WO2007118844A1 - Substituted pyrazolopyrimidines, process for their preparation and their use for controlling harmful fungi and compositions comprising them - Google Patents

Abstract

Compounds of the formula (I) in which the substituents are as defined in the description. The invention further relates to fungicidal and pharmaceutical compositions comprising these compounds and to their use for controlling phytopathogenic fungi and cancer.

Description

Substituted pyrazolopyrimidines, process for their preparation and their use for controlling harmful fungi and agents containing them

description

The present invention n of the formula I.

wherein the substituents have the following meanings:

R ^{1 is} hydrogen, halogen, cyano, nitro, C 1 -C ₈ -alkyl, C 1 -C ₈ -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkynyloxy-C ¹ -C 4 -alkyl Cβ-alkyl, Ca-Cs-alkynyloxy-Ci-Cs-alkyl, C ₃ -C ₈ cycloalkyloxy-Ci-C ₈ alkyl, Ci-C ₈ alkoxy _{Ci-C8-alkoxy-Ci-C 8} - alkyl, aryloxy-C ₁ -C ₈ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₁ -C ₈ - alkoxy, _{Ci-C8-haloalkoxy, C3-C8} cycloalkyl, _C3-C8 halocycloalkyl, hydroxyimino-Ci-C ₈ -alkyl, or a radical

wherein p is 1, 2, 3, 4 or 5 and # is the point of attachment to the pyrazolopyrimidine skeleton; wherein the aliphatic, aromatic 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 ₈ -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 ;

CW ⁵ (= 0), 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 ⁸ , C (O) SW ⁸ ,

C (S) SW ⁸ , SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁸ , 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 d-Cio-alkyl, C ₂ -C -alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -

Cycloalkenyl, C ₆ -C ₄ -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 one radical W ⁷ and one radical W ⁶ may also together form a saturated or partially unsaturated 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 metal equivalent, an ammonium ion of the formula

(NR ^α R ^ß R ^γ R ^{δ) +,} wherein R ^α, R ^Q, R ^γ and R ^δ independently represent H, d-Cio-alkyl, Ci-Cio-hydroxyalkyl, aryl or aryl-Ci-C ₄ - alkyl, Ci-C ₈ - alkyl, (CHR -CHR ^{w w} -O) _m - (C _{r C4)} alkyl where R ^w is H or CH ₃ and m = 1 to 6, C ₂ -C ₈ alkenyl C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl or C ₆ -C ₄ -aryl-C ₁ -C ₈ -alkyl;

W ⁶ , W ⁷ , W ⁸ or a cycle formed from two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ can each independently carry one, two, three or four identical or different groups R ^a ;

saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl containing one, two, three or four heteroatoms selected from N, O and S, which may carry 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 -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ -Al kinyl, C ₂ -C ₈ - haloalkynyl, C ₄ -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 ₂ -C ₈ -haloalkynyloxy, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₃ -C ₈ -cycloalkoxy, C C ₃ -C ₈ halocycloalkoxy, C 1 -C ₈ -cycloalkenyloxy, C 1 -C 10 -cycloalkyl, C 1 -C ₈ -alkylcarbonyloxy, C 1 -C ₈ -alkoxycarbonyloxy, aminocarbonyloxy, C 1 -C ₈ -alkylaminocarbonyloxy, C 1 -C ₈ -alkylaminocarbonyloxy, C 1 -C ₈ -alkylthiocarbonyloxy, -CS-Alkoxythiocarbonyloxy, Aminothiocarbonyloxy, Ci-C ₈ alkyl aminothiocarbonyloxy, di-Ci-Cs-alkylaminothiocarbonyloxy Ci-C ₈ -

Alkylaminothiocarbonyl, di-Ci-Cs-alkylaminothiocarbonyl, Ci-Cβ- alkylene, oxy-C ₂ -C ₄ -alkylene, oxy-C ₃ alkyleneoxy, = CH _2, = CH (Ci-C ₈ - alkyl), = C (C 1 -C ₈ -alkyl) 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) A, N (A) -C (= O) -A,

N (A ") -C (= O) -N (A) A, S (= O) _m -A, S (= O) _n -OA, S (= O) _n -N (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 the group 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, Ci-C ₈ alkyl, C ₂ -C ₈ alkene yl, C ₂ -C ₈ kinyl -alkyl, C ₄ -Cio-alkadienyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ -CyCIo- alkenyl, Cs-Cio-bicycloalkyl, C ₈ alkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ - alkynyloxy, _C3-C8 cycloalkoxy, C3 -C ₈ -cycloalkenyloxy, Aminothiocar- carbonyl, d-Cs-alkyl-carbonyloxy, Ci-Cs-alkylaminothiocarbonyl, di-Cr Cs-alkylaminothiocarbonyl, _Ci-C8 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-C ₁ -C ₆ -alkoxy, Ce-Cu-aryl-C ₁ -C ₄ -alkyl, alkyl, five- to ten-membered saturated, 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 ¹ X = N-OA), N (A') A; can be substituted where the aliphatic, alicyclic or aromatic groups logeniert partially or fully HA and / or ₈ alkyl and / or Ci-C groups by C ₈ haloalkyl;

where m, n, A, A 'and A "mean:

m is 0, 1 or 2;

n 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 kinyl -alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ Cycloalkenyl or phenyl, wherein the organic radicals may be partially or completely halogenated and / or may be monosubstituted or polysubstituted, preferably one to four times, by nitro, cyanato, cyano, C 1 -C ₄ -alkoxy; A and A 'can also be used together with the atoms to which they are bonded for 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 may carry 1 or 2 identical or different substituents R ^a , wherein R ^{a is} as defined above;

R ² is hydrogen, halogen, cyano, d-Cβ-alkyl, d-Cβ-haloalkyl, _{Ci-C8-alkoxy,} Ci-Cs-haloalkoxy, _Ci-C8 alkylthio, _{Ci-C8-alkylsulfinyl,} Ci -C ₈ -Al kylsu If onyl, C3-C8-cycloalkyl, _C3-C8 halocycloalkyl; wherein R ² may contain one, two, three or four identical or different groups R ^a and R ^{a is} as defined above;

X is hydrogen, halogen, hydroxy, cyano, N (A ') A, C ₈ alkoxy, Ci-Cs-haloalkoxy, Ci-Cβ alkylthio, _{Ci-C8-alkylsulfinyl,} Ci-C ₈ alkylsulfonyl, C kyl -C ₈ -alkyl, Ci-C ₈ haloalkyl, C ₂ -C ₈ -alkenyl -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ kinyl -alkyl, C ₂ -C ₈ - haloalkynyl, cyano C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; wherein A and A are as defined above;

Y - 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, said heterocycle being 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 -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ Alkynyl, C ₂ -C ₈ -

Haloalkynyl, C4-Cio-alkadienyl, C4-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-C8} cycloalkenyl, C3 -C ₈ halocycloalkenyl, C 3 -C ₈ cycloalkoxy,

C 3 -C 6 -cycloalkenyloxy, hydroxyimino-C 1 -C ₈ -alkyl, C ₁ -C 6 -alkylene, oxy-C ₂ -C 4 -alkylene, oxy-C ₁ -C 3 -alkylenoxy, C ₁ -C ₈ -alkoximino-C 1 -C ₈ - alkyl, C ₂ -C ₈ -Alkenyloximino-Ci-Cs-alkyl, C ₂ -C ₈ -Alkinyloximino-Ci-C ₈ alkyl, S (= O) _m A ¹ , C (= O) A ² , C (= S) A ² , NR ⁵ R ⁶ , NR ⁵ O = 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 the group oxygen, nitrogen and sulfur; where m, A ¹ , A ² , R ⁵ , R ⁶ ,

R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ mean:

m is 0, 1 or 2;

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

C 1 -C ₈ -alkylamino or C 1 -C ₈ -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 ₂ -C ₈ -haloalkynyl, C ₁ -C -alkoxy, C ₁ -C -haloalkoxy, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -

Haloalkenyloxy, C2-C8-alkynyloxy, C2-C8 haloalkynyloxy, Ca-Cs-cycloalkyl, _{C3-C8-halocycloalkyl, C3-C8} cycloalkoxy, C3-C8-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 -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₈ -cycloalkenyl or C 3 -C ₈ halocycloalkenyl,

R ⁵ and R ⁶ , R ⁸ and R ⁹ , R ¹⁰ and R ¹¹ and / or R ¹² and R ¹³ may also be taken together with the nitrogen atom to which they are attached, a four-, five- or six-membered saturated or partially unsaturated Ring which is unsubstituted or substituted with one, two, three or four identical or different substituents R ^a , wherein R ^{a is} as defined above;

wherein the aliphatic and / or alicyclic and / or heterocyclic groups of the radical definitions of L in turn may carry one, two, three or four identical or different groups R ^L ;

R ^{L is} halogen, cyano, Ci-C ₈ alkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ -alkyl kinyl- oxy, _C3-C8 cycloalkyl, _C3-C8 cycloalkenyl, C3-C ₈ cycloalkyloxy, C3-C ₈ - cycloalkenyloxy, C ₈ -Alkoximino, C ₂ -C ₈ -Alkenyloxyimino, C ₂ -C ₈ -

Alkinylxyimino, Ci-C ₈ -Alkoximino-C ₈ alkyl, C ₂ -C ₈ -Alkenyloximino- Ci-C ₈ alkyl, C ₂ -C ₈ -Alkinyloximino-Ci-C ₈ 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- C3 alkyleneoxy, wherein R ^{a is} as defined above;

Z is C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl, C ₂ -C 10 -alkynyl, C ₂ -C 10 -haloalkynyl, C ₃ -C 12 -cycloalkyl, C ₃ -C 12 -halocycloalkyl , C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocycloalkenyl, phenyl, halophenyl,

Naphthyl, halonaphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic carbon-bonded heterocycle containing one, two, three or four heteroatoms from the group oxygen, nitrogen and Sulfur, or Ci-C ₄ -AlkVl, by 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 is substituted oxygen, nitrogen and sulfur, which may carry 1, 2 or 3 radicals R ^a ; wherein Z may contain one, two, three or four identical or different groups R ^a ; wherein R ^{a is} as defined above;

and the agriculturally or pharmaceutically acceptable salts thereof.

The invention further relates to processes and intermediates for the preparation of the compounds according to the invention and those used according to the invention, to fungicidal or pharmaceutical agents containing them and to their use for controlling phytopathogenic harmful fungi or for the treatment of cancer.

From WO 02/48151, WO 04/000844, WO 05/000851, WO 05/056555, WO 05/056556, WO 05/056557, WO 05/056558, WO 05/056559 and WO 05/082907 are 7-aminopyran zolopyrimidines generally known. These compounds are known for controlling harmful fungi.

The effect of the known compounds is unsatisfactory in many cases. On this basis, the present invention has the object to provide novel compounds having a suitable fungicidal activity against phytopathogenic fungi, which are improved at least in some areas over known compounds and z. B. have a better fungicidal activity and / or a broadened spectrum of activity.

In addition, new compounds with an improved pharmacological action are to be provided. Accordingly, the compounds defined at the outset, the fungicidal compositions containing them, their use and the method of preparation thereof have been found.

The compounds of the invention are also pharmacologically active. Accordingly, the invention also relates to pharmaceutical compositions containing the compounds of the invention and / or a pharmaceutically acceptable salt thereof and their use for the treatment of tumor diseases.

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 activity of the compounds according to the invention.

So 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 according to the invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

Suitable pharmaceutically acceptable salts are, in particular, physiologically tolerated salts of compound I, in particular the acid addition salts with physiologically tolerated acids. Examples of suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, C 1 -C 4 -alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid. Further suitable acids are, for example, in progress in drug research, Volume 10, pages 224 et seq., Birkhäuser

Verlag, Basel and Stuttgart, 1966, which is hereby incorporated by reference in its entirety. The compounds according to the invention or compounds used according to the invention can be obtained in various ways. They are advantageous by coupling of 5,7-Diha inden of the formula II

with organometallic reagents M ^w (-Z) _w , whereby the substituent Z can be introduced in the 7-position, so that compounds of the formula I are obtained, in which X is halogen:

R ¹ , R ² , Y and Z have the meanings or preferred meanings as given for the compounds of the formula I and Hal is halogen, preferably fluorine, chlorine or bromine. M represents a metal ion of valence w, such as B, Zn, Mg or Sn. This reaction can be carried out, for example, by the following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid., 2345 (1996); WO-A 99/41255; Aust. J. Chem., Vol. 43, 733 (1990); J. Org. Chem., Vol. 43, 358 (1978); J. Chem. Soc. Chem. Commun. 866 (1979); Tetrahedron Lett, Vol. 34, 8267 (1993); ibid., Vol. 33, 413 (1992).

According to one embodiment of this process, the reaction takes place under transition metal catalysis, such as. B. Ni or Pd catalysis.

Starting from compounds of formula I wherein X is halogen, corresponding compounds in which X is hydroxy, cyano, _{Ci-C8-alkoxy, Ci-C8-halo-alkoxy,} Ci _-C8-Al alkylthio, Ci-C ₈ -alkylsulfinyl or C 1 -C ₈ -alkylsulfoxyl. For example, compounds of the formula I in which X is halogen, preferably chlorine, can be reacted therewith with compounds A ^a B ^b . A ^a in the compounds A ^a B ^b represents a cation, B ^b is hydroxide, cyanide, Ci-C ₈ alkoxylate, C ₈ - haloalkoxides or C ₈ -Alkylthiolat. Thus, depending on the group to be introduced, the compounds A ^a B ^b are a hydroxide, inorganic cyanide (for example KCN, NH ₄ CN), a (halogen) alkoxylate or a thiolate. The cation A ^a has little significance and there are such different types into consideration. For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred.

Compounds of the formula I in which X is C 1 -C ₈ -alkylsulfinyl or C 1 -C ₈ -alkyl-cyanoalkyl may then be prepared starting from the corresponding compounds of the formula I where in X is C 1 -C ₈ -alkylthio, can be obtained by oxidation. The reaction conditions for such oxidation are well known to those skilled in the art.

The reaction with A ^a B ^b is preferably carried out in an inert solvent. Suitable solvents include ethers such as dioxane, diethyl ether, methyl tert-butyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons such as dichloromethane or dichloroethane, aromatic hydrocarbons such as toluene, and mixtures thereof.

The reaction temperature is usually 0 to 120 ^° C., preferably 10 to 40 ^° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].

Compounds of the formula I in which X denotes N (A ') A can likewise be obtained starting from compounds of the formula I in which X denotes halogen, preferably chlorine, by reacting these with the corresponding amine NH (A') A.

The inventive compounds of the formula I, wherein X is Ci-C ₈ alkyl, C ₈ - haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, halo-C ₂ -C ₈ alkynyl, cyano-C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, may also be prepared in an advantageous manner from compounds of the formula I in which X is halogen, in particular chlorine or bromine, by this ₂ -C -alkenyl with an organometallic compound MX ^a wherein M is lithium, magnesium or zinc and X ^a is Ci-Cs-alkyl, Ci-C ₈ haloalkyl, C ₈ -alkyl, C ₂ -C ₈ haloalkenyl , C kinyl ₂ -C ₈ -alkyl, C ₂ -C ₈ - haloalkynyl, cyano-Ci-C4-alkyl or Ci-C4-alkoxy-Ci-C4-alkyl, are reacted. Particularly advantageously, the formula I ₈ alkyl, C ₂ -C ₈ alkenyl or C can in this way by using the corresponding compounds MX ^a compounds are prepared wherein X ^a is C ₂ -C ₈ -alkynyl stands.

The reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (I) iodide.

The reaction is preferably carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.

The preferred temperatures for the reaction are in the range of -100 to + 100 ° C, in particular in the range of -80 ° C to + 40 ° C. Methods for this are known, for. B. from the cited prior art (see, for example, also WO 03/004465). 5,7-Dihalogenpyτazolopyτimidine of formula II can be obtained, for example, by the corresponding 5, the formula III

in analogy to the cited prior art or according to the methods described in WO-A 94/20501 is reacted with a halogenating agent. R ¹ , R ² and Y here have the meanings or preferred meanings as given for the compounds of formula I.

The halogenating agents used are preferably phosphorus oxyhalide or phosphorus (V) halide, for example phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride with phosphorus pentachloride. It may be advantageous to use a hydrohalide of a tertiary amine, e.g. B. triethylamine hydrochloride, as a cocatalyst.

The halogenation reaction of compounds of formula III to give compounds of the formula II is usually carried out at temperatures from 0 ° C to 150 ° C, preferably from 80 ⁰ C to 125 ° C [see also EP-A 770 615].

The reaction may be carried out in bulk or in an inert solvent, e.g. A halogenated hydrocarbon such as dichloromethane, dichloroethane or an aromatic hydrocarbon such as toluene or o-, m-, p-xylene or in a mixture of said solvents.

5,7-Dihydroxypyrazolopyrimidines of the formula III can be prepared in various ways, for example in analogy to those described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993).

