dis., Vol. 1, p.

Fluquinconazole, 3- (2,4-dichlorophenyl) -6-fluoro-2- [1,2,4] triazole-1-yl-3H-quinazolin-4-one

(Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 41 1 (1992)); Flusilazole, 1 - {[bis (4-fluorophenyl) methylsilanyl] methyl} -1 H- [1,2,4] triazole (Proc. Br. Crop

Prot. Conf.-Pests Dis., Vol. 1, p. 413 (1984));

Flutriafol, α- (2-fluorophenyl) -α- (4-fluorophenyl) -1H-1, 2,4-triazole-1-ethanol (EP-A 15 756); Hexaconazole, 2- (2,4-dichlorophenyl) -1- [1,2,4] triazol-1-yl-hexan-2-ol CAS RN

79983-71-4);

Ipconazole, 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778); Metconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1 - [1, 2,4] triazole-1-ylmethylcyclopentanol

(GB 857,383);

Myclobutanil, 2- (4-chlorophenyl) -2- [1,2,4] triazol-1-ylmethylpentanenitrile CAS RN 88671-

89-0);

Penconazole, 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12th Edition 2000, p. 712);

Propiconazole, 1 - [[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl] -1H-1, 2,4-triazole (BE 835,579);

Prochlorazole, imidazole-1-carboxylic acid-propyl- [2- (2,4,6-trichlorophenoxy) -ethyl] -amide

(US 3,991,071); Prothioconazole, 2- [2- (1-Chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048) ;

Simeconazole, α- (4-fluorophenyl) -α - [(trimethylsilyl) methyl] -1H-1, 2,4-triazole-1-ethanol

[CAS RN 149508-90-7];

Tebuconazole, 1- (4-chlorophenyl) -4,4-dimethyl-3- [1,2,4] triazole-1-ylmethylpentan-3-ol (EP-A 40 345);

Tetraconazole, 1- [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1, 2,4-triazole (EP-A 234 242);

Triadimefon, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1, 2,4-triazol-1-yl) -2-butanone (BE

793 867); Triadimenol, β- (4-chlorophenoxy) -α- (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (DE-A

23 24 010);

Triflumizole, (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/1 19 462);

Triticonazole, (5E) -5 - [(4-chlorophenyl) methylene] -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (FR 26 41 277);

Iprodione, 3- (3,5-dichlorophenyl) -2,4-dioxo-imidazolidine-1-carboxylic acid isopropylamide (GB

13 12 536);

Myclozoline, (RS) -3- (3,5-dichlorophenyl) -5-methoxymethyl-5-methyl-1,3-oxazolidine-2,4-dione [CAS RN 54864-61-8]; Procymidone, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (US Pat

3,903,090);

Vinclozoline, 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-oxazolidine-2,4-dione (DE-A

22 07 576);

Ferbam, iron (3+) dimethyldithiocarbamate (US 1,972,961); Nabam, disodium ethylenebis (dithiocarbamate) (US 2,317,765);

Maneb, manganese ethylene bis (dithiocarbamate) (US 2,504,404); Mancozeb, manganese ethylene bis (dithiocarbamate) polymer complex zinc salt (GB

996 264);

Metam, methyldithiocarbamic acid (US 2,791,605);

Metiram, zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400); Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);

Polycarbamate, bis (dimethylcarbamodithioato-κS, κS ') [μ - [[1,2-ethanediylbis [carbamoedithioato-κS, κS']] (2 -)]] di [zinc] [CAS RN 64440-88-6 ];

Thiram, bis (dimethylthiocarbamoyl) disulfide (DE-A 642 532);

Ziram, dimethyldithiocarbamate [CAS RN 137-30-4]; Zineb, zinc ethylenebis (dithiocarbamate) (US 2,457,674);

Anilazine, 4,6-dichloro-N- (2-chlorophenyl) -1, 3,5-triazin-2-amine (US 2,720,480);

Benomyl, 2-acetylaminobenzimidazole-1-carboxylic acid butylamide (US 3,631,176);

Boscalid, 2-chloro-N- (4'-chlorobiphenyl-2-yl) nicotinamide (EP-A 545 099);

Carbendazim, (1 H-benzimidazol-2-yl) -carbamic acid methyl ester (US 3,657,443); Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3,249,499);

Oxycarboxine, 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide-4,4-dioxide (US Pat

3,399,214);

Cyazofamide, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamid CAS RN 120116-88-3]; Dazomet, 3,5-dimethyl-1,3,5-thiadiazinan-2-thione (Bull Soc Soc. Chim. Fr. Vol. 15, p.891

(1897));

Diflufenzopyr, 2- {1- [4- (3,5-difluorophenyl) semicarbazono] ethyl} nicotinic acid [CAS RN

109293-97-2];

Dithianone, 5,10-dioxo-5,10-dihydronaphtho [2,3-b] [1,4] dithiine-2,3-dicarbonitrile (GB 857,383);

Famoxadone, (RS) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione

[CAS RN 131807-57-3];

Fenamidone, (S) -1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one [CAS RN

161326-34-7]; Fenarimol, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidinemethanol (GB 12 18 623);

Fuberidazole, 2- (2-furanyl) -1H-benzimidazole (DE-A 12 09 799);

Flutolanil, α, α, α-trifluoro-3'-isopropoxy-o-toluanilide (JP 1104514);

Furametpyr, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ]; Isoprothiolane, diisopropyl-1,3-dithiolan-2-ylidene malonate (Proc. Insectic, Fungic, Conf.

Vol. 2, p. 715 (1975));

Mepronil, 3'-isopropoxy-o-toluanilide (US 3,937,840);

Nuarimol, α- (2-chlorophenyl) -α- (4-fluorophenyl) -5-pyrimidinemethanol (GB 12 18 623);

Fluopicolide (picobenzamide), 2,6-dichloro-N- (3-chloro-5-trifluoromethylpyridin-2-ylmethyl) benzamide (WO 99/42447);

Probenazole, 3-allyloxy-1,2-benzothiazole-1,1-dioxide (Agric. Biol. Chem. 37, p

(1973); Proquinazide, 6-iodo-2-propoxy-3-propylquinazolin-4 (3H) -one (WO 97/48684);

Pyrifenox, 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone (EZ) -O-methyloxime (EP 49 854);

Pyroquilone, 1, 2,5,6-tetrahydropyrrolo [3,2,1-ij] quinolin-4-one (GB 139 43 373);

Quinoxyfen, 5,7-dichloro-4- (4-fluorophenoxy) quinoline (US 5,240,940); Silthiofam, N-allyl-4,5-dimethyl-2- (trimethylsilyl) thiophene-3-carboxamide [CAS RN

175217-20-6];

Thiabendazole, 2- (1, 3-thiazol-4-yl) benzimidazole (US 3,017,415);

Thifluzamide, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxanilide [CAS RN 130000-40-7]; Thiophanate-methyl, 1, 2-phenylenebis (iminocarbonothioyl) bis (dimethylcarbamate) (DE-A

19 30 540);

Tiadinil, 3'-chloro-4,4'-dimethyl-1,2,3-thiadiazole-5-carboxanilide [CAS RN 223580-51-6];

Tricyclazole, 5-methyl-1,2,4-triazolo [3,4-b] [1,3] benzothiazole [CAS RN 41814-78-2];

Triforin, N, N '- {piperazine-1, 4-diylbis [(trichloromethyl) methylene] diformamide (DE-A 19 01 421);

5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (WO 98/46607);

Bordeaux broth, composition of CuSO ₄ × 3Cu (OH) ₂ × 3CaSO ₄ [CAS RN 8011-

63-0]; Copper acetate, Cu (OCOCHs) ₂ [CAS RN 8011-63-0];

Copper oxychloride, Cu ₂ Cl (OH) ₃ [CAS RN 1332-40-7];

Basic copper sulfate, CuSO ₄ [CAS RN 1344-73-6];

Binapacryl, (RS) -2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate [CAS RN 485-31-4];

Dinocap, composition of 2,6-dinitro-4-octylphenyl crotonate and 2,4-dinitro-6-octylphenyl crotonate, where "octyl" is a composition of 1-methylheptyl, 1-

Ethylhexyl and 1-propylpentyl is (US 2,526,660);

Dinobutone, (RS) -2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21-7];

Nitrothal isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic. Fungic. Conf.

Vol. 2, p. 673 (1973)); Fenpiclonil, 4- (2,3-dichlorophenyl) -1H-pyrrole-3-carbonitrile (Proc., 1988 Br. Crop Prot.

Conf. - Pests Dis., Vol. 1, p. 65);

Fludioxonil, 4- (2,2-difluorobenzo [1,3] dioxol-4-yl) -1H-pyrrole-3-carbonitrile (The Pesticide

Manual, Ed .: The British Crop Protection Council, 10th Edition 1995, p. 482);

Acibenzolar-S-methyl, methyl 1, 2,3-benzothiadiazole-7-carbothioate [CAS RN 135158-54-2];

Flubenthiavalicarb (benthiavalicarb), {(S) -1 - [(1 R) -1- (6-fluorobenzothiazol-2-yl) ethylcarbamoyl] -2-methylpropyl} -carbamic acid isopropyl ester (JP-A 09/323 984);

Carpropamide, 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropane carboxamide [CAS RN 104030-54-8]; Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);

Cyflufenamide, (Z) -N- [α-cyclopropylmethoxyimino) -2,3-difluoro-6- (trifluoromethyl) benzyl] -

2-phenylacetamide (WO 96/19442); Cymoxanil, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (US 3,957,847);

Diclomethine, 6- (3,5-dichlorophenyl-p-tolyl) pyridazine-3 (2H) -one (US 4,052,395)

Diclocymet, (RS) -2-cyano-N - [(R) -1- (2,4-dichlorophenyl) ethyl] -3,3-dimethylbutyramide

[CAS RN 139920-32-4]; Diethofencarb, isopropyl 3,4-diethoxycarbanilate (EP-A 78 663);

Edifenphos, O-ethyl S, S-diphenyl phosphorodithioate (DE-A 14 93 736)

Ethaboxam, N-cyano-2-thienylmethyl) -4-ethyl-2- (ethylamino) -5-thiazolecarboxamide (EP-

A 639 574);

Fenhexamid, N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, Vol. 2, p. 327);

Fentin acetate, triphenyltin (US 3,499,086);

Fenoxanil, N- (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propanamide (EP-A

262 393);

Ferric zone, (Z) -2'-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7];

Fluazinam, 3-chloro-N- [3-chloro-2,6-dinitro-4- (trifluoromethyl) phenyl] -5- (trifluoromethyl) -2-pyridinamine (The Pesticide Manual, Ed .: The British Crop Protection Council, 10 th edition 1995, p. 474);

Fosetyl, Fosetyl Aluminum, Ethyl Phosphonate (FR 22 54 276); Iprovalicarb, [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl) -propyl] -carbamic acid isopropyl ester (EP-A 472 996);

Hexachlorobenzene C.R. Seances Acad. Agric. Fr., Vol. 31, p. 24 (1945);

Mandipropamide, (RS) -2- (4-chlorophenyl) -N- [3-methoxy-4- (prop-2-ynyloxy) phenethyl] -2-

(prop-2-ynyloxy) acetamide (WO 03/042166); Metrafenone, 3'-Bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone

(US 5,945,567);

Pencycuron, 1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (DE-A 27 32 257);

Penthiopyrad, (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268); Propamocarb, 3- (dimethylamino) propylcarbaminsäureisopropylester (DE-A 15 67 169);

Phthalide (DE-A 16 43 347);

Toloclofos-methyl, O-2,6-dichloro-p-tolyl O, O-dimethyl phosphorothioate (GB 14 67 561);

Quintoene, pentachloronitrobenzene (DE-A 682 048);

Zoxamide, (RS) -3,5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -p-toluamide [CAS RN 156052-68-5];

Captafol, N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1,2-dicarboximide (Phytopatholgy 52, p. 754 (1962));

Captan, N- (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide (US 2,553,770);

Dichlofluanid, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfamide (DE-A 1 1 93 498);

Folpet, N- (trichloromethylthio) phthalimide (US 2,553,770); Tolylfluanid, N-dichlorofluoromethylthio-N \ N'-dimethyl-Np-tolylsulfamide (DE-A

1 1 93 498);

Dimethomorph, 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-yl-propenone

(EP-A 120 321); Flumetover, 2- (3,4-dimethoxyphenyl) -N-ethyl-α, α, α-trifluoro-N-methyl-p-toluamide

[AGROW No. 243, 22 (1995)];

Flumorph, 3- (4-fluorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-yl-propenone (EP-A

860 438);

4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-trifluoromethyl-biphenyl -2-yl) -amide,

4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-chloro-3'-fluoro-biphenyl-2-yl) -amide

(WO 03/66610);

3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide and 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide (WO 03/70705);

3,4-dichloro-isothiazole-5-carboxylic acid N- (2-cyanophenyl) -amide (WO 99/24413);

N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyramide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methylbutyramide (WO 04/49804); 3- [5- (4-Chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine (EP-A 10 35 122);

2-butoxy-6-iodo-3-propyl-chromen-4-one (WO 03/14103);

3- (3-Bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide

(EP-A 10 31 571);

(2-Chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] benzyl) -carbamic acid methyl ester (EP-A 12 01 648);

Methyl 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methylbutyrylamino) propionate (EP-A 10 28 125);

Azoxystrobin, 2- {2- [6- (2-Cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl} -3-methoxy-acrylic acid methyl ester (EP-A 382 375) ;

Dimoxystrobin, (E) -2- (methoxyimino) -N-methyl-2- [α- (2,5-xylyloxy) -o-tolyl] -acetamide (EP-

A 477 631);

Fluoxastrobin, (E) - {2- [6- (2-chlorophenoxy) -5-fluoropyrimidin-4-yloxy] phenyl} (5,6-dihydroxy)

1, 4,2-dioxazin-3-yl) methanone O-methyloxime (WO 97/27189); Kresoxim-methyl, (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetic acid methyl ester (EP-A

253 213);

Metominostrobin, (E) -2- (methoxyimino) -N-methyl-2- (2-phenoxyphenyl) acetamide (EP-A

398 692);

Orysastrobin, (2E) -2- (methoxyimino) -2- {2 - [(3E, 5E, 6E) -5- (methoxyimino) -4,6-dimethyl-2,8-dioxa-3,7-diazanona- 3,6-dien-1-yl] phenyl} -N-methylacetamide (WO 97/15552);

Picoxystrobin, 3-methoxy-2- [2- (6-trifluoromethyl-pyridin-2-yloxymethyl) -phenyl] -acrylic acid methyl ester (EP-A 278 595); Pyraclostrobin, N- {2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl} (N-methoxy) carbamic acid methyl ester (WO 96/01256);

Trifloxystrobin, (E) -methoxyimino-{(E) -α- [1- (α, α, α-trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl} -acetic acid methyl ester (EP-A 460 575); 2- [ortho- (2,5-dimethylphenyl-oxymethylene) phenyl] -3-methoxy-methyl acrylate

(EP-A 226 917);

5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (WO 98/46608);

3,4-dichloro-N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide (WO 99/24413); Compounds of the formula III (WO 04/049804);

N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyramide and N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methylbutyramide (WO 03/66609);

2-butoxy-6-iodo-3-propyl-chromen-4-one (WO 03/14103); 3- (3-Bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide

(WO 03/053145);

Methyl 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methylbutyrylamino) propanoate (EP-A 1028125);

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl-phenyl) amide (WO 03/074491, WO 2006/01586).

The 1-methyl-pyrazol-4-ylcarboxanilide of the formula III are known from the literature (see, for example, EP-A 545 099, EP-A 589 301, WO 99/09013, WO 2003/70705 and WO 2006/087343), and can produced by the methods described therein.

The azolopyrimidin-7-ylamines of the formula VI, their preparation and their action against harmful fungi are generally known from the literature (EP-A 71 792, EP-A 141 317, WO 03/009687, WO 05/087771, WO 05/087772 WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).

Depending on the substitution pattern, the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures. The invention relates to both fungicidal compositions containing the pure enantiomers or diastereomers or rotamers and mixtures thereof. In particular, within the scope of the present invention are included the (R) and (S) isomers and the racemates of compounds of formula I having chiral centers. Suitable compounds of formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof. The compounds I used in the compositions according to the invention can be present in various crystal modifications, such compositions also being the subject of the present invention. According to the present invention, suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the pesticidal action of the compounds used according to the invention.

Thus come as cations in particular the ions of the alkali metals, preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci-C4 ) -Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci -C4) -alkylsulfoxonium, into consideration.

Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (C 1 -C 4) -alkanoic acids, preferably formate , Acetate, propionate and butyrate. They can be formed by reaction of the compounds I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

In the definitions of the variables given in formula I, collective terms are used which are generally representative of the respective substituents or the

Substituententeile stand in composite groups. The meaning (C _n -C m) indicates the particular possible number of carbon atoms in the respective substituent or substituent part:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl and the alkyl moieties of composite groups such as alkylamino: saturated, straight-chain or branched hydrocarbon radicals having preferably 1 to 2, 4, 6, 8 or 10 carbon atoms, for example Ci-Cβ-alkyl such as methyl, ethyl, propyl, 1-methylethyl , Butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1 -Dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl , 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2 methyl propyl; Haloalkyl: Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above. In one embodiment, the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo. In a further embodiment, the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred. Particular preference is given to (C 1 -C 4) -haloalkyl, more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;

Hydroxyalkyl: Alkyl as mentioned above, wherein one or more hydrogen atoms are replaced by hydroxy (OH) groups.

Alkenyl and the alkenyl moieties in assembled groups, such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals preferably having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, double bonds in any position. Examples of suitable alkenyl groups are C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl 1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl 2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4- Methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl 3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-bute nyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1 butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2- butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1 Ethyl 3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl 2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; Haloalkenyl: alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Alkadienyl: unsaturated, straight-chain or branched hydrocarbon radicals having preferably 4 to 6, 4 to 8 or 4 to 10 carbon atoms and two double bonds in any position;

Alkynyl and the alkynyl moieties in compounded groups: straight-chain or branched hydrocarbon groups having preferably 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, triple bonds in any position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-1-butynyl, 1-ethyl-2- butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Haloalkynyl: alkynyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Cycloalkyl and the cycloalkyl moieties in combined groups: mono- or bicyclic, preferably monocyclic, saturated hydrocarbon groups having in particular 3 to 6, 3 to 8, 3 to 10 or 3 to 12 carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

Halogencycloalkyl: cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;

Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 12, 3 to 10, 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, Cyclohexene-3-yl, cyclohexene-4-yl and the like;

Halocycloalkenyl: cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine; Alkoxy: for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms. Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3 Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

Haloalkoxy: alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine. Examples of preferred haloalkoxy radicals are OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCHCl ₂ , OCCl ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxy, 1- (CH ₂ Cl) -2- chloroethoxy, 1- (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; and 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chloro-hexoxy, 6-bromohexoxy, 6-iodo-hexoxy or dodecafluorohexoxy;

Alkenyloxy: Alkenyl as defined above, which is bonded via an oxygen atom. Preferred are (C ₂ -C 8) alkenyloxy, more preferably (C ₃ -C 6) alkenyloxy;

Alkylene: divalent linear chains of CH ₂ groups. Preference is given to (C ₁ -C 6) -alkylene, more preferably (C ₂ -C 4) -alkylene, and furthermore it may be preferred to use (C ₁ -C ₃ ) -alkylene groups. Examples of preferred alkylene radicals are CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ (CHz) ₂ CH ₂ , CH ₂ (CH ₂ ) ₃ CH ₂ and CH ₂ (CH ₂ ) ₄ CH ₂ ;

Oxyalkylene: Alkylene, as defined above, preferably having 2 to 4 CH ₂ groups, wherein a valence is bonded to the skeleton via an oxygen atom. Examples of preferred oxyalkylene radicals are OCH ₂ , OCH ₂ CH ₂ , OCH ₂ CH ₂ CH ₂ and OCH ₂ (CH ₂ ) ₂ CH ₂ ;

Oxyalkylenoxy: Alkylene, as defined above, preferably having 1 to 3 CH ₂ groups, wherein both valences are bonded to the skeleton via an oxygen atom. Examples of preferred oxyalkyleneoxy radicals are OCH ₂ O, OCH ₂ CH ₂ O and OCH ₂ CH ₂ CH ₂ O; Alkylthio: alkyl as defined above attached via an S atom;

Alkylsulfinyl: alkyl as defined above which is bonded through an SO group;

Alkylsulfonyl: alkyl as defined above attached via an S (O) 2 group;

Saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S: In particular, it is a five-, six-, seven-, eight-, nine- or ten-membered heterocycle, preferred a five- or six-membered saturated, partially unsaturated or aromatic heterocycle. The respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen. The heterocycle means in particular:

- 5- or 6-membered saturated or partially unsaturated heterocyclyl containing one, two or three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, wherein the heterocyclyl be attached via C or N. can;

5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom which may be attached via C or N; or

6-membered heteroaryl containing one, two, three or four, preferably one, two or three, nitrogen atoms which may be attached via C or N;

5- or 6-membered saturated or partially unsaturated heterocyclyl containing one, two or three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, wherein the heterocyclyl via C or N, if present, attached for example, 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, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2,4-thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiazolidin-2-yl, 1, 3,4-triazolidin-2-yl, 2, 3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2 yl, 2,4-dihydrofur-3-yl, 2,3-dihydro-thien-2-yl, 2,3-dihydro-thien-3-yl, 2,4-dihydro-thien-2-yl, 2,4-dihydro-3-yl yl, 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-iso thiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-i-yl, 2, 3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3, 4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazole-4 yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazole 5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3 Dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3,5- Hexahydro-triazin-2-yl and 1, 2 , 4-hexahydrotriazine-3-yl;

5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3 - pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazole 3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazole-3 -yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazol-2-yl;

6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, have one to four or may contain one to three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.

Aryl: aromatic hydrocarbon cycles, in particular having 6 to 14, preferably 6 to 10 carbon atoms. Phenyl (C ₆ H ₅ -) are preferred according to the rule and naphthyl (C ₀ H ₇ -).

In the compounds of the formula I, the following meanings of the substituents, in each case alone or in combination, are particularly preferred. According to one embodiment of the invention, R ^{1 is} not hydrogen.

According to a further embodiment of the invention, R ^{1 is} chlorine, bromine, cyano, nitro, C 1 -C ₄ -alkoxycarbonyl, CONH ₂ , CH = NO-C 1 -C ₄ -alkyl or C (NH ₂ ) = NOH.

According to a further embodiment of the invention, R ^{1 is} halogen, cyano, nitro, Ci-Cβ alkyl, _{Ci-C8-haloalkyl, Ci-C8-hydroxyalkyl,} d-Cs-alkoxy-d-Cs-alkyl, C2-C _{8 alkenyloxy-Ci-C8} alkyl, _{C2-C8-alkynyloxy-Ci-C 8} alkyl, C ₃ -C ₈ cycloalkyloxy-Ci-C ₈ - alkyl, Ci-C ₈ -Alkoxyalkyloxy-C ₈ -alkyl, benzyloxy-Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Ci-C ₈ - alkoxy, Ci-C ₈ -Halogenalk- oxy, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl, hydroxyimino-Ci-C ₈ alkyl, C ₈ - alkoxyimino-C ₈ -alkyl or a radical

wherein p is 1, 2, 3, 4 or 5 and # is the point of attachment to the Pyrazolopyrimi- dingerüst; wherein the aliphatic and alicyclic groups may contain one, two, three or four identical or different R ^a .

According to one embodiment of the invention, R ^{1 is} C ¹ -C ₈ -alkoxyimino-C ¹ -C ₈ -alkyl, where the alkyl radical may be substituted by R ^a . In particular, R ¹ stands for C (W ³ ) = NO-C 1 -C ₈ -alkyl, where W ^{3 is} hydrogen or C 1 -C 6 -alkyl and W ^{3 contains} one, two, three or four identical or different groups R ^a can. In a specific embodiment, R ^{1 is} CH = NO-C ¹ -C ⁴ -alkyl.

According to a further embodiment of the invention, R ^{1 is} C (= W ¹ ) NH ₂ , where W ^{1 is} S, O, NH, N-OH or N-OW ² , where W ^{2 is} C ₁ -C ₆ -alkyl or C ₆ -C ₄ -aryl-C 1 -C ₈ -alkyl, wherein W ² may contain one, two, three or four identical or different groups R ^a .

According to yet another embodiment of the invention, R ^{1 is} C (W ³ ) = N (W ⁴ ), where W ^{3 is} hydrogen or C ¹ -C ⁶ -alkyl and W ^{4 is} C ¹ -C ⁶ -alkyl, phenyl or phenylamino, wherein W ³ and / or W ^{4 may} each independently contain one, two, three or four identical or different groups R ^a .

