JP2007538028A - Triazolopyrimidine compounds and their use to control pathogens - Google Patents

Abstract

The present invention relates to novel triazolopyrimidine compounds of the general formula (I), their use to control pathogens and pesticides comprising this type of compound as an active ingredient. In formula (I), X, Y, L, m, Ar and A are defined as follows: X is halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy; Y represents halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl; L, independently of one another, halogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, nitro, amino, NHR, NR ₂ , Cy represents S (═O) _n A ¹ or C (═O) A ² ; m represents 0, 1, 2, 3 or 4; A represents a chemical bond or a CR ⁴ R ⁵ group; Ar Represents phenyl or a 5- or 6-membered heteroaromatic group containing 1, 2 or 3 heteroatoms selected from O, S and N as ring members, whereby phenyl and Heteroaromatic groups are fused benzo And may have 1, 2, 3, 4 or 5 R ^a substituents. R ^{1 to} R ³ have the same meaning as cited in claim 1.

Description

  The present invention relates to novel triazolopyrimidine compounds, their use for controlling harmful fungi and crop protection compositions comprising such compounds as active ingredients.

EP-A 71792, US 5,994,360, WO-A 94/20501, EP-A 834 513, WO-A 98/46608 and WO 03/080615 are phenyl groups optionally substituted at the 6-position of the azolopyrimidine ring. And bactericidal triazolo [1,5a] pyrimidines having NH ₂ or primary or secondary amino groups in the 7-position are described.

  GB 2355261 discloses a triazolo [1,5a] pyrimidine that has an arylamino group at the 7-position and is effective for sterilization of the type described above.

  EP-A 550 113 describes a triazolo [1,5a] pyrimidine effective for sterilization, which may have an alkylamino group in the 7-position, the alkyl group in particular may have a phenyl ring. .

  Some of the triazolopyrimidines which have an amino group in the 7-position and are known from the prior art are either unsatisfactory with respect to fungicidal action or have undesirable properties, for example low crop plant compatibility.

  The object of the present invention is therefore to provide novel compounds with improved fungicidal activity and / or better crop plant compatibility.

Surprisingly, this purpose is expressed by the formula I

(Where
X is halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy;
Y is halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl;
L is independently of each other halogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy , Nitro, amino, NHR, NR ₂ , cyano, S (═O) _n A ¹ or C (═O) A ² ;
R, independently of one another, is C ₁ -C ₈ -alkyl or C ₁ -C ₈ -alkylcarbonyl;
A ¹ is hydrogen, hydroxyl, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -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 or ^one of the groups described under A ¹ ;
m is 0, 1, 2, 3 or 4;
A is a chemical bond or group CR ⁴ R ⁵ ;
Ar is phenyl or a 5- or 6-membered heteroaromatic group having 1, 2 or 3 heteroatoms selected from the group consisting of O, S and N as ring members, and heteroaromatic groups may have a fused benzene ring and 1, 2, 3, 4 or 5 substituents R ^a, the substituents R ^a is halogen, cyano, nitro, hydroxyl, mercapto , Amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - alkylamino, C ₁ -C ₄ - dialkylamino, C ₁ -C ₄ - alkylcarbonyl, C ₁ -C ₄ - alkylsulfonyl, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkylcarbonyloxy, C Two groups R ^a selected from the group consisting of ₁ -C ₄ -alkylaminocarbonyl, and C ₁ -C ₄ -dialkylaminocarbonyl, bonded to two adjacent carbon atoms are also 1 or 2 _May be C ₃ -C ₅ -alkylene in which non-adjacent carbon atoms may be substituted with oxygen or sulfur;
R ¹ is hydrogen, C ₁ -C ₈ -alkyl optionally having the group R ^b , may be partially or fully halogenated, and optionally 1, 2, 3 or 4 C C ₁ -C ₈ -haloalkyl or C ₃ -C ₆ -cycloalkyl, formyl, C ₁ -C ₈ -alkylcarbonyl or C ₁ -C ₈ -alkoxycarbonyl optionally having ₁ -C ₄ -alkyl group 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 ( Optionally having 1, 2, 3, 4 or 5 substituents R ^a ; or
Optionally 1, 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or 1 or 2 together with a group R ^a located ortho to R ² or the group CR ² R ³ C ₂ -C ₄ -alkylene which may have two groups R ^c , where R ^c is halogen, OH, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl;
R ² is hydrogen, C ₁ -C ₄ -alkyl optionally bearing the group R ^d , may be partially or fully halogenated, and optionally 1, 2, 3 or 4 C C ₁ -C ₄ -haloalkyl or C ₃ -C ₆ -cycloalkyl optionally having ₁ -C ₄ -alkyl group, 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 (optionally with 1, 2, 3, 4 or 5 substituents R ^a ); or the group CR ² R Optionally together with a group R ^a located in the ortho position to ³ , 1, 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or 1 or 2 groups R ^c C ₂ -C ₄ -alkylene which may have;
R ³ is hydrogen or C ₁ -C ₄ -alkyl, or together with R ² , one carbon atom may be replaced by an oxygen atom or a sulfur atom, and optionally 1 , 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or C ₂ -C ₆ -alkylene optionally having 1 or 2 groups R ^c ;
R ⁴ and R ⁵ , independently of one another, are hydrogen or C ₁ -C ₈ -alkyl;
R ⁶ is hydrogen, C ₁ -C ₈ -alkyl, formyl or C ₁ -C ₈ -alkylcarbonyl;
R ⁷ is hydrogen or C ₁ -C ₈ -alkyl;
Are R ⁸ , R ⁹ independently of one another, hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl? Or, optionally together with the nitrogen atom to which they are attached, further heteroatoms selected from the group consisting of O, S and N as ring members, and 1, 2, 3 or 4 C Forming a saturated 5-, 6- or 7-membered nitrogen heterocycle having a ₁ -C ₄ -alkyl group, one of the groups R ⁸ or R ⁹ is also formyl, C ₁ -C ₈ May be -alkylcarbonyl or C ₁ -C ₈ -alkylthiocarbonyl;
R ¹⁰ is H, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₆ -cycloalkyl, phenyl or phenyl-C ₁ -C ₄ -alkyl;
Is R ¹¹ , R ¹² independently of one another hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl? Or, optionally together with the nitrogen atom to which they are attached, further heteroatoms selected from the group consisting of O, S and N as ring members, and 1, 2, 3 or 4 C ₁ -C ₄ - saturated with alkyl groups 5, to form a nitrogen heterocycle of 6 or 7-membered ring; and
R ¹³ is hydrogen, C ₁ -C ₈ -alkyl or C ₁ -C ₈ -alkoxy)
Of the triazolopyrimidine compound and the agriculturally acceptable salt of Compound I.

