WO2005113555A1 - Triazolopyrimidine compounds and their use for controlling pathogenic fungi - Google Patents

Abstract

The invention relates to novel triazolopyrimidine compounds of general formula (I), to their use for controlling pathogenic fungi and to agricultural pesticides containing compounds of this type as active constituents. In formula (I), X, Y, L, m, Ar and A are defined as follows: X represents halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; Y represents halogen, C1-C4 alkyl or C1-C4 haloalkyl; L represents independently of one another halogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, nitro, amino, NHR, NR2, cyano, S(=O)nA1 or C(=O)A2; m represents 0, 1, 2, 3 or 4; A stands for a chemical bond or a CR4R5 group; Ar represents phenyl or a 5- or 6-membered heteroaromatic group comprising 1, 2 or 3 heteroatoms selected from O, S and N as ring members, whereby the phenyl and the heteroaromatic group can comprise a fused benzole ring and can have 1, 2, 3, 4 or 5 Ra substituents. R1 to R3 are defined as cited in claim 1.

Description

Triazolopyrimidine compounds and their use in combating harmful fungi

description

The present invention relates to new triazolopyrimidine compounds and their use for combating harmful fungi and crop protection agents which contain such compounds as an active ingredient.

EP-A 71792, US 5,994,360, WO-A 94/20501, EP-A 834 513, WO-A 98/46608 and WO 03/080615 describe fungicidally active triazolo [1, 5a] pyrimidines which are in the 6-position of the azolopyrimidine ring carry an optionally substituted phenyl group and in the 7-position NH ₂ or a primary or secondary amino group.

GB 2355261 discloses fungicidally active triazolo [1, 5a] pyrimidines of the type mentioned above, which carry an arylamino group in the 7-position.

EP-A 550 113 describes fungicidally active triazolo [1,5a] pyrimidines which can have an alkylamino group in the 7-position, in which the alkyl group can have, inter alia, a phenyl ring.

The triazolopyrimidines known from the prior art with an amino group in the 7-position are sometimes unsatisfactory in terms of their fungicidal activity or have undesirable properties, such as low crop plant tolerance.

The present invention is therefore based on the object of providing new compounds with better fungicidal activity and / or better crop tolerance.

This object is surprisingly achieved by triazolopyrimidine compounds of the general formula I.

wherein:

X represents halogen, cyano, dC ₄ alkyl, dd haloalkyl, CC ₄ alkoxy or dC ₄ haloalkoxy;

Y represents halogen, dC ₄ alkyl or dC ₄ haloalkyl;

L independently of one another halogen, dC ₆ -alkyl, C ₂ -C ₆ -alkenyl, dC ₆ - haloalkyl, -C-C ₆ -alkoxy, CC ₆ -haloalkoxy, nitro, amino, NHR, NR ₂ , cyano, S (= O ) _n mean A ¹ or C (= O) A ² , wherein

R independently of one another are Ci-Cβ-alkyl or dC ₈ -alkylcarbonyl;

A ¹ for hydrogen, hydroxy, dC ₈ alkyl, dC ₈ alkylamino or di- (dC ₈ alkyl) amino n for 0, 1 or 2;

A ^{2 represents} C ₂ -C ₈ alkenyl, dC ₈ alkoxy, dC ₆ haloalkoxy or one of the groups mentioned in A ¹ ;

m represents 0, 1, 2, 3 or 4;

A represents a chemical bond or a group CR ⁴ R ⁵ ;

Ar represents phenyl or a 5- or 6-membered heteroaromatic radical which has 1, 2 or 3 heteroatoms selected from O, S and N as ring members, in which phenyl and the heteroaromatic radical can have a fused-on benzene ring and 1, 2, 3 , May have 4 or 5 substituents R ^a , which are halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₄ -alkyl, dC ₄ -haloalkyl, CC ₄ -alkoxy, dC ₄ - haloalkoxy, dC ₄ -alkylthio, CC ₄ -alkylamino, dC ₄ -dialkylamino, dC ₄ - alkylcarbonyl, dC ₄ -alkylsulfonyl, dC ₄ -alkylsulfinyl, CC ₄ -alkoxycarbonyl, CC -alkylcarbonyloxy, dC ₄ -alkylaminylcarbon ₄ -dialkylaminocarbonyl are selected, where two groups R ^a bonded to adjacent C atoms can also represent C ₃ -C ₅ alkylene, in which one or 2 non-adjacent C atoms can be replaced by oxygen or sulfur;

R ^{1 is} hydrogen, dC ₈ alkyl, which may have a radical R ^b , CC ₈ haloalkyl, or C ₃ -C ₆ cycloalkyl, which may be partially or completely halogenated and may optionally have 1, 2, 3 or 4 CC ₄ alkyl groups, means formyl, d- C ₈ alkylcarbonyl or CC ₈ alkoxycarbonyl, where R ^{b is} OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , COOR ¹⁰ , CONR ¹¹ R ¹² , CN, NHC (= NR ¹³ ) NR ¹¹ R ¹² , C ₃ -C ₆ cycloalkyl or phenyl, which optionally carries 1, 2, 3, 4 or 5 substituents R ^a ; or with R ² or with a radical R ^a which is arranged in the ortho position to the group CR ² R ³ , stands for C ₂ -C -alkylene which optionally 1, 2, 3 or 4 CC ₄ - alkyl groups and / or can carry 1 or 2 radicals R ^c , where R ^{c is} halogen, OH, dC ₄ -alkoxy or dC ₄ -alkoxycarbonyl;

R ^{2 is} hydrogen, dC ₄ -alkyl, which may have a radical R ^d , dC ₄ -haloalkyl, or C ₃ -C ₆ -cycloalkyl, which may be partially or completely halogenated and optionally 1, 2, 3 or 4 dd- Can carry alkyl groups means; where R ^{d is} OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , NHC (= NR ¹³ ) NR ¹¹ R ¹² , C ₃ -C ₆ cycloalkyl or phenyl, which may have 1, 2, 3, 4 or 5 substituents R ^a bears, stands or with a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , stands for C ₂ -C ₄ -alkylene which optionally 1, 2, 3 or 4 dC ₄ -alkyl groups and / or can carry 1 or 2 radicals R ^c ;