According to a further embodiment of the invention, R ^{1 is} C (= W ¹ ) -NH ₂ , where W ^{1 is} O, NH, N-OH or N-OW ² , where W ^{2 is} C ₁ -C ₆ -alkyl or C ₆ -C 12 -alkyl ₄ -aryl-C 1 -C ₈ -alkyl; or R ¹ is C (W ³ ) = N (W ⁴ ), where W ^{3 is} hydrogen or C ¹ -C 6 -alkyl, W ^{4 is} C 1 -C 6 -alkyl, phenyl or phenylamino; wherein W ² , W ³ and / or W ^{4 may} each independently contain one, two, three or four identical or different groups R ^a as defined herein or preferably defined; According to a further embodiment, R ^{1 is} C (W ³ ) = N (W ⁴ ), wherein W ^{3 is} hydrogen or C ¹ -C ⁴ -alkyl, W ^{4 is} C ¹ -C ⁴ -alkyl and each of the alkyl radicals can be monosubstituted or disubstituted by C 1 -C ₄ -alkoxy, C 1 -C 3 -alkylcarbonyl and / or C 1 -C 3 -alkoxycarbonyl; or W ⁴ is phenyl which may be monosubstituted to trisubstituted by identical or different substituents by C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, halogen, nitro and / or C 1 -C ₄ -haloalkyl having 1 to 5 halogen atoms. According to a further embodiment, W ⁴ here means phenylamino, which may be mono- to trisubstituted by identical or different substituents chosen from _Ci-C4 -alkyl, Ci-C ₄ alkoxy, halogen, nitro and / or Ci-C ₄ haloalkyl having 1 to 5 halogen atoms. According to yet another embodiment, W ^{3 is} hydrogen, methyl or ethyl and W ⁴ is C ₁ -C ₂ -alkyl, where any of the alkyl radicals may be substituted by methoxy, ethoxy, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl. In yet another embodiment, W ^{4 is} phenyl, which may be monosubstituted to trisubstituted by identical or different methyl, ethyl, methoxy, ethoxy, fluoro, chloro, bromo, nitro and / or trifluoromethyl, or W ⁴ is phenylamino, which is simple may be substituted by three or more identical or different by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, nitro and / or trifluoromethyl.

According to yet another embodiment of the invention, R ¹ CW ⁵ (= 0), wherein W ⁵ represents hydrogen, Ci -C ₈ -alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -alkyl kinyl, C ₃ C ₈ -Cycloalkyl, benzyl, wherein W ⁵ may contain one, two, three or four identical or different groups R ^a .

According to a further embodiment of the invention, R ^{1 is} C (W ⁵ ) = O, where W ^{5 is} C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ -C ₆ -cycloalkyl or benzyl, wherein W ⁵ may contain one, two, three or four identical or different groups R ^a as defined herein or preferably defined. In one embodiment, W represents Ci-C6 haloalkyl ^5, C ₂ -C 6 alkenyl, C ₂ -CE kinyl Al, Cs-Cβ cycloalkyl or benzyl, in particular C ₄ d- haloalkyl, C3-Cs-alkenyl, C3 C5-Al kinyl, cyclopropyl, cyclopentyl, cyclohexyl or benzyl, preferably CF3, CCI3, AIIyI, propargyl, cyclopropyl or benzyl.

According to yet another embodiment of the invention, R ^{1 is} CONW ⁶ W ⁷ , CONW ⁷ -N (W ⁷ ) ₂ , CO-NW ⁷ -OW ⁷ , COOW ⁸ , C (S) OW ⁷ , C (O) SW ⁷ , C (S) SW ⁷ , SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁷ , SON (W ⁷ ) ₂ , SO ₂ N (W ⁷ ) ₂ , P (O) (OW ⁷ ) ₂ , NW ⁷ OW ^7, B (OW ⁷⁾ _2, - (CW ⁷ ₂₎ o- ₆ ⁷ -NW ₂ or - (CW ₂ ⁷⁾ ₀ - _6. -NW -NW ^{7 7} _2; where W ⁶ , W ⁷ , W ^{8 are} each independently:

W ⁶ Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, C ₆ -Ci4-aryl, C ₆ -C ₄ -Aryl-C 1 -C ₈ -alkyl;

W ^{7 is} hydrogen or one of the radicals mentioned at W ⁶ ; two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ may also together form a saturated or partially unsaturated radical. form saturated cycle having 3, 4, 5 or 6 carbon atoms, which may contain 1 or 2 further heteroatoms selected from nitrogen, sulfur and oxygen;

W ⁸ is hydrogen, a cation, Ci -C ₈ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkyl kinyl, C ₃ -C ₈ cycloalkyl, Cs-Cs-cycloalkenyl, or C ₆ - Ci4-aryl-Ci-C ₈ alkyl;

wherein W ⁶ , W ⁷ , W ⁸ or a cycle formed from W ⁷ or W ⁷ and W ⁶ may each independently contain one, two, three or four identical or different groups R ^a .

According to a further embodiment of the invention, R ^{1 is} CONW ⁶ W ⁷ ,

CONW ⁷ -N (W ⁷ ) ₂ , CO-NW ⁷ -OW ⁷ , COOW ⁸ , C (S) OW ⁷ , C (O) SW ⁷ , C (S) SW ⁷ , # -SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁷ , SON (W ⁷ ) ₂ , SO ₂ N (W ⁷ ) ₂ , P (O) (OW ⁷ ) ₂ , NW ⁷ OW ⁷ , B (OW ⁷ ) ₂ , (CW ⁷ ₂ ) ₀ - ₆ - NW ⁷ ₂ or (CW ⁷ ₂ ) ₀ - ₆ -NW ⁷ -NW ⁷ ₂ ; wherein W ⁶ Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -alkyl kinyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, Ce-Cu-aryl or C ₆ -Ci4- Aryl-C 1 -C ₈ -alkyl, W ^{7 is} hydrogen or one of the radicals mentioned at W ⁶ , two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ together with a saturated or partially unsaturated cycle with 3, 4, 5 or 6 carbon atoms, which may contain 1 or 2 further heteroatoms selected from nitrogen, sulfur and oxygen, O atoms may not be adjacent; and W ⁸ represents hydrogen, a cation, Ci-C ₈ -alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -alkyl kinyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl or C6-Ci4 aryl-Ci-Cs-alkyl. W ⁶ , W ⁷ , W ⁸ may each independently contain one, two, three or four identical or different groups R ^a .

According to a further embodiment of the invention, R ^{1 is} cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C ₁ -C 6 -haloalkyl having one to nine halogen atoms independently selected from fluorine, chlorine and bromine, C ₁ -C ₄ -alkyl, C ₂ C6-alkenyl, C ₂ -C -alkenyl substituted by carboxy, methoxycarbonyl or ethoxycarbonyl, C ₂ -C 6 -alkynyl, preferably C ₂ -C -alkenyl, C ₂ -C -alkenyl substituted by carboxy, methoxycarbonyl or ethoxycarbonyl , preferably C ₂ -C -alkenyl, C ₁ -C 4 -hydroxyalkyl, C ₁ -C 4 -alkoxy-C ₁ -C 4 -alkyl, C ₁ -C 6 -cycloalkyl, thiocarbamoyl, C ₁ -C 4 -alkoxycarbonyl, C ₁ -C 4 -alkylcarbonyl, C 4 -hydroximinoalkyl, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -alkylaminocarbonyl. According to one embodiment of this embodiment, R ^{1 is} cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C 1 -C 4 -haloalkyl having one to nine halogen atoms selected independently from fluorine, chlorine and bromine, C 1 -C 4 -alkyl, Cs-Cβ-cycloalkyl, thiocarbamoyl, C 1 -C ₄ -alkoxycarbonyl, C 1 -C ₄ -alkylcarbonyl, C 1 -C ₄ -hydroximinoalkyl or C 1 -C ₄ -alkoxyimino-C 1 -C ₄ -alkyl.

In another specific embodiment of the invention, R ^{1 is} cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, trifluoromethyl, difluoromethyl, methoxycarbonyl, methylcarbonyl, ethylcarbonyl, hydroximinomethyl, methoximinomethyl, thiocarbamoyl, methyl, ethyl, cyclopropyl, methylthio , Methylsulfinyl, methylsulfonyl, methylaminocar- bonyl, hydroxymethyl, hydroxyeth-1-yl, methoxymethyl, ethoxymethyl or 1-methoxy-ethyl. In particular, R ^{1 is} cyano, fluorine, chlorine, bromine, iodine, formyl, trifluoromethyl, methoxycarbonyl, methylcarbonyl, hydroximinomethyl, methoximinomethyl, thiocarbamoyl, nitro, methyl, ethyl or cyclopropyl. Particular embodiments of R ¹ are in particular cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, methyl, cyclopropyl, thiocarbamoyl and methoximinomethyl.

According to another embodiment of the invention, R ^{1 represents} -CH = CH ₂ , # -C (CH ₃ ) = CH ₂ , # -CH = CH-CH ₃ , # -C (CH ₃ ) = CH-CH ₃ , # - CH = CH-C ₂ H ₅ , # -C (CH ₃ ) = CH-C ₂ H ₅ , # -CH = CH-COOH, # -CH = CH-CO-OCH ₃ , # -CH = CH-CO -OC ₂ H ₅ ,

# -C≡CH, # -C≡C-CH ₃ , # -C≡CC ₂ H ₅ , # -C≡CH-C ₃ H ₇ , # -C≡C-COOH, # -C≡C-COOCH ₃ or # -C≡C-COOC ₂ H ₅ .

#, also in the following, stands for the point of attachment to the pyrazolopyrimidine skeleton.

According to a further embodiment of the invention, R ^{1 represents} -C (W ⁹ ) (W ¹⁰ ) OW ¹¹ , where W ⁹ , W ¹⁰ , W ¹¹ mean:

W ^9, W ^10, W ¹¹ are independently hydrogen, Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} d-Cβ-alkoxyalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -alkyl kinyl, C C ₃ -C ₈ cycloalkyl, benzyl; W ⁹ , W ¹⁰ , W ¹¹ may each independently contain one, two, three or four identical or different groups R ^a , wherein R ^{a is} as herein defined or preferably defined;

W ¹⁰ and OW ¹¹ may also together form a group # -O- (CH ₂ ) _p -O- #, wherein p is 1, 2, 3, 4 or 5 and the alkylene chain contains one, two or three substituents R ^a may be as defined herein, wherein R ^{a is} particularly independently selected from methyl, ethyl, hydroxy, methoxy, ethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl.

Mean According to a further embodiment, W ^9, W ^10, W ¹¹ are independently hydrogen, -C ₄ -alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₂ alkoxy-d- C ₄ alkyl C ₂ -C ₅ alkenyl, C ₂ -C ₅ alkynyl or benzyl; or W ¹⁰ and OW ¹¹ together form # -O-CH ₂ -CH ₂ -O- #, wherein the alkylene chain may contain one or two substituents R ^a , wherein R ^{a is} independently selected from methyl, ethyl, hydroxy, methoxy , Ethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl. In particular, W ⁹ , W ¹⁰ , W ¹¹ independently of one another are hydrogen, methyl, ethyl, propyl, methoxymethyl, methoxyethyl, C ₃ -C ₄ -alkenyl, C ₃ -C ₄ -alkynyl or benzyl; or W ¹⁰ and OW ¹¹ together form # -O-CH ₂ -CH ₂ -O- #, wherein the alkylene chain may contain one or two substituents R ^a , wherein R ^{a is} independently selected from methyl, ethyl, hydroxy, methoxy, ethoxy , Hydroxymethyl, methoxymethyl and ethoxymethyl. According to a further embodiment of the invention, R ^{1 is} C ² -C 8 alkenyl or C 2 -C 8 alkynyl, which may contain one, two, three or four identical or different groups R ^a . In particular, R ¹ means optionally substituted by R ^a C2-C6 alkenyl or C2-C6-alkynyl, preferably C2-C4-alkenyl, the carbonyl by carboxyl, Mehoxycar-, ethoxycarbonyl, formyl or halogen, or C2-C4 alkynyl which is substituted by carboxyl, mehoxycarbonyl, ethoxycarbonyl, formyl or halogen. In particular, R ^{1 is} a radical # -CH = CH ₂ , # -C (CH ₃ ) = CH ₂ , # -CH = CH-CH ₃ , # -C (CH ₃ ) = CH-CH ₃ , # - CH = CH-C ₂ H ₅ , # -CCI = CH-CHO, # -C (CH ₃ ) = CH-C ₂ H ₅ , # -CH = CH-COOH, # -CH = CH-CH (CH ₃ ) ₂ , # -CH = CH-CO-OCH ₃ , # -CH = CH-CO-OC ₂ H ₅ , # -C≡CH, # -C≡C-CH ₃ , # -C≡CC ₂ H ₅ , # -C≡CH-C ₃ H ₇ , # -C≡C-COOH, # -C≡C-COOCH ₃ or # -C≡C-COOC ₂ H ₅ .

According to yet another embodiment of the invention, R ^{1 is} saturated, partially unsaturated or aromatic 5- or θ-membered heterocyclyl which may contain one, two, three or four identical or different groups R ^a .

In the following further embodiments A1) to A6) of the invention, R ¹ stands for:

A1): # -CONW ⁶ W ⁷ , # -CONW ⁷ -N (W ⁷ ) ₂ , # -CO-NW ⁷ -OW ⁷ , # -C00W ⁸ , # -C (S) OW ⁷ ,

#C (O) SW ⁷ , # -C (S) SW ⁷ A2): saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl which may contain one, two, three or four identical or different groups R ^a

A3): # - SW ⁷ , # -SOW ⁷ , # -SO ₂ W ⁷ , # -SO ₃ W ⁷ , # -SON (W ⁷ ) ₂ , # -SO ₂ N (W ⁷ ) ₂

A4): # - P (O) (OW ⁷ ) ₂ , A5): # - B (OW ⁷ ) ₂ , or

A6): # - NW ⁷ OW ⁷ .

According to another

wherein B, D, E, G, L are independently CW ¹² , CW ¹² W ¹³ , N, NW ¹² , O or S, provided that at least one symbol is N, O or S and O is not adjacent and wherein V is C, CW ¹² or N and W ¹² and W ¹³ independently of one another are W ⁷ , halogen, NW ⁷ 2, OH, SW ⁷ or OW ⁷ .

W ⁶ is preferably, in the above embodiments denotes Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, phenyl-Ci-Cio - alkyl, wherein W ^{6 is} unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^a , or W ⁶ is Ci-Cio-haloalkyl, optionally one to three radicals from the group R ^a and wherein R ^{a is} preferably independently selected from cyano, nitro, hydroxy, C ₁ -C 6 -alkyl, C ₁ -C 6 -haloalkyl, C ₃ -C 6 -cycloalkyl, C ₁ -C 6 -alkoxy, C ₁ -C 6 -haloalkoxy, d -Cβ-alkylthio, Ci-Cβ-haloalkyl thio, d-Ce-alkylsulfinyl, d-Ce-haloalkylsulfinyl, Ci-C ₆ alkylsulfonyl, CrC ₆ - haloalkylsulfonyl, Ci-Cβ alkylamino, di-Ci-Cβ-alkylamino, C2-C6-alkenyl, C2-C6 Alkenyloxy, C2-C6 alkynyl and Cs-Cβ alkynyloxy.

W ⁷ in the abovementioned embodiments is preferably hydrogen, W ⁶ or two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ together form a cycle having 3 to 6 carbon atoms which is saturated or partially unsaturated and is unsubstituted or or two further heteroatoms selected from N, S and O, wherein O atoms may not be adjacent.

W ⁸ in the abovementioned embodiments is preferably hydrogen, an alkali or alkaline earth metal cation, Cu cation, NH ₄ ⁺ , mono (C 1 -C 10) alkylammonium, di (C 1 -C 10) alkylammonium, tri (C 1 -C 10) -alkylammonium, Tetra (Ci-Cio) alkylammonium, wherein the alkyl substituents of the ammonium ions can optionally be substituted by aryl or hydroxy, cholinium, C2-Cio-alkenyl, C2-Cio-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkenyl wherein W ^{8 is} unsubstituted or partially or fully halogenated and / or optionally carries one to three radicals from the group R ^a , or W ⁸ is Ci-Cio-halo genalkyl, the optionally one to three radicals from the group R ^a bears or W ⁸ is C 1 -C 10 -alkyl which is partially or completely halogenated and / or carries one to three radicals from the group R ^a , R ^{a being} preferably independently selected from cyano,

Nitro, hydroxy, Ci-C ₆ alkyl, Ci-C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ - haloalkoxy, dC ₆ alkylthio, dC ₆ haloalkylthio, d- Cβ-alkylsulfinyl, CrC ₆ - haloalkylsulfinyl, dC ₆ alkylsulfonyl, dC ₆ haloalkylsulfonyl, -C ₆ alkylamino, di-CrCβ-alkylamino, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6 alkynyl and C3 C6 alkynyloxy.

According to a further embodiment of the invention, R ^{1 represents} # -CONW ⁶ W ⁷ , # -CONW ⁷ -N (W ⁷ ) ₂ , # -CO-NW ⁷ -OW ⁷ , # -COOW ⁸ , # -C (S) OW ⁷ , # -C (O) SW ⁷ , # -SW ⁷ , # -SOW ⁷ , # -SO ₂ W ⁷ , # -SO ₃ W ⁷ , # -SON (W ⁷ ) ₂ , # -P (O ) (OW ⁷ ) ₂ , B (OW ⁷ ) ₂ , pyrrolyl, imidazolinyl, pyrazolyl, 1, 3,4-triazolyl, thiazolyl, 1, 3, 4-oxadiazolyl, 1, 3,4-thiadiazolyl, oxazolyl, Tetrazolyl, oxadiazinyl, 4H- [1,2,4] oxadiazin-3-yl, dioxazinyl, 5,6-dihydro [1,2,2] -dioxy-zin-3-yl, pyridyl, whereupon the heterocyclic radicals are substituted are independently selected by one or more radicals from C 1-6 -alkyl and halogen.

W ⁶ in the abovementioned embodiments is preferably selected from C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -cycloalkyl, benzyl, CONW ⁷ OW ⁷ , COOW ⁸ , carboxy-d-d-alkyl and CN.

W ⁷ in the abovementioned embodiments is preferably selected from hydrogen and W ⁶ , or two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ together form a cycle, as defined above. W ⁸ in the abovementioned embodiments is preferably selected from among hydrogen, Na ⁺ , K ⁺ , ½Ca ²⁺ , ½Mg ²⁺ , Cu ⁺ , NH ₄ ⁺ , [NH (CH ₃ ) S] ⁺ , [N (CH ₃ ) ₄ ] ⁺ , [HN (C ₂ H ₅ ) ₃ ] ⁺ , [N (C ₂ H ₅ ) ₄ ] ⁺ , [H ₂ N (iC ₃ H ₇ ) ₂ ] ⁺ , [H ₃ NCH ₂ Ph] ⁺ , [(H ₃ C) NCH ₂ Ph] ⁺ , [H ₂ N (benzyl) ₂ ] ⁺ , [H ₃ N (benzyl)] ⁺ optionally in whole or in part by F and / or Cl, CONW ⁶ W ⁷ , CONW ⁷ OW ⁷ , carboxy-C 1 -C ₄ -alkyl, substituted C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, allyl, propargyl, cyclopropyl, benzyl , (CHR ^w -CHR ^w -O) _m - (Ci-C ₄ ) alkyl with R ^W = H or CH ₃ and m = 1 to 6.

R ¹ means according to another embodiment # -CONW ⁶ W ⁷ , # -CONW ⁷ "N (W ⁷ ) ₂ , # -CO-NW ⁷ -OW ⁷ , # -C00W ⁸ , # -SW ⁷ , # -SOW ⁷ , -SO ₂ W ⁷ , # -SO ₃ W ⁷ , # -SON (W ⁷ ) ₂ , # - P (O) (OW ⁷ ) ₂ , 1 H-pyrrolyl, 1 H-imidazolyl, 1, 3, 4-oxadiazolyl, 1H-pyrazolyl-1H-1, 3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [1, 2,4] oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [1, 4,2] -dioxyzine-3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals independently selected from C 1 -C ₄ -alkyl and halogen

W ⁶ is C ₁ -C 8 -alkyl, C ₃ -C ₆ -alkenyl, C ₁ -C 8 -cycloalkyl, benzyl, carboxy-C ₁ -C ₄ -alkyl;

W ⁷ is hydrogen or W ⁶ or or two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ together form a cycle, as defined above; and

W ⁸ is hydrogen, Na ⁺ , K ⁺ , NH ₄ ⁺ , [HN (C ₂ H ₅ ) ₃ ] ⁺ , [H ₂ N (iC ₃ H ₇ ) ₂ ] ⁺ , [H ₂ N (benzyl) ₂ ] ⁺ , [H ₃ N (benzyl)] ⁺ optionally in whole or in part by F and / or Cl, substituted C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, allyl, propargyl, cyclopropyl, Benzyl, (CHR ^w -CHR ^w -O) _m - (C 1 -C ₄ ) -alkyl with R ^W = H or CH ₃ and m = 1 to 6.

According to a particular embodiment of the invention, R ^{1 is} selected from CO-NH-CH ₃ , CON (CH ₂ ) ₂ , CONH (IC ₃ H ₇ ), CO-morpholin-1-yl, COOH, COO-propen-3-yl, COO-benzyl, COOCH ₂ CH ₂ OCH ₃ , SO ₃ H, SO ₂ CH ₃ , COO-K ⁺ , COO-Na ⁺ , CONCH ₃ OCH ₃ , COOCH (CH ₃ ) COOCH ₃ , COOCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₃ , COOCH ₂ CH ₂ OCH ₃ , COOCH ₂ COOCH ₃ , COOC ₂ H ₅ , COOCH ₂ CF ₃ , CONHCH (CH ₃ ) COOCH ₃ , CONHCH ₂ COOCH ₃ , (R) COOCH (CH ₃ ) CONHCH ₃ , COOCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₃ COOCH ₂ CONCH ₃ OCH ₃ , 2-pyridyl, 3-CH ₃ -1, 2,4-triazol-5-yl, oxadiazol-2-yl, CONCH ₃ OCH ₃ , CONH (CH ₂ ) ₂ OCH ₃ , CONHCH ₂ CN, COO (CH ₂ ) ₂ O (CH ₂ ) ₂ O (CH ₂ ) ₂ OCH ₃ , COO-2-carboxymethylphenyl, COOPhenyl, CONH-morpholin-1-yl, CONHC (CH _{3) 2} - C≡CH, CON HCH (CH ₃₎ CH ₂ OCH _3, COO-NH ₂ [CH (CHS) _{2] 2} ^+, CONHOH, COO-NH ₄ ^+, 1, 3,4-oxathiazole -2-one-5-yl, 5-aminothiadiazol-2-yl, ₂ cyclo CCNCH ₃ H _5, CONHC (CH _{3) 2} CN, CONHCH ₂ CH ₂ OH, dioxazine-3-yl, N (C≡N) CH (CH _{3) 2,} N (C = N) CH ₂ CH ₂ CH ₂ CH _3, N (C = N) CH ₂ CH ₂ CH ₃ , N (C = N) C ₂ H ₅ , NH ₂ , oxadiazin-3-yl, oxazol-2-yl, PO (OC ₂ Hs) ₂ , PO (OH) OC ₂ H ₅ , SO ₂ NCH (CH ₂ ) ₂ , COOH-C ₃ H ₇ , COOCH ₂ CF ₃ , COO-NH ₄ ⁺ , COO ^"

NH ₂ [CH (CH _{3) 2] 2} ^+, CONHCH (CH ₃₎ CH ₂ OH, COO (CH _{2) 2} O (4-carboxymethylphenyl) COOCH (CH ₂ OX) _2, COOCH ₂ -C≡CH, CONHCH (CH ₃ ) CH ₂ OCH ₃ , CONHOH, COO Propen-3-yl, N (C≡N) CH ₂ -cyclo-C ₄ H ₇ , NO ₂ , CONH-2-pyrimidinyl, CONH, CH ₂ COOC ₂ H ₅ , COO-NH (CH ₂ CHS) ₃ ⁺ , COO (CH ₂ ) ₂ C (CH ₃ ) 3, COO (CH ₂ ) ₂ -C≡CH, COO (CH ₂ ) ₂ CF ₃ , COO (CH ₂ ) ₂ CH (CH ₃ ) ₂ , COO (CH ₂ ) ₂ CH ₂ Br, COO (CH ₂ J ₂ CH ₂ Cl, COO (CH ₂ ) ₂ CH ₂ F, COO (CH ₂ ) ₂ OC (CH ₃ ) ₃ , COO (CH ₂ ) ₃ OCH ₃ , COO (CH ₂ ) ₄ CH ₃ , COO (CH ₂ ) ₅ CH ₃ , COO (CH ₂ ) ₉ CH ₃ , COO-2-carboxymethylphenyl, COO-4-i-propylphenyl, COOC (CHs) ₂ - C≡CH, COOC (CHS) ₂ CH ₂ OCHS, COOCH (CH ₃ ) C (CH ₃ ) S, COOCH (CHS) CFS, COOCH (CHS) CH (CHS) ₂ , COOCH (CH ₃ ) CH ₂ CH ₃ , COOCH (CHS ) CH ₂ OCHS, COOCH (CHS) - cyclohexyl, COOCH (C ₂ H ₅ ) -4-methylphenyl, COOCH ₂ C (CHS) ₃ , COOCH ₂ -C≡CH, COOCH ₂ CH ₂ Br, COOCH ₂ CH ₂ CH ₂ CHS, COOCH ₂ CH ₂ CHS, COOCH ₂ CH ₂ OCH ₃ , COOCH ₂ CH = CHCHS, COOCH ₂ CI, COOCH ₂ F, COOCH (CHS) CH = CH ₂ , COO-cyclo-C ₆ H ₅ , CON ( CH ₃ ) COCH (NH ₂ ) CH ₃ , CONH (CH ₂ ) ₂ OCHS, CONH ₂ , oxazol-2-yl, COOCH (CHS) COOC ₂ H ₅ , CONCHSOCHS, COOCH ₂ COOCH ₃ ,