For example, 5,7-dihydroxypyrazolopyrimidines of the formula III can be prepared by reacting the correspondingly substituted malonate of the formula IV

with an aminopyrazole of the formula V

is reacted, wherein Y, R ¹ and R ^{2 is} as defined for formula I or preferably described and R is alkyl, preferably (C 1 -C 6) -alkenyl, in particular methyl or ethyl. The reaction of aminopyrazole of the formula V with a malonate IV is usually carried out at temperatures of 80 ° C to 250 ° C, preferably from 120 ° C to 180 ° C, also preferably from 80 ° C to 180 ° C.

Preferably, the reaction is carried out without solvent or an inert organic solvent can be used, for example an aprotic polar solvent. The reaction can be carried out in the presence of a catalyst, for example a base [cf. EP-A 770 615]. Furthermore, it may also be preferable to react in the presence of an acid, for example a carboxylic acid such as. Acetic acid or using a corresponding acid addition salt of V, for example the sulphate of V, under conditions well known to those skilled in the art.

Suitable solvents are, for example, aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.

The reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide or N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned. Optionally, catalytic amounts of acids, such as p-toluenesulfonic acid, acetic acid or propionic acid, may also be added.

Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal hydrogen carbonates such as, for example, potassium carbonate, organometallic compounds, in particular alkali metal alkyls, alkylmagnesium halides and alkali metal hydroxides. and alkaline earth metal alkoxides and dimethoxy magnesium, as well as organic bases, e.g. B. tertiary amines such as trimethylamine, triethylamine, diisopropylethyl amine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particular preference is given to using tertiary amines, such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.

The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent. The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the malonate IV in excess, based on the aminopyrazole of the formula V.

Amino pyrazoles of formula V can be prepared, for example, in analogy to the methods described in Journal of Organic Chemistry, 44 (5), 818-824, 1979 and Journal of Organic Chemistry, 59 (24), 7299-7305, 1994.

Malonates of the formula IV in which Y is optionally substituted aryl or optionally substituted heterocyclyl, in particular heteroaryl, as defined for formula I, starting from corresponding aryl or heteroaryl compounds of the formula VI

by reaction with one or two Äquivalen ^v th ^ι a Kohlensäureesters or a chloroformate of the formula VII n

in the presence of a strong base, where R ^{z is} hydrogen or a (C 1 -C 4) -alkoxycarbonyl group, Y is optionally substituted aryl or optionally substituted heteroaryl, as defined for formula I, Q is halogen or ( C1-C4) - alkoxy, in particular methoxy or ethoxy, and R is (Ci-Ce) alkyl.

Those skilled in the art will recognize that in the case of R ^z = H, at least 2 equivalents of Compound VII must be used to achieve complete conversion of Compound VI.

The reaction described above is usually carried out in the presence of strong bases. If R ^{z is} hydrogen, it is usual to use alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base. In this case, the base will be used at least equimolar with respect to compound VI in order to achieve complete conversion. If R ^{z is} an alkoxycarbonyl group, it is preferable to use an alkali metal alcoholate, e.g. As sodium or potassium, sodium or potassium butoxide, sodium or potassium as a base. When R ^{z is} hydrogen, the reaction of compound VI with compounds of formula VII can be carried out in one stage or in two separate stages, in which latter case the intermediate VI is obtained in which R ^{z is} an alkoxycarbonyl group. Incidentally, the reaction of compound VI with VII can be carried out in analogy to the method described in J. Med. Chem. 25, 1982, p. 745. The preparation of malonates of the formula IV also succeeds advantageously by reaction of corresponding bromo- (hetero) aryl compounds with dialkylmalonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].

Malonates of the formula IV in which Y is optionally substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 3 -C 12 -cycloalkenyl, as defined for formula I, can be prepared starting from of dicarbonyl compounds IVa

in which R is C 1 -C 6 -alkyl, preferably C 1 -C ₄ -alkyl, in particular methyl or ethyl, by reaction with a base and a corresponding compound Hal-Y, where Hal is halogen, preferably chlorine, bromine or iodine, and Y is optionally substituted Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₂ -cycloalkyl or C ₃ -C ₂ -cycloalkenyl, as defined for formula I. The reaction can be carried out analogously to the procedure described in the Organikum, 22nd edition, Wiley-VCH Verlag GmbH & Co. KGaA, pages 608-609.

The reaction is preferably carried out at 0 ° C to 120 ° C. Examples of suitable bases are alkali metal alcoholates (such as, for example, methanolates, ethanolates and isopropanols of the alkali metals such as, for example, sodium or potassium), alkali metal hydrides, such as, for example, For example, sodium hydride, potassium hydride or lithium hydride, alkali metal amides such. As lithium amide, sodium amide or lithium diisopropylamide (LDA) can be used.

Suitable solvents for this reaction are preferably alcohols such. As methanol or ethanol, but also acetonitrile, DMSO, DMF, as will be apparent to those skilled.

Compounds of formula I can be further prepared by the appropriately substituted carbonyl IVb

is condensed with an aminopyrazole of the formula V as defined above, wherein X, Y, Z are defined as described for formula I or preferably described (see WO 03/004465). This reaction is usually carried out at temperatures of from 80 ° C. to 250 ° C., preferably from 120 ° C. to 180 ° C., without solvent or in an inert organic solvent in the presence of a base (cf., EP-A 770 615) or in the presence of acetic acid among those from Adv. Het. Chem. Bd. 57, p. 81ff (1993) (see above). Suitable solvents are, for example, aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide. The reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide or

N-methylpyrrolidone carried out. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are generally inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates, and alkali metal hydrogencarbonates, such as, for example, potassium carbonate, organometallic compounds, in particular alkali metal alkyls, alkylmagnesium halides and alkali metal hydroxides. and alkaline earth metal alkoxides and dimethoxymagnesium, also organic see bases, for. B. tertiary amines such as trimethylamine, triethylamine, diisopropylethyl amine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particular preference is given to using tertiary amines, such as triethylamine, triisopropylethylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.

The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the dicarbonyl compound IVb in excess, based on the aminopyrazole of the formula V.

Carbonyl compounds of the formula IVb can be prepared, for example, by adding a compound IVc

by reaction with a base and a corresponding compound Hal-Y, where Hal is halogen, preferably chlorine, bromine or iodine, X is Ci-Ce-Al kyl, Ci-Cs haloalkyl, C2-C8 alkenyl, C2-C8 Haloalkenyl, C ₂ -C 5 -alkynyl or C ₂ -C 8 -haloalkynyl, Z is C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -alkoxy

Haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl or C 3 -C 12 -halocycloalkenyl, as defined for formula I, and Y for optionally substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl or C 3 -C 12 -cycloalkenyl, as defined for formula I [cf. Organikum, 22nd edition, Wiley-VCH Verlag GmbH & Co. KGaA, pp. 608-609 and analogous reaction description above]. Compounds of formula I, wherein X is Ci-C ₈ alkyl, _Ci-C8 haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8 alkynyl, C2-C8-haloalkynyl, cyano-Ci- C4-alkyl or Ci-C4-alkoxy-Ci-C4-alkyl, for example, can also be prepared by a 7-Halogenpyrazolopyrimidin of formula IIa

is coupled with an organometallic reagent M ^w (-Z) _w , whereby the substituent Z is introduced in the 7-position (see above), wherein Hal is halogen, X is Ci-Cs-alkyl, Ci-Cs-haloalkyl , C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, cyano-C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy Ci-C ₄ alkyl and Y, R ¹ and R ^{2 have} the meanings given for compounds of formula I.

7-Halogenpyrazolopyrimidines of the formula IIa can be obtained by reacting the corresponding 7-hydroxypyrazolopyrimidine of the formula MIa

is reacted with a halogenating agent, wherein R ¹ , R ² , X and Y have the meanings as given for the compounds of formula IIa.

The halogenation is carried out in analogy to the cited prior art or according to the methods described in WO-A 94/20501 or as set forth above for the reaction of compounds of formula M1 with a halogenating agent.

7-Hydroxypyrazolopyrimidines of the formula MIa can be prepared in analogy to those described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993).

Compounds of formula IMa can be obtained by using a compound of the

Formula IVd

with an aminopyrazole of the formula V

where X, Y, R ¹ and R ^{2 are defined} as described for formula I or IMa or preferably and R is alkyl, preferably (Ci-C6) alkyl, in particular methyl or ethyl.

The reaction of an aminopyrazole of the formula V with a compound of the formula IVd is carried out analogously to the above-described reaction of compounds of the formula IV with a compound V.

Compounds of the formula IVd can be prepared analogously to standard processes in the sense of a mixed ester condensation from the corresponding substituted acetic esters by reaction with the corresponding aliphatic (C 2 -C 8) -carboxylic acid alkyl esters such as ethyl acetate, ethyl propionate, ethyl butyrate or ethyl valerate or with a reactive derivative thereof, for , As an acid chloride or an acid anhydride, in the presence of a strong base, for. An alkoxide, an alkali metal amide or an organolithium compound, for example, in analogy to that described in J. Chem. Soc. Perkin Trans 1967, 767 or Eur. J. Org. Chem. 2002, p. 3986.

Compounds of the formula I in which X is C 1 -C 8 -alkyl can also be prepared by reacting in a first step a compound of the formula I in which X is halogen, in particular chlorine or bromine, with a malonate of the formula IVe

X "

IVe

OR OR to a connection of the form

wherein X "is hydrogen or C 1 -C ₇ -alkyl and R is C 1 -C ₄ -alkyl and Y, Z, R ¹ and R ^{2 are} as defined for compounds of formula I. The compound of formula VI is hydrolyzed and the hydrolysis product is decarboxylated [see US 5,994,360].

The malonates IVe are known from the literature, for. From J. Am. Chem. Soc., Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the cited literature.

The subsequent hydrolysis of the ester VI takes place under conditions which are generally known to the person skilled in the art. Depending on the various structural elements, the alkaline or acidic hydrolysis of the compounds VI may be advantageous. Under the conditions of ester hydrolysis, the decarboxylation to the compounds of the formula I can already take place completely or partially. The decarboxylation is usually carried out at temperatures from 2O ⁰ C to 18O ⁰ C, preferably 5O ⁰ C to 12O ⁰ C. Preferably, the decarboxylation is carried out in an inert solvent, optionally in the presence of an acid. Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.

Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether , Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide, Dimethylformamide and dimethylacetamide, most preferably the reaction is carried out in hydrochloric acid or acetic acid. It is also possible to use mixtures of the solvents mentioned.

Another object of the present invention are compounds of formula VI

wherein X "is hydrogen or C 1 -C ₇ -alkyl and R is C ¹ -C ₄ -alkyl and Y, Z, R ¹ and R ^{2 are} as defined for compounds of the formula I.

The reaction mixtures are worked up in the usual way, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products. The intermediate and end products fall z. T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.

If individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I or they are accessible analogously to the compounds whose syntheses are described in the literature cited above.

However, if isomeric mixtures are involved in the synthesis, separation is generally not required because some of the isomers may partially interconvert during processing for use or in use (eg, exposure to light, acids, or bases) , Corresponding transformations may also take place after application, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.

In the definitions of the symbols given in the above formulas, collective terms have been used that are generally representative of the following substituents:

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. C 1 -C ₈ -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3 Methyl butyl, 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, 1-ethyl-2-methyl-propyl, heptyl, octyl and 2-ethylhexyl;

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 3) -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.

C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl: C 1 -C -alkyl as mentioned above, where one or more hydrogen atoms, preferably a hydrogen atom, have been replaced by C 1 -C -alkoxy groups as defined below. C 1 -C 8 -alkenyloxy-C 1 -C 8 -alkyl: C 1 -C 8 -alkyl as mentioned above, where one or more hydrogen atoms, preferably a hydrogen atom, have been replaced by C 2 -C -alkenyloxy groups as defined below.

Ci-Cs-alkynyloxy-d-Cs-alkyl: Ci-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by C2-Cs-alkynyloxy groups as defined below.

C3-C8-Cycloalkyloxy-Ci-C8-alkyl: Ci-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by as defined below drdi-cycloalkyloxy groups.

d; -d4-aryl-d-di-alkyl: d-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by C6-C14-aryl groups as defined below.

Ce-Cu-aryloxy-Ci-Cs-alkyl: Ci-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by as defined below C6-Ci4-aryloxy groups.

Benzyloxy-d-Cs-alkyl: Ci-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by benzyl groups.

Cyano-d-di-alkyl: Ci-Cs-alkyl as mentioned above, wherein one or more hydrogen atoms, preferably a hydrogen atom, are replaced by cyano groups (CN).

Hydroximino-d-di-alkyl: radical of the formula RCH = NOH, where R is a single bond or a Ca-d-alkylene radical.

Ci-Cs-alkoximino-Ci-Cs-alkyl: radical of the formula RCH = NOR ', wherein R is a single bond or a Ca-d-alkylene radical and R' is Ci-Cs-alkyl.

Alkenyl and the alkenyl moieties in assembled groups, such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having preferably 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-butenyl, 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 compound 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, for. 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 in assembled 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, for. 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; as well as 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 F5, 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; z. C ₃ -C 8 alkenyloxy such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3 Pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl 2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyl,

1, 1-dimethyl-2-propenyloxy, 1, 2-dimethyl-1-propenyloxy, 1, 2-dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy, 3-methyl-1-pentenyloxy, 4-methyl-1-pentenyloxy, 1 - Methyl 2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3 pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1, 1-dimethyl-2 butenyloxy, 1, 1-dimethyl-3-butenyloxy, 1, 2-dimethyl-1-butenyloxy, 1, 2-dimethyl-2-butenyloxy, 1, 2-dimethyl-3-butenyloxy, 1, 3-dimethyl-1 - butenyloxy, 1, 3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-1-butenyloxy, 2,3-dimethyl-2- butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3-dimethyl-2-butenyloxy, 1-ethyl-1-butene yloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-1-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1, 1, 2-trimethyl 2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy,

1-ethyl-2-methyl-1-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy.

Haloalkenyloxy: alkenyloxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkenyl, in particular fluorine, chlorine or bromine, z. Chlorovinyloxy, chloroallyloxy and the like.

Alkynyloxy: alkynyl as mentioned above, which is bonded via an oxygen atom, for. B. C3-C6 alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1 - Methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl 3-pentynyloxy and the like.

Haloalkynyloxy: an alkynyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine.

Cycloalkoxy: Cycloalkyl, as mentioned above, which is bonded via an oxygen atom, z. C 3 -C 10 cycloalkoxy or C 1 -C 8 cycloalkoxy such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy and the like. Halocycloalkoxy: Halocycloalkyl, as mentioned above, which is bonded via an oxygen atom.

Cycloalkenyloxy: Cycloalkenyl, as mentioned above, which is bonded via an oxygen atom, for. C3-Cio-Cycloalkenyloxy, Ca-Cs-Cycloalkenyloxy or preferably C5-C6-Cycloalkenyloxy, such as cyclopent-1-enoxy, cyclopent-2-enoxy, cyclohex-1-enoxy and cyclohex-2-enoxy.

Halocycloalkenyloxy: Halocycloalkenyl, as mentioned above, which is bonded via an oxygen atom.

Alkylthio: alkyl as defined above attached via an S atom;

Bicycloalkyl: bicyclic hydrocarbon radical containing 5 to 10 carbon atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl,

Bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl, decalin and the like.

Aryl: carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl. C6-Cio-aryl is phenyl or naphthyl.

Aryloxy: O-linked carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenoxy, naphthyloxy, anthracenyloxy or phenanthrenyloxy. C6-Cio-aryloxy is phenoxy or naphthoxy.

Arylalkoxy: alkoxy as defined above, wherein a hydrogen atom is replaced by an aryl group, e.g. Benzoxy, 2-phenylethoxy and the like.

Arylthio: carbons bound via S carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenylthio, naphthylthio, anthracenylthio or Phenanthrenylthio. C6-Cio-arylthio stands for phenylthio or naphthylthio.

C 1 -C 8 -alkylcarbonyl: radical of the formula RC (O) -, in which R is C 1 -C ₈ -alkyl.

C 1 -C 8 -alkoxycarbonyl: radical of the formula R-OC (O) -, in which R is C 1 -C ₈ -alkyl. C 1 -C 8 -alkylcarbonyloxy: radical of the formula RC (O) -O-, in which R is C 1 -C ₈ -alkyl.

C 1 -C 8 -alkoxycarbonyloxy: radical of the formula ROC (O) -O-, in which R is C 1 -C ₈ -alkyl.

Aminocarbonyl: radical of the formula NHb-C (O) -.

C 1 -C ₈ -alkylaminocarbonyl: radical of the formula RNH-C (O) -, in which R is C 1 -C ₈ -alkyl.

Di (Ci-C8-alkyl) -aminocarbonyl: radical of the formula RR'N-C (O) -, in which R and R 'are independently of Ci-Cs-alkyl.

Aminocarbonyloxy: radical of the formula NHb-C (O) -O-. C 1 -C ₈ -alkylaminocarbonyloxy: radical of the formula RNH-C (O) -O-, in which R is C 1 -C ₈ -alkyl.

Di (Ci-C8-alkyl) -aminocarbonyloxy: radical of the formula RR ¹ NC (O) -O-, wherein R and R 'are independently d-Cs-alkyl. C 1 -C ₈ -alkylthiocarbonyl: radical of the formula RC (S) -, in which R is C 1 -C ₈ -alkyl.