R ^{3 is} hydrogen or dC ₄ alkyl or together with R ^{2 is} C ₂ -C ₆ alkylene, in which 1 C atom can be replaced by an oxygen atom or a sulfur atom and, if appropriate, 1, 2, 3 or 4 CC Can carry ₄ alkyl groups and / or 1 or 2 radicals R ^c ;

R ⁴ , R ⁵ independently of one another represent hydrogen or dC ₈ -alkyl;

R ^{6 represents} hydrogen, dC ₈ alkyl, formyl or dC ₈ alkyl carbonyl;

R ^{7 represents} hydrogen or dC ₈ alkyl;

R ⁸ , R ⁹ independently of one another are hydrogen, -CC ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - cycloalkyl-dC ₄ -alkyl or together with the nitrogen atom to which they are attached, form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from O, S and N as a ring member and which bears 1, 2, 3 or 4 CC ₄ -alkyl groups, where one of the radicals R ⁸ or R ^{9 can} also represent formyl, dC ₈ -alkylcarbonyl or d- C ₈ -alkylthiocarbonyl; R ^{10 represents} H, d-Cβ-alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₆ cycloalkyl, phenyl or phenyl-dC ₄ -alkyl;

R ¹¹ , R ¹² independently of one another are hydrogen, dC ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - cycloalkyl-dC ₄ -alkyl, or together with the nitrogen atom to which they are attached are one form saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from O, S and N as the ring member and which bears 1, 2, 3 or 4 dC ₄ alkyl groups; and

R ^{13 represents} hydrogen, CC ₈ alkyl or CC ₈ alkoxy;

and by the agriculturally acceptable salts of the compounds I.

The present invention thus relates to the triazolopyrimidine compounds of the general formula I and their agriculturally acceptable salts.

The present invention furthermore relates to the use of the triazolopyrimidine compounds of the general formula I, their tautomers and their agriculturally acceptable salts for controlling phytopathogenic fungi (= harmful fungi) and a process for combating phytopathogenic harmful fungi, which is characterized in that the Fungi, or the materials, plants, the soil or seeds to be protected against fungal attack, are treated with an effective amount of a compound of the general formula I, a tautomer of I and / or with an agriculturally acceptable salt of I or its tautomer.

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

Depending on the substitution pattern, the compounds of the formula I and their tautomers can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.

Agriculturally useful salts include, in particular, 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. The ions of the alkali metals, in particular preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which, if desired, carry one to four dC ₄ alkyl substituents and / or a phenyl or benzyl substituent may, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, further phosphonium ions, sulfonium ions, preferably tri (dC ₄ alkyl) suιfonium and sulfoxonium ions, preferably tri (dC 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, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, as well as the anions of dC ₄ -alkanoic acids, preferably formate, preferably formate Propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

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

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl and all alkyl parts in alkoxy, alkylcarbonyl, alkylcarbonyloxy, alkylthio, alkylsulfonyl, alkylsulfinyl, alkoxyalkyl, alkoxyalkoxy, alkoxycarbonyl, alkylamino and dialkylamino, alkylaminocarbonyl and dialkylaminocarbonyl: saturated, straight-chain or branched hydrocarbon radicals with 1 to 4 or 6 to 6 to 6 up to 10 carbon atoms, for example dC 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-trimethyl propyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Alkylene: a linear divalent hydrocarbon radical with 1, 2, 3 or 4 CH ₂ groups, in which 1, 2, 3 or 4 H atoms can be substituted by alkyl and / or 1 or 2 H atoms by a group R ^c such as can be replaced as defined above; Halo (gen) alkyl: straight-chain or branched alkyl groups with 1 to 4 or to 6 carbon atoms (as mentioned above), in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example dC 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 and 1, 1, 1-trifluoroprop-2-yl;

Alkenyl: monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, to 6, to 8 or 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-pentene yl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4- _, pentenyl, 4-methyl-4-pentenyl , 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl , 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl , 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1 -Ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl , 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkynyl: straight-chain or branched hydrocarbon groups with 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a triple bond 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-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4- Hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl- 1-pentinyl, 3-methyl-4-pentinyl, 4-methyl-1-pentinyl, 4- Methyl-2-pentinyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3- Dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Cycloalkyl: monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Alkylamino: for an alkyl group bonded via an NH group, in which alkyl represents one of the abovementioned alkyl radicals generally having 1 to 6 and in particular 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino and the same;

Dialkylamino: for a radical of the formula N (alkyl) ₂ , in which alkyl represents one of the abovementioned alkyl radicals generally having 1 to 6 and in particular 1 to 4 carbon atoms, for example dimethylamino, diethylamino, methylethylamino, N-methyl-N -propylamino and the like;

Alkylaminocarbonyl: for an alkyl group bonded via a C (O) NH group, in which alkyl represents one of the abovementioned alkyl radicals which generally have 1 to 6 and in particular 1 to 4 carbon atoms, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl , n-butylaminocarbonyl and the like;

Dialkylaminocarbonyl: for a radical of the formula N (alkyl) ₂ , in which alkyl represents one of the abovementioned alkyl radicals which generally have 1 to 6 and in particular 1 to 4 carbon atoms, for example dimethylaminocarbonyl, diethylaminocarbonyl, methylethylaminocarbonyl, N-methyl -N-propylaminocarbonyl and the like;

dC ₄ alkoxy: for an alkyl group bonded via an oxygen having 1 to 4 carbon atoms, e.g. B. methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;

dC ₆ alkoxy: for CC ₄ alkoxy, as mentioned above, and z. B. 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; dC -haloalkoxy: for a dC ₄ -alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine, for example OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ CI , OCHCI ₂ , OCCI 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 CI) -2-chloroethoxy, 1- (CH ₂ Br) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;

d-Cβ-haloalkoxy: for -CC ₄ -haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorhexoxy, 6-chlorohexoxy, 6- Bromhexoxy, 6-iodohexoxy or dodecafluorohexoxy;