SO ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ OCHS, SO ₂ OC ₂ H ₅ , SO ₂ OIC ₃ H ₇ , SO ₃ -NH ₄ ⁺ , CONH (CH ₂ ) ₂ OCH ₃ , SO ₂ NH ₂ , SO ₂ NCH (CHs) ₂ , SCH ₃ , SO ₂ NHCH ₃ , CH = CH ₂ , CH = CHCOOH, CH = CHCOOC ₂ H ₅ , C≡CH, CH = CH (IC ₃ H ₇ ), C (CI) = CH ( CHO), C (CHs) = CH _2, CH = CHBr, C (NH ₂₎ = NOH,

CH = N (4-chlorophenyl), CH = N (CH ₂ COOCHs), C (NH ₂ ) = O, C (NH ₂ ) = N (OCH ₂ -2-naphthyl), C (NH ₂ ) = N ( O-benzyl), C≡N, COOCH ₃ , C (NH ₂ ) = NOCH ₃ , C (NH ₂ ) = NOCH ₂ CH = CH ₂ , CH ₂ OC ₂ H ₅ , CH ₂ OCH ₃ , CH = NOH, CH = NOCH ₃ , C (CHs) = NOH, C (CHs) = NOCH ₃ , CH ₂ OH, CH (CH ₃ ) OH, C (cyclo-CsH ₅ ) OH, CH (OCHS) CH (CHS) ₂ , CH (OH) CH ₂ Cl, C (CH ₃ ) (OH) CH (CHS) ₂ , CH (OH) CH (CHs) ₂ , CH (OH) C≡CCH ₃ , CH (OH) C≡CH, CH (CF ₃ ) OH, CH (OH) C (CHs) = CH ₂ , CH (CHS) OCH (CHS) ₂ , C (CFS) ₂ OCH ₃ and

⁰ . According to a specific embodiment of this embodiment, R ^{1 is} selected from CO-NH-CH ₃ , CON (CH ₂ ) ₂ , CONH (IC ₃ H ₇ ), CO-morpholin-1-yl, COOH, COO-propen-3-yl, COO-benzyl, COOCH ₂ CH ₂ OCHS, SO ₃ H, SO ₂ CH ₃ , COO K ⁺ , COO "Na ⁺ , COOCH ₂ CH ₂ OCHS, COOCH ₂ COOCHS, COOC ₂ H ₅ , CONHCH ₂ COOCHS, 2-pyridyl , 3-CH ₃ -1, 2,4-triazol-5-yl, CONCH ₃ OCH ₃ , CONH (CH ₂ ) ₂ OCH ₃ , CONHCH ₂ CN, COOPhenyl, CONHC (CH ₃ ) ₂ -C≡CH , CONHOH, COO-NH ₄ ⁺ , 1, 3,4-oxathiazol-2-one-5-yl, 5-aminothiadiazol-2-yl, CONHCH ₂ CH ₂ OH, dioxazin-3-yl, N (C≡N ) CH (CH ₃ ) ₂ , N (C≡N) CH ₂ CH ₂ CH ₃ , NH ₂ , oxadiazin-3-yl, oxazol-2-yl, PO (OH) OC ₂ H ₅ , SO ₂ NCH (CHs ) ₂ , COO-i-CsH ₇ , CONHCH (CHS) CH ₂ OH, COOCH (CH ₂ OCHS) ₂ , COOCH ₂ -C≡CH,

CONHCH (CHS) CH ₂ OCHS, CONHOH, COO-Propen-3-yl, NO ₂ , CONH-2-pyrimidinyl, CONHCH ₂ COOC ₂ H ₅ , CH ₂ COOC ₂ H ₅ , COO-NH (CH ₂ CHS) ₃ ⁺ , COO (CH ₂ ) ₂ -C≡CH, COO (CH ₂ ) ₂ CH ₂ Br, COO (CH ₂ ) ₂ CH ₂ Cl, COO (CH ₂ ) ₂ OC (CH ₃ ) ₃ , COO (CH ₂ ) ₃ OCH ₃ , COOC (CH ₃ ) ₂ -C≡CH, COOC (CHS) ₂ CH ₂ OCHS, COOCH (CHS) CH ₂ CHS, COOCH (CHS) CH ₂ OCHS, COOCH (CH ₃ ) cyclohexyl, COOCH ₂ C (CHS) ₃ , COOCH ₂ CH ₂ Br, COOCH ₂ CH ₂ CHs, COOCH ₂ CH ₂ OCHS, COOCH (CHS) CH = CH ₂ , COOcycloC ₆ H ₅ , CONH (CH ₂ ) ₂ OCH ₃ , CONH ₂ , oxazol-2-yl, COOCH (CHS) COOC ₂ H ₅ , CONCHSOCHS, COOCH ₂ COOCHS, SO ₂ OC ₂ H ₅ , SO ₂ OH-C ₃ H ₇ , CONH (CH ₂ ) ₂ OCH ₃ , SO ₂ NH _2, SO ₂ NCH (CH) _2, SCH _3, SO ₂ NHCH _3, CH = CH _2, CH = CHCOOH, CH = CHCOOC ₂ H _5, C≡CH, C (CHs) = CH _2, CH = CHBr, C (NH ₂ ) = NOH, C (NH ₂ ) = O, C≡N, COOCH ₃ , C (NH ₂ ) = NOCH ₃ , C (NH ₂ ) = NOCH ₂ CH = CH ₂ , CH ₂ OC ₂ H ₅ , CH ₂ OCH ₃ , CH = NOH, CH = NOCH ₃ , C (CHs) = NOH, C (CHs) = NOCH ₃ , CH ₂ OH, CH (CH ₃ ) OH, CH (OH) CH (CHs) ₂ , CH (OH) C = CCH ₃ , CH (OH) C≡CH, CH (OH) C (CH ₃ ) = CH ₂ , and

O. According to another specific embodiment of this embodiment, R ^{1 is} selected from CO-NH-CH ₃ , CON (CH ₃ ) ₂ , CONH (iC ₃ H ₇ ), COOH, COO-benzyl, COOCH ₂ CH ₂ OCH ₃ , SO ₃ H , SO ₂ CH ₃ , COO K ⁺ , COO-Na ⁺ , COOC ₂ H ₅ , 2-pyridyl, 3-CH ₃ -1, 2,4-triazol-5-yl, CONCH ₃ OCH ₃ , COOPhenyl, CONHOH, COO-NH ₄ ⁺ , 1, 3,4-oxathiazol-2-one-5-yl, 5-aminothiadiazol-2-yl, CONHCH ₂ CH ₂ OH, NH ₂ , oxadiazin-3-yl, oxazol-2-yl , SO ₂ NCH (CH ₂ ) ₂ , COOH-C ₃ H ₇ , CONHOH, COO-propen-3-yl, NO ₂ , CONHCH ₂ COOC ₂ H ₅ , COO (CH ₂ ) ₂ CH ₂ Br, COO (CH ₂ ) ₂ CH ₂ Cl, COO (CH ₂ ) ₃ OCH ₃ , COOCH ₂ CH ₂ Br, COOCH (CH ₃ ) CH = CH ₂ , CONH (CH ₂ ) ₂ OCH ₃ , CONH ₂ , oxazol-2-yl,

COOCH (CH ₃ ) COOC ₂ H ₅ , CONCH ₃ OCH ₃ , COOCH ₂ COOCH ₃ , SO ₂ NH ₂ , SO ₂ NCH (CHS) ₂ , SCH ₃ , SO ₂ NHCH ₃ , CH = CH ₂ , CH = CHCOOH, CH = CHCOOC ₂ H ₅ , C≡CH, C (CHs) = CH ₂ , CH = CHBr, C (NH ₂ ) = NOH, C (NH ₂ ) = O, C≡N, COOCH ₃ , C (NH ₂ ) = NOCH ₃ , CH ₂ OC ₂ H ₅ , CH ₂ OCH ₃ , CH = NOH, CH = NOCH ₃ , C (CH ₃ ) = NOH, C (CH ₃ ) = NOCH ₃ , CH ₂ OH, and

In this case, the other substituents according to formula I preferably have the meanings described herein as preferred, in particular compositions which as component 1) at least one compound selected from the compounds of the formulas Ia.1, La.2, Ia.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, object of this invention, wherein the substituents Y and Z have the meanings and combinations of meanings as given for the compounds in Tables 1 to 257, and R ¹ has one of the meanings of the embodiments just described.

According to a further embodiment of the invention, R ^{1 is} hydrogen, fluorine, chlorine or bromine, in particular hydrogen.

According to another specific embodiment of the invention, R ^{1 is} cyano.

According to one embodiment of the invention, R ^{2 is} cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C 1 -C ₄ -haloalkyl having 1 to 9 halogen atoms, independently selected from fluorine, chlorine and bromine, C 1 -C ₄ -alkyl, C _{3-C6-cycloalkyl,} thiocarbamoyl, -C ₄ - alkoxycarbonyl, _{Ci-C4-alkylcarbonyl, hydroxyimino-Ci-C4-alkyl} or Ci -C ₄ -alkyl koxyimino- Ci-C ₄ alkyl.

In another embodiment, R ^{2 is} hydrogen. In another embodiment, R ^{2 is} cyano.

According to another preferred embodiment, R ¹ and R ² each represent are each hydrogen, cyano, halogen or Ci-C ₄ -AlkVl, and in one embodiment both mean hydrogen. In another preferred embodiment, R ^{1 is} CN and R ² is hydrogen.

According to one embodiment of the compositions according to the invention, X in the compounds of the formula I is halogen, cyano, -C ₄ -alkoxy, CrC ₄ - haloalkoxy, _Ci-C4-alkyl or Ci-C ₄ haloalkyl.

According to one embodiment, X denotes C 1 -C ₄ -alkyl, in particular methyl, ethyl, isopropyl or n-propyl. According to a specific embodiment, X is methyl.

According to a further embodiment, X is C 1 -C ₄ -haloalkyl, in particular halomethyl, such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.

Also preferably X is C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -haloalkenyl, preferably C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -haloalkenyl.

According to another embodiment, X is halogen, in particular chlorine or fluorine, especially chlorine.

According to another preferred embodiment, X is C 1 -C ₄ -alkoxy, in particular methoxy or ethoxy. Furthermore, X is preferably C 1 -C ₄ -haloalkoxy.

According to a preferred embodiment of the present invention, X is cyano.

According to one embodiment of the invention, when Y is a heteroaromatic or aromatic radical, Y contains at least one substituent L which is preferably ortho to the point of attachment to the skeleton of the compounds of the formula I.

In the compounds of formula I, unless otherwise stated, when L is attached to a ring nitrogen of Y, it is particularly preferred that each L is independently:

Ci-Cs-alkylcarbonyl, Ci-Cs-alkylthiocarbonyl; or

Ci-Cβ alkyl, Ci-Cβ-haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, Ci-Cs-alkoximinoalkyl, C2-C8-alkenyloximino- (Ci-C8) -alkyl or C2-C8-alkynyloximino-Ci-C8-alkyl. With particular preference L is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, more preferably C 1 -C ₄ -alkyl or C 1 -C ₄ -haloalkyl, in particular methyl or ethyl, more preferably methyl.

In this case, L, when it is bonded to a ring nitrogen of Y, is particularly preferably C 1 -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, -COO (C ₁ -C ₄ ), -CONH ₂ or -CSNH ₂ , in particular methyl, ethyl, isopropyl, cyclopropyl or -COOCH 3.

When L is attached to a ring carbon of Y and unless otherwise specified, L is preferably each independently:

Ci-Cs-alkylcarbonyl, Ci-Cs-alkylthiocarbonyl; or

Ci-Cβ alkyl, Ci-Cβ-haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, C ₁ -Cs -alkoximinoalkyl, C ₂ -C 8 -alkenyloximino-C ₁ -C 8 -alkyl, C ₂ -C 8 -alkynyloximino-C ₁ -C 8 -alkyl; or

Halogen, cyano, hydroxy, nitro, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, or

C 1 -C 8 -alkoxy, C 1 -C 5 -haloalkoxy, C 1 -C 8 -alkenyloxy, C 1 -C 5 -haloalkenyloxy, C 1 -C 5 -alkynyloxy, C 1 -C 8 -haloalkynyloxy, C 1 -C 8 -cycloalkoxy, C 1 -C 8 -halocycloalkoxy; or

Fluorine, chlorine, methyl, methoxy.

In the compounds of the present invention, Y may contain one to four, one to three, or one or two identical or different substituents L. According to one embodiment, Y contains the same substituents L. Y preferably contains one or two substituents L, more preferably one or two identical substituents L. Furthermore, Y preferably has two identical substituents L.

In a preferred embodiment of the invention, Y is a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, Nitrogen and sulfur, wherein the heterocycle is unsubstituted or substituted by one, two, three or four identical or different substituents L. According to one embodiment of the invention, the heterocycle is attached via carbon to the backbone of the compounds of formula I. According to a further embodiment, the heterocycle is bonded to the skeleton of the compounds of the formula I via nitrogen. This also applies to the further embodiments of this embodiment of the invention described below. According to one In a preferred embodiment, the heterocycle contains at least one nitrogen atom as ring member.

According to a further embodiment, Y is a saturated, fully unsaturated, fully or partially unsaturated or aromatic heterocyclyl containing one, two or three heteroatoms from the group consisting of oxygen, nitrogen and sulfur, wherein the Heterocycle is unsubstituted or substituted by one or two identical or different substituents L, which are preferably independently selected from halogen, hydroxy, mercapto, cyano, nitro, carboxy-C 1 -C ₄ -alkyl, C 1 -C ₄ -alkyl, C 1 -C ₄ - AIkOXy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio and C ₃ -C ₆ -cycloalkyl.

In another preferred embodiment Y is an unsubstituted or substituted five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle containing one, two or three heteroatoms from the group O, N and S as In this formula, Y preferably contains an unsubstituted or substituted five-, six- or seven-membered saturated or partially unsaturated heterocycle which contains one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms , Also preferably, the heterocycle contains one or two nitrogen atoms. "Partially unsaturated" means that the heterocycle does not form an aromatic system, wherein the heterocycle preferably contains one or two double bonds.

In specific embodiments of this embodiment, Y represents N-piperidinyl or N-morpholinyl which are unsubstituted or substituted by one, two, three or four substituents L independently selected from fluoro, chloro, bromo, cyano, nitro, hydroxy, mercapto, methyl , Ethyl, methoxy, methylthio, hydroximinomethyl, hydroxyminoethyl, methoximinomethyl, methoxyiminoethyl and trifluoromethyl.

According to a further embodiment, the invention relates to compositions containing as component 1) at least one compound I in which Y is an optionally substituted by L aromatic heterocycle, preferably a five- or six-membered aromatic heterocycle.

In one embodiment, Y contains at least one ring nitrogen atom. It may be preferred that the binding site of Y to the skeleton of the formula I is in the ortho-position to the at least one nitrogen atom.

According to a preferred embodiment of the present invention, the heteroaryl (Y) has at least one substituent which is in the ortho position to the point of attachment to the skeleton of the formula I to which Y is bonded. It may be particularly preferred if the ortho-L is fluorine, chlorine, (Ci-C2) -alkyl, such as Methyl or ethyl, Ci-C2-fluoroalkyl such as trifluoroalkyl or Ci-C2-alkoxy such as methoxy.

According to a preferred embodiment of this embodiment, Y is a 5-membered heteroaryl radical containing at least one nitrogen atom as ring member and optionally one or two further heteroatoms as ring members selected from O, S and N, which is unsubstituted or substituted by one, two or three Substituents L. Examples of these are pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, thiazolyl, isoxazolyl and isothiazolyl, which are unsubstituted or carry 1, 2 or 3 substituents L. can. Among them, Y is preferably thiazolyl, imidazolyl, pyrazolyl, 1,2,4-triazolyl or 1,2,3-triazolyl, in particular pyrazol-1-yl, which are unsubstituted or carry one, two or three identical or different substituents L. In another embodiment Y is thienyl.

In another embodiment, Y is N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1, 2,4-triazolyl or N-pyrrolyl which are unsubstituted or substituted by one, two, three or four substituents L. independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoxyiminoethyl and trifluoromethyl.

Specific examples of Y according to this embodiment of the invention are

3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropylpyrazol-1-yl, 3-isopropyl-5-methylpyrazol-1-yl, 3-ethyl-5 -methylpyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3-chloropyrazol-1-yl, 3-methylpyrazol-1-yl, 3-methyl-4-chloropyrazol-1-yl, 3 Trifluoromethylpyrazole-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methylpyrazol-1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro 4-methylpyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl, 3,5-ditrifluoromethylpyrazol-1-yl, 3,4-dichloro-5-trichloromethylpyrazol-1-yl, 1 , 3-Dimethylpyrazol-5-yl, 1-methyl-3-trifluoromethylpyrazol-5-yl, 1, 5-dimethylpyrazol-3-yl, 1-methyl-5-methoxypyrazol-3-yl, 1, 3-dimethylpyrazole-4 -yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl, 1-methyl-5-trifluoromethylpyrazol-4-yl, 1 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl;

1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5-dichloropyrrol-2-yl;

- thiazol-4-yl, thiazol-2-yl, thiazol-5-yl, each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, Methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyimi- noethyl and trifluoromethyl; specific examples of this embodiment of the invention are 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl, 2,5-dichlorothiazol-4-yl;

3-methylisothiazol-4-yl, 3-methyl-5-chloroisothiazol-4-yl, isothiazol-3-yl and isothiazol-5-yl;

- isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazol-4-yl, 3-chloroisoxazol-4-yl, isoxazol-3-yl and isoxazol-5-yl;

Oxazol-4-yl, 2-methyloxazol-4-yl, 2,5-dimethyloxazol-4-yl, oxazol-2-yl and oxazol-5-yi;

4,5-dichloroimidazol-1-yl, 4,5-dimethylimidazol-1-yl, 1-methylimidazol-4-yl, 1-methylimidazol-2-yl and 1-methylimidazol-5-yl;

3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazol-1-yl, 3 Trifluoromethyl-1,2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1,2,4-triazol-1-yl , 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl, 3,5-ditrifluoromethyl-1,2,4-triazole 1 -yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-

Dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl, 5-methyl-1,2,3-triazol-1-yl, 5-chloro-1,2,3-triazol-1-yl, 5-fluoro-1,2,3-triazol-1-yl, 5- Bromo-1, 2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl, 1, 2,3-triazol-2-yl, 1-methyl-1, 2, 4-triazol-5-yl, 1-methyl-1,2,3-triazol-5-yl, 2-methyl-1,2,3-triazol-4-yl, 1-methyl-1, 2,4- triazol-3-yl, 1-methyl-1,2,3-triazol-4-yl and 2-methyl-1,2,3-triazol-5-yl,

2-thienyl, 3-thienyl, each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximi- nomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyiminoethyl and trifluoromethyl; specific examples of this embodiment of the invention are 5-methylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 3,5-dichlorothiophen-2-yl, 3,4,5-trichlorothiophene 2-yl, 5-bromothiophen-2-yl, 2-methylthiophen-3-yl, 2,5-dichlorothiophen-3-yl, 2,4,5-trichlorothiophen-3-yl and 2,5-dibromothiophene-3 yl.

According to a further embodiment of the invention, Y is thiazolyl, imidazolyl, pyrazolyl, 1, 2,4-triazolyl or 1, 2,3-triazolyl and especially pyrazol-1-yl, where the abovementioned radicals are unsubstituted or 1, 2 or Have 3 substituents L.

In this embodiment, Y is in particular one of the radicals Het-1 to Het-31 given below:

Het-10 Het-1 1 Het-12 Het-13 Het-14

Het-22

wherein

# denotes the point of attachment; and L ¹ , L ² , and L ^{3 are} independently hydrogen or have one of the meanings given for L.

Preferably, the radicals L ¹ , L ² and L ^{3 are} independently selected from hydrogen, halogen, nitro, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, especially C 1 -C ₂ -fluoroalkyl, C 1 -C ₄ -alkoxy and C 1 -C ₄ -alkoxycarbonyl. In particularly preferred embodiments, L ¹ , L ² and L ^{3 are} independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.

Examples of Het-1 are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazole 1 -yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethylpyrazol-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazole 1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3, 5-Ditrifluoromethyl-pyrazol-1-yl and 3,4-dichloro-5-trichloromethylpyrazole.

Examples of Het-2 are 1, 3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-5-yl.

Examples of Het-3 are 1, 5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypyrazol-3-yl.

Examples of Het-4 include 1, 3-dimethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.

Examples of Het-5 are 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.

Examples of Het-6 are 1, 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.

Examples of Het-7 include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichloro-thiazol-4-yl.

An example of Het-8 is thiazol-2-yl.

An example of Het-9 is thiazol-5-yl.

Examples of Het-10 include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl. An example of Het-1 1 is isothiazol-3-yl.

An example of het-12 is isothiazol-5-yl.

Examples of het-13 include isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl,

An example of Het-14 is isoxazol-3-yl.

An example of Het-15 is isoxazol-5-yl.

Examples of Het-16 include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,

An example of Het-17 is oxazol-2-yl.

An example of het-18 is oxazol-5-yl.

Examples of Het-19 include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.

An example of Het-20 is 1-methyl-imidazol-4-yl.

An example of Het-21 is 1-methylimidazol-2-yl.

An example of Het-22 is 1-methylimidazol-5-yl.

Examples of het-23 include 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazole 1 -yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1, 2,4- triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1, 2,4-triazol-1-yl.

Examples of Het-24 include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl, 5-methyl 1, 2,3-triazol-1-yl, 5-chloro-1, 2,3-triazol-1-yl, 5-fluoro-1, 2,3-triazol-1-yl, 5-bromo-1, 2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl.

An example of Het-25 is 1,2,3-triazol-2-yl.

An example of Het-26 is 1-methyl-1,2,4-triazol-5-yl.

An example of Het-27 is 1-methyl-1,2,3-triazol-5-yl. An example of Het-28 is 2-methyl-1,2,3-triazol-4-yl.

An example of Het-29 is 1-methyl-1,2,4-triazol-3-yl.

An example of Het-30 is 1-methyl-1,2,3-triazol-4-yl.

An example of Het-31 is 2-methyl-1,2,3-triazol-5-yl.

According to another preferred embodiment of the invention, Y is thienyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, Y represents one of the following residues Het-32 or Het-33, in which # denotes the attachment site and L ¹ , L ² , and L ³ independently of one another have the meanings given above for the formulas Het-1 to Het-31.

Examples of Het-32 are 2-thienyl, 5-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 3,5-dichlorothiophene-2-yl, 3,4,5- Trichlorothiophen-2-yl and 5-bromothiophen-2-yl.

Examples of Het-33 are 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3 yl.

A further embodiment of the invention relates to compounds of the formula I in which Y is 1, 2,3-triazolyl or 1,2,4-triazolyl, where Y may have two identical or different substituents L.

Preferred embodiments of this Y are 3,5-dimethyl-1, 2,4-triazol-1-yl, 3,5-dichloro-1, 2,4-triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl, 3,5-di- (trifluoromethyl) -1, 2,4-triazol-1-yl, 3-methyl-1, 2,4-triazol-1-yl, 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3 bromo-1, 2,4-triazol-1-yl, 3-trifluoromethyl-1,2,4-triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4, 5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1,2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazole-1 - yl, 4,5-di- (trifluoromethyl) -1, 2,3-triazol-1-yl, 5-methyl-1,2,3-triazol-1-yl, 5-chloro-1, 2,3- triazol-1-yl, 5-fluoro-1,2,3-triazol-1-yl, 5-bromo-1,2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazole 1 -yl.

In another embodiment, Y is a five-membered nitrogen-containing heteroaromatic ring selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl, wherein Y is unsubstituted or substituted with one, two, three or four same or different Substituents L. According to one embodiment, Y here is unsubstituted or substituted pyrrolidinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl or isothiazolyl. According to one embodiment of the invention, Y is optionally substituted pyrrolyl, preferably via a ring carbon bonded to the backbone of formula I pyrrolyl, so 2-, or 3-pyrrolyl, more preferably 2-pyrrolyl. Preferably, the pyrrolyl radical has one, two, three or four substituents L. Preferably, there is a substituent on the nitrogen atom of the pyrrolyl ring.

According to a further embodiment of the invention, Y is optionally substituted pyrazolyl, such as 1-, 3-, 4- or 5-pyrazolyl. Particularly preferred is Y 1-pyrazolyl or 4-pyrazolyl, more preferably 1-pyrazolyl. The pyrazolyl radical preferably has one, two or three substituents L.

According to one embodiment of the invention, Y is optionally substituted imidazolyl, ie 1-, 2-, or 4-imidazolyl, more preferably 1- or 2-imidazolyl. Preferably, the imidazolyl radical has one, two or three substituents L.

Preferred substitution patterns of Y are as indicated in the following Table A, wherein L ¹ , L ² and L ³ within a heteroaromatic Y are each the same or different L, which are as defined above:

A-11 A-12 A-13 A-14

A-33

A-34 A-35 A-36 A-37

A-38 A-39 A-40 A-41

In the structures in Table A, # means in each case the point of attachment of the respective Y to the skeleton of the compounds of the formula I in each case independently of one another have the meanings given herein for L.

When Y is pyrrolyl, a substitution pattern selected from A-1, A-2, A-3, A-4 and A-5, especially selected from A-2 and A-4 shown in Table A is particularly preferred.