C 1 -C 8 -alkoxythiocarbonyl: radical of the formula R-OC (S) -, in which R is C 1 -C ₈ -alkyl.

C 1 -C ₈ -alkylthiocarbonyloxy: radical of the formula RC (S) -O-, in which R is C 1 -C ₈ -alkyl.

C 1 -C 8 -alkoxythiocarbonyloxy: radical of the formula ROC (S) -O-, in which R is C 1 -C ₈ -alkyl. Aminothiocarbonyl: radical of the formula NHb-C (S) -.

Ci-Cs-Alkylaminothiocarbonyl: radical of the formula RNH-C (S) -, wherein R is Ci-C ₈ alkyl.

Di (Ci-C8-alkyl) -aminothiocarbonyl: radical of the formula RR'N-C (S) -, wherein R and R 'are independently Ci-Cs-alkyl. Aminothiocarbonyloxy: radical of the formula NH 2 -C (S) -O-.

C 1 -C ₈ -alkylaminothiocarbonyloxy: radical of the formula RNH-C (S) -O-, in which R is C 1 -C ₈ -

Alkyl stands.

Di (Ci-C8-alkyl) -aminothiocarbonyloxy: radical of the formula RR ¹ NC (S) -O-, wherein R and R 'are independently Ci-Cs-alkyl. C 1 -C ₈ -alkylsulfinyl: radical of the formula RS (O) -, in which R is C 1 -C ₈ -alkyl.

C 1 -C ₈ -alkylsulfonyl: radical of the formula RS (O) ₂ -, in which R is C 1 -C ₈ -alkyl.

C 1 -C ₈ -alkylsulfonyloxy: radical of the formula RS (O) ₂ -O-, in which R is C 1 -C ₈ -alkyl.

Alkylene: divalent linear chains of CH ₂ groups. Preference is given to (C ₁ -C ₆ ) -alkylene, more preferably (C ₂ -C ₄ -alkyl), and furthermore it may be preferable to use (C ₁ -C ₃ ) -alkylene groups Examples of preferred alkylene radicals are CH ₂ , CH _{3 2} CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ (CH ₂ ) ₂ CH ₂ , CH ₂ (CH ₂ ) ₃ CH ₂ and CH ₂ (CH ₂ ) ₄ CH _2. (C ₂ -C ₇ ) alkylene represents - (CH ₂ ) _P ; p = 2, 3, 4, 5, 6 or 7.

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;

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 have a carbon atom or via a nitrogen atom, if included. 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 one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, wherein the heterocyclyl is C or N can be tied up;

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 can be: z. 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-2-yl, 2,4-dihydro-thien-3-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-isothiazolinone 4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-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-dihydrooxazol-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-hexahydrotriazin-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, besides 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, e.g. Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1, 2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and Thiadiazolyl, especially 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 -Oxadiazol-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 ring heteroaryl groups which, besides carbon atoms, have one to four or . One to three nitrogen atoms may contain as ring members, z. 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.

Metal equivalent stands for a monovalent cation equivalent of the formula (M ^{x +} ) i / _x , where x is 1, 2 or 3 and M is a metal (with the charge number x). It goes without saying that M stands for an agriculturally compatible metal. Preferably, M is a metal of the 1st main group (alkali metal), preferably lithium, sodium or potassium, the 2nd main group (alkaline earth metal), preferably magnesium, calcium or barium, or a transition metal, preferably manganese, copper, zinc or iron.

Within the scope of the present invention are the (R) and (S) isomers and the racemates of the compounds of the invention comprising chiral centers. The compounds according to the invention can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.

In the compounds of the formula I used according to the invention or according to the invention, the following meanings of the substituents, in each case alone or in combination, are particularly preferred. If appropriate, the preferred substituents or preferred combinations of substituents apply correspondingly to the precursors of the compounds according to the invention. In one embodiment, X is halogen, cyano, hydroxy, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-C ₈ alkyl, _{Ci-C8-haloalkyl,} or a group N (A) A.

According to a further embodiment of the invention, X is C 1 -C 6 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 5 -alkynyl, C 2 -C 5 -halogenoalkynyl, cyano- Ci-C4) -alkyl or (Ci-C4) -alkoxy- (Ci-C4) -alkyl. X is preferably C 1 -C 4 -alkyl, such as methyl, ethyl or n-propyl. Further preferred X is C 1 -C 4 -haloalkyl, 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.

Another embodiment relates to compounds I in which X is halogen, in particular chlorine.

According to another preferred embodiment of the present invention, X is C 1 -C 8 -alkoxy, preferably C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. Furthermore, X is preferably C 1 -C 8 -haloalkoxy, preferably C 1 -C 4 -haloalkoxy.

Further preferably, X is hydroxy.

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

In a further preferred embodiment, X is cyano- (C ₁ -C 4) -alkyl, preferably cyano- (C ₁ -C ₂ ) -alkyl, in particular -CH ₂ -CN.

Further preferably, X is N (A ') A. Preferably, A and A 'together with N represent a piperidine or pyrrolidine radical which may be unsubstituted or preferably substituted by C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and in particular by methyl. In a further embodiment of the invention, X is (C 1 -C 4) -alkoxy- (C 1 -C 4) -alkyl, in particular (C 1 -C 2) -alkoxy- (C 1 -C 2) -alkyl, such as methoxymethyl, or (C 1 -C 4) Alkyl, in particular n-propyl, ethyl or methyl.

Preferably, 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 pyrazolopyrimidine skeleton.

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 above carbon bonded to the pyrazolopyrimidine skeleton. In another embodiment, the heterocycle is attached to the pyrazolopyrimidine skeleton via nitrogen. This also applies to the further embodiments of this embodiment of the invention described below. According to 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 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-Ci-C ₄ alkyl, Ci -C ₄ alkyl , Ci-C ₄ alkoxy, _{Ci-C4-haloalkoxy, Ci-C4} -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 Preferably, Y here means an unsubstituted or substituted five-, six- or seven-membered saturated or partially unsaturated heterocycle having one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or Contains 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 compounds I, wherein Y is an optionally substituted by L aromatic heterocycle, preferably a five- or six-membered aromatic heterocycle.

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 1, 2 or 3 substituents L can carry. Of these, 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 aspect, Y represents N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1, 2,4-triazolyl or N-pyrrolyl (N-azolyl means that the azole ring is attached via a ring nitrogen atom) 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, 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-dimethylpyrazol-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, methoxyiminoethyl 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-tiazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazol-1-yl, 3 -Trifluoromethyl-1, 2,4-tιϊazol-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-triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazole 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-tiazol-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 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, each of which is 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 may optionally contain one, two, contains three or four substituents L. Among them, compounds wherein Y is 2-pyridinyl, 3-pyridinyl or 4-pyridinyl which is unsubstituted or contains one or two substituents L are preferable. 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-methylpyridine -2-yl, 6-methylpyridin-2-yl, 2-chloropyridin-3-yl, 2-bromopyridin-3-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-trimethylpyridine-3 -yl, 2,4-dichloro-6-methylpyridin-3-yl, 3-chloropyrid in-4-yl, 3-bromopyridin-4-yl, 3-methylpyridin-4-yl, 3,5-dichloropyridine-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 -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 -methylpyrimidin-4-yl, 5-fluoro-6-methylpyrimidin-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.

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, which can be similar or different. In this case, L in each case independently has one of the meanings 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 ,

N (CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ ) (= 4-methylpiperidin-1-yl), 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, 2-fluoro-3-methoxyphenyl, 2,6- Difluoro-4- (methylpiperidin-1-yl) -phenyl or 4- (4-methylpiperidin-1-yl) -phenyl.

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, trichloroethyloxy, trifluoroethinyloxy, chloroallyloxy, iodopropproxyloxy, methylamino, ethylamino, n- Propylamino, i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetoxyloxy, methoxycarbonyl, ethoxycarbonyl, hydroxyiminoethyl, ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; and

1,3-linked 1,3-propanediyl, methylenedioxy (-O-CH ₂ -O-) and

1, 2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), where these radicals in turn one or more may carry 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 2, 4 and / or 6-position, which are independently selected from the L mentioned herein as preferred, in particular independently selected from fluorine, chlorine and 4- (4-methylpiperidin-1-yl).

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, with

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, carboxymethyl and

4- (4-methylpiperidin-1-yl).

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, Ci C ₄ -haloalkyl, in particular C 1 -C ₂ -fluoroalkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkoxycarbonyl, alkylaminocarbonyl, C 1 -C ₄ -alkylaminocarbonyl and C 1 -C ₄ -alkylaminocarbonyl, more preferably selected from nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy, methoxycarbonyl and amino carbonyl. 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.

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

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 -halogenoalkyl, 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 -halogenoalkenyloxy, 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 -halogenoalkenyloxyoff atoms which contain in each case 1 to 1 1 identical or different halogen atoms; in each case straight-chain or branched C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkylsulfonyloxy, hydroximino-C 1 -C 6 -alkyl or C 1 -C 6 -cycloalkyl alkoxyimino-Ci-C6 alkyl; - Ca-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-), wherein these radicals may be monosubstituted 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;

NR ⁵ R ⁶ , wherein preferably R ⁵ and R ⁶ together with N form a 5- or 6-membered saturated cycle which may be unsubstituted or substituted by a C 1 -C 4 -alkyl radical or C 1 -C 4 -haloalkyl radical.

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 -alkylenoxy, 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 düng is such a group 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 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, -C ₆ - alkylthio, Ci-C ₆ haloalkylthio, Ci-C ₆ alkylsulfinyl, d-Ce-haloalkylsulfinyl, -C ₆ - alkylsulfonyl, CrC ₆ haloalkylsulfonyl, -C ₆ alkylamino, di-CrC ₆ alkylamino, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ -alkyl kinyl, C ₂ - C ₆ alkynyloxy and oxy-CrC ₄ -alkylenoxy. 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 6 -cycloalkyl, C ₃ -C 6 -halocycloalkyl and -Si (C 1 -C 6 -alkyl) alkyl). 3 In a specific embodiment thereof, Y is Ci-Cio-haloalkyl, preferably Ci-Cδ-haloalkyl, in particular Ci-C4-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 position Y is group V.d:

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

V ¹ 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 (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 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 CCl 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 (CH) 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 (CH) 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 (CCb) ₂ , CF (CFs) ₂ ; substituted C ₃ -C ₄ -alkyl, such as CH (CH ₃ ) CH ₂ OH,

CH (CH ₃ ) CH ₂ OCHs, 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.

In a further embodiment, Y is (C 2 -C 10) -alkenyl, preferably (C 2 -C 6) -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: halo, cyano, nitro, hydroxy, d-Ce-alkyl, d-Cβ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C ₆ haloalkoxy, Ci-Ce-alkylthio, Ci-C ₆ haloalkylthio, Ci-C ₆ alkylsulfinyl, Ci-C ₆ - Haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylmino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ - Al kinyl, C ₂ -C ₆ alkynyloxy and oxy-Ci-C ₄ -alky- lenoxy. In particular, R ^a is selected here from: halogen, cyano, Ci-C ₄ -alkyl, Ci-C ₄ haloalkyl, _{Ci-C4-alkoxy-Ci-C4-alkyl,} Ci-C ₄ alkoxy, _Ci-C4- Haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl and -Si (C 1 -C 6 -alkyl) 3. In a particular embodiment thereof YC ₂ -Cio-haloalkenyl means C ₂ preferably -Cδ- haloalkenyl, 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 backbone and V ^1, V ² is hydrogen, halogen, _{Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-cyanoalkyl,} Ci-C ₄ hydroxyalkyl;

V ³ , V ⁴ Cs-Cs-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 represent, 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 (CHa) ₂ , C (CHa) 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 (CHa) ₂ , CH (CH ₃ ) CH (CHa) ₂ , CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) CH ₂ CH ₂ CH ₂ CH ₃ , CH ₂ CH (CH ₃ ) CH ₂ CH ₂ CH ₃ , CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₃ , CH (CH ₃ ) CH (CH ₃ ) CH ₂ CH ₃ , CH ₂ CH (CH ₂ CHS) ₂ or one of the groups mentioned above at V ¹ .

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 -Cio) -alkynyl, preferably (C ₂ -Ce) -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, _{Ci-C4-alkoxy-Ci-C 4} alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, _Ci-C4 alkoxy _{Ci-C4-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, 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 C ₁ -C 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 (CHa) ₂ , C (CHa) 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 (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 the groups mentioned above 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 C ₃ -C 8 -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 , wherein R ^{a is} as defined herein and is preferably each independently selected from: halogen, cyano, nitro, hydroxy, C ₁ -C ₆ alkyl, C i -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ - haloalkoxy, d-Ce-alkylthio, -C ₆ haloalkylthio, d-Ce-alkylsulfinyl, CrC ₆ - Haloalkylsulfinyl, Ci-C ₆ alkylsulfonyl, Ci-C ₆ haloalkylsulfonyl, Ci-C6-alkylamino, di-Ci-Ce-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 -alkyleneoxy. In particular, R ^a is selected here from: halogen, cya no, _{Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy,} CrC ₄ - 5 haloalkoxy, _C3-C6 cycloalkyl, _C3-C6 halocycloalkyl, and -Si (Ci-C ₆ alkyl). 3 In a particular embodiment thereof Y is Cs-Cs-halocycloalkyl, C3-C ₆ halocycloalkyl, preferably 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 position Y are the groups V.e to V.h:

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

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

20 V ² and V ³ in the group Ve independently of one another represent, for example, hydrogen; cyano; Halogen, such as chlorine or bromine; C 1 -C 3 -alkyl, such as CH 3, CH ₂ CHs; 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. 25

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

According to a specific embodiment of this embodiment, Y is cyclopropyl, cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl or 30 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:

_όö

According to another preferred embodiment, Y is an unsubstituted or substituted by R ^a , as defined above, C3-Cio-cycloalkenyl, preferably C3-C8-cycloalkenyl, in particular Cs-Cz-cycloalkenyl group. Y may here in each case 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, C ₁ -C ₆ alkyl, C i -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, -C ₆ oxy -AIk-, Ci-Cδ-haloalkoxy, d-Cδ-alkylthio, CrCδ haloalkylthio, CrCδ alkylsulfinyl, Ci-Cδ-haloalkylsulfinyl, alkylsulfonyl CrCδ , C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -alkylamino, di-C 1 -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 here from: halogen, cyano, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl,} -C ₄ - alkoxy, _Ci-4 haloalkoxy C , C ₃ -C 6 -cycloalkyl, C ₃ -C 6 -halocycloalkyl and -Si (C 1 -C 6 -alkyl) 3, in particular halogen and C 1 -C ₄ -alkyl. In a specific embodiment thereof, Y is C3-C6 halocycloalkenyl, which contains in each case one, two or three halogen atoms independently selected from fluorine, chlorine and bromine. In another specific embodiment thereof, Y is Cs-Cs-cycloalkenyl substituted by one, two or three methyl groups, preferably C3-C6-cycloalkenyl.

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.

According to a further preferred embodiment of the invention, Y is an optionally substituted imino group, in particular a group (B)

R ^a1

# ^ NR ^{a2 (B)} where # represents the point of attachment to the pyrazolopyrimidine skeleton. R ^a1 and R ^a2 independently of one another have the meanings given for R ^a , in particular those given for R ^a . R ^a1 and R ^a2 are preferably independently selected from among hydrogen, halogen, C 1 -C 5 -alkoxy, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 1 -C 6 -alkylamino and (Ci-C6-alkyl) amino, in particular selected from halogen, such as. Fluorine, chlorine and bromine; Ci-Cβ-alkyl, in particular methyl, ethyl, n-propyl and iso-propyl; Ci-Cβ-haloalkyl, in particular trichloromethyl, trifluoromethyl, 1, 1, 1-trifluoroethyl; Ci-Cδ-alkoxy, in particular methoxy, ethoxy and propoxy; and Ci-Cδ-haloalkoxy, such as. Trichloromethoxy, trifluoromethoxy and 1,1,1-trifluoroethoxy. It may be preferred that R ^{a1 is} different from hydrogen.

In the compounds of the formula I according to the invention Z is Ci-Cio-alkyl, C1-C10-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Ci2 Cycloalkyl, C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocycloalkenyl, phenyl, halophenyl, naphthyl, halonaphthyl or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated - ter or aromatic heterocycle bonded via carbon, containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur; wherein Z may contain one, two, three or four identical or different groups R ^a as defined herein. Z is preferably C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl , C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocyclo-alkenyl, naphthyl or halonaphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic carbon-bonded heterocycle, comprising two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, or C 1 -C ₄ -alkyl, which are represented by 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, which may carry 1, 2 or 3 radicals R ^a , more preferably C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkyl Alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, Cs-Cs-cycloalkyl, C3 -C8- halogenocycloalkyl, Cs-Cs-cycloalkenyl or Ca-Cs-halocycloalkenyl or C 1 -C 4 -alkyl which is represented by 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, which may carry 1, 2 or 3 radicals R ^a ; wherein Z may contain one, two, three or four identical or different groups R ^a as defined herein.