  Accordingly, the present invention provides triazolopyrimidine compounds of formula I and their agriculturally acceptable salts.

  The present invention further uses the triazolopyrimidine compounds of formula I, their tautomers and their agriculturally acceptable salts for controlling phytopathogenic fungi (= harmful fungi) and phytopathogenic fungi An effective amount of a compound of formula I, a tautomer of I and / or I or its A method comprising treating with an agriculturally acceptable salt of a tautomer is provided.

  The present invention further provides a composition for controlling harmful fungi, comprising at least one compound of formula I, a tautomer of I and / or an agriculturally acceptable salt thereof. And a composition comprising at least one liquid or solid carrier.

  Depending on the mode of substitution, the compounds of formula I and their tautomers have one or more chiral centers, in which case they exist as a mixture of enantiomers or diastereomers. The present invention provides both pure enantiomers or diastereomers and mixtures thereof.

Suitable agriculturally useful salts are in particular cation salts or acid acid addition salts in which the cation and the anion respectively do not adversely affect the bactericidal action of compound I. Thus, suitable cations are in particular alkali metal ions, preferably sodium and potassium, alkaline earth metal ions, preferably calcium, magnesium and barium, transition metal ions, preferably manganese, copper, zinc and iron, and Ammonium ions optionally having 1 to 4 C ₁ -C ₄ -alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, if desired Trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C ₁ -C ₄ -alkyl) sulfonium, and sulfoxonium ions, preferably tri (C ₁ -C ₄ -alkyl) sulfoxonium.

Useful acid addition salt anions are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfuric acid, dihydrogen phosphate, hydrogen phosphate, phosphoric acid, nitric acid, bicarbonate, carbonic acid, hexafluorosilicic acid, hexafluorophosphorus. Anions of acids, benzoic acids, and C ₁ -C ₄ -alkanoic acids, preferably formic acid, acetic acid, propionic acid and butyric acid. They can be formed by reacting I with the corresponding anionic acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

In the definition of substituents given in the above formula, collective terms generally representative for the substituents are used. The term C _n -C _m indicates the number of possible carbon atoms in each case in the substituent or moiety.

Halogen: fluorine, chlorine, bromine and iodine;
Alkyl and alkyl moieties in alkoxy, alkylcarbonyl, alkylcarbonyloxy, alkylthio, alkylsulfonyl, alkylsulfinyl, alkoxyalkyl, alkoxyalkoxy, alkoxycarbonyl, alkylamino and dialkylamino, alkylaminocarbonyl and dialkylaminocarbonyl: 1-4 Saturated, straight or branched hydrocarbon groups having up to 6, up to 8, up to 10 or up to 10 carbon atoms, for example C ₁ -C ₆ -alkyl, for example 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 Propyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1 -Ethyl-2-methylpropyl;
Alkylene: having 1, 2, 3 or 4 CH ₂ groups, wherein 1, 2, 3 or 4 hydrogen atoms may be substituted with alkyl and / or 1 or 2 hydrogen atoms A straight-chain divalent hydrocarbon group, optionally substituted with a group R ^{c as} defined above;
Haloalkyl: a linear or branched alkyl group having 1 to 4 or up to 6 carbon atoms (as described above), wherein some or all of the hydrogen atoms in these groups are halogen atoms as defined above Optionally substituted with, for example, C ₁ -C ₂ -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoro Methyl, 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-tri Ruoropuropu 2-yl;
Alkenyl: one unsaturated linear or branched hydrocarbon group having 2 to 4, up to 6, up to 8, or up to 10 carbon atoms and one 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 Ru-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: linear or branched hydrocarbon group having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one triple bond at 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-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl Ru-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3- Dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Cycloalkyl: monocyclic saturated hydrocarbon groups having from 3 to 6 carbocyclic member atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Alkylamino: an alkyl group linked by an NH group, wherein alkyl is one of the above mentioned alkyl groups generally having 1 to 6, in particular 1 to 4 carbon atoms, for example methylamino, Ethylamino, n-propylamino, isopropylamino, n-butylamino, etc .;
Dialkylamino: a group of the formula N (alkyl) ₂ , where alkyl is one of the above mentioned alkyl groups generally having 1 to 6, in particular 1 to 4 carbon atoms, for example dimethylamino, Diethylamino, methylethylamino, N-methyl-N-propylamino, etc .;
Alkylaminocarbonyl: an alkyl group linked by a C (O) NH group, wherein the alkyl is one of the above-mentioned alkyl groups generally having 1 to 6, especially 1 to 4 carbon atoms For example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl and the like;
Dialkylaminocarbonyl: a group of the formula C (O) N (alkyl) ₂ , wherein alkyl is one of the abovementioned alkyl groups generally having 1 to 6, in particular 1 to 4 carbon atoms For example, dimethylaminocarbonyl, diethylaminocarbonyl, methylethylaminocarbonyl, N-methyl-N-propylaminocarbonyl and the like;
C ₁ -C ₄ -alkoxy: an alkyl group having 1 to 4 carbon atoms bonded by oxygen, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methyl Propoxy or 1,1-dimethylethoxy;
C ₁ -C ₆ -alkoxy: C ₁ -C ₄ -alkoxy as described above and also eg pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethyl Propoxy, 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 ₁ -C ₄ -haloalkoxy: C ₁ -C ₄ -alkoxy groups as described above, which are partly or wholly substituted by fluorine, chlorine, bromine and / or iodine, preferably fluorine, ie for example 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 -Bro Propoxy, 3-bromopropoxy, 3,3,3-fluoropropoxy, _{3,3,3-trichloro-propoxy, OCH 2 -C 2 F 5,} OCF 2 -C 2 F 5, 1- (CH 2 F) - 2-fluoroethoxy, 1- (CH ₂ Cl) -2-chloroethoxy, 1- (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
C ₁ -C ₆ -haloalkoxy: C ₁ -C ₄ -haloalkoxy as described above and also for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoro Pentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
Alkenyloxy: an alkenyl as described above linked by an oxygen atom, for example C ₂ -C ₆ -alkenyl, 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-butenyloxy, 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-but Nyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-1-butenyloxy, 1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-1- Butenyloxy, 1,3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-1-butenyloxy, 2,3-dimethyl-2- Butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3-dimethyl-2-butenyloxy, 1-ethyl-1-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-propyl Peniruokishi;
Alkynyloxy: alkynyl as described above linked by an oxygen atom, eg C ₃ -C ₆ -alkynyloxy, eg 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyl Oxy, 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-membered or 6-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur as ring members: Monocyclic and bicyclic heterocycles containing 1 to 3 nitrogen atoms and / or 1 oxygen or sulfur atom or 1 or 2 oxygen and / or sulfur atoms in addition to the carbocyclic constituent atoms (heterocyclyl) ), For example, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-iso Xazolidinyl, 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-oxadiazolidine-3-yl, 1,2,4-oxadiazolidine- 5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4- Oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydro Flu-3-yl, 2,4-dihydroflu-2-yl, 2,4-dihydroflu-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-isoxy Sazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazoline- 5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazoline-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-hydropyrazol-1-yl, 3,4-hydropyrazol-3 -Yl, 3,4-hydropyrazol-4-yl, 3,4-hydropyrazol-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-dihydrooxazole-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-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyrida Dinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl Dinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and the corresponding -ylidene group;
7-membered saturated or partially unsaturated heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur as ring members: for example, carbocycle Monocyclic and bicyclic rings with 7 ring atoms, containing 1 to 3 nitrogen atoms and / or 1 oxygen or sulfur atom or 1 or 2 oxygen and / or sulfur atoms in addition to the constituent atoms Heterocycles such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro [1H] azepine-1-,-2-,-3-,-4-,-5-,-6 -Or-7-yl, 3,4,5,6-tetrahydro [2H] azepine-2-,-3-,-4-,-5-,-6- or -7-yl, 2,3,4 , 7-Tetrahydro [1H] azepine-1-,-2-,-3-,-4-,-5-,-6- or -7-yl, 2,3,6,7-tetrahydro [1H] azepine -1-,-2-,-3-,-4-,-5-,-6- or -7-yl, hexahydroazepine-1-,-2-,-3- or -4-yl, tetra And hexa Drooxepinyl, for example 2,3,4,5-tetrahydro [1H] 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 [1H] oxepin-2-,-3-, -4-,-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 corresponding- An iridene group;
5-membered or 6-membered heteroaromatic groups: aromatic heterocycles containing 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur: for example bonded by carbon, 1 to 5-membered heteroaryl containing 3 nitrogen atoms or 1 or 2 nitrogen atoms and 1 sulfur or oxygen atom as ring members, for example 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-oxa Diazol-5-yl, 1,2,4-thi Diazol-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 heteroaryls linked by nitrogen and containing 1 to 3 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 heteroaryls containing 1 to 3 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 also linked by a carbon or nitrogen atom; 5-membered heteroaryl having a fused benzene ring and capable of being bonded to the group CR ² R ³ by a heterocycle or fused benzene ring, such as indolyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl Benzopyrazolyl, benzoisothiazolyl, benzothiazolyl and the like.