When Y is pyrazolyl, a substitution pattern is selected from A-7, A-8, A-10, A-11, A-13, A-14, A-15, A-16 and A-19. Particularly preferred is A-10, in particular with U = L ² .

When Y is imidazolyl, a substitution pattern is selected from A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29 and A-30. specifically selected from A-22, A-23, A-24, A-25 and A-27, A-28, and A-29.

When Y is oxazolyl, a substitution pattern selected from A-36 and A-37 is particularly preferable. When Y is isoxazolyl, a substitution pattern selected from A-39, A-40 and A-41 is particularly preferable.

When Y is thiazolyl, a substitution pattern selected from A-44 and A-45 is particularly preferred.

When Y is isothiazolyl, a substitution pattern selected from A-46 and A-47 is particularly preferable.

Specific embodiments of Y are: 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl, 1-methyl-3,5-dichloropyrrol-2-yl, 3-methyl-5-isopropylpyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 3-isopropyl-5-methylpyrazol-1-yl, 3-ethyl-5-methylpyrazol-1-yl, 3 Methyl 5-methoxypyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 3,4-dichloro 5-trichloromethylpyrazol-1-yl, 3

Methylpyrazol-1-yl, 3,5-dichloro-4-methylpyrazol-1-yl, 3-methyl-4-chloropyrazol-1-yl, 1, 3-dimethylpyrazol-5-yl, 1-methyl-3-trifluoromethylpyrazole 5-yl, 1, 5-dimethylpyrazol-3-yl, 1-methyl-5-methoxypyrazol-3-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethyl-pyrazole-4 yl, 1, 3-dimethylpyrazol-4-yl, 1-methyl-5-trifluoromethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 3,5-dichloropyrazol-1-yl, 3,5- Dibromopyrazol-1-yl, 5-chloropyrazol-1-yl, 5-bromopyrazol-1-yl, 3,4,5-trichloropyrazol-1-yl, 3,4,5-tribromopyrazol-1-yl, 1-methyl 3,5-dichloropyrazol-4-yl, 1-methyl-3,5-dibromopyrazol-4-yl, 4,5-dichloroimidazol-1-yl, 4,5-dimethylimidazol-1-yl, oxazole-4 yl, 2,5-dimethyloxazol-4-yl, 2-methyloxazol-4-yl, isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-chloroisoxazol-4-yl, 3-methylisoxazole 4-yl, 2-methylthiazol-4-yl, thiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl, 2,5-dichlorothiazol-4-yl, 2-methyl-5-bromothiazole-4 yl, 3-methylisothiazol-4-yl, 3-methyl-5-chloroisothiazol-4-yl.

According to a further embodiment of the invention, Y is a five-membered heteroaryl group containing two nitrogen atoms as ring members, which is selected from 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2 , 5-thiadiazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl and 1, 2,5-oxadiazolyl, wherein Y may be unsubstituted or substituted with one or two L, wherein L is as defined above, or is preferably defined.

Special meanings for such Y are: 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3,4] -thiadiazol-2-yl, 5-chloro- [1, 3,4] thiadiazol-2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1,2,3] -thiadiazol-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazole 5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1, 2, 3] -thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl [1, 2,4] thiadiazol-5-yl, 3-chloro [1, 2,4] thiadiazol-5-yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2,4-

Thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazol-3-yl, 5-chloro [1,2,4] thiadiazol-3-yl, 5-bromo [1,2,5 , 4] -thiadiazol-3-yl, 1, 2,5-thiadiazol-3-yl, 4-methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1,2,5] thiadiazol-3-yl, 4-bromo [1,2,5] thiadiazol-3-yl, 1, 3,4-thiadiazol-2-yl, 5-methyl- [1 , 3,4] -thiadiazol-2-yl, 5-chloro [1, 3,4] thiadiazol-2-yl, 5-bromo [1,4,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1,2,3] thiadiazol-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1 , 2,3] -thiadiazol-5-yl, 4-bromo [1,2,3] thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1, 2 , 4] -thiadiazol-5-yl, 3-chloro [1,2,4] thiadiazol-5-yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2, 4-thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazol-3-yl, 5-chloro [1,2,4] thiadiazol-3-yl, 5-bromo [1 , 2,4] -thiadiazol-3-yl, 1, 2,5-thiadiazol-3-yl, 4-methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1,2 , 5] -thiadiazol-3-yl, 4-bromo [1,2,5] thiadiazol-3-yl, 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3,4 ] -thiadiazol-2-yl, 5-chloro [1,3,4] thiadiazol-2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3- Thiadiazol-4-yl, 5-methyl- [1,2,3] thiadiazole l-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazole 5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1,2,3 ] -thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1,2,4] thiadiazol-5-yl, 3-chloro [1,2,4] - thiadiazol-5-yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazole 3-yl, 5-chloro [1,2,4] thiadiazol-3-yl, 5-bromo [1,2,4] thiadiazol-3-yl, 1, 2,5-thiadiazole-3 yl, 4-methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1,2,5] thiadiazol-3-yl, 4-bromo [1,2,5] - thiadiazol-3-yl, 1, 3,4-thiadiazol-2-yl, 5-methyl- [1,3,4] thiadiazol-2-yl, 5-chloro [1,4,4] thiadiazole 2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1,2,3] thiadiazole-4 yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1,2,3] thiadiazole 5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1 , 2,4] -thiadiazol-5-yl, 3-chloro [1,2,4] thiadiazol-5-yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazol-3-yl, 5-chloro [1,2,4] thiadiazol-3-yl, 5-bromo [1,2,4] thiadiazol-3-yl, 1, 2,5-thiadiazol-3-yl, 4-methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1 , 2,5] -thiadiazol-3-yl, 4-bromo [1,2,5] thiadiazol-3-yl, 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3 , 4] -thiadiazol-2-yl, 5-chloro [1,3,4] thiadiazol-2-yl, 5-bromo [1,4,4] thiadiazol-2-yl, 1, 2, 3-Thiadiazol-4-yl, 5-methyl- [1,2,3] thiadiazol-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1 , 2,3] -thiadiazol-4-yl, 1, 2,3-thiadiazol-5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2 , 3] -thiadiazol-5-yl, 4-bromo [1,2,3] thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1, 2,4 ] -thiadiazol-5-yl, 3-chloro [1,2,4] thiadiazol-5-yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2,4- Thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazol-3-yl, 5-chloro [1,2,4] thiadiazol-3-yl, 5-bromo [1,2,5 , 4] -thiadiazol-3-yl, 1, 2,5-thiadiazole-3 -yl, 4-methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1,2,5] thiadiazol-3-yl, 4-bromo [1, 2.5] -thiadiazol-3-yl, 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3,4] thiadiazol-2-yl, 5-chloro [1, 3,4] thiadiazole -2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1,2,3] thiadiazole-4 -yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl , 4-Methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1,2,3] thiadiazole -5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1,2,4] thiadiazol-5-yl, 3-chloro [1,2,4] thiadiazole-5 -yl, 3-bromo [1,2,4] thiadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 5-methyl- [1,2,4] thiadiazol-3-yl , 5-Chloro- [1,2,4] thiadiazol-3-yl, 5-bromo [1,2,4] thiadiazol-3-yl, 1, 2,5-thiadiazol-3-yl, 4 -Methyl- [1,2,5] thiadiazol-3-yl, 4-chloro [1,2,5] thiadiazol-3-yl, 4-bromo [1,2,5] thiadiazole-3 yl. According to another preferred embodiment of this embodiment, Y is a 6-membered heteroaryl radical containing one, two or three nitrogen atoms as ring members, which is unsubstituted or substituted by one, two or three substituents L. Examples of these are pyridinyl, pyrimidinyl, pyrazinyl , Pyridazinyl and triazinyl, in particular pyridinyl, pyrimidinyl and pyrazinyl, which are each unsubstituted or substituted by one, two, three or four independently selected L. Among these, preference is given to compounds of the formula I in which Y is pyridinyl which, if appropriate, contains two, three or four substituents L. Among them, preference is given to compounds in which Y is 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, which is unsubstituted or contains one or two substituents L. Y is furthermore preferably pyrimidinyl, in particular 2- or 4-pyrimidinyl, which is unsubstituted or contains one, two or three substituents L. Y is furthermore preferably 2-pyrazinyl or 4-pyridazinyl which is unsubstituted or contains one, two or three substituents L. Further preferably, Y 1, 3,5-triazinyl, which is unsubstituted or contains one, two or three substituents L.

Specific examples of Y according to this embodiment of the invention are

2-pyridyl, 3-pyridyl, 4-pyridyl, each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, Methylthio, hydroximinomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyiminoethyl and trifluoromethyl; Specific examples of this embodiment of the invention are 3-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 3-bromopyridin-2-yl, 3-trifluoromethylpyridin-2-yl, 3-methylpyridin-2-yl, 3-ethylpyridine -2-yl, 3,5-difluoropyridin-2-yl, 3,5-dichloropyridin-2-yl, 3,5-dibromopyridin-2-yl, 3-fluoro-5-trifluoromethylpyridin-2-yl, 3 , 5-Dimethylpyridin-2-yl, 5-nitropyridin-2-yl, 5-cyanopyridin-2-yl, 5-methoxycarbonylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-methylpyridin-2-yl, 4 -Methylpyridin-2-yl, 6-methyl-pyrid-2-yl, 2-chloropyridin-3-yl, 2-bromopyridin-2-yl, 2-methylpyridin-3-yl, 2,4-dichloropyridin-3-yl , 2,4-Dibromopyridin-3-yl, 2,4-dimethylpyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6 Trimethylpyridin-3-yl, 2,4-dichloro-6-methylpyridin-3-yl, 3-chloropyridin-4-yl, 3-bromopyridin-4-yl, 3-methylpyridin-4-yl, 3.5 Dichloropyridin-4-yl, 3,5-dibromopyridin-4-yl and 3,5-dimethylpyridin-4-yl;

Pyrimidin-2-yl, pyrimidin-4-yl, each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, Methylthio, hydroximinomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyiminoethyl and trifluoromethyl; specific examples of this embodiment of the invention are 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethylpyrimidin-4-yl, 2 , 5-Dimethyl-6-trifluoromethylpyrimidin-4-yl, 5-methyl-6-trifluoromethylpyrimidin-4-yl, 6-trifluoromethylpyrimidin-4-yl, 2-methyl-5-fluoropyrimidin-4-yl, 2-methyl -5- chloropyrimidin-4-yl, 5-chloro-6-methylpyrimidin-4-yl, 5-chloro-6-ethylpyrimidin-4-yl, 5-chloro-6-isopropylpyrimidin-4-yl, 5-bromo-6-methylpyrimidine 4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethylpyrimidin-4-yl, 2,6-dimethyl-5-chloropyrimidin-4-yl, 5,6-dimethylpyrimidine 4-yl, 2,5-dimethyl-pyrimidin-4-yl, 2,5,6-trimethyl-pyrimidin-4-yl, 5-methyl-6-methoxypyrimidin-4-yl, 4-methyl-pyrimidin-5-yl, 4,6- Dimethylpyrimidin-5-yl, 2,4,6-trimethylpyrimidin-5-yl, 4-trifluoromethyl-6-methylpyrimidin-5-yl, 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidine 2-yl, 4,6-ditrifluoromethylpyrimidin-2-yl and 4,6-dimethyl-5-chloropyrimidin-2-yl.

A further preferred embodiment of the invention relates to compounds of

Formula I, wherein Y is 2-pyrazinyl, optionally having 1, 2 or 3 substituents L.

A further preferred embodiment of the invention relates to compounds of the formula I in which Y is 3-pyridazinyl which optionally has 1, 2 or 3 substituents L.

A further preferred embodiment of the invention relates to compounds of the formula I in which Y is 1,3,5-triazinyl which optionally has 1 or 2 substituents L.

Examples of particularly preferred heterocyclic radicals Y of this embodiment

wherein

# denotes the point of attachment; and

L ¹ , L ² , L ³ and L ⁴ independently of one another are hydrogen or have one of the meanings given for L. Preferably, the radicals L ¹ , L ² , L ³ and L ^{4 are} independently selected from hydrogen, halogen, nitro, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, especially C 1 -C ₂ -fluoroalkyl, C 1 -C ₄ -alkoxy and C 1 -C ₄ -alkoxycarbonyl. In particularly preferred embodiments, L ¹ , L ² , L ³ and L ^{4 are} independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl. Examples of Het-34 are 2-pyridyl, 3-fluoro-pyridin-2-yl, 3-chloro-pyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethyl-pyridine-2-yl yl, 3-methylpyridin-2-yl, 3-ethyl-pyridin-2-yl 3,5-difluoropyridin-2-yl, 3,5-dichloro-pyridin-2-yl, 3,5-dibromo -pyridin-2-yl, 3-fluoro-5-trifluoromethyl-pyridin-2-yl, 3,5-dimethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl, 5-cyano-pyridine-2 -yl, 5-methoxycarbonylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-methylpyridin-2-yl, 4-methylpyridin-2-yl, and 6-methylpyridine 2-yl.

Examples of Het-35 are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-2-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridine-3 yl, 2,4-dibromopyridin-3-yl, 2,4-dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6-trimethylpyridin-3-yl and 2,4-dichloro-6-methylpyridin-3-yl.

Examples of Het-36 include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridine-4 yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl

Examples of Het-37 include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2, 5-Dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidine-4 yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 5-chloro-6 isopropyl-pyrimidin-4-yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimidin-4-yl, 2,6-dimethyl-5-chloro-pyrimidin-4-yl, 5,6-dimethyl-pyrimidin-4-yl, 2,5-dimethyl-pyrimidin-4-yl, 2,5,6-trimethyl-pyrimidine 4-yl and 5-methyl-6-methoxy-pyrimidin-4-yl.

Examples of het-38 include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine 5-yl.

Examples of Het-39 include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.

According to a further preferred embodiment of the invention, Y is phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L. When the phenyl group is substituted, it preferably has one, two, three or four substituents L on, which can be the same or different. In this case, L in each case independently has one of the meanings indicated above or given as being preferred for L.

In a specific embodiment of the invention, Y is a substituted phenyl group A,

wherein # is the point of attachment to the pyrazolopyrimidine skeleton and L ^{1 is} fluorine, chlorine, CH ₃ or CF ₃ ;

L ² , L ^{4 are} independently hydrogen, fluorine or methoxy; L ^{3 is} hydrogen, fluorine, chlorine, CN, CH ₃ , OCH ₃ , NH ₂ , NHCH ₃ , N (CH ₂ ) ₂ , C (O) NH ₂ ,

COOCH ₃ or C (O) CH ₃ ; and L ^{5 is} hydrogen, fluorine, chlorine or CH ₃ .

In a further embodiment of the invention, Y is one of the following substituents: 2-fluoro-6-chlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-6-methylphenyl, 2,4, 6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, 2-chloro-4-methoxyphenyl, pentafluorophenyl, 2-methyl-4-fluorophenyl, 2-trifluoromethylphenyl, 2-methoxy-6-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2,3-difluorophenyl, 2,5-difluorophenyl, 2,3, 4-trifluorophenyl, 2-methylphenyl, 2,4-dimethylphenyl, 2-methyl-4-chlorophenyl, 2-methyl-5-fluorophenyl, 2-fluoro-4-methylphenyl, 2,6-dimethylphenyl, 2,4,6- Trimethylphenyl, 2,6-difluoro-4-methylphenyl, 2-trifluoromethyl-4-fluorophenyl, 2-trifluoromethyl-5-fluorophenyl, 2-trifluoromethyl-5-chlorophenyl or 2-fluoro-3-methoxyphenyl.

In another embodiment, Y is phenyl which is unsubstituted or substituted with one, two or three substituents L independently selected from fluoro, chloro, bromo, cyano, nitro, formyl, methyl, ethyl, n -propyl, i -propyl, n Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, methoxy, ethoxy, n-propoxy, i-propoxy, methylthio, ethylthio, n-propylthio, i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl , Ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethynyloxy, trifluoroethinyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n-propylamino, i Propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, hydroxyiminoethyl, ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl, C yclohexyl; and

1,3-linked 1,3-propanediyl, methylenedioxy (-O-CH ₂ -O-) and 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), which radicals in turn have one or more substituents may carry a plurality of identical or different substituents independently selected from fluoro, chloro, methyl, ethyl, n -propyl, i -propyl and trifluoromethyl.

According to a particular embodiment of the invention, Y is phenyl which contains one, two or three substituents in the 2, 4 and / or 6-position which are independent are selected from the L recited herein as preferred, especially independently selected from fluoro and chloro.

According to a further embodiment of the invention, Y is 2,4-, 2,5- or 2,6-disubstituted phenyl, 2-substituted phenyl or 2,4,6-trisubstituted phenyl, having substituents L which are independently selected from the group Fluorine, chlorine, bromine, cyano, nitro, OH, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and carboxymethyl.

According to a further embodiment of the invention, Y is 2-trifluoromethylphenyl, 2-chloro-5-nitrophenyl or 2-chloro-4-methoxyphenyl.

Unless otherwise indicated, L is preferably each independently selected from the preferred meanings given herein for L, and it may further be preferred that L is selected from halo, nitro, cyano, Ci-C ₄ -AlkVl, d-C4 haloalkyl, in particular Ci-C2-fluoroalkyl, -C ₄ -alkoxy, d-C4-alkoxycarbonyl, alkylaminocarbonyl, _{Ci-C4-alkylaminocarbonyl} and _{di-Ci-C4-alkylaminocarbonyl,} more preferably selected from nitro, cyano, fluorine, chlorine , Bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy, methoxycarbonyl and aminocarbonyl. Preferred L in the ortho position are fluorine, chlorine, bromine, C 1 -C ₄ -alkyl, in particular methyl or ethyl, C 1 -C ₂ -fluoroalkyl, such as trifluoromethyl, and C 1 -C ₄ -alkoxy, in particular methoxy or ethoxy.

Further preferably, the substituents L, which are optionally bonded to Y = heterocyclyl, in particular to heteroaryl, as explained above, or phenyl, independently of one another are

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; - in each case straight-chain or branched C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl or C 1 -C 6 -alkylsulfonyl; in each case straight-chain or branched C 2 -C 6 -alkenyl or C 2 -C 6 -alkenyloxy; in each case straight-chain or branched C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkylsulfinyl or C 1 -C 6 -haloalkylsulfonyl, each of which contains 1 to 13 identical or different halogen atoms; in each case straight-chain or branched C 2 -C 6 -haloalkenyl or C 2 -C 6 -haloalkenyloxy, which contain in each case 1 to 13 identical or different halogen atoms; - in each case straight-chain or branched C 2 -C 6 -haloalkenyl or C 2 -C 6 -haloalkenyloxyoff atoms, which contain in each case 1 to 11 identical or different halogen atoms; respectively straight-chain or branched Ci-C6-alkylamino, Ci-C6-dialkylamino, d- Cβ-alkylcarbonyl, Ci-Cβ-alkylcarbonyloxy, Ci-C ₆ alkoxycarbonyl, CrC ₆ - alkylsulfonyloxy, hydroxyimino-Ci-C6-alkyl or C C6-alkoxyimino-Ci-C6 alkyl; Cs-Cs-cycloalkyl, preferably _C3-C6 cycloalkyl; - 1,3-linked 1,3-propanediyl, 1,4-butanediyl, methylenedioxy

(-O-CH ₂ -O-) or 1, 2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), where these radicals may be mono- or polysubstituted by identical or different substituents by halogen, - Ci-C4 -Alkyl and / or Ci-C4-haloalkyl containing 1 to 9 identical or different halogen atoms.

According to a further embodiment of the invention, Y is C ₁ -C 10 -alkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -alkynyl, C ₃ -C 10 -cycloalkyl or C ₃ -C 10 -cycloalkenyl, where these radicals are one, two, three or four identical or different group R ^a and / or two substituents bonded to the same or adjacent atoms or ring atoms may be C ₁ -C 6 -alkylene, oxy-C ₂ -C 4 -alkylene or oxy-C ₁ -C 3 -alkyleneoxy as defined herein.

In one embodiment of this embodiment, Y is a C ₁ -C 10 -alkyl, C ₂ -C 10 -alkenyl or C ₂ -C 10 -alkynyl group which may each carry one, two, three or four identical or different groups R ^a . According to one embodiment of the invention, such a group is represented by a five-, six-, seven-, eight-, nine- or ten-membered saturated, in particular five- or six-membered, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms - me from the group O, N and S, substituted.

According to a further embodiment, Y is C ₁ -C 10 -alkyl, preferably C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl. Y may each carry one, two, three or four identical or different groups R ^a , wherein R ^{a is} as defined herein and is preferably each independently selected from: halo, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, d-Ce haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ -

Alkylthio, Ci-C ₆ haloalkylthio, Ci-C ₆ alkylsulfinyl, Ci-C ₆ haloalkylsulfinyl, Ci-C ₆ - alkylsulfonyl, Ci-C ₆ haloalkylsulfonyl, Ci-C ₆ -alkylamino, di-Ci-C ₆ Alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -alkynyloxy and oxy-C ₁ -C ₄ -alkylenoxy. In particular, R ^a is selected from halogen, cyano, Ci-C4-alkyl, _{Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl,} Ci-C ₄ alkoxy, Ci-C ₄ - haloalkoxy, C ₃ - C ₆ cycloalkyl, _C3-C6 halocycloalkyl, and -Si (Ci-C ₆ alkyl). 3 In a specific embodiment thereof, Y is C ₁ -C 10 -haloalkyl, preferably C ₁ -C ₆ -haloalkyl, in particular C ₁ -C ₄ -haloalkyl, which in each case contains one to five halogen atoms selected from fluorine, chlorine and bromine.

According to a preferred embodiment of the invention, Y is an optionally substituted phenyl-Ci-Cio-alkyl group. Another embodiment of alkyl groups in the Y position is the group Vd:

where # denotes the bond to the pyrazolopyrimidine skeleton.

V in the group Vd is, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C ₄ -alkyl, such as CH ₃ , CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CHs) ₂ ; C ₁ -C ₄ -haloalkyl, such as CH ₂ Cl, CH ₂ F, CH ₂ Br, CHCH ₂ , CHF ₂ , CCI ₃ , CF ₃ , CH ₂ CH ₂ Cl, CH ₂ CH ₂ F, CH ₂ CH ₂ Br, CH ₂ CHCl ₂ , CH ₂ CHF ₂ , CH ₂ CCI ₃ , CH ₂ CF ₃ , CCI ₂ CCI ₃ , CF ₂ CF ₃ , CH ₂ CH ₂ CH ₂ Cl, CH ₂ CH ₂ CH ₂ F, CH ₂ CH ₂ CH ₂ Br, CH ₂ CH ₂ CHF ₂ , CH ₂ CH ₂ CHCl ₂ , CF ₂ CF ₂ CF ₃ ,

CH ₂ CH ₂ CHBr ₂ , CH ₂ CH ₂ CCI ₃ , CH ₂ CH ₂ CF ₃ , CCI ₂ CCI ₂ CCI ₃ , CF ₂ CF ₂ CF ₃ , CH (CH ₃ ) CH ₂ Cl, CH (CH ₃ ) CH ₂ F, CH (CH ₃ ) CH ₂ Br; C 1 -C ₄ -alkoxy, such as OCH ₃ ; hydroxy; cyano; substituted C 1 -C ₄ -alkyl, such as CH ₂ OH, CH ₂ CN, CH ₂ OCH ₃ , CH (CN) ₂ , CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CN, CH ₂ CH (CN) ₂ , CH ₂ CH ₂ OH, CH ₂ CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CH ₂ OH, CH ₂ CH ₂ CH ₂ CN, CH ₂ CH ₂ CH (CN) ₂ .

V ² in the group Vd is, for example, hydrogen or methyl, in particular hydrogen.

V ³ in the group Vd is, for example, C ₃ -C 6 -alkyl, such as CH (CH ₃ ) ₂ ,

CH ₂ CH ₂ CH ₂ CH _3, CH (CH ₃₎ CH ₂ CH _3, CH ₂ CH (CHs) _2, C (CHs) _3, CH ₂ CH ₂ CH ₂ CH ₂ CH _3, CH (CH) CH ₂ CH ₂ CH ₃ , CH ₂ CH (CHs) CH ₂ CH ₃ , CH ₂ CH ₂ CH (CHS) ₂ , CH (CH ₃ ) CH (CHS) ₂ , CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CHS, CH (CH ₃ ) CH ₂ CH ₂ CH ₂ CHS, CH ₂ CH (CH ₃ ) CH ₂ CH ₂ CHS, CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CHS, CH (CH ₃ ) CH (CHS) CH ₂ CH ₃ , CH ₂ CH (CH ₂ CHS) ₂ ; C ₃ -C ₄ -haloalkyl such as CH (CH ₃ ) ₂ CHCl ₂ , CH (CH ₃ ) CHF ₂ , CH (CH ₃ ) CHBr ₂ , CH (CH ₃ ) CCI ₃ ,

CH (CH ₃₎ CF _3, CCI (CCIs) _2, CF (CFs) _2; substituted C ₃ -C ₄ -alkyl, such as CH (CH ₃ ) CH ₂ OH, CH (CH ₃ ) CH ₂ OCH, CH (CH ₃ ) CH ₂ CN, CH (CH ₃ ) CH (CN) ₂ , CH ( CH ₂ OH) ₂ , CH (CH ₂ OCHs) ₂ , CH (CH ₂ CN) ₂ or one of the groups mentioned above at V ¹ .