According to one embodiment of the invention, Z is C 1 -C 10 -alkyl, in particular C 1 -C 6 -alkyl, which is optionally substituted by one, two or three R ^a . R ^a is preferably selected from halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoximino, C 2 -C 6 -alkenyloximino, C 2 -C 6 -Alkinyloximino, C3-C6-cycloalkyl or Cs-Cδ-cycloalkenyl, wherein the aliphatic and / or alicyclic groups may in turn be substituted by one, two or three groups R ^b . R ^{b is} preferably independently halogen, cyano, C 1 -C 6 -alkyl, CΣrCβ alkenyl, C ₂ -C ₆ -alkyl kinyl, Ci-C ₆ alkoxy, Ci-C ₆ alkylcarbonyl or -C ₆ - haloalkylcarbonyl. According to one embodiment of this embodiment, Z is Ci-Cio-haloalkyl, in particular Ca-Cβ-haloalkyl.

According to another preferred embodiment of the invention Z is C2-C10-alkenyl, in particular C3-Cs-alkenyl which is optionally substituted by one, two or three R ^a is substituted, as defined herein.

According to a further preferred embodiment of the invention, Z is C2-C10-alkynyl, in particular C3-C8-Al kinyl, which is optionally substituted by one, two or three R ^a , as defined herein.

According to a further embodiment, Z is C 3 -C 12 -cycloalkyl, such as in particular C ₆ -C 8 -cycloalkyl or C ₆ -C 7 -cycloalkyl, which is in each case optionally substituted by one, two or three R ^a , as defined herein or preferably defined. According to one embodiment of this embodiment of the invention, the cycoalkyl is one, two or three times by Ci-C ₄ -AlkVl, such as. As methyl and / or ethyl substituted.

According to a further embodiment of the invention, Z is C 3 -C 12 -cycloalkenyl, in particular C ₁ -C 10 -cycloalkenyl, especially C ₅ -C ₆ -cycloalkenyl, which is optionally substituted by one, two or three R ^a , as defined herein. According to one embodiment of this embodiment of the invention, the Cycoalkenylgruppe is one, two or three times by Ci-C ₄ -AlkVl, such as. As methyl and / or ethyl substituted.

According to another embodiment of the invention, Z is unsubstituted

Phenyl or phenyl bearing one, two, three or four identical or different groups R ^a , wherein each R ^a is independently selected from fluoro, chloro, cyano, formyl, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C i C ₆ alkylthio, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyl and halophenyl. In a specific embodiment, Z is halogenated phenyl.

In another embodiment, Z is not phenyl. In yet another embodiment, Z is not an aromatic heterocycle bonded via carbon.

According to a further embodiment of the invention, Z is a saturated, partially unsaturated, unsaturated or aromatic heterocycle bonded via carbon to the pyrazolopyrimidine skeleton containing five, six, seven, eight, nine or ten membered heterocycles containing one, two, three or 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 R ^a as defined herein. According to a preferred embodiment of this embodiment, Z stands for optionally substituted five- or six-membered saturated or aromatic heterocycle bonded via carbon to the pyrazolopyrimidine skeleton.

According to a further embodiment of the invention, Z is a methyl group which is substituted by a 5- or 6-membered heterocyclyl radical, the heterocyclyl radical preferably containing one or two, in particular two heteroatoms, selected from N, O and S and in particular O, as ring members and wherein the heterocyclyl radical preferably has a substituent selected from C 1 -C 2 -alkyl, v. a. Methyl, and Ci-C2-haloalkyl, v. a. Trifluoromethyl, carries.

In particular, Z is C 1 -C ₄ -alkyl, in particular methyl, C 5 -C 6 -cycloalkyl, especially cyclohexyl, or a methyl group substituted by a 5-membered heterocyclyl radical, where the heterocyclyl radical is preferably one or two heteroatoms selected from S, N and in particular O, in particular two oxygen atoms, as ring members and wherein the heterocyclyl preferably a substituent selected from Ci-C2-alkyl, especially methyl, and Ci-C2-haloalkyl, especially trifluoromethyl carries, especially CH ₂ - (- C (CH ₃ ) - (O- (CH ₂ ) 2 -O-)) (= 2-methyl-1,3-dioxolan-2-ylmethyl) and CH ₂ - (- C (CF ₃ ) - (O- ( CH ₂ ) ₂ -O-)) (= 2-trifluoromethyl-1,3-dioxolan-2-ylmethyl).

According to one embodiment of the invention, R ^{1 is} not hydrogen.

According to a further embodiment of the invention R ¹ is hydrogen, chlorine, bromine, cyano, nitro, Ci-C ₄ alkoxycarbonyl, CONH _2, COOCH _3, CHO, CH = NO-Ci-C ₄ - alkyl or C (NH ₂₎ = NOH.

According to one embodiment of the invention, R ^{1 is} halogen, cyano, nitro, C 1 -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, C ₁ -C ₈ -hydroxyalkyl, C 1 -C ₈ -alkoxy-C 1 -C ₈ -alkyl, C ₂ - C ₈ - alkenyloxy-C ₈ alkyl, C ₂ -C ₈ alkynyloxy-Ci-C ₈ alkyl, C ₃ -C ₈ cycloalkyloxy-Ci-C ₈ alkyl, Ci-Cs-Ci-alkoxyalkyloxy C ₈ -alkyl, benzyloxy-Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -HaIo- genalkenyl, C ₂ -C ₈ kinyl -alkyl, C ₂ -C ₈ haloalkynyl, C -C ₈ alkoxy, Ci-C ₈ haloalkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, hydroxyimino-Ci-C ₈ alkyl, Ci-C ₈ alkoxy imino-Ci-C ₈ -alkyl or a radical

where p is 1, 2, 3, 4 or 5 and # is the point of attachment to the pyrazolopyridine skeleton; 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 is} C (W ³ ) = NO-C 1 -C ₈ -alkyl, where W ^{3 is} hydrogen or C 1 -C ₈ -alkyl and W ^{3 is} one, two, three or four identical or different groups R ^a may contain. In a specific embodiment, R ^{1 is} CH = NO-C 1 -C ₄ -alkyl. According to another 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 - Ci ₄ -aryl-Ci-Cs-alkyl, where 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 ₈ -alkyl and W ^{4 is} C 1 -C ₈ -alkyl, phenyl or phenylamino where W ³ and / or W ^{4 may} each independently contain one, two, three or four identical or different groups R ^a .

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

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 ⁸ , C (O) SW ⁸ , C (S) SW ⁸ , SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁸ , 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 CrCio-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 aryl--Ci4 C 1 -C ₈ -alkyl;

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

two radicals W ⁷ or one radical W ⁷ and one radical W ⁶ may also together form a saturated or partially unsaturated 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 metal equivalent, an ammonium ion formula (NR ^α R ^ß R ^γ R ^{δ) +,} wherein R ^α, R ^Q, R ^γ and R ^δ are as defined above, -C ₈ alkyl, C ₂ -C ₈ - Alkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl or C ₆ -C ₄ -aryl-C ₁ -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 .

The metal equivalent is a monovalent cation equivalent of the formula (M ^{x +} ) i / _x , where x is 1, 2 or 3 and M is a metal. It goes without saying that M stands for an agriculturally compatible metal. Preferably M is a metal of the first main group (alkali metal), preferably lithium, sodium or potassium, the second main group (alkaline earth metal), preferably magnesium, calcium or barium, or for a transition metal, preferably manganese, copper, zinc or iron.

With the ammonium ion (NR ^α R ^ß R ^γ R ^{δ) +} may be the ammonium ion itself (NH ₄ ⁺⁾ to mono (Ci-Cio) alkyl ammonium, di (Ci-Cio) alkylammonium, tri (Ci-Cio) - alkylammonium, tetra (Ci-Cio) alkylammonium, monoarylammonium, diarylammonium, triarylammonium or mixed aryl-alkylammonium ions, wherein the alkyl substituents of the ammonium ions may optionally be substituted by aryl or hydroxy, preferably R ^α , R ^β , R ^γ and R ^δ independently of one another are H, C 1 -C ₄ -alkyl, phenyl or benzyl. Examples of suitable ammonium ions are diisopropylammonium, tetramethylammonium, tetrabutylammonium and trimethylbenzylammonium.

According to yet another embodiment of the invention, R ^{1 is} saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl which may contain one, two, three or four identical or different groups R ^a .

According to one 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 selected independently from fluorine, chlorine and bromine, C 1 -C ₄ -alkyl, C 2 -C 6 -alkenyl, C 2 -C 5 -alkenyl substituted by carboxy, methoxycarbonyl or ethoxycarbonyl, C 2 -C 6 -alkynyl, preferably C 2 -C 5 -alkynyl, C 2 -C 6 -alkynyl which is substituted by carboxy, methoxycarbonyl or ethoxycarbonyl, preferably C 2 -C 6 -alkynyl C5 alkynyl, Ci-C ₄ hydroxyalkyl, Ci-C ₄ -alkoxy-Ci-C ₄ - alkyl, C3-C6-cycloalkyl, thiocarbamoyl, Ci-C ₄ alkoxycarbonyl, _{Ci-C4-alkylcarbonyl,} Ci-C ₄ -hydroxyiminoalkyl, C 1 -C ₄ -alkoxyimino-C 1 -C ₄ -alkyl, C 1 -C ₄ -alkylthio, C 1 -C ₄ -alkylthio

Alkylsulfinyl, Ci-C ₄ alkylsulfonyl and

According to one aspect of this embodiment, R ¹ represents cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, _{Ci-C4-haloalkyl} having from one to nine halogen atoms independently selected from fluoro, chloro and bromo, Ci-C ₄ alkyl, C3-C6-cycloalkyl, thiocarbamoyl, C1-C4 alkoxycarbonyl, _{Ci-C4-alkylcarbonyl, Ci-C4} or Ci -Hydroximinoalkyl -C ₄ -alkyl koxyimino- Ci-C ₄ alkyl.

In a further 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, methylaminocarbonyl, hydroxymethyl, hydroxyeth-1-yl, methoxymethyl, ethoxymethyl or 1-methoxyethyl. 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-halo-alkyl,} Ci-C ₈ alkoxyalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -Al kinyl, 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 radical # -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 In particular, R ^{a is} 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, Ci-C from each other ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₂ alkoxy Ci- 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 -alkynyl, 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 (= W ¹ ) -NH ₂ , where W ^{1 is} O, NH, N-OH or N-OW ² , where W ^{2 is} C 1 -C ₈ -alkyl or C ₆ -C 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 ₈ -alkyl, W ^{4 is} C 1 -C ₈ -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 ¹ -C ³ (W ³ ) = N (W ⁴ ) in which W ^{3 is} hydrogen or C ¹ -C ⁴ -alkyl, W ^{4 is} C ¹ -C ⁴ -alkyl and each of the alkyl radicals is monosubstituted or disubstituted may be 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 monosubstituted to trisubstituted by identical or different Ci-C ₄ -alkyl, Ci-C ₄ alkoxy, halogen, nitro and / or Ci-C ₄ haloalkyl having 1 to 5 halogen atoms. In yet another embodiment, W ^{3 is} hydrogen, methyl or ethyl and W ⁴ is C 1 -C 2 -alkyl wherein each of the alkyl groups 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 a further embodiment of the invention, R ¹ is -C # (W ⁵⁾ = 0, where W ⁵ Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ kinyl -alkyl, C ₃ -C ₈ -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 ^{5 is} C 1 -C 6 -haloalkyl, C ₂ -C 6 -alkenyl, C ₂ -C 6 -alkynyl, C ₃ -C 6 -cycloalkyl or benzyl, in particular C 1 -C ₄ -haloalkyl, C 1 -C 8 -alkenyl, C ₃ -C 5 -Alkynyl, cyclopropyl, cyclopentyl, cyclohexyl or benzyl, preferably CF3, CCI3, allyl, propargyl, cyclopropyl or benzyl.

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 R ^a -substituted C ₂ -Cδ- alkenyl or C2-C6-AI kinyl, preferably C ₂ -C ₄ -alkenyl, the carbonyl by carboxyl, Mehoxycar-, ethoxycarbonyl, formyl or halogen, or C ₂ -C ₄ 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 another embodiment of the invention, R ^{1 represents} -CONW ⁶ W ⁷ , # -CONW ⁷ -N (W ⁷ ) ₂ , # -CO-NW ⁷ -OW ⁷ , # -C00W ⁸ , # -C (S) OW ⁸ , # -C (O) SW ⁸ , # -C (S) SW ⁸ , # -SW ⁷ , # -SOW ⁷ , # -SO ₂ W ⁷ , # -SO ₃ W ⁸ , # -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 is} Ci-C ₈ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, C ₆ -C ₄ -aryl or C6-Ci4-aryl-Ci-C8-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 also a saturated or partially unsaturated Be able to form a cycle having 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 is hydrogen, a metal equivalent, an ammonium ion (NR ^α R ^β R ^γ R ^δ ) ⁺ , wherein R ^α , R ^β , R ^γ and R ^{δ are} as defined above, C ₁ -C ₈ alkyl, C ₂ -C ₈ - alkenyl, C ₂ -C ₈ -alkyl kinyl, 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 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} saturated, partially unsaturated or aromatic 5- or 6-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 , # -COOW ⁸ , # -C (S) OW ⁸ ,

#C (O) SW ⁸ , # -C (S) SW ⁸ A2): saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl which has one, two, three or four identical or different groups R ^a may contain

A3): # -SW ⁷ , # -SOW ⁷ , # -SO ₂ W ⁷ , # -SO ₃ W ⁸ , # -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 embodiment, R ^{1 is ff} \ <or # -v E LG where B, D, E, G, L are independently of one another: CW ¹² , CW ¹² W ¹³ , N, NW ¹² , O or S with the proviso in that at least one symbol is N, O or S and that O is not adjacent, and wherein V is C, CW ¹² or N and W ¹² and W ^{13 are} independently W ⁷ , halogen, NW ⁷ ₂ , OH, SW ⁷ or OW ⁷ mean.

W ⁶ in the above embodiments preferably Cπo alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C, ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, phenyl-Ci-CIO alkyl where W ^{6 is} unsubstituted or partially or fully halogenated and / or optionally carries one to three radicals from the group R ^a , or W ⁶ is C 1 -C 10 -haloalkyl which may carry one to three radicals from the group R ^a , cyano, nitro, hydroxy, Ci-Cβ alkyl, Ci-C ₆ - haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C ₆ haloalkoxy and wherein: ^Ra is preferably independently selected from , C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkyl, in-butyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ - Alkylsulfonyl, Ci-C ₆ haloalkylsulfonyl, Ci-C6-alkylamino, di-Ci-C6-alkylamino, C2-C ₆ -alkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkynyl and C ₃ -C _6- 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) alkyl ammonium, wherein the alkyl substituents of the ammonium ions, if necessary, by aryl or hydroxy may be substituted, cholinium, C2-Cio-alkenyl, C2-Cio-alkynyl, C ₃ -C 8 cycloalkyl, C ₃ -CS- cycloalkenyl where 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 C 1 -C 10 -haloalkyl which optionally has one to three radicals from the group R ^a or W ⁸ is C 1 -C 10 -alkyl which is partially or fully halogenated and / or carries one to three radicals from the group R ^a , wherein R ^{a is} preferably selected independently from cyano, nitro, hydroxy, C ₁ -C ₆ -alkyl, C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ - haloalkoxy, Ci-C ₆ alkylthio, C -C ₆ haloalkylthio, Ci-C ₆ alkylsulfinyl, CrC ₆ - haloalkylsulfinyl, Ci-C ₆ alkylsulfonyl, Ci-C ₆ haloalkylsulfonyl, Ci-C ₆ -alkylamino, _di-Ci-C6 alkylamino, C2 C ₆ alkenyl, _C2-C6 alkenyloxy, _C2-C6 alkynyl and C ₃ -C ₆ - 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 ⁸ , # -C (O) SW ⁸ , # -SW ⁷ , # - SOW ⁷ , # -SO ₂ W ⁷ , # -SO ₃ W ⁸ , # -SON (W ⁷ ) ₂ , # -P (O ) (OW ⁷ ) ₂ , B (OW ⁷ ) ₂ , pyrrolyl, imidazolyl, 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, 4,2] -

Dioxyzine-3-yl, pyridyl, wherein the heterocyclic radicals are optionally substituted by one or more radicals independently selected from Ci-C4-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 ₈ -cycloalkyl, benzyl, CONW ⁷ OW ⁷ , COOW ⁸ , carboxy-C 1 -C ₄ -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 ⁺ , ½ Ca ²⁺ , ½ Mg ²⁺ , Cu ⁺ , NH ₄ ⁺ , [NH (CH ₃ ) ₃ ] ⁺ , [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 completely or partially by F and / or Cl-substituted Ci-C4-alkyl, carboxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4 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 ⁸ , # -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, wherein the heterocyclic radicals are optionally substituted by one or more radicals independently selected from C 1 -C 4 -alkyl and halogen. It stands

