EP1853607A2 - Pyrazolopyrimidines - Google Patents

Abstract

The invention relates to the pyrazolopyrimidines of formula (I), wherein R<SUP>1</SUP>, R<SUP>2</SUP>, R<SUP>3</SUP>, R<SUP>4</SUP>, R<SUP>5</SUP>, and X are defined as in the description. The invention also relates to methods for producing said substances and to the use thereof for controlling undesirable microorganisms.

Description

pyrazolopyrimidine

The invention relates to pyrazolopyrimidines, a process for their preparation and their use for controlling unwanted microorganisms.

It is already known that certain pyrazolopyrimidines have fungicidal properties (see for example WO-A 02/048 151, WO-A 04/000844, WO-A 04/106 341 or WO-A 05/082 907).

However, since the ecological and economic demands on modern fungicides are constantly increasing, for example with regard to spectrum of action, toxicity, selectivity, application rate, formation of residues and favorable manufacturability, and in addition, e.g. If problems with resistances can occur, there is the constant task of developing new fungicides which, at least in some areas, have advantages over the known ones.

New pyrazolopyrimidines of the formula (I) have now been found

in which the symbols have the following meanings:

R ¹ is hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or optionally substituted heterocyclyl, hydroxy, optionally substituted alkoxy, amino, optionally substituted alkylamino or optionally substituted dialkylamino;

R ² is hydrogen or alkyl;

or

R ¹ and R ² , together with the nitrogen atom to which they are attached, are an optionally substituted heterocyclic ring;

R- * is optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted Cycloalkenyl, optionally substituted aralkyl, halogen, an optionally substituted amino group, optionally substituted (C ₁ -C ₆ ) -alkoxy, optionally substituted (C ₁ -C ₆ ) -alkylthio, optionally substituted (C 9 -C 10) -acyloxy, optionally substituted (C ₁ -C ₆ ) -alkylthio Cio) -arylthio, optionally substituted heterocyclyloxy, optionally substituted (C ₆ -C ₁₀ ) -aryl (C ₁ -C ₄ ) -alkoxy, optionally substituted (C ₆ -C ₁₀ ) -aryl (C ₁ -C ₄ ) -alkylthio, optionally substituted heterocyclyl- (C ₁ -C ₄ ) -alkoxy, optionally substituted heterocyclyl- (C ₁ -C ₄ ) -alkylthio, C (S) OR ⁸ , C (O) SR ^S or C (S) SR ⁸ ;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, halogen, optionally halogen-substituted alkyl, optionally substituted by halogen, cycloalkyl, O- (C _{r C4)} alkyl or S (O) _0-2 (Ci-C ₄₎ -alkyl;

X is halogen, cyano, hydroxy, optionally substituted alkyl, (C ₁ -C ₃ ) -haloalkyl, optionally substituted alkoxy, optionally substituted phenyl, optionally substituted alkylthio, optionally substituted alkylsulfinyl or optionally substituted alkylsulfonyl;

R ⁶ is H, a cation, for example an optionally alkyl or arylalkyl substituted

Ammonium ion, optionally substituted alkyl, optionally substituted

Alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl and optionally substituted cycloalkenyl, optionally substituted aryl and optionally substituted arylalkyl;

R ⁷ is COR ⁸ , S (O) _1-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , where R ^{8 may be the} same or different, saturated, partially or fully, unsaturated or aromatic, optionally substituted 5- or 6-membered heterocyclyl which, if present, contains 1 or up to three further heteroatoms selected from N, S and / or O atoms, oxygen atoms not being adjacent;

R ⁸ is independently H, optionally substituted alkyl, haloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl or optionally substituted aralkyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent; or

R ⁶ and R ⁸ together with the N-CO or NS (O) _1-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen may contain, wherein oxygen atoms may not be adjacent;

and agrochemically active salts thereof.

Pyrazolopyrimidines of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in the protection of materials.

The compounds of the formula (I) can be used both in pure form and as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro, and optical isomers, such as R and S isomers or Atropisomers, but optionally also of tautomers. The invention includes both the pure isomers and their mixtures.

Depending on the nature of the substituents defined above, the compounds of formula (I) have acidic or basic properties and may form salts, optionally also internal salts. If the compounds of the formula (I) bear hydroxy, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts. Examples of suitable bases are hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having (C 1 -C ₄ ) -alkyl radicals, mono-, di- and Trialkanolamine of (C _r C ₄ ) -alkanols, choline and chlorcholine. If the compounds of the formula (I) bear amino, alkylamino or other basic-property-inducing groups, these compounds can be reacted with acids to form salts. Suitable acids are, for example, mineral acids, such as hydrochloric, sulfuric and phosphoric acids, organic acids, such as acetic acid or oxalic acid, and acidic salts, such as NaHSO ₄ and KHSO ₄ . The salts thus obtainable also have fungicidal properties.

The pyrazolopyrimidines of the invention are generally defined by the formula (I).

Preference is given to compounds of the formula (I) in which R ^{6 has} one of the following meanings:

a ¹ : H,

a ² : cation, a ³ : optionally substituted alkyl,

a ⁴ : optionally substituted alkenyl,

a ⁵ : optionally substituted alkynyl,

a ⁶ : optionally substituted cycloalkyl,

a ⁷ : optionally substituted cycloalkenyl,

a ⁸ : optionally substituted aryl or

a ⁹ : optionally substituted arylalkyl,

Likewise preferred are compounds of the formula (I) in which R ^{7 has} one of the following meanings:

a ¹ ': COR ⁸ ,

a ^{2 '} : SO, - ₂ R ⁸ ,

a ³ : cyano,

a ^{4 '} : COOR ⁸ ,

a ⁵ : CON (R ⁸ ) ₂ , where the radicals R ^{8 may be} identical or different, or

a ⁶ : saturated, partially unsaturated or aromatic, optionally substituted 5- or 6-membered heterocyclyl,

Likewise preferred are compounds of the formula (I) in which R ⁶ = H or a cation and R ^{7 has} one of the following meanings:

a ¹ ': COR ⁸ ,

a ^{2 '} : SOr ₂ R ⁸ ,

a ³ : cyano,

a ^{4 '} : COOR ⁸ ,

a ⁵ : CON (R ⁸ ) ₂ , where the radicals R ^{8 may be} identical or different, or a ⁶ : saturated, partially unsaturated or aromatic, optionally substituted 5- or 6-membered heterocyclyl,

Likewise preferred are compounds of the formula (I) in which R ^{2 has} one of the following meanings:

Likewise preferred are compounds of the formula (I) in which R ^{7 has} one of the following meanings:

Preference is furthermore given to compounds of the formula (I) in which

bl) R ^{3 is} optionally substituted aryl, or

b ² ) R ^{3 is} optionally substituted heterocyclyl, or b ³ ) R ^{3 is} optionally substituted alkyl, or

b ⁴ ) R ^{3 is} optionally substituted alkenyl, or

b ⁵ ) R ^{3 is} optionally substituted alkynyl, or

b ⁶ ) R 3 is optionally substituted cycloalkyl, or

b ⁷ ) R 3 is optionally substituted aralkyl, or

b ⁸ ) R 3 is an optionally substituted amino group, or

b ⁹ ) R 3 is optionally substituted (C ₁ -C ₈ ) -alkylthio, or

b ¹⁰ ) R 3 is optionally substituted (C ₁ -C ₈ ) -alkoxy.

Likewise preferred are compounds of the formula (I) in which R 3 has one of the following meanings:

Preference is furthermore given to those substances of the formula (I) in which one or more symbols have one of the preferred meanings given below, i.

R ¹ is hydrogen, alkyl of 1 to 10 carbon atoms which is unsubstituted or monosubstituted, monosubstituted or differently substituted by halogen, cyano, hydroxy, Alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono- or dialkylamino having in each case 1 to 4 carbon atoms, or

R ¹ is alkenyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 Carbon atoms, amino, mono- or dialkylamino each having 1 to 4

Carbon atoms, or

R ¹ is alkynyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 Carbon atoms, amino, mono- or dialkylamino each having 1 to 4

Carbon atoms, or

R1 is cycloalkyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen and / or alkyl of 1 to 4

Carbon atoms, or

R ¹ is saturated or unsaturated heterocyclyl having 3 to 10 ring members and 1 to 3

Heteroatoms, such as nitrogen, oxygen urtd / or sulfur, wherein the heterocyclyl is unsubstituted or monosubstituted or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxy,

Alkoxy of 1 to 4 carbon atoms and / or mercapto;

R ² is hydrogen or alkyl of 1 to 6 carbon atoms;

R ¹ and R ² , together with the nitrogen atom to which they are attached, are a saturated or unsaturated heterocyclic ring having from 3 to 8 ring members, the heterocycle optionally containing one further nitrogen, oxygen or sulfur atom as ring member, and wherein Heterocycle may be unsubstituted or substituted up to three times by

.Fluor, chlorine, bromine, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4

Carbon atoms and 1 to 9 fluorine and / or Chloratόmen, hydroxy, alkoxy having 1 to 4

Carbon atoms, haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms and / or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms; R ³ is C ₁ -C ₁₀ -alkyl, C ₂ -C 6 -alkenyl, C ₂ -C ₁ 0 -alkyl, C ₃ -C ₈ -cycloalkyl, phenyl-C 1 -C ₁ (alkyl) in which R ^{3 is} unsubstituted or partially or fully halogenated and / or optionally carries one to three radicals from the group R ^x , or C ^ C ^ -haloalkyl which optionally carries one to three radicals from the group R ^x , and R ^x cyano, nitro, hydroxy , C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl,

C ₁ -C ₆ -AHCyIAiO, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -acrylic acid, C ₁ -C ₆ -halogenoalkylsulphinyl, C ₁ -C ₆ -alkylsulphonyl, C ₁ -C ₆ -haloalkylsulphonyl, C ₁ -C ₆ -alkylcyclohexyl, di- C ^ Coe-alkylamino, _C2-C6 alkenyl, _C2-C6 alkenyloxy, C2-C ₆ -alkynyl, C ₃ -C ₆ oxy -AIkUIyI- and optionally halogenated oxy-C ₁ -C 4 alkyl C ₁ -C 4 alkenoxy, oxy-C ₁ -C ^ alkenyl-C ₁ -C 4 alkoxy, oxy-C ₁ -C 4 alky 1-C ₁ -C 4 alkyloxy, or

R ³ is phenyl, which may be monosubstituted, monosubstituted or differently substituted by one to four times

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;

in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

Cycloalkyl of 3 to 8 carbon atoms;

2,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-) linked in the 2,3-position, these being Radicals mono- or polysubstituted by identical or different substituents can be substituted by halogen, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; or

R ² is saturated or wholly or partially unsaturated or aromatic heterocyclyl having 3 to 8 ring members and 1 to 3 heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the heterocyclyl may be monosubstituted or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, Alkoxy of 1 to 4 carbon atoms,

Alkylthio having 1 to 4 carbon atoms, haloalkoxy having 1 to 4 carbon atoms, haloalkylthio having 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl having 3 to 6 carbon atoms and / or carboxyalkyl

or

R ³ is C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenylamino, C ₂ -C ₈ -alkynylamino, di-C ₁ -C ₆ -alkylamino, di-C ₂ -C 3 -alkenylamino, di-C ₂ - C ₈ -alkynylamino, C ₂ -C ₈ -alkenyl- (C ₂ -C ₈ ) -alkynylamino, C ₂ -C ₆ -alkynyl- (C ₁ -C ₈ -alkylamino, C ₂ -C ₈ -alkenyl- (C ₁ -C ₈ ) -alkylamino, Cg-C γ Q-aryl-amino, Cg-C i Q-aryl- (C ₁ -C ₆ ) -alkylamino, Cg-C i Q-aryl 1- (C ₁ -C 4) -alky 1- (C i -Cg) -alkylamino, heterocyclyl- (C ₁ -C ₆ ) -alkylamino or heterocyclyl- (C ₁ -C ₄ ) -alkyl- (C ₁ -C ₆ ) -alkylamino;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, halogen, unsubstituted or substituted by one or more halogen atoms (C ₁ -C ₄ ) alkyl, unsubstituted or substituted by one or more halogen atoms cyclopropyl; SCH ₃ , SOCH ₃ , SO ₂ CH ₃ or OCH ₃ .