Alkenyloxy: alkenyl as mentioned above, which is bonded via an oxygen atom, for example C ₂ -C ₆ alkenyloxy such as vinyloxy, 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-pent enyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1, 1-dimethyl-2-butenyloxy, 1, 1-dimethyl-3-butenyloxy, 1, 2-dimethyl-1-butenyloxy, 1, 2-dimethyl-2-butenyloxy, 1, 2-dimethyl-3-butenyloxy, 1, 3-dimethyl-1-butenyloxy, 1, 3-dimethyl-2-butenyloxy, 1, 3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2, 3-dimethyl-1-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3-dimethyl-2-buteny! Oxy, 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 example 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;

five- or six-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: for example mono- and bicyclic heterocycles (heterocyclyl) containing, in addition to carbon ring members, one to three nitrogen atoms and / or one Oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-lsoxazolidinyl, 4-lsoxazolidinyl, Isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2,4- Thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolid in-2-yl, 1, 3,4-thiadiazolidin- 2-yl, 1, 3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3- isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-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-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4- Hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazine 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 with 7 ring members, containing, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and hexahydroazepinyl such as 2,3,4,5- Tetrahydro [1 H] azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepin-2 -, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1H] azepin-1-, -2-, -3-, -4 -, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] azepin-1-, -2-, -3-, -4-, -5-, - 6- or -7-yl, hexa- hydroazepin-1-, -2-, -3- or -4-yl, tetra-.and hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2 -, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1H] oxepin-2-, - 3-, -4-, -5 -, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, Hexahydroazepin-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 ylidene radicals;

five- to six-membered heteroaromatic radical: an aromatic heterocycle containing one, two or three heteroatoms from the group consisting of oxygen, nitrogen or sulfur: for example C-bonded 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; and C- or N-linked 5-membered heteroaryl which has a fused-on benzene ring and which can be bonded to the group CR ² R ³ via the heterocycle or the fused benzene ring, such as indolyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl , Benzopyrazolyl, benzoisothiazolyl, benzothiazolyl and the like. With regard to the use as fungicides, preference is given to those compounds of the formula I in which the variables and X, A, Ar, R ¹ , R ² , R ³ , Y, m and L have the following meanings independently of one another and in particular in combination.

X halogen, especially chlorine, or dC ₄ -alkyl, especially methyl, particularly preferably halogen and very particularly preferably chlorine;

A is a chemical bond or CH ₂ , in particular a chemical bond;

Ar phenyl, naphthyl, furyl, isoxazolyl, pyridyl or thienyl, in particular phenyl, 2-furyl, 2-thienyl or isoxazol-5-yl, and especially phenyl, where the abovementioned radicals are unsubstituted or can be substituted in the manner described above and in particular have 0, 1, 2 or 3, in particular 0, 1 or 2 of the abovementioned radicals R ^a . Here, R ^{a has} in particular the meanings given below: R ^a halogen, especially chlorine or fluorine, dC ₄ alkyl, especially methyl, CC ₄ alkoxy, especially methoxy, dC ₄ haloalkyl, especially difluoromethyl or trifluoromethyl, dd-haloalkoxy, especially difluoromethoxy or trifluoromethoxy, or 2 radicals R ^a bonded to adjacent C atoms can also represent a group OCH ₂ O.

In a preferred embodiment, a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , together with the group R ^{1 is} C ₂ -C ₄ alkylene, in particular 1, 2-ethanediyl. In particular, Ar is then derived from phenyl, which may also have 1 or 2 further substituents R ^a ;

R ^{1 is} hydrogen, dC ₄ -alkyl, CC ₄ -alkoxy, formyl or dC ₄ -alkylcarbonyl, in particular hydrogen or -CC ₄ -alkyl and especially H, methyl or ethyl;

R ^{2 is} hydrogen, dC ₄ alkyl, especially methyl or ethyl, or C ₃ -C ₆ cycloalkyl, especially cyclopropyl. Preference is also given to compounds of the formula I in which R ² together with R ^{3 is} C ₂ -C ₄ -alkylene or R ² together with a radical R ^a which is arranged in the ortho position to the group CR ² R ³ for C ₂ -C ₄ alkylene, which can carry 1 or 2 methyl groups, for. B. for ethane-1, 2-diyl, propane-1, 3-diyl and 3-methylbutane-1, 3-diyl,

R ^{3 is} hydrogen or CC alkyl, especially methyl, and particularly preferably hydrogen;

Y halogen, CH ₃ or CF ₃ , especially fluorine or chlorine; m 1, 2, 3 or 4, preferably 1, 2 or 3, in particular 1 or 2;

L halogen, cyano, nitro, C ₁ -C ₆ -alkyl, dC ₆ -haloalkyl, CC ₄ -alkoxy and dC ₄ - alkoxycarbonyl, especially fluorine, chlorine, bromine, cyano, dC ₄ -alkyl, CC ₄ - haloalkyl, CC ₄ -Alkoxy or dC ₄ -alkoxycarbonyl, particularly preferably fluorine, chlorine, CC ₂ -alkyl such as methyl or ethyl, -C-C ₂ -Fluoroalkyl such as trifluoromethyl, CC ₂ -alkoxy such as methoxy or dC ₂ -alkoxycarbonyl such as methoxycarbonyl.

These include, in particular, compounds of the formula I in which the phenyl group substituted by Y and L _m for a group of the formula

where # is the point of attachment to the triazolopyrimidine backbone and

Y is fluorine, chlorine, CH ₃ or CF ₃ ;

L ¹ , L ³ independently of one another are hydrogen or fluorine;

L ^{2 is} hydrogen, fluorine, chlorine, cyano, CH ₃ , OCH ₃ or COOCH ₃ ; and

L ^{4 is} hydrogen, fluorine or CH ₃ , where at least one of the radicals L ¹ to L ⁴ and in particular 1 or 2 of the radicals L ¹ to

L ⁴ are different from hydrogen, preferred.

In the groups OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , C (O) OR ¹⁰ , CONR ¹¹ R ¹² and C (= NR ³ ) NR ¹¹ R ¹² , the variables have in particular the meanings given below:

R ⁶ is in particular H, CC ₄ alkyl, C (O) H or dC ₄ alkylcarbonyl;

R ⁷ is in particular H or CC ₄ alkyl;

R ⁸ and R ⁹ are in particular H, CC-alkyl, formyl, CC ₄ -alkylcarbonyl or

CC ₄ alkyl (thiocarbonyl). In particular, NR ⁸ R ^{9 represents} NH ₂ , NHCH ₃ , NHC ₂ H ₅ ,

N (CH ₃ ) ₂ , N (C ₂ H ₅ ) CH ₃ , NHC (O) CH ₃ or NHC (O) H.