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 completely or partially by F and / or Cl-substituted Ci-C4-alkyl, Ci-C ₄ -alkoxy-Ci-C ₄ -alkyl, AIIyI, 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 specific embodiment of the invention, R ^{1 is} selected from CO-NH-CH ₃ , CON (CH ₃ ) 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-morpholine -1-yl, CONHC (CH ₃ ) ₂ - C≡CH, CONHCH (CH ₃ ) CH ₂ OCH ₃ , COO-NH ₂ [CH (CH ₃ ) ₂ ] ₂ ⁺ , CONHOH, COO-NH ₄ ⁺ , 1 , 3,4-oxathiazol-2-one-5-yl, 5-aminothiadiazol-2-yl, CCNCH ₂ cycloC ₃ H ₅ , CONHC (CH ₃ ) ₂ CN, CONHCH ₂ CH ₂ OH, dioxazin-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 (CHa) 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 OCHS) ₂ , COOCH ₂ -C = CH, CONHCH (CH ₃ ) CH ₂ OCH ₃ , CONHOH, COO propene 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 ) 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 (CH ₂ ) ₂ --C≡CH, COOC (CH ₂ ) ₂ CH ₂ OCH ₃ , COOCH (CH ₃ ) C ( CH ₃ ) ₃ , COOCH (CH ₃ ) CF ₃ , COOCH (CH ₃ ) CH (CH ₃ ) ₂ , COOCH (CH ₃ ) CH ₂ CH ₃ , COOCH (CH ₃ ) CH ₂ OCH ₃ , COOCH (CH ₃ ) - Cyclohexyl, COOCH (C ₂ H ₅ ) -4-methylphenyl, COOCH ₂ C (CH ₃ ) ₃ , COOCH ₂ -C≡CH, COOCH ₂ CH ₂ Br, COOCH ₂ CH ₂ CH ₂ CH ₃ , COOCH ₂ CH ₂ CH ₃ , COOCH ₂ CH ₂ OCH ₃ ,

COOCH ₂ CH = CHCH ₃ , COOCH ₂ Cl, COOCH ₂ F, COOCH (CH ₃ ) CH = CH ₂ , COO-CyClO-C ₆ H ₅ , CON (CH ₃ ) COCH (NH ₂ ) CH ₃ , 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 OCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₃ , 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 (CHa) 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 (CH ₃ ) = CH ₂ , CH = CHBr, C (NH ₂ ) = NOH, CH = N (4-chlorophenyl), CH = N (CH ₂ COOCH ₃ ), 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 (CH ₃ ) = NOH, C (CH ₃ ) = NOCH ₃ , CH ₂ OH, CH (CH ₃ ) OH, C (cyclo-C ₃ H ₅ ) OH, CH (OCH ₃ ) CH (CH ₃ ) ₂ , CH (OH) CH ₂ Cl,

C (CH ₃ ) (OH) CH (CH ₃ ) ₂ , CH (OH) CH (CH ₃ ) ₂ , CH (OH) C≡CCH ₃ , CH (OH) C≡CH, CH (CF ₃ ) OH,

CH (OH) C (CHs) = CH _2, CH (CH ₃₎ OCH (CHs) _2, C (CFs) ₂ OCH ₃ and

# ^ ° ^ C ₂ H ₅

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 OCH ₃ , COOCH ₂ COOCHS, COOC ₂ H ₅ , CONHCH ₂ COOCH ₃ , 2 Pyridyl, 3-CHs-1, 2,4-triazol-5-yl, CONCH ₃ OCHs, 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 (CHa ) ₂ , COO-iC ₃ H ₇ , CONHCH (CH ₃ ) CH ₂ OH, COOCH (CH ₂ OCHS) ₂ , COOCH ₂ -C≡CH, CONHCH (CH ₃ ) CH ₂ OCHS, CONHOH, COO-propene-3 -yl, NO ₂ , CONH-2-pyrimidinyl, CONHCH ₂ COOC ₂ H ₅ , CH ₂ COOC ₂ H ₅ , COO-NH (CH ₂ CH ₃ ) S ⁺ , 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 (C H ₃ ) ₂ -C≡CH, COOC (CHS) ₂ CH ₂ OCH ₃ , COOCH (CHS) CH ₂ CH ₃ ,

COOCH (CHS) CH ₂ OCH ₃ , COOCH (CH ₃ ) cyclohexyl, COOCH ₂ C (CH ₃ ) ₃ , COOCH ₂ CH ₂ Br, COOCH ₂ CH ₂ CH ₃ , COOCH ₂ CH ₂ OCHS, COOCH (CH ₃ ) CH = CH ₂ , COO-cyclo-C ₆ H ₅ , CONH (CH ₂ ) ₂ OCH ₃ , CONH ₂ , oxazol-2-yl, COOCH (CH ₃ ) COOC ₂ H ₅ , CONCHSOCH ₃ , 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 (CHA) 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 (CHa) = NOH, C (CHa) = NOCH ₃ , CH ₂ OH, CH (CH ₃ ) OH, CH (OH) CH (CH ₃ ) ₂ , CH (OH) C≡CCH ₃ , CH (OH) C≡CH, CH (OH ) C (CH ₃ ) = CH ₂ , and

, According to another specific embodiment of this embodiment, R ^{1 is} selected from CO-NH-CH ₃ , CON (CHa) ₂ , CONH (iC ₃ H ₇ ), COOH, COO-benzyl, COOCH ₂ CH ₂ OCH ₃₁ 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 (CHa) ₂ , SCH ₃ , SO ₂ NHCH ₃ , CH = CH ₂ , CH = CHCOOH, CH = CHCOOC ₂ H ₅ , C≡CH, C (CH ₃ ) = 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

The other substituents according to formula I preferably have the preferred meanings described herein, in particular compounds of the formulas Ia.1, Ia.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9 and Ia.10 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 314, and R ¹ has one of the meanings the just described embodiments.

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

Specifically, R ^{1 is} hydrogen, CN, CONH ₂ , COOCH ₃ or CHO.

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 a further embodiment of the compounds I, R ^{2 is} hydrogen. In a further embodiment of the compounds I, R ^{2 is} cyano. In a further embodiment of the compounds I, R ^{2 is} formyl. In a further embodiment of the compounds I, R ^{2 is} CR ^c R ^d OR ^e . In a further embodiment of the compounds I, R ^{2 is} C (R ^f ) = NRs.

In a further preferred embodiment, R ¹ and R ^{2 are} each independently of one another hydrogen, cyano, halogen or C 1 -C ₄ -alkyl, and in particular both are hydrogen. According to a further preferred embodiment R ^{1 is} CN and R ^{2 is} hydrogen.

The following compounds Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, Ia.15, Ia.16 and Ia.17 are each embodiments of the compounds of formula I.

In particular, with regard to their use, the compounds I according to the invention which are compiled in the following Tables 1 to 316 are preferred. The groups mentioned in the tables for a substituent also represent, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.

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

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

la.13 Ia.14

Ia.15 la.17 Table 1

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 2

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-nitropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one line of the table A corresponds

Table 3

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the table A corresponds

Table 4

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the table A corresponds

Table 5

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 4-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the table A corresponds

Table 6

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 3-methylpyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the table A corresponds

Table 7

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-ethylpyridin-2-yl and the combination of Z and R ¹ for each compound corresponds to one line of the table A corresponds

Table 8

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the table A corresponds

Table 9

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds to Table 10

Compounds of the formulas Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia1.1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-trifluoromethylpyridin-2-yl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to Table 1 1

Compounds of the formulas Ia.1, La.2, Ia.3, Ia.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia1.1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to Table 12

Compounds of the formula Ia.1, La.2, Ia.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 13

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-difluoropyridin-2-yl and the combination of Z and R ^{1 is} a compound of each one of the

Table A corresponds to Table 14

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dichloropyridin-2-yl and the combination of Z and R ^{1 is} a compound of one row each of

Table A corresponds to Table 15

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pyridin-3-yl and the

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

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pyridin-4-yl and the

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

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 18

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pyridazin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 19

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 6-chloropyridazin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the table A corresponds

Table 20

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 1, 3,5-triazin-2-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 21

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pyrimidin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 22

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 23

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pyrimidin-5-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 24

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-6-trifluoromethyl-pyrimidin-4-yl and the combination of Z and R ¹ for a compound each corresponds to one row of Table A.

Table 25

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dimethyl-6-trifluoromethylpyrimidin-4-yl and the combination of Z and R ^{1 is} a Connection corresponds in each case one row of Table A.

Table 26

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 6-trifluoromethylpyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A corresponds to Table 27

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 5-methyl-6-trifluoromethyl-pyrimidin-4-yl and the combination of Z and R ¹ for each compound One row of Table A corresponds to Table 28

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 5-chloro-6-methylpyrimidine-4-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds to Table 29

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 5-bromo-6-methyl-pyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds to Table 30

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, la.14, la.15, la.16 and la.17 in which Y is 5-fluoro-6-methyl-pyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds to Table 31

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, Ia.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 5-chloropyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A. corresponds to Table 32

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, Ia.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. corresponds to Table 33

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, la.6, la.7, la.8, la.9, la10, la.11, la.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-bromopyrimidin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A. Table 34

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-methyl-fluoropyrimidine-5-4-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds Table 35

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-5-chloropyrimidin-4-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 36

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-5-bromopyrimidin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 37

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-dimethyl-5-chloropyrimidin-4-yl and the combination of Z and R ¹ for a compound, respectively corresponds to one line of Table A.

Table 38

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-dimethyl-5-bromopyrimidin-4-yl and the combination of Z and R ^{1 is} a compound in each case corresponds to one line of Table A.

Table 39

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-fluoro-6-fluoromethyl-pyrimidin-4-yl and the combination of Z and R ¹ for a compound each corresponds to one row of Table A.

Table 40

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5,6-dimethylpyrimidin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 41

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds

Table 42

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5,6-trimethylpyrimidin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 43

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-dimethylpyrimidin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A corresponds to Table 44

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5,6-trimethylpyrimidin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 45

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-di (trifluoromethyl) pyrimidine

2-yl and the combination of Z and R ¹ for each compound

Row of Table A corresponds to Table 46

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-dimethyl-5-chloropyrimidine

2-yl and the combination of Z and R ¹ for each compound

Row of Table A corresponds to 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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-dimethyl-5-bromopyrimidine

2-yl and the combination of Z and R ¹ for each compound

Row of Table A corresponds to Table 48

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methylpyrimidin-5-yl and the combination of Z and R ^{1 is} a compound of each one of the

Table A corresponds to Table 49

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-dimethylpyrimidin-5-yl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds to Table 50

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-trifluoromethyl-6-methyl-pyrimidin-5-yl and the combination of Z and R ¹ for each compound One row of Table A corresponds to Table 51

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4,6-trimethylpyrimidin-5-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds Table 52

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the table A corresponds

Table 53

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 3-bromopyridin-2-yl and the combination of Z and R ¹ for a compound in each case corresponds to one line of the table A corresponds

Table 54

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-nitropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 55

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-chloropyridin-2-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table A. corresponds to

Table 56

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the table A corresponds

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-ethylpyridin-2-yl and the combination of Z and R ^{1 is} a compound of one line of each Belle A corresponds

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, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-nitropyridin-2-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the Belle A corresponds

Table 59

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-chloropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 60

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds to Table 61

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-methylpyridin-2-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds to Table 62

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-ethylpyridin-2-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds to Table 63

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-cyanopyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 64

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-fluoropyridin-2-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds to Table 65

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-bromopyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 66

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y represents 3-chloro-5-methylpyridin-2-yl and the combination of Z and R ^{1 represents} a compound of one row each of Table A corresponds to Table 67

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-ethylpyridin-2-yl and the combination of Z and R ¹ for a compound in each case one Row of Table A corresponds to Table 68

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-cyanopyridin-2-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds Table 69

Compounds of the formula Ia.1, La.2, Ia.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-nitropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 70

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-fluoropyridin-2-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 71

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-chloropyridin-2-yl and the combination of Z and R ^{1 is} a compound of each one of the Table A corresponds

Table 72

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-bromopyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 73

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dimethylpyridin-2-yl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 74

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-ethylpyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 75

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-cyanopyridin-2-yl and the combination of Z and R ^{1 is} a compound of each one of the Table A corresponds

Table 76

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-nitropyridin-2-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 77

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-bromo-5-fluoropyridin-2-yl indicates and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 78

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-bromo-5-chloropyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 79

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-bromo-5-methylpyridin-2-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds

Table 80

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-nitro-5-fluoropyridin-2-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds

Table 81

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-nitro-5-chloropyridin-2-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 82

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-nitro-5-methylpyridin-2-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 83

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dibromopyridin-2-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 84

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, La.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 85

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloropyridin-4-yl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to Table 86

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-bromopyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line of each Belle A corresponds

Table 87

Compounds of the formula Ia.1, La.2, Ia.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methylpyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line of each Belle A corresponds

Table 88

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-nitropyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line of each Belle A corresponds

Table 89

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-difluoropyridin-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 90

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-chloropyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 91

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 Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 3-fluoro-5-bromopyridin-4-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of Table A corresponds

Table 92

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-methylpyridin-4-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds

Table 93

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-ethylpyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 94

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds to Table 95

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-5-nitropyridin-4-yl and the combination of Z and R ¹ for a compound in each case one Row of Table A corresponds to Table 96

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y represents 3,5-dichloro-5-chloropyridin-4-yl and the combination of Z and R ¹ for a compound one row of Table A corresponds to Table 97

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-bromopyridin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 98

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-methylpyridin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 99

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-ethylpyridin-4-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds to Table 100

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-cyanopyridin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 101

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-5-nitropyridin-4-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds to Table 102

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dimethylpyridin-4-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds Table 103

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-bromopyridin-4-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 104

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-cyanopyridin-4-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 105

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-nitropyridin-4-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 106

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoropyridin-3-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 107

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y signifies 2-chloropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the table A corresponds

Table 108

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-bromopyridin-3-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 109

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one line of the table A corresponds

Table 1 10

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-nitropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one line of the table A corresponds

Table 1 11

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 1 12

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 1 13

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 1 14

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 Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 1 15

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-nitropyridin-3-yl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 1 16

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4-difluoropyridin-3-yl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds

Table 1 17

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-chloropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 1 18

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-bromopyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds

Table 1 19

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-methylpyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds Table 120

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-methylsulfanylpyridin-3-yl and the combination of Z and R ^{1 is} a compound in each case corresponds to one line of Table A.

Table 121

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-fluoro-4-methyl sulfinylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A.

Table 122

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-fluoro-4-methyl-sulfonylpyridine-3-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A.

Table 123

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-nitropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds

Table 124

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds

Table 125

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-fluoropyridin-3-yl and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table 126

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-bromopyridin-3-yl and the combination of Z and R ¹ for each compound Line of Table A corresponds

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.11, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-methylpyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds

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.11, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-methyl- sulfanylpyτidin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A corresponds to Table 129

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-chloro-4-methyl- sulfinylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds One row of table A corresponds to table 130

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-chloro-4-methyl-sulfonylpyridine-3-yl and the combination of Z and R ¹ for each compound corresponds One row of Table A corresponds to Table 131

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-nitropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds to Table 132

Compounds of the formula Ia.1, la.2, la.3, la.4, la5, la6, la.7, la.8, la9, la10, la.1.1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of Table A corresponds to Table 133

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-4-chloropyridin-3-yl and the combination of Z and R ¹ for each compound Row of Table A corresponds to Table 134

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-4-fluoropyridin-3-yl and the combination of Z and R ¹ for each compound Row of Table A corresponds to Table 135

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 2-methyl-4-bromopyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line each Table A corresponds to Table 136

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-methyl-4-methyl- sulfanylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A. Table 137

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-methyl-4-methyl- sulfinylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A.

Table 138

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-4-methylsulfonylpyridin-3-yl and the combination of Z and R ^{1 is} a compound each - because one line corresponds to Table A.

Table 139

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-4-nitropyridin-3-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds

Table 140

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, la.6, la.7, Ia.8, Ia.9, Ia.10, la.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-bromo-4-fluoropyridin-3-yl and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table 141

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 2-bromo-4-chloropyridin-3-yl and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table 142

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-bromo-4-methylpyridin-3-yl and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table 143

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-nitro-fluoropyridin-4-3-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds

Table 144

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 2-nitro-4-chloropyridine-3-yl and the combination of Z and R ¹ for each compound corresponds to a line Table A corresponds

Table 145

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-nitro-4-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 146

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-difluoropyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 147

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-chloropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 148

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-bromopyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 149

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, La.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 150

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-ethylpyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 151

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-cyanopyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 152

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-methylcarbamoylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table A.

Table 153

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.11, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 4-fluoro-6-dimethyl-carbamoylpyridin-3-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A. Table 154

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-fluoro-6-nitropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 155

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 the table A corresponds

Table 156

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-fluoropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 157

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, La.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-bromopyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 158

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 159

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-ethylpyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 160

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-methoxypyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 161

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-cyanopyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 162

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-chloro-6-nitropyridin-3-yl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A corresponds to Table 163

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methyl-6-fluoropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds to Table 164

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methyl-6-chloropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds to Table 165

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methyl-6-bromopyridin-3-yl and the combination of Z and R ¹ for each compound of one line Table A corresponds to Table 166

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,6-dimethylpyridin-3-yl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds to Table 167

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, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methyl-6-cyanopyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Row of Table A corresponds to Table 168

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-methyl-6-nitropyridin-3-yl and the combination of Z and R ¹ for a compound in each case one Row of Table A corresponds to Table 169

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-bromo-6-fluoropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds to Table 170

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-bromo-6-chloropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds Table 171

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-bromo-6-methylpyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 172

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-nitro-6-fluoropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 173

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-nitro-6-chloropyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 174

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4-nitro-6-methylpyridin-3-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 175

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4-dichloro-6-methylpyridin-3-yl and the combination of Z and R ¹ for a compound corresponds to one row of Table A.