According to a specific embodiment of this embodiment, Y is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, chloromethyl, trifluoromethyl or trifluoroisopropyl.

In another embodiment, Y is not unsubstituted alkyl or CF ₃ , in another embodiment Y is neither R ^a substituted nor unsubstituted alkyl.

According to a further embodiment, Y is (C ₂ -Cio) alkenyl, preferably (C ₂ - Ce) alkenyl, in particular C ₂ -C ₄ -alkenyl. Y may each carry one, two, three or four identical or different groups R ^a , wherein R ^{a is} as defined herein and is preferably each independently selected from: halogen, cyano, nitro, hydroxy, d Ce-alkyl, d-Ce-haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ alkylthio, d-Ce-haloalkylthio, Ci-C ₆ - alkylsulfinyl, Ci-C ₆ haloalkylsulfinyl, Ci-Cβ alkylsulfonyl, Ci-Cβ-haloalkylsulfonyl, Ci-Cβ alkylamino, di-Ci-C6-Alkylmino, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -alkynyloxy and oxy-C ₁ -C ₄ -alkylenepoxy. In particular, R ^{a is} selected from: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 4 -alkyl, C6-cycloalkyl, Cs-Cβ-halocycloalkyl and -Si (Ci-C6-alkyl) 3. In a particular embodiment thereof YC is ₂ -Cio-haloalkenyl, C ₂ -C 6 haloalkenyl preferably, especially C3-C4-haloalkenyl, each containing from one to five, in particular one to three halogen atoms selected from fluorine, chlorine and bromine.

Preferred embodiments for alkenyl groups in position Y are the groups V.a

wherein # denotes the bond to the pyrazolopyrimidine skeleton and

V ^1, V ² is hydrogen, halogen, _{Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-cyanoalkyl,}

C 1 -C 4 -hydroxyalkyl I; V ³ , V ⁴ C5-C8-alkyl or one of the groups mentioned at V ¹ mean.

V ¹ and V ² independently represent, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C ₄ -alkyl, such as CH ₃ , CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) ₂ ; C ₁ -C ₄ -haloalkyl, such as CH ₂ Cl, CH ₂ F, CH ₂ Br, CHCH ₂ , CHF ₂ , CCI ₃ , CF ₃ , CH ₂ CH ₂ Cl, CH ₂ CH ₂ F, CH ₂ CH ₂ Br, CH ₂ CHCl ₂ , CH ₂ CHF ₂ , CH ₂ CHBr ₂ , CH ₂ CCI ₃ , CH ₂ CF ₃ , CCI ₂ CCI ₃ , CF ₂ CF ₃ , CH ₂ CH ₂ CH ₂ Cl, CH ₂ CH ₂ CH ₂ F, CH ₂ CH ₂ CH ₂ Br, CH ₂ CH ₂ CHF ₂ , CH ₂ CH ₂ CHCl ₂ , CF ₂ CF ₂ CF ₃ , CH ₂ CH ₂ CHBr ₂ , CH ₂ CH ₂ CCI ₃ , CH ₂ CH ₂ CF ₃ , CCI ₂ CCI ₂ CCI ₃ , CF ₂ CF ₂ CF ₃ , CH (CH ₃ ) CH ₂ Cl, CH (CH ₃ ) CH ₂ F, CH (CH ₃ ) CH ₂ Br, CH (CH ₃ ) CHCl ₂ , CH ( CH ₃₎ CHF _2, CH (CH ₃₎ CHBr _2, CH (CH ₃₎ CCI _3, CH (CH ₃₎ CF _3, CCI (CCb) _2, CF (CF _{3) 2;} C 1 -C ₄ -alkoxy, such as OCH ₃ ; hydroxy; cyano; substituted C 1 -C ₄ -alkyl, such as CH ₂ OH, CH ₂ CN, CH ₂ OCH ₃ , CH (CN) ₂ , CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CN, CH ₂ CH (CN) ₂ , CH ₂ CH ₂ OH, CH ₂ CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CH ₂ OH, CH ₂ CH ₂ CH ₂ CN, CH ₂ CH ₂ CH (CN) ₂ , CH (CH ₃ ) CH ₂ OH,

CH (CH ₃ ) CH ₂ OCH ₃ , CH (CH ₃ ) CH ₂ CN, CH (CH ₃ ) CH (CN) ₂ , CH (CH ₂ OH) ₂ , CH (CH ₂ OCHs) ₂ , CH (CH ₂ CN) ₂ ;

V ³ and V ⁴ independently of one another are, for example, C ₄ -C 6 -alkyl, such as CH ₂ CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH (CHs) ₂ , C (CH) ₃ , CH ₂ CH ₂ CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) CH ₂ CH ₂ CH ₃ , CH ₂ CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH ₂ CH (CHS) ₂ , CH (CH ₃ ) CH ( CHS) ₂ , CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CHS, CH (CH ₃ ) CH ₂ CH ₂ CH ₂ CHS, CH ₂ CH (CH ₃ ) CH ₂ CH ₂ CHS, CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CHS, CH (CH ₃ ) CH (CHS) CH ₂ CH ₃ , CH ₂ CH (CH ₂ CHS) ₂ or one of the groups mentioned above at V. According to a specific embodiment of this embodiment, Y represents allyl, but-2-en-1-yl or trichloroallyl.

According to another preferred embodiment, Y is (C 2 -C 10) -alkynyl, preferably (C 2 -C 6) -alkynyl. Y may each carry one, two, three or four identical or different groups R ^a , wherein R ^{a is} as defined herein and is preferably each independently selected from: halogen, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, Cr _{C4-alkoxy-Ci-C 4} alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ -halocycloalkyl, Ci-C ₄ -alkoxy -C ₄ - haloalkoxy and -Si (Ci-C6 alkyl) 3 ,

A preferred embodiment for alkynyl groups in the Y position is the group V.c:

wherein # denotes the bond to the pyrazolopyrimidine skeleton and V ¹ , V ² and V ^{3 have} the meanings given above.

V ¹ and V ² independently of one another in the group Vc represent, for example, hydrogen, halogen, such as fluorine, chlorine, bromine; C 1 -C ₄ -alkyl, such as CH ₃ , CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CHs) ₂ ; Halomethyl such as CH ₂ Cl, CH ₂ F, CH ₂ Br, CHCH ₂ , CHF ₂ , CCI ₃ , CF ₃ ; CrC ₄ alkoxy, such as OCH ₃ ; hydroxy; cyano; substituted CrC ₂ alkyl such as CH ₂ OH, CH ₂ CN, CH ₂ OCH ₃ , CH (CN) ₂ , CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ CN, CH ₂ CH (CN) ₂ , CH ₂ CH ₂ OH.

V ³ in the group Vc is, for example, branched C ₄ -C 6 -alkyl, such as CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH (CH ₂ ) ₂ , C (CH ₃ ) ₃ , CH (CH ₃ ) CH ₂ CH ₂ CHs, CH ₂ CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH ₂ CH (CHs) ₂ , CH (CH ₃ ) CH (CHs) ₂ , CH (CH ₃ ) CH ₂ CH ₂ CH ₂ CHS, CH ₂ CH (CH ₃ ) CH ₂ CH ₂ CHS, CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CHS, CH (CH ₃ ) CH (CHS) CH ₂ CH ₃ , CH ₂ CH (CH ₂ CHs) ₂ or one of above mentioned groups at V ¹ .

According to a further preferred embodiment of the invention, Y is optionally substituted by R ^a , as defined herein, substituted C ₃ -Cio-cycloalkyl, preferably optionally substituted Cs-Cs-cycloalkyl, in particular C ₃ -C 7 -cycloalkyl. Y may here in each case carry one, two, three or four identical or different groups R ^a , where R ^{a is} as defined herein and is preferably each independently selected from: halogen, cyano, nitro, hydroxy, C 1 -C ₆ -alkyl, -haloalkyl, C ₃ -C ₆ cycloalkyl, -C ₆ alkoxy, -C ₆ - haloalkoxy, -C ₆ -alkylthio, -C ₆ haloalkylthio, CRCE alkylsulfinyl, CrC ₆ - haloalkylsulfinyl, d-Ce-alkylsulfonyl, haloalkylsulfonyl CRCE , -C ₆ alkylamino, di-CrC ₆ alkylamino, C ₂ -C ₆ -alkenyl -alkyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ -alkyl kinyl, C ₂ -C ₆ -alkyl and oxy kinyloxy CrC ₄ -alkyleneoxy. In particular, R ^a is selected here from: halogen, cyano, -C ₄ -alkyl, -C ₄ haloalkyl, _{Ci-C4-alkoxy-CrC 4} alkyl, -C ₄ alkoxy, -C ₄ - haloalkoxy, C ₃ -C ₆ - Cycloalkyl, Cs-C ₆ halocycloalkyl and -Si (C ₁ -C ₆ -alkyl) ₃ . In a specific embodiment thereof, Y is Cs-Cs-halocycloalkyl, preferred Example, C ₃ -C6-Halogencycloalkyl, each containing one to three halogen atoms independently selected from fluorine, chlorine and bromine. In a further specific embodiment thereof, Y is C ₃ -C 8 -cycloalkyl which is substituted by one, two or three methyl groups, preferably C ₃ -C 6 -cycloalkyl.

Preferred embodiments of cycloalkyl groups in the Y position are the groups

wherein # denotes the bond to the pyrazolopyrimidine skeleton and V ¹ , V ² and V ^{3 have} the meanings given above.

V ¹ in group Ve represents, for example, hydrogen or methyl;

V ² and V ³ in group Ve independently of one another denote, for example, hydrogen; cyano; Halogen, such as chlorine or bromine; C 1 -C 3 -alkyl, such as CH 3, CH 2 CH 3; CrC ₃ - alkoxy, such as OCH ₃ ; Halomethyl such as CH ₂ Cl, CH ₂ F, CH ₂ Br, CHCH ₂ , CHF ₂ , CCI ₃ , CF ₃ .

In one embodiment of group Ve, V ² and V ^{3 are the} same.

V and V ² in the groups Vf, Vg and Vh are preferably hydrogen.

In a specific embodiment of this embodiment, Y is cyclopropyl, cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl or 2,2-dichlorocyclopropyl.

Preferred embodiments of compounds of the formula I correspond to the formulas 1.1 to 1.8, where the variables in each case have the meanings or preferred meanings defined herein:

According to another preferred embodiment, Y is an unsubstituted or substituted by R ^a, as defined above, substituted C3-Cio-cycloalkenyl, preferably C ₃ - Cs-cycloalkenyl, in particular C5-C7-cycloalkenyl group. Y may in each case carry one, two, three or four identical or different groups R ^a , where R ^{a is} as defined herein and is preferably each independently selected from halogen, cyano, nitro, hydroxy, C ₁ -C ₆ -alkyl, d-Ce-haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ - haloalkoxy, Ci-C ₆ alkylthio, Ci-C ₆ haloalkylthio, Ci-C ₆ alkylsulfinyl, CrC ₆ - haloalkylsulfinyl, Ci-C ₆ alkylsulfonyl, Ci-C ₆ haloalkylsulfonyl, Ci-C ₆ -alkylamino, di-Ci-C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkenyloxy, C -Al ₂ -C ₆ kinyl, C ₂ -C ₆ -alkyl kinyloxy and oxy-Ci-C4-alkyleneoxy. In particular, R ^a is selected here from: halogen, cyano, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy,} CrC ₄ - haloalkoxy, _C3-C6 cycloalkyl, _C3-C6 halocycloalkyl, and -Si (Ci-C ₆ alkyl) 3, especially halogen and Ci-C ₄ alkyl. In a particular embodiment thereof Y C3-C means ₆ halocycloalkenyl, containing one, two or three halogen atoms independently selected from fluorine, chlorine and bromine. In another particular embodiment thereof Y by one, two or three methyl groups substituted Cs-Cs-cycloalkenyl, preferably C3-C ₆ -alkenyl means -Cycloal.

According to a specific embodiment, the cycloalkenyl group preferably has one or two double bonds. Examples of cycloalkenyl groups as substituent Y are cyclopent-1-en-1-yl, cyclohex-1-en-1-yl, which may be substituted according to the invention by R ^a , as defined above.

In a specific embodiment of this embodiment, Y is cyclopentylbenzene, 2-methylcyclopentenyl, 2-chlorocyclopentenyl, cyclohexenyl, 2-methylcyclohexenyl, 2-chlorocyclohexenyl or dichlorocyclohexenyl.

In the compounds of the formula I, Z is NR ³ R ⁴ .

In one embodiment of the invention thereby, R ³ represents Ci -Ce-Al kyl, halo-dC ₈ alkyl, C ₂ -C ₈ -alkenyl -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl kinyl, C ₃ -C ₈ haloalkynyl, C ₃ -C ₈ - cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₃ -C ₈ cycloalkyl-Ci-C ₈ alkyl, C ₆ -C ₄ aryl, C ₆ - Ci ₄ - aryl-Ci-C ₈ alkyl, five- or six-membered heteroaryl or five- or six-membered heteroaryl-Ci-C ₈ alkyl. In another embodiment, R ^{4 is} hydrogen, amino, C 1 -C ₈ -alkylamino, di-C 1 -C ₈ -alkylamino or one of the groups mentioned in R ³ . The alkyl, alkenyl, alkynyl and cycloalkyl groups in R ³ and / or R ⁴ may in turn carry one, two or three identical or different groups R ^a , wherein R ^a is independently selected from halogen, cyano, C 1 -C ₈ Alkoxy, C 1 -C ₈ -alkyl, d- C 1 -haloalkoxy, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, tri-C 1 -C 6 -alkylsilyl, C 1 -C 8 -alkylamino and C 1 -C -alkylamino.

In one embodiment of this embodiment, R ^{3 is} C ₁ -C 6 -alkyl, C ₁ -C 6 -haloalkyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -haloalkenyl, C ₃ -C 8 -cycloalkyl, C ₁ -C 5 -halocycloalkyl or C ₃ -C 8 -cycloalkyl-C ₁ -C 8 -alkyl. According to another embodiment, R ^{4 is} hydrogen, or one of the groups mentioned in R ³ .

In a further embodiment of the invention, Z is a group selected from (±) NHCH (CH ₃ ) CH (CHS) ₂ , (R) NHCH (CH ₃ ) CH (CHS) ₂ , (S) NHCH (CH ₃ ) CH (CHS) ₂ , (±) NHCH (CH ₃ ) C (CHS) ₃ , (R) NHCH (CH ₃ ) C (CH ₃ ) ₃ , (S) NHCH (CH ₃ ) C (CHS) ₃ , (± ) NHCH (CH ₂ S) CH ₂ CH ₃ , (R) NHCH (CH ₂ S) CH ₂ CH ₃ , (S) NHCH (CH ₂ S) CH ₂ CH ₃ , (±) NHCH (CH ₂ S) CH ₂ CF ₃ , (R) NHCH (CHS) CH ₂ CF ₃ and (S) NHCH (CHS) CH ₂ CF ₃ .

In a further embodiment, neither R ³ nor R ^{4 is} hydrogen, where R ³ and R ^{4 are} preferably selected independently of one another from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ C6-haloalkenyl, Cs-Cβ cycloalkyl, and C ₃ -C ₆ halo-cycloalkyl, especially selected from Ci-C ₆ alkyl, and Ci-C ₆ haloalkyl.

In yet another embodiment, R ^{3 is} as previously defined or preferably defined and R ⁴ is hydrogen.

When R ³ and R ⁴ bear identical or different groups R ^a , R ^{a is in} each case as defined above and preferably in each case independently halogen, cyano, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, C 1 -C ₄ -alkoxy or C 1 -C ₄ -haloalkoxy.

According to a further embodiment of the invention, R ^{3 is} straight-chain or branched, unsubstituted or substituted C ₁ -C 8 -alkyl, C ₁ -C 8 -haloalkyl, C ₂ -C 5 -alkenyl, C ₂ -C -alkynyl, C ₁ -C 8 -cycloalkyl, unsubstituted or substituted phenyl or naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.

According to one embodiment of the invention, R ^a when attached to R ³ and / or R ⁴ is independently halogen, cyano, nitro, carboxyl, C ₁ -C 8 alkyl, C ₁ -C 8 haloalkyl, C ₂ -C 5 -alkyl kenyl, C ₂ -Cs -haloalkenyl, C ₂ -Cs-alkynyl, Cs-Cs-haloalkynyl, C ₁ -C 10 -alkadienyl, C 5 -C 8 -cycloalkyl, C ₃ -C 8 -halocycloalkyl, Cs-Cs-cyclo- alkenyl, Cs-Cio-bicycloalkyl, C 1 -C 8 -alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothio-carbonyl, C ₁ -C ₆ -alkylene, -C (OO) -A, -C (OO) -OA, -C (= O) -N (A ') A, C (A') (= N-OA), N (A ') A, N (A') -C (= O) -A, N (A ") -C (= O) -N (A ') A, S (= O) _m -A, S (= O) _m -OA, S (= O) _m -N (A') A, -Si (C ₁ -C ₆ -alkyl) ₃ , phenyl, naphthyl, five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S; where m, A, A 'and A "are as defined above

R ³ is in particular Ci -C ₆ -alkyl, C ₂ -C ₆ -alkenyl -alkyl, C ₂ -C ₆ -alkyl kinyl, C ₃ -C ₆ -cycloalkyl, these radicals being 1, 2, 3, 4 or 5-fold may be substituted by halogen, Ci-C ₆ alkyl or CrC ₆ - haloalkyl.

In specific embodiments of the present invention, as component 1)

Compounds of the formula I used in which R ^{3 is} a group B:

wherein

Z ^{1 is} hydrogen, fluorine or C ¹ -C ⁴ -fluoroalkyl, Z ^{2 is} hydrogen or fluorine, or Z ¹ and Z ² together form a double bond; q is 0 or 1; and

R ^{14 is} hydrogen or methyl. According to a specific embodiment of this embodiment, R ^{4 is} hydrogen.

In a further embodiment of the invention, R ⁴ in the compounds of the formula I is hydrogen and R ³ is C ³ -C ₆ -cycloalkyl which may be substituted by C ₁ -C ₄ -alkyl.

In another embodiment of the invention, R ^{3 is} selected from: methyl, ethyl, CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH (CHs) ₂ , CH (CH ₃ ) CH (CHs) ₂ , CH (CH ₃ ) C (CHs) ₃ , CH (CH ₃ ) CF ₃ , CH (CH ₃ ) CCI ₃ , CH ₂ CF ₂ CF ₃ , CH ₂ C (CHs) = CH ₂ , CH ₂ CH = CH ₂ , cyclopentyl, cyclohexyl, benzyl; and R ⁴ is hydrogen or methyl; or R ³ and R ⁴ together are - (CH ₂ ) ₂ CH (CH ₃ ) (CH ₂ ) ₂ -, - (CH ₂ ) ₂ CH (CF ₃ ) (CH ₂ ) ₂ - or - (CH ₂ ) ₂ O (CH ₂ ) ₂ -.

According to another embodiment of the invention, R ^{3 is} selected from: CH (CH ₃ ) CH (CHs) ₂ , CH (CH ₃ ) C (CHs) ₃ , CH ₂ CF ₃ , CH (CH ₃ ) CF ₃ , CH ₂ CH ₂ CN, CH ₂ CH ₂ CH _3, CH (CH ₃₎ CH ₂ CH _3, CH (CH ₃₎ CH ₂ CH (CHs) _2, CH ₂ CH ₂ OCH _3, cyclo-C ₃ H _5, CH ₂ C (CHS) ₂ OCH ₃ , CH (CHS) C (CHS) ₂ OCHS, CH (CHS) CH (CH ₃ ) OCHS, CH ₂ CH (CHS) ₂ , CH ₂ C (CHs) ₃ , CH ₂ -cyclo- CsH _5, cyclo-C ₆ H n, CH (CHs) _2, CH (CH ₃₎ -cyclo-C ₃ H _5, CH ₂ C (CHs) = CH _2, CH ₂ CH = CH _2, CH ₂ C = CH , CH ₂ C = C-CH ₃ or cyclo-C ₅ H ₉ , where R ^{4 is} hydrogen according to one embodiment of the invention, according to another embodiment, Ci-C4-alkyl, in particular methyl, ethyl or propyl means.

According to further embodiments of the invention, R ^{3 has} one of the following meanings: R ³ is C 1 -C 6 -haloalkyl (having one to five identical or different halogen atoms) or C 1 -C 6 -alkyl which has one to five halogen, cyano, hydroxyl, C 1 -C 4 -alkoxy, C 5 -C 6 -alkyl radicals. May carry cycloalkyl, SH, Ci-C4-alkylthio, amino, Ci-C4-alkylamino and / or di-Ci-C4-alkylamino groups; or

R ³ is C 2 -C 8 haloalkenyl (having one to three same or different halogen atoms) or C 2 -C 8 alkenyl which is one to three halo, cyano, hydroxy, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl -, SH, Ci-C4-alkylthio, amino, Ci-C4-alkylamino and / or di-Ci-C4-alkylamino groups can carry; or

R ³ is Cs-Cs haloalkynyl (having one to three same or different halogen atoms) or C 2 -C 8 alkynyl which is one to three halo, cyano, hydroxy, C 1 -C 4 alkoxy, Cs-Cβ cycloalkyl -, SH, Ci-C4-alkylthio, amino, Ci-C4-alkylamino and / or di-Ci-C4-alkylamino groups can carry; or

R ³ is C3-C8-halocycloalkyl (with one to three same or different halogen atoms), or Cs-Cs-cycloalkyl which may carry from one to three halogen and / or C1-C4 alkyl groups; or

R ³ is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which is unsubstituted or substituted by one to four halogen, d-C _4- alkyl, cyano, nitro, hydroxy, C ₃ -C ₆ -cycloalkyl, Ci-C ₄ -alkoxy and / or SH groups.

R ⁴ in these cases according to one embodiment of the invention hydrogen, according to another embodiment, Ci-Cβ-alkyl.

According to a further embodiment, R ³ and R ⁴ together with the nitrogen atom to which they are attached form a five- or six-membered saturated or partially unsaturated heterocycle containing one or two further heteroatoms from the group O, N and S as ring members may contain, wherein the heterocycle may carry one, two or three identical or different groups R ^a , as defined above. Preferably ^, each R ^a is independently selected from halo, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy. Further preferably, R ^a is independently selected from d-Cs-alkyl and d-Cs-haloalkyl.

According to one embodiment of this embodiment of the invention, R ³ and R ⁴ together with the nitrogen atom to which they are attached form an unsubstituted or substituted by one, two or three identical or different fluorine, methyl and / or trifluoromethyl groups pyrrolidinyl, piperidinyl , Morpholinyl, thio morpholinyl, piperazinyl, 3,6-dihydro-1 (2H) pyridinyl or teterahydro-1 (2H) -pyridazinyl ring.

According to a further embodiment of this embodiment of the invention, R ³ and R ⁴ together form -N (R ') (CH 2) 4, where zero, one, two or three hydrogen atoms are replaced by identical or different groups R ", where R" is independently R ausgewählt is selected from methyl, ethyl, fluoro, chloro and trifluoromethyl, and wherein R 'is hydrogen or methyl; or R ³ and R ⁴ together form -NH (CH 2) 3, where zero, one, two or three hydrogen atoms are replaced by identical or different groups R '', where R '''is independently selected from methyl, ethyl, fluoro, Chlorine and trifluoromethyl.

According to a further embodiment of this embodiment of the invention, R ³ and R ⁴ together with the nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thiomorpholinyl ring which is optionally substituted by one, two or three identical or different groups R ^a , especially a piperidinyl ring.

In particular, the heterocycle formed is unsubstituted or substituted by one, two or three R ^a , wherein each R ^a is independently selected from halo, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl. Of these, particular preference is given to compounds I in which R ³ and R ⁴ together with the nitrogen atom to which they are attached are a 4-methylpiperidine ring, a 4-trifluoromethylpiperidine ring, a morpholine ring or a 3,4-dimethylpiperidine ring and especially a 4-methylpiperidine ring or form a 3,4-dimethylpiperidine ring.

According to another aspect of the invention, R ³ and R ⁴ together with the nitrogen atom to which they are attached form a 5- or 6-membered heteroaryl which may be unsubstituted or substituted, preferably by 1, 2 or 3 groups R ^a . In particular, the group NR ³ R ⁴ then forms a pyrazole ring which is optionally substituted in the manner described above and especially by 1 or 2 of the following radicals: halogen, C 1 -C ₄ -alkyl or C 1 -C ₄ -haloalkyl, in particular by 2 methyl groups or two Trifluoromethyl groups in the 3,5-position.

According to one embodiment of the compositions according to the invention, these contain at least one compound of the formula 1-1.1, as shown below.

According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula 1-1.2, as shown below.

According to a further embodiment of the compositions according to the invention, these comprise at least one compound of the formula I.2.1, as shown below. According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula I.2.2, as shown below.

According to a further embodiment of the compositions according to the invention, these comprise at least one compound of the formula 1-3.1, as shown below.

According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula I-3.2, as shown below.

According to a further embodiment of the compositions according to the invention, these comprise at least one compound of the formula 1-4.1, as shown below.

According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula I-4.2, as shown below.

According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula 1-5.1, as shown below.

According to a further embodiment of the compositions according to the invention, these comprise at least one compound of the formula I-5.2, as shown below.