R ¹⁰ is in particular C 1 -C ₄ alkyl.

R ¹¹ stands in particular for H or CC alkyl.

R ¹² stands in particular for H or dC ₄ alkyl.

R ¹³ stands in particular for H or CC ₄ alkyl. Examples of preferred compounds of the formula I according to the invention are the compounds of the formula I '(formula I in which A is a chemical bond) and of the formula I "(formula I in which A is CH ₂ ) given in Tables 1 to 72 below. , wherein the variables R ¹ , R ² , R ³ and Ar each together have the meaning given in one of rows 1 to 554 of Table A:

d ") (I")

Table A:

Table 1 Compounds of the formula I "and I" in which X is chlorine, Y is fluorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for one Connection corresponds in each case to one row of table A.

Table 2 Compounds of the formula I 'and I "in which X is CN, Y is fluorine, I_ \ L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 3 Compounds of Formula I "and I" in which X is methyl, Y is fluorine, L ^1, L ² and L ^3, respectively Hydrogen and L ^{4 are} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 4

Compounds of the formula I 'and I "in which X is chlorine, Y is chlorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 5

Compounds of the formula I 'and I "in which X is CN, Y is chlorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 6

Compounds of the formula I 'and I "in which X is methyl, Y is chlorine, L, L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for each compound is one Row of table A corresponds.

Table 7

Compounds of the formula I 'and I "in which X is chlorine, Y is fluorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 8

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 9

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 10

Compounds of the formula I 'and I "in which X is chlorine, Y, L ² and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 11

Compounds of the formula I 'and I "in which X CN, Y, L ² and L ^{4 are} each fluorine, L ¹ and L ³ each represent hydrogen and L ⁴ methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 12

Compounds of the formula I 'and I "in which X is methyl, Y, L ² and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{4 is} methyl and the combination of Ar, R ¹ , R ² and R ³ corresponds to one row of Table A for a connection.

Table 13

Compounds of the formula I 'and I "in which X is chlorine, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methoxy and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 14

Compounds of the formula I 'and I "in which X is CN, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methoxy and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 15

Compounds of the formula I 'and I "in which X is methyl, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methoxy and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 16

Compounds of the formula I 'and I "in which X is chlorine, Y, L ¹ , L ² , L ³ and L ^{4 are} each fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case one line corresponds to Table A.

Table 17

Compounds of the formula I 'and I "in which X is CN, Y, L \ L ² , L ³ and L ^{4 are} each fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case one line of the Table A corresponds.

Table 18

Compounds of the formula I 'and I "in which X is methyl, Y, L ¹ , L ² , L ³ and L ^{4 are} each fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case one line corresponds to Table A.

Table 19

Compounds of formula I 'and I "in which X is chlorine, Y is fluorine, I \ L ³ and L ^4, respectively Hydrogen and L ^{2 are} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 20

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 21

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 22

Compounds of the formula I 'and I "in which X is chlorine, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 23

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 24

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 25

Compounds of the formula I 'and I "in which X is chlorine, Y is chlorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 26

Compounds of the formula I 'and I "in which X is CN, Y is chlorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 27

Compounds of formula I 'and I "in which X is methyl, Y is chlorine, L ¹ , L ³ and L ^{4 are} each Hydrogen and L ^{2 are} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 28

Compounds of the formula I 'and I "in which X is chlorine, Y is fluorine, L ² , L ³ and L ^{4 are} each hydrogen and L ^{1 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 29

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ² , L ³ and L ^{4 are} each hydrogen and L ^{1 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 30

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ² , L ³ and L ^{4 are} each hydrogen and L ^{1 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 31

Compounds of the formula I 'and I "in which X is chlorine, Y is fluorine, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 32

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} fluorine and the combination of Ar, R ¹ R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 33

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 34

Compounds of the formula I 'and I "in which X is chlorine, Y, L ¹ and L ^{2 are} each fluorine, L ³ and L ^{4 are} each hydrogen and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 35

Compounds of the formula I 'and I "in which X CN, Y, L ¹ and L ^{2 are} each fluorine, L ³ and L ⁴ each represent hydrogen and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of Table A.

Table 36

Compounds of the formula I 'and I "in which X is methyl, Y, L ¹ and L ^{2 are} each fluorine, L ³ and L ^{4 are} each hydrogen and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 37

Compounds of the formula I 'and I "in which X is chlorine, Y and L ^{4 are} each fluorine, L and L ^{3 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 38

Compounds of the formula I 'and I "in which X is CN, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 39

Compounds of the formula I 'and I "in which X is methyl, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 40

Compounds of the formula I 'and I "in which X is chlorine, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 41

Compounds of the formula I 'and I "in which X is CN, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 42

Compounds of the formula I 'and I "in which X is methyl, Y is fluorine, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 43

Compounds of the formula I 'and I "in which X is chlorine, Y and L ^{4 are} each fluorine, L ¹ and L ³ each represent hydrogen and L ² methoxycarbonyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 44

Compounds of the formula I 'and I "in which X is CN, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methoxycarbonyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 45

Compounds of the formula I 'and I "in which X is methyl, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} methoxycarbonyl and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 46

Compounds of the formula I 'and I "in which X is chlorine, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} cyano and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 47

Compounds of the formula I 'and I "in which X is CN, Y and L ^{4 are} each fluorine, L ¹ and L ^{3 are} each hydrogen and L ^{2 is} cyano and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one row of table A.