Table 176

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dimethylpyrazol-1-yl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds

Table 177

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 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-ethyl-5-methylpyrazol-1-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 178

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,4,5-trimethylpyrazol-1-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 179

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dimethyl-4-chloropyrazole-1 yl and the combination of Z and R ¹ for one compound each one

Row of Table A corresponds to Table 180

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 181

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,4-dichloro-5-trichloromethylpyrazol-1-yl and the combination of Z and R ^{1 is} a Connection of one row of Table A corresponds to Table 182

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 183

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dichloro-4-methylpyrazol-1-yl and the combination of Z and R ¹ for a compound one each

Row of Table A corresponds to Table 184

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-4-chloropyrazol-1-yl and the combination of Z and R ¹ for a compound in each case one Row of Table A corresponds to Table 185

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 1, 3-dimethylpyrazol-5-yl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds to Table 186

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 1-methyl-3-trifluoro-methylpyrazol-5-yl and the combination of Z and R ¹ for each compound corresponds One row of Table A corresponds to Table 187

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 1,5-dimethylpyrazol-3-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds Table 188

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 1, 3,5-trimethylpyrazol-4-yl and the combination of Z and R ^{1 is} a compound of one line Table A corresponds

Table 189

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y is 1-methyl-3-trifluoro-methylpyrazole-4-yl and the combination of Z and R ¹ for each compound corresponds corresponds to one line of Table A.

Table 190

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 1, 3-dimethylpyrazol-4-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 191

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, La.12 , la.13, la.14, la.15, la.16 and la.17, in which Y is 1-methyl-5-trifluoromethylpyrazol-4-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table A.

Table 192

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.1, Ia. 12, la.13, la.14, la.15, la.16 and la.17, in which Y is 1, 5-dimethylpyrazol-4-yl and the combination of Z and R ^{1 is} a compound of each one of the Table A corresponds

Table 193

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, La.12 , la.13, la.14, la.15, la.16 and la.17, in which Y is 1-methyl-3,5-dichloropyrrol-2-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table A.

Table 194

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, La.12 , la.13, la.14, la.15, la.16 and la.17, in which Y is 2-methylthiazol-4-yl and the combination of Z and R ¹ for each compound corresponds to one line of the table A corresponds

Table 195

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, La.12 , la.13, la.14, la.15, la.16 and la.17, 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 A.

Table 196

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, La.12 , la.13, la.14, la.15, la.16 and la.17, 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 A.

Table 197

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dichlorothiazol-4-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 198

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-5-bromo-thiazol-4-yl and the combination of Z and R ¹ for each compound corresponds to one line of Table A.

Table 199

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 200

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y represents 3-methyl-5-chloroisothiazol-4-yl and the combination of Z and R ^{1 represents} a compound of one line each Table A corresponds

Table 201

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 202

Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, Ia.6, Ia.7, Ia.8, La.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds

Table 203

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloroisoxazol-4-yl and the combination of Z and R ^{1 is} a compound of one row of Table A, respectively corresponds to

Table 204

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, la.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 205

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 206

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 the table A corresponds

Table 207

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyloxazol-4-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 208

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-dichloroimidazol-1-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 209

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-dimethylimidazol-1-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 210

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 3,5-dimethyl-1,2,4-triazol-1-yl and the combination of Z and R ¹ for a connection corresponds in each case to one row of Table A.

Table 211

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dichloro-1,2,4-triazol-1-yl and the combination of Z and R ¹ for a connection corresponds in each case to one row of Table A.

Table 212

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 to one row of Table A.

Table 213

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds to Table 214

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-ditrifluoromethyl-1,2,4-triazol-1-yl and the combination of Z and R ¹ for a connection in each case one row of Table A corresponds to Table 215

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y represents 3-methyl-1,2,4-triazol-1-yl and the combination of Z and R ^{1 represents} a Connection of one row of Table A corresponds to Table 216

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-chloro-1, 2,4-triazol-1-yl and the combination of Z and R ^{1 is} a Connection of one row of Table A corresponds to Table 217

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-fluoro-1, 2,4-triazol-1-yl and the combination of Z and R ^{1 is} a Connection of one row of Table A corresponds to Table 218

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-bromo-1, 2,4-triazol-1-yl and the combination of Z and R ¹ for a Connection of one row of Table A corresponds to Table 219

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-trifluoromethyl-1,2,4-triazole

1-yl and the combination of Z and R ¹ for each compound

Row of Table A corresponds to Table 220

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, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-dimethyl-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a connection of one row of Table A corresponds to Table 221

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-dichloro-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a compound corresponds to one row of Table A. Table 222

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-dibromo-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a connection corresponds in each case to one row of Table A.

Table 223

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-difluoro-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a connection corresponds in each case to one row of Table A.

Table 224

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a connection corresponds in each case to one row of Table A.

Table 225

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-methyl-1,2,3-triazol-1-yl and the combination of Z and R ¹ for a Compound corresponds to one line of Table A.

Table 226

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-chloro-1,2,3-triazol-1-yl and the combination of Z and R ^{1 is} a Compound corresponds to one line of Table A.

Table 227

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 5-fluoro-1,2,3-triazol-1-yl and the combination of Z and R ^{1 is} a Compound corresponds to one line of Table A.

Table 228

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, la.6, la.7, la.8, la.9, la10, la.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17 in which Y is 5-bromo-1,2,3-triazol-1-yl and the combination of Z and R ^{1 is} for one compound corresponds in each case to one row of Table A.

Table 229

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, la.6, la.7, la.8, la.9, la10, la.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 5-trifluoromethyl-1,2,3-triazol-1-yl and the combination of Z and R ^{1 is} for one compound corresponds in each case to one row of Table A.

Table 230

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.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 231

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,5-dichlorothiphen-2-yl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 232

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,4,5-trichlorothiophen-2-yl and the combination of Z and R ¹ for a compound of one line Table A corresponds

Table 233

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 234

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 235

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 236

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dichlorothiophen-3-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 237

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dibromothiophen-3-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 238

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 239

Compounds of the formula Ia.1, La.2, Ia.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methyl-5-isopropylpyrazol-1-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 240

Compounds of the formula Ia.1, La.2, Ia.3, La.4, La.5, La.6, La.7, La.8, La.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y 1 signifies methyl-5-methoxypyrazol-3-yl and the combination of Z and R ¹ for a compound in each case one Line of Table A corresponds

Table 241

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 242

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3-methylthien-2-yl and the combination of Z and R ^{1 is} a compound of one line of each Belle A corresponds

Table 243

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dimethylthien-3-yl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 244

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 245

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one line of Table A.

Table 246

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 247

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-6-methylphenyl indicates and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 248

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 249

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-difluoro-4-methoxyphenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 250

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is pentafluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 251

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-4-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 252

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 253

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methoxy-6-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 254

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 255

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 256

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 257

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 258

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 259

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,3-difluorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one line of Table A.

Table 260

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 261

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y 2, 3,4-trifluorophenyl and the combination of Z and R ¹ for a compound in each case one line of the table A corresponds

Table 262

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 263

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 264

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A corresponds to Table 265

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-fluoro-4-methylphenyl and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds to Table 266

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13 ,, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A Table 267

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, La.11, Ia.12 , Ia.13 ,, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4,6-trimethylphenyl and the combination of Z and R ^{1 represents} a compound of one row each of

Table A corresponds to Table 268

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-difluoro-4-methylphenyl and the combination of Z and R ^{1 is} a compound of one row of each Table A corresponds to Table 269

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 270

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 271

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 272

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, Ia.7, La.8, La.9, Ia.10, Ia.11, Ia.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 273

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-5-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 274

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-methyl-5-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 275

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-methoxyphenyl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 276

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 line of the Belle A corresponds

Table 277

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-dichloro-4-fluorophenyl and the combination of Z and R ¹ for a compound in each case one row of Table A corresponds

Table 278

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 279

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,3,6-trifluorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 280

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4,5-trifluorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 281

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,3,4,6-tetrafluorophenyl. indicates and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 282

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 283

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-4-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 284

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4-dichloro-5-methylphenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 285

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,5-dichlorophenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 286

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 287

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-5-bromophenyl and the combination of Z and R ¹ for a compound in each case one row of Table A. corresponds to

Table 288

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, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 289

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-5-methylphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A. Table 290

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 3,4-methylenedioxyphenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 291

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,4-difluoro-6-chlorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 292

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-difluoro-4-chlorophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 293

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is phenyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 294

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2-chloro-5-nitrophenyl and the combination of Z and R ¹ for a compound in each case one row of the table A corresponds

Table 295

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 4- (4-methylpiperidin-1-yl) -phenyl and the combination of Z and R ¹ for each compound corresponds to a row of Table A.

Table 296

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is 2,6-difluoro-4- (4-methylpiperidin-1-yl) -phenyl and the combination of Z and R ¹ for a compound fertil corresponds in each case to one row of Table A.

Table 297

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, La.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH ₃ and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A corresponds to Table 298

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, Ia.6, La.7, La.8, La.9, Ia.10, Ia.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. Table 299

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, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH (CH ₃ ) 2 and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 300

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH (CH ₃ ) (C ₂ H ₅ ) and the combination of Z and R ^{1 is} for one compound each Table A corresponds

Table 301

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 302

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH (CH ₃ ) (nC ₃ H ₇ ) and the combination of Z and R ^{1 is} for one compound each Table A corresponds

Table 303

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 304

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH ₂ (CH ₂ ) ₆ CH ₃ and the combination of Z and R ^{1 is} a compound of one row of the table A corresponds

Table 305

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y denotes cyclo-CsHg and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 306

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, La.12 , Ia.13, la.14, la.15, la.16 and la.17 in which Y cyclo-CβHn means and the combination of Z and R ¹ for each compound corresponds to one row of Table a

Table 307

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CyClio-CzHi ₃ , and the Combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 308

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH ₂ CH = C (CHa) ₂ and the combination of Z and R ¹ for each compound corresponds to one row of the table A corresponds

Table 309

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 310

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 311

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH ₂ C≡C (CH ₂ ) ₃ CH ₃ and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table 312

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A.

Table 313

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, La.12 , Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y 1 denotes methylcyclohexyl and the combination of Z and R ¹ for a compound corresponds in each case to one row of Table A.

Table 314

Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, Ia.9, Ia.10, La.1 1, la. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, 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 A. corresponds to

Table 315

Compounds of the formula Ia.1, la.2, la.3, la.4, Ia.5, la.6, la.7, la.8, la.9, la10, la.1 1, la. 12, Ia.13, la.14, la.15, la.16 and la.17, 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 A. Table 316

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.1 1, Ia. 12, Ia.13, Ia.14, Ia.15, Ia.16 and Ia.17, in which Y is CH (CH ₃ ) (C ₂ H ₅ ) and the combination of Z and R ¹ for each compound Line of Table A corresponds

Table A

CH ₂ - (C (CH ₃ ) (- O- (CH ₂ ) ₂ -O-)) = # - CH,

O O

CF, CH ₂ - (C (CF ₃ ) (- O- (CH ₂ ) ₂ -O-)) =

O O

The compounds I according to the invention and / or their agriculturally acceptable salts are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). 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, oats, rice, corn, grass, bananas, cotton, soy, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers. Beans, tomatoes, potatoes and pumpkins, as well as the seeds of these plants. The compounds I are suitable for controlling Alternaria species on vegetables, oilseed rape, sugar beets and fruits and rice such. BA solani or A. alternata on potatoes and tomatoes.

The compounds I are suitable for controlling Aphanomyces species on sugar beets and vegetables.

The compounds I are suitable for controlling Ascochyta species on cereals and vegetables.

The compounds I are suitable for controlling Bipolaris and Drechslera species on corn, cereals, rice and turf, such as. B. D. maydis on corn.

The compounds I are suitable for controlling Blumeria graminis (powdery mildew) on cereals.

The compounds I are suitable for controlling Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and grapevines.

The compounds I are suitable for controlling Bremia lactucae on lettuce.

The compounds I are suitable for controlling Cercospora species on corn, soybeans, rice and sugar beet.

The compounds I are suitable for controlling Cochliobolus species on corn, cereals, rice, such as. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.

The compounds I are suitable for controlling Colletotricum species on soybeans and cotton.

The compounds I are suitable for controlling Drechslera species, Pyrenophora species on corn, cereals, rice and turf, such as. B. teres on barley or D. tritici- repentis on wheat.

The compounds I are suitable for controlling Esca on grapevine, caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus).

The compounds I are suitable for controlling Elsinoe ampelina on the grapevine.

The compounds I are suitable for controlling Exserohilum species on maize. The compounds I are suitable for controlling Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits.

The compounds I are suitable for controlling Fusarium and Verticillium species on various plants such. B. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, such as. As tomatoes.

The compounds I are suitable for controlling Gaeumanomyces graminis on cereals.

The compounds I are suitable for controlling Gibberella species on cereals and rice (for example Gibberella fujikuroi on rice).

The compounds I are suitable for controlling Glomerella cingulata on grapevines and other plants.

The compounds I are suitable for controlling grainstaining complex in rice.

The compounds I are suitable for controlling Guignardia budwelli on the grapevine.

The compounds I are suitable for controlling Helminthosporium species on corn and rice.

The compounds I are suitable for controlling Isariopsis clavispora on the grapevine.

The compounds I are suitable for combating Michrodochium nivale on cereals.

The compounds I are suitable for controlling Mycosphaerella species on cereals, bananas and peanuts, such as. M. graminicola on wheat or M. fijiensis on bananas.

The compounds I are suitable for controlling Peronospora species on cabbage and bulbous plants, such as. B. P. brassicae on cabbage or P. destructor on onion.

The compounds I are suitable for controlling Phakopsara pachyrhizi and Phokopsara meibomiae on soybeans.

The compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers, P. viticola on the grapevine. The compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.

The compounds I are suitable for controlling Phytophthora species on various plants such. B. P. capsici to paprika.

The compounds I are suitable for controlling Plasmopara viticola on grapevines.

The compounds I are suitable for controlling Podosphaera leucotricha on apple.

The compounds I are suitable for controlling Pseudocercosporella herpotriodides on cereals.

The compounds I are suitable for controlling Pseudoperonospora on various plants such. P. cubensis on cucumber or P. humili on hops.

The compounds I are suitable for controlling pseudopezicula tracheiphilai on the grapevine.

The compounds I are suitable for controlling Puccinia species on various plants such. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus.

The compounds I are suitable for controlling Pyricularia oryzae, Corticium sakiisi, Sarocladium oryzae, S. attenuatum, Entyloma oryzae, on rice.

The compounds I are suitable for controlling Pyricularia grisea on lawns and cereals.

The compounds I are suitable for controlling Pythium spp. on lawn, rice, corn, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants, such as. P.ultiumum on various plants, P. aphanidermatum on lawn.

The compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various plants such. B. R. solani on turnips and various plants.

The compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale. The compounds I are suitable for controlling Sclerotinia species on rape and sunflowers.

The compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.

The compounds I are suitable for controlling Erysiphe (syn. Uncinula) necator on grapevine.

The compounds I are suitable for controlling Setospaeria species on maize and turf.

The compounds I are suitable for controlling Sphacelotheca reilinia on maize.

The compounds I are suitable for controlling Thievaliopsis species on soybeans and cotton.

The compounds I are suitable for controlling Tilletia species on cereals.

The compounds I are suitable for controlling Ustilago species on cereals, maize and sugar cane, such as. B. U. maydis on corn.

The compounds I are suitable for controlling Venturia species (scab) on apples and pears such as. z. B. V. inaequalis to apple. In particular, they are suitable for controlling harmful fungi from the class of Peronosporomycetes (syn.Oomyceten), such as Peronospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Pythium species.

The compounds I are also suitable for controlling harmful fungi in the protection of materials (eg 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, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.

The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients. The application can be done both before and after the infection of the materials, plants or seeds by the fungi. The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.

The application rates in the application in crop protection, depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.

In the seed treatment, 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 can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.

The compounds I can be converted into the customary formulations, for. As 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. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially: water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol) , Ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used, - excipients such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.

Suitable surface-active substances are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfonated condensation products of naphthalene and naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether aryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite liquors and methyl cellulose into consideration.