For use as fungicides, compounds of the formula I in which the substituents 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: Is preferred.

X is halogen, in particular chlorine, or C ₁ -C ₄ -alkyl, in particular methyl, particularly preferably halogen, very particularly preferably chlorine;
A is a chemical bond or CH ₂ , in particular a chemical bond;
Ar is phenyl, naphthyl, furyl, isoxazolyl, pyridyl or thienyl, in particular phenyl, 2-furyl, 2-thienyl or isoxazol-5-yl, in particular phenyl and the above-mentioned groups are unsubstituted Or may be substituted in the manner described above, and in particular may have 0, 1, 2 or 3, in particular 0, 1 or 2 groups R ^a as described above. Here, ^Ra has in particular the meaning given below:
R ^a is halogen, especially chlorine or fluorine, C ₁ -C ₄ -alkyl, especially methyl, C ₁ -C ₄ -alkoxy, especially methoxy, C ₁ -C ₄ -haloalkyl, especially difluoromethyl or trifluoromethyl, C _The two groups R ^{a which} are ₁ -C ₄ -haloalkoxy, in particular difluoromethoxy or trifluoromethoxy, or bonded to adjacent carbon atoms may also be the group OCH ₂ O.

In a preferred embodiment, the group R ^a located ortho 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 this case, Ar is in particular derived from phenyl optionally having one or two further substituents R ^a .

R ¹ is hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, formyl or C ₁ -C ₄ -alkylcarbonyl, especially hydrogen or C ₁ -C ₄ -alkyl, especially H Methyl or ethyl;
R ² is hydrogen, C ₁ -C ₄ -alkyl, especially methyl or ethyl, or C ₃ -C ₆ -cycloalkyl, especially cyclopropyl. R ² together with R ³ is C ₂ -C ₄ -alkylene or R ² together with a group R ^a located ortho to the group CR ² R ^{3 is} 1 or 2 C ₂ -C ₄ -alkylene optionally having 1 methyl group, for example ethane-1,2-diyl, propane-1,3-diyl and 3-methylbutane-1,3-diyl Are also preferred;
R ³ is hydrogen or C ₁ -C ₄ -alkyl, in particular methyl, particularly preferably hydrogen;
Y is halogen, CH ₃ or CF ₃ , in particular fluorine or chlorine;
m is 1, 2, 3 or 4, preferably 1, 2 or 3, in particular 1 or 2;
L is halogen, cyano, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxycarbonyl, especially fluorine, chlorine, bromine , Cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl, particularly preferably fluorine, chlorine, C ₁ -C ₂ - alkyl, for example methyl or ethyl, C ₁ -C ₂ - alkoxycarbonyl, such as methoxycarbonyl - fluoroalkyl, for example trifluoromethyl, C ₁ -C ₂ - alkoxy, such as methoxy or C ₁ -C _2.

Among these, phenyl groups substituted with Y and L _m are of formula

Wherein # is the point of attachment to the triazolopyrimidine skeleton, Y is fluorine, chlorine, CH ₃ or CF ₃ ; L ¹ and L ³ are independently of each other 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 and at least one group L ^{1 to} L ⁴ , in particular 1 or 2 Groups L ^{1 to} L ⁴ are different from hydrogen)
Particular preference is given to compounds of the formula I in which

In the groups OR ⁶ , SR ⁷ , NR ⁸ R ⁹ , C (O) OR ¹⁰ , CONR ¹¹ R ¹² and C (= NR ¹³ ) NR ¹¹ R ¹² , the substituents have the meanings indicated in particular below:
R ⁶ is in particular H, C ₁ -C ₄ -alkyl, C (O) H or C ₁ -C ₄ -alkylcarbonyl;
R ⁷ is in particular H or C ₁ -C ₄ -alkyl;
R ⁸ and R ⁹ are in particular H, C ₁ -C ₄ -alkyl, formyl, C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -alkyl (thiocarbonyl), and NR ⁸ R ⁹ is in particular 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 is in particular H or C ₁ -C ₄ -alkyl;
R ¹² is in particular H or C ₁ -C ₄ -alkyl;
R ¹³ is in particular H or C ₁ -C ₄ -alkyl.