Table 48

Compounds of the formula I 'and I "in which X is methyl, Y and L ^{4 are} each fluorine, L and L ^{3 are} each hydrogen and L ^{2 is} cyano and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 49

Compounds of the formula I 'and I "in which X is chlorine, Y is methyl, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 50

Compounds of the formula I 'and I "in which X is CN, Y is methyl, L ¹ , L ² and L ^{3 are} each hydrogen and L ^{4 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 51

Compounds of formula I 'and I "in which X is methyl, Y is methyl, L ¹ , L ² and L ^3, respectively Hydrogen and L ^{4 are} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 52

Compounds of the formula I 'and I "in which X is chlorine, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 53

Compounds of the formula I 'and I "in which X is CN, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 54

Compounds of the formula I 'and I "in which X is methyl, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 55

Compounds of the formula I 'and I "in which X is chlorine, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 56

Compounds of the formula I 'and I "in which X is CN, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 57

Compounds of the formula I 'and I "in which X is methyl, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} methyl and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 58

Compounds of the formula I 'and I "in which X is chlorine, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 59

Compounds of the formula I 'and I "in which X CN, Y methyl, L ¹ , L ³ and L ⁴ each have a serstoff and L ^{2 are} chlorine and the combination of Ar, R ¹ , R ² and R ³ for each compound corresponds to one row of Table A.

Table 60

Compounds of the formula I 'and I "in which X is methyl, Y is methyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 61

Compounds of the formula I 'and I "in which X is chlorine, Y trifluoromethyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 62

Compounds of the formula I 'and I "in which X is CN, Y is trifluoromethyl, L ¹ , L ³ and ^ are each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ^{3 is} in each case one compound Row of table A corresponds.

Table 63

Compounds of the formula I 'and I "in which X is methyl, Y is trifluoromethyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 64

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

Table 65

Compounds of the formula I 'and I "in which X is CN, Y is trifluoromethyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 66

Compounds of the formula I 'and I "in which X is methyl, Y is trifluoromethyl, L ¹ , L ³ and L ^{4 are} each hydrogen and L ^{2 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 67

Compounds of the formula I ^* and I "in which X is chlorine, Y is trifluoromethyl, L ¹ , L ² and L ⁴ each represent hydrogen and L ³ fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound corresponds in each case to one line of Table A.

Table 68

Compounds of the formula I 'and I "in which X is CN, Y is trifluoromethyl, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 69

Compounds of the formula I 'and I "in which X is methyl, Y is trifluoromethyl, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} fluorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

Table 70

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

Table 71

Compounds of the formula I 'and I "in which X is CN, Y is trifluoromethyl, L ¹ , L ² and ^ are each hydrogen and L ^{3 is} chlorine and the combination of Ar, R, R ² and R ³ for a compound in each case one line corresponds to Table A.

Table 72

Compounds of the formula I 'and I "in which X is methyl, Y is trifluoromethyl, L ¹ , L ² and L ^{4 are} each hydrogen and L ^{3 is} chlorine and the combination of Ar, R ¹ , R ² and R ³ for a compound in each case corresponds to one row of table A.

The compounds according to the invention can be obtained in various ways. Compounds I, in which X is halogen (compounds LA), are generally prepared by reacting 5,7-dihalotriazolopyrimidines of the general formula II with amines of the general formula MI in accordance with the method shown in Scheme 1: Scheme 1:

In Scheme 1, R ¹ - R ³ , Ar, A, L, m and Y have the meanings mentioned above. Shark stands for halogen, especially chlorine. The reaction of II with amines III is advantageously carried out at 0 ° C to 70 ° C, preferably 10 ° C to 35 ° C, preferably in the presence of an inert solvent such as ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cf. WO 98/46608; WO 02/48151].

The use of a base, such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; Excess amine of the formula IM can also serve as the base.

The amines of the formula IM are known and for the most part are commercially available or can be prepared by known methods for the preparation and derivatization of amino acids. 5,7-dihalotriazolopyrimidines of the general formula II are known from the prior art cited at the beginning or can be prepared analogously to the methods described there.

Compounds of the formula I in which X is cyano or dC ₄ -alkoxy (formula IB) can advantageously be prepared from compounds A by the method shown in Scheme 2.

Scheme 2:

In Scheme 2, R ¹ - R ³ , Ar, A, Hai, L, m and Y have the meanings mentioned above. X 'represents cyanide, dC ₄ alkoxy or CC ₄ haloalkoxy. The reaction is advantageously carried out in the presence of an inert solvent. The cation M in formula IV is of little importance; for practical reasons, ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are usually preferred. The reaction temperature is usually from 0 to 120 ° C., preferably from 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)]. Suitable solvents include ethers such as dioxane, diethyl ether and, preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.

Compounds I in which X is dC ₄ alkyl (formula IC, X = X ") can advantageously be prepared starting from starting materials of the formula LA on the routes outlined below.

Compounds of the formula IC in which X "is CC ₄ alkyl can be obtained, for example, by coupling 5-halotriazolopyrimidines of the formula LA with organometallic reagents of the formula V (see scheme 3). In one embodiment of this process, this reaction takes place under Transition metal catalysis, for example in the presence of catalytically effective amounts of Ni or Pd compounds.

Scheme 3:

In the formulas IC and V, X "stands for CC ₄ -alkyl and M for a metal ion of valence Y, such as B, Zn or Sn. This reaction can be carried out, for example, analogously to the following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid. 1, 2345 (1996); WO 99/41255; Aust. J. Chem., Vol. 43, S.733 (1990); J. Org. Chem., Vol. 43, S .358 (1978); J. Chem. Soc. Chem. Commun. S.866 (1979); Tetrahedron Lett., Vol. 34, S.8267 (1993); ibid., Vol. 33, P.413 (1992) ,

Compounds of the formula I in which X is CC ₄ -alkyl or dC -haloalkyl (formula IC, X = X ^* ) can also advantageously be prepared by the following synthetic route, shown in Scheme 4: Scheme 4:

In Scheme 4, R ¹ - R ³ , L, m and Y have the meanings mentioned above. Shark stands in particular for chlorine or bromine, X ^* for dC ₄ alkyl or dC ₄ haloalkyl and R 'stands for C 1 -C ₄ alkyl, in particular for methyl or ethyl.

In a first step, a 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidine VIII is prepared by reaction of 5-aminotriazole VI with ketoester VII by reaction of 5-aminotriazole VI [cf. Chem. Pharm. Bull., 9, 801, (1961)]. The 5-aminotriazole VI used is commercially available. The starting compounds VII are advantageously prepared under the conditions known from EP-A 10 02 788.