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. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, eg. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers are z. As mineral earths, 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. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

The formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient. The 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 adjuvants are 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 ingredients are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. 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 by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and brought to 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 compounds are comminuted to a fine suspension of active substance in an agitated ball mill with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent. 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 compounds are finely ground with the addition of 50 parts by weight dispersing 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 compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. 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 by weight of swelling agent and 70 parts by weight of water or an organic solvent become a fine suspension Dilution with water results in a stable suspension with 20% by weight 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 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 z. B. 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 active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied. 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 (spray powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, 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, possibly also just immediately 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 an adjuvant in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S ^240® ; Alcohol alkoxylates, eg. As Atplus 245 ^®, Atplus MBA 13.03 ^®, 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 of the invention may also be present in the application form as fungicides together with other active ingredients, the z. As with herbicides, insecticides, growth regulators, fungicides or with fertilizers. When mixing the compounds I or the agents containing them with one or more further active compounds, in particular fungicides, for example, in many cases, the activity spectrum can be broadened or development of resistance can be prevented. In many cases, synergistic effects are obtained.

The present invention further provides a combination of at least one pyrazolopyrimidine of the formula I, in particular a pyrazolopyrimidine which is disclosed as preferred in the present specification, and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating agent.

A further subject matter of the present invention is a pesticidal composition comprising at least one pyrazolopyrimidine I, in particular a pyrazolopyrimidine of the formula I described as preferred in the present description and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier. Such a pesticidal agent may contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient. The following list L of fungicides, with which the compounds according to the invention can be used together, is intended to explain but not limit the possible combinations:

List L: strobilurins

Azoxystrobin, dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate; L-2

Carboxylic Acid Amides - Carboxylic Anilides: Benalaxyl, Benodanil, Boscalid, Carboxin, Mepronil, Fenfuram, Fenhexamide, Flutolanil, Furametpyr, Metalaxyl, Ofurace, Oxadixyl, Oxycarboxine, Penthiopyrad, Thifluzamide, Tiadinil, 4-Difluoromethyl-2-methyl-thiazole-5-carbon 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'-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3,4-dichloro-isothiazole-5-carboxylic acid (2-cyano-phenyl) -amide;

- Carboxylic acid morpholides: Dimethomorph, Flumorph;

Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide; Other carboxamides: carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino 3-methyl-butyramide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-ethanesulfonyl-amino-3-methyl- butyramide;

azoles

- triazoles: bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazo - Ie, triadimenol, triadimefon, triticonazole;

- imidazoles: cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;

Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- Other: Ethaboxam, Etridiazole, Hymexazole;

Nitrogen-containing heterocyclyl compounds

Pyridines: fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine; Pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;

- piperazines: triforins;

- Pyrroles: fludioxonil, fenpiclonil; - Morpholines: aldimorph, dodemorph, fenpropimorph, tridemorph;

Dicarboximides: iprodione, procymidone, vinclozolin;

- others: acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;

Carbamates and Dithiocarbamates - Dithiocarbamates: Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, Ziram;

Carbamates: diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb, 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid methyl ester, N- (1- (1- (4- Cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester;

Other fungicides

- guanidines: dodine, iminoctadine, guazatine;

- Antibiotics: Kasugamycin, Polyoxins, Streptomycin, Validamycin A; Organometallic compounds: fentin salts;

Sulfur-containing heterocyclyl compounds: isoprothiolanes, dithianone;

Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;

Organochlorine compounds: thiophanates methyl, chlorothalonil, dichlofluanid, toiylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;

Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;

- Inorganic active substances: Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur;

- Other: Spiroxamine, Cyflufenamid, Cymoxanil, Metrafenone.

Accordingly, the present invention further relates to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as preferred, and the in each case indicated in the relevant line further active ingredient (component 2). According to one embodiment of the invention, component 1 in each row of table B is in each case one of the compounds of the formula I specified concretely in tables 1 to 316. Table B

The active ingredients mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf .: http://www.hclrss.demon.co.uk/index.html); they are commercially available. The compounds named after IUPAC, their preparation and their fungicidal action are also known [cf. EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122;

EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO 04/049804].

The present invention furthermore relates to the pharmaceutical use of the pyrazolopyrimidines of the formula I according to the invention, in particular the pyrazolopyrimidines of the formula I described in the preceding description, and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals, such as for example, in humans. The invention also relates to a pharmaceutical composition which comprises at least one compound I according to the invention, in particular at least one compound I described as preferred, and / or a pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.

The compounds of the formula I according to the invention, in particular the compounds of the formula I according to the invention described in the preceding description, and / or their pharmaceutically acceptable salts, effectively inhibit the growth and / or proliferation of tumor cells, as in standard tests on tumor cell lines, as HeLa, MCF-7 and COLO 205 can be shown. In particular, compounds of the invention of the formula I show IC50 values generally <10 ^"6 mol / l (ie <1 uM), preferably IC ₅ o values ^{<10" 7} mol / l (ie <100 nM) for Zellzyklusinhibierung in HeLa cells.

The compounds of the formula I according to the invention, in particular the compounds of the formula I according to the invention described in the preceding description, and / or their pharmaceutically acceptable salts are for the treatment, inhibition or control of the growth and / or proliferation of tumor cells and associated diseases suitable. Accordingly, they are useful for cancer therapy in warm-blooded vertebrates, i. of mammals and birds, in particular in humans, but also in other mammals, in particular useful and skin animals, such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison etc.), horses and birds, such as chicken, turkey , Duck, goose, guinea fowl and the like.

In particular, the compounds of the formula I according to the invention, especially the compounds of the formula I according to the invention which are described as preferred in the preceding description, and / or their pharmaceutically acceptable salts are suitable for the therapy of cancer or cancerous diseases of the following organs. net: chest, lung, intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, esophagus, stomach, ovaries, pancreas, liver and brain.

The pharmaceutical compositions according to the invention contain, in addition to the compounds I according to the invention and / or their pharmaceutically acceptable salt, at least optionally a suitable carrier. Suitable carriers include, for example, the solvents, carriers, excipients, excipients and the like commonly used for pharmaceutical formulations, which are exemplified below for single modes of administration.

The compounds I according to the invention can be administered in the usual way, eg. As oral, intravenous, intramuscular or subcutaneous. For oral administration, for example, the active ingredient may be mixed with an inert diluent or with an edible carrier; it can be embedded in a hard or soft gelatin capsule, pressed into tablets or mixed directly with the food / feed. The active ingredient may be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, troches, pills, capsules, suspensions, juices, syrups and the like. Such preparations should contain at least 0.1% active ingredient. The composition of the preparation may of course vary. It usually contains from 2 to 60% by weight of active compound, based on the total weight of the particular preparation (dosage unit). Preferred formulations of the compound I according to the invention contain 10 to 1000 mg of active ingredient per oral dosage unit.

The tablets, troches, pills, capsules and the like may also contain the following ingredients: excipients such as tragacanth, acacia, corn starch or gelatin, excipients such as dicalcium phosphate, disintegrants such as corn starch, potato starch, alginic acid and the like, lubricants such as magnesium stearate, sweetener, such as sucrose, lactose, or saccharin, and / or flavorants such as peppermint, vanilla, and the like. Capsules may also contain a liquid carrier. Other substances that change the nature of the dosing unit can also be used. For example, tablets, pills and capsules may be coated with shellac, sugar or mixtures thereof. Syrups or juices may contain, in addition to the active ingredient, also sugar (or other sweetening agents), methyl or propylparaben preservatives, a dye and / or a flavoring agent. Of course, the constituents of the active compound preparations in the quantities used must be pharmaceutically pure and non-toxic. Furthermore, the active compounds may be used as controlled-release preparations, e.g. As a sustained-release preparations formulated.

The active substances can also be administered parenterally or intraperitoneally. Solutions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents such as hydroxypropylcellulose. Dispersions can also be mixed with glycerol, liquid polyethylene glycols and mixtures thereof. from being made in oils. Often these preparations also contain a preservative to prevent the growth of microorganisms.

Preparations for injections include sterile aqueous solutions and dispersions as well as sterile powders for the preparation of sterile solutions and dispersions. The preparation must be sufficiently liquid so that it is injectable. It must be stable under the conditions of manufacture and storage and be protected against microbial contamination. The carrier can be a solvent or a dispersion medium, e.g. For example, water, ethanol, polyols (eg., Glycerol, propylene glycol or liquid polyethylene glycol), mixtures thereof and / or vegetable oils.

synthesis Examples

The instructions given in the following synthesis examples were used, with a corresponding modification of the starting compounds, to obtain further compounds of the formula I or the precursors thereof:

1) 5-Chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-1) a) 3-Cyclohexyl-3- Methyl oxo-2- (2,4,6-trifluorophenyl) -propionate 16 g (0.1 mol) of hexamethyldisilazane in 50 ml of tetrahydrofuran were treated with 65 ml (0.1 mol) at -20 ° C. 1, 6 n butyl lithium solution. in hexane. The mixture was stirred for 1 hour at -20 ° C and then cooled to -70 ° C. 10.2 g (50 mmol) of 2,4,6-trifluorophenylacetic acid methyl ester were then added dropwise and the mixture was stirred at -70 ° C. for 1 hour. Then added dropwise 7.4 g (50 mmol) of cyclohexanecarbonyl chloride and allowed to warm to room temperature. Then, the reaction mixture was added with water and the organic phase was extracted with methyl t-butyl ether. The organic phase was then concentrated and the residue was filtered off with suction with cyclohexane / methyl-t-butyl ether mixtures over silica gel. Then the solvents were evaporated off, whereby a colorless solid precipitated (presumably Li salt of the product). The solid was separated and the mother liquor was purified by column chromatography with cyclohexane / methyl t-butyl ether mixtures. This gave 12 g (76%) of the title compound as a colorless oil. The filtered solid was taken up with dil. Hydrochloric acid and methyl t-butyl ether, the organic phase was dried and concentrated. An additional 2.7 g (17%) of the title compound was obtained as a colorless oil. ( ¹ H-NMR (CDCl ₃ , δ in ppm): 13 "5 (s, 1H); 6.7 (t, 2H); 3.7 (s, 3H); 1.95 (m, 1H) 1, 75 (d, broad, 2H); 1, 6 (m, 5H); 1, 2 (m, 1H); 1, 05 (m, 2H)

b) 7-Cyclohexyl-5-hydroxy-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-7)

13.5 g (40 mmol) of methyl 3-cyclohexyl-3-oxo-2- (2,4,6-trifluoro-phenyl) -propionate (Example 1.a), 10 g of tributylamine and 4.3 g (40 mmol) of 3-amino-4-cyanopyrazole heated to about 160 ° C, with a low-boiling liquid distilled off. It was then cooled and the reaction mixture was stirred with a mixture of isopropanol and diisopropyl ether. The solid was discarded and the mother liquor was concentrated. Then the residue was taken up in ethyl acetate, the organic phase extracted with dil. Hydrochloric acid and water, dried over magnesium sulfate and concentrated the organic phase. The residue was purified by column chromatography with methylene chloride-cyclohexane and ethyl acetate mixtures. This gave 6.7 g (42%) of the title compound as a pale solid

c) 5-Chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-1)

5.5 g (14.8 mmol) of 7-cyclohexyl-5-hydroxy-6- (2,4,6-trifluorophenyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile (Example 1.b ), 50 ml of phosphorus oxychloride, 1.2 g of orthophosphoric acid and 1.8 g of pyridinium hydrochloride were heated to 120 ° C. for 72 hours. Subsequently, the excess phosphorus oxychloride was distilled off, the residue was taken up in methyl t-butyl ether and the organic phase was carefully hydrolyzed with water. Then, the organic phase was extracted with sodium bicarbonate sol. To precipitate a solid which was discarded. The organic phase was dried over magnesium sulfate and concentrated and the residue was purified by column chromatography with cyclohexane / methyl t-butyl ether mixtures. 4 g (69%) of the title compound were obtained as a yellow solid.

2) 7-Cyclohexyl-5-methoxy-6- (2,4,6-trifluorophenyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-2) 0.6 g (1, 5 mmol) 5-chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (Example 1.c), 5 ml of methanol and 0, 3 g (1.6 mmol) of 30% strength methanolic Na-methanolate solution. were stirred overnight at room temperature. Subsequently, the reaction mixture was diluted with methylene chloride and the organic phase was suctioned off on silica gel, rinsing with methyl t-butyl ether. The organic phase was evaporated, the residue crystallized and was filtered off with suction. There was obtained 0.4 g (68%) of 0.4 g of the title compound as a colorless solid.

3) 5-Cyano-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-3) 0.4 g (1 mmol) 5-Chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (Example 1.c), 5 ml acetonitrile and 0.8 g Tetrabutylammonium cyanide was stirred overnight at room temperature. The reaction mixture was then diluted with methyl t-butyl ether and filtered with suction through silica gel. The organic phase was concentrated, the residue obtained crystallized and was triturated with diisopropyl ether / isopropanol. 0.3 g (78%) of the title compound was obtained as a beige solid. 4) 7-Cyclohexyl-5-methyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-4) a) 2- [3-cyano 7-cyclohexyl-6- (2,4,6-trifluoro-phenyl) -pyrazolo [1,5-a] pyrimidin-5-yl] -malonic acid dimethyl ester 1, 3 g (10 mmol) of dimethyl malonate in 10 ml of acetonitrile added with 0.15 g (5 mmol) of sodium hydride. The mixture was stirred at room temperature for about 15 minutes and 0.6 g (1.5 mmol) of 5-chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1, 5-a] was added. pyrimidine-3-carbonitrile (Example 1.3.) and heated under reflux for 5 hours. A red-yellow solid precipitated, which was filtered off with suction, washed with methylene chloride and discarded. The organic phase was washed with dil. Hydrochloric acid and water and concentrated. The residue was purified by column chromatography with cyclohexane / methyl-t-butyl ether mixtures to give 0.25 g (34%) of the title compound as a pale solid. ¹ H NMR (CDCl ₃ , δ in ppm): 8.4 (s, 1H); 6.9 (t, 1H); 4.7 (s, 1H); 3.75 (s, 6H); 2.8 (m, very wide, 1H); 2.45 (m, very wide, 2H); 1, 85 (d, broad, 2H); 1, 7 (m, 3H); 1, 2 (m, 3H)

b) 7-Cyclohexyl-5-methyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carbonitrile (C-4)

0.2 g (0.4 mmol) of 2- [3-cyano-7-cyclohexyl-6- (2,4,6-trifluorophenyl) pyrazolo [1,5-a] pyrimidin-5-yl ] -malonic acid dimethyl ester (Example 4.1.) 0.1 g (2.3 mmol) of lithium chloride and 0.1 g (5.5 mmol) of water in 5 ml of dimethyl sulfoxide were heated to 120 ° C for 4 hours. Then again added 0.1 g of lithium chloride and 0.1 g of water and stirred for an additional 8 hours at 120 ° C. It was then allowed to cool, the reaction mixture diluted with water and the aqueous phase extracted with methyl t-butyl ether. The combined organic phases were concentrated and the residue was purified with acetonitrile / water mixtures by preparative MPLC over silica gel RP-18. 0.1 g (67%) of the title compound was obtained as a pale solid.

5) 5-Chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) -pyrazolo [1,5-a] pyrimidine-3-carboxylic acid amide (C-5) and 5-chloro-7 -cyclohexyl-6- (2,4,6-trifluoro-phenyl) -pyrazolo [1,5-a] pyrimidine-3-carboxylic acid methyl ester (C-6)

In a solution of 0.5 g (1.3 mmol) of 5-chloro-7-cyclohexyl-6- (2,4,6-trifluorophenyl) pyrazolo [1, 5-a] pyrimidine-3-carbonitrile ( Example 1.3) in 10 ml of methanol was introduced at 0 ° C hydrogen chloride. The mixture was stirred overnight at room temperature, the reaction mixture was diluted with water and the aqueous phase was extracted with ethyl acetate. The combined organic phases were extracted with water, dried over magnesium sulfate and concentrated. The residue was purified by preparative MPLC over silica gel RP-18 (eluent: acetonitrile / water mixtures) to give 0.2 g (38%) of the title compound C-5 and 0.2 g (36%) of the title compound C-6 ,

The remaining compounds were prepared analogously.

Examples of the effect against harmful fungi The fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:

The active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing based on ethoxylated alkylphenols) in the volume ratio solvent-emulsifier from 99 to 1 ad 10 ml. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.

O

K5 CO

K5 CO O

K5 CO

Examples of the effect against harmful fungi

The fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:

Greenhouse test

Food supply

The active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient which was mixed with a mixture of acetone and / or DMSO and the emulsifier Wettol (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.

Use Example 1 - Activity against wheat powdery mildew caused by Erysiphe (syn. Blumeria) graminis forma specialis. tritici

Leaves of potted wheat seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below. The suspension or emulsion was prepared as described above. Twenty-four hours after the spray coating had dried, the leaves were dusted with spores of the wheat powdery mildew (Erysiphe [syn. Blumeria] graminis forma specialis tritici). The test plants were then placed in a greenhouse at temperatures between 20 and 24 ° C and 60 to 90% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.

In this test, the plants treated with 250 ppm of Compound C-2 showed a maximum of 5% infestation, while the untreated plants were 90% infected.

Application Example 2 - Activity against gray mold on pepper leaves caused by Botrytis cinerea at 1 day of protective application

Paprika seedlings were, after 2-3 leaves had developed well, sprayed to drip point with an aqueous suspension in the drug concentration below. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea in 2% biomalt solution. Subsequently, the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%. In this test, the plants treated with 250 ppm of Compound C-18 showed a maximum of 7% infestation, while the untreated plants were 100% infested.