Examples of preferred compounds of formula I according to the invention are compounds of formula I ′ (formula I in which A is a chemical bond) and formula I ″ (A is CH ₂ ) given in Tables 1 to 72 below. Compounds of formula I), wherein the substituents R ¹ , R ² , R ³ and Ar together in each case have one of the meanings given in lines 1 to 554 of table A :

X is chlorine, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 2
X is CN, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 3
X is methyl, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 4
X is chlorine, Y is chlorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 5
X is CN, Y is chlorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 6
X is methyl, Y is chlorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 7
X is chlorine, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 8
X is CN, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 9
X is methyl, Y is fluorine, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 10
X is chlorine, Y, L ² and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, and the combinations of Ar, R ¹ , R ² and R ³ for each compound are listed in Table A Compounds of formula I ′ and I ″ corresponding to one line.

Table 11
X is CN, Y, L ² and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ⁴ is methyl, Ar, R ¹ , R ² and R for each compound A compound of formula I ′ and I ″, wherein the combination of ³ corresponds to one row of Table A.

Table 12
X is methyl, Y, L ² and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ⁴ is methyl, and Ar, R ¹ , R ² and R for each compound A compound of formula I ′ and I ″, wherein the combination of ³ corresponds to one row of Table A.

Table 13
X is chlorine, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxy, and a combination of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 14
X is CN, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxy, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 15
X is methyl, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxy, and a combination of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 16
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 each compound corresponds to one row of Table A And compounds of formula I ′ and I ″.

Table 17
X is CN, 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 each compound corresponds to one row of Table A And compounds of formula I ′ and I ″.

Table 18
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 each compound corresponds to one row of Table A And compounds of formula I ′ and I ″.

Table 19
X is chlorine, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 20
X is CN, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 21
X is methyl, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 22
X is chlorine, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 23
X is CN, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 24
X is methyl, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 25
X is chlorine, Y is chlorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 26
X is CN, Y is chlorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 27
X is methyl, Y is chlorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 28
X is chlorine, Y is fluorine, L ² , L ³ and L ⁴ are each hydrogen, L ¹ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 29
X is CN, Y is fluorine, L ² , L ³ and L ⁴ are each hydrogen, L ¹ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 30
X is methyl, Y is fluorine, L ² , L ³ and L ⁴ are each hydrogen, L ¹ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 31
X is chlorine, Y is fluorine, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 32
X is CN, Y is fluorine, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 33
X is methyl, Y is fluorine, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 34
X is chlorine, Y, L ¹ and L ² are each fluorine, L ³ and L ⁴ are each hydrogen, and combinations of Ar, R ¹ , R ² and R ³ for each compound are shown in Table A Compounds of formula I ′ and I ″ corresponding to one line.

Table 35
X is CN, Y, L ¹ and L ² are each fluorine, L ³ and L ⁴ are each hydrogen, and combinations of Ar, R ¹ , R ² and R ³ for each compound are shown in Table A Compounds of formula I ′ and I ″ corresponding to one line.

Table 36
X is methyl, Y, L ¹ and L ² are each fluorine, L ³ and L ⁴ are each hydrogen, and the combinations of Ar, R ¹ , R ² and R ³ for each compound are listed in Table A Compounds of formula I ′ and I ″ corresponding to one line.

Table 37
X is chlorine, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methyl, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 38
X is CN, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methyl, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 39
X is methyl, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methyl, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 40
X is chlorine, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 41
X is CN, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 42
X is methyl, Y is fluorine, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 43
X is chlorine, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxycarbonyl, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 44
X is CN, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxycarbonyl, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 45
X is methyl, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is methoxycarbonyl, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 46
X is chlorine, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is cyano, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 47
X is CN, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is cyano, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 48
X is methyl, Y and L ⁴ are each fluorine, L ¹ and L ³ are each hydrogen, L ² is cyano, and combinations of Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, corresponding to one row of Table A.

Table 49
X is chlorine, Y is methyl, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 50
X is CN, Y is methyl, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 51
X is methyl, Y is methyl, L ¹ , L ² and L ³ are each hydrogen, L ⁴ is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 52
X is chlorine, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 53
X is CN, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 54
X is methyl, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 55
X is chlorine, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 56
X is CN, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 57
X is methyl, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is methyl, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 58
X is chlorine, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 59
X is CN, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 60
X is methyl, Y is methyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and the combination of Ar, R ¹ , R ² and R ³ for each compound is Compounds of formula I ′ and I ″ corresponding to one row of Table A.

Table 61
X is chlorine, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 62
X is CN, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 63
X is methyl, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is fluorine, and Ar, R ¹ , R ² and R ³ for each compound Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 64
X is chlorine, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 65
X is CN, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 66
X is methyl, Y is trifluoromethyl, L ¹ , L ³ and L ⁴ are each hydrogen, L ² is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 67
X is chlorine, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 68
X is CN, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 69
X is methyl, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is fluorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 70
X is chlorine, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 71
X is CN, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

Table 72
X is methyl, Y is trifluoromethyl, L ¹ , L ² and L ⁴ are each hydrogen, L ³ is chlorine, and for each compound, Ar, R ¹ , R ² and R ³ Compounds of formula I ′ and I ″, wherein the combination corresponds to one row of Table A.

The compounds of the invention can be obtained by different routes. Compound I where X is a halogen (formula IA) is generally prepared by reacting a 5,7-dihalotriazolopyrimidine of formula II with an amine of formula III according to the method shown in Scheme 1:
Scheme 1:

In Scheme 1, R ^{1 to} R ³ , Ar, A, L, m, and Y are as defined above. Hal is a halogen, in particular chlorine. The reaction of II with amine III is advantageously between 0 and 70 ° C., preferably between 10 and 35 ° C., preferably with an inert solvent such as ether such as dioxane, diethyl ether, especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane. And in the presence of aromatic hydrocarbons such as toluene [cf. WO 98/46608; WO 02/48151].

  It is preferred to use a base, for example a tertiary amine, for example triethylamine or an inorganic base, for example potassium carbonate, and an excess of an amine of formula III can serve as the base.

  Amines of formula III are known and most are commercially available or can be prepared by known methods for preparing and deriving amino acids. 5,7-Dihalotriazolopyrimidines of the formula II are known from the prior art cited at the outset or can be prepared analogously to the methods described therein.

Compounds of formula I where X is cyano or C ₁ -C ₄ -alkoxy (formula IB) can advantageously be prepared from compound IA by the method shown in Scheme 2:
Scheme 2:

In Scheme 2, R ^{1 to} R ³ , Ar, A, Hal, L, m, and Y are as defined above. X ′ is cyanide, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy. The reaction is advantageously carried out in the presence of an inert solvent. The cation M in formula IV is not critical for practical reasons and is usually preferably an ammonium, tetraalkylammonium or alkali metal or alkaline earth metal salt. The reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. Heterocycl. Chem. 12 (1975), 861-863]. Suitable solvents include ethers such as dioxane, diethyl ether, and preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.