The 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines VIII thus obtained are reacted in a second step with halogenating agents [HAL] to give 7-halogenotriazolopyrimidines of the formula IX. Preferred halogenating agents are chlorinating or brominating agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride. The reaction can be carried out in bulk or in the presence of a solvent. Usual reaction temperatures are from 0 to 150 ° C or preferably from 80 to 125 ° C.

The reaction of 7-halogenotriazolopyrimidine IX with the amine of the formula IM is advantageously carried out at 0 ° C. to 70 ° C., in particular 10 ° C. to 35 ° C. The reaction is preferably carried out in the presence of an inert solvent, such as an ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, a halogenated hydrocarbon such as dichloromethane, an aromatic hydrocarbon such as toluene, xylenes, etc. by [cf. WO 98/46608]. The use of a base, such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; Excess amine of the formula IM can also serve as the base.

Compounds of the formula I.C can alternatively also be prepared by reacting compounds LA and dialkyl malonates of the formula XI and subsequent decarboxylation using the method shown in Scheme 5 [cf. US 5,994,360].

Scheme 5:

In Scheme 5, R ¹ - R ³ , Ar, A, L, m and Y have the meanings mentioned above. X '"stands for hydrogen, dC ₃ alkyl or dC ₃ haloalkyl and R" dC ₄ alkyl.

In a first step, the compound LA is reacted with a malonic acid dialkyl ester of the formula X, preferably in the presence of a base, or with the salt of X. The compound XL is obtained in this way. The reaction can be carried out analogously to the process described in US Pat. No. 5,994,360. The malonates XI 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 literature cited.

The subsequent saponification of ester XII takes place under generally customary conditions [cf. US 5,994,360]. Depending on the different structural elements can the alkaline or acidic saponification of the compounds XI may be advantageous. Under the conditions of ester hydrolysis, the decarboxylation to IC can already take place in whole or in part. The decarboxylation is usually carried out at from 20 ° C. to 180 ° C., preferably from 50 ° C. to 120 ° C., in an inert solvent, optionally in the presence of an acid. Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid. Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -Butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol , and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, the reaction is particularly preferably carried out in hydrochloric acid or acetic acid. Mixtures of the solvents mentioned can also be used.

The reaction mixtures obtained by the methods shown in Schemes 1 to 5 are worked up in a conventional manner, e.g. by mixing with water, separation of the phases and, if necessary, chromatographic purification of the crude products. The intermediate and end products fall in part. in the form of colorless or slightly brownish, viscous oils, which are freed from volatile components or purified under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting.

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

If isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). 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 characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Ba- sidiomyceten. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.

They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, Beans, tomatoes, potatoes and squash, as well as on the seeds of these plants.

They are particularly suitable for combating the following plant diseases: Alternaria species on vegetables and fruits, Bipolaris and Drechslera plants on cereals, rice and turf, Blumena 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 arias on various plants, Mycosphaerella arenas on cereals, bananas and peanuts, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Podosphaica on pods, Podospha Pseudocercosporella herpotrichoides on wheat and barley, Pseυdoperonospora-A e on hops and cucumbers, Puccinia arias on cereals, Pyricularia oryzae on rice, Rhizoctonia-A en on cotton, rice and turf, Septoria tritici and Stagonospora nodorum on wheat, Uncinula necatoran Ustilago species on cereals and sugar cane, and Venturia arias (scab) on apples and pears.

The compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, 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 active amount of the active compounds. The application can take place 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% by weight of active ingredient.

Depending on the type of effect desired, the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.

In the case of seed treatment, amounts of active ingredient of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.

When used in material or stock protection, the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, 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 usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants. The following are essentially suitable as solvents / auxiliaries: water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma -Butryolactone), 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 natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.

Alkali, alkaline earth, and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers of sulfonate, condensation products are also used as surface-active substances, and also condensation products tem naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tri-butylphenylpolyphenyl alcohol, fatty alcohol, trihydroxyphenylpolyphenyl alcohol, fatty alcohol, tri-phenylpolyphenyl alcohol, fatty alcohol Castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite liquors and methyl cellulose.

For the production of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions from medium to high boiling points, such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.

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

Examples of formulations include products for dilution in water, e.g.

A Water-soluble concentrates (SL): 10 parts by weight of a compound according to the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other aids are added. The active ingredient dissolves when diluted in water; B Dispersible concentrates (TLC): 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersing agent, for example polyvinylpyrrolidone. When diluted in water, a dispersion results;

C Emulsifiable concentrates (EC): 15 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate G ^' (5% in each case). 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 the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each). This mixture is introduced into water using an emulsifying machine (Ultraturax) and brought to a homogeneous emulsion. Dilution in water results in an emulsion,

E suspensions (SC, OD): 20 parts by weight of a compound according to the invention are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. 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 dispersing and wetting agents and are prepared as water-dispersible or water-soluble granules by means of technical equipment (e.g. extrusion, spray tower, fluidized bed). 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-strator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient;

as well as products for direct application, e.g. 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 dusting agent;

I Granules (GR, FG, GG, MG): 0.5 part by weight of a compound according to the invention is finely ground and combined with 95.5% carriers. Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application;

J ULV solutions (UL); 10 parts by weight of a compound according to the invention are dissolved in an organic solvent e.g. Xylene dissolved. This gives you a product for direct application.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, old dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water. For the production of emulsions, pastes or old dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. 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 process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives. Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.

In the use form as fungicides, the compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to 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, fluquinconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, triadolazolone, triazolonolol, prochlorazolone, tolonazolone, triazolone diolone, triazolone diolazole, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone, triazolone diolone , Triticonazole,

Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,

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

Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronazidolomolol, probolil, probolil, nuarol, probolil, probolil Quinoxyfen, silthiofam, thiabenzazole, thifluzamide, thiophanate methyl, tiadinil, tricyclazole, triforins,

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

• Nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton, nitrophthal-isopropyl

Phenylpyrroles such as fenpiclonil or fludioxonil, • sulfur

• Other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, Dazomet, diclomezin, diclocymet, Diethofen-carb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fennosetanyl, ferim Fosetyl aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, 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 the appropriate modification of the starting compounds to obtain further compounds. The compounds thus obtained are listed in the tables below with physical details.

