EP1751162A1 - Composes triazolopyrimidine et leur utilisation pour reguler des champignons pathogenes - Google Patents

Composes triazolopyrimidine et leur utilisation pour reguler des champignons pathogenes

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Publication number
EP1751162A1
EP1751162A1 EP05744598A EP05744598A EP1751162A1 EP 1751162 A1 EP1751162 A1 EP 1751162A1 EP 05744598 A EP05744598 A EP 05744598A EP 05744598 A EP05744598 A EP 05744598A EP 1751162 A1 EP1751162 A1 EP 1751162A1
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European Patent Office
Prior art keywords
alkyl
formula
compounds
hydrogen
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP05744598A
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German (de)
English (en)
Inventor
Carsten Blettner
Frank Schieweck
I. Blasco Jordi Tormo
Bernd Müller
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Joachim Rheinheimer
Peter Schäfer
Anja Schwögler
Oliver Wagner
John-Bryan Speakman
Thorsten Jabs
Siegfried Strathmann
Ulrich Schöfl
Maria Scherer
Reinhard Stierl
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BASF SE
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BASF SE
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • Triazolopyrimidine compounds and their use in combating harmful fungi Triazolopyrimidine compounds and their use in combating harmful fungi
  • 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.
  • 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.
  • 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
  • R independently of one another are Ci-C ⁇ -alkyl or dC 8 -alkylcarbonyl
  • a 2 represents C 2 -C 8 alkenyl, dC 8 alkoxy, dC 6 haloalkoxy or one of the groups mentioned in A 1 ;
  • n 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
  • 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;
  • 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-C ⁇ -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
  • 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 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.
  • 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.
  • 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.
  • Halogen fluorine, chlorine, bromine and iodine
  • 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-difluoroe
  • 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-2-butenyl, 2-methyl- 2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-buten
  • 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-
  • 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.
  • d-C ⁇ -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
  • 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;
  • 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-
  • 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
  • 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 .
  • 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.
  • 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
  • 2 radicals R a bonded to adjacent C atoms can also represent a group OCH 2 O.
  • 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.
  • 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.
  • 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.
  • 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.
  • # is the point of attachment to the triazolopyrimidine backbone
  • 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 ;
  • 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.
  • 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
  • NR 8 R 9 represents NH 2 , NHCH 3 , NHC 2 H 5 ,
  • 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:
  • 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.
  • 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].
  • ether e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran
  • halogenated hydrocarbons such as dichloromethane
  • aromatic hydrocarbons such as toluene [cf. WO 98/46608; WO 02/48151].
  • 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.
  • 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.
  • 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.
  • 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
  • R ' stands for C 1 -C 4 alkyl, in particular for methyl or ethyl.
  • 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.
  • 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].
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • 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.
  • 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.
  • 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
  • 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.
  • natural stone powder e.g. kaolins, clays, talc, chalk
  • 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
  • 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.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil
  • coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
  • 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.
  • 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,
  • 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).
  • formulations include products for dilution in water, e.g.
  • Emulsifiable concentrates 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 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;
  • Water-dispersible and water-soluble granules 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;
  • WP, SP Water-dispersible and water-soluble powders: 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;
  • H dusts 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;
  • 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.
  • 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.
  • 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.
  • 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.
  • 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, triazolone diolone
  • 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
  • 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.
  • Example 65 Benzyl- [5-chloro-6- (2-chloro-6-fluorophenyl) [1, 2,4-triazolo] [1, 5-a] pyrimidin-7-yl] amine
  • Example 2 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 ,
  • 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.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • 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 undersides of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola.
  • 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.
  • 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.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • 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%.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne de nouveaux composés de triazolopyrimidine de formule (I), leur utilisation pour réguler les champignons pathogènes et des composés contenant lesdits pesticides agricoles de ce type en tant que constituants actifs. Dans la formule (I), X, Y, L, m, Ar, et A représentent les composés suivants : X représente halogène, cyano, alkyle C1-C4 ou haloalkyle C1-C4; Y représente halogène, alkyle C1-C4 ou haloalkyle C1-C4; L représente indépendamment un autre halogène, alkyle C1-C6, alcényle C2-C6, haloalkyle C1-C6, alcoxy C1-C6, haloalcoxy C1-C6, nitro, amino, NHR, NR2, cyano, S(=O)nA1 ou C(=O)A2; m représente 0, 1, 2, 3 ou 4; A représente une liaison chimique ou un groupe CR4R5; Ar représente phényle ou un groupe hétéroaromatique à 5 ou 6 éléments comprenant 1, 2, 3 hétéroatomes sélectionnés parmi O, S et N en tant que chaînon cyclique, ledit phényle et le groupe hétéroaromatique pouvant comprendre un noyau fusionné de benzol et pouvant présenter 1, 2, 3, 4 ou 5 substituants Ra. R1 à R3 sont également spécifiés dans la revendication 1.
EP05744598A 2004-05-17 2005-05-13 Composes triazolopyrimidine et leur utilisation pour reguler des champignons pathogenes Withdrawn EP1751162A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102004024349 2004-05-17
DE102004029446 2004-06-18
PCT/EP2005/005270 WO2005113555A1 (fr) 2004-05-17 2005-05-13 Composes triazolopyrimidine et leur utilisation pour reguler des champignons pathogenes

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JP (1) JP2007538028A (fr)
BR (1) BRPI0510804A (fr)
IL (1) IL179256A0 (fr)
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Publication number Priority date Publication date Assignee Title
WO2007113136A1 (fr) * 2006-03-30 2007-10-11 Basf Aktiengesellschaft Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes
EP3758696B1 (fr) * 2018-03-02 2026-02-25 The Trustees of the University of Pennsylvania Composés de [1,2,4]triazolo[1,5-a]pyrimidine et utilisation de ces derniers dans la stabilisation de microtubules

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TW224044B (fr) * 1991-12-30 1994-05-21 Shell Internat Res Schappej B V
TWI252231B (en) * 1997-04-14 2006-04-01 American Cyanamid Co Fungicidal trifluorophenyl-triazolopyrimidines
TW460476B (en) * 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
AU2001273062B2 (en) * 2000-06-30 2005-11-24 Wyeth Substituted-triazolopyrimidines as anticancer agents
DE10063115A1 (de) * 2000-12-18 2002-06-27 Bayer Ag Triazolopyrimidine
CA2479766A1 (fr) * 2002-03-21 2003-10-02 Basf Aktiengesellschaft Triazolopyrimidines fongicides, leur procede de production et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant

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Title
See references of WO2005113555A1 *

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JP2007538028A (ja) 2007-12-27
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BRPI0510804A (pt) 2007-11-06
WO2005113555A1 (fr) 2005-12-01

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