Compound I where X is C ₁ -C ₄ -alkyl (formula IC, X = X ″) can advantageously be prepared from the starting material of formula IA by the route described below.

A compound of formula IC where X ″ is C ₁ -C ₄ -alkyl can be obtained, for example, by conjugating a 5-halotriazolopyrimidine of formula IA with an organometallic reagent of formula V (see Scheme 3). ). In one embodiment of this method, the reaction is performed with a transition metal catalyst, for example in the presence of a catalytically effective amount of a Ni or Pd compound.

Scheme 3:

In the formulas IC and V, X ″ is C ₁ -C ₄ -alkyl and M is a valence Y metal ion such as B, Zn or Sn. This reaction can be performed, for example, in the same manner as the following method: J. Chem. Soc. Perkin Trans. 1 (1994), 1187, ibid (1996), 2345; WO 99/41255; Aust. J. Chem 43 (1990), 733; J. Org. Chem. 43 (1978), 358; J. Chem. Soc. Chem. Commun. (1979), 866; Tetrahedron Lett. 34 (1993), 8267; ibid 33 ( 1992), 413.

Compounds of formula I wherein X is C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl (formula IC, X = X *) are also preferably prepared by the following synthetic route shown in Scheme 4 can do:
Scheme 4:

In Scheme 4, R ^{1 to} R ³ , L, m, and Y are as defined above. Hal is in particular chlorine or bromine, X * is C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl and R ′ is C ₁ -C ₄ -alkyl, in particular methyl or ethyl.

In the first stage, 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidine VIII is prepared by a method known per se by reacting 5-aminotriazole VI with ketoester VII [cf. Chem. Pharm. Bull. 9 (1961), 801]. The 5-aminotriazole VI used is commercially available. The starting material VII is preferably prepared from EP-A 10 02 788 under known conditions.

  The resulting 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidine VIII is converted in step 2 to the 7-halotriazolopyrimidine of formula IX using the halogenating agent [HAL]. 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 by itself or in the presence of a solvent. Conventional reaction temperatures are 0-150 ° C or preferably 80-125 ° C.

  The reaction of 7-halotriazolopyrimidine IX with the amine of formula III is advantageously carried out at 0 to 70 ° C., in particular 10 to 35 ° C. The reaction is preferably carried out in the presence of an inert solvent such as an ether such as dioxane, diethyl ether, or especially tetrahydrofuran, a halogenated hydrocarbon such as dichloromethane, an aromatic hydrocarbon such as toluene, xylene, etc. [cf. WO 98/46608].

  The use of a base such as a tertiary amine such as triethylamine or an inorganic base such as potassium carbonate is preferred; an excess of an amine of formula III can also act as a base.

  Alternatively, compounds of formula IC can also be prepared by reacting compound IA and dialkyl malonate of formula XI followed by decarboxylation according to the method shown in Scheme 5 [cf. US 5 994 360 ].

Scheme 5:

In Scheme 5, R ^{1 to} R ³ , Ar, A, L, m, and Y are as defined above. X ″ ′ is halogen, C ₁ -C ₃ -alkyl or C ₁ -C ₃ -haloalkyl, and R ″ is C ₁ -C ₄ -alkyl.

In the first step, compound IA is reacted with a dialkyl malonate of formula X or with a salt of X, preferably in the presence of a base. This gives compound XI. The reaction can be carried out in the same manner as described in US 5 994 360. Malonate XI is known from the literature [. Am. Chem. Soc. 64 (1942), 2714; J. Org. Chem. 39 (1974), 2172; Helv. Chim. Acta 61 (1978), 1565] Or it can manufacture according to the cited literature.

  Ester XII is then generally hydrolyzed under conventional conditions [cf. US 5 994 360]. Depending on the various structural elements, alkaline or acid hydrolysis of compound XI may be advantageous. Under the conditions of ester hydrolysis, there may already be total or partial decarboxylation to I.C '. Usually, the decarboxylation takes place at a temperature of 20 to 180 ° C., preferably 50 to 120 ° C., in an inert solvent, if appropriate 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 also dimethyl sulfoxide, dimethylformamide and dimethylacetamide The reaction is particularly preferably carried out in hydrochloric acid or acetic acid. It is also possible to use mixtures of the solvents mentioned.

  The reaction mixtures obtained by the methods shown in schemes 1 to 5 are processed in the customary manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography. . Some of the intermediates and final products are obtained in the form of a colorless or somewhat brownish viscous oil which can be purified by heating at a reduced pressure or removing volatile components. Can do. If the intermediate and final product are obtained as solids, purification can also be performed by recrystallization or digestion.

  If individual compounds I cannot be obtained by the routes described above, they can be obtained by induction of other compounds I.

  Separation is generally not necessarily required if the synthesis results in a mixture of isomers. This is because, in some cases, individual isomers can be internally converted (eg, under the action of light, acid or base) during processing for use during application. Such conversion can also take place after use, for example in the case of plant treatment, in the treated plant or in the harmful fungus to be controlled.

  Compound I is suitable as a fungicide. They are distinguished by a significant efficacy against a broad spectrum of phytopathogenic fungi, especially fungi from the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes types. Some are effective throughout and they can be used for plant protection as leaf and soil fungicides.

  They include various cultivated plants such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugarcane, grapes, fruits and ornamental plants and vegetables such as cucumbers, beans, tomatoes, Of particular importance in the control of numerous fungi in potatoes and cucumbers and in the seeds of these plants.

They are particularly suitable for controlling the following plant diseases:
Alternaria species in fruits and vegetables,
Bipolaris and Drechslera species in cereals, rice and turf,
・ Blumeria graminis (powdery mildew) in cereals,
Botrytis cinerea (grey mold disease) in strawberries, vegetables, ornamental plants and vines,
Erysiphe cichoracearum and Sphaerotheca fuliginea in Uri,
Fusarium and Verticillium species in various plants,
Mycosphaerella species in cereals, bananas and peanuts,
Phytophthora infestans in potatoes and tomatoes,
・ Plasmopara viticola in vines,
Podosphaera leucotricha in apples,
Pseudocercosporella herpotrichoides in wheat and barley,
Pseudoperonospora species in hops and cucumbers,
・ Puccinia species in cereals,
・ Pyricularia oryzae in rice,
Rhizoctonia in cotton, rice and turf,
・ Septoria tritici and Stagonospora nodorum in wheat,
・ Uncinula necator in vines,
• Ustilago species in cereals and sugarcane; and • Venturia species (apple scab) in apples and pears.

  Compound I is also suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of substances (eg wood, paper, paint dispersions, fibers or textiles) as well as the protection of stored products.