In formulas 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 and I-5.2, "Ph" is phenyl which is substituted by one, two, three, four or five identical or different substituents L, "Het" in each case represents an unsubstituted or a five- or six-membered heteroaryl radical which is substituted by one, two, three or four identical or different L groups, as defined elsewhere herein, and the meanings of the variables L, Z and R ¹ are each independently as defined elsewhere herein or as preferred.

1-1 .1 1-2.1 1-3.1 | -4.1 " ⁶¹ cN

1-1.2 I-2.2 1-3.2 1-4.2

1-5.1 I-5.2

In particular, the compounds I compiled in Tables 1 to 257 below are preferably used in the compositions according to the invention. Regardless of the combination in which they are mentioned, the groups mentioned in the tables for a substituent also individually represent a particularly preferred embodiment of the relevant substituent for a compound of the formula I.

Ia.1 la.2 la.3 la.4

la.5 la.6 la.7 la.8

la.13 Ia ₁₄

Table 1

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, la.13 and Ia.14, in which Y is 2-pyridinyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 2

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, la.13 and Ia.14, in which Y is 5-cyanopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 3

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is 5-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 4

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 5

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 6

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 6-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 7

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 5-trifluoromethylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 8

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-trifluoromethylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 9

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 10 Compounds of the formula Ia.1, la. 2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 3-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 1 1

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-difluoropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 12

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dichloropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 13

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is pyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 14

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 15

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyrazine-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 16

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyridazin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 17

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 6-chloropyridazin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 18 Compounds of the formula Ia.1, la. 2, la.3, la.4, la.5, la.6, la.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14 in which Y is 1, 3,5-triazin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 19

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyrimidin-2-yl and the combination of

Z and R ¹ for a compound in each case one row of Table B corresponds to Table 20

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 21

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pyrimidin-5-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 22

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-6-trifluoromethylpyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 23

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 6-trifluoromethylpyrimidin-4-yl and the Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 24

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-methyl-6-trifluoromethylpyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 25

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-chloro-6-methylpyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 26

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 5-bromo-6-methylpyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 27

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-fluoro-6-methylpyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 28

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-chloropyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 29

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-fluoropyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 30

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-bromopyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 31

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-5-fluoropyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 32

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-5-chloropyrimidin-4-yl and the Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 33

Compounds of the formula Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-5-bromopyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 34

Compounds of the formula Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 5-fluoro-6-fluoromethylpyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 35

Compounds of the formulas Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 5,6-dimethylpyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 36

Compounds of the formula Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2,5-dimethylpyrimidin-4-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 37

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4,6-dimethylpyrimidin-2-yl and the

Combination of Z and R ¹ for a compound of one row of Table B corresponds to Table 38

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-methylpyrimidin-5-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 39

Compounds of the formulas Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.10, Ia.1, Ia.10, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,6-dimethylpyrimidin-5-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 40

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 4-trifluoromethyl-6-methyl-pyrimidin-5-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 41

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 42

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-bromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 43 Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-chloropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 44

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-bromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 45

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-chloropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 46

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-bromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 47

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 48

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-cyanopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 49

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 50

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-bromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 51

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 52

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-cyanopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 53

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methyl-5-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 54

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methyl-5-chloropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 55

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methyl-5-bromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 56

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dimethylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 57

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methyl-5-cyanopyridin-2-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 58

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 3-bromo-5-fluoropyridin-2-yl and the grain bination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 59

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-bromo-5-chloropyridin-2-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 60

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-bromo-5-methylpyridin-2-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 61

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dibromopyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 62

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoropyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 63

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloropyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 64

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-bromopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 65 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 3-methylpyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 66

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-difluoropyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 67

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-chloropyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 68

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-bromopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 69

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-fluoro-5-methylpyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 70

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-fluoro-5-cyanopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 71

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-bromopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 72

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-methylpyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 73

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloro-5-ethylpyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 74

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-chloro-5-cyanopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 75

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3,5-dimethylpyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 76

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-methyl-5-bromopyridin-4-yl and the Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 77

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-methyl-5-cyanopyridin-4-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 78

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 79

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 80

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-bromopyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 81

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 82 Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11,

Ia.12, Ia.13 and Ia.14, in which Y is 4-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 83

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 84

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4-bromopyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 85

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 86

Compounds of the formulas Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12, Ia.13 and Ia.14, in which Y is 2,4-difluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 87

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-fluoro-4-chloropyridin-3-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 88

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-fluoro-4-bromopyridin-3-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 89

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-fluoro-4-methylpyridin-3-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 90

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-dichloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 91

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 92

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-bromopyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 93

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 94

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,4-dimethylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 95

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is 2-methyl-4-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 96 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methyl-4-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 97 Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methyl-4-bromopyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 98 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-bromo-4-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 99 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-bromo-4-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 100 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-bromo-4-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 101 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,6-difluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 102

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-fluoro-6-chloropyridin-3-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 103

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-fluoro-6-bromopyridin-3-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 104

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-fluoro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 105

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-fluoro-6-cyanopyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 106

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-fluoro-6-methylcarbamoylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 107

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4,6-dichloropyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 108

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 4-chloro-6-fluoropyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 109

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-chloro-6-bromopyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 1 10

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-chloro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 1 11

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-chloro-6-ethylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 1 12

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-chloro-6-methoxypyridin-3-yl and the Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 1 13

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia1.1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-chloro-6-cyanopyridin-3-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 1 14

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-methyl-6-fluoropyridin-3-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 1 15

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4-methyl-6-chloropyridin-3-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 1 16

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4-methyl-6-bromopyridin-3-yl and the

Combination of Z and R ¹ for a compound in each case one row of Table B corresponds to Table 1 17

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4,6-dimethylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 1 18

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11,

Ia.12, Ia.13 and Ia.14, in which Y is 4-methyl-6-cyanopyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 1 19

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11,

Ia.12, Ia.13 and Ia.14, in which Y is 4-bromo-6-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 120

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11,

Ia.12, Ia.13 and Ia.14, in which Y is 4-bromo-6-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 121

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 4-bromo-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 122

Compounds of the formula Ia.1, La.2, Ia.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2,4-dichloro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 123

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dimethylpyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 124

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,4,5-trimethylpyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 125

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dimethyl-4-chloropyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 126

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-chloropyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 127

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methylpyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 128 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 3,5-dichloro-4-methylpyrazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 129 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 3-methyl-4-chloropyrazol-1-yl and the Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 130

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1, 3-dimethylpyrazol-5-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 131

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1-methyl-3-trifluoromethylpyrazol-5-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 132

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1, 5-dimethylpyrazol-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 133

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1, 3,5-trimethylpyrazol-4-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 134

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1-methyl-3-trifluoromethylpyrazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 135

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1, 3-dimethylpyrazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 136

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1-methyl-5-trifluoromethylpyrazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 137

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1, 5-dimethylpyrazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 138

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methylthiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 139

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is thiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 140 Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methyl-5-chlorothiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 141 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,5-dichlorothiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 142

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-5-bromothiazol-4-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 143

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methylisothiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 144

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methyl-5-chloroisothiazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 145

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is isoxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 146

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dimethylisoxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 147

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is 3-chloroisoxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 148

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methylisoxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 149

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is oxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 150

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,5-dimethyloxazol-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 151

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyloxazol-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 152 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,5-dichloroimidazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 153

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4,5-dimethylimidazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 154

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14 in which Y is 3,5-dimethyl-1, 2,4-triazol-1-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 155

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dichloro-1, 2,4-triazol-1-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 156

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dibromo-1, 2,4-triazol-1-yl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 157

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia1.1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-difluoro-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 158

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3,5-ditrifluoromethyl-1,2,4-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table B.

Table 159

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-methyl-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 160

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-chloro-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B.

Table 161

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, La.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-fluoro-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 162

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-bromo-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 163

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3-trifluoromethyl-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 164

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 4,5-dimethyl-1, 2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 165

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is 4,5-dichloro-1,2,3-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B corresponds to

Table 166 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la9, la10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,5-dibromo-1,2,3-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B corresponds to

Table 167 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,5-difluoro-1,2,3-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B corresponds to

Table 168 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la9, la10, la.1,

Ia.12, Ia.13 and Ia.14, in which Y is 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl and the combination of Z and R ¹ for each compound corresponds to one row of Table B corresponds to

Table 169 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-methyl-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 170 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-chloro-1, 2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 171 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-fluoro-1, 2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 172 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-bromo-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 173 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 5-trifluoromethyl-1, 2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 174

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-thienyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 175

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,5-dichlorothiophen-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 176

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3,4,5-trichlorothiophen-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 177

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-chlorothiophen-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 178

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-bromothiophen-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 179

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 5-methylthiophen-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 180 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,5-dichlorothiophen-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 181 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,5-dibromothiophen-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 182 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methylthiophen-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 183

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 1-methyl-5-methoxypyrazol-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 184

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 3-thienyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 185

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 3-methylthien-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 186 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la8, la9, la10, la.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,5-dimethylthien-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 187

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluoro-6-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 188

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 189

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-dichlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 190

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluoro-6-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 191 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,4,6-trifluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 192

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-difluoro-4-methoxyphenyl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 193

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is pentafluorophenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 194

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-4-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 195 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-trifluoromethylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 196

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methoxy-6-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 197

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chlorophenyl and the combination of

Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 198

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 199

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 200

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluoro-4-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 201 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-chloro-4-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 202

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,3-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 203

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14 in which Y is 2,5-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 204

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,3,4-trifluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 205 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 206

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-dimethylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 207

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methyl-4-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 208

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-fluoro-4-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 209

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-dimethylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 210 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2,4,6-trimethylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 211

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-difluoro-4-methylphenyl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 212

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, La.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-trifluoromethyl-4-fluorophenyl and the

Combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 213

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-trifluoromethyl-5-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 214

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-trifluoromethyl-5-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 215

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B Table 216

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-5-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 217 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methyl-5-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 218

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-methoxyphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 219

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-6-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 220

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-dichloro-4-fluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 221

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-dichlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 222

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is 2,3,6-trifluorophenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 223

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4,5-trifluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 224

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,3,4,6-tetrafluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 225

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4,6-trichlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 226

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-4-methylphenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 227

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-dichloro-5-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 228

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2,5-dichlorophenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 229 Compounds of the formula Ia.1, la.2, la .3, la.4, la.5, la.6, la.7, la.8, la.9, la10, la.11,

Ia.12, Ia.13 and Ia.14, in which Y is 2,5-dimethylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 230

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-5-bromophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 231

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-chloro-5-methoxyphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 232

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13 and Ia.14, in which Y is 2-chloro-5-methylphenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 233

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, Ia.9, Ia.10, La.11, Ia.12 , Ia.13 and Ia.14, in which Y is 3,4-methylenedioxyphenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 234

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,4-difluoro-6-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 235

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2,6-difluoro-4-chlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 236

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is phenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 237 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la10, la.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-chloro-5-nitrophenyl and the combination of Z and R ¹ for each compound corresponds to one row of Table B Table 238

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, La.11, Ia.12 , and Ia.13 Ia.14 in which Y represents CH3 and the combination of Z and R ¹ for each compound corresponds to one line of Table B. Table 239

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is C2H5 and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 240

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH (CH 3) 2 and the combination of Z and R ¹ for each compound corresponds to one line of Table B corresponds to Table 241

Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, in which Y is CH (CH ₃ ) (C ₂ H ₅ ) and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 242

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH (C ₂ Hs) ₂ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 243

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH (CH ₃ ) (nC ₃ H ₇ ) and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 244

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH ₂ CF ₃ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 245

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH ₂ (CH ₂ ) βCH ₃ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 246 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is cyclo-CsHg and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 247

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is cyclo-CβHn and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 248

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is cyclo-C7Hi ₃ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 249

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH ₂ CH = C (CH ₃ ) ₂ and the combination of Z and R ¹ for each compound corresponds to one line of Table B Table 250

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH ₂ CH = CH ₂ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 251 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la8, la9, la10, la.1,

Ia.12, Ia.13 and Ia.14, in which Y is CH ₂ C≡CCH ₃ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B. Table 252

Compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y

and the combination of Z and R ¹ for each compound corresponds to one line of Table B corresponds to Table 253

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is 2-methylcyclopent-1-enyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B corresponds to Table 254

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y 1 is methylcyclohexyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 255 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methylcyclohex-1-enyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 256 Compounds of the formulas Ia.1, I.2.1, I.3.10, Ia.1,

Ia.12, Ia.13 and Ia.14, in which Y is 2-methylcyclopentyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table 257

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia. 12, Ia.13 and Ia.14, in which Y is CH (CH ₃ ) (C ₂ H ₅ ) and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table B.

Table B

According to one embodiment of the invention, the compositions according to the invention comprise as component 1) at least one compound of the formula I and at least one active compound selected from the group of A) azoles.

According to one embodiment, the compositions contain at least one compound of the formula 1-1.1 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions comprise at least one compound of the formula 1-1.2 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions comprise at least one compound of the formula I-2.2 and at least one active compound selected from the group of A) azoles. According to a further embodiment, the compositions contain at least one compound of formula 1-3.1 and at least one active ingredient selected from the group of A) azoles.

According to a further embodiment, the compositions contain at least one compound of formula I-3.2 and at least one active ingredient selected from the group of A) azoles.

According to a further embodiment, the compositions of a compound fertil the formula 1-4.1 and at least one active ingredient selected from the group of A) azoles.

According to a further embodiment, the compositions comprise a compound of the formula I-4.2 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions contain a compound of the formula 1-5.1 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions comprise a compound of the formula I-5.2 and at least one active compound selected from the group of A) azoles.

According to a further embodiment, the compositions comprise as component 1) at least one of the compounds of the formula I individualized in Tables 1 to 257 and at least one active compound selected from the group of A) azoles.

According to a further embodiment of the invention, the compositions according to the invention comprise as component 1) at least one compound of the formula I and at least one active compound selected from the group of B) strobilurins.

According to one embodiment, the compositions comprise at least one compound of the formula 1-1.1 and at least one active substance selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain at least one compound of the formula 1-1.2 and at least one active ingredient selected from the group of B) strobilurins. According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active compound selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain at least one compound of the formula I-2.2 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain at least one compound of formula 1-3.1 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain at least one compound of the formula I-3.2 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain a compound of the formula 1-4.1 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain a compound of formula I-4.2 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain a compound of the formula 1-5.1 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain a compound of formula I-5.2 and at least one active ingredient selected from the group of B) strobilurins.

According to a further embodiment, the compositions contain as component 1) at least one of the compounds of the formula I individualized in Tables 1 to 258 and at least one active compound selected from the group of B) strobilurins.

According to a further embodiment of the invention, the compositions according to the invention comprise as component 1) at least one compound of the formula I and at least one active compound selected from the group of C) carboxylic acid amides. According to one embodiment, the compositions comprise at least one compound of the formula 1-1.1 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions contain at least one compound of the formula 1-1.2 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions comprise at least one compound of the formula I-2.2 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions comprise at least one compound of the formula 1-3.1 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions contain at least one compound of the formula I-3.2 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions of a compound of the formula contain 1-4.1 and at least one active ingredient selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions comprise a compound of formula I-4.2 and at least one active ingredient selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions of a compound of formula 1-5.1 and at least one active ingredient selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions contain a compound of the formula I-5.2 and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment, the compositions contain as component 1) at least one of the individualized in Tables 1 to 257 compounds of the formula I and at least one active compound selected from the group of C) carboxylic acid amides.

According to a further embodiment of the invention, the compositions according to the invention comprise as component 1) at least one compound of the formula I and at least one active compound selected from the group of the D) heterocyclic compounds.

According to one embodiment, the compositions contain at least one compound of the formula 1-1.1 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions contain at least one compound of the formula 1-1.2 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions comprise at least one compound of the formula I-2.2 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions comprise at least one compound of the formula 1-3.1 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions contain at least one compound of formula I-3.2 and at least one active ingredient selected from the group of D) heterocyclic compounds.

According to a further embodiment, the compositions comprise a compound of the formula 1-4.1 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions comprise a compound of the formula I-4.2 and at least one active compound selected from the group of the D) heterocyclic compounds. According to a further embodiment, the compositions contain a compound of the formula 1-5.1 and at least one active compound selected from the group of D) heterocyclic compounds.

According to a further embodiment, the compositions comprise a compound of the formula I-5.2 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment, the compositions contain as component 1) at least one of the compounds of the formula I individualized in Tables 1 to 257 and at least one active compound selected from the group of the D) heterocyclic compounds.

According to a further embodiment of the invention, the compositions according to the invention comprise as component 1) at least one compound of the formula I and at least one active compound selected from the group of E) carbamates.

According to one embodiment, the compositions contain at least one compound of the formula 1-1.1 and at least one active compound selected from the group of E) carbamates.

According to a further embodiment, the compositions contain at least one compound of formula 1-1.2 and at least one active ingredient selected from the group of E) carbamates.

According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active compound selected from the group of E) carbamates.

According to a further embodiment, the compositions contain at least one compound of the formula I-2.2 and at least one active compound selected from the group of E) carbamates.

According to a further embodiment, the compositions comprise at least one compound of the formula 1-3.1 and at least one active compound selected from the group of E) carbamates.

According to a further embodiment, the compositions contain at least one compound of formula I-3.2 and at least one active ingredient selected from the group of E) carbamates. According to a further embodiment, the compositions contain a compound of the formula 1-4.1 and at least one active compound selected from the group of E) carbamates.

According to a further embodiment, the compositions contain a compound of formula I-4.2 and at least one active ingredient selected from the group of E) carbamates.

According to a further embodiment, the compositions of a compound düng of formula 1-5.1 and at least one active ingredient selected from the group of E) carbamates.

According to a further embodiment, the compositions contain a compound of formula I-5.2 and at least one active ingredient selected from the group of E) carbamates.

According to a further embodiment, the compositions comprise as component 1) at least one of the compounds of the formula I individualized in Tables 1 to 257 and at least one active compound selected from the group of the E) carbamates.

According to a further embodiment of the invention, the compositions according to the invention contain as component 1) at least one compound of the formula I and at least one active compound selected from the group of F) Other fungicides.

According to one embodiment, the compositions contain at least one compound of the formula 1-1.1 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions contain at least one compound of formula 1-1.2 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions comprise at least one compound of the formula I.2.1 and at least one active ingredient selected from the group of F) Other fungicides.

According to a further embodiment, the compositions comprise at least one compound of formula I-2.2 and at least one active ingredient selected from the group of F) other fungicides. According to a further embodiment, the compositions comprise at least one compound of the formula 1-3.1 and at least one active compound selected from the group of F) other fungicides.

According to a further embodiment, the compositions contain at least one compound of formula I-3.2 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions comprise a compound of the formula 1-4.1 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions contain a compound of formula I-4.2 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions of a compound of the formula contain 1-5.1 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions contain a compound of formula I-5.2 and at least one active ingredient selected from the group of F) other fungicides.

According to a further embodiment, the compositions contain as component 1) at least one of the compounds of the formula I individualized in Tables 1 to 257 and at least one active compound selected from the group of the F) other fungicides.

Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active substance selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimol, tebuconazole, tetraconazole, triticonazole , Prochloraz, cyazofamide, benomyl and carbendazim.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active compound selected from the group of A) azoles selected from cyazofamide, metconazole, fluquiconazole, triadimefon, triadimenol, penconazole, hexaconazole and thiadanazole, in particular selected from penconazole, hexaconazole and thiabendazole. Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active substance selected from the group of A) azoles, selected from epoxiconazole, fluconconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbenzim.

Also preferred are compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active ingredient selected from the group of A) azoles, selected from

Cyproconazole, difenoconazole, epoxiconazole, propiconazole, prochlorazone, prothioconazole and tebuconazole, in particular selected from cyproconazole, difenoconazole and propiconazole.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active substance selected from the group consisting of B) strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyracoltrobin and trifloxystrobin.

Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active ingredient selected from the group of B) strobilurins selected from kresoxim-methyl, orysastrobin and pyraclostrobin.

Very particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I. -5.2, with pyraclostrobin.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active ingredient selected from the group of B) strobilurins selected from azoxystrobin, fluoxastrobin, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin, in particular selected from azoxystrobin and picoxystrobin.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active compound selected from the group of C) carboxylic acid amides selected from hexadecido, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamide), zoxamide, carpropamide and mandipropamide. Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active ingredient selected from the group of C) carboxylic acid amides selected from fenhexamide, metalaxyl, mefenoxam, Ofurace, dimethomorph, zoxamide and carpropamide.

Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active ingredient selected from the group of C) carboxylic acid amides, selected from fenhexamide and oxadixyl.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active substance selected from the group of C) carboxylic acid amides selected from boscalide, dimethomorph, metalaxyl, metalaxyl-M, mandipropamide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3-difluoro-methyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl -2-yl) amide and fluopicolide (picobenzamide), especially selected from metalaxyl, mandipropamide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl -2-yl) - amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide and fluopicolide (picobenzamide) ,

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 with at least one active compound selected from the group consisting of D) heterocyclic compounds selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludiooxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole , 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, Proquinazide, acibenzolar-S-methyl, capotafol, folpet, fenoxanil and quinoxyfen, in particular fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole Proquinazide, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen.

Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active compound selected from the group of D) Heterocyclic compounds selected from tridemorph, iprodione, pyrimethanil, fenpropimorph, fenpropidin, Acibenzolar-S-methyl and pyrifenox, in particular selected from Fenpropi- morph, fenpropidin, Acibenzolar-S-methyl and pyrifenox. Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active compound selected from the group of D) Heterocyclic compounds selected from pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline, 5-chloro-7- (4-methyl-piperidin-1-yl) - 6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine and quinoxyfen, especially pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline and quinoxyfen.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active substance of the formula VI selected from the group of the D) heterocyclic compounds selected from Table X:

Table X:

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active compound selected from the group consisting of D) heterocyclic compounds selected from fludioxonil, cyprodinil and 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluoro-) phenyl) - [1, 2,4] triazolo [1,5-a] pyrimidine, in particular selected from fludioxonil and cyprodinil.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active ingredient selected from the group of E) carbamates selected from mancozeb, metiram, propineb, thiram, iprovalicarb, flubenthiavalicarb and propamocarb. Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active ingredient selected from the group of E) carbamates selected from mancozeb and metiram.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active ingredient selected from the group of E) carbamates selected from iprovalicarb and metiram, preferably iprovalicarb.

Also preferred are compositions of a compound of formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 , with at least one active substance selected from the group of F) other fungicides selected from chlorothalonil, fosetyl, fosetyl-aluminum, metrafenone and spiroxamine.

Particular preference is also given to compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I- 5.2, with at least one active substance selected from the group of F) Other fungicides selected from phosphorous acid and its salts, chlorothalonil and metrafenone.

Also preferred are tri-compound compositions of a compound of the formula I, in particular 1-1.1, 1-1.2, 1-2.1, I-2.2, 1-3.1, I-3.2, 1-4.1, I-4.2, 1-5.1 or I-5.2 with two of the abovementioned or preferred active substances II.

Preferred active ingredient combinations according to the present invention are listed in the following Tables M-1 to M-29:

Table M-1

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Propiconazole is. Table M-2

Fungicidal compositions wherein component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is cyproconazole.

Table M-3

Fungicidal compositions wherein component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is difenoconazole. Table M-4

Fungicidal compositions in which component 1) is one of those listed in Tables 1 to 257 individualized compounds of formula I and component 2)

Prochloraz is. Table M-5

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Prothioconazole is. Table M-6

Fungicidal compositions wherein component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is tebuconazole.

Table M-7

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Epoxiconazole is. Table M-8

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Azoxystrobin is. Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Picoxystrobin is. Table M-10

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Fluoxastrobin is. Table M-11

Fungicidal compositions in which component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is trifloxystrobin.

Table M-12

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Orysastrobin is. Table M-13

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Pyraclostrobin is. Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Metalaxyl is. Table M-15

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Mandipropamide is. Table M-16

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Fluopicolide is. Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Boscalid is. Table M-18

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Dimethomorph is. Table M-19

Fungicidal compositions in which component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro) 4-fluoro-biphenyl-2-yl) amide. Table M-20

Fungicidal compositions in which component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro) 5-fluoro-biphenyl-2-yl) amide. Table M-21

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid- (2-bicyclopropyl-2-yl - phenyl) amide. Table M-22

Fungicidal compositions wherein component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is cyprodinil.

Table M-23

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Fludioxonil is. Table M-24

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2) 5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine. Table M-25

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Iprovalicarb is. Table M-26

Fungicidal compositions wherein component 1) is one of the compounds of formula I individualized in Tables 1 to 257 and component 2) is chlorothalonil.

Table M-27

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Fosetyl-Al is. Table M-28

Fungicidal compositions in which component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Spiroxamine is. Table M-29 Fungicidal compositions, wherein component 1) is one of the compounds of the formula I individualized in Tables 1 to 257 and component 2)

Metrafenon is.

According to the present invention, the fungicidal compositions described in the following Tables Z-1 to Z-29 may be particularly preferred:

Table Z-1

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is propiconazole.

Table Z-2

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is cyproconazole. Table Z-3

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is difenoconazole. Table Z-4 Fungicidal compositions, wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is prochloraz. Table Z-5

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is prothioconazole. Table Z-6

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is tebuconazole.

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is epoxyconazole.

Table Z-8

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 that are individualized in Table C and component 2) is azoxystrobin.

Table Z-9

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is picoxystoline.

Table Z-10

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is fluoxastrobin. Table Z-11

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is trifloxystyrene.

Table Z-12 Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is orysastrobin.