X is H, fluorine, chlorine, bromine, CN, hydroxy, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, (Ci-CγValkyl or (Ci-C3) -haloalkyl;

R ⁶ is H, an alkali or alkaline earth metal, copper, NH 3, mono- (C ₁ -C ₁₀ ) -alkylammonium, di- (C ₁ -C ₁₀ ) -alkylammonium, tri- (C ₁ -C ₁₀ ) -alkylammonium, tetra- (C C ₁ -C ₁₀ ) -alkylammonium, where the alkyl radicals of the ammonium ions can be substituted by aryl or hydroxyl, cholinium, C ₁ -C -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ -C ₆ -cycloalkyl,

CrCg-cycloalkenyl, aryl, phenyl-C ₁ -C ₁₀ -alkyl, wherein R "is unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^x , or Ci-CiO'haloalkyl, optionally carries one to three radicals from the group R ^x , and R ^{x is} cyano, nitro, hydroxy, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C 9 -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkylsulfmyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkenyloxy, O-Cg-AIkUIyI, C ₃ -Cg -alkinyloxy and optionally halogenated oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkenoxy, oxyalkyl C ₁ -C ₄ -alkenyl-C ₁ -C ₄ -alkoxy, oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkyloxy and / or CONR ⁶ R ⁷ , CONR ⁷ OR ⁷ , COOR ⁸ , carboxy - (C 1 -C ₄ ) -alkyl;

R ⁷ is COR ⁸ , S (O) _1-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , wherein the radicals R ^{8 may be the} same or different, or

A, B, D, E, G are the same or different CR ⁹ , CR ⁹ R ⁹ , N, NR ⁹ , O or S with the proviso that at least one symbol is N, O or S, and that oxygen atoms are not adjacent ;

Y is C, CR ⁹ or N;

R ⁸ is independently H, C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, aryl, phenyl-C ₁ -C ₁₀ wherein R ⁸ unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^x , or C ₁ -C ₁₀ haloalkyl, which optionally one to three

Carrying radicals from the group R ^x, and R ^x is cyano, nitro, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C 3 -C 6 cycloalkyl, C ₁ -C ₆ -Älkoxy, C ₁ - C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ - C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -alkynyl, C ₃ -Cg -Alkmyloxy and optionally halogenated oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkenoxy, oxy-C ₁ -C ₄ -alkenyl-Ci- C4-alkoxy, oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ alkyloxy; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) _U 2 group to which they are attached form a 4-8 membered cycle which may contain one or more heteroatoms selected from sulfur, oxygen and / or nitrogen where oxygen atoms are not allowed to be adjacent; R ⁹ is R ⁷ , H, halogen, NR ⁷ ₂ , OH, SR ⁷ or OR ⁷ ;

Particular preference is given to those pyrazolopyrimidines of the formula (I) in which one or more of the symbols has one of the particularly preferred meanings given below,

R is hydrogen or a radical of the formula

stands,

where # denotes the point of attachment (these radicals can be present both in optically pure form "and in isomeric mixtures);

R ² is hydrogen, methyl, ethyl, propyl, or

R ¹ and R ² together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1 (2H) -pyridinyl or Tetrahydro-l (2H) -pyridazinyl, where these radicals are unsubstituted or substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl,

or

R ¹ and R ² , together with the nitrogen atom to which they are attached, are a radical of the formula

wherein

R 'is hydrogen or methyl,

R "is methyl, ethyl, fluorine, chlorine or trifluoromethyl,

m is the numbers 0, 1, 2 or 3, where R "is identical or different radicals, when m is 2 or 3,

R '"represents methyl, ethyl, fluorine, chlorine or trifluoromethyl

and

n is the numbers 0, 1, 2 or 3, where R '"is identical or different radicals, when n is 2 or 3.

R ³ is (C ₁ -C ₈ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₃ -C ₈ ) -cycloalkyl, wherein R ^{3 is} unsubstituted or substituted by an or a plurality of fluorine or chlorine atoms is substituted, benzyl or

R ³ is phenyl which may be monosubstituted to trisubstituted, identically or differently substituted by

Fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, ethynyl, AHyI, propargyl, methoxy, ethoxy, n- or i-propoxy, methylthio,

Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl,

Allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, di-fluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethinyloxy, trifluoroethinyloxy, chloroallyloxy, iodopropproxyloxy, methylamino, ethylamino, n- or i-propyl - amino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximino-methyl, memoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or by

1,3-propanediyl linked in the 2,3-position, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), where these radicals may be substituted one or more times, identically or differently by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl, carboxy and / or carboxymethyl

R.3 is pyridyl which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently monosubstituted by fluorine, chlorine, bromine, cyano, hydroxyl, mercapto,

Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R 3 is pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy,

Mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R3 is thienyl which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy,

Mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ² is C ₁ -C ₆ -alkylamino or di-C ₁ -C ₆ -alkylamino, or

R ² is thiazolyl which is linked in the 2-, 4- or 5-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, Methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1,2,4-triazolyl, N-pyrrolyl, or N-morpholinyl, each unsubstituted or one or - if possible - several times identical or different with fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, Methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoxyminomethyl, methoximinoethyl and / or trifluoromethyl,

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, Cl, F, CH ₃ , -CH (CH ₃ ) 2 or cyclopropyl; and

X is H, F, Cl, CN, unsubstituted or substituted by one or more fluorine or chlorine atoms C ₁ -C ₄ alkyl;

R ⁶ is H, Na, K, V ₂ Ca, V ₂ Mg, 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) ₃ NCH ₂ Ph, cholinium, (C _r C ₈₎ alkyl, (C ₃ -C ₆₎ - alkenyl, (C ₁ - C ₈₎ cycloalkenyl, (C _r C ₈₎ cycloalkyl, phenyl, benzyl;

R ⁷ is COR ⁸ , S (O) _1-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , where R ^{8 may be the} same or different, pyrrolyl, imidazolyl, pyrazolyl, 1,3,4 Triazolyl, thiazolyl, isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, oxazolyl, isoxazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2,4] -oxadiazin-3-yl, dioxazinyl, 5 , 6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group C ₁ -C ₄ - AIlCyI, C _r

C ₄ alkoxy and halogen;

R ⁸ is independently H, (C _r C ₈₎ alkyl, (C _r C ₈₎ haloalkyl, (C ₂ -C ₆₎ alkenyl, propargyl, (C ₃ -C ₈₎ cycloalkyl, benzyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) _1-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen may contain, wherein oxygen atoms may not be adjacent;

Very particular preference is given to compounds of the formula (I) in which one or more of the symbols has one of the very particularly preferred meanings given below,

R ¹ and R ² have the above-mentioned particularly preferred meanings; R ³ is (C ₁ -C ₆ ) -alkyl, (C ₂ -6) -alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₃ -C ₈ ) -cycloalkyl, wherein R ^{3 is} unsubstituted or substituted by one or more fluorine or Chloratόme and / or alkyl is substituted,

or

R ³ is 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substituted phenyl or 2,4,6- or 2,4,5-trisubstituted phenyl having substituents selected from the group consisting of fluorine, chlorine, Bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and / or carboxymethyl or

R ³ is pyridyl which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine, cyano, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl , Methoximinomethyl, methoximinoethyl, trifluoromethyl and / or carboxymethyl or

R ³ is pyrimidyl which is linked in the 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, hydroxy, mercapto,

Methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, and / or carboxymethyl; or

R ³ is thienyl, which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl,

Methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, -CH ₃ , -CH (CH ₃ ) ₂ , Cl or cyclopropyl;

X is fluorine, chlorine, (C ₁ -C ₇ ) -alkyl or (C ₁ -C ₃ ) -haloalkyl;

R ⁶ is H, Na, K, NH ₄ , HN (Et) ₂ , H ₂ N (iPr) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, in whole or in part by F and / or Cl and / or carboxy (Ci-C ₄₎ alkyl, CONR ⁶ R ^7, CONR ⁷ oR ^7, COOR ⁸ substituted (C _r C ₈₎ alkyl, (C ₃ -C ₆₎ -alkenyl, propargyl, ( C ₃ -C ₈ ) cycloalkyl, benzyl;

R ⁷ is COR ⁸ , S (O) i _-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , where R ^{8 may be the} same or different, 1-H-pyrrolyl, 1-H-imidazolyl , 1,3,4-oxadiazolyl, 1-H-pyrazolyl, Isoxazolyl, oxazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl, 1-H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2,4] - Oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group Ci-C ₄ - Alkyl and halogen.

R ⁸ is independently H, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, t-butyl, pentyl, hexyl, (C ₁ -C 3) -haloalkyl, (C ₂ -C ₆ ) Alkenyl, propargyl, (C ₃ -C ₆ ) -cycloalkyl, benzyl;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) i. ₂ group to which they are attached, a 4-8 membered cycle containing one or more heteroatoms from the series sulfur,

May contain oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent;

Very particular preference is furthermore given to compounds of the formula (I) in which one or more of the symbols has one of the very particularly preferred meanings given below,

R ¹ and R ² have the above-mentioned particularly preferred meanings;

R- * is 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substituted phenyl or 2,4,6- or

2,4,5-trisubstituted phenyl with substituents selected from the group consisting of fluorine, chlorine, bromine, cyano,

Nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and / or

Carboxymethyl or

R ² is thienyl, which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;

R ⁴ is CONR ⁶ R ⁷ ;

X is fluorine, chlorine, methyl or trifluoromethyl;

R ⁵ is H, -CH ₃ ; R ⁶ is H, Na, K, NH ₄ , HN (Et) ₂ , H ₂ N (iPr) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, in whole or in part by F and / or Cl and / or carboxyKQ-C ^ alkyl, CONR ⁶ R ⁷ , CONR ⁷ OR ⁷ , COOR ⁸ substituted (C ₁ -Cg) -AlkVl, (C ₃ -C ₆ ) alkenyl, propargyl, (C ₃ -C ₈ ) cycloalkyl, benzyl;

R ⁷ is COR ⁸ , S (O) ₂ R ⁸ , COOR ⁸ , 1-H-pyrrolyl, 1-H-imidazolyl, 1,3,4-oxadiazolyl, 1-H-pyrazolyl, isoxazolyl, oxazolyl, 1.3 , 4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl, 1-H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2,4] oxadiazin-3-yl , Dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, wherein the heterocyclic radicals are optionally substituted by one or more radicals from the group Ci-G _t -alkyl and halogen.

R ⁸ is independently of one another H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, (C ₁ -C 3 -haloalkyl, (C ₂ -C ₆ ) - Alkenyl, propargyl, (C ₃ -C ₆ ) cycloalkyl, benzyl;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) i _-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms from the sulfur,

May contain oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent;

The aforementioned residue definitions can be combined with one another in any desired manner. In addition, individual definitions can be omitted.

Compounds of the formula (I) in which R ^{4 is} CONR ⁶ R ⁷ and X is Cl (formula Ia in Scheme 1) can be prepared, for example, as indicated in Scheme 1 starting from 3-aminopyrazole-4-carboxylic acid esters known in the literature (H) (see eg US-A 3,515,715 and US-A 3,634,391) and malonic esters (Ha), with R ¹ ^ C ₁ -C ₈ -alkyl or aryl, produce:

Scheme 1: Method I

The malonic esters (HA) are known from the literature or can be prepared by processes known from the literature (for example WO 04/006913, WO 04/005876, (R ³ = heterocyclyl), US Pat. No. 6,156,925 (R ³ = substituted phenyl), WO-A 03 / 009687 (R ³ = substituted alkyl), Chem. Ber. 1956, 89, 996 (R ³ = substituted cycloalkyl).

Malonic esters of the formula (IIa) where R ³ = (2-chloro or methyl) thiophen-3-yl (compounds of the formula II b in Scheme Ia) can also be prepared according to the following scheme Ia:

Scheme Ia: Method II

Analogous to the last two steps of the synthesis sequence, 2- (2-chloro-thiophen-3-yl) malonate can also be prepared from (2-chloro-thiophen-3-yl) -acetic acid.

The stepwise reaction of the starting compounds (H) to the amine (V) can be carried out, for example, in analogy to the processes specified in WO 04/000844 and in WO 05/082907. The intermediates π, IV, V, VI and VII and their conversion into each other according to Scheme 1 are already known from WO 05/082 907. The compounds VIH (amines, amides, sulfonamides, carbamates, ureas and amino-substituted heterocycles) used for the further reaction of the acid chlorides (VIT) are known. They are commercially available or can be prepared by known processes familiar to the skilled worker, as described for example in Houben-Weyl, Methods of Organic Chemistry or Adv. Heterocycl. Chem. 1998, 72, 79-116 (and literature cited therein).

New and therefore also the subject of the present invention is the reaction of the acid chlorides VII with the compounds of the formula VIII to give compounds of the formula Ia.

As an alternative to the procedure given in Scheme 1, the compounds in which R ⁴ is CONR ⁶ R ^7, R ⁷ is COR ^8, S (O) i _-2 R ⁸ and Het and X is Cl can be of formula I (compounds of the formula Ia in Scheme 2), by reacting the amides of the formula IX, for example, with halogen compounds of the formula X. The amides of the formula XI thus obtained are then reacted either with halogen compounds XII or with compounds XIII to give the end compounds Ia.

Scheme 2: Method III

for compounds for compounds with R ⁶ = alkyl, alkenyl, with R ⁶ = cation, ammo

Alkynyl, cycloalkyl and ammonium

Cycloalkenyl, aryl and alternative b):

arylalkyl

Alternative a):

The amides of the formula IX, in which R ^{3 is} optionally substituted phenyl, and a process for their preparation are known from WO 05/0056556. Amides of the formula IX in which R ^{3 is} optionally substituted heterocyclyl can be prepared by reacting the known from WO 05/000851 3-cyano-pyrazolopyrimidines analogous to that given in WO 05/0056556 process to the corresponding amides of the formula IX implements. Amides of the formula EX in which R ^{3 is} optionally substituted alkyl, if appropriate substituted alkenyl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl, can be prepared by reacting the known from WO 05/056557 3-cyano-pyrazolopyrimidines analogous to the process described in WO 05/0056556 to the corresponding amides of the formula IX. The halogen compounds of the formula X required for the further reactions (for example acid chlorides, chloroformic acid half esters, sulfonyl chlorides, heterocyclic substituted carboxylic acid chlorides) are known. They are commercially available or can be prepared by methods familiar to the person skilled in the art, as described, for example, in HOUBEN WEYL, Methods of Organic Chemistry. The halogen compounds of the formula Xu required for the further reactions (for example alkyl halides, alkenyl halides, alkynyl halides, cycloalkyl halides, cycloalkenyl halides, aryl halides, aralkyl halides) are likewise known. They are commercially available or can be prepared by methods familiar to the person skilled in the art, as described, for example, in HOUBEN WEYL, Methods of Organic Chemistry. The compounds of the formula Xm required for the further reactions (for example metal hydrides, metal hydroxides, amines, where metal is, for example, alkali metals, alkaline earth metals) are likewise known. They are commercially available or can be prepared by methods familiar to the person skilled in the art, as described, for example, in HOUBEN WEYL, Methods of Organic Chemistry.

New and thus also the subject of the present invention is the stepwise reaction of the amides IX with the halogen compounds of the formula X to give compounds of the formula XI and the further reaction either with halogen compounds of the formula XII or compounds of the formula XHI to give compounds of the formula Ia.

Compounds of the formula (I) in which X is a cyano group (compounds of the formula Ib in Scheme 3) can be prepared, for example, as indicated in Scheme 3, starting from the intermediates (V).

Scheme 3: Procedure IV

base

(COCI) ₂

The reaction of compounds of the formula V with cyanide to give compounds of the formula Va is carried out under standard conditions known from the literature (for example: J. Heterocycl Chem. 1993, 30 (4), 993-5). New and thus also the subject of the present invention is the reaction of the acid chlorides VIIa with compounds of the formula VIII to give compounds of the formula Ib.

Compounds of the formula (I) in which X is an optionally substituted alkyl or phenyl radical (compounds of the formula Ic in Scheme 4) can be prepared as described in Scheme 4 starting from the esters (H) known from the literature (see, for example, US Pat. No. 3,515,715 and US Pat. No. 3,634,391) by reaction with β-ketoesters which are likewise known from the literature or can be prepared by literature methods (see, for example, EP-A 1 002 788) of the formula XIV: Scheme 4: Method V

X ¹ = optionally substituted alkyl, (II) optionally substituted phenyl,

X ¹ ^ OMe (XIV)

R °

(XVI)

, R ^z

H-N.

NaOH

(XVIII)

(COCI) ₂

New and thus also the subject of the present invention is the reaction of the acid chlorides XIX with compounds of the formula VEH to give compounds of the formula Ic.

The synthesis of compounds of the formula (I) in which X represents a mercapto, sulfinyl or sulfonyl group (compounds of the formula Id in Scheme 5) is exemplary in Scheme 5 for compounds with X = S (O) _O-2 -CH ₃ . The cyanoalkenes can be used in analogy to Gompper et al., Chem. Ber. 1962, 95, 2861-70 or Chauhan et al., Tetrahedron 1976, 32, 1779-87.

Scheme 5: Method VI

New and thus also the subject of the present invention is the reaction αer acid chlorides XXIV with compounds of formula VIH to give compounds of formula Id. The synthesis of compounds of the formula (I) in which X represents a hydroxy or an alkoxy group (compounds of the formula Ie in Scheme 6) is given in Scheme 6 by way of example for compounds with X =OH and OCH ₃ .

Scheme 6: Method VII

NaOMe

1N NaOH

XXVII XXVIII

Compounds of formula V (where R = Me) (= compounds of formula XXV, Scheme VII) can be reacted with methoxide (see e.g., Tetrahedron 1996, 52 (5), 1735-46) to form methoxy compounds of formula XXVI. These are converted by literature methods into the corresponding carboxylic acids XXVII. These are then transferred analogously Schemes 1/2 on the corresponding carboxylic acid chlorides in the corresponding amides.

The processes according to the invention for the preparation of the compounds of the formula (I) are preferably carried out using one or more reaction auxiliaries.

Suitable reaction auxiliaries are, if appropriate, the customary inorganic or organic bases or acid acceptors. These include, preferably, alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium , Potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or Calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or propanolate, n, -i, -s or -t-butanolate; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N ₅ N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5- Ethyl 2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3, 0] -non-5-ene (DBN), or 1,8 diazabicyclo [5,4,0] undec-7-ene (DBU).

The methods of the invention are preferably carried out using one or more diluents. Suitable diluents are virtually all inert organic solvents. These include preferably aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or ethyl acetate, nitriles such as Acetonitrile or propionitrile, amides, e.g. Dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, and dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

The reaction temperatures can be varied within a substantial range in the processes according to the invention. In general, one works at temperatures between ^{0 0} C and 25O ⁰ C, preferably at temperatures between 10 ⁰ C and 185 ⁰ C.

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under elevated or reduced pressure.

To carry out the process according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in each case in a larger excess. The work-up is carried out in the erfϊndungsgemäßen processes in each case by conventional methods (see, the preparation examples).

The substances according to the invention have a strong microbicidal action and can be used for combating unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials. Fungicides can be used in crop protection, for example for controlling Plasmodiophorotnycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop protection, for example, to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-enumerated generic terms, are named:

Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora;

Diseases caused by powdery mildews such as e.g. Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;

Diseases caused by causative agents of rust diseases, such as Gymnosporangium species, such as, for example, Gymnosporangium sabinae Hemileia species, such as, for example, Hemileia vastatrix;

Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondita; Uromyces species, such as Uromyces appendiculatus;

Diseases caused by pathogens of the group of Oomycetes, e.g.

Bremia species, such as Bremia lactucae;

Peronospora species such as Peronospora pisi or P. brassicae;

Phytophthora species, such as Phytophthora infestans;

Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or

Pseudoperonospora cubensis;

Pythium species such as Pythium ultimum;

Leaf spot diseases and leaf withering, caused by eg Alternaria species, such as Alternaria solani;

Cercospora species, such as Cercospora beticola;

Cladiosporum species, such as Cladiosporium cucumerinum;

Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);

Colletotrichum species, such as Colletotrichum lindemuthanium;

Cycloconium species such as cycloconium oleaginum;

Diaporthe species, such as Diaporthe citri;

Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as, for example, Gloeosporium laeticolor;

Glomerella species, such as Glomerella cingulata;

Guignardia species, such as Guignardia bidwelli;

Leptosphaeria species, such as Leptosphaeria maculans;

Magnaporthe species, such as Magnaporthe grisea; Mycosphaerella species, such as Mycosphaerelle graminicola;

Phaeosphaeria species, such as Phaeosphaeria nodorum;

Pyrenophorae species, such as, for example, Pyrenophora teres;

Ramularia species, such as Ramularia collo-cygni;

Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii;

Typhula species, such as Typhula incarnata;

Venturia species, such as Venturia inaequalis;

Root and stem diseases caused by e.g. Corticium species, such as Corticium graminearum;

Fusarium species such as Fusarium oxysporum;

Gaeumannomyces species such as Gaeumannomyces graminis;

Rhizoctonia species, such as Rhizoctonia solani;

Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola;

Ear and panicle diseases (including corncob) caused by e.g.

Alternaria species, such as Alternaria spp .;

Aspergillus species, such as Aspergillus flavus;

Cladosporium species such as Cladosporium spp .; Claviceps species, such as Claviceps purpurea;

Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis;

Diseases caused by fire fungi, e.g. Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries; Urocystis species, such as Urocystis occulta; Ustilago species such as Ustilago nuda;

Fruit rot caused by e.g.

Aspergillus species such as Aspergillus flavus;

Botrytis species, such as Botrytis cinerea;

Penicillium species such as Penicillium expansum;

Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species such as Verticilium alboatrum;

Seed and soil rots and wilts, as well as seedling diseases caused by e.g.

Fusarium species such as Fusarium culmorum; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;

Cancers, galls and witches brooms caused by e.g. Nectria species, such as Nectria galligena;

Wilt diseases caused by e.g. Monilinia species such as Monilinia laxa;

Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, such as Taphrina deformans;

Degenerative diseases of woody plants, caused for example by Esca species, such as Phaemoniella clamydospora; Floral and seed diseases caused by, for example, Botrytis species such as Botrytis cinerea;

Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani;

Preferably, the following diseases of soybean beans can be controlled:

Fungal diseases on leaves, stems, pods and seeds caused by e.g.

Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)) , Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Powdery Mildew (Phyllosticta sojaecola) Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola )

Fungal diseases on roots and stem base caused by e.g.

Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).

The active compounds according to the invention also have a very good tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.

In the present context, plant-strengthening (resistance-inducing) substances are to be understood as meaning substances which are capable of enhancing the defense system of plants stimulate that the treated plants unfold in subsequent inoculation with unwanted microorganisms extensive resistance to these microorganisms.

Undesirable microorganisms in the present case are phytopathogenic fungi and bacteria. The substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the mentioned pathogens. The period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.

The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.

In this case, the active compounds according to the invention can be used with particularly good success for combating cereal diseases, such as, for example, against Erysiphe species, diseases in the cultivation of wine, fruit and vegetables, for example against Botrytis, Venturia, Sphaerotheca and Podosphaera species ,

The active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.

If appropriate, the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety protection rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.

In the protection of materials, the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.

Technical materials as used herein mean non-living materials that have been prepared for use in the art. For example, technical materials to be protected from microbial change or destruction by the active compounds of the invention may be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, coolants, and other materials that may be infested or degraded by microorganisms , In the context of the materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms. In the context of the present invention, technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.

As microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned. The active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

There may be mentioned, for example, microorganisms of the following genera:

Alternaria such as Alternaria tenuis, Aspergillus such as Aspergillus niger, Chaetomium such as Chaetomium globosum, Coniophora such as Coniophora puetana, Lentinus such as Lentinus tigrinus, Penicillium such as Penicillium glaueum, Polyporus such as Polyporus versicolor, Aureobasidium such as Aureobasidium pullulans, Sclerophoma such as Sclerophoma pityophila, Trichoderma such as Trichoderma viride, Escherichia such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.

Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, superfine encapsulations in polymeric substances and in seed coating compositions, as well as ULV KaIt and warm mist formulations.

These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryl sulfosulfonates. nate and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powders, granules or latexes such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids may be used in the formulations. Other additives may be mineral and vegetable oils.

Dyes, such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue, and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance. In many cases synergistic effects, i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.

As mixing partners, for example, the following compounds are suitable:

fungicides:

/. Inhibition of nuclease acid synthesis

Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl-M, ofurace, oxadixyl, oxolinic acid

2. Inhibition of mitosis and cell division

Benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide

3. Inhibition of the respiratory chain

3.1 complex I diflumetorim

3.2 Complex II

Boscalid, Carboxin, Fenfuram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide

3.3 Complex III

Azoxystrobin, Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Picoxystrobin, Trifloxystrobin

3.4 decoupler

Dinocap, fluazinam

3.5 Inhibition of ATP production

Fentin acetate, fentin chloride, fentin hydroxide, silthiofam

4. Inhibition of amino acid and protein biosynthesis

Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil

5. Inhibition of signal transduction

Fenpiclonil, fludioxonil, quinoxyfen

6. Inhibition of fat and membrane synthesis

Chlozolinate, iprodione, procymidone, vinclozolin

Pyrazophos, Edifenphos, Iprobenfos (TBP), isoprothiolane

Tolclofos-methyl, biphenyl

Iodocarb, Propamocarb, Propamocarb hydrochloride 7. Inhibition of ergosterol biosynthesis

fenhexamid,

Azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Lnazalil, Imazalilsulfate, Oxpoconazole, Fenarimol, Flurprimidol, Nuarimol, Pyrifenox, Triforin, Pefurazoate, Prochloraz, Triflumizol, Viniconazole,

Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, spiroxamine,

Naftifm, pyributicarb, terbinafine

S. Inhibition of cell wall synthesis

Benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A

9. Inhibition of melanin biosynthesis

Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole

10. resistance induction

Acibenzolar-S-methyl, probenazole, tiadinil

11. Multisite.

Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and bordeaux mixture, dichlofluanid, dithianon, dodin, dodine free base, ferbam, fluorofolpet, folpet, fosetyl-al, guazatine, guazatin acetate, Lininoctadin, aminoacidinalbesilat, aminoacidtriacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram 12. Unknown

Amibromdole, benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone; Flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, methasulfocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiine, pentachlorophenol and salts, 2- Phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrroline nitrate, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4-chloro 2-nitrophenyl) -N-ethyl-4-methyl-benzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1, 1, 3 -trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, cis-1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) -cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4 - [[[[l- [3- (trifluoromethyl ) -phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-l, 2,3-triazol-3-one (185336-79-2), methyl 1- (2,3-dihydro -2,2-dimethyl-LH inden-1-yl) -IH-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2 - [[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] -alpha.- (methoxymethylene) -benzacetate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] -benzacetamide, (2S) -N - [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide, 5-Chloro -7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, 5-chloro-6- (2, 4,6-trifluorophenyl) -N - [(1R) -l, 2,2-trimethylpropyl] [l, 2,4] triazolo [l, 5-a] pyrimidin-7-amine, 5-chloro-N - [(1R) -l, 2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [l, 5-a] pyrimidin-7-amine, N- [l- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinotin, 2-butoxy-6 iodo-3-propyl-benzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-benzoacetamide, ^ (S-) ethyl S ^ jS-TriMeth yl-cyclohexy ^ -S-forrnylamino ^ -hydroxybenzamide, 2 - [[[[l- [3 (1-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha- (methoxyimino ) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5- (trifluoromethyl) -pyridin-2-yl] -ethyl} -2- (trifluoromethyl) -benzamide, N-CS''-dichloro -S-fluorobiphenyl ^ -YO-S-cydifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide, 1 - [(4-methoxyphenoxy ) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, O- [1- [(4-methoxyphenoxy) methyl] -dimethylpropyl-1H-imidazole-1-carbothioicacid, 2- (2- {[6- (3-Chloro-2-methylphenoxy) r5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide

bactericides: Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

1. Acetylcholinesterase (AChE) inhibitors

1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carboofuran, carbosulfane, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, Fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)

1.2 organophosphates (eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophosethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chloroformes, chlorpyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenethione, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothione, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos , Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidone, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propet amphos, prothiofos, prothoates, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion) 2. Sodium Channel Modulators / Voltage-Dependent Sodium Channel Blockers

2.1 Pyrethroids (eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrh, biotethrin, bioallethrin-S-cyclopentylisomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis -Resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin , Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (cis-, trans-), Phenothrin (IR-trans isomer), Prallethrin, Profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum))

2.2 Oxadiazines (e.g., indoxacarb)

3. Acetylcholine receptor agonist / antagonists

3.1 chloronicotinyls / neonicotinoids (e.g., acetamiprid, clothianidin, dinotefiran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam)

3.2 Nicotine, Bensultap, Cartap

4. Acetylcholine receptor modulators

4.1 Spinosyns (e.g., spinosad)

5. GABA-driven chloride channel antagonists

5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor

5.2 Fiproles (e.g., acetoprole, ethiprole, fipronil, vaniliprole)

6. Chloride Channel Activators

6.1 Mectins (for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin)

7. Juvenile hormone mimetics

(eg, Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) S. ecdysonagonists / disruptors

8.1 diacylhydrazines (e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides)

9. Inhibitors of chitin biosynthesis

9.1 Benzoylureas (e.g., bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron,

triflumuron)

9.2 Buprofezin

9.3 Cyromazine

10. Inhibitors of oxidative phosphorylation, ATP disruptors

10.1 Diafenthiuron

10.2 Organotin (e.g., azocyclotin, cyhexatin, fenbutatin oxides)

11. Decoupling of oxidative phosphorylation by interruption of the H proton gradient

11.1 Pyrroles (e.g., chlorfenapyr)

11.2 Dinitrophenols (e.g., binapacyrl, dinobutone, dinocap, DNOC)

12. Site I electron transport inhibitors

12.1 METI's (e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)

12.2 Hydramethylnone

12.3 Dicofol

13. Site II Electron Transport Inhibitors

13.1 Rotenone

14. Site III Electron ^Transport Inhibitors

14.1 Acequinocyl, Fluacrypyrim 15. Microbial disruptors of insect intestinal membrane

Bacillus thuringiensis strains

16. Inhibitors of fat synthesis

16.1 Tetronic acids (e.g., spirodiclofen, spiromesifen)

16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] -dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl-ethyl-ester (CAS Reg. No .: 203313-25- 1)]

17. Carboxamides

(e.g., flonicamide)

18. Octopaminergic agonists

(e.g., Amitraz)

19. Inhibitors of magnesium-stimulated ATPase

(e.g., propargite)

20. phthalamides

(eg N ² - [l, l -dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N ¹ - [2-methyl-4- [l, 2,2,2-tetrafluoro-1-one

(trifluoromethyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7), fluorene diamides)

21. Nereistoxin Analogs

(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)

22. Biologics, hormones or pheromones

(eg, azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.) 23. Active substances with unknown or non-specific mechanisms of action

23.1 fumigants (e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides)

23.2 Selective feeding inhibitors (e.g., cryolites, flonicamid, pymetrozines)

23.3 mite growth inhibitors (e.g., clofentezine, etoxazole, hexythiazox)

23.4 Amidoflumet, Benclothiazole, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, quinomethionate, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flotenzin, Gossyplure, Hydmethylnone, Japonilure, Metoxadiazone , Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramide, Tetradifon, Tetrasul, Triarathene, Verbutin,

furthermore, the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2. l] octane-3-carbonitrile (CAS Reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (see WO 96/37494 , WO 98/25923), as well as preparations containing insecticidal plant extracts, nematodes, fungi or viruses.

A mixture with other known active substances, such as herbicides, or with fertilizers and growth regulators, safeners or semiochemicals is possible.

In addition, the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. The application is carried out in a conventional manner, for example by casting, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or the active ingredient preparation or the active ingredient itself in the Inject soil. It can also be the seed of the plants to be treated. When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the mode of administration. In the treatment of parts of plants, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects., For example, reduced amounts of application and / or extensions of the spectrum of action and / or or enhancing the effect of the materials and agents useful in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, received genetic material which gives these plants particularly advantageous valuable intrinsic properties. Examples of such traits include better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher yields Quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soya, potato, cotton, tobacco, rapeseed as well as fruit plants (with the fruits apples, pears , Zitru and maize, soya, potato, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryΙA (b), CryΙA (c), CryllA, CryiπA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb, and CrylF, and combinations thereof) in the plants (hereinafter "Bt plants"). Traits also become particularly emphasized is the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (eg "PAT" gene) .The genes conferring the desired properties ("traits") may also occur in combinations with each other in the transgenic plants. Examples of "Bt plants" include maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YDELD GARD® (eg corn, cotton, soya), KnockOut® (eg corn), StarLink® (eg maize), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed); IMI® (tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to the market developed in the future or in the future coming plant varieties with these or future developed genetic traits.

The listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active substance mixtures according to the invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.

Furthermore, the compounds of the formula (I) according to the invention are suitable for suppressing the growth of tumor cells in humans and mammals. This is based on an interaction of the compounds of the invention with tubulin and microtubules and by promoting microtubule polymerization.

Microtubules play a key role in regulating the structure, metabolism, and division of cells. Inside the cells, tubulin is polymerized in microtubules that form the mitotic spindle. The microtubules are depolymerized when the purpose of the mitotic spindle has been fulfilled. Agents that disrupt the polymerization or depolymerization of microtubules in neoplastic cells, thereby inhibiting the proliferation of these cells, are among the most effective chemotherapeutic cancer agents currently available. The best known examples are the discodermolides and epothilones (Nicolaou et al., Angew Chem. 1998, 110, 2120-2153) and paclitaxel (Taxol).

For this purpose, an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.

Compounds of formula (I) can be used for the treatment of a variety of cancers and other proliferative diseases. Examples of such diseases are:

Carcinomas, including bladder, breast, colon, kidney, liver, lung, ovarian, pancreatic, gastric, cervical, thyroid and skin cancers, including squamous cell carcinomas;

Hematopoietic tumors of the lymphoid cell line, including leukemias, acute lymphocytic leukemias, acute lymphoblastic leukemias, B-cell lymphomas, T-cell lymphomas, Hodgkin's lymphomas, non-Hodgkin's lymphomas, hairy cell lymphomas, and Burke's lymphomas;

Hematopoietic tumors of the myeloid cell line, including acute and chronic myelogenous leukemias and promyelocytic leukemias; Tumors of mesenchymal origin, including fibrosarcomas and rhabdomyosarcomas;

Tumors of the central and peripheral nervous system, including astrocytomas, neuroblastomas, gliomas and schwannomas;

Tumors of mesenchymal origin, including fibrosarcomas, rhabdomyosarcomas and osteosarcomas; and

Other tumors, including melanomas, seminomas, teratocarcinomas, neuroblastomas, gliomas, xenoderma pigmentosum, keratoctanthomas, and follicular thyroid carcinomas.

The effective amount of a compound of formula I can be determined by one of ordinary skill in the art and includes exemplary dosage levels for a human of about 0.05 to 200 mg / kg / day given in a single dose or in the form of single divided doses such as 1 to 4 times a day, can be administered. Preferably, the compounds are administered at a dosage of less than 100 mg / kg / day, in a single dose or in 2 to 4 divided doses. It will be appreciated that the specific dose and frequency of dosing may be varied for a particular patient and will depend on a variety of factors including the effectiveness of the specific compound used, the metabolic stability and the length of action of that compound, the species, the age, body weight, general health status, sex and diet of the patient, the type and time of administration, the rate of excretion, the drug combination and the severity of the particular condition.

Thus, the present invention provides a human medicament comprising at least one compound of formula (I) capable of treating cancer or other proliferative diseases in an amount effective therefor and a pharmaceutically acceptable carrier or diluent. The compositions of the invention may contain other therapeutic agents as described below, and may be prepared, for example, using conventional solid or liquid carriers or diluents, such as pharmaceutical additives of a type suitable for the desired administration (for example, excipients, binders, preservatives, stabilizers, Flavoring agents, etc.) according to techniques well known in the pharmaceutical pharmaceutical field or as required by accepted pharmaceutical practice.

The compounds of formula I may be prepared by any suitable means, for example orally, such as in the form of tablets, capsules, granules or powders, sublingual, buccal, parenteral, such as by subcutaneous, intravenous, intramuscular or intrasternal injection or infusion techniques (eg as sterile, injectable, aqueous or non-aqueous solutions or suspensions), nasally, such as by inhalation spray; topically, as in the form of a cream or ointment, or rectally, such as in the form of suppositories, in dosage unit formulations containing nontoxic pharmaceutically acceptable carriers or diluents. For example, the compounds of formula I may be administered in a form suitable for immediate release or prolonged release. Immediate release or sustained release may be achieved by the use of appropriate drugs containing the compounds of formula I, or more particularly in the case of prolonged release by the use of devices such as subcutaneous implants or osmotic pumps. The compounds of the formula I can also be administered liposomally. For example, the active ingredient may be used in a composition such as a tablet, capsule, solution or suspension containing from about 5 to about 500 mg per unit dosage of a compound or mixture of compounds of the formula or in a topical form (0.01 to 5 wt % Compound of formula I, one to five treatments per day). It may be mixed conventionally with a physiologically acceptable carrier, excipient, excipient, preservative, stabilizer, flavoring agent, etc., or with a topical carrier. The compounds of formula I may also be formulated in compositions such as sterile solutions or suspensions for parenteral administration. About 0.1 to 500 mg of a compound of formula I may be mixed with a physiologically acceptable carrier, excipients, excipients, preservative, stabilizer, etc. in a unit dosage form as required by the accepted pharmaceutical practice. The amount of the active substance in these compositions or preparations is preferably such that a suitable dosage is obtained in the stated range.

Exemplary compositions for oral administration include suspensions containing, for example, microcrystalline cellulose to provide bulk, alginic acid or sodium alginate as a suspending agent, methyl cellulose as a viscosity enhancer and sweetening or flavoring agents such as those known in the art, and tablets containing immediate release, which may include, for example, microcrystalline cellulose, dicalcium phosphate, starch, magnesium stearate and / or lactose and / or other excipients, binders, extenders, disintegrating agents, diluents and lubricants, such as those known in the art. Shaped tablets, compressed tablets or freeze-dried tablets are exemplary forms that can be used. Exemplary compositions include those that formulate compounds of Formula I with fast-dissolving solvents such as mannitol, lactose, sucrose, and / or cyclodextrins. In such formulations can also Contain high molecular weight excipients such as celluloses (Avicel) or polyethylene glycols (PEG). Such formulations may also contain excipients to aid mucosal adhesion such as hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC), sodium carboxymethylcellulose (SCMC), maleic anhydride copolymer (eg Gantrez) and release control agents such as polyacrylic copolymer (eg Carbopol 934 ), contain. Lubricants, lubricants, flavorants, colorants and stabilizers may also be added for ease of manufacture and use.

Exemplary compositions for nasal aerosol and inhalation administration include solutions in physiological saline containing, for example, benzyl alcohol or other suitable preservatives, absorption enhancers to enhance bioavailability and / or other solubilizers or dispersants such as those known in the art.

Exemplary compositions for parenteral administration include injectable solutions or suspensions containing, for example, suitable non-toxic, parenterally-acceptable diluents or solvents such as cremophor, mannitol, 1,3-butanediol, water, Ringer's solution, an isotonic sodium chloride solution, or other suitable dispersion; or wetting and suspending agents, including synthetic mono- or diglycerides, and fatty acids, including oleic acid.

Exemplary compositions for rectal administration include suppositories which may contain, for example, a suitable non-irritating excipient such as cocoa butter, synthetic glyceride esters, or polyethylene glycols which are solid at normal temperature but liquefy and / or dissolve in the rectal cavity to release the drug.

Exemplary compositions for topical administration include a topical carrier such as Piastibase (mineral oil gelled with polyethylene). For example, the compounds of formula I can be administered topically to treat the psoriatic plaques and, as such, can be formulated as a cream or ointment.

The compounds of formula I may be administered either alone or in combination with other anti-cancer and cytotoxic agents and treatments useful in the treatment of cancer or other proliferative diseases. Particularly useful are anticancer and cytotoxic drug combinations in which the second selected drug acts in different manners or at a different phase of the cell cycle, eg S-phase, than the present compounds of formula I, which exert their effects in the G2-M Exercise phase. Examples of classes of anticancer and cytotoxic agents include alkylation. such as nitrogen mustard, alkyl sulfonates, nitrosoureas, ethyleneimines and triazenes; Antimetabolites such as folate antagonists, purine analogs and pyrimidine analogs; Antibiotics such as anthracyclines, bleomycins, mitomycin, dactinomycin and plicamycin; Enzymes, such as L-asparaginase; Farnesyl protein transferase inhibitor; hormonal agents such as glucocorticoids, estrogens / anti-estrogens, androgens / antiandrogens, progestins and luteinizing hormone releasing hormone antagonists, octreotide acetate; Microtubule-destroying agents such as ectein ascidines or their analogs and derivatives; microtubule stabilizing agents such as paclitaxel (Taxol), docetaxel (Taxotere) and epothilone AF or their analogs or derivatives; plant-derived products such as vinca alkaloids, epipodophyllotoxins, taxanes; and topoisomerase inhibitors; Prenyl-protein transferase inhibitors; and various agents such as hydroxyurea, procarbazine, mitotane, hexamethylmelamine, platinum coordination complexes such as cisplatin and carboplatin; and other agents used as anticancer and cytotoxic agents, such as biological response modifiers, growth factors, immunomodulators, and monoclonal antibodies. The compounds of the formula I can also be used together with radiation therapy.

Representative examples of these classes of anticancer and cytotoxic

Agents include, mechlorethamine hydrochloride, cyclophosphamide, chlorambucil, melphalan, ifosfamide, busulfan, carmustine, lomustine, semustine, streptozocin, thiotepa, dacarbazine, methotrexate, thioguanine, mercaptopurine, fludarabine, pentastatin, cladribine, cytarabine, fluorouracil, doxorubicin hydrochloride, daunorubicin , Idarubicin, bleomycin sulfate, mitomycin C, actinomycin D, safracine, saframycin, quinocarcine, discodermolide, vincristine, vinblastine, vinorelbine tartrate, etoposide, teniposide, paclitaxel, tamoxifen, estramustine, estramustine phosphate sodium, flutamide, buserelin, leuprolide, pteridine, diynese, levamisole , Aflacone, interferon, interleukins, aldesleukin, filgrastim, sargramostim, rituximab, BCG, tretinoin, irinotecan hydrochloride, betamethosone, gemcitabine hydrochloride, altretamine and topoteca and all analogs or derivatives thereof.

Preferred members of these classes include paclitaxel, cisplatin, carboplatin, doxorubicin, carminomycin, daunorubicin, aminopterin, methotrexate, methopterine, mitomycin C, ecteinascidin 743, porfiromycin, 5-fluorouracil, mercaptopurine, gemcitabine, cytosine arabinoside, podophyllotoxin or podophyllotoxin derivatives such as Etoposide, etoposide phosphate or teniposide, melphalan, vinblastine, vincristine, leurosidine, vindesine and leuosine.

The combinations of the present invention may also be formulated or co-administered with other therapeutic agents which, because of their particular utility in administering therapies associated with the above-noted conditions, to be selected. For example, the compounds of formula I can be formulated with agents to prevent nausea, hypersensitivity and gastric irritation, such as antiemetics and Hl and H2 antihistamines.

The therapeutic agents indicated above, when used in combination with the compounds of formula I, may be used in the amounts specified in the Physicians' Desk Reference (PDR) or otherwise determined by one of ordinary skill in the art.

New and thus also the subject of the present invention is the use of compounds of the formula I as medicaments.

A further object of the present invention is the use of compounds of the formula I for the production of medicaments, in particular medicines for the treatment of cancer.

The preparation and the use of the active compounds according to the invention are evident from the following examples.

Examples

Example I iV- [5-Chloro-6- (2,4-dichlorophenyl) -7-isopropylamino-pyrazolo [l, 5-α] pyrimidine-3-carbonyl] -methanesulfonamide

To a solution of 1 g of 5-chloro-6- (2,4-dichlorophenyl) -7-isopropylamino-pyrazolo [l, 5-α] pyrimidine-3-carboxylic acid in 20 mL dichloromethane were added 0.95 g of oxalyl chloride and added a drop of dimethylformamide and the mixture stirred until the evolution of gas. It was then concentrated, taken up again with dichloroethane (5 ml). To the resulting solution was added dropwise a solution of 126 mg of methanesulfonic acid amide in 1 ml of pyridine. After further stirring at room temperature under TLC control was quenched with 1N hydrochloric acid, concentrated and the residue chromatographically with R-hexane / ethyl acetate 5: 1 -> 3: 1 purified. This gave 0.029 g of N- [5-chloro-6- (2,4-dichloro-phenyl) -7-isopropylamino-pyrazolo [l, 5-α] pyrimidine-3-carbonyl] -methanesulfonamide (5% of theory).

logP *: 3.96

Analogous to the previously mentioned methods are or were also in the following

Table 1 listed compounds of formula (I-a).

Table 1

The determination of the logP values was carried out according to EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).

** The determination of these logP values was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous formic acid). Preparation of the starting materials:

198 g (1998 mmol) of methyl cyanoacetate, 296 g (1998 mmol) of triethyl orthoformate and 440 g (4310 mmol) of acetic anhydride were heated to reflux in an apparatus with Vigreux column. Volatiles were distilled off until a head temperature of 120 ⁰ C was reached. After cooling, it was fractionated in vacuo. This gave 5 g of methyl (2E / Z) -2-cyano-3-ethoxyacrylate (fraction 1: 65 - 100 ^0C ₅ 0.2 mbar, 88% GCMS purity) and further 209 g of methyl (2E / Z) - 2-cyano-3-ethoxyacrylate (fraction 2: 105-108 ⁰ C, 0.2 mbar,> 99% GCMS purity).

100 g (645 mmol) of methyl (2E / Z) -2-cyano-3-ethoxyacrylate were initially charged in 481 ml of ethanol. Subsequently, 31 ml (645 mmol) of an 85% hydrazine hydrate solution were added dropwise within 45 minutes while cooling (exothermic reaction!) At room temperature. It was further stirred at 75 ° C for 12 hours. It was filtered hot and the organic phase was concentrated under reduced pressure. 64 g of methyl 5-amino-1H-pyrazole-4-carboxylate (logPs = -0.07, HPLC content: 86%) were obtained.

6- (2,4-dichlorophenyl) -5,7-dihydroxy-pyrazolo [l, 5-a] pyrimidine-3-carboxylic acid methyl ester

5.5 g of 2- (2,4-dichlorophenyl) -malonic acid dimethyl ester and 2.8 g of methyl 3-aminopyrazole-4-carboxylate were mixed with 4 g of tri-n-butylamine and stirred at 185 ^° C. for 3 hours; the liberated methanol was distilled off. It was then cooled and the excess trihydrate n-butylamine removed in vacuo. The product obtained was reacted crude without further purification.

logP *: 1.21

5,7-dichloro-6- (2,4-dichlorophenyl) -pyrazolo [l, 5-a] pyrimidine-3-carboxylic acid methylester

10 g of 6- (2,4-dichlorophenyl) -5,7-dihydroxy-pyrazolo [l, 5-a] pyrimidine-3-carboxylic acid methyl ester

were dissolved in 43.3 g of phosphoryl chloride and stirred at 120 ⁰ C for 3 - 4 hours until the end of gas evolution. Thereafter, 2.94 g of phosphorus pentachloride were added and stirred at 120 ⁰ C for 2 - 3 h. After the subsequent cooling, the mixture was concentrated on a rotary evaporator and taken up in water and dichloromethane. The organic phase was separated, dried with sodium sulfate and the solvent removed in vacuo. The residue was purified by chromatography (silica gel, cyclohexane / ethyl acetate 9: 1, 5: 1, 3: 1). The title compound was obtained.

logP *: 3.86

5-Chloro-6- (2,4-dichlorophenyl) -7-isopropylamino-pyrazolo [l, 5-a] pyrimidine-3-carboxylic acid methyl ester

5 g of the dichloro compound previously obtained were dissolved in 50 ml of acetonitrile and 0.831 g

Isopropylamine added. Under ice-cooling, 2.651 g of potassium carbonate was added and the mixture was stirred at room temperature for 15 h (TLC check). It was then neutralized with 1 N hydrochloric acid and filtered with suction. Solid. _^

logP *: 4.07 5-chloro-6- (2,4-dichlorophenyl) -7-isopropyIamino-pyrazolo [l, 5-α] pyrimidine-3-carboxylic acid

5 g of 5-chloro-6- (2,4-dichlorophenyl) -7-isopropylamino-pyrazolo [l, 5-a] pyrimidine-3-carboxylic acid methyl ester were dissolved in 75 mL of 1,4-dioxane and washed with 75 mL 2N potassium hydroxide solution. After stirring at room temperature for 15 h (TLC check), the mixture was introduced into 1 N hydrochloric acid. The precipitated solid was filtered off with suction.

logP *: 3.30

The following intermediates were prepared analogously:

OCH,

2- (3-methyl-thiophen-2-yl) -maIonsäuredimethyIester:

Aluminum trichloride (163 g, 1.222 mol) was initially charged in 540 ml of dichloromethane, the mixture was cooled to 0 ^° C. and, at this temperature, 112 ml (150 g, 1.222 mol) of methyl oxalate chloride were added dropwise. The mixture is then stirred for 10 min at this temperature, then likewise added dropwise at 0 ⁰ C 3-methylthiophene and the reaction mixture was stirred after warming to room temperature overnight at this temperature. The hydrolysis was carried out by discharging to 2 l of ice water, separating off the organic phase, washing with sodium bicarbonate solution and drying of the organic phase over sodium sulfate yielded after filtering off the drying agent and rotary evaporation 119.5 g (3-methyl-thiophen-2-yl) -oxo methyl acetate. Yield: 57%. ¹ H-NMR (DMSO): δ = 8.09 (d, 1H), 7.19 (d, 1H), 7.67 (dd, 1H), 3.90 (s, 3H), 2.49 (s, 3H).

A solution of 90 g (0.489 mol) (3-methyl-thiophen-2-yl) -oxo-acetic acid methyl ester in 260 ml of diethylene glycol was slowly added 112.5 ml (116 g, 2.312 mol) of hydrazine hydrate and the mixture heated to reflux for 30 min , After cooling to 30- 40 ⁰ C were added portionwise 82 g (1.246 mol) of potassium hydroxide, which is accompanied by a temperature increase to 70 - 8O ⁰ C with simultaneous evolution of nitrogen. It was then heated slowly to reflux and stirred for a total of 5 h at this temperature. After cooling to room temperature, the mixture was added to 2 liters of water, adjusted to pH = 1 with 250 ml of half-concentrated hydrochloric acid and extracted with ethyl acetate. Drying of the organic phase over magnesium sulfate, filtering and removal of the solvent afforded 50 g of (3-methyl-thiophen-2-yl) -acetic acid. Yield: 66%. ¹ H NMR (DMSO): δ = 7.25 (d, 1H), 6.84 (d, 2H), 3.67 (s, 2H), 2.11 (s, 3H).

A solution of 50 g (0.32 mol) of (3-methyl-thiophen-2-yl) -acetic acid in 500 ml of methanol was treated with 5 ml of conc. Sulfuric acid and heated to reflux for 8 h. Subsequently, the The solvent is evaporated off and the residue is combined with water and dichloromethane. Phase separation and renewed extraction of the aqueous phase with dichloromethane yielded after drying the organic phase over sodium sulfate, filtering and rotary evaporation 42.5 g (3-methyl-thiophen-2-yl) -acetic acid methyl ester. Yield: 70%. ¹ H NMR (DMSO): δ = 7.30 (d, 1H), 6.87 (d, 1H), 3.82 (s, 2H), 3.65 (s, 3H), 2.13 (s, 3H).

Under argon, 311 ml (332 g, 3.685 mol) of dimethyl carbonate with 14.7 g of sodium hydride (60% in mineral oil) were added and heated to 8O ⁰ C. A solution of 41 g (0.217 mol) of methyl (3-methyl-thiophen-2-yl) acetate in 50 ml of toluene was slowly added dropwise at this temperature and the mixture stirred overnight at reflux. For work-up, the mixture was diluted with about 200 ml of methanol, the mixture was added to ice-water and acidified with dilute hydrochloric acid. Extraction with dichloromethane, drying of the organic phase over sodium sulfate, filtering and removal of the solvent afforded 43.6 g of 2- (3-methyl-thiophen-2-yl) -malonsäuredimethylester. Yield: 88%. ¹ H NMR (DMSO): δ = 7.42 (d, 1H) ₃ 6.89 (d, 1H), 5.27 (s, 1H), 3.69 (s, 6H), 2.15 (s, 3H).

Spectroscopic data of the analogously prepared intermediates:

use Examples

Example A

Podosphaera test (apple) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 ⁰ C and a relative humidity of about 70%.

10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

In this test, the compounds according to the invention of the following example numbers showed an efficacy of 70% or more at a concentration of active ingredient of 100 ppm.

9, 15, 33, 38, 39, 45, 117, 123, 171, 183, 189, 207, 261, 285, 357, 441, 465, 519, 543, 549

Example B

Venturia - test (apple) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab Venturia inaequalis and then remain for 1 day at about 2O ⁰ C and 100% relative humidity in an incubation cabin.

The plants are then placed in the greenhouse at about 21 ⁰ C and a relative humidity of about 90%.

10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

In this test, the compounds according to the invention of the following Example Nos. Showed an efficacy of 70% or more at an active ingredient concentration of 100 ppm.

3, 9, 14, 15, 21, 33, 38, 39, 45, 117, 123, 171, 177, 183, 189, 201, 207, 213, 255, 261, 285, 345, 351, 357, 381, 435, 441, 459, 465, 507, 513, 519, 525, 543, 549, 1178 Example C

Botrytis - test (bean) / protective

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at about 2O ⁰ C and 100% relative humidity.

2 days after the inoculation, the size of the infestation spots on the leaves is evaluated. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

In this test, the compounds according to the invention of the following example numbers showed an efficacy of 70% or more at a concentration of active ingredient of 100 ppm.

3, 9, 14, 15, 21, 33, 38, 39, 45, 117, 123, 171, 177, 183, 189, 201, 207, 213, 255, 261, 285, 345, 351, 357, 381, 435, 441, 459, 465, 507, 513, 519, 525, 543, 549, 1178

Example D

Sphaerotheca test (cucumber) / protective

Solvent: 49 parts by weight of N, N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young cucumber plants are sprayed with the preparation of active compound in the stated application rate. One day after the treatment, the plants are inoculated with a spore suspension of Sphaerotheca fuliginea. Subsequently, the plants are placed in a greenhouse at 70% relative humidity and a temperature of 23 ⁰ C.

7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

In this test, the compounds of the invention of the following formulas show an efficacy of 70% or more at an active ingredient concentration of 500 ppm.

9, 14, 15, 33, 38, 123, 183, 351, 357, 429, 465

Example E

Puccinia test (wheat) / protective

Solvent: 50 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain 48 hours at 20 ⁰ C and 100% relative humidity in an incubation cabin.

The plants are then placed in a greenhouse at a temperature of about 2O ⁰ C and a relative humidity of 80% to promote the development of rust pustules.

10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

In this test, the following compounds according to the invention show an efficacy of 70% or more at an active ingredient concentration of 1000 ppm.

3, 9, 15, 33, 45, 117, 123, 177, 201, 207, 255, 285, 345, 381, 435, 441, 465, 507, 513, 549 Example F

Compounds of this invention were tested for potential cytotoxic or antiproliferative activity on the human tumor cell lines HeLa, SW620 and A375 (all from ATTC, American Type Culture Collection). For this purpose, the cells were plated in microtiter plates from Greiner (manufacturer No. 781092) in a cell density of 1000 cells / microtiter plate well and cultured in cell culture medium at 37 ⁰ C under 5% carbon dioxide atmosphere. The cell culture media and additives were purchased from the company Invitrogen, the fetal calf serum from the company. Biochrom. The cell culture media for Heia and A375 cells were used as indicated at ATCC (HeLa: MEM, Order No. 10370-047, with 1% sodium bicarbonate, 1% nonessential amino acids, 1% sodium pyruvate, 10% fetal calf serum, 0.1% gentamycin; A375: DMEM, order no. 41965-039, 2% sodium bicarbonate, 1% L-glutamax, 10% fetal calf serum, 0.1% gentamycin). The culture medium for the SW620 cells consisted of DMEM, order no. 41965-039, 1% nonessential amino acids, 10% fetal calf serum, 0.1% gentamycin.

Twenty-four hours after plating out the cells in microtiter plates, the test compounds were added to the cells at various concentrations of a maximum of 100 μM to a minimum concentration of 5 nM. Stock solutions of the test compounds (10 mM) were prepared in DMSO and stored at -2O ⁰ C. For the cytotoxicity assays, the test compounds were diluted in the appropriate cell culture medium.

After a further 48 hours incubation time, the cells were washed with medium and analyzed by the manufacturer according to a two-color fluorescence cytotoxicity / viability test (LIVE / DEAD Viability / Cytotoxicity ASSAY Kit from Molecular Probes, order no. L-3224). For this purpose, the medium was aspirated and the cells each 30 .mu.l LIVE / DEAD reagent per microtiter plate well added and incubated for 30 minutes. Subsequently, the cells were washed washed with PBS (phosphate buffered saline). The number of living cells was analyzed by measuring the green fluorescence of the live dye calcein-AM as a component of the LIVE / DEAD reagent on a fluorescence plate measuring instrument (Flexstation, Molecular Devices) at an excitation wavelength of 485nM and an emission wavelength of 525nM (Oral et al 1998). In parallel, cells were carried and analyzed only with cell culture medium without addition of test compounds as growth controls. As reference compounds for anti-tumor agents having a cytotoxic or proliferation-inhibiting action were colchicine (Merck / Calbiochem, Order No. 234115) and taxol (Baccatin HI N-benzyl-b-phenylisoserine ester, Fa. Merck / Calbiochem, Order No. 580555 ) (Schiff and Horwitz 1980, Holmes et al., 1991). The cytotoxic effects of test compounds are expressed as log _GI50 - values (growth (growth-) inhibiting logarithmic concentration value measured at the 50% reduced cell growth when compared to the control without the test compounds; Xia et al, 2001; Smith et al., 2005).

Table 2: Inhibition of cell proliferation in the presence of test compounds according to the protocol of the LIVE / DEAD cytotoxicity assay on various human tumor cell lines, log GI ₅₀ values (M)

Example no.

SW620

A375 cells cells HeLa cells

Colchicine 7.7 7.5 7.8

Taxol 6.7 6.9 7.8

177

8,1 6,7> 8 117

6.6 6.6 6.8 345

6.3 6.4 6.6

As an alternative to analysis of cell growth in microtiter plates, the various cells were also cultured on coverslips and incubated analogously with the test compounds. As described, the cells were treated with the reagents from the LIVE / DEAD Assay Kit according to the manufacturer's instructions and then viewed on a fluorescence microscope.

Claims

claims

1. pyrazolopyrimidines of the formula (I)

in which the symbols have the following meanings:

R ¹ is hydrogen, optionally substituted alkyl, optionally substituted

Alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or optionally substituted heterocyclyl, hydroxy, optionally substituted alkoxy, amino, optionally substituted alkylamino or optionally substituted dialkylamino;

R ² is hydrogen or alkyl;

or

R ¹ and R ² , together with the nitrogen atom to which they are attached, are an optionally substituted heterocyclic ring;

R 3 is optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aralkyl, halogen, an optionally substituted amino group, optionally substituted (C ₁ -C ₆ ) -Aikoxy, optionally substituted (C ₁ -C ₆ ) -alkylthio, optionally substituted (C 9 -C 10) -acyloxy, optionally substituted

(C ₁ -C ₁₀ ) -arylthio, optionally substituted heterocyclyloxy, optionally substituted (C ₆ -C ₁₀ ) -aryl (C ₁ -C ₄ ) -alkoxy, optionally substituted (C ( _j- Cio) -aryl- (C ₁ C ₄ ) -alkylthio, optionally substituted heterocyclyl- (C ₁ -C ₄ ) -alkoxy, optionally substituted heterocyclyl- (C ₁ -C ₄ ) -alkylthio, C (S) OR ⁸ , C (O) SR ⁸ or C ( S) SR ⁸ ;

R ⁴ is CONR ⁶ R ⁷ ; R is H, halogen, optionally halogen-substituted alkyl or optionally halogen-substituted cycloalkyl, O- (C ₁ -C ₄ ) -alkyl or S (Oy ₂ (C ₁ -C ₄ ) -alkyl;

X is halogen, cyano, hydroxy, optionally substituted alkyl, (C ₁ -C ₃ ) haloalkyl, optionally substituted alkoxy, optionally substituted

Phenyl, optionally substituted alkylthio, optionally substituted alkylsulfinyl or optionally substituted alkylsulfonyl;

R ⁶ is H, a cation, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl and optionally substituted cycloalkenyl, optionally substituted aryl and optionally substituted arylalkyl;

R ⁷ is COR ⁸ , S (O) i _-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , saturated, partially or fully unsaturated or aromatic optionally substituted 5- or 6-membered heterocyclyl optionally containing 1 or Contains 2 further N, S or O atoms, oxygen atoms not being allowed to be adjacent;

R ⁸ is H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, aryl or optionally substituted aralkyl, optionally substituted haloalkyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ form together with the N-CO or NS (O) ₁ . ₂ group to which they are attached, a 4-8 membered cycle containing one or more heteroatoms from the

Series may contain sulfur, oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent;

and agrochemically active salts thereof.

2. pyrazolopyrimidines of the formula (I), according to claim 1, in which the symbols have the following meanings R ¹ is hydrogen, alkyl of 1 to 10 carbon atoms which is unsubstituted or monosubstituted, monosubstituted or differently substituted by halogen,

Cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6

Carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or

R 1 is alkenyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or

R ¹ is alkynyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 Carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or

R ¹ is cycloalkyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen and / or alkyl of 1 to 4 carbon atoms, or

R ¹ is saturated or unsaturated heterocyclyl having 3 or 10 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, wherein the

Heterocyclyl unsubstituted or monosubstituted or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano, nitro, cycloalkyl having 3 to 6 carbon atoms, hydroxy, alkoxy having 1 to 4 carbon atoms and / or mercapto;

R ² is hydrogen or alkyl of 1 to 6 carbon atoms;

R ¹ and R ² , together with the nitrogen atom to which they are attached, are a saturated or unsaturated heterocyclic ring containing from 3 to 8 ring members, where the heterocycle optionally contains one further nitrogen, oxygen or sulfur atom as ring member and wherein the heterocycle unsubstituted or substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, hydroxy, alkoxy having 1 to 4 carbon atoms, Haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and / or

Chlorine atoms, mercapto, Thiόalkyl having 1 to 4 carbon atoms and / or

Haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms;

R ³ is C ₁ -C ₁₀ alkyl, C 2 C ₁₀ alkenyl, C 2 -C ₅ alkynyl, Cs-Cg-cycloalkyl, phenyl

Ci-CiQ-alkyl, wherein R ^{3 is} unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^x , or Cj-C ^ o-haloalkyl, optionally one to three radicals from the group R ^x and R ^{x is} cyano, nitro, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₁ -Cg alkoxy, C ₁ -C ₆ haloalkoxy, C C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -haloalkylsulfonyl, C ₁ - C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ alkynyl, C ₃ -C ₈ alkynyloxy and optionally halogenated oxy-C ₁ -C ₄ alkyl-Cj-C4-al- kenoxy, oxy-C ₁ -C ₄ alkenyl-C; [- C4-alkoxy, oxy-C ₁ -C ₄ alkyl-C ₁ -C ₄ alkyloxy , or

R ³ is phenyl, which may be monosubstituted, monosubstituted or differently substituted by one to four times

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;

in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfmyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

Cycloalkyl of 3 to 8 carbon atoms;

2,3-propanediyl linked in the 2,3-position, 1,4-butanediyl, methylenedioxy (-O-CH 2 -)

O-) or 1,2-ethylenedioxy (-O-CH 2 -CH 2 -O-), where these radicals may be mono- or polysubstituted by identical or different substituents by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms;

or

R ² is saturated or wholly or partially unsaturated or aromatic heterocyclyl having 3 to 8 ring members and 1 to 3 heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the heterocyclyl may be monosubstituted or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, Alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms,

Haloalkoxy having 1 to 4 carbon atoms, Haloalkylthio having 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl having 3 to 6 carbon atoms and / or carboxyalkyl

R ³ is C i -Cg -alkylamino, C ₂ -C 3 -alkenylamino, C ₂ -C ₈ -alkynylamino, di-C ₁ -C ₆ -alkylamino, di-C ₂ -C ₈ -alkenylamino, di-C ₂ -C ₈ -alkynylamino, C ₂ -C ₈ -

Alkenyl- (C ₂ -C ₈ ) -alkynylamino, C ₂ -C ₈ -alkynyl- (C ₁ -C ₆ ) -alkylamino, C ₂ -C ₈ -alkenyl- (C ₁ -C ₆ ) -alkylamino, Cg- C \ Q-arylamino, Cg-C \ Q-aryl 1- (C-Cg) -alkylamino, Cg-C \ Q-aryl- (C ₁ -C ₄ ) -alkyl- (C ₁ -C -g) alkylamino, heterocyclyl (C \ -CG) - alkylamino or heterocyclyl (C; _[-C 4) -alkyl- (C ₁ -C ₆₎ alkylamino;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, halogen, unsubstituted or substituted by one or more halogen atoms (C ₁ -C ₄ ) alkyl, unsubstituted or substituted by one or more halogen atoms cyclopropyl; SCH3, SOCH ₃ , SO ₂ CH ₃ or OCH ₃ .

X is H, fluorine, chlorine, bromine, CN, hydroxy, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms; R ⁶ is H, an alkali or alkaline earth metal, copper, NH ₄ , InOnO- (C ₁ -C ₁₀ ) -alkylammonium, di- (C ₁ -C ₁₀ ) -alkylammonium, tri- (C ₁ -C ₁₀ ) -alkylammonium , tetra- (C ₁ -C ₁₀ ) -alkylammonium, where the alkyl radicals of the ammonium ions may be substituted by aryl or hydroxy, cholinium, C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkenyl, aryl,

Phenyl-C ₁ -C ₁₀ -alkyls where R ^{6 is} unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^x , or C ₁ -C ₁₀ -haloalkyl which may optionally have one to three radicals the group R ^x wears, and R ^x is cyano, nitro, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ - cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ - C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -alkynyl, C ₃ - C ₆ -alkynyloxy and optionally halogenated oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkenoxy, oxy-C ₁ -C ₄ -alkenyl-C ₁ -C ₄ -alkoxy, oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkyloxy and / or CONR ⁶ R ⁷ , CONR ⁷ OR ⁷ , COOR ⁸ , carboxy (C ₁ -C ₄ ) -alkyl;

R ⁷ is COR ⁸ , S (O) i. ₂ R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , or

A, B, D, E, G are the same or different CR ⁹ , CR ⁹ R ⁹ , N, NR ⁹ , O or S, with the proviso that at least one symbol is N, O or S, and that

Oxygen atoms are not adjacent;

Y is C, CR ⁹ or N;

R ⁸ is H, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkenyl, aryl, phenyl-C C ₁ -C ₁₀ -alkyl, wherein R ^{8 is} unsubstituted or partially or completely halogenated and / or optionally one to three radicals from the

Carries group R ^x , or C ₁ -C ₁₀ -haloalkyl which optionally carries one to three radicals from the group R ^x , and R ^x cyano, nitro, hydroxy, C ₁ -C ₆ -alkyl, C ₁ -C ₆ - haloalkyl, C ₃ -C ₆ - cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ -haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C _8- alkenyl, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -Al- kinyl, C3-Cg-alkynyloxy and optionally halogenated oxy-Cj-C ^ alkyl-C i -C4-alkenoxy, oxy-C-C4-alkeny 1-C \ -C ^ alkoxy, oxy-C \ -C4-alky 1-C 1 -C 4 -alkyloxy; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) i _-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen may contain, wherein oxygen atoms may not be adjacent;

R ⁹ is R ⁷ , halogen, NR ⁷ ₂ , OH, SR ⁷ or OR ⁷ ;

3. pyrazolopyrimidines of the formula (I), according to one or more of claims 1 to 2, in which the symbols have the following meanings

R ¹ is hydrogen, alkyl of 1 to 10 carbon atoms which is unsubstituted or monosubstituted, monosubstituted or differently substituted by halogen,

Cyano, hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6

Carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino,

Mono- or dialkylamino each having 1 to 4 carbon atoms, or

R ¹ is alkenyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted by identical or different substituents by halogen, cyano,

Hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6

Carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino,

Mono- or dialkylamino each having 1 to 4 carbon atoms, or

R ¹ is alkynyl of 2 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen, cyano,

Hydroxy, alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 4 carbon atoms, amino, mono- or dialkylamino each having 1 to 4 carbon atoms, or

R ¹ is cycloalkyl of 3 to 10 carbon atoms which is unsubstituted or monosubstituted to trisubstituted, identically or differently substituted by halogen and / or

Alkyl of 1 to 4 carbon atoms, or R ¹ is saturated or unsaturated heterocyclyl having 3 to 10 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, wherein the heterocyclyl is unsubstituted or monosubstituted or polysubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano , Nitro, cycloalkyl of 3 to 6 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms and / or

mercapto;

R ² is hydrogen or alkyl of 1 to 6 carbon atoms;

R ¹ and R ² together with the nitrogen atom to which they are attached, a saturated or unsaturated heterocyclic ring having 3 to 8 ring members, wherein the heterocycle optionally another nitrogen, oxygen or

Sulfur atom as a ring member and wherein the heterocycle may be unsubstituted or substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms, hydroxy, alkoxy having 1 to 4 carbon atoms, haloalkoxy having 1 to 4 carbon atoms and 1 to 9 fluorine and / or

Chlorine atoms, mercapto, thioalkyl having 1 to 4 carbon atoms and / or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms;

R ³ is C ₁ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₈ -cycloalkyl, phenyl-C ₁ -C ₁₀ -alkyl, wherein R ^{3 is} unsubstituted or is partially or fully halogenated and / or optionally carries one to three radicals from the group R ^x , or C ₁ -C ₁₀ -haloalkyl which optionally carries one to three radicals from the group R ^x , and R ^x cyano, nitro, hydroxy C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylamino, di- C C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₈ -alkynyl, C ₃ -C ₆ -alkynyloxy and optionally halogenated oxy-C ₁ -C ₄ -alkyl C ₁ -C ₄ -alkenooxy, oxy-C ₁ -C ₄ -alkenyl-C ₁ -C ₄ -alkoxy, oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkyloxy, or

R3 is phenyl which may be monosubstituted, monosubstituted or differently substituted by four Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6

Carbon atoms;

in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl,

Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

Cycloalkyl of 3 to 8 carbon atoms;

1,3-propanediyl, 1,4-butanediyl, methylenedioxy (-O-CH 2 -O-) or 1,2-ethylenedioxy (-O-CH 2 -CH 2 -O-) linked in the 2,3 position, these radicals being mono- or polysubstituted by identical or different substituents by halogen, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 to 4

Carbon atoms and 1 to 9 same or different halogen atoms;

or

R- * is saturated or wholly or partially unsaturated or aromatic heterocyclyl having 3 to 8 ring members and 1 to 3 heteroatoms from the group nitrogen, oxygen and sulfur, wherein the heterocyclyl may be monosubstituted or disubstituted by halogen, alkyl having 1 to 4 carbon atoms , Alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, hydroxy, mercapto, cyano, nitro and / or cycloalkyl of 3 to 6 carbon atoms or / and carboxyalkyl R ³ is C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenylamino, C ₂ -C ₈ -alkynylamino, di-C ₁ -C ₆ -alkylamino, di-C ₂ -C 9 -alkenylamino, Di - Cg- alkynylamino, C ₂ -C 3 -alkenyl- (C ₂ -C ₈ ) -alkynylamino, C ₂ -C ₆ -alkynyl- (C ₁ -C ₈ ) -alkylamino, C ₂ -C ₈ -alkenyl- (C ₁ -C ₈ ) -alkylamino, C ₆ -C _10- arylamino, C ₆ -C ₁₀ -aryl (C ₁ -C ₆ ) -alkylamino, C ₆ -C ₁₀ -aryl (C ₁ -C ₄ ) -alkyl- (C ₁ -C 8) -alkylamino, heterocyclyl- (C ₁ -C 8) alkylamino or heterocyclyl (C ₁ -C ₄ ) -alkyl- (C ₁ -C 8) -alkylamino;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, halogen, unsubstituted or substituted by one or more halogen atoms (C ₁ -C ₄ ) alkyl, unsubstituted or substituted by one or more halogen atoms cyclopropyl; SCH ₃ , SOCH ₃ , SO ₂ CH ₃ or OCH ₃ .

X is H, fluorine, chlorine, bromine, CN, hydroxy, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms or (C ₁ -C 7) -alkyl or (C ₁ -C ₃ ) -haloalkyl;

R6 is H, an alkali or alkaline earth metal, copper, NH _4, mono- (C ₁ -C ₁₀₎ - alkyl ammonium, di- (C ₁ -C ₁₀₎ alkylammonium, tri (C1-C1) 0-alkylammonium, TEFRA - (C ₁ -C ₁₀₎ alkylammonium, the alkyl radicals of the ammonium ions with aryl or hydroxy may be substituted, cholinium, C ₁ -C ₁₀ alkyl, ^C 2- ^C 10 alkenyl, _C2-Cκ) alkynyl, Cs -Cg-cycloalkyl, C ₃ -C ₈ -cycloalkenyl, aryl, phenyl-C ₁ -C ₁₀ -alkyl, where R ^{2 is} unsubstituted or partially or completely halogenated and / or optionally bears one to three radicals from the group R ^x , or C ₁ -C ₁₀ -haloalkyl which optionally bears one to three radicals from the group R ^x , and R ^{x is} cyano, nitro, hydroxy, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₆ -cycloalkyl , Ci-COE-alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ -alkylthio, C i -CG haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -haloalkylsulfonyl, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ alkynyl, C3-Cg-alkynyloxy and optionally halogenated oxy-C ₁ -C ₄ alkyl-C ₁ -C ₄ kenoxy -AL-, oxy-C ₁ -C ₄ alkenyl-C ₁ -C ₄ -alkoxy, oxy-C ₁ -C ₄ -acyl-C ₁ -C ₄ -alkyl, and / or CONR ⁶ R ⁷ , CONR ⁷ OR ⁷ , COOR ⁸ , carboxy (C _r C ₄₎ alkyl;

R ⁷ is COR ⁸ , S (O) _1-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , wherein the radicals R ⁸ may be the same or different, or

A, B, D ₅ E, G are the same or different CR ⁹ , CR ⁹ R ⁹ , N, NR ⁹ , O or S with the proviso that at least one symbol is N, O or S, and that oxygen atoms are not adjacent ;

Y is C, CR ⁹ or N;

R ⁸ is independently H, C _j -Cio alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cg cycloalkyl, C ₃ -C ₈ cycloalkenyl, aryl, phenyl-Ci-C _j o- alkyl, wherein R ^{8 is} unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R ^x , or C _j -Cio-haloalkyl, which optionally carries one to three radicals from the group R ^x , and R ^x cyano,

Nitro, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C3-Cg cycloalkyl, C ₁ -CG -alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, Ci-CSS haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C [-CG-alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkenyloxy, C ₂ -C ₈ -alkynyl, C ₃ -C ₆ -alkinyloxy and optionally halogenated oxy-C _j -C ^ alkyl-Cj-C ^ alkenoxy , Oxy-C ₁ -C ₄ -alkenyl-C ₁ -C ₄ -alkoxy, oxy-C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkyloxy; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) i _-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen may contain, wherein oxygen atoms may not be adjacent;

R ⁹ is R ⁷ , H, halogen, NR ⁷ ₂ , OH, SR ⁷ or OR ⁷ ;

4. pyrazolopyrimidines of the formula (T) according to one or more of claims 1 to 3, in which the symbols have the following meanings

R ¹ is hydrogen or a radical of the formula

or stands,

where # denotes the point of attachment (these radicals may be present both in optically pure form and in isomeric mixtures);

R ² is hydrogen, methyl, ethyl, propyl, or

R ¹ and R ² together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1 (2H) -pyridinyl or tetrahydro-1 (2H) -pyridazinyl, where these radicals are unsubstituted or substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl,

or ! and R ² , together with the nitrogen atom to which they are attached, are a radical of the formula

wherein

R 'is hydrogen or methyl,

R "represents methyl, ethyl, fluorine, chlorine or trifluoromethyl,

m is the numbers 0, 1, 2 or 3, where R "is identical or different radicals, when m is 2 or 3,

R '"represents methyl, ethyl, fluorine, chlorine or trifluoromethyl

and

n is the numbers 0, 1, 2 or 3, where R '"is identical or different radicals, when n is 2 or 3.

R ² is (C- _[ Cg] alkyl, (C3-Cg) cycloalkyl wherein R ^{2 is} unsubstituted or substituted by one or more fluorine or chlorine atoms, benzyl or

R ² is phenyl which may be monosubstituted to trisubstituted by identical or different substituents

Fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, ethynyl, allyl, propargyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl,

Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethinyloxy, trifluoroethinyloxy, chloroallyloxy, iodo-propargyloxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy , Methoxycarbonyl, ethoxycarbonyl,

Hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, Methoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopeniyl or cyclohexyl, or by

2,3-propanediyl linked in the 2,3-position, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), these radicals may be mono- or polysubstituted by identical or different substituents by fluorine,

Chloro, methyl, ethyl, n-propyl, i-propyl trifluoromethyl, carboxy and / or carboxymethyl

R ³ is pyridyl which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine, cyano, hydroxyl, mercapto, nitro, methyl, ethyl, methoxy, methylthio, hydrox - iminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydrox - iminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is thienyl which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydrox - iminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is C ₁ -C ₆ -alkylamino or di-C ₁ -C ₆ -alkylamino, or

R ³ is thiazolyl which is linked in the 2-, 4- or 5-position and may be mono- to disubstituted, identical or different, by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl,

Trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1,2,4-triazolyl, N-pyrrolyl, or N-morpholinyl, each unsubstituted or one or - if possible - several times identical or different with fluorine, chlorine, bromine, cyano,

Nitro * hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximino methyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl are substituted,

R ⁴ is CONR ⁶ R ⁷ ;

R ^{5 is} H, Cl, F, CH ₃ , -CH (CH ₃ ) 2 θ the cyclopropyl; X is H, F, Cl, CN, unsubstituted or substituted by one or more fluorine or chlorine atoms C ₁ -C ₄ alkyl;

R ⁶ is H, Na, K, ₂ Ca, V ₂ Mg, Cu, NH ₄ , NH (CH ₃ ) ₃ , N (CH ₃ ) ₄ , HN (C ₂ Hj) ₃ , N (C ₂ H ₅ ) ₄ , H ₂ N (iC ₃ H ₇ ) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, cholinium, (C _r C ₈ ) alkyl ₅ (C ₃ -C ₆ ) - Alkenyl, (C ₃ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl, phenyl, benzyl;

R ⁷ is COR ⁸ , S (O) _1-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , pyrrolyl, imidazolyl, pyrazolyl,

1,3,4-triazolyl, thiazolyl, isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, oxazolyl, isoxazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2,4] oxadiazine-3 yl, dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group Ci-C ₄ - alkyl, Ci-C ₄ alkoxy, and

Halogen;

R ⁸ is H, (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) -alkenyl, propargyl, (C ₃ -C ₈ ) -cycloalkyl, benzyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally contains 1 or 2 further N, S or O atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) _\ . ₂ to which they are attached, a 4-8 membered cycle which may contain one or more heteroatoms selected from sulfur, oxygen and / or nitrogen, oxygen atoms not being adjacent;

5. pyrazolopyrimidines of the formula (I) according to one or more of claims 1 to 4 wherein the symbols have the following meanings

R ¹ is hydrogen or a radical of the formula

or stands,

where # denotes the point of attachment (these radicals may be present both in optically pure form and in isomeric mixtures);

R ² is hydrogen, methyl, ethyl, propyl, or

R ¹ and R ² together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-1 (2H) -pyridinyl or tetrahydro-1 (2H) -pyridazinyl, where these radicals are unsubstituted or substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl,

or R ¹ and R ² , together with the nitrogen atom to which they are attached, are a radical of the formula

wherein

R 'is hydrogen or methyl,

R "is methyl, ethyl, fluorine, chlorine or trifluoromethyl,

m is the numbers 0, 1, 2 or 3, where R "is identical or different radicals, when m is 2 or 3,

R '"represents methyl, ethyl, fluorine, chlorine or trifluoromethyl

and

n is the numbers 0, 1, 2 or 3, where R '"is identical or different radicals, when n is 2 or 3.

R ³ is (C ₁ -Co) -alkyl, _(C3 -6) alkenyl, (C ₃ -C 6) -alkynyl, (C ₃ -C 8) cycloalkyl or benzyl, wherein R ³ is unsubstituted or substituted by one or more fluorine - or chlorine atoms and / or alkyl is substituted, or

R ³ is phenyl which may be monosubstituted to trisubstituted, identically or differently substituted by

Fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, ethynyl, alyl, propargyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, Trifluoromethylsulfinyl, trifluoromethylsulfonyl, trichloroethinyloxy, trifluorethinyloxy, chloroallyloxy, iodopropargyloxy, methylamino, ethylamino, n- or i-propylamino, dimethylamino,

Diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or by

1,3-propanediyl linked in the 2,3-position, 1,4-butanediyl, methylenedioxy (-O-CH ₂ -O-) or 1,2-ethylenedioxy (-O-CH ₂ -CH ₂ -O-), where these radicals may be substituted one or more times, identically or differently by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl, carboxy and / or carboxymethyl

R ³ is pyridyl, which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine,

Cyano, hydroxy, mercapto, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is thienyl which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is C ₁ -C ₆ -alkylamino or di-C ₁ -C ₆ -alkylamino, or

R ³ is thiazolyl which is linked in the 2-, 4- or 5-position and may be mono- to disubstituted by identical or different substituents by fluorine, chlorine, bromine,. Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ³ is N-piperidinyl, N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1,2,4-triazolyl,

N-pyrrolyl, or N-morpholinyl, each unsubstituted or one or - if possible - several times the same or different by fluorine, chlorine, bromine, cyano, Nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl substituted

R ⁸ is H, (C _r C ₈ ) alkyl, (C _r C ₈ ) haloalkyl, (C ₃ -C ₆ ) alkenyl, propargyl, (C ₃ -C ₈ ) cycloalkyl, benzyl; or two radicals R ⁸ form a cycle having 3 to 6

Carbon atoms which is saturated or partially unsaturated and optionally

Contains 1 or 2 further N, S or O atoms, oxygen atoms not being allowed to be adjacent;

R ⁴ is CONR ⁶ R ⁷ ;

R ^{5 is} H, Cl, F, CH ₃ , -CH (CH ₃ ) 2 or cyclopropyl;

X is H, F, Cl, CN, unsubstituted or substituted by one or more fluorine or chlorine atoms C ^ -C ^ alkyl;

R ⁶ is H, Na, K, V ₂ Ca, V ₂ Mg, Cu, NH ₄ , NH (CH ₃ ) ₃ , N (CH ₃ ) ₄ , HN (C ₂ H ₅ ) ₃ , N (C ₂ Hj ) ₄ , H ₂ N (iC ₃ H ₇ ) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, cholinium, (C _r C ₈ ) -alkyl, (C ₃ -Cg) -alkenyl, (C ₃ -C ₈ ) -cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl, phenyl, benzyl;

R ⁷ is COR ⁸ , S (O) i. ₂ R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , pyrrolyl, imidazolyl, pyrazolyl, 1,3,4-triazolyl, thiazolyl, isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, Oxazolyl, isoxazolyl, tetrazolyl, oxadiazinyl, 4H- [l, 2,4] -oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, Pyrimidinyl, pyrazinyl, pyridazinyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group Ci-Gj-alkyl, C ₁ -C ₄ -alkoxy and halogen;

R ⁸ is H, (dC ^ alkyl, (C _r C ₈₎ haloalkyl, (C ₃ -C ₆₎ -alkenyl, propargyl, (C ₃ -C ₈₎ -

Cycloalkyl, benzyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms, which is saturated or partially unsaturated and optionally

Contains 1 or 2 further N, S or O atoms, oxygen atoms not being allowed to be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) i _-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms from the group Series may contain sulfur, oxygen and / or nitrogen, wherein oxygen atoms may not be adjacent;

6. pyrazolopyrimidines of the formula (J) according to one or more of claims 1 to 5, wherein the symbols have the following meanings

R ¹ and R ² have the meanings given in claims Ibis 5;

R ³ is (C ₁ -C ₆₎ alkyl, (C ₃ - ₆₎ alkenyl, (C ₃ -C ₆₎ -alkynyl, (C ₃ -C ₈₎ -cycloalkyl, wherein R ³ is unsubstituted or by one or a plurality of fluorine or chlorine atoms and / or alkyl is substituted,

or

R ³ is 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substituted phenyl or for

2,4,6- or 2,4,5-trisubstituted phenyl having substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, meth oximinoethyl, carboxy and / or carboxymethyl or

R ³ is pyridyl which is linked in the 2- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine, cyano, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl , Methoximinomethyl, methoximinoethyl, trifluoromethyl and / or carboxymethyl or

R ³ is pyrimidyl which is linked in the 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, Methoximinoethyl, trifluoromethyl, and / or carboxymethyl;

R ³ is thienyl, which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , Hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl or

R ⁴ is CONR ⁶ R ⁷ ; R ⁵ is H, -CH ₃ , -CH (CH ₃ ) ₂ , Cl or cyclopropyl; and

X is fluorine, chlorine, (C ₁ -C 4) -alkyl or (C ₁ -C 5) -haloalkyl;

R ⁶ is H, Na ₁ K ₅ NH ₄ , HN (Et) ₂ , H ₂ N (iPr) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, wholly or partly by F and / or Cl and / or carboxy (C ₁ -C ₄ ) -alkyl, CONR ⁶ R ⁷ , CONR ⁷ OR ⁷ , COOR ⁸ substituted (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) -alkenyl, propargyl, (C ₃ -

C ₈ ) cycloalkyl, benzyl;

R ⁷ is COR ⁸ , S (O) i _-2 R ⁸ , cyano, COOR ⁸ , CON (R ⁸ ) ₂ , 1-H-pyrrolyl, 1-H-imidazolyl, 1,3,4-oxadiazolyl, 1 H-pyrazolyl, isoxazolyl, oxazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl, 1-H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [1,2 , 4] -oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, wherein the heterocyclic radicals are optionally substituted by one or more radicals from the Group C ₁ -C ₄ -alkyl and halogen.

R ⁸ is H, (C _r C ₈ ) alkyl, (C ₃ -C ₆ ) alkenyl, propargyl, (C ₃ -C ₈ ) cycloalkyl, benzyl; or two radicals R ⁸ form a cycle having 3 to 6 carbon atoms which is saturated or partially unsaturated and optionally 1 or 2 further N, S or O radicals

Contains atoms, wherein oxygen atoms may not be adjacent;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) _1-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen can contain, where

Oxygen atoms must not be adjacent;

7. pyrazolopyrimidines of the formula (I) according to one or more of claims 1 to 6 wherein the symbols have the following meanings

R ¹ and R ² have the above-mentioned particularly preferred meanings;

R ³ is 2,4-, 2,5- or 2,6-disubstituted phenyl, or 2-substituted phenyl or

2,4,6- or 2,4,5-trisubstituted phenyl having substituents from the group of fluorine, chlorine, bromine, cyano, nitro, hydroxyl, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoxy oximinoethyl, carboxy and / or carboxymethyl or R 3 is thienyl which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine,

Cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, trifluoromethyl, carboxy and / or carboxymethyl;

R ⁴ is CONR ⁶ R ⁷ ;

R ⁵ is H, -CH ₃ ;

X is fluoro, chloro, methyl or trifluoromethyl;

R ⁶ is H, Na, K, NH ₄ , HN (Et) ₂ , H ₂ N (iPr) ₂ , H ₃ NCH ₂ Ph, (H ₃ C) ₃ NCH ₂ Ph, in whole or in part by F and / or Cl and / or carboxy (C 1 -C ₄ ) -alkyl, CONR ⁶ R ⁷ ,

CONR ⁷ OR ⁷ , COOR ⁸ substituted (C _r C ₈ ) alkyl, (C ₃ -C ₆ ) alkenyl, propargyl, (C ₃ -C ₈ ) cycloalkyl, benzyl;

R ⁷ is COR ⁸ , S (O) ₂ R ⁸ , COOR ⁸ , 1-H-pyrrolyl, 1-H-imidazolyl, 1,3,4-oxadiazolyl, 1-H-pyrazolyl, isoxazolyl, oxazolyl, 1.3 , 4-oxadiazolyl, 1,3,4-thiadiazolyl, thiazolyl, isothiazolyl, 1-H-1,3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [l, 2,4] -oxadiazin-3-yl, dioxazinyl , 5,6-dihydro- [l, 4,2] -dioxazin-3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals from the group Ci-GrAlkyl and halogen.

R ⁸ is independently of one another H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, (C ₁ -C 3) -haloalkyl, (C ₂ -C ₆ ) Alkenyl, propargyl, (C ₃ -

C ₆ ) cycloalkyl, benzyl;

or

R ⁶ and R ⁸ together with the N-CO or NS (O) _1-2 group to which they are attached form a 4-8 membered cycle containing one or more heteroatoms selected from sulfur, oxygen and / or nitrogen can contain, where

Oxygen atoms must not be adjacent;

8. A composition for controlling unwanted microorganisms, characterized by a content of at least one pyrazolopyrimidine of the formula (I) according to one or more of claims 1 to 7 in addition to extenders and / or surface-active substances.

9. Composition according to claim 8, characterized by a content of at least one further agrochemical active ingredient.

10. Use of pyrazolopyrimidines of the formula (I) according to one or more of claims 1 to 7 for controlling unwanted microorganisms.

11. A method for controlling unwanted microorganisms, characterized in that pyrazolopyrimidines of the formula (I) according to one or more of claims 1 to 7 on the unwanted microorganisms and / or their habitat brings.

12. A process for the preparation of compositions for controlling unwanted microorganisms, which comprises mixing pyrazolopyrimidines of the formula (I) according to one or more of claims 1 to 7 with extenders and / or surface-active substances.

13. A process for the preparation of the compounds of the formula (T) in which X is chlorine and R ^{4 is} CONR ⁶ R ⁷ and the other symbols have the meanings given in formula (I) in claim 1,

a) by reacting substituted 3-aminopyrazole derivatives of the formula π,

and malonates Ha

where R ^{10 is} C _r C ₄ -alkyl and R ^{11 is} C ₁ -C ₈ -alkyl or aryl,

to dihydroxypyrazolopyrimidines DI,

b) Halogenation of IE to Halogenpyrazolopyrimidinen IV _3rd

c) reaction of IV with amines to give 7-aminopyrazolopyrimidines V,

d) saponification to pyrazolopyrimidinecarboxylic acids VI,

e) Reaction with a chlorinating agent to Pyrazolopyrimidinsäurechloriden VII ₅

- -

and f) reaction of VH with HNR ⁶ R ⁷ to give compounds of the formula (Ia)