  Compound I is used by treating fungi or plants, seeds, substances or soil to be protected from fungal attack with an active compound in an amount effective for sterilization. Application can take place both before and after infection by the substance, plant or seed fungus.

  Bactericidal compositions generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

  When used in plant protection, the amount applied is 0.01 to 2.0 kg of active compound per ha, depending on the type of effect desired.

  In the treatment of seeds, an amount of active compound of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed is generally required.

  When used in the protection of substances or stored products, the amount of active compound applied depends on the type of application area and the desired effect. The amounts customarily applied in the protection of the substances are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active compound per cubic meter of processed substance.

  Compound I can be converted into conventional formulations such as solutions, emulsions, suspensions, powders, powders, pastes and granules. The application form depends on the particular purpose, and in each case a fine and homogeneous distribution of the compounds according to the invention must be ensured.

The formulations are prepared in a known manner, for example by diluting the active compound with solvents and / or carriers, if desired using emulsifiers and dispersants. Suitable solvents / adjuncts are essentially the following:
-Water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg mineral oil fraction), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma butyrolactone), pyrrolidones (NMP, NOP) ), Acetate (glycol diacetate), glycol, fatty acid dimethylamide, fatty acid and fatty acid ester. In principle, solvent mixtures can also be used.

  -Supports such as ground natural minerals (eg kaolin, clay, talc, chalk) and ground synthetic minerals (eg highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyls) Sulfonates and aryl sulfonates) and dispersants such as lignosulfite effluent and methylcellulose.

  Suitable surfactants include lignosulfonic acid, naphthalene sulfonic acid, phenol sulfonic acid, dibutyl naphthalene sulfonic acid, alkyl aryl sulfonate, alkyl sulfate, alkyl sulfonate, fatty alcohol sulfate, fatty acid alkali metal, alkaline earth metal and ammonium salts. , And sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol , Nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol Ether, tristearyl phenyl polyglycol ether, alkylaryl polyether alcohol, alcohol and fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, Lignosulfite waste liquor and methylcellulose.

  Suitable for the production of directly sprayable solutions, emulsions, pastes or oil dispersions are medium to high boiling mineral oil fractions such as kerosene or diesel oil, as well as coal tar oil and oils of vegetable or animal origin, Aliphatic, cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalene or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong solvents such as dimethyl sulfoxide N-methylpyrrolidone and water.

  Powders, materials for dispersion and dispersible products can be produced by mixing or pulverizing the active substance with a solid carrier.

  Granules, such as coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compound to a solid carrier. Examples of solid carriers are mineral soils such as silica gel, silicates, talc, kaolin, attaclay, limestone, lime, chalk, balls, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, Fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and plant-derived products such as cereal flour, bark flour, wood flour and nutshell flour, cellulose powder and other solid carriers.

  In general, the formulations comprise between 0.01 and 95% by weight of active compound, preferably between 0.1 and 90%. The active compounds are used in a purity of 90-100%, preferably 95-100% (according to NMR spectrum).

  Examples of formulations include products for dilution with water, such as:

A Water-soluble concentrate (SL)
10 parts by weight of the compound of the invention are dissolved in water or a water-soluble solvent. As an alternative, wetting agents or other adjuvants are added. The active compound dissolves when diluted with water.

B Dispersible concentrate (DC)
20 parts by weight of the compound according to the invention are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.

C Emulsifiable concentrate (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 (5% in each case). Dilution with water gives an emulsion.

D Emulsion (EW, EO)
40 parts by weight of a compound of the invention is dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% in each case). This mixture is introduced into water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.

E Suspension (SC, OD)
In a stirred ball mill, 20 parts by weight of a compound of the invention are milled with the addition of a dispersant, a wetting agent and water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.

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

G Water-dispersible powder and water-soluble powder (WP, SP)
75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of a dispersant, a wetting agent and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.

And, for example, products applied undiluted
H Dispersible powder (DP)
5 parts by weight of the compound of the invention are finely ground and mixed well with 95% finely divided kaolin. This gives a sprayable product.

I Granule (GR, FG, GG, MG)
0.5 parts by weight of the compound of the invention are finely ground and combined with 95.5% of the carrier. Current methods are extrusion, spray drying or fluidized bed. This gives granules to be applied undiluted.

J ULV solution (UL)
10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example xylene. This gives a product to be applied undiluted.

  The active compound can be used as such, in the form of its formulation or in the form of use produced therefrom, for example directly sprayable solutions, powders, suspensions or dispersions by spraying, atomizing, spreading, dispersing or flowing, It can be used in the form of emulsions, oily dispersions, pastes, dispersible products, substances to disperse, or granules. The use form depends solely on the intended purpose, and in each case is intended to ensure the finest possible distribution of the active compounds according to the invention.

  Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. In order to produce emulsions, pastes or oily dispersions, the material as such or dissolved in oil or solvent can be homogenized in water by means of wetting agents, tackifiers, dispersing agents or emulsifiers. Alternatively, it is possible to produce concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, such concentrate for dilution with water. It is suitable for.

  The concentration of the active compound in the ready-to-use preparation can vary within a relatively wide range. Generally, it is 0.0001 to 10%, preferably 0.01 to 1%.

  The active compounds can also be used successfully in the ultra-low volume method (ULV), whereby applying formulations containing more than 95% by weight of active compounds or applying active compounds without additives Even is possible.

  Various types of oils, wetting agents, adjuvants, herbicides, fungicides, other pesticides or fungicides can be added to the active compounds and, if appropriate, not added until just before use (tank mix). These agents can be mixed with the agent of the present invention in a weight ratio of 1:10 to 10: 1.

  The compounds according to the invention can also be present in use form as fungicides together with other active compounds such as herbicides, insecticides, growth regulators, fungicides or fertilizers. Mixing compounds I or compositions containing them in application forms as fungicides with other fungicides often results in an expansion of the resulting active germicidal spectrum.