Table Z-13

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126, which are individualized in Table C, and component 2) is pyraclostrobin.

Table Z-14

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is metalaxyl. Table Z-15

Fungicidal compositions in which component 1) is one of the dual compounds C-1 to C-126 and component 2) is mandipropamide.

Table Z-16

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126, which are individualized in Table C, and component 2) is fluopicolide.

Table Z-17

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is boscalid. Table Z-18

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is dimethorphomorph.

Table Z-19 Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) amide.

Table Z-20 Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) amide.

Table Z-21 Fungicidal compositions, wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) 3-difluoromethyl-1-methyl-1H-pyrazole-1-carboxylic acid-1-bicyclopropyl. yl-phenoxyamide is.

Table Z-22 Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is cyprodinil.

Table Z-23

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126 which is individualized in Table C and component 2) is fludioxonil.

Table Z-24

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4 , 6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine.

Table Z-25

Fungicidal compositions in which component 1) is one of the dual compounds C-1 to C-126 and component 2) is iprovalicarb.

Table Z-26

Fungicidal compositions in which component 1) is one of the compounds C-1 to C-126, which are individualized in Table C, and component 2) is chlorothalonil.

Table Z-27

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is fosetyl-Al.

Table Z-28

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is spiroxamine. Table Z-29

Fungicidal compositions wherein component 1) is one of the compounds C-1 to C-126 individualized in Table C and component 2) is metrafenone.

Table C

No.

la.3

C-1 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-2 la.3 with Z = NH (CH (CH ₃ ) CF ₃ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-3 la.3 with Z = NH (CH (CHs) ₂ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-4 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-5 la.3 ((CH ₂ CH CHs) ₂₎ with Z = NH; Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-6 la.3 with Z = NH (CH (CHS) CH (CHS) ₂ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-7 la.3 with Z = NH (CH (CHs) C (CH ₃₎ S); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-8 la.3 with Z = N (CH ₃₎ ((CH CHS) _2); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-9 la. 3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-10 la.3 with Z = N (CHs) (CH ₂ CH (CHs) _2); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-1 1 la.3 with Z = N (CH ₃₎ (CH (CHS) CH (CHS) _2); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-12 la.3 with Z = N (CH ₃₎ ((CH CHs) C (CH ₃₎ S); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-13 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-14 la. 3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-15 la.3 with Z = N (C ₂ H ₅ ) (CH ₂ CH (CHs) ₂ ); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-16 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ CH (CHs) _2); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-17 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ C (CHs) _3); Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN C-18 la.3 with Z = piperidin-1-yl; Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-19 la.3 with Z = 2-CH ₃ -piperidine-1-yl; Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-20 la.3 with Z = 3-CH ₃ -piperidine-1-yl; Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-21 la.3 with Z = 4-CH ₃ -piperidine-1-yl; Y = 2,4,6-F ₃ - (C ₆ H ₂ ); R ¹ = CN

C-22 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-23 la.3 with Z = NH (CH (CH ₃ ) CF ₃ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-24 la.3 with Z = NH (CH (CHs) ₂ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-25 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-26 la.3 with Z = NH (CH ₂ CH (CHs) ₂ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-27 la.3 with Z = NH (CH (CHS) CH (CHS) ₂ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-28 la.3 with Z = NH (CH _(CH3) C (CHs) _3); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-29 la.3 ((CH CHs) ₂₎ with Z = N (CH _3); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-30 la.3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-31 la.3 with Z = N (CHs) (CH ₂ CH (CHs) _2); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-32 la.3 with Z = N (CH ₃₎ ((CH CHS) CH (CHS) _2); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-33 la.3 with Z = N (CH ₃₎ ((CH CHs) C (CH ₃₎ S); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-34 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-35 la.3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-36 la. 3 with Z = N (C ₂ H ₅ ) (CH ₂ CH (CHs) ₂ ); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-37 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ CH (CHs) _2); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-38 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ C (CHs) _3); Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-39 la.3 with Z = piperidin-1-yl; Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-40 la.3 with Z = 2-CHs-piperidin-1-yl; Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-41 la.3 with Z = 3-CHs-piperidin-1-yl; Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-42 la.3 with Z = 4-CHs-piperidin-1-yl; Y = 2,5-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-43 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-44 la.3 with Z = NH (CH (CHs) CF _3); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-45 la.3 with Z = NH (CH (CHs) ₂ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-46 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-47 la.3 ((CH ₂ CH CHs) ₂₎ with Z = NH; Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-48 la.3 with Z = NH (CH (CHS) CH (CHS) ₂ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-49 la.3 with Z = NH (CH _(CH3) C (CHs) _3); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-50 la.3 with Z = N (CH ₃₎ ((CH CHS) _2); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-51 la. 3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-52 la.3 with Z = N (CH ₃₎ (CH ₂ CH (CHs) _2); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-53 la.3 with Z = N (CHS) (CH (CH ₃₎ CH (CHS) _2); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-54 la.3 with Z = N (CH ₃₎ ((CH CHs) C (CH ₃₎ S); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-55 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-56 la.3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-57 la.3 where Z = N (C ₂ H ₅ ) (CH ₂ CH (CHs) ₂ ); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-58 la.3 with Z = N (C ₂ H ₅₎ (CH (CHs) CH (CHs) _2); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN C-59 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ C (CHs) _3); Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-60 la.3 with Z = piperidin-1-yl; Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-61 la.3 with Z = 2-CH ₃ -piperidin-1-yl; Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-62 la.3 with Z = 3-CH ₃ piperidin-1-yl; Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-63 la.3 with Z = 4-CH ₃ piperidin-1-yl; Y = 2-CI, 4-F- (C ₆ H ₃ ); R ¹ = CN

C-64 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-65 la.3 with Z = NH (CH (CH ₃ ) CF ₃ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-66 la.3 with Z = NH (CH (CHs) ₂ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-67 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-68 la.3 with Z = NH (CH ₂ CH (CHs) ₂ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-69 la.3 with Z = NH (CH (CHS) CH (CHS) ₂ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-70 la.3 with Z = NH (CH _(CH3) C (CHs) _3); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-71 la.3 ((CH CHs) ₂₎ with Z = N (CH _3); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-72 la. 3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-73 la.3 with Z = N (CHs) (CH ₂ CH (CHs) _2); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-74 la.3 with Z = N (CH ₃₎ ((CH CHS) CH (CHS) _2); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-75 la.3 with Z = N (CH ₃₎ ((CH CHs) C (CH ₃₎ S); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-76 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-77 la. 3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-78 la.3 with Z = N (C ₂ H ₅ ) (CH ₂ CH (CHs) ₂ ); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-79 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ CH (CHs) _2); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-80 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ C (CHs) _3); Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-81 la.3 with Z = piperidin-1-yl; Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-82 la.3 with Z = 2-CHs-piperidin-1-yl; Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-83 la.3 with Z = 3-CHs-piperidin-1-yl; Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-84 la.3 with Z = 4-CHs-piperidin-1-yl; Y = 2,6-F ₂ - (C ₆ H ₃ ); R ¹ = CN

C-85 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-86 la.3 with Z = NH (CH (CHs) CF _3); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-87 la.3 with Z = NH (CH (CHs) ₂ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-88 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-89 la.3 with Z = NH (CH ₂ CH (CHs) ₂ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-90 la.3 with Z = NH (CH _(CH3) CH (CHs) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-91 la.3 with Z = NH (CH _(CH3) C (CHs) _3); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-92 la.3 with Z = N (CH ₃₎ ((CH CHS) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-93 la.3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-94 la.3 with Z = N (CH ₃₎ (CH ₂ CH (CHs) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-95 la.3 with Z = N (CH ₃₎ ((CH CHS) CH (CHS) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-96 la.3 with Z = N (CHs) ((CH CH ₃₎ C (CHs) _3); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-97 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-98 la.3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-99 la.3 with Z = N (C ₂ H ₅₎ (CH ₂ CH (CHs) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN C-100 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ CH (CHs) _2); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-101 la. 3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C (CH ₃ ) ₃ ); Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-102 la.3 with Z = piperidin-1-yl; Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-103 la.3 with Z = 2-CH ₃ -piperidin-1-yl; Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-104 la.3 with Z = 3-CH ₃ -piperidin-1-yl; Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-105 la.3 with Z = 4-CH ₃ -piperidin-1-yl; Y = 3,5-CI ₂ -pyridin-2-yl; R ¹ = CN

C-106 la.3 with Z = NH (CH ₂ CF ₃ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-107 la.3 with Z = NH (CH (CH ₃ ) CF ₃ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-108 la.3 with Z = NH (CH (CHs) ₂ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-109 la.3 with Z = NH (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 10 la.3 with Z = NH (CH ₂ CH (CHs) ₂ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 1 1 la.3 with Z = NH (CH _(CH3) CH (CHs) _2); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 12 la.3 with Z = NH (CH (CH ₃ ) C (CHs) ₃ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 13 la.3 with Z = N (CH ₃ ) (CH (CHS) ₂ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 14 la.3 with Z = N (CH ₃ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 15 la.3 with Z = N (CH ₃₎ (CH ₂ CH (CHs) _2); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 16 la.3 with Z = N (CH ₃₎ (CH (CHS) CH (CHS) _2); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 17 la.3 with Z = N (CHs) ((CH CH ₃₎ C (CHs) _3); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 18 la.3 with Z = N (C ₂ H ₅ ) (CH (CHs) ₂ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-1 19 la.3 with Z = N (C ₂ H ₅ ) (CH (CH ₃ ) C ₂ H ₅ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-120 la.3 with Z = N (C ₂ H ₅ ) (CH ₂ CH (CHs) ₂ ); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-121 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ CH (CHs) _2); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-122 la.3 with Z = N (C ₂ H ₅₎ (CH (CH ₃₎ C (CHs) _3); Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-123 la.3 with Z = piperidin-1-yl; Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-124 la.3 with Z = 2-CHs-piperidin-1-yl; Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-125 la.3 with Z = 3-CH ₃ piperidin-1-yl; Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

C-126 la.3 with Z = 4-CHs-piperidin-1-yl; Y = 2,5-CI ₂ -thiophen-3-yl; R ¹ = CN

The compositions of compound (s) I and at least one of the active compounds II, or the simultaneous joint or separate use of at least one compound I with at least one of the active compounds II, are distinguished by a restorative and yield-increasing effect on plants, in particular legumes, and excellent activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Basidiomycetes, Peronosporomycetes (syn. Oomycetes) and Fungi imperfecti. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.

They are particularly important for the control of a variety of fungi on various crops such as wheat, rye, barley, triticale, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugarcane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans, tomatoes, potatoes and squash, as well as the seeds of these plants.

They may also be used in cultures tolerant by breeding, including genetic engineering, insect or fungal attack or herbicide applications. In addition, they are suitable for the control of Botry- osphaeria species, Cylindrocarpon species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum, which attack, inter alia, the wood or the roots of grapevines.

In particular, they are suitable for controlling the following plant diseases: Alternaria species on vegetables, oilseed rape, sugar beets, fruits, rice, soybeans and on

Potatoes (e.g., A. solani or A. alternata) and tomatoes (e.g., A. solani or A. alternata) and Alternaria ssp. (Spikelet) on wheat,

Aphanomyces species of sugar beets and vegetables,

Ascochyta species on cereals and vegetables e.g. Ascochyta tritici (leaf drought) on wheat, bipolar and Drechslera species on maize (e.g., D. maydis), cereals, rice and turf,

Blumeria graminis (powdery mildew) on cereals (such as wheat or barley),

Botrytis cinerea (gray mold) on strawberries, vegetables, flowers, vines and

Wheat (cereal),

Bremia lactucae on lettuce, Cercospora species on corn, rice, sugar beet and e.g. Cercospora sojina (leaf spot) or Cercospora kikuchii (leaf spot) on soybeans,

Cladosporium herbarum (earwars) on wheat,

Cochliobolus species on corn, cereals (e.g., Cochliobolus sativus) and rice (e.g., Cochliobolus miyabeanus), Colletotricum species on cotton, and e.g. Colletotrichum truncatum (antracnose)

soybeans

Corynespora cassiicola (leaf spot) on soybeans,

Dematophora necatrix (root / stem rot) on soybeans,

Diaporthe phaseolorum (stalk disease) on soybeans, Drechslera species, Pyrenophora species on maize, cereals, rice and turf, on barley

(e.g., D. teres) and wheat (e.g., D. tritici-repentis),

Esca on grapevine caused by Phaeoacremonium chlamydosporium, Ph. Ale- ophilum, and Formitipora punctata (syn. Phellinus punctatus),

Elsinoe ampelina on grapevines, Epicoccum spp. (Spikelet) on wheat,

Exserohilum species on corn,

Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,

Fusarium and Verticillium species on different plants: e.g. F. graminearum or

F. culmorum (root rot) on cereals (e.g., wheat or barley) or e.g. F. oxysporum on tomatoes and Fusarium solani (stalk disease) on soybeans

Gaeumanomyces graminis (root black) on cereals (for example wheat or barley),

Gibberella species on cereals and rice (eg Gibberella fujikuroi), Glomerella cingulata on grapevines and other plants, Grainstaining complex on rice, Guignardia budwelli on grapevines, Helminthosporium species on maize and rice, Isariopsis clavispora on grapevines,

Macrophomina phaseolina (root / stem rot) on soybeans, Michrodochium nivale (snow mold) on cereals (e.g., wheat or barley), Microsphaera diffusa (powdery mildew) on soybeans, Mycosphaerella species on cereals, bananas, and peanuts, e.g. M. graminicola on wheat or M. fijiensis on bananas,

Peronospora species on cabbage (e.g., P. brassicae), bulbous plants (e.g., P. destructor), and e.g. Peronospora manshurica (downy mildew) on soybean Phakopsara pachyrhizi (soybean rust) and Phakopsara meibomiae (soybean rust) on soybeans, Phialophora gregata (stalk disease) on soybeans

Phomopsis species on sunflowers, grapevine (e.g., P. viticola) and soybeans (e.g., Phomopsis phaseoli),

Phytophthora species on various plants e.g. P. capsici on paprika, Phytopthora megasperma (leaf / stem rot) on soybeans, Phytophthora infestans on potatoes and tomatoes,

Plasmopara viticola on vines,

Podosphaera leucotricha on apple,

Pseudocercosporella herpotrichoides (crushed straw) on cereals (wheat or barley),

Pseudoperonospora on various plants e.g. P. cubensis on cucumber or P. humili on hops,

Pseudo-pedicel tracheiphilai on grapevine,

Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals (for example wheat or barley) or asparagus (for example P. asparagi), Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum,

Pyrenophora tritici-repentis (leaf drought) on wheat or Pyrenophora teres (net spots) on barley, Entyloma oryzae on rice, Pyricularia grisea on lawn and cereals, Pythium spp. on lawn, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beets, vegetables and other plants (eg P. ultiumum or P. aphanidermatum), Ramularia collo-cygni (Ramularia / sunburn complex / Physiological leaf spots) Barley, Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and on various other plants such as Rhizoctonia solani (root / stalk rot) on soybean or Rhizoctonia cerealis (wheat eye spot) on wheat or Barley, Rhynchosporium secalis on barley, rye and triticale, Sclerotinia species on rape, sunflower and, for example, Sclerotinia sclerotiorum (stem disease) or Sclerotinia rolfsii (stalk disease) on soybeans, Septoria glycines on leafy soybeans, Septoria tritici (leaf septoria) and Stagonospora nodorum on wheat, Erysiphe (Syn. Uncinula) necator on grapevine, Setospaeria species on maize and turf, Sphacelotheca reilinia on maize, Stagonospora nodorum (Ear septoria) on wheat, Thievaliopsis species on soybean and cotton, Tilletia species on cereals,

Typhula incarnata (snow) on wheat or barley, Ustilago species on cereals, maize (e.g., U. maydis) and sugarcane, Venturia species (scab) on apples (e.g., V. inaequalis) and pears.

The compositions according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In wood preservation, particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriela spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., in addition, in the protection of materials, the following yeasts: Candida spp. and Saccharomyces cerevisae.

The compound (s) I with at least one of the active ingredients II can be applied simultaneously, namely jointly or separately, or in succession, the sequence in the case of separate application generally having no effect on the control result.

The pure substances of the compounds I and the active compounds II are preferably used in the preparation of the compositions, to which other active substances can be added against harmful fungi or against other pests such as insects, spider animals or nematodes or else herbicidal or growth-regulating active substances or fertilizers.

Such compositions of three active ingredients consist, for example, of a compound of the formula I, an azole from the group A) of the active compounds II, in particular epoxiconazole, metconazole, triticonazole or fluquinconazole, and an insecticide, wherein especially fipronil and neonicotinoids such as acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam.

Usually, compositions of at least one compound I, and at least one active ingredient II are used. However, compositions of at least one compound I with two or, if desired, several further active components can also offer particular advantages.

Suitable further active components in the above sense are, in particular, the aforementioned active compounds II and in particular the above-mentioned preferred active compounds II.

Compound (s) I and active compound (II) II are usually used in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.

If desired, the further active components are mixed in a ratio of from 20: 1 to 1:20 to give compound I.

The application rates of the compositions of the invention, especially in agricultural crops, depending on the nature of the compounds I and II and the desired effect at 5 g / ha to 2000 g / ha, preferably 20 to 1500 g / ha, in particular 50 to 1000 g / ha.

The application rates for the compound (s) I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.

The application rates for the active compound II are accordingly generally from 1 to 2000 g / ha, preferably from 10 to 1500 g / ha, in particular from 40 to 1000 g / ha.

In seed treatment, e.g. By dusting, pilling, coating or soaking seed, in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.

When used in material or storage protection, the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.

The compounds of the formula I and the active compounds II can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention. The compositions according to the invention, or the compound (s) of the formula I and at least one of the active compounds II, can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, for example by stretching the active compounds with solvents and carriers or solvents or carriers, if desired using further auxiliaries, such as emulsifiers or dispersants. Individual substances can also fulfill different functions. As solvents, carriers or adjuvants which are suitable are essentially: -water, aromatic solvents (for example Solvesso ^® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures can also be used.

Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) or ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin liquors and methyl cellulose.

The compositions of the invention may be formulated in solid form or in liquid form. Depending on the embodiment, the compositions according to the invention may also contain auxiliaries and / or carriers, as are customary in plant protection agents or in agents for the protection of materials. The auxiliaries include, in particular, conventional surface-active substances and other additives customary in plant and material protection and carriers which may be solid or liquid. The surface-active substances include, in particular, surfactants, in particular those which have wetting agent properties. The other auxiliaries (additives) include, in particular, thickeners, defoamers, preservatives, antifreeze agents, stabilizers, anticaking agents or flow aids and buffers.

Principally useful conventional surface-active substances are anionic, nonionic and amphoteric surfactants, including polymer surfactants, wherein the molecular weight of the surfactants typically will not exceed a value of 2000 daltons and in particular 1000 daltons (number average). The anionic surfactants include, for example, carboxylates, especially alkali, alkaline earth and ammonium salts of fatty acids, eg. B. potassium stearate, which are commonly referred to as soaps; glutamates; Sarcosinates, e.g. For example, sodium lauroyl sarcosinate; taurates; Methylcelluloses; Alkyl phosphates, especially mono- and diphosphoric acid alkyl esters; Sulfates, in particular alkyl sulfates and alkyl ether sulfates; Sulphonates, other alkyl and alkylarylsulphonates, in particular alkali, alkaline earth and ammonium salts of arylsulfonic acids and alkyl-substituted arylsulfonic acids, alkylbenzenesulfonic acids, such as lignin and phenolsulfonic acid, naphthalene and dibutylnaphthalenesulfonic acids, or dodecylbenzenesulfonates, alkylnaphthalenesulfonates, alkylmethylsulfonates, condensation products of sulfonated Naphthalene and derivatives thereof with formaldehyde, condensation products of naphthalenesulfonic acids, phenol- and / or phenolsulfonic acids with formaldehyde or with formaldehyl and urea, mono- or dialkylsuccinic acid sulfonates; as well as protein hydrolysates and lignin sulphite waste liquors. The abovementioned sulfonic acids are advantageously used in the form of their neutral or optionally basic salts.

Nonionic surfactants include, for example:

Fatty alcohol alkoxylates and oxo alcohol alkoxylates, in particular ethoxylates and propoxylates having degrees of alkoxylation of usually 2 to 100 and in particular 3 to 50, eg. B. alkoxylates of Cs-Cso alkanols or alk (adi) enols, z. B. of iso-tridecyl alcohol, lauryl alcohol, oleyl alcohol or stearyl alcohol and their C 1 -C ₄ alkyl ethers and C ₄ alkyl esters, for example, their acetates; alkoxylated animal and / or vegetable fats and / or oils, for example corn oil ethoxylates, castor oil ethoxylates, tallow fatty ethoxylates, glycerol esters, such as, for example, glycerol monostearate,

Alkylphenol alkoxylates, such as, for example, ethoxylated isooctyl, octyl or nonylphenol, tributylphenol polyoxyethylene ethers,

Fettaminalkoxylate, Fettsäureamid- and fatty acid diethanolamidalkoxylates, in particular their ethoxylates, - sugar surfactants, sorbitol esters, such as sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), Polyoxyethylensorbitanfettsäureester, alkyl polyglycosides, N-alkylgluconamides, alkylmethylsulfoxides, alkyldimethylphosphine, such as tetradecyldimethylphosphine.

The amphoteric surfactants include, for example, sulfobetaines, carboxybetaines and alkyldimethylamine oxides, e.g. B. tetradecyldimethylamine oxide.

Other surfactants which are to be mentioned here by way of example are perfluorosurfactants, silicone surfactants, phospholipids, such as lecithin or chemically modified lecithins, amino acid surfactants, eg. B. N-lauroylglutamate. For the production of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg toluene, Xy- lol, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

Powders, dispersants and dusts can be prepared by mixing or jointly grinding the active components A and B and, if present, further active ingredients with at least one solid carrier.

Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to at least one solid carrier. Solid carriers are e.g. Mineral soils such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable Products such as cereal flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations of the compounds according to the invention generally contain 0.01 to 95 wt .-%, preferably 0.1 to 90 wt .-% of the compounds I and II. The active ingredients are preferably in a purity of 90% to 100%, preferably 95% to 100% used.

For seed treatment, the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.

The formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the compound (s) I and at least one of the active compounds II or the composition of compound (s) I with at least one of the active ingredients II. The compounds and active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are: 1. Products for dilution in water

A) Water-soluble concentrates (SL, LS) 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other auxiliaries added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.

B) Dispersible Concentrates (DC) 20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion. The active ingredient content is 20% by weight

C) Emulsifiable Concentrates (EC) 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The formulation has 15% by weight active ingredient content.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.

E) suspensions (SC, OD, FS)

20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.

F) Water-dispersible and water-soluble granules (WG, SG) 50 parts by weight of the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient. The formulation has an active ingredient content of 50% by weight.

G) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight. H) gel formulations (GF)

In a ball mill, 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part of swelling agent ("gelling agent") and 70 parts by weight of water or an organic solvent are ground to a fine suspension - Tung with water results in a stable suspension with 20 wt .-% active ingredient content.

2. Products for direct application

I) Dusts (DP, DS) 5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.

J) Granules (GR, FG, GG, MG) 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray-drying or agglomeration in the fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.

K) ULV solutions (UL)

10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent, e.g. XyIoI solved. This gives a product for direct application with 10 wt .-% active ingredient content.

For seed treatment, water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF) are usually used. These formulations can be applied to the seed undiluted or, preferably, diluted. The application can be done before sowing.

The compounds and active compounds or compositions may be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring. The forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the sub- punched as such or dissolved in an oil or solvent, be homogenized by means of wetting, adhesive, dispersing or emulsifying agent in water. However, it is also possible to prepare concentrates which are active substance wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oils which are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.

To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.

As adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ^® ; Alcohol alkoxylates, eg. As Atplus 245 ^®, Atplus MBA 1303 ^®, Plurafac LF 300 ^® and Lutensol ON 30 ^®; EO-PO block polymers, eg. B. Pluronic RPE 2035 ^® and Genapol B ^®; Alcohol ethoxylates, eg. As Lutensol XP 80 ^®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ^®.

The compositions according to the invention or the corresponding formulations are used by treating the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount of the composition or the compounds I and the active compounds II with separate application, treated. The application can be made before or after the attack by the harmful fungi.

Use Examples The fungicidal activity of the individual compounds according to Table D and individual active substances according to Table E and of the compositions according to the invention can be demonstrated by the following experiments. Table D:

Compounds of the formula Ia

Table E

microtiter assay

The compounds and drugs were formulated separately as stock solution at a concentration of 10,000 ppm in DMSO.

The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

Use Example 1 Activity against the causative agent of the late blight Phytophthora infestans in the microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted to the stated active compound concentration with an aqueous, pea-based fungal nutrient medium. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs are measured at 405 nm on the 7th day after inoculation.

Application Example 2 Activity against the causative agent of the gray mold Botrytis cinerea in the microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungus nutrient medium to the stated active compound concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs are measured at 405 nm on the 7th day after inoculation.

Use Example 3 - Activity against the causative agent of rice blast Pyricularia oryzae in the microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae. The plates were added in a water vapor saturated chamber Temperatures of 18 ° C set up. Using an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

Application Example No. 4 - Activity against the causative agent of the Septoria leaf drought Septoria tritici in the microtiter test

The stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Septoria tritici. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

From the results of the experiments, it is clear that the mixtures according to the invention are considerably more effective due to the synergism than predicted by the CoI by formula.