Example 1: (4-chlorobenzyl) - [5-chloro-6- (2,4,6-trifluorophenyl) [1, 2,4-triazolo] [1,5-a] pyrimidin-7-yl] amine

To a mixture of 75 mg (0.235 mmol) 5,7-dichloro-6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine and 33.28 mg ( 0.235 mmol) of benzylamine in 2 ml of dichloromethane were added at room temperature to 32.57 μl (0.235 mmol) of triethylamine. The reaction mixture was stirred overnight at room temperature. The mixture was then extracted twice with 5 ml of 5% saline. The organic phase was separated, dried and concentrated under reduced pressure to give 94 mg (94.3% yield) of the title compound.

The compounds of the general formula Ia given in Table B below were prepared in accordance with the procedure given for Example 1 (compounds I in which L _{m are} 2,4,6-trifluoro, X is chlorine and A is a chemical bond).

All products were characterized by combined HPLC / mass spectrometry. An analytical RP-18 column (Chromolith Speed ROD from Merck KGaA, Germany) was used for the HPLC, which was operated at 40 ° C. Acetonitrile with 0.1% by volume of trifluoroacetic acid and 0.1% by volume of trifluoroacetic acid / water mixture served as the eluent (the ratio of trifluoroacetic acid / water was changed from 5:95 to 95: 5 within 5 minutes). Mass spectrometry was carried out using a quadrupole Mass spectrometer with electrospray ionization performed at 80V in positive mode.

Table B:

E.g. R ¹ Ar R ² R ³ * 1) min ²⁾ / m / z ³⁾ 64 (CH ₃ ) ₂ CH-phenyl HH - 388/432 1) configuration at the σ-carbon atom 2) retention time in HPLC analysis in Minutes 3) m / z of the [M + H] ⁺ peak

Example 65: Benzyl- [5-chloro-6- (2-chloro-6-fluorophenyl) [1, 2,4-triazolo] [1, 5-a] pyrimidin-7-yl] amine

According to the procedure given for Example 1, the title compound was prepared starting from 5,7-dichloro-6- (2-chloro-6-fluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine and benzylamine ,

Example 66: Benzyl- [5-chloro-6- (2-chloro-4-methoxyphenyl) [1, 2,4-triazolo] [1, 5-a] pyrimidin-7-yl] amine

The title compound was prepared starting from 5,7-dichloro-6- (2-chloro-4-methoxyphenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine and benzylamine according to the procedure given for example 1 ,

The compounds of the general formula Iaa given in Table C below were also prepared in accordance with the instructions given for Example 1 (compounds I in which L _{m are} 2,4,6-trifluoro, X is chlorine and A is methylene).

Table C:

1) Configuration at the ß carbon atom 2) Retention time in HPLC analysis in minutes 3) m / z of the [M + H] ⁺ peak

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

The active ingredients were prepared separately as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.

Example of use 1 - Efficacy against the drought stain caused by Alternaria solani

Leaves of tomato plants of the "Golden Princess" variety were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The next day the leaves were infected with a spore suspension of Alternaria solani, in a 2% aqueous biomalt solution with a density of 0.17 x 10 ⁶ spores / ml. The test plants were then placed in a chamber saturated with water vapor at temperatures of 20 to 22 ° C. After 5 days the disease had developed so strongly on the untreated but infected plants that the infestation could be determined visually. The results are summarized in Table 1. Table 1 :

Example of use 2 - Efficacy against vine peronospora caused by Plasmopara viticola

Leaves of potted vines of the "Riesling" variety were sprayed to runoff point with an aqueous suspension in the active ingredient concentration given below. The following day, the undersides of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola. After that, the vines were first used for Set up for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually. The results are summarized in Table 2.

Table 2:

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

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

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

Table 3:

Claims

claims

1. Substituted triazolopyrimidines of the formula I.

wherein:

X represents halogen, cyano, dC ₄ -alkyl, dC -haloalkyl, dC ₄ -alkoxy or d- C -haloalkoxy;

Y represents halogen, CC ₄ alkyl or dC ₄ haloalkyl;

L independently of one another halogen, CC ₆ -alkyl, C ₂ -C ₆ -alkenyl, CC ₆ - haloalkyl, -C-C ₆ -alkoxy, dC ₆ -haloalkoxy, nitro, amino, NHR, NR ₂ , cyano, S (= O ) _n mean A ¹ or C (= O) A ² , wherein

R independently of one another for dC ₈ alkyl or dC ₈ alkyl carbonyl;

A ¹ for hydrogen, hydroxy, dC ₈ alkyl, CC ₈ alkylamino or di (C ₁ -C ₈ alkyl) amino; n for 0, 1 or 2;

A ^{2 represents} C ₂ -C ₈ alkenyl, CC ₈ alkoxy, dC ₆ haloalkoxy or one of the groups mentioned in A ¹ ; m represents 0, 1, 2, 3 or 4;

A represents a chemical bond or a group CR ⁴ R ⁵ ;

Ar represents phenyl or a 5- or 6-membered heteroaromatic radical which has 1, 2 or 3 heteroatoms selected from O, S and N as ring members, in which phenyl and the heteroaromatic radical can have a fused-on benzene ring and 1, 2, 3 , May have 4 or 5 substituents R ^a , which are halogen, cyano, nitro, hydroxy, mercapto, Amino, carboxyl, aminocarbonyl, aminothiocarbonyl, dC ₄ -alkyl, CC ₄ - haloalkyl, dd-alkoxy, dC ₄ -haloalkoxy, dC ₄ -alkylthio, dC ₄ -alkyl-amino, dC ₄ -dialkylamino, dd-alkylcarbonyl, Cι- C ₄ -Alkylsulfonyl, -C-C ₄ -alkylsulfinyl, -C-C ₄ -alkoxycarbonyl, Cι-C ₄ -alkylcarbonyloxy, CC ₄ - alkylaminocarbonyl and dC ₄ -dialkylaminocarbonyl are selected, with two groups R ^a also bonded to adjacent C atoms can be C ₃ -C ₅ alkylene, in which one or 2 non-adjacent C atoms can be replaced by oxygen or sulfur;