The following list of fungicides with which the compounds of the invention can be used is intended to illustrate possible combinations and is not limiting:
Acyl alanines, such as benalaxyl, metalaxyl, off-lace or oxadixyl,
Amine derivatives such as aldimorph, dodin, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctazine, spiroxamine or tridemorph,
Anilinopyrimidine, such as pyrimethanil, mepanipyrim or cyprodinil,
Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
Azoles such as vitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, hexaconazole, imazalyl, metconazole, microbutanyl, penconazole, propiconazole, Prochloraz, prothioconazole, tebuconazole, triadimephone, triadimenol, triflumizole or triticonazole,
Dicarboximides such as iprodione, microzoline, procymidone or vinclozolin,
Dithiocarbamates, such as felbam, nabam, maneb, mancozeb, metam, methylam, propineb, polycarbamate, thiram, dilam or dineb,
Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, siazofamide, dazomet, dithianon, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametopyl, isoprothiolane, mepronil, nuarimol, probenazol, proquinodil , Pyrifenox, pyroxylone, quinoxifene, silthiofam, thiabendazole, tifluzamide, thiophanate-methyl, thiazinyl, tricyclazole or trifolin,
Copper disinfectants such as Bordeaux mixture, copper acetate, copper oxychloride or basic copper sulfate,
Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone or nitrophthalisopropyl,
Phenyl pyrrole, such as fenpiclonyl or fludioxonil,
・ Sulfur,
Other fungicides such as acibenzolar-S-methyl, bench avaricarb, carpropamide, chlorothalonil, cyflufenamide, simoxanyl, dazomet, diclomedin, diclocimet, dietofencarb, edifenfos, ethaboxam, fenhexamide, fentinacetate, phenoxanyl, Ferrimzone, fluazinam, focetyl, focetyl-aluminum, iprovalicarb, hexachlorobenzene, metolaphenone, pencyclon, propamocarb, phthalide, torquelophos-methyl, quintozene or zoxamide
Strobilurin, such as azoxystrobin, dimoxystrobin, fluoxastrobin, crezoxime-methyl, metminostrobin, orissastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin,
Sulfenic acid derivatives, such as captaphore, captan, diclofluuride, phorpet or tolylfluanid,
Cinnamide and similar compounds, such as dimethomorph, flumethover or fulmorph.

Synthetic Examples Additional compounds were prepared by appropriate modification of the starting compounds using the procedures described in the following synthetic examples. The compounds thus obtained are listed in the table below together with physical data.

Example 1:
(4-Chlorobenzyl) [5-chloro-6- (2,4,6-trifluorophenyl) [1,2,4-triazolo] [1,5-a] pyrimidin-7-yl] -amine at room temperature 32.57 μl (0.235 mmol) of triethylamine was added to 75 mg (0.235 mmol) of 5,7-dichloro-6- (2,4,6-trifluorophenyl) [1,2,4] triazolo in 2 ml of dichloromethane. To a mixture of [1,5-a] -pyrimidine and 33.28 mg (0.235 mmol) benzylamine. The reaction mixture was stirred at room temperature overnight. The mixture was then extracted twice with in each case 5 ml of 5% strength sodium chloride solution. 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 formula Ia listed in Table B below (Compound I where L _m is 2,4,6-trifluoro, X is chlorine and A is a chemical bond) are given for Example 1. Prepared using the same procedure.

All products were characterized by combined HPLC / mass spectrometry. For HPLC, an analytical RP-18 column (Merck KGaA, Chromolith Speed ROD from Germany) was used and operated at 40 ° C. The mobile phase is acetonitrile with 0.1% by volume trifluoroacetic acid and 0.1% by volume trifluoroacetic acid / water mixture (the ratio of trifluoroacetic acid / water changed from 5:95 to 95: 5 over 5 minutes). there were. Mass spectrum measurements were performed using a quadrupole mass spectrometer with electrospray ionization at 80V in positive mode.

Example 65:
Benzyl- [5-chloro-6- (2-chloro-6-fluorophenyl) [1,2,4-triazolo] [1,5-a] pyrimidin-7-yl] amine
Starting with 5,7-dichloro-6- (2-chloro-6-fluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine and benzylamine is given for Example 1. The title compound was prepared using the same procedure.

Example 66:
Benzyl- [5-chloro-6- (2-chloro-4-methoxyphenyl) [1,2,4-triazolo] [1,5-a] pyrimidin-7-yl] amine
Starting with 5,7-dichloro-6- (2-chloro-4-methoxyphenyl) [1,2,4] triazolo [1,5-a] pyrimidine and benzylamine, given for Example 1 The title compound was prepared using the same procedure.

The compounds of formula Iaa listed in Table C below (Compound I wherein L _m is 2,4,6-trifluoro, X is chlorine and A is methylene) are given for Example 1. The procedure was used to make the same.

The bactericidal action of the compound of formula I was demonstrated by the following experiment:
The active compound was prepared separately as a stock solution with 0.25% by weight of active compound in acetone or DMSO. 1% by weight of the emulsifier Uniperol ™ EL (wetting agent based on ethoxylated alkylphenols with emulsifying and dispersing action) was added to the solution and the mixture was diluted with water to the desired concentration.

Example of Use 1- An aqueous suspension containing the active compound at the following concentrations is sprayed on the run off point of tomato seedlings of the active cultivar "Goldene Prinzessin" against summer plague caused by Alternaria solani. did. The next day, the leaves were infected with a spore suspension of Alternaria solani in a 2% strength aqueous biomalt solution having a density of 0.17 × 10 ⁶ spores / ml. The test plants were then placed in a steam saturated room at a temperature of 20-22 ° C. After 5 days, the disease in untreated but infected control plants was developed to such an extent that infection could be determined visually. The results are summarized in Table 1.

Use Case 2- An aqueous suspension containing the active compound at the following concentration at the pour point of potted vine leaves of active cultivar "Riesling" against vine peronospora caused by Plasmopara viticola Sprayed. The next day, the back of the leaves was inoculated with an aqueous spore sac suspension of Plasmopara viticola. The vines were then first placed in a 24 ° C. steam saturated room for 48 hours and then placed in a greenhouse at a temperature of 20-30 ° C. for 5 days. After this, the plants were placed again in a humid room for 16 hours to promote the development of the spore stalk. Next, the extent of the infection on the back of the leaf was visually determined. The results are summarized in Table 2.

Use Example 3-Tomato leaf blight caused by Phytophthora infestans, active or protective application active compounds separately or together are prepared as stock solutions with 25 mg of active compound, It was made up to 10 ml with a mixture of 99: 1 volume ratio of acetone and / or DMSO and emulsifier Uniperol ™ EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenol). The mixture was then made up to 100 ml with water. This stock solution was diluted to the active compound concentration described below with the solvent / emulsifier / water mixture described.

The leaves of the potted tomato seedlings were sprayed with an aqueous suspension having the active compound concentration described below. The next day, the leaves were infected with an aqueous spore sac suspension of Phytophthora infestans. The plants were then placed in a steam saturated room at a temperature of 18-20 ° C. After 6 days, leaf blight in untreated but infected control plants was developed to such an extent that the infection rate could be determined visually in%.