Claims

claims

1. Fungicidal compositions for controlling phytopathogenic

Harmful fungi, comprising

1) at least one compound of the formula I.

wherein the substituents have the following meanings:

R ^{1 is} hydrogen, halogen, cyano, nitro, C ¹ -C 6 -alkyl, C ¹ -C 6 -haloalkyl,

Ci-Cs-hydroxyalkyl, _{Ci-C8-alkoxy-Ci-C 8} alkyl, C ₂ -C ₈ alkenyloxy-Ci-C ₈ - alkyl, _{C2-C8-alkynyloxy-Ci-C 8} alkyl, C ₃ -C ₈ cycloalkyloxy-Ci-C ₈ alkyl, C ₈ - alkoxyalkyloxy-C ₈ alkyl, benzyloxy-Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl, Ci-C8-alkoxy,} Ci-C ₈ - haloalkoxy, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl, hydroxyimino

Ci-C ₈ alkyl, a remainder

wherein p is 1, 2, 3, 4 or 5 and # is the point of attachment to the pyrazolopyrimidine skeleton; wherein the aliphatic and alicyclic groups may contain one, two, three or four identical or different R ^a ;

C (= W ¹ ) NH ₂ , where W ¹ means:

W ^{1 is} S, O, NH, N-OH or N-OW ² , where W ^{2 is} C ₁ -C ₆ -alkyl or C ₆ -

Ci4-aryl-Ci-C ₈ alkyl, wherein W ² may contain one, two, three or four identical or different groups R ^a ;

C (W ³ ) = N (W ⁴ ), where W ³ , W ^{4 are}

W ^{3 is} hydrogen or C ¹ -C 6 -alkyl;

W ^{4 is} C 1 -C ⁶ -alkyl, phenyl or phenylamino;

wherein W ³ and W ^{4 may} each independently contain one, two, three or four identical or different groups R ^a ; CW ⁵ (= O), where W ⁵ means:

W ^{5 is} hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, benzyl, where W ^{5 is} one, two, three or four identical or different Groups R ^a may contain;

CONW ⁶ W ⁷ , CONW ⁷ -N (W ⁷ ) ₂ , CO-NW ⁷ -OW ⁷ , COOW ⁸ , C (S) OW ⁷ , C (O) SW ⁷ , C (S) SW ⁷ , SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁷ , SON (W ⁷ ) ₂ , SO ₂ N (W ⁷ ) ₂ , P (O) (OW ⁷ ) ₂ , NW ⁷ OW ⁷ , B (OW ⁷ ) ₂ , - (CW ⁷ ₂ ) o- ₆ -NW ⁷ ₂ or - (CW ⁷ ₂ ) ₀ - ₆ -NW ⁷ -

NW ⁷ ₂ ; where W ⁶ , W ⁷ , W ^{8 are} each independently:

W ⁶ is d-Cio-alkyl, C ₂ -C 10 -alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, Ce-Cu-aryl, C ₆ -C ₄ -aryl -Ci-C ₈ -alkyl;

W ^{7 is} hydrogen or one of the radicals mentioned at W ⁶ ;

two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ can also together form a saturated or partially unsaturated cycle having 3, 4, 5 or 6 carbon atoms, the 1 or 2 further hetero atoms selected from nitrogen, sulfur and oxygen may contain;

W ⁸ is hydrogen, a cation, Ci-C ₈ alkyl, C ₂ -C ₈ -alkenyl -alkyl, C ₂ -C ₈ - alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -alkenyl or C ₆ -Cycloal -C 1 -C ₄ -Ary I-C ₈ - alkyl;

W ⁶ , W ⁷ , W ⁸ or a cycle formed from W ⁷ or W ⁷ and W ⁶ may each independently contain one, two, three or four identical or different R ^a groups;

saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl which may contain one, two, three or four identical or different groups R ^a ;

where R ^a means:

R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, Ci-C ₈ alkyl, Ci-C ₈ -HaIo- genalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Al kinyl, C ₃ -C ₈ - haloalkynyl, C4-Cio-alkadienyl, C ₈ alkoxy, Ci-C ₈ -Halogenalk- oxy, C2-C8-alkenyloxy, C2-C8 haloalkenyloxy, C2-C8-alkynyloxy, Cs-Cs-haloalkynyloxy, C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl, _C3-C8 cycloalkoxy , C3-C ₈ -Halogencycloalkoxy nyloxy, Cs-Cs-cycloalkenyloxy, Cs-do-bicycloalkyl, Ci-Cs-alkylcarbonyloxy, Ci-Cs-alkoxycarbonyloxy, aminocarbonyloxy, d-Cs-Alkylaminocarbo-, di-d-Cs-alkylaminocarbonyloxy, C 1 -C 8 -alkylthiocarbonyloxy, C 1 -C 8 -alkoxythiocarbonyloxy, aminothiocarbonyloxy, C 1 -C 5 -alkylaminothiocarbonyloxy, C 1 -C 5 -alkylaminothiocarbonyloxy C 1 -C ₈ -alkylaminothiocarbonyl, C 1 -C -alkylaminothiocarbonyl, C 1 -C 6 -alkylene, Oxy-C 2 -C 4 -alkylene, oxy-C 1 -C 4 -alkyleneoxy, = CH 2, imino

(= NH), (C 1 -C ₄ -alkoxy) imino (= N- (C 1 -C ₄ -alkoxy)), (C 1 -C ₄ -alkyl) -imino (= N- (C 1 -C ₄ -alkyl) ), -C (= O) -A, -C (= O) -OA, -C (= O) -N (A ') A, C (A') (= N-OA), N (A ¹ JA, N (A ') -C (= O) -A, N (A ") -C (= O) -N (A') A, S (= O) _m -A, S (= O) mOA , S (= O) mN (A ') A, -Si (C ₁ -C ₆ -alkyl) ₃ , phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, where m, A, A 'and A "are

m is 0, 1 or 2;

A, A ', A "independently of one another are hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ Cycloalkenyl, phenyl, where the organic radicals may be partially or fully halogenated and / or monosubstituted or polysubstituted by nitro, cyanoato, cyano, C 1 -C ₄ -alkoxy, and A and A may also be used together with the atoms to which they are attached represent a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S.

where the aliphatic, alicyclic and / or aromatic groups in R ^{a can in} turn carry one, two or three identical or different groups R ^b :

R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, C ₁ -C ₆ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₄ -C 10 -alkadienyl, C ₃ -C ₈ -cycloalkyl , Cs-Cs-cycloalkenyl, Cs-Cio-bicycloalkyl, d-Cs-alkoxy, _C2-C8 alkenyloxy, C ₂ -C ₈ - alkynyloxy, C3-Cs-cycloalkoxy, C3-Cs-cycloalkenyloxy, Aminothiocar- carbonyl, C ₁ -C ₆ -alkylcarbonyloxy, C ₁ -C 5 -alkylaminothiocarbonyl, C ₁ -C ₈ -alkylaminothiocarbonyl, C ₁ -C ₈ -alkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₈ -alkylsulfonyl, C ₆ -C ₄ -aryl, C _{4 6} -C aryloxy, C ₆ -C ₄ arylthio, C ₆ -C ₄ aryl Ci-Cβ-alkoxy, C6-C ₄ aryl Ci-C6-alkyl, five- to ten-membered-saturated gesät-, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, heterocyclyloxy, heteroaryloxy, heteroarylthio, -C (= O) -A, -C (= O) - OA, -C (= O) -N (A ') A, C (A') (= N-OA), N (A ') A; it being possible for the aliphatic, alicyclic or aromatic groups logeniert partially or fully HA and / or by Ci-Cs-alkyl and / or C ₈ haloalkyl groups substituted;

R ₈ alkyl, d-Cs-haloalkyl, CrC oxy ₈ -AIk-, CRCS haloalkoxy, Ci-Cs-alkylthio, d-Cs-alkylsulfinyl, dC ₈ alkyl sulfonyl ² is hydrogen, halogen, cyano, Ci-C , _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl; wherein R ² may contain one, two, three or four identical or different groups R ^a

X is hydrogen, halogen, hydroxy, cyano, N (A ') A, d-Cs-alkoxy, CrC genalkoxy ₈ -HaIo-, Ci-Cs-alkylthio, d-Cs-alkylsulfinyl, dC ₈ alkylsulfonyl, CrC ₈ - alkyl , dC ₈ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -

Alkynyl, C ₃ -C ₈ -haloalkynyl, cyano-dC ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl;

Y - a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and

Sulfur, wherein the heterocycle is unsubstituted or substituted with one, two, three or four identical or different substituents L;

Phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L;

where L means:

L is halogen, cyano, nitro, hydroxy, cyanato (OCN), dC ₈ alkyl, -C ₈ - haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -alkyl ki nyl , C ₃ -C ₈ -

Haloalkynyl, C ₄ -Cio-alkadienyl, C ₄ -Cio-Halogenalkadienyl, CrC oxy ₈ -AIk-, d-Cs-haloalkoxy, d-Cs-alkylcarbonyloxy, dC oxy ₈ alkylsulfonyl, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ haloalkenyloxy, C ₂ -C ₈ alkynyloxy, C ₂ - C ₈ haloalkynyloxy, _C3-C8 cycloalkyl, _{C3-C8-halocycloalkyl,} C3-C ₈ - cycloalkenyl, C3-C ₈ - halocycloalkenyl, _C3-C8 cycloalkoxy, C3-C6 Cycloalkenyloxy, hydroxyimino-Ci-Cs-alkyl, d-Cβ-alkylene, OxV-C ₂ -C ₄ -alkylene, oxy-Ci-C4-alkyleneoxy, Ci-C ₈ -alkoximino-Ci-C ₈ -alkyl, C ₂ C ₈ -Alk-enyloximino-C 1 -C ₈ -alkyl, C 2 -C ₈ -alkynyloximino-C 1 -C ₈ -alkyl, S (OO) _n A ¹ , C (OO) A ² , C (SS) A ² , NR ⁵ R ⁶ , NR ⁵ -C = OR ⁶ , C (= N-OR ⁷ ) (NR ⁸ R ⁹ ), C (= N-NR ¹⁰ R ¹¹ ) (NR ¹² R ¹³ ) or a five-, a six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur; where n, A ¹ , A ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ^{13 are}

n is 0, 1 or 2;

A ^{1 is} hydrogen, hydroxy, C ¹ -C 8 -alkyl, C ¹ -C -haloalkyl, amino,

Ci-Ce-alkylamino or di-C-i-Cs-alkylamino,

A ^{2 is} one of the groups named A ¹ or NR ⁵ R ⁶ , C ² -C 8 -alkenyl,

C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -haloalkynyl, C ₁ -C ₅ -alkoxy, C ₁ -C -haloalkoxy, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -haloalkenyloxy, C ₂ -C ₈ -alkynyloxy, C3-Cs-haloalkynyloxy, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, _C3-C8 cycloalkoxy,

Cs-Cs-halocycloalkoxy;

R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ independently of one another hydrogen,

Ci-Cs-alkyl, Ci-Cs-haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ - haloalkenyl, C ₂ -C ₈ -alkyl kinyl, _{C3-C8-haloalkynyl,} Cs-Cs

Cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkenyl or C3-Cs-halocycloalkenyl,

R ⁸ and R ⁹ , R ¹⁰ and R ¹¹ and / or R ¹² and R ¹³ may also together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which is unsubstituted or is substituted with one, two, three or four identical or different substituents R ^a ;

where L can carry one, two, three or four identical or different groups R ^L ;

R ^{L is} halogen, cyano, C ₁ -C ₈ alkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ alkynyloxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, C ₃ -C ₈ cycloalkyloxy, Cs _C8 - cycloalkenyloxy, C ₈ -Alkoximino, C ₂ -C ₈ -Alkenyloxyimino, C ₂ -C ₈ -Alkin- yloxyimino, Ci-Cs-alkoximino-d-Cs-alkyl, d-Cs-alkenyloximino-d-Cs-alkyl, C2-C8-alkynyloximino-Ci-C8-alkyl;

C ₁ -C 10 -alkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -alkynyl, C ₃ -C 10 -cycloalkyl, C ₃ -C 10 -cycloalkenyl or an imino group; where these radicals can carry one, two, three or four identical or different groups R ^a and / or two substituents bonded to the same or adjacent atoms or ring atoms for C 1 -C 6 -alkylene, oxy-C 2 -C 4 -alkylene or Oxy-Ci-C4-alkyleneoxy can stand;

Z NR ³ R ⁴ , where R ³ and R ^{4 are}

R ³ Ci-Cs-alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -Halogenalken- yl, C ₂ -Cs-Al kinyl, Cs-Cs haloalkynyl, C4-Cio -alkadienyl, d-do-alkadienyl halogen, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, C ₂ -C 8 alkenyloxy, C ₂ -CS-

Haloalkenyloxy, C ₂ -C 8 alkynyloxy, C 5 -C 8 haloalkynyloxy, C ₃ -C 8 cycloalkyl, C ₁ -C 8 halocycloalkyl, C ₁ -C 8 cycloalkenyl, C 1 -C 8 halo cycloalkenyl, C 1 -C 8 cycloalkoxy, Cs-Cs Halocycloalkoxy, C 1 -C 10 -cycloalkyl, amino, C 1 -C 8 -alkylamino, di-C 1 -C 5 -alkylamino, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two or three or four heteroatoms from the group O, N and S;

R ^{4 is} hydrogen, hydroxy or one of the meanings given for R ³ ;

R ³ and R ⁴ may also together with the nitrogen atom to which they are attached form a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two or three further heteroatoms from the group O, N and S as ring members may contain; in which

R ³ and / or R ⁴ or a heterocycle formed from R ³ and R ⁴ may carry one, two, three or four identical or different groups R ^a and / or two substituents attached to adjacent ring atoms for C 1 -C 6 -alkylene, oxy- dd-alkylene or oxy-dd-alkylenoxy;

or an agriculturally acceptable salt thereof; and

2) at least one active ingredient II selected from groups A) to F): A) Azoles selected from bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, Triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochlorazole, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridizole, hymexazole, azaconazole, diniconazole-M, oxpoconazole, paclobutrazole, Uniconazole, 1- (4-chlorophenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol and imazalil sulfate;

B) strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, (2-chloro-5- [1- (3-methylbenzyl-oxyimino) - ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1 - (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) carbamic acid methyl ester, 2- (ortho ( Methyl 2,5-dimethyl-phenyl-oxymethylene) -phenyl) -3-methoxyacrylate, 2- (2- (6- (3-chloro-2-methyl-phenoxy) -5-fluoropyrmidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide and methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclo-propane-carboxymethyl-sulfanyl-methyl) -phenyl) -acrylate;

C) Carboxylic acid amides selected from carboxin, benalaxyl, benodanil, boscalid, fenfuram, fenhexamide, flutolanil, furametpyr, mepronil, meta-laxyl, mefenoxam, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro - phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-methanesulfonyl-amino-3-methyl-butyramide, N- (2- [4- [3- (4-chloro-phenyl ) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methyl-butyramide, 3- (4-chloro-phenyl) -3- (2-isopropoxycarbonylamino-3-yl) methyl-butyrylaminopropionic acid methyl ester, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole 5-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-chloro-3'- fluorobiphenyl-2-yl) amide, 3- Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3-di-fluoromethyl-1-methyl-pyrazole-4 carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-bicyclopropyl-2-yl-phenyl) -amide, benalaxyl-M, metalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N- (1, 1, 3-trimethyl- indan-4-yl) nicotinamide, N- (2- (1,3-dimethylbutyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, N- (4'- Chloro-3 ', 5-difluoro-biphenyl-2-yl) -3-difluoromethyl-i-methyl-1H-pyrazole-4-carboxamide, N- (4'-chloro-3', 5-difluoro-biphenyl- 2-yl) -3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (cis-2-bicyclopropyl-2-ylphenyl) -3-difluoromethyl-1-methyl-1H-pyrazole -4-carboxamide, N- (trans-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, fluopyram, N- (3-ethyl-3,5 -5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxy-benzamide,

Oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropane carboxamide, penthiopyrad and an i-methyl-pyrazol-4-ylcarboxanilide of the formula III

wherein the substituents have the following meanings:

X is hydrogen or fluorine;

R ^{1 is} C ¹ -C ₄ -alkyl or C ¹ -C ₄ -haloalkyl;

R ^{2 is} hydrogen or halogen;

R ³ , R ⁴ and R ⁵ independently of one another are hydrogen, cyano, nitro, halogen, C 1 -C ₄ -alkyl, C 1 -C ₄ -haloalkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -

Haloalkoxy, C 1 -C ₄ -alkylthio or C 1 -C ₄ -haloalkyl;

D) heterocyclic compounds selected from fluazinam, pyrifenox,

Bupirimat, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforin, fenpiclonil, fludioxonil, aldimorph, dodemorph,

Fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozoline, famoxadone, fenamidone, octhilinone, probenazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluoro -phenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, anilazine, diclomethine, pyroquilone, proquinazide, tricyclazole, the compound of formula IV (2-butoxy-6-iodo-3-propyl-chromen -4-one)

IV,

Acibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1 sulfonic acid dimethylamide of the formula V

2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-di-carbonitrile, N- (1- (5-bromo-3-chloro-pyridine) 2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichloro-nicotinamide, diflumetorim, nitrapyrin, Dodemorph acetate, fluoroimide, blasticidin-S, quinomethionate, debacarb, difenzoquat, difenzoate methyl sulfate, oxolinic acid, piperine and an azolopyrimidin-7-ylamine of the formula VI

wherein the substituents have the following meanings: E ^{1 is} C ₃ -Ci2 alkyl, C ₂ -C ₂ -alkenyl, C ₅ -C ₂ -alkoxyalkyl, C ₃ -C ₆ cycloalkyl,

Phenyl or phenyl-C 1 -C ₄ -alkyl; E ² Ci-Ci2-alkyl, _C2-Ci2 alkenyl, Ci-C ₄ haloalkyl or Ci-C ₄ alkoxy dC ₄ alkyl; wherein the aliphatic groups in E ¹ and / or E ^{2 in} turn carry one, two, three or four identical or different groups R ^a , which are independently selected from: R ^a halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl , C1-C10-

Haloalkyl, C ₃ -C ₈ cycloalkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, -C ₆ - alkoxy, Ci-C ₆ alkylthio, Ci-Ce-alkoxy-Ci-Ce-alkyl, and NR ^A R ^B ; in which

R ^A , R ^B independently of one another are hydrogen or ^C 1 -C 6 -alkyl; wherein the cyclic groups in E ¹ and / or R ^a may carry one, two, three identical or different groups R ^b , which are independently selected from:

R ^{b is} halogen, cyano, hydroxyl, mercapto, nitro, NR ^A R ^B , C ₁ -C 10 -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl and C ₁ -C ₆ - alkoxy; E ³ is hydrogen, halogen, cyano, NR ^A R ^B, hydroxyl, mercapto, Ci-C ₆ - alkyl, Ci-Ce-haloalkyl, C ₃ -C ₈ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ - alkylthio, Cs-Cs-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxycarbonyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -alkynyloxycarbonyl, phenyl, phenoxy,

Phenylthio, benzyloxy, benzylthio and C 1 -C 6 -alkyl-S (O) _m -;

m is 0, 1 or 2;

A is CH or N;

E) Carbamates selected from Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavalicarb, Propamocarb, N- (1- (1 - (4-cyanophenyl) ethanesulfonyl -but-2-yl) carbamic acid (4-fluorophenyl) ester, 3- (4-chloro-phenyl-3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino-propanoic acid methyl ester of the formula VII

and carbamato oxime ethers of the formula VIII

Z is N or CH;

Metasulfocarb and propamocarb hydrochloride;

F) Other fungicides selected from guanidine, dodin, iminoctadine, iminoctadin triacetate, guazatine, guazatine acetate, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithionon, isoprothiolane, organometallic compounds : Fentin salts, organophosphorus compounds: Edifenphos, Iprobenfos, Fosetyl, Fosetyl-

Aluminum, phosphorous acid and its salts, pyrazophos, tolclofosmethyl, organochlorine compounds: chlorothalonil, dichlofluanid, fluorosulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, inorganic active substances: bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine, iminoctadine tris (albesilat), casagungycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its salts, N - (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide,

Diclorane, nitrothal-isopropyl, tecnazene, biphenyl, bronopol, diphenylamine, mildiomycin, oxine-copper, prohexadione-calcium, N- (cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluoro-phenyl) -methyl) -2- phenyl-acetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - (4- (4-fluoro 3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) N-ethyl-N-methylformamidine and N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine;

in a synergistically effective amount.

2. Fungicidal compositions according to claim 1, wherein in component 1) Y is a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle, the one, two, three or contains four heteroatoms from the group oxygen, nitrogen and sulfur, wherein the heterocycle is unsubstituted or substituted by one, two, three or four identical or different substituents L, as defined in claim 1.

3. Fungicidal compositions according to claim 1, wherein in component 1) Y is phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L as defined in claim 1.

4. Fungicidal compositions according to claim 3, wherein in component 1) Y is 2-fluoro-6-chlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-6-methylphenyl, 2,4,6- Trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, 2-chloro-4-methoxyphenyl, pentafluorophenyl, 2-methyl-4-fluorophenyl, 2-trifluoromethylphenyl, 2-methoxy-6-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-

Fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2,3-di-fluorophenyl, 2,5-difluorophenyl, 2,3,4-trifluorophenyl, 2-methylphenyl, 2, 4-dimethylphenyl, 2-methyl-4-chlorophenyl, 2-methyl-5-fluorophenyl, 2-fluoro-4-methylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,6-difluoro- 4 methylphenyl, 2-trifluoromethyl-4-fluorophenyl, 2-trifluoromethyl-5-fluorophenyl, 2-trifluoromethyl-5-chlorophenyl or 2-fluoro-3-methoxyphenyl.

5. Fungicidal compositions according to claim 1, wherein in component 1) Y is Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C ₃ -Cio-cycloalkyl or C ₃ -Cio-cycloalkenyl where these radicals can carry one, two, three or four identical or different groups R ^a and / or two substituents attached to the same or adjacent atoms or ring atoms for C ₁ -C 6 -alkylene, oxy-C ₂ -C ₄ -alkylene or Oxy-Ci-C4-alkyleneoxy as defined in claim 1.

6. Fungicidal compositions according to one of claims 1 to 5, wherein ₄ -haloalkoxy in component 1) X is halogen, cyano, -C ₄ -alkoxy or Ci-C.

7. Fungicidal compositions according to one of claims 1 to 5, wherein ₄ -haloalkyl in component 1) X is _Ci-C4-alkyl or Ci-C.

8. Fungicidal compositions according to any one of claims 1 to 7, wherein in component 1) R ^{1 is} chlorine, nitro, bromine, CONH ₂ , iodine, CHO, CH = NOCH ₃ , cyclopropyl, COOCH ₃ , CH = NOH or cyano ,

9. Fungicidal compositions according to any one of claims 1 to 8, wherein in component 1) R ^{4 is} not hydrogen.

10. Fungicidal compositions according to any one of claims 1 to 9, wherein in

Component 1) R ³ and R ⁴ together with the nitrogen atom to which they are attached form a five- or six-membered saturated or partially unsaturated heterocycle which may contain one or two further heteroatoms from the group O, N and S as ring members, wherein the heterocycle may carry one, two or three identical or different groups R ^a .

1 1. Fungicidal compositions according to any one of claims 1 to 10, wherein the component 2) is selected from azoxystrobin, dimoxystrobin, fluoxastrobin, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.

12. Fungicidal compositions according to any one of claims 1 to 10, wherein the component 2) is selected from Cyproconazole, Difenoconazole, Epoxiconazole, Prochloraz, Propiconazole, Prothioconazole and Tebuconazole.

13. Fungicidal compositions according to any one of claims 1 to 10, wherein the component 2) is selected from chlorothalonil, fosetyl-aluminum, metrafenone and spiroxamine.

14. Fungicidal compositions according to any one of claims 1 to 10, wherein the component 2) is selected from boscalid, dimethomorph, fluopicolide, malepropamide, metalaxyl, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ( 2-bicyclopropyl-2-yl-phenyl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide and 3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -amide.

15. Fungicidal compositions according to any one of claims 1 to 10, wherein the component 2) is selected from cyprodinil, fludioxonil, iprovalicarb, and 5-chloro-7- (4-methyl-piperidin-1-yl-6- (2,4 , 6-trifluoro-phenyl- [1,2,4] triazolo [1,5-a] pyrimidine.

16. Fungicidal compositions according to any one of claims 1 to 15, comprising components 1) and 2) in a weight ratio of 100: 1 to 1: 100.

17. A composition comprising at least one liquid or solid carrier and at least one composition according to one of claims 1 to 16.

18. A method for controlling phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil, seeds, areas, materials or spaces with an effective amount of at least one compound I and at least one compound II according to one of Claims 1 to 16 treated.

19. Process according to claim 18, wherein the components 1) and 2) are applied together simultaneously, separately at the same time or successively.

20. The method according to claim 18 or 19, wherein the components 1) and 2) in an amount of 5 g / ha to 2000 g / ha expended.

21. The method according to claim 18, wherein applying the components 1) and 2) in an amount of 1 g to 1000 g per 100 kg of seed.

22. Seed comprising at least one composition according to any one of claims 1 to 16 in an amount of 1 g to 1000 g per 100 kg of seed.

23. Use of the compounds I and II according to one of claims 1 to 16 for the preparation of a suitable agent for controlling harmful fungi.