Use Example 3 - Activity against tomato late blight on tomatoes caused by Phytophthora infestans in protective treatment

Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were inoculated with an aqueous sporangia suspension of Phytophthora infestans. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.

In this test, the plants treated with 250 ppm of Compound C-2 showed a maximum of 5% infestation, while the untreated plants were 90% infected.

microtest

The active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.

Application Example No. 4 Activity against the causative agent of the gray mold Botrytis cinerea in the microtiter test

The stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance 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 absorption photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

The measured parameters were compared with the growth of the drug-free control variant and the fungal and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

In this assay, the relative growth of the spore suspension was less than or equal to 12% using 31 ppm of the C-1, C-3, C-4, C-5, C-6, C-8 or C-9 agents and smaller equal to 15% when using 125 ppm of C-7, C-13 "C-14 or C-17. Application Example No. 5 - Activity against the causative agent of the Septoria leaf drought Septoria tritici in the microtiter test

The stock solution is 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. With an absorption photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

The measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

In this test, the relative growth of the spore suspension was less than or equal to 8% using 31 ppm of the C-1, C-3, C-4, C-5, C-6, C-8 or C-9 agents; less than or equal to 3% using 125 ppm of C-7, C-13, C-14 or C-17, and 0% using 8 ppm of C-15.

Application Example No. 6 Activity against the causative agent of the late blight Phytophthora infestans in the microtiter test

The stock solution is pipetted into a microtiter plate (MTP) and diluted to the indicated drug concentration with an aqueous, pea-based, mushroom 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 absorption photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

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.

In this test, the relative growth of the spore suspension was less than or equal to 3% using 125 ppm of drug C-11.

Claims

claims

1. Compounds of the formula I

wherein the substituents have the following meanings:

R ¹ - is hydrogen, halogen, cyano, nitro, _Ci-C8-alkyl, d-Cs-haloalkyl, Ci-Cs-hydroxyalkyl, _{Ci-C8-alkoxy-Ci-C 8} alkyl, C ₂ -C ₈ - alkenyloxy-Ci-C ₈ - alkyl, C ₂ -C ₈ alkynyloxy-Ci-C ₈ alkyl, C ₃ -C ₈ cycloalkyloxy-Ci-C ₈ alkyl, C ₈ - alkoxy Ci-C ₈ - alkoxy-Ci-C ₈ alkyl, aryloxy-Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ -

Haloalkenyl, C ₂ -C ₈ -alkyl kinyl, C ₂ -C ₈ haloalkynyl, C ₈ -alkoxy, C ₈ - haloalkoxy, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl, hydroxyimino or a rest

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

- CW ⁵ (= 0), 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 ⁸ , C (O) SW ⁸ ,

C (S) SW ⁸ , SW ⁷ , SOW ⁷ , SO ₂ W ⁷ , SO ₃ W ⁸ , 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 d-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, C ₃ -C ₈ -cycloalkyl,

C ₃ -C ₈ cycloalkenyl, C ₆ -C ₄ -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 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 metal equivalent, an ammonium ion of the formula (NR ^α R ^β R ^γ R ^δ ) ⁺ , where R ^α , R ^β , R ^γ and R ^δ are each independently H, C 1 -C 10 -alkyl, C 1 -C 10 -alkyl Hydroxyalkyl, aryl or aryl-Ci-C ₄ alkyl, Ci-C ₈ alkyl, (CHR ^w -CHR ^w -O) _m - (C _r C ₄ ) alkyl with R ^W = H or CH ₃ and m = 1 to 6, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -alkynyl, C ₃ -C ₈ -cycloalkyl,

C ₃ -C ₈ cycloalkenyl, C ₆ -C ₄ aryl or C ₆ -Ci4-aryl-Ci-C ₈ alkyl;

W ⁶ , W ⁷ , W ⁸ or a cycle formed from two radicals W ⁷ or a radical W ⁷ and a radical W ⁶ can each independently carry one, two, three or four identical or different groups R ^a ;

saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclyl containing one, two, three or four heteroatoms selected from N, O and S, which may carry 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 -alkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ Alkynyl, C ₂ -C ₈ -

Haloalkynyl, C ₄ -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, C2-C8-haloalkynyloxy, _C3-C8 cycloalkyl, _C3-C8 halocycloalkyl, Ca-Cs-cycloalkenyl, _C3-C8 cycloalkoxy, C3-C ₈ -Halogencycloalkoxy, Ca-Cs-cycloalkenyloxy, Cs-CIO Bicycloalkyl, C 1 -C ₈ -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 8 -alkylaminothiocarbonyloxy, C ₁ -C 8 -alkylaminothiocarbonyl, C ₁ -C -alkylaminothiocarbonyl, C ₁ -C 6 -alkylene, oxy-C ₂ -C ₄ -alkylene, oxy-Ci-C ₃ -alkylenoxy, = CH ₂ , = CH (Ci-C _β - alkyl), = C (Ci-Cβ-alkyl) ₂ , imino (= NH), (Ci-C ₄ Alkoxy) imino (= N- (ci)

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 ¹ X = N-OA), N (A) A, N (A) -C (= O) -A, N (A ") -C (= O) -N (A ') A, S (= O) _m -A, S (= O) _n -OA, S (= O) _n -N (A') A, -Si (Ci-C6 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 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, Ci-Cs-alkyl, C ₂ -Cs-yl alkene, C ₂ -C ₈ kinyl -alkyl, C ₄ -Cio-alkadienyl, C ₃ -C ₈ cycloalkyl , C ₃ -C ₈ -CyCIo- alkenyl, Cs-Cio-bicycloalkyl, C ₈ alkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ -

Alkynyloxy, C 3 -C ₈ -cycloalkoxy, C 3 -C ₈ -cycloalkenyloxy, aminothiocarbonyl, C 1 -C ₈ -alkylcarbonyloxy, C 1 -C ₈ -alkylaminothiocarbonyl, di-C ₈ -alkylaminothiocarbonyl, C 1 -C ₈ -alkylthio, -C ₈ 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-Cδ-alkoxy , Ce-Cu-aryl-Ci-Ce-alkyl, five- to ten-membered saturated, 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 ¹ X = N-OA), N (A ¹ JA; partially or completely halogenated aliphatic, alicyclic or aromatic groups and / or may be substituted by Ci-C ₈ alkyl and / or Ci-C ₈ haloalkyl groups;

where m, n, A, A and A "mean:

m is 0, 1 or 2; n 1 or 2;

A, A ', A "independently of one another, hydrogen, CrC ₈ alkyl, C ₂ -C ₈ alkene yl, C ₂ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, Phenyl, where the organic radicals may be partially or completely halogenated and / or monosubstituted or polysubstituted by nitro, cyanato, cyano, C 1 -C ₄ -alkoxy, A and A 'may also be used together with the atoms to which they are attached for a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from

Group O, N and S, which may carry 1 or 2 identical or different substituents R ^a , wherein R ^{a is} as defined above

R ² is hydrogen, halogen, cyano, C -C -alkyl ₈ -alkyl, Ci-C ₈ haloalkyl, CrC oxy ₈ -AIk-, -C ₈ -haloalkoxy, CrC ₈ alkylthio, CrC ₈ alkylsulfinyl, CrC 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 and R ^{a is} as defined above;

X is hydrogen, halogen, hydroxy, cyano, N (A ') A, -C ₈ alkoxy, CrC genalkoxy ₈ -HaIo-, -C ₈ alkylthio, CrC ₈ alkylsulfinyl, CrC ₈ alkylsulfonyl, CrC ₈ - alkyl, CrC ₈ haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ - alkynyl, C ₂ -C ₈ haloalkynyl, cyano-CrC ₄ alkyl, Ci-C ₄ alkoxy CrC ₄ -alkyl; wherein A and A 'are as defined above;

Y - 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, said heterocycle being 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, CrC ₈ - haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ - al kinyl, C ₂ -C ₈ - haloalkynyl, C ₄ -Cio-alkadienyl, C ₄ -Cio-Halogenalkadienyl, CrC oxy ₈ -AIk-, d-Cs-halogenoalkoxy, CrC ₈ alkylcarbonyloxy, CrC ₈ alkylsulphonyl oxy, C ₂ -C 8 alkenyloxy, C ₂ -C 8 haloalkenyloxy, C ₂ -C 8 alkynyloxy, C ₂ -C 8 haloalkynyloxy, C ₃ -C 8 cycloalkyl, C ₃ -C 8 halocycloalkyl, C ₃ -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl , C ₃ -C 8 -cycloalkoxy, C ₃ -C 6 -cycloalkenyloxy, hydroxyimino-C ₁ -C 8 -alkyl, C ₁ -C ₆ -alkylene, C ₁ -C ₄ -alkylene, oxy-C ₁ -C ₃ -alkyleneoxy, C ₁ -C 8 -alkoximino -C-Cs-alkyl, C ₂ -Cs

Alkenyloximino-Ci-Cs-alkyl, C2-C8-alkynyloximino-Ci-C ₈ -alkyl, S (= O) _m A ¹ , C (= O) A ² , C (= S) A ² , NR ⁵ R ⁶ , NR ⁵ O = 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 m, A ¹ , A ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ^{13 are}

m is 0, 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,

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

Cs-alkoxy, Cis-Cs-haloalkoxy, C ₂ -C 8 -alkenyloxy, C ₂ -Cs-haloalkenyloxy, C ₂ -C 8 -alkynyloxy, C ₂ -C 8 -haloalkynyloxy, Ca-Cs-cycloalkyl, C ₃ -C 8 -halocycloalkyl, C ₃ -Cs -cycloalkoxy, C3-C8-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 -alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl, C ₁ -C ₈ cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ -C ₈ -cycloalkenyl or C ₃ -C ₈ -halocycloalkenyl mean,

R ⁵ and R ⁶ , R ⁸ and R ⁹ , R ¹⁰ and R ¹¹ and / or R ¹² and R ¹³ may also be taken together with the nitrogen atom to which they are attached, a four-, five- or six-membered saturated or partially unsaturated Ring which is unsubstituted or substituted with one, two, three or four identical or different substituents R ^a , wherein R ^{a is} as defined above;

wherein the aliphatic and / or alicyclic and / or heterocyclic see groups of the radical definitions of L in turn can carry one, two, three or four identical or different groups R ^L ; R ^{L is} halogen, cyano, Ci-C ₈ alkoxy, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ -alkyl kinyl- oxy, _C3-C8 cycloalkyl, Cs-Cs-cycloalkenyl, Ca-Cs-cycloalkyloxy , C ₃ -C 8 -cycloalkenyloxy, C ₁ -C 8 -alkoximino, C ₂ -C 8 -alkenyloxyimino, C ₂ -Cs-AlKIn-yloxyimino, C ₁ -C 8 -alkoximino-C ₁ -C 8 -alkyl, C ₂ -C 8 -alkenyloximino-ci C 8 alkyl, C ₂ -C 8 alkynyloximino-C ₁ -C 8 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-C3-alkyleneoxy, wherein R ^{a is} as defined above;

Z is C ₁ -C 10 -alkyl, C ₁ -C 10 -haloalkyl, C ₂ -C 10 -alkenyl, C ₂ -C 10 -haloalkenyl,

C ₂ -Cio-alkynyl, C ₂ -Cio-haloalkynyl, C3-Ci ₂ cycloalkyl, C3-Ci ₂ cycloalkyl-halo, _C3-Ci2 cycloalkenyl, C3-Ci ₂ halocycloalkenyl, phenyl, halo- genphenyl, Naphthyl, halonaphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic carbon-bonded heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and Sulfur, or C 1 -C 4 -alkyl, which is represented by 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, Substituted nitrogen and sulfur, which may carry 1, 2 or 3 radicals R ^a ; wherein Z may contain one, two, three or four identical or different groups R ^a ; wherein R ^{a is} as defined above;

and the agriculturally or pharmaceutically acceptable salts thereof.

2. Compounds according to claim 1, wherein Z is not phenyl.

3. Compounds according to claim 1 or 2, wherein Z is not an aromatic heterocycle.

4. A compound according to any one of the preceding claims, wherein Z is CrC ₄ -AlkVl, C ₅ -C ₆ cycloalkyl or by a 5- or θ-membered heterocyclyl radical having 1, 2 or 3 heteroatoms as ring members selected from O, N and S, substituted dC ₂ alkyl, wherein the heterocyclyl group 1 or 2 substituents se- lected from Ci-C ₄ alkyl, and -C ₄ haloalkyl, can carry.

5. Compounds according to any one of the preceding claims, wherein Y is a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle having one, two, three or four heteroatoms from the group Oxygen, nitrogen and sulfur, wherein the heterocycle is unsubstituted or substituted with one, two, three or four identical or different substituents L as defined in claim 1.

6. Compounds according to any one of claims 1 to 3, wherein 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.

7. Compounds according to claim 6, wherein Y means: 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, 2-fluoro-3-methoxyphenyl or 4- (4- methylpiperazin-1-yl) -phenyl.

8. Compounds according to one of claims 1 to 3, wherein 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 a two, three or four identical or different groups R ^{a can} carry and / or two bonded to the same or adjacent atoms or ring atoms substituents for Ci-Cβ-alkylene, oxy-C 2 -C 4 -alkylene or oxy-Ci-C3-alkylenoxy as defined in claim 1.

9. Compounds according to any one of claims 1 to 7, wherein Y is not unsubstituted alkyl or CF ₃ .

10. Compounds according to any one of the preceding claims, wherein X is halogen, hydroxy, cyano, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy,} Ci-C ₈ alkyl, CrC ₈ -

Haloalkyl, piperidin-1-yl or pyrrolidin-1-yl, where the two last-mentioned radicals may be unsubstituted or bear one or two radicals can, which are selected from -C ₄ -alkyl and -C ₄ haloalkyl.

1 1. Compounds according to claim 10, wherein X is halogen, hydroxy, -C ₄ -alkoxy or CrC is ₄ -haloalkoxy.

12. A compound according to any one of claims 1 to 10, wherein X is Ci-C4-alkyl or Ci-C4-haloalkyl.

13. Compounds according to any one of claims 1 to 10, wherein X is cyano.

14. Compounds according to any one of claims 1 to 10, wherein X is piperidin-1-yl or pyrrolidin-1-yl, which may be unsubstituted or one or two

May bear radicals selected from C 1 -C ₄ alkyl and C 1 -C ₄ haloalkyl.

15. Compounds according to one of the preceding claims, wherein R ^{1 is} hydrogen, chlorine, nitro, bromine, CSNH ₂ , CONH ₂ , iodine, CHO, CH = NOCH ₃ , cyclopropyl, COOCH ₃ , CH = NOH or cyano.

16. A compound according to claim 15, wherein R ^{1 is} hydrogen, CONH ₂ , CHO, COOCH ₃ or cyano.

17. Compounds according to any one of the preceding claims, wherein R ^{1 is} not hydrogen.

A fungicidal composition comprising at least one compound of the formula I according to any one of the preceding claims and / or an agriculturally acceptable salt thereof and a solid or liquid carrier.

19. A composition according to claim 18, further comprising a further fungicidal, insecticidal and / or herbicidal active ingredient.

20. Seed comprising at least one compound according to any one of claims 1 to 17 in an amount of 1 to 1000 g per 100 kg.

21. A combination of at least one compound of the formula I according to any one of claims 1 to 17 and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal and / or herbicidal active ingredient.

22. A method for controlling phytopathogenic fungi, comprising the treatment of fungi and / or to be protected from fungal attack materials, plants, soils and / or seeds with an effective amount of at least one compound according to any one of claims 1 to 17 and / or an agricultural tolerable salt thereof.

23. Use of at least one compound of the formula I according to any one of claims 1 to 17 and / or an agriculturally acceptable salt thereof for controlling phytopathogenic fungi.

24. A process for the preparation of the compounds according to any one of claims 1 to

1 1 and 15 to 17, in which X is halogen, by reacting dihalopyrazolopyrimidines of the formula II,

with organometallic reagents M ^w (-Z) _w , where R ¹ , R ² , Y and Z have the meanings as for the compounds of the formula I in one of the claims

1 to 17, Hal is halogen and M is a metal ion of valency w.

25. A process for preparing a compound according to any one of claims 1 to 10, 12 and 15 to 17, wherein X is d-Cβ-alkyl, comprising the step:

(a) reacting a corresponding compound of the formula I in which X is halogen, with a malonate of the formula IVe

to a connection

wherein X "is hydrogen or C 1 -C ₇ -alkyl and R is C 1 -C ₄ -alkyl and Y, Z, R ¹ and R ^{2 are} as defined for compounds of the formula I, (b) hydrolysis of the in step (a and (c) decarboxylating the hydrolysis product obtained in step (b).

26. Compounds of formula VI according to claim 25 and the hydrolysis product thereof.

27. A pharmaceutical composition comprising at least one compound of the formula I as defined in any one of claims 1 to 17 and / or at least one pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.

28. Use of compounds of the formula I as defined in any one of claims 1 to 17 or their pharmaceutically acceptable salts for the manufacture of a medicament for the treatment of cancer.