Claims (16)

Formula I

(Where
X is halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy;
Y is halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl;
L is independently of each other halogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy , Nitro, amino, NHR, NR ₂ , cyano, S (═O) _n A ¹ or C (═O) A ² ;
R, independently of one another, is C ₁ -C ₈ -alkyl or C ₁ -C ₈ -alkylcarbonyl;
A ¹ is hydrogen, hydroxyl, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -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 or ^one of the groups described under A ¹ ;
m is 0, 1, 2, 3 or 4;
A is a chemical bond or group CR ⁴ R ⁵ ;
Ar is phenyl or a 5- or 6-membered heteroaromatic group having 1, 2 or 3 heteroatoms selected from the group consisting of O, S and N as ring members, and heteroaromatic groups may have a fused benzene ring and 1, 2, 3, 4 or 5 substituents R ^a, the substituents R ^a is halogen, cyano, nitro, hydroxyl, mercapto , Amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - alkylamino, C ₁ -C ₄ - dialkylamino, C ₁ -C ₄ - alkylcarbonyl, C ₁ -C ₄ - alkylsulfonyl, C ₁ -C ₄ - alkylsulfinyl, C ₁ -C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkylcarbonyloxy, C Two groups R ^a selected from the group consisting of ₁ -C ₄ -alkylaminocarbonyl, and C ₁ -C ₄ -dialkylaminocarbonyl, bonded to two adjacent carbon atoms are also 1 or 2 _May be C ₃ -C ₅ -alkylene in which non-adjacent carbon atoms may be substituted with oxygen or sulfur;
R ¹ is hydrogen, C ₁ -C ₈ -alkyl optionally having the group R ^b , may be partially or fully halogenated, and optionally 1, 2, 3 or 4 C C ₁ -C ₈ -haloalkyl or C ₃ -C ₆ -cycloalkyl, formyl, C ₁ -C ₈ -alkylcarbonyl or C ₁ -C ₈ -alkoxycarbonyl optionally having ₁ -C ₄ -alkyl group 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 ( Optionally having 1, 2, 3, 4 or 5 substituents R ^a ; or
Optionally 1, 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or 1 or 2 together with a group R ^a located ortho to R ² or the group CR ² R ³ C ₂ -C ₄ -alkylene which may have two groups R ^c , where R ^c is halogen, OH, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl;
R ² is hydrogen, C ₁ -C ₄ -alkyl optionally bearing the group R ^d , may be partially or fully halogenated, and optionally 1, 2, 3 or 4 C C ₁ -C ₄ -haloalkyl or C ₃ -C ₆ -cycloalkyl optionally having ₁ -C ₄ -alkyl group, 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 (optionally with 1, 2, 3, 4 or 5 substituents R ^a ); or the group CR ² R Optionally together with a group R ^a located in the ortho position to ³ , 1, 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or 1 or 2 groups R ^c C ₂ -C ₄ -alkylene which may have;
R ³ is hydrogen or C ₁ -C ₄ -alkyl, or together with R ² , one carbon atom may be replaced by an oxygen atom or a sulfur atom, and optionally 1 , 2, 3 or 4 C ₁ -C ₄ -alkyl groups and / or C ₂ -C ₆ -alkylene optionally having 1 or 2 groups R ^c ;
R ⁴ and R ⁵ , independently of one another, are hydrogen or C ₁ -C ₈ -alkyl;
R ⁶ is hydrogen, C ₁ -C ₈ -alkyl, formyl or C ₁ -C ₈ -alkylcarbonyl;
R ⁷ is hydrogen or C ₁ -C ₈ -alkyl;
Are R ⁸ , R ⁹ independently of one another, hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl? Or, optionally together with the nitrogen atom to which they are attached, further heteroatoms selected from the group consisting of O, S and N as ring members, and 1, 2, 3 or 4 C Forming a saturated 5-, 6- or 7-membered nitrogen heterocycle having a ₁ -C ₄ -alkyl group, one of the groups R ⁸ or R ⁹ is also formyl, C ₁ -C ₈ May be -alkylcarbonyl or C ₁ -C ₈ -alkylthiocarbonyl;
R ¹⁰ is H, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₆ -cycloalkyl, phenyl or phenyl-C ₁ -C ₄ -alkyl;
Is R ¹¹ , R ¹² independently of one another hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl? Or, optionally together with the nitrogen atom to which they are attached, further ring heteroatoms selected from the group consisting of O, S and N, and 1, 2, 3 or 4 C ₁ -C ₄ - saturated with alkyl groups 5, to form a nitrogen heterocycle of 6 or 7-membered ring; and
R ¹³ is hydrogen, C ₁ -C ₈ -alkyl or C ₁ -C ₈ -alkoxy)
Substituted triazolopyrimidines or agriculturally acceptable salts of Compound I. A compound of formula I according to claim 1, wherein X is halogen. A compound of formula I according to claim 1 or 2, wherein A is a chemical bond. 4. A compound of formula I according to any one of claims 1 to 3, wherein Ar is phenyl, naphthyl, furyl, isoxazolyl, pyridyl or thienyl having 0, 1, 2 or 3 groups R ^a as defined above. R ^a is selected from the group consisting of halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, and adjacent carbon atoms The compound of formula I according to claim 4, wherein the two bonded groups R ^a may also be a group OCH ₂ O. R ¹ is hydrogen, methyl or ethyl or C ₂ -C ₄ -alkylene together with a group R ^a located ortho to the group CR ² R ³ A compound of formula I according to any one of the preceding claims. R ² is hydrogen, C ₁ -C ₄ - alkyl or C ₃ -C ₆ - compound of formula I according to any one of claims 1-6 cycloalkyl. Compounds of formula I according to any one of claims 1 to 7 R ³ is hydrogen. R ² together with R ³ C ₂ -C ₄ - Compounds of formula I according to any one of claims 1 to 5 is alkylene. A compound of formula I according to any one of claims 1 to 5, wherein R ² is C ₂ -C ₄ -alkylene together with a group R ^a located ortho to the group CR ² R ³ . . 11. A compound of formula I according to any one of claims 1 to 10, wherein Y is fluorine or chlorine. m is 1 or 2 and L is from halogen, cyano, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy and C ₁ -C ₆ -alkoxycarbonyl 12. A compound of formula I according to any one of claims 1 to 11 selected from the group consisting of: The phenyl group is replaced by Y and L _m is of the formula

(In the formula, # is a point bonded to a triazolopyrimidine skeleton,
Y is fluorine, chlorine, CH ₃ or CF ₃ ;
L ¹ and L ³ are each independently 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 )
13. A compound of formula I according to claim 12, wherein 14. A method of using a compound of formula I according to any one of claims 1 to 13 for controlling plant pathogens. 14. A composition suitable for controlling harmful fungi, comprising a solid or liquid carrier and a compound of formula I according to any one of claims 1-13. 14. A method for controlling phytopathogenic fungi, wherein the fungus or a substance, plant, soil or seed to be protected against fungal attack is an effective amount of the formula of any one of claims 1-13. Treating with a compound of I.