R ^{1 is} hydrogen, dC ₈ -alkyl, which may have a radical R ^b , CC ₈ -haloalkyl, or C ₃ -C ₆ -cycloalkyl, which may be partially or completely halogenated and, if appropriate, 1, 2, 3 or 4 C 1 -C ₄ alkyl groups may have formyl, CC ₈ alkylcarbonyl or CC ₈ alkoxycarbonyl, where R ^{b is} OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , COOR ¹⁰ , CONR ¹¹ R ¹² , CN, NHC (= NR ¹³ ) NR ¹¹ R ¹² , C ₃ -C ₆ cycloalkyl or phenyl, which optionally carries 1, 2, 3, 4 or 5 substituents R ^a ; or with R ² or with a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , stands for C ₂ -C ₄ alkylene, which may contain 1, 2, 3 or 4 CC ₄ alkyl groups and / or can carry 1 or 2 radicals R ^c , where R ^{c is} halogen, OH, dC ₄ -alkoxy or dC -alkoxycarbonyl;

R ² is hydrogen, dC ₄ -alkyl which may have a group R ^d, dC ₄ - haloalkyl, or C ₃ -C ₆ cycloalkyl which may be partially or fully halogenated defined and optionally 1, 2, 3, or 4 CC ₄ can carry alkyl groups means; where R ^{d is} OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , NHC (= NR ¹³ ) NR ¹¹ R ¹² , C ₃ -C ₆ cycloalkyl or phenyl, which may have 1, 2, 3, 4 or 5 substituents R ^a carries, stands; or with a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , stands for C ₂ -C ₄ alkylene, which may be 1, 2, 3 or 4 dC ₄ alkyl groups and / or 1 or 2 residues R ^c can carry;

R ^{3 is} hydrogen or dC ₄ -alkyl or together with R ^{2 is} C ₂ -C ₆ -alkylene, in which 1 C atom can be replaced by an oxygen atom or a sulfur atom and, if appropriate, 1, 2, 3 or 4 dC ₄ - can carry alkyl groups and / or 1 or 2 radicals R ^c ;

R ⁴ , R ⁵ independently of one another represent hydrogen or dC ₈ -alkyl; R ^{6 represents} hydrogen, CC ₈ alkyl, formyl or dC ₈ alkylcarbonyl;

R ^{7 represents} hydrogen or CC ₈ alkyl;

R ⁸ , R ⁹ independently of one another are hydrogen, CC ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-CrC ₄ -alkyl or together with the nitrogen atom to which they are attached, a saturated one 5-, 6- or 7-membered nitrogen heterocycle, which optionally has a further heteroatom selected from O, S and N as a ring member and which carries 1, 2, 3 or 4 CC ₄ alkyl groups, one of the radicals R ⁸ or R ^{9 can} also represent formyl, dC ₈ -alkylcarbonyl or dC ₈ -alkylthiocarbonyl;

R ^{10 represents} H, dC ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₆ cycloalkyl, phenyl or phenyl-d-C ₄ alkyl;

R ¹¹ , R ¹² independently of one another represent hydrogen, -CC ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-dC ₄ -alkyl or together with the nitrogen atom to which they are attached, form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from O, S and N as the ring member and which bears 1, 2, 3 or 4 dC ₄ alkyl groups; and

R ^{13 represents} hydrogen, dC ₈ alkyl or CC ₈ alkoxy; and the agriculturally acceptable salts of the compounds I.

2. Compounds of formula I according to claim 1, in which X is halogen.

3. Compounds of formula I according to claim 1 or 2, wherein A represents a chemical bond.

4. Compounds of formula I according to any one of the preceding claims, wherein Ar is phenyl, naphthyl, furyl, isoxazolyl, pyridyl or thienyl which has 0, 1, 2 or 3 of the aforementioned radicals R ^a .

5. Compounds of formula I according to claim 4, wherein R ^{a is} selected from halogen, dC ₄ alkyl, CC alkoxy, CC ₄ haloalkyl, dC ₄ haloalkoxy, where 2 radicals R ^a bound to adjacent C atoms also for a group OCH ₂ O can stand.

6. Compounds of formula I according to any one of the preceding claims, wherein R ^{1 is} hydrogen, methyl or ethyl or with a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , for C ₂ -C ₄ - Alkylene stands.

7. Compounds of formula I according to any one of the preceding claims, wherein R ^{2 is} hydrogen, CC ₄ alkyl or C ₃ -C ₆ cycloalkyl.

8. Compounds of formula I according to any one of the preceding claims, wherein R ^{3 is} hydrogen.

9. Compounds of formula I according to any one of claims 1 to 5, wherein R ² together with R ^{3 is} C ₂ -C ₄ alkylene.

10. Compounds of formula I according to any one of claims 1 to 5, wherein R ² together with a radical R ^a , which is arranged in the ortho position to the group CR ² R ³ , is C ₂ -C alkylene.

11. Compounds of formula I according to any one of the preceding claims, wherein Y is fluorine or chlorine.

12. Compounds of formula I according to any one of the preceding claims, wherein m is 1 or 2 and L is selected from halogen, cyano, nitro, CC ₆ - alkyl, d-Ce-haloalkyl, -C-C ₆ alkoxy and CC ₆ alkoxycarbonyl.

13. Compounds of formula I according to claim 12, in which the phenyl group substituted by Y and L _m for a group of the formula

where # is the point of attachment to the triazolopyrimidine backbone and Y is fluorine, chlorine, CH ₃ or CF ₃ ; L ¹ , L ³ independently of one another are hydrogen or fluorine; L ^{2 is} hydrogen, fluorine, chlorine, cyano, CH ₃ , OCH ₃ or COOCH ₃ ; and L ^{4 is} hydrogen, fluorine or CH ₃ .

14. Use of a compound of general formula I according to one of the preceding claims for controlling phytopathogenic fungi.

15. An agent suitable for combating harmful fungi, comprising a solid or liquid carrier and a compound of the formula I according to one of claims 1 to 13.

16. A method for combating phytopathogenic fungi, characterized in that the fungi or the materials, plants, soil or seeds to be protected against fungal attack are treated with an effective amount of a compound of the formula I according to one of Claims 1 to 13.