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EP1761544A1 - Composes tirazolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles - Google Patents

Composes tirazolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles

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Publication number
EP1761544A1
EP1761544A1 EP05761748A EP05761748A EP1761544A1 EP 1761544 A1 EP1761544 A1 EP 1761544A1 EP 05761748 A EP05761748 A EP 05761748A EP 05761748 A EP05761748 A EP 05761748A EP 1761544 A1 EP1761544 A1 EP 1761544A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
compounds
hydrogen
radicals
alkoxy
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.)
Withdrawn
Application number
EP05761748A
Other languages
German (de)
English (en)
Inventor
Carsten Blettner
Frank Schieweck
Jordi Tormo I Blasco
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
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1761544A1 publication Critical patent/EP1761544A1/fr
Withdrawn legal-status Critical Current

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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

  • the present invention relates to novel triazolopyrimidine compounds and their use for controlling harmful fungi and pesticides which contain such compounds as active ingredient.
  • EP-A 71792, US Pat. No. 5,994,360, EP-A 550113, WO-A 94/20501, EP-A 834 513, WO-A 98/46608 and WO 03/080615 describe fungicidally active triazolo [1, 5a] pyrimidines which in the 6-position of the Azolopyrimidinrings a where appropriate substituted phenyl group and in the 7-position NH 2 or carry a primary or secondary amino group.
  • the present invention is therefore based on the object to provide new compounds with better fungicidal activity and / or better crop compatibility.
  • R C 4 alkoxy or -C 2 -haloalkoxy X stands for halogen, cyano, Ci-C 4 alkyl, C 1 -C 4 haloalkyl, C;
  • W means oxygen or sulfur
  • Y is O-R 4 or a group NR 5 R 6 ;
  • A is a chemical bond or a group CR 7 R 8 ;
  • R independently of one another is C 1 -C 8 -alkyl or C 8 -C 8 -alkylcarbonyl;
  • a 1 is hydrogen, hydroxy, -C 8 alkyl, NH 2, (VCs-alkylamino or di- (C 1 -C 8 alkyl) amino group;
  • n 0, 1 or 2;
  • a 2 is C 2 -C 8 alkenyl, C 1 -C 8 -alkoxy, CrC 6 -haloalkoxy, hydrogen, hydroxyl, Ci-C 8 alkyl, NH 2, -C 8 -alkylamino or di (C 1 -C 8 -alkyl) amino;
  • n 0 or 1, 2, 3, 4 or 5;
  • R 1 is hydrogen, C r C 4 alkyl, formyl, CrGrAlkylcarbonyl or C r C 4 alkoxycarbonyl or together with R 2 is C 3 -C 6 alkylene, wherein 1 C atom is replaced by an oxygen atom or a sulfur atom can and if appropriate 1, 2, 3, or 4 C r C 4 alkyl groups and / or 1 or 2 radicals R can bear a; R a : halogen, OH, C 1 -C 4 -alkoxy or C r C 4 -alkoxycarbonyl;
  • R 4 is hydrogen, C r C 8 alkyl, Hyd Toxy-C 1 -C 4 alkyl, C r C 4 alkoxy-CrC 4 alkyl, hydro xy-Ci-C4-alkoxy-Ci-C 4 - alkyl, -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 halo-alkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 -cycloalkyl-CrC 4 alkyl, C 3 -C 6 Halo-cycloalkyl, C 3 -C 8 -cycloalkenyl, phenyl, phenyl-C 1 -C 4 -alkyl, where phenyl in the latter two radicals may have 1, 2 or 3 of the following substituents R d : R d : halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
  • R 4 is one of the radicals R 1 , R 2 , R 3 or R 7 is C 2 -C 6 alkylene, wherein 1 C atom may be replaced by an oxygen atom or a sulfur atom and optionally 1, 2, 3 or 4 radicals selected from halogen and C 1 -C 4 -alkyl and / or 1 or 2 radicals R a can carry;
  • R 5 , R 6 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or together with the nitrogen atom to which they are attached are form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from O, S and N as ring member and which optionally bears 1, 2, 3 or 4 CrCzrAlkyl groups,
  • radicals R 5 or R 6 with one of the radicals R 1 , R 2 , R 3 or R 7 is C 2 -C 6 -alkylene, where 1 C-atom may be replaced by an oxygen atom or a sulfur atom and optionally containing 1, 2, 3 or 4 radicals, now ⁇ selected from halogen and C r C 4 alkyl and / or 1 or 2 radicals R a may carry;
  • R 7 , R 8 are independently hydrogen, C r C 4 alkyl or C r C 4 alkoxy or one of R 7 or R 8 together with one of R 1 or R 2 is C 2 -C 6 alkylene group, where 1 C atom may be replaced by felatom an oxygen atom or a sulfuric and optionally containing 1, 2, 3, or 4 C r C 4 alkyl groups and / or 1 or 2 radicals R a can;
  • R 9 is hydrogen, C 1 -C 8 alkyl, formyl or C 1 -C 8 alkylcarbonyl;
  • R r C 4 alkyl or C 10 is hydrogen
  • R 11 , R 12 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or together with the nitrogen atom to which they are attached, form a saturated 5-, 6- or 7-membered Stickstoffhete- rocyclus having optionally a further O, S and N heteroatom selected as a ring member and optionally 1, 2, 3 or 4 C r C contributes 4 alkyl, where one of the radicals R 11 , R 12 can also be formyl, C 1 -C 8 -alkylcarbonyl or C 1 -C 8 -alkylthiocarbonyl;
  • R 13 is hydrogen, C r C 8 -alkyl, hydroxy-C r C 4 alkyl, Ci -C 4 -alkoxy-C 1 -C 4 alkyl, hydroxy-CrOralkoxy-CrOralkyl, -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-CrC 4 alkyl, C 3 -C 6 halocycloalkyl, C 3 -C 8 cycloalkenyl, phenyl Phenyl-C 1 -C 4 -alkyl, where phenyl in the latter two radicals may have 1, 2 or 3 of the abovementioned substituents R d ;
  • R 14 , R 15 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or together with the nitrogen atom to which they are attached , are a saturated 5-, 6- or 7-membered nitrogen heterocycle form, which optionally has a further, selected from O, S and N heteroatom as a ring member and optionally carries 1, 2, 3 or 4 CrC ⁇ alkyl groups;
  • R 16 is hydrogen or C 1 -C 4 -alkyl
  • the present invention thus relates to the triazolopyrimidine compounds of general formula I and their agriculturally acceptable salts.
  • the present invention furthermore relates to compositions for controlling 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 pure enantiomers or pure diastereomers or as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or diastereomers and mixtures thereof.
  • Salts which can be used agriculturally are, above all, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I.
  • the cations used are in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, if desired, one to may carry four C r C 4 -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (CrC 4 -alkyl) sulfonium and sulfoxonium ions
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of dC 4 alkanoic acids, preferably formate, acetate, Propionate and butyrate. They can be formed by reaction of I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • C r C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1 , 2-Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2 Trimethylpropyl, 1-ethyl-1-methylprop
  • Halo (gen) alkyl straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above, eg. B.
  • C r C 2 haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2.2 -Difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1 1,1-trifluoroprop-2-yl;
  • Alkenyl monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, up to 6 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-
  • Alkadienyl diunsaturated, straight-chain or branched Kohlenwasserstoff ⁇ radicals having 4 to 10 carbon atoms and two double bonds in any position, