EP1797097A1 - 7-aminomethyl-1,2,4-triazolo[1,5-a]pyrimidine compounds and their use for controlling pathogenic fungi - Google Patents

Abstract

The invention relates to 7-aminomethyl-1,2,4-triazolo[1,5-a]pyrimidine compounds of general formula (I) and the agriculturally compatible salts of said compounds. In said formula: R1 and R2 represent hydrogen, alkyl, haloalkyl, alkoxy, cycloalkyl, bicycloalkyl, halocycloalkyl, alkenyl, alkadienyl, haloalkenyl, cycloalkenyl, halocycloalkenyl, alkynyl, haloalkynyl or phenyl, naphthyl, or a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle, containing 1 to 4 heteroatoms from the group containing O, N or S, or R1 and R2, together with the nitrogen atom to which they are bonded, can also form a five- or six-membered heterocyclyl or heteroaryl, which is bonded by means of N and can contain 1 to 3 additional heteroatoms from the group containing O, N and S as the ring member and can be substituted according to the description; R3 and R4 represent hydrogen, alkyl, haloalkyl, haloalkoxy, alkoxy, or alkoxyalkyl; X represents halogen, cyano, a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle, containing 1, 2 or 3 heteroatoms from the group containing O, N or S as the ring member, alkyl, alkoxy, alkenyl or alkynyl, whereby the latter 4 groups can be substituted according to the description; L is defined as cited in the claims and the description; and m represents 0, 1, 2, 3, 4 or 5. The invention also relates to the use of the triazolopyrimidine compounds of general formula (I) and their agriculturally compatible salts for controlling plant-pathogenic fungi, to a method for controlling plant-pathogenic fungi, containing at least one compound of general formula (I) and/or an agriculturally compatible salt of said compound and at least one liquid or solid carrier.

Description

7-aminomethyl-1, 2,4-triazolo [1, 5-a] pyrimidin-Ver ^'compounds and their use for controlling harmful fungi

description

The present invention relates to novel 7-aminomethyl-1, 2,4-triazolo [1, 5-a] pyrimidine compounds and their use for controlling harmful fungi and Pflan¬ zenschutzmittel containing at least one such compounds as an effective Bestand¬ part.

EP-A 71 792, EP-A 550 113, EP-A 834 513 and WO-A 98/46608 describe fungi cid effective 1, 2,4-triazolo [1, 5-a] pyrimidines, which in the 6-position an optionally substituted phenyl ring, in the 5-position a halogen atom and in the 7-position carry an amino group.

WO-A-99/41255 describes fungicidally active 1,2,4-triazolo [1,5-a] pyrimidine compounds which have, in the 5-position, a halogen atom, a cyano, haloalkoxy or alkoxy group and the 7-position carry an optionally substituted aliphatic, cycloaliphatic or aromatic radical.

WO 03/004465 describes fungicidally active 1,2,4-triazolo [1, 5-a] pyrimidine compounds which have in the 7-position an optionally substituted aliphatic, cycloaliphatic or aromatic radical and in which Position carry an optionally substituted alkyl, alkenyl or alkynyl group.

The 1,2,4-triazolo [1,5-a] pyrimidines known from the prior art are in some cases unsatisfactory with respect to their fungicidal activity or have undesirable properties, such as a low compatibility with crops.

The present invention is therefore based on the object to provide new compounds with better fungicidal activity and / or better crop compatibility.

This object is surprisingly achieved by 1, 2,4-triazolo [1, 5-a] pyrimidines of the general formula I.

wherein the index m and the substituents R ¹ , R ² , R ³ , R ⁴ , X and L have the following meanings:

R ¹ , R ² independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkoxy, C ₃ -C ₈ -cycloalkyl, C ₅ -C ₁₀ -cycloalkyl, C ₃ - C ₈ -halocycloalkyl, C ₂ -C ₈ -alkenyl, C ₄ -C ₁₀ -alkadienyl, C ₂ -C ₈ -haloalkenyl, C ₃ -C ₆ -cycloalkenyl, C ₃ -C ₆ -halocycloalkenyl, C ₂ -C ₈ Alkynyl, C ₂ -C ₈ -haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N or S,

R ¹ and R ² may also together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and one, two or three further heteroatoms from the group O, N and S may contain as ring member and / or one or more Substi¬ tuents from the group halogen, CVCe-alkyl, CrC ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₁ -C ₆ - AIkOXy, d-Ce-alkoxycarbonyl, C _r C ₆ halo-alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy can carry and / or wherein two bonded to adjacent ring atoms substituents for d-Cβ-alkylene , Oxy-C ₂ -C ₄ -alkylene or OXy-C ₁ -C ₃ -alkylenoxy may stand;

R ¹ and / or R ² may carry one, two, three or four identical or different groups R ^a :

R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, C _r C ₆ alkyl, C _r C ₆ haloalkyl, CrCβ alkyl-carbonyl, C ₃ -C ₆ cycloalkyl, C _r C ₆ alkoxy, -C ₆ haloalkoxy, CRCE alkoxycarbonyl, -C ₆ -alkylthio, C _r C ₆ alkylamino, di-CrC ₆ alkyl amino, d-Ce-alkylaminocarbonyl, di-CRCE-alkylaminocarbonyl,

C ₂ -C ₈ -alkenyl, C ₄ -C ₁₀ -alkadienyl, C ₂ -C ₈ -haloalkenyl, C ₃ -C ₈ -cycloalkenyl, C ₂ -C ₆ -alkenyloxy, C ₃ -C ₆ -haloalkenyloxy, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₆ -haloalkynyloxy, C ₃ -C ₆ -cycloalkoxy, C ₃ -C ₆ -cycloalkenyloxy, OXy- C ₁ -C ₃ -alkyleneoxy, phenyl, naphthyl, five-, six-, seven-, eight-, nine- or ten-membered saturated ter, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N or S,

in which the aliphatic, alicyclic or aromatic groups in R ^{a are in} turn partially or completely halogenated or one, two or three

Groups R ^{b can} carry:

R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino carbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkadienyl, alkeneyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino,

Dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the said alkenyl, alkadienyl or alkynyl groups in den¬ radicals contain from 2 to 8 carbon atoms;

and / or one, two or three of the following radicals:

Cycloalkyl, bicycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, wherein the cyclic systems contain 3 to 10 ring members; Aryl, aryloxy, arylthio, aryl-Ci-C ₆ -alkoxy, aryl-CrCe-alkyl, hetaryl, hetaryl-oxy, hetarylthio, wherein the aryl radicals preferably 6, 7, 8, 9 or 10 ring members, the hetaryl radicals 5 or 6 ring members wherein the cyclic systems may be partially or completely halogenated or substituted by alkyl or haloalkyl groups;

R ^3, R ⁴ are independently hydrogen, Ci-C ₈ alkyl, CrC ₈ -HalogenaIkyl,

CRCS haloalkoxy, -C ₈ alkoxy, can be dC ₈ -haloalkoxy or CrC-a-alkoxy-CiC-β-alkyl, where the 6 last-mentioned radicals carry one, two, three or four identical or different radicals R ^0, wherein R ° has the meanings given for R ^a ;

X is halogen, cyano, 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle containing 1, 2 or 3 heteroatoms from the group O,

N or S as a ring member, C _r C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₈ alkenyl or C ₂ -Cs alkynyl, where the four latter radicals may be partially or completely halogenated and / or one, two or three substituents selected un¬ ter nitro, cyano, -C ₂ -alkoxy, dC ₄ alkoxycarbonyl, amino, alkylamino C ₁ -C ₄ -alkyl and di-C ₁ -C ₄ alkylamino, wear can and the 5- or 6-membered heterocycle one or more substituents from the group halogen, C ₁ -C ₆ -AIRyI, C _r C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ -alkoxy, CrCe- alkoxycarbonyl, -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkylene can carry and oxy-C ₁ -C ₃ -alkyleneoxy ₆ -haloalkenyloxy, (6Xo) C ₁ -C;

Halogen, cyano, hydroxy, cyanato (OCN), nitro, C ₁ -C ₈ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₁₀ haloalkenyl, C _r C ₆ alkoxy, C ₂ -C ₁₀ alkenyloxy, C ₂ -C ₁₀ alkynyloxy, CRCE haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl, C ₃ -C ₆ -cycloalkoxy, C 1 -C 5 -alkoxycarbonyl,

C ₂ -C ₁₀ alkenyloxycarbonyl, C ₂ -C ₁₀ alkynyloxycarbonyl, aminocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, di- (C ₁ -C ₈ ) -alkylaminocarbonyl, C ₁ -C 6 -alkoximinoalkyl, C ₂ -C ₁ o-alkenyloximinocarbonyl, C ₂ -C ₁₀ - Alkynyloximinoalkyl, C ₁ -C ₄ -alkylcarbonyl, C ₂ -C ₁ 0-alkenylcarbonyl, C ₂ -C ₁₀ -alkynylcarbonyl, C ₃ -C ₆ -cycloalkylcarbonyl, a five, six, seven, eight, nine or ten membered saturated, partial unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N or S, amino, NR ⁵ R ⁶ , NR ⁵ - (C =O) -R ⁶ , S (= O ) _n A ¹ , C (= O) A ² , C (= S) A ² , a group -C (S) NR ⁷ R ⁸ , a group -C (= N-OR ⁹ ) (NR ¹⁰ R ¹¹ ) or, a group -C (= N-NR ¹² R ¹³ ) (NR ¹⁴ R ¹⁵ ),

wherein

R ⁵ , R ^{6 are} independently selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₁₀ -alkyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ - Cycloalkenyl, where the 5 last-mentioned radicals may be partially or completely halogenated or one, two, three or four radicals selected from cyano,

C ₁ -C ₄ alkoximino, C ₂ -C ₄ alkenyloximino, C ₂ -C ₄ alkynyloximino or C ₁ -C ₄ alkoxy;

A ¹ represents hydrogen, hydroxy, Ci-C ₈ alkyl, CRCS alkylamino or di- (C ₁ -C ₈ alkyl) amino;

n is 0, 1 or 2;

A ² is C ₂ -C ₈ alkenyl, C ₁ -C ₈ -alkoxy, CrC ₆ haloalkoxy, amino, or one of said at A ¹ groups is;

R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ^{15 are} independently selected from hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, where the four last-mentioned radicals may have one, two, three, four, five or six radicals R ^a ; or R ⁷ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹² and R ¹³ and / or R ¹⁴ and R ¹⁵ together with the nitrogen atom to which they are attached, a four-, five- or six-membered saturated or partially unsaturated Ring, which can carry one, two, three or four, independently selected from R ^a selected substituents;

m is 0, 1, 2, 3, 4 or 5;

and by the agriculturally acceptable salts of the compounds I.

The present invention thus relates to the 7-aminomethyl-1, 2-4-triazolo [1, 5-a] compounds of the general formula I and their agriculturally acceptable salts.

The present invention furthermore relates to the use of the 7-amino-methyl-1, 2-4-triazolo [1, 5-a] compounds of the general formula I and their agriculturally acceptable salts for controlling phytopathogenic fungi (= harmful fungi ) and a method for controlling phytopathogenic Schad¬ mushrooms, which is characterized in that the fungi, or to be protected against fungal infection, materials, plants, the soil or seeds with an effective amount of at least one compound of general formula I, and / or treated with an agriculturally acceptable salt of I.

The present invention furthermore relates to an agent for controlling harmful fungi, comprising at least one compound of the general formula I and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.

Depending on the substitution pattern, the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures. The invention relates to both the pure enantiomers or diastereomers and mixtures thereof. Suitable compounds of general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.

Salts which can be used agriculturally are, above all, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I. For example, the cations used are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium. and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which may if desired carry one to four C 1 -C ₄ -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, Tetrabutylammonium, trimethylbenzyl ammonium, further phosphonium ions, sulfonium ions, preferably tri (C _r C ₄ alkyl) sulfonium and Sulfoxoniumionen, preferably Tn (C ₁ -C ₄ alkyl) sulfoxonium, into consideration.

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

The definitions of variables given in the above formulas use collective terms that are generally representative of the respective substituents. The meaning C _n -C _n , indicates the particular possible number of carbon atoms in the respective substituent or substituent part:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, e.g. C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2 , 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl , 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above!), In which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular CrC ₂ - Haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;

Alkenyl: monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a double bond in any position, for example C ₂ -C ₆ -alkenyl, such as ethenyl, 1-propenyl, 2 -Propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl , 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2 Methyl 2-butenyl, 3-methyl-2-butenyl,

1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2 -pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3 Methyl 4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl 2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl 3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl 2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-but enyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl 1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like;

Alkadienyl: diunsaturated, straight-chain or branched hydrocarbon radicals having 4 to 10 carbon atoms and two double bonds in any position, for example 1, 3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1, 3 butadienyl, penta-1,3-dien-1-yl, hexa-1, 4-dien-1-yl, hexa-1,4-dien-3-yl, hexa-1,4-dien-6-yl, Hexa-1, 5-dien-1-yl, hexa-1, 5-dien-3-yl, hexa-1, 5-dien-4-yl, hepta-1, 4-dien-1-yl, hepta- 1, 4-dien-3-yl, hepta-1, 4-dien-6-yl, hepta-1, 4-dien-7-yl, hepta-1, 5-dien-1-yl, hepta-1, 5-dien-3-yl, hepta-1, 5-dien-4-yl, hepta-1, 5-dien-7-yl, hepta-1, 6-dien-1-yl, hepta-1, 6- dien-3-yl, hepta-1, 6-dien-4-yl, hepta-1, 6-dien-5-yl, hepta-1, 6-dien-2-yl, octa-1, 4-diene 1 -yl, octa-1, 4-dien-2-yl, octa-1, 4-dien-3-yl, octa-1, 4-dien-6-yl, octa-1, 4-diene-7 yl, octa-1, 5-dien-1-yl, octa-1, 5-dien-3-yl, octa-1, 5-dien-4-yl, octa-1, 5-dien-7-yl, Octa-1, 6-dien-1-yl, octa-1, s-dien-3-yl, octa-1, 6-dien-4-yl, octa-1, 6-dien-5-yl, octa-1 1, 6-dien-2-yl, deca-1,4-dienyl , Deca-1, 5-dienyl, Deca-1, 6-dienyl, Deca-1, 7-dienyl, Deca-1, 8-dienyl, Deca-2,5-dienyl, Deca-2,6-dienyl, Deca -2,7-dienyl, deca-2,8-dienyl and the like; Haloalkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above), where in these groups, the hydrogen atoms partially or completely against halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, may be replaced;

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two triple bonds in any position, for example C ₂ -C ₆ -alkynyl, such as ethynyl, 1-propynyl, 2 Propynyl, 1-butynyl,

2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 3-ethyl / 1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl , 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 pentynyl, 3-methyl-4-pentynyl,

4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2.2- Dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2- propynyl and the like;

Cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;

Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups having 3 to 8, preferably 5 to 6 carbon ring members, such as cyclopentene-1-yl, cyclopentene-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the same;

Bicycloalkyl: bicyclic hydrocarbon radical having 5 to 10 C atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl and the like;

C ₁ -C ₄ -alkoxy: for an oxygen-bonded alkyl group having 1 to 4 carbon atoms: z. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;

C ₁ -C ₆ -Akoxy: for C ₁ -C ₄ -alkoxy, as mentioned above, and z. Pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3- Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,

3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy,

1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

-C ₄ -haloalkoxy: a C _r C ₄ alkoxy as mentioned above, the, chlorine, bromine / or iodine and is preferably fluorine stituiert sub¬ by partially or fully by fluorine, ie. OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCHCl ₂ , OCCl ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,

2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy , 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxy, 1 - (CH ₂ Cl) -2-chloroethoxy, 1 - (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or monafluorobutoxy;

d-Ce-haloalkoxy: for CrC ₄ haloalkoxy, as mentioned above, and z. 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;

Alkenyloxy: Alkenyl as mentioned above, which is bonded via an oxygen atom, for. B. C ₃ -C ₆ alkenyloxy such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy,

1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2- Methyl 2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyloxy, 1, 2-Dimethyl-1-propenyloxy, 1, 2-dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5 -Hexenyloxy, 1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy, 3-methyl-1-pentenyloxy, 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy , 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl 4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1, 1-dimethyl-2-butenyloxy, 1, 1-dimethyl-3-butenyloxy, 1 , 2-Dimethyl-1-butenyloxy, 1, 2-dimethyl-2-butenyloxy, 1, 2-dimethyl-3-but enyloxy, 1,3-dimethyl-1-butenyloxy, 1, 3-dimethyl-2-butenvloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-1 - butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3-dimethyl-2-butenyloxy, 1-ethyl-1-butenyloxy, 1 - Ethyl 2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-1-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1, 1, 2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy, 1-ethyl-2-methyl-1-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy;

Alkynyloxy: alkynyl as mentioned above, which is bonded via an oxygen atom, for. B. C ₃ -C ₆ alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy,

1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy and the like;

5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms from the group consisting of oxygen, nitrogen or sulfur:

Five- or six-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: z. B. monocyclic saturated or par¬ tially unsaturated heterocycles (heterocyclyl) containing in addition to carbon ring¬ members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,

3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2- imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2,4-thiadiazolidine 5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl,

1, 3,4-thiadiazolidin-2-yl, 1, 3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofuran 2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydro-thien-2-yl, 2,3-dihydro-thien-3-yl, 2,4-dihydro-thien-2-yl, 2,4-dihydro-thienyl 3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazoline-3 yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,

2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2- isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- Dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4- dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,

3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3-dioxane-5 yl, 2-tetrahydropyranyi, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3,5-hexahydro-triazin-2 yl and

1, 2,4-hexahydrotriazin-3-yl and the corresponding -ylidene radicals;

Seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur as ring members: e.g. mono- and bicyclic heterocycles having 7 Ring¬ members containing in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and Hexahydroazepinyl as 2,3,4,5 -Tetrahydro [1 H] azepine-1, -2, -3, -A, 5, 6 or 7-yl, 3,4,5,6-tetrahydro [2H] azepine 2-, 3-, -A-, -5-, -6- or -7-yl,

2,3,4,7-tetrahydro [1 H] azepine-1, -2, -3, -A, 5, 6 or 7-yl, 2,3,6,7 Tetrahydro [1 H] azepine-1, -2, -3, -A, 5, 6 or 7-yl, hexahydroazepine 1 -, 2 -, 3 - or - 4-yl, tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro [1H] oxepin-2, 3, -A, 5, 6 or 7-yl, 2, 3,4,7-tetrahydro [1H] oxepin-2, 3, -A, 5, 6 or 7-yl,

2,3,6,7-tetrahydro [1 H] oxepin-2-, -3-, -A-, -5-, -6- or -7-yl, hexahydroazepine-1 -, -2-, -3 - or 4-yl, tetra- and hexahydro-1, 3-diazepinyl, tetra- and hexahydro-1, 4-diazepinyl, tetra- and hexahydro-1, 3-oxazepinyl, tetra- and hexahydro-1, 4-oxazepinyl , Tetra- and hexahydro-1, 3-dioxepinyl, tetra- and hexahydro-1, 4-dioxepinyl and the corresponding yliden radicals.

A five- or six-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen or sulfur: mono- or binuclear heteroaryl, eg. B. C-linked 5-membered heteroaryl containing one to three nitrogen atoms or one or two nitrogen atoms and a

Sulfur or oxygen atom as ring members such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl , 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 , 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 2,4-triazol-3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2-yl and 1, 3,4-triazol-2-yl; 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms as ring members, such as pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1, 2,3-triazol-1-yl and 1, 2 4-triazol-1-yl;

6-membered heteroaryl containing one to three nitrogen atoms as ring members such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5- Pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl;

Alkylene: divalent linear chains of 1 to 6 CH ₂ groups, e.g. B. CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ and CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ J

Oxyalkylene: divalent unbranched chains of 2 to 4 CH ₂ groups, wherein a valence is bonded via an oxygen atom to the skeleton, z. OCH ₂ CH ₂ , OCH ₂ CH ₂ CH ₂ and OCH ₂ CH ₂ CH ₂ CH ₂ ;

Oxyalkylenoxy: divalent unbranched chains of 1 to 3 CH ₂ groups, wherein both valences are bonded via an oxygen atom to the skeleton, z. OCH ₂ O, OCH ₂ CH ₂ O and OCH ₂ CH ₂ CH ₂ O.

With regard to the effectiveness of the compounds of the formula I according to the invention as fungicides, the subscript m and the substituents R ¹ , R ² , R ³ , R ⁴ , X and L, independently of one another and preferably in combination, particularly preferably have the following meanings:

Compounds of the general formula I are preferred in which at least one of the radicals R ¹ or R ^{2 is} different from hydrogen.

Compounds of general formula I are particularly preferred in which R ¹ is d-Ce-alkyl, C ₂ -C ₆ -alkenyl -alkyl, C ₂ -C ₆ alkynyl or C _r C is ₈ haloalkyl.

Compounds of general formula I are also particularly preferred in which R ^{1 is} a group B:

wherein Z ^{1 is} hydrogen, fluorine or C 1 -C ₆ -fluoroalkyl, Z ^{2 is} hydrogen or fluorine, or

Z ¹ and Z ² together form a double bond; q is 0 or 1; and R ^{16 is} hydrogen or methyl.

In addition, compounds of general formula I are particularly preferred in which R ^{1 is} C ₃ -C ₆ -cycloalkyl, which may be substituted by C ₁ -C ₄ -alkyl.

Preference is given to compounds of the general formula I in which R ^{1 is} different from hydrogen and R ^{2 is} hydrogen. R ¹ then preferably has one of the be¬ preferred, or particularly preferred meanings given.

Equally preferred are compounds of the general formula I in which R ¹ and R ² are different from hydrogen. Preference is given to compounds of the general formula I in which R ^{2 is} methyl or ethyl. R ¹ then preferably has one of the preferred, or particularly preferred, indicated meanings.

Furthermore, particular preference is given to compounds of the general formula I in which R ¹ and R ² together with the nitrogen atom to which they are bonded represent saturated heterocyclyl as defined above and in particular form a piperidinyl, morpholinyl or thiomorpholinyl ring, especially a piperidinyl ring , Heterocyc¬ lyl then is unsubstituted or substituted in the manner described above, especially by 1, 2 or 3 substituents R ^a, where preferred substituents on heterocyclyl are selected from halogen, C _r C ₄ alkyl, and -C ₄ haloalkyl. Very particular preference is given to compounds I in which R ¹ and R ² together with the nitrogen atom to which they are attached form a 4-methylpiperidine ring or 3,4-dimethylpiperidine ring.

Another particularly preferred object of the invention are compounds I in which R ¹ and R ² together with the nitrogen atom to which they are attached form a 5- or 6-membered heteroaryl as defined above, which may be unsubstituted or substituted , preferably by 1, 2 or 3 groups R ^a . In particular, the group NR ¹ R ² forms a pyrazole ring, which is optionally substituted in the manner described above, and especially by 1 or 2 of the following radicals: halogen, -C ₄ alkyl or C ₄ -haloalkyl, in particular by 2 methyl groups or 2 trifluoromethyl groups in 3,5-position. Particular preference is given to compounds of the general formula I in which R ¹ is chosen from: CH (CH ₃ ) -CH ₂ CH ₃ , CH (CH ₃ ) -CH (CH ₃ ) ₂ , CH (CH ₃ ) -C (CH ₃ ) _{3) 3,} CH (CHs) -CF _3, CH ₂ C (CHs) = CH _2, CH ₂ CH = CH _2, cyclopentyl or cyclohexyl; and R ^{2 is} hydrogen or methyl; and compounds I wherein R ¹ and R ² together are - (CH ₂ ) ₂ CH (CH ₃ ) (CH ₂ ) ₂ -, - (CH ₂ ) ₂ CH (CF ₃ ) (CH ₂ ) ₂ - or - (CH ₂ ) ₂ O (CH ₂ ) ₂ - mean.

Compounds of general formula I are preferred in which R ³ and R ⁴ unab¬ pendently hydrogen, C _r C ₄ alkyl or C _r C ₄ alkoxy, particularly preferably hydrogen, C _r C ₂ -alkyl, such as Methyl or ethyl or C ₁ -C ₂ -alkoxy, such as methoxy or ethoxy.

Particular preference is given to compounds I in which at least one of the radicals R ³ or R ^{4 is} hydrogen and the other radical R ³ or R ^{4 has} the abovementioned meanings and in particular represents hydrogen, methyl or ethyl.

Among the compounds of general formula I are furthermore preferred in which X is halogen, cyano, -C ₄ alkyl, -C ₄ haloalkyl, C ₁ -C ₄ -alkoxy or C ₂ -haloalkoxy stands. In particular, compounds of general formula I are preferred in which X is halogen, -C ₂ alkyl, cyano or C _r C ₂ alkoxy, such as chlorine, methyl, cyano, methoxy or ethoxy. X is especially halogen and especially chlorine.

In the general formula I, m is preferably 1, 2, 3 or 4 and in particular 1, 2 or 3.

Preferred meanings of L are: halogen, cyano, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, a group C (S) A ² or a group C (O) A ² , wor¬ in A ² has the meanings given above and preferably C ₁ -C ₄ -alkoxy, NH _2, -C ₄ alkylamino or di-C ₁ -C ₄ -alkylamino stands. Particularly preferred are connects fertilize the general formula I in which the radicals L are independently selected aus¬ from fluorine, chlorine, bromine, cyano, nitro, C _r C ₄ alkyl, C _r C ₄ haloalkyl, C ₁ - C ₄ -alkoxy and CrC ₄ alkoxycarbonyl, especially preferably fluorine, chlorine, C ₁ -C ₂ -AIk ^ as methyl or ethyl, -C ₂ fluoroalkyl such as trifluoromethyl, C ₁ -C ₂ -alkoxy such as methoxy or d-like CrAlkoxycarbonyl methoxycarbonyl. In addition, preference is given to compounds of the general formula I in which at least one radical L is located ortho to the point of attachment to the triazolopyrimidine skeleton. A radical L arranged in the ortho position is preferably selected from halogen, especially fluorine or chlorine. In particular, m is 2 or 3 and at least one residue L is located ortho to the point of attachment to the triazolopyrimidine skeleton. Among these, preferred compounds of the general formula I are those in which a radical L in the 2-position and a further radical L in the 5-position to the point of attachment to the triazolopyrimidine skeleton are arranged. Of these, compounds of general formula I are likewise preferred in which a residue L in the 2-position and a further residue L in the 4-position to the point of attachment to the triazolopyrimidine skeleton are arranged. Of these, compounds of the general formula I are likewise preferred, in which a radical L in the 2-position and a further radical L in the 6-position to the point of attachment to the triazolopyrimidine skeleton are arranged.

In particular, those compounds of the general formula I are particularly preferred, in which the phenyl group substituted by L _{m is} the group C

where # is the site of attachment to the triazolopyrimidine skeleton and

L ^{1 is} fluorine, chlorine, trifluoromethyl or methyl; L ^{2 is} hydrogen, chlorine or fluorine;

L ^{3 is} hydrogen, CN, nitro, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, a group C (S) A ^2a or a group C (O) A ^2a , where A ^{2a is} C _r C ₄ alkoxy, NH ₂ , C 1 -C ₄ alkylamino or di-C 1 -C ₄ alkylamino; L ^{4 is} hydrogen, chlorine or fluorine; and L ^{5 are} hydrogen, fluorine, chlorine or C _r C ₄ alkyl.

Moreover, R ⁵ and R ⁶ independently of one another are preferably hydrogen or C _r C ₄ alkyl.

In the radical -C (S) N ⁷ R ⁸ R ⁷ and R ⁸ are each independently preferably ausge¬ selected from hydrogen or C _r C ₆ alkyl, especially hydrogen or C _r C ₄ alkyl such as methyl, ethyl, n- Propyl or isopropyl, especially hydrogen.

R ⁹ is preferably hydrogen or C 1 -C ⁶ -alkyl. R ¹⁰ and R ¹¹ independently of one another preferably represent hydrogen or C 1 -C ₆ -alkyl.

R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are preferably independently selected from hydrogen or C ₁ -C ₆ alkyl.

Furthermore, A ^{1 is} preferably hydrogen, C ₁ -C ₆ -alkyl or amino. The index n is preferably 0, 1 or 2.

A ² is preferably C ₁ -C ₄ -alkoxy, NH _2, -C ₄ alkylamino or di-C ₁ -C ₄ alkylamino.

A preferred embodiment of the invention relates to compounds of the formula 1.1

G

wherein

GC ₂ -C ₆ -alkyl, in particular ethyl, n- and i-propyl, n-butyl, sec-butyl, tert-butyl, and C-rCvrAlkoxymethyl, in particular ethoxymethyl, or C ₃ -C ₆ -cycloalkyl, in particular cyclopentyl or cyclohexyl;

R ^{2 is} hydrogen or methyl;

R ³ and R ⁴ are independently hydrogen or C _r C ₄ alkyl;

X is chlorine, methyl, cyano, methoxy or ethoxy;

L is halogen, cyano, nitro, -C ₆ alkyl, -C ₆ haloalkyl, C ₁ -C ₆ -alkoxy, a group C (S) A ² or a group C (O) A ^2, wherein A ² is C _r C _{4 is} alkoxy, NH ₂ , d-C ₁ alkylamino or di-C ₁ -C ₄ alkylamino; and m is 0, 1, 2, 3, 4 or 5.

A further preferred embodiment of the invention relates to compounds in which R ¹ and R ² together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and another heteroatom from Group O, N and S as ring member and / or one or more substituents selected from the group consisting of halogen, G ₁ -C ₆ -alkyl, Gi-C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ - haloalkenyl, C ₁ -C ₆ -alkoxy, C-ι-C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy, C _r C ₆ alkylene, and Oxy-C _r C ₃ -alkylenoxy can carry. These compounds correspond in particular to formula 1.2,

wherein

D together with the nitrogen atom forms a five- or six-membered heterocyclyl or heteroaryl as defined above which is bonded via N and contains a further heteroatom from the group O, N and S as ring member and / or one or more substituents from the group halogen,

C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy and C _r C ₂ -haloalkyl;

R ³ and R ^{4 are} independently hydrogen or C 1 -C ₄ alkyl;

X is chlorine, methyl, cyano, methoxy or ethoxy;

L is halogen, cyano, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, a group C (S) A ² or a group C (O) A ² , where A ^{2 is} C _r C _4- alkoxy, NH ₂ ,

C 1 -C ₄ -alkylamino or di-C 1 -C ₄ -alkylamino; and m is 0, 1, 2, 3, 4 or 5.

Another preferred embodiment of the invention relates to compounds of the formula 1.3.

wherein

Y is hydrogen or C 1 -C ₄ -alkyl, in particular for methyl and ethyl,

R ³ and R ⁴ are independently hydrogen or C _r C ₄ alkyl;

X is chlorine, methyl, cyano, methoxy or ethoxy;

L is halogen, cyano, nitro, d-Ce-alkyl, d-Ce-haloalkyl, C ₁ -C ₆ -alkoxy, a

Group C (S) A ² or a group C (O) A ² , in which A ^{2 is} C _r C ₄ -alkoxy, NH ₂ ,

C-ι-C ₄ alkylamino or di-C ₁ -C ₄ -alkylamino; and m is 0, 1, 2, 3, 4 or 5. In particular, with regard to their use, the compounds I compiled in the following Tables 1 to 128 are preferred. In addition, the groups mentioned in Tables 1 to 128 for a substituent individually, independently of the combination in which they are mentioned, represent a particularly preferred embodiment of the substituent in question.

Table 1

Compounds each corresponding to the formula I, in which X is chlorine, L _n, 2-fluoro-6-chloro, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound to one row of Table A.

Table 2

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 3

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-dichloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 4

Compounds of the formula I ₁ in which X is chlorine, L _{m is} 2-fluoro-6-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 5

Compounds of the formula I in which X is chlorine, L _{m is} 2,4,6-trifluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 6

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-difluoro-4-methoxy, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 7

Compounds of the formula I in which X is chlorine, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each

Hydrogen and the combination of R ¹ and R ² for a compound of one line Table A corresponds.

Table 8

Compounds of the formula I in which X is chlorine, L _{m is} pentafluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 9

Compounds of the formula I in which X is chlorine, L _{m is} 2-methyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 10

Compounds of the formula I in which X is chlorine, L _{m is} 2-trifluoromethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 11

Compounds of the formula I in which X is chlorine, L _{m is} 2-methoxy-6-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 12

Compounds of the formula I in which X is chlorine, L _{m is} 2-chlorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 13

Compounds of the formula I in which X is chlorine, L _{m is} 2-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 14

Compounds of the formula I in which X is chlorine, L _{m is} 2,4-difluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 15

Compounds of the formula I in which X is chlorine, L _{m is} 2-fluoro-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 16

Compounds of the formula I in which X is chlorine, L _{m is} 2-chloro-4-fluorophenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 17

Compounds of the formula I in which X is chlorine, L _{m is} 2,3-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 18

Compounds of the formula I in which X is chlorine, L _{m is} 2,5-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 19

Compounds of the formula I in which X is chlorine, L _{m is} 2-methyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 20

Compounds of the formula I in which X is chlorine, L _{m is} 2,3,4-trifluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 21

Compounds of the formula I in which X is chlorine, 1- _m 2-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 22

Compounds of the formula I in which X is chlorine, L _{m is} 2,4-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 23

Compounds of the formula I in which X is chlorine, L _{m is} 2-methyl-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 24

Compounds of the formula I in which X is chlorine, L _{m is} 2-fluoro-4-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 25

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 26

Compounds of the formula I in which X is chlorine, L _{m is} 2,4,5-trimethylphenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 27

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-difluoro-4-cyano, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 28

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-difluoro-4-methyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 29

Compounds of the formula I in which X is chlorine, L _{m is} 2,6-difluoro-4-methoxycarbonyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 30

Compounds of the formula I in which X is chlorine, L _{m is} 2-trifluoromethyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 31

Compounds of the formula I ₁ in which X is chlorine, L _{m is} 2-trifluoromethyl-5-fluoro, R ^s and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound in each case corresponds to one line of Table A.

Table 32

Compounds of the formula I in which X is chlorine, L _{m is} 2-trifluoromethyl-5-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 33

Compounds of the formula I in which X is methyl, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 34

Compounds of the formula I in which X is methyl, L _{m is} 2,6-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 35

Compounds of the formula I in which X is methyl, L _{m is} 2,6-dichloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 36

Compounds of the formula I in which X is methyl, L _{m is} 2-fluoro-6-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 37

Compounds of the formula I, in which X is methyl, _m l_ 2,4,6-trifluoro, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds to one line of Table A.

Table 38

Compounds of the formula I in which X is methyl, L _{m is} 2,6-difluoro-4-methoxy, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 39

Compounds of the formula I in which X is methyl, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 40

Compounds of the formula I in which X is methyl, L _{m is} pentafluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 41

Compounds of the formula I in which X is methyl, L _{m is} 2-methyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 42

Compounds of formula I in which X ₁ is methyl, L _{m is} 2-trifluoromethyl, R ³ and R ⁴ each equal to hydrogen and the combination of R ¹ and R ² for a compound corresponds to one line of Table A.

Table 43

Compounds of the formula I in which X is methyl, L _{m is} 2-methoxy-6-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 44

Compounds of the formula I in which X is methyl, L _{m is} 2-chlorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 45

Compounds of the formula I in which X is methyl, L _{m is} 2-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 46

Compounds of the formula I in which X is methyl, L _{m is} 2,4-difluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 47

Compounds of the formula I in which X is methyl, L _{m is} 2-fluoro-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 48

Compounds of formula I in which X ₁ is methyl, L _m 2-chloro-4-fluorophenyl, R ³ and R ⁴ each respectively corresponds to hydrogen and the combination of R ¹ and R ² for a compound to one row of Table A.

Table 49

Compounds of the formula I in which X is methyl, L _{m is} 2,3-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 50

Compounds of the formula I in which X is methyl, L _{m is} 2,5-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 51

Compounds of the formula I in which X is methyl, L _{m is} 2-methyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 52

Compounds of the formula I in which X is methyl, L _{m is} 2,3,4-trifluorophenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 53

Compounds of the formula I in which X is methyl, L _{m is} 2-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 54

Compounds of the formula I in which X is methyl, L _{m is} 2,4-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 55

Compounds of the formula I in which X is methyl, L _n , 2-methyl-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line Table A corresponds.

Table 56

Compounds of the formula I in which X is methyl, L _{m is} 2-fluoro-4-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 57

Compounds of the formula I in which X is methyl, L _{m is} 2,6-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 58

Compounds of the formula I in which X is methyl, L _{m is} 2,4,5-trimethylphenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 59

Compounds of the formula I in which X is methyl, L _{m is} 2,6-difluoro-4-cyano, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 60

Compounds of the formula I in which X is methyl, L _{m is} 2,6-difluoro-4-methyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 61

Compounds of the formula I in which X is methyl, L _{m is} 2,6-difluoro-4-methoxycarbonyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 62

Compounds of the formula I in which X is methyl, L _{m is} 2-trifluoromethyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 63

Compounds of the formula I in which X is methyl, L _{m is} 2-trifluoromethyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound in each case corresponds to one line of Table A.

Table 64

Compounds of the formula I in which X is methyl, L _{m is} 2-trifluoromethyl-5-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 65

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 66

Compounds of the formula I in which X is methoxy, l_ _{m is} 2,6-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 67

Compounds of the formula I in which X is methoxy, l_ _{m is} 2,6-dichloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 68

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluoro-6-methyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 69

Compounds of the formula I in which X is methoxy, L _{m is} 2,4,6-trifluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 70

Compounds of the formula I in which X is methoxy, L _{m is} 2,6-difluoro-4-methoxy, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 71

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 72

Compounds of the formula I in which X is methoxy, L _{m is} pentafluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 73

Compounds of the formula I in which X is methoxy, L _{m is} 2-methyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 74

Compounds of the formula I in which X is methoxy, L_ _m 2-trifluoromethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 75

Compounds of the formula I in which X is methoxy, L _{m is} 2-methoxy-6-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 76

Compounds of the formula I in which X is methoxy, L _{m is} 2-chlorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 77

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 78

Compounds of the formula I in which X is methoxy, L _{m is} 2,4-difluorophenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 79

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluoro-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 80

Compounds of the formula I in which X is methoxy, L _{m is} 2-chloro-4-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 81

Compounds of the formula I in which X is methoxy, L_ _{m is} 2,3-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 82

Compounds of the formula I in which X is methoxy, L _{m is} 2,5-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 83

Compounds of the formula I in which X is methoxy, L _{m is} 2-methyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 84

Compounds of the formula I in which X is methoxy, l_ _{m is} 2,3,4-trifluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 85

Compounds of the formula I in which X is methoxy, L _{m is} 2-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 86

Compounds of the formula I in which X is methoxy, L _{m is} 2,4-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 87

Compounds of the formula I in which X is methoxy, L _{m is} 2-methyl-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 88

Compounds of the formula I in which X is methoxy, L _{m is} 2-fluoro-4-methyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 89

Compounds of the formula I in which X is methoxy, L _{m is} 2,6-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 90

Compounds of the formula I in which X is methoxy, L _{m is} 2,4,5-trimethylphenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 91

Compounds of the formula I in which X is methoxy, L _{m is} 2,6-difluoro-4-cyano, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 92

Compounds of the formula I in which X is methoxy, L _{m is} 2,6-difluoro-4-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 93

Compounds of the formula I in which X is methoxy, L _{m is} 2,6-difluoro-4-methoxycarbonyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 94

Compounds of the formula I in which X is methoxy, 1- _m 2-trifluoromethyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 95

Compounds of the formula I in which X is methoxy, L _{m is} 2-trifluoromethyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound in each case corresponds to one line of Table A.

Table 96

Compounds of the formula I in which X is methoxy, L _{m is} 2-trifluoromethyl-5-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 97

Compounds of the formula I in which X is cyano, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 98

Compounds of the formula I in which X is cyano, L _{m is} 2,6-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 99

Compounds of the formula I in which X is cyano, L _{m is} 2,6-dichloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 100

Compounds of the formula I in which X is cyano, L _{m is} 2-fluoro-6-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 101

Compounds of the formula I in which X is cyano, L _{m is} 2,4,6-trifluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 102

Compounds of the formula I in which X is cyano, L _{m is} 2,6-difluoro-4-methoxy, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 103

Compounds of the formula I in which X is cyano, L _{m is} 2-fluoro-6-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 104

Compounds of the formula I in which X is cyano, L _{m is} pentafluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 105

Compounds of the formula I in which X is cyano, L _{m is} 2-methyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 106

Compounds of the formula I in which X is cyano, L _{m is} 2-trifluoromethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 107

Compounds of the formula I in which X is cyano, L _{m is} 2-methoxy-6-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 108

Compounds of the formula I in which X is cyano., L _{m is} 2-chlorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 109

Compounds of the formula I in which X is cyano, L _{m is} 2-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 110

Compounds of formula I in which X ₁ is cyano, L _{m is} 2,4-difluorophenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 111

Compounds of the formula I in which X is cyano, L_ _{m is} 2-fluoro-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 112

Compounds of the formula I in which X is cyano, L _{m is} 2-chloro-4-fluorophenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 113

Compounds of the formula I in which X is cyano, L _{m is} 2,3-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 114

Compounds of the formula I in which X is cyano, L _{m is} 2,5-difluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 115

Compounds of the formula I in which X is cyano, L _{m is} 2-methyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 116

Compounds of the formula I in which X is cyano, L _{m is} 2,3,4-trifluorophenyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 117

Compounds of the formula I in which X is cyano, L _{m is} 2-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 118

Compounds of formula I in which X ₁ is cyano, L _{m is} 2,4-dimethyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 119

Compounds of the formula I in which X is cyano, L _{m is} 2-methyl-4-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound of one line in each case Table A corresponds.

Table 120

Compounds of the formula I in which X is cyano, L _{m is} 2-fluoro-4-methyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 121

Compounds of the formula I in which X is cyano, L _{m is} 2,6-dimethyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 122

Compounds of the formula I in which X is cyano, L _n , 2,4,5-trimethylphenyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 123

Compounds of the formula I in which X is cyano, L _{m is} 2,6-difluoro-4-cyano, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 124

Compounds of the formula I in which X is cyano, L _{m is} 2,6-difluoro-4-methyl, R ³ and R ⁴ are each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A. ,

Table 125

Compounds of the formula I in which X is cyano, L _{m is} 2,6-difluoro-4-methoxycarbonyl, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 126

Compounds of the formula I in which X is cyano, L _{m is} 2-trifluoromethyl-4-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table 127

Compounds of the formula I in which X is cyano, L _{m is} 2-trifluoromethyl-5-fluoro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ^{2 is} a compound in each case corresponds to one line of Table A.

Table 128

Compounds of the formula I in which X is cyano, L _{m is} 2-trifluoromethyl-5-chloro, R ³ and R ^{4 are} each hydrogen and the combination of R ¹ and R ² for a compound corresponds in each case to one row of Table A.

Table A

The compounds of the general formula I according to the invention can be obtained in various ways in analogy to prior art processes known per se according to the syntheses shown in the following schemes:

Compounds of the formula I in which X is Hal can be prepared, for example, as shown in Scheme 1. Scheme 1:

(IV) (I)

In Scheme 1, R ¹ , R ² and L _m are as defined above. R ³ and R ⁴ ste¬ hen independently hydrogen or optionally substituted C ₈ - alkyl. Hal and Hal 'independently represent halogen, preferably chlorine or bromine.

In a first step i), for example, a 5,7-Dihalogentriazolopyrimidin the general formula II with an organometallic compound of formula VI

Met ^y (CHR ³ R ⁴ ) _y (VI)

in which Met represents a metal atom or semimetal atom of valency y, such as B, Zn, Mg, Ti or Sn, and R ³ and R ^{4 are} independently hydrogen or optionally substituted C-ι-C ₈ alkyl, wherein to obtain a 7-alkyl-6-aryltriazolopyrimidine compound of general formula III. In one embodiment of this process, the reaction is carried out under transition metal catalysis, such as Ni or Pd catalysis. This reaction can be carried out, for example, by the following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), Ibid 1, 2345 (1996); WO-A 99/41255; Aust. J. Chem., Vol. 43, 733 (1990); J. Org. Chem., Vol. 43, 358 (1978); J. Chem. Soc. Chem. Commun. 866 (1979); Tetrahedron Lett, Vol. 34, 8267 (1993); ibid., Vol. 33, 413 (1992). In particular, when Met is Zn or Mg, the reaction can also be carried out without a catalyst. The compounds II are known, for example, from US Pat. No. 5,593,996, WO 94/20501, WO 98/46607 or WO 2004/041824.

The compounds of formula II are known in the literature (WO99 / 41255 or US 5,593,996) or can be prepared according to the cited literature.

The subsequent bromination of the 7-alkyl-6-aryltriazolopyrimidine compound of the general formula III in step ii) gives the 6-aryl-7- (bromoalkyl) -triazolopyrimidine

Compound of the general formula IV. Suitable brominating agents are, for example, N-bromoimides, such as N-bromosuccinimide, N-bromohydantoin, bromine or pyridinium tribromide. Depending on the brominating agent, the addition of a radical initiator, for example an organic peroxide such as dibenzoyl peroxide or an azo compound such as azobisisobutyronitrile or irradiation with light, may be advantageous for the course of the reaction. When using a free radical initiator, a catalytic amount is usually sufficient.

In general, the bromination takes place in the presence of a solvent. Suitable solvents are, for example, aliphatic or aromatic hydrocarbons which may also be halogenated, for example carbon tetrachloride, trichloromethane, dichloromethane, organic acids such as acetic acid, inorganic acids, pyridine, ethers such as tetrahydrofuran or dioxane, sulfides, sulfoxides, sulfones and mixtures thereof ,

The reaction temperature is usually between 10 ⁰ C and the boiling point of the solvent.

Subsequently, in a third step iii), the 7- (bromoalkyl) -6-aryltriazolopyrimidine compound of the general formula IV is reacted with an amine of the formula VII

^{H 1} V ( ^{v |} o

wherein R ¹ and R ^{2 have} the meanings given above.

This reaction is advantageously carried out at 0 to 70 ⁰ C, preferably 10 to 35 ⁰ C. Preferably, one works in an inert solvent. Suitable solvents include ethers such as dioxane, diethyl ether, methyl tertiary butyl ether or especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic Hydrocarbons such as toluene, xylene and the like, and mixtures thereof. [see. WO-A 98/46608].

The reaction may be carried out in the presence of a base of, for example, a tertiary amine such as triethylamine or an inorganic base, e.g. B. alkaline earth metal carbonates, Erdal- kalimetallhydrogencarbonate, alkali metal carbonates or alkali metal bicarbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate or cesium take place; Excess amine of the formula VII can also serve as a base.

The amines HNR ¹ R ² are generally commercially available or can be prepared by known methods.

The compounds of the formula III can also be obtained, for example, advantageously by reacting compounds II with a cyanide (step iv in Scheme 1) and subsequently reacting the resulting 7-cyano-5-halogeno-triazolopyrimidine V with a organometallic reagent ( Step v in Scheme 1).

In step iv), a 5,7-dihalo-triazolopyrimidine II is first reacted with a cyanide of the formula M-CN to give a 7-cyano-5-halo-triazolopyrimidine V. The cation M has little significance, but for practical reasons ammonium, tetramethylammonium or tetraethylammonium cyanide, transition metal cyanides such as zinc cyanide or alkali metal or alkaline earth metal cyanides are usually preferred. The reaction is preferably carried out in a solvent. Suitable solvents are ethers such as diethyl ether, methyl tert-butyl ether, dioxane or tetrahydrofuran, aromatic hydrocarbons such as toluene, carbonitriles such as acetonitrile or propionitrile and mixtures thereof. Usually, the reaction temperature is in the range of 0 to 120 ^° C., preferably 0 to 40 ^° C.

The 7-cyano-5-halo-triazolopyrimdin V thus obtained is subsequently reacted with an organo-metallic compound, for example a Grignard compound of the formula (CHR ³ R ⁴ ) -Mg-Hal or an organolithium compound of the formula (CHR ³ R ⁴ ) -Li, wherein R ³ and R ^{4 are} independently hydrogen or optionally substituted CrCs-alkyl and Hal is bromine or chlorine, reacted (step v). Usually, the reaction takes place in an organic solvent. Suitable organic solvents are ethers, such as diethyl ether, dibutyl ether,

Methyl tert-butyl ether, tetrahydrofuran, aromatic hydrocarbons such as toluene and mixtures thereof. If appropriate, it may be advantageous to carry out the reaction in the presence of catalytic or, in particular, at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts, such as Cu (I) halides, such as Cu (I) iodide perform. The reaction temperature is usually in a range of -100 to +100 ° C, preferably below 0 ⁰ C and in particular in the range of -20 to -78 ⁰ C.

Compounds of the formula I ₁ in which X is cyano, dC ₄ alkoxy or C _r C ₄ is halo-alkoxy, can also advantageous for the reaction of compounds I ₁ wo¬ rin X is halogen, preferably chlorine, with compounds M ¹ - X '(formula VIII) are obtained. Depending on the meaning of the group X 'to be introduced, compounds VIII represent an inorganic cyanide, an alkoxylate or a haloalkoxylate. The reaction is advantageously carried out in the presence of an inert solvent. The cation M ¹ in formula VIII has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred (Scheme 2).

Scheme 2:

(0 + ^■ IW-X ¹ * ~ (I)

(X = halogen) (VIII) {χ = χ- ₌ CN, C ₁ -C ₄ -alkoxy, C _r C ₄ -haloalkoxy}

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

Suitable solvents include ethers, such as dioxane, diethyl ether, methyl tert-butyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane or dichloroethane, aromatic hydrocarbons, such as toluene, and mixtures thereof.

Compounds of formula I in which X is dC ₄ alkyl, -C ₄ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₈ alkynyl, or C ₂ -C ₈ haloalkynyl may be prepared in an advantageous manner by reacting compounds I in which X is lied for Ha¬, with organometallic compounds X ^a -mt, wherein X ^a is C _r C ₄ alkyl, -C ₄ haloalkyl, C ₂ -C ₈ - Alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl or

C ₂ -C ₈ haloalkynyl and Mt for lithium, magnesium or zinc, wer¬ the produced. The reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (I) halides and especially Cu (I) iodide. In general, the reaction is carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents. The temperatures required for this purpose are in the range of -100 to + 10O ⁰ C and especially in the range of -80 ⁰ C to + 40 ⁰ C. Ver¬ drive this are known, for. B. from the cited prior art (see, for example, WO 03/004465)

In principle, compounds of the formula I in which X is C ₁ -C ₄ -alkyl can also be prepared by reacting compounds I in which X is halogen, in particular chlorine, with malonates of the formula IX. This synthetic route is shown in Scheme 3. In formula IX X "is hydrogen or C _r C ₃ alkyl and RC _r C ₄ alkyl. The compounds I are converted into compounds of the formula X, which anschlie¬ ßend after saponification be decarboxylated to give compounds I [cp. US 5,994,360] ,

Scheme 3:

(IX) (X) Δ / H ⁺

(X) (I) {X = X "= C ₁ -C ₄ -alkyl)

Malonates IX are known in the literature [J. At the. Chem. Soc., Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the cited literature.

The subsequent saponification of the ester X is carried out under generally customary conditions. Depending on the various structural elements, the alkaline or acidic saponification of the compounds X may be advantageous. Under the conditions of ester saponification, the decarboxylation to I can already take place completely or partially.

The decarboxylation is normally carried out at temperatures from 20 ⁰ C to 180 ⁰ C, preferably 50 ⁰ C to 120 ⁰ C, in an inert solvent, optionally in the Ge genwart an acid.

Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid. Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic Hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as Acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, be¬ particularly preferably the reaction in hydrochloric acid or acetic acid. It is also possible to use mixtures of the solvents mentioned.

Another synthetic route for compounds I in which X is C 1 -C ₄ -alkyl is shown in Scheme 4.

Scheme 4:

(I) {X = CVC ₄ -alkyl)

In Scheme 4, L _m , R ¹ , R ² , R and X "have the abovementioned meanings R ³ and R ⁴ independently of one another represent hydrogen or optionally substituted C 1 -C -alkyl With regard to the conversion of the compound IM with X = Hal in the compound IHA with X = X "= C _r C ₄ alkyl is fully on the in Scheme 2 With regard to the conversion of compounds of the formula I with X = Hal in compounds I with X = X "= C 1 -C ₄ -alkyl The same applies to step vi in Scheme 4 follows analogously to step ii) in Scheme 1. Step vii) is carried out analogously to step iii) in Scheme 1.

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

If individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I.

However, if isomer mixtures are obtained in the synthesis, separation is generally not necessary since the individual isomers interconvert in part during preparation for use or during use (for example under the action of light, acid or base) can. Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.

The compounds I are suitable as fungicides. They are distinguished by their excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Bassiomycetes. They are in part systemically effective and can be used in crop protection as foliar and soil fungicides.

They are of particular importance for the control of a large number of fungi on various crop plants such as wheat, rye, barley, oats, rice, maize, grass, plants, cotton, soya, coffee, sugar cane, wine, fruit and ornamental plants and Vegetable plants such as cucumbers, beans, tomatoes, potatoes and cucurbits, as well as the seeds of these plants.

In particular, they are suitable for controlling the following plant diseases:

* / 4 / temaria species on vegetables and fruits, • bipolaris and Drechslera cereals, rice and turf, • Blumeria graminis (powdery mildew) on cereals,

• Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines,

• Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,

• Fusarium and Verticillium species on various plants, • Mycosphaerella crops on cereals, bananas and peanuts,

• Phytophthora infestans on potatoes and tomatoes,

Plasmopara viticola on vines,

• Podosphaera leucotricha on apples,

• Pseudocercosporella herpotrichoides on wheat and barley, • Pseudoperonospora aften on hops and cucumbers,

• Puccinia Aύen on cereals,

Pyricularia oryzae on rice,

• Rhizoctonia species on cotton, rice and turf,

• Septoria tritici and Stagonospora nodorum on wheat, • Uncinυla necator on vines,

• Ustilago species on cereals and sugar cane, as well

• Venturia species (scab) on apples and pears.

The compounds I are also suitable for controlling harmful fungi such as Pecilomyces variotum material protection (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.

The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients. The application can be done both before and after the infection of the materials, plants or seeds by the fungi.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% active ingredient.

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

In the seed treatment, in general, amounts of active ingredient of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg are used.

When used in material or storage protection, the application rate of active ingredient depends on the type of application and the desired effect. Usual Wall quantities are in the material protection, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.

The compounds I can be converted into the customary formulations, for. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the respective purpose; In each case, it should ensure a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, for. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:

- water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures can also be used, carriers such as ground natural minerals (eg kaolins, clays, talc,

Chalk) and ground synthetic minerals (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.

The surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, tristearylphenyl polyglycol ethers, alkylarylpolyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene , Laurylalkoholpoly- glycol ether acetal, sorbitol esters, Ligninsulfitablaugen and methyl cellulose into consideration.

For the production of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin. crack, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, Me¬ ethanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, such. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

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

Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers are z. As mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium, fat, magnesium oxide, milled plastics, fertilizers such. For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and Nußschalenmehl, cellulose powder and other fes¬ te carriers.

The formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are: 1. Products for dilution in water

A Water Soluble Concentrates (SL)

10 parts by weight of a compound of the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other auxiliaries are added. When diluted in water, the active ingredient dissolves.

B Dispersible Concentrates (DC)

20 parts by weight of a compound of the invention in cyclohexanone with the addition of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water gives a dispersion.

C Emulsifiable Concentrates (EC)

15 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Dilution in water results in an emulsion. D emulsions (EW, EO)

40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced by means of an emulsifier (Ultraturax) in water and brought to a homogeneous emulsion. Dilution in water results in emulsification.

E suspensions (SC, OD)

20 parts by weight of a compound according to the invention are mixed with the addition of dispersants and wetting agents and water or an organic solvent in a

Agitator ball mill to a fine suspension of active ingredient crushed. Dilution in water results in a stable suspension of the active ingredient.

F Water-dispersible and Water-soluble Granules (WG, SG) 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersants and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient.

G Water-dispersible and Water-Soluble Powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of dispersants and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active substance.

2. Products for direct application

H dusts (DP) 5 parts by weight of a compound according to the invention are finely ground and intimately mixed with 95% finely divided kaolin. This gives a dust.

I Granules (GR ₁ FG, GG, MG)

0.5 parts by weight of a compound according to the invention are finely ground and combined with 95.5% excipients. Common methods are the extrusion, the

Spray drying or the fluidized bed. This gives a granulate for Direkt¬ application.

ULV solutions (UL) 10 parts by weight of a compound according to the invention are dissolved in an organic compound Solvent, for. B. XyIoI solved. This gives a product for Direktapplika¬ tion.

The active compounds can be used as such, in the form of their formulations or the application forms prepared therefrom, eg. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied. The forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare from effective substance wetting agents, adhesives, dispersants or emulsifiers and any concentrates which are solvent or oil, which are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.

To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1:10 to 10: 1.

The agents according to the invention can also be present in the application form as fungicides zu¬ together with other active ingredients, the z. As with herbicides, insecticides, growth regulators, fungicides or with fertilizers. When mixing the compounds I or the agents containing them in the application form as fungicides with other fungicides is obtained in many cases, an enlargement of the fungicidal spectrum of activity. The following list of fungicides with which the compounds according to the invention can be used together is intended to illustrate, but not limit, the possible combinations.

Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl;

Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph;

Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl; • antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin;

• Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazole, prothioconazole, tebuconazole, triadimefon, triadimol, triflumizole , Triticonazole;

Dicarboximides such as iprodione, myclozoline, procymidone, vinclozolin;

Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamate, Thiram, Ziram, Zineb;

Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxaldine, oxycarboxine, cyazofamide, dazomet, dithianone, famoxadone, fenamidone,

Fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazide, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabenazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole, triforine;

Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate;

Nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone, nitrophthalic-isopropyl;

Phenylpyrroles such as fenpiclonil or fludioxonil;

• sulfur;

Other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chloroboronil, cyflufenamid, cymoxanil, diclomethine, diclocymet, diethofencarb, edfenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, ferimzone, fluaziamine, fosetyl, Fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pentycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide;

Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin;

Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid;

Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph. synthesis Examples

The instructions given in the Synthesis Examples below were used with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are listed in the following Table B with physical information.

Example 1: 5-Chloro-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine and 5- (4-methylpiperidin-1-yl) -7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1, 5-a] pyrimidine

1.1 5-Chloro-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine-7-carbonitrile

To a solution of 5,7-dichloro-6- (2,4,6-trifluorophenyl) - [1, 2,4] -triazolo [1,5-a] pyrimidine (62.7 mmol) cooled to 0 ° C. [see. WO 98/46607] in 300 ml of acetonitrile was added, with stirring, within 15 minutes, a solution of 1.1 equivalents of tetraethylammonium cyanide in 50 ml of acetonitrile. The reaction mixture rühr¬ te one hour at 0 ⁰ C and then left within two hours Raum¬ warm temperature.

After concentrating the reaction mixture to dryness, the solid residue obtained was taken up in ethyl acetate. It was filtered from the insoluble (tetraethylammonium chloride). The resulting clear solution was washed three times each with 5% aqueous citric acid, saturated sodium bicarbonate solution and brine. The organic phase was dried over water-free Na ₂ SO ₄ , filtered and concentrated to dryness. The title compound was obtained in 94% yield. The title compound obtained was used without further purification in the next step.

1.2 5-Chloro-7-methyl-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine

In an inertized with argon three-necked flask, tetrahydrofuran and cooled in a dry ice / acetone bath to -60 ⁰ C. Then was added via a dropping funnel 13.4 mmol (3 equivalents) of methyl magnesium chloride in tetrahydrofuran are added and rinsed the dropping funnel with a few milliliters of tetrahydrofuran to.

Thereafter, at a flask inside temperature of not more than -50 ⁰ C was added dropwise a solution of 5-chloro-6- (2,4,6-trifluorophenyl) [1, 2,4] triazolo [1, 5-a] pyrimidine-7-carbonitrile (4.5 mmol) from Example 1.1 in tetrahydrofuran and stirred for 1 hour at this temperature, the reaction was controlled by means of HPLC / MSD. Thereafter, the reaction mixture was poured onto a saturated ammonium chloride solution. To the aqueous reaction mixture was added diethyl ether, the aqueous reaction mixture extracted, and the aqueous phase was washed once with diethyl ether. The combined organic phases were washed twice with

5% aqueous citric acid, twice with a saturated sodium bicarbonate solution and then once with a saturated saline solution. The organic phase was dried over magnesium sulfate, filtered from the drying agent and concentrated to dryness to give the title compound in 87% yield. The title compound was used in the next without further purification

Reaction step used.

1.3 7-Bromomethyl-5-chloro-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine

5 To a solution of 5-chloro-7-methyl-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine (40 mmol) from Example 1.2 in 600 ml Tetrahydrofuran was added 1.2 equivalents of pyridinium tribromide and 1.2 equivalents of pyridine. Stirring the mixture Re¬ action for 5 days at 55 ⁰ C.

After concentrating the reaction mixture, the obtained solid was taken

Residue in ethyl acetate on. It was washed twice with 5% aqueous citric acid and twice with saturated brine. After drying over magnesium sulphate, the desiccant was removed and concentrated. From the residue obtained, after chromatography on silica gel (eluting agent: ethyl acetate / cyclohexane 1: 2), the title compound in

55% yield.

1.4 5-Chloro-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine and 5- (4-Methylpiperidin-1-yl) -7- (4-methylpiperidin-1-yl-0-methyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1, 5 -a] pyrimidine

To a solution of 7-bromomethyl-5-chloro-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine (0.4 mmol) from Example 1.3 in dichloromethane was added 1.2 equivalents of triethylamine and 1 equivalent of 4-methylpiperidine. The resulting reaction mixture was stirred for 15 hours at room temperature.

Then, dilute hydrochloric acid was added to the reaction mixture, the phases were separated and the organic phase was extracted with a dilute sodium chloride solution. The organic phase was concentrated and the residue was purified by means of preparative HPLC on silica gel RP-18 (Chromolith Speed ROD of Merck KGaA, Germany, 40 ⁰ C; Eluent: acetonitrile with 0.1% by volume of trifluoroacetic acid and 0.1% by volume of trifluoroacetic acid / water mixture, the ratio trifluoroacetic acid / water being changed within 5 minutes from 5:95 to 95: 5). 5-Chloro-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine was obtained in 60% iger yield and

5- (4-methylpiperidin-1-yl) -7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5] a] pyrimidine in 53% yield

Example 2 Preparation of 5-methyl-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine ( Production route A)

2.1 A 2- [7- (4-methylpiperidin-1-ylmethyl) -6- (2, 4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-5- yl] malonate

24 equivalents of dimethyl malonate were placed in a reaction vessel, 6

Equivalent sodium hydride and 4 Ä molecular sieve before and diluted with acetonitrile. Thereafter, it was rendered inert with argon gas, the mixture was stirred until completion of the evolution of hydrogen gas, and 5-chloro-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1, 2,4] triazolo [1,5-a] pyrimidine (0.23 mmol) from Example 1. Stirring the reaction mixture 4 hours at 90 ⁰ C. Thereafter zentrif ugierte the reaction mixture at 4000 U / min for 10 minutes at 0 ⁰ C.

After decanting and concentrating the solution, the resulting residue was taken up in dichloromethane and 0.1 N hydrochloric acid was added. The phases were separated, the organic phase was washed with water, dried over sodium sulfate and concentrated to give the title compound in 78% yield. The title compound was used in the next step without further purification.

2.2A 5-Methyl-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine

A solution of 2- [7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine was obtained. 5-yl] -malonic acid dimethyl ester (0.15 mmol) from Example 2.1A in concentrated hydrochloric acid for 1 hour at 80 ° C.

After cooling, the reaction mixture was concentrated and the solid obtained was taken up in dichloromethane. The mixture was extracted twice with saturated sodium bicarbonate solution and twice with water. The or¬ ganic phase was dried over sodium sulfate, the desiccant filtered off and concentrated to give the title compound in 83% yield. Manufacturing route B:

2.1 B 2- [7-Methyl-6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidin-5-yl] - malonate

24 equivalents of dimethyl malonate, 6 equivalents of sodium hydride and 4 Å molecular sieves were placed in a reaction vessel and then diluted with acetonitrile. Thereafter, it was inert with argon gas, the mixture was stirred until the evolution of hydrogen gas ceased, and then 5-chloro-7-methyl-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a ] pyrimidine (2.68 mmol) from Example 1.2. The reaction mixture was stirred at 90 ^° C. for 3 hours.

The reaction mixture was filtered and the precipitate was washed with acetonitrile. The resulting solution was concentrated, the residue taken up in dichloromethane and 0.1N hydrochloric acid added. After phase separation, the organic phase was washed with water, dried over sodium sulfate and concentrated to give the Ti¬ telverbindung in 82% yield. The title compound was used without further purification in the next step.

2.2B 5,7-dimethyl-6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine

A solution of 2- [7-methyl-6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidin-5-yl] -malonic acid dimethacrylate (2; 03 mmol) from Example 2.1 B in concentrated hydrochloric acid for 1 hour at 80 ⁰ C.

After cooling, the reaction mixture was concentrated and the solid obtained was taken up in dichloromethane. The mixture was extracted twice with saturated sodium bicarbonate solution and twice with water. The organic phase was dried over sodium sulfate, the desiccant filtered off and concentrated to give the title compound in 79% yield.

2.3B 7-Bromomethyl-5-methyl-6- (2 _l, 4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine and 5-chloro-7-dibromomethyl-6- ( 2,4,6-trifluorophenyl) - [1 ₎ 2,4] triazolo [1,5-a] pyrimidine

To a solution of 5,7-dimethyl-6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (2 mmol) from Example 2.2B in 25 ml of tetrahydrofuran One gave 1.2 equivalents of pyridine and 1.25 equivalents of pyridinium tribromide. The reaction mixture was stirred at 55 ^° C. for 4 days. After cooling the reaction mixture was poured into ethyl acetate (250 ml) and extracted 3-4 times with 50 ml of saturated saline solution. The combined organic extracts were dried over calcium chloride. After filtering off the desiccant, the solvent was removed. The resulting oil was applied to 8 g of silica gel and then purified over an 80 g Kiesel¬ gel column (eluent: ethyl acetate / cyclohexane (1/1)). There was obtained 7-bromomethyl-5-methyl-6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine (30.3% yield, based on the compound from Example 2.2B) and 5-chloro-7-dibromomethyl-6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (12.9% yield, relative to on compound from Example 2.2B).

2.4B 5-Methyl-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine

To a solution of 7-bromomethyl-5-methyl-6- (2,4,6-trifluorophenyl) -

[1,2,4] triazolo [1,5-a] pyrimidine (0.10 mmol) from Example 2.3B in dichloromethane was added with 1.1 equivalents of triethylamine and 1.1 equivalents of 4-methylpiperidine. Thereafter, the reaction mixture was stirred for 12 hours at room temperature.

After washing the reaction mixture twice with dilute sodium chloride solution and drying, the solvent was removed, the title compound being obtained in 74% yield.

Example 3: Preparation of 5-Methoxy-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyrirnidine

To a solution of 50 mg (0.12 mmol) of 5-chloro-7- (4-methylpiperidin-1-ylmethyl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1 5-a] pyrimidine from Example 1 in 2 ml of methanol was added 8 mg (0.14 mmol) of sodium methylate. Thereafter, the reaction mixture was shaken for 3 hours at room temperature.

After concentrating the reaction mixture, the resulting residue was taken up in dichloromethane. The mixture was extracted once each with dilute aqueous hydrochloric acid and water. The organic phase was dried and the solvent removed, yielding 47 mg (0.11 mmol) of the title compound

(92% of the theoretical yield). According to HPLC-MS, the purity was 90%.

According to the rules given here, the compounds of general formula I indicated in Table B below were prepared. All products were characterized by combined HPLC / mass spectrometry (High Performance Liquid Chromatography Mass Spectrometry). For HPLC, an analytic RP-18 column (Chromolith Speed ROD of Fa. Merck KGaA, Deutsch¬ country), which was operated at 40 ⁰ C. The eluent used was acetonitrile with 0.1% by volume of trifluoroacetic acid / water mixture and 0.1% by volume of trifluoroacetic acid. (The ratio of trifluoroacetic acid / water was changed from 5:95 to 95: 5 in 5 minutes). Mass spectrometry was carried out by means of a quadrupole mass spectrometer with electrospray ionization at 80V in the positive mode.

Table B:

= 2, 4,6-trifluoro}

1) Retention time in HPLC analysis in minutes

2) m / z of the [M + H] ⁺ peak

Examples of the effect against harmful fungi

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

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

Use Example 1 Efficacy Against Tomato Drought Damage Caused by Alternaria solani

Leaves of potted plants of the "golden queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below. On the following day, the leaves were infected with an aqueous spore suspension of Alternaria solani \ n 2% biomalt solution with a density of 0.17 × 10 ⁶ spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ⁰ C. After 5 days had become the disease on the untreated but infected control plants developed so strongly that the infection could be determined visually in%.

In this test, the plants treated with 250 ppm of the compound from Examples 1a, 24, 25 or 26 showed a maximum of 10% infestation, while the untreated plants were 90% infected.

Use Example 2 Efficacy Against Gray Mold on Paprika Leaves Produced by Botrytis cinerea in Protective Application

Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below, after 2 to 3 leaves had developed well. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 × 10 ⁶ spores / ml in a 2% aqueous biomalt solution. Subsequently, the test plants were placed in a climatic chamber with 22 to 24 ⁰ C, darkness and high humidity. After 5 days, the extent of fungal infection on the leaves could be determined visually in%.

In this test, the plants treated with 250 ppm of the compound from Example 24, 25, 26 or 29 showed a maximum of 15% infestation, while the untreated plants were 90% infected.

Claims

claims

1. 7-Aminomethyl-1,2,4-triazolo [1. , 5-a] pyrimidine Verbndungen the general

Formula I

wherein the subscript m and the substituents R ¹ , R ² , R ³ , R ⁴ , X and L have the following meanings:

R ¹ , R ² independently of one another are hydrogen, C 1 -C ₈ -alkyl,

C ₁ -C 4 haloalkyl, C ₁ -C ₈ alkoxy, C ₃ -C ₈ cycloalkyl, C ₅ -C ₁₀ bicycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₂ -C ₈ alkenyl, C ₄ -C ₁₀ alkadienyl, C C ₂ -C ₈ -haloalkenyl, C ₃ -C ₆ -cycloalkenyl, C ₃ -C ₆ -halocycloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated , partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N or S,

R ¹ and R ² may also together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and one, two or three further heteroatoms from the group O, N and S as ring member and / or one or more substituents from the group halogen, CrCβ-alkyl, -C ₆ haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ haloalkenyl, C _r C ₆ - alkoxy,

Ci-C ₆ alkoxycarbonyl, -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy can wear and / or wherein two groups bonded to adjacent ring atoms substituents for Ci-Ce-alkylene, oxy-C ₂ -C ₄ -alkyl or OXy-C ₁ -C ₃ alkyleneoxy;

R ¹ and / or R ² may carry one, two, three or four identical or different groups R ^a :

R ^{a is} halogen, cyano, nitro, hydroxy, carboxyl, CRCE alkyl, CRCE haloalkyl, C _r C ₆ alkylcarbonyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, -C ₆ haloalkoxy, CRCE-alkoxycarbonyl, Ci-C ₆ alkylthio, -C ₆ alkylamino, di-CrC ₆ alkylamino, d-Cβ-alkylaminocarbonyl, di-CrCβ-alkylaminocarbonyl, C ₂ - C ₈ alkenyl, C ₄ -C 10 alkadienyl, C ₂ -C ₈ -haloalkenyl, C ₃ -C ₈ -cycloalkenyl, C ₂ -C ₆ -alkenyloxy, C ₃ -C ₆ -haloalkenyloxy,

C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl, C ₃ -C ₆ -alkynyloxy, C ₃ -C ₆ -haloalkynyloxy, C ₃ -C ₆ -cycloalkoxy, C ₃ -C ₆ -cycloalkenyloxy, oxyalkylene C 1 -C ₃ -alkyleneoxy, phenyl, naphthyl, five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O. , N or S,

in which the aliphatic, alicyclic or aromatic groups in R ^{a may} themselves be partially or completely halogenated or may carry one, two or three groups R ^b :

R ^{b is} halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkadienyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkyl- sulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the said alkenyl, alkadienyl or alkynyl groups in these radicals 2 to

Contain 8 carbon atoms;

and / or one, two or three of the following radicals:

Cycloalkyl, bicycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; Aryl, aryloxy, arylthio, AlyI-C ₁ -C ₆ alkoxy, aryl-CrC ₆ alkyl, hetaryl, hetaryloxy, hetarylthio, wherein the aryl radicals preferably 6, 7, 8, 9 or 10 ring members, the hetaryl 5 or 6 ring members, wherein the cyclic systems may be partially or completely halogenated or substituted by alkyl or haloalkyl groups;

R ^3, R ⁴ are independently hydrogen, Ci-C ₈ alkyl, d-Cβ-haloalkyl, CrC ₈ -HaIogenalkoxy, -C ₈ alkoxy, C-rCs-haloalkoxy or Ci-C ₈ alkoxy-C-rC ₈ alkyl, wherein the 6 last-mentioned radicals may carry one, two, three or four identical or different radicals R ^c , wherein R ^{0 is} the one given for R ^a Has meanings;

X is halogen, cyano, 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle containing 1, 2 or 3 heteroatoms from the group O, N or S as ring member, CτC ₄ alkyl, C ₁ -C ₄ -alkoxy, C ₂ -C ₈ alkenyl or C ₂ -C ₈ alkynyl, where the four last-mentioned radicals may be partially or completely halogenated and / or one, two or three substituents selected from nitro, cyano, C ₁ -C ₂ -Alkoxy, C _r C ₄ alkoxycarbonyl, amino, C _r C ₄ alkylamino and di-CrC ₄ alkylamino, and the 5- or 6-membered heterocycle one or more substituents selected from the group halogen, C ₁ -C ₆ -alkyl, -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C _r C ₆ alkoxy, C-ι-C ₆ alkoxycarbonyl, dC ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy, (exo) -CrC ₆ alkylene and OXy-C ₁ -C ₃ alkyleneoxy;

L is halo, cyano, hydroxy, cyanato (OCN), nitro, C _r C ₈ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, -C ₆ haloalkyl, C ₂ -C ₁₀ haloalkenyl,

C ₁ -C ₆ -alkoxy, C ₂ -C ₁₀ - AI kenyloxy, C ₂ -C ₁₀ alkynyloxy, C _r C ₆ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C 6 cycloalkenyl, C ₃ - C ₆ -Cycloalkoxy, C ₁ -C ₁₀ -alkoxycarbonyl, C ₂ -C ₁₀ -alkenyloxycarbonyl, C ₂ -C ₁₀ -alkynyloxycarbonyl, aminocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, di (C ₁ -C ₈ ) -alkylaminocarbonyl, C ₁ -C ₈ -alkoximinoalkyl,

C ₂ -C ₁₀ alkenyloximinocarbonyl, C ₂ -C ₁₀ alkynyloximinoalkyl, C ₁ -C ₈ alkylcarbonyl, C ₂ -C ₁₀ alkenylcarbonyl, C ₂ -C ₁₀ alkynylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, a fifth -, six-, seven-, eight-nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O,

N or S, amino, NR ⁵ R ⁶ , NR ⁵ - (C = O) -R ⁶ , S (= O) _n A ¹ , C (= O) A ² , C (= S) A ² , a group -C (S) NR ⁷ R ⁸ , a group -C (= N-OR ⁹ ) (NR ¹⁰ R ¹¹ ) or, a group -C (= N-NR ¹² R ¹³ ) (NR ¹⁴ R ¹⁵ ),

wherein

R ⁵ , R ^{6 are} independently selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ -cycloalkenyl , where the 5 last-mentioned radicals can be partially or completely halogenated or one, two, three or four radicals te selected from cyano, C ₁ -C ₄ -alkoximino, C ₂ -C ₄ -alkenyloximino, C ₂ -C ₄ -alkynyloximino or C ₁ -C ₄ -alkoxy may carry;

A ¹ represents hydrogen, hydroxy, -C ₈ alkyl, CRCS alkylamino or di- (C ₁ -C ₈ alkyl) amino;

n is 0, 1 or 2;

A ^{2 is} C ₂ -C ₈ alkenyl, C ₁ -C ₈ alkoxy, C ₁ -C ₆ haloalkoxy, amino or one of the groups mentioned for A ¹ ;

R ^7, R ^8, R ^9, R ^10, R ^11, R ^12, R ^13, R ¹⁴ and R ¹⁵ are independently selected ausge¬ from hydrogen, Ci-C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, where the four last-mentioned radicals may have one, two, three, four, five or six radicals R ^a ; or

R ⁷ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹² and R ¹³ and / or R ¹⁴ and R ¹⁵ together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which can carry one, two, three or four independently selected substituents from R ^a ;

m is 0, 1, 2, 3, 4 or 5;

and the agriculturally acceptable salts of the compounds I.

2. Compounds of general formula I according to claim 1, wherein at least ei¬ ner of the radicals R ¹ or R ^{2 is} different from hydrogen.

3. Compounds of general formula I according to claim 1 or 2, wherein R ³ and R ⁴ are independently hydrogen, CVC ₄ alkyl or C ₁ -C ₄ -alkoxy are.

4. Compounds of general formula I according to claim 3, wherein at least ei¬ ner of the radicals R ³ or R ^{4 is} hydrogen.

5. Compounds of general formula I according to any one of the preceding claims An¬ wherein X is halogen, cyano, C ₁ -C ₄ -AIk ^, -C ₄ haloalkyl, C ₁ -G ₄ -alkoxy or CRCA haloalkoxy.

6. Compounds of general formula I according to claim 5, wherein X is halogen.

7. Compounds of general formula I according to any one of the preceding claims arrival, wherein m is 1, 2, 3 or 4 and L is selected from halogen, Cy ano, nitro, -C ₆ alkyl, dC ₆ haloalkyl, C ₁ -C ₆ -alkoxy, a group C (S) A ² or a group C (O) A ² .

8. Compounds of general formula I according to claim 7, wherein the substituted by L _m phenyl group for the group C

where # is the site of attachment to the triazolopyrimidine skeleton and

L ^{1 is} fluorine, chlorine, trifluoromethyl or methyl;

L ^{2 is} hydrogen, chlorine or fluorine;

L ^{3 is} hydrogen, CN, nitro, fluorine, chlorine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, a group C (S) A ^2a or a group C (O) A ^2a , where A ^2a is C ₁ -C ₄ -alkoxy, NH _2, -C ₄ alkylamino or di-C ₁ -C ₄ alkylamino; L ^{4 is} hydrogen, chlorine or fluorine; and

L ^{5 represents} hydrogen, fluorine, chlorine or C 1 -C ₄ -alkyl.

9. Use of compounds of the general formula I according to any one of An¬ claims 1 to 8 and of their agriculturally acceptable salts for combating pathogenic fungi fungi.

10. A composition for controlling pathogenic fungi, comprising at least one compound of general formula I according to any one of claims 1 to 8 and / or an agriculturally acceptable salt of I and at least one solid or liquid carrier.

11. A method for controlling fungi pathogenic fungi, characterized gekenn¬ characterized in that the fungi or to be protected from fungal attack materials, plants, the soil or seeds with an effective amount of at least one compound of general formula I according to any one of claims 1 treated to 8 and / or an agriculturally acceptable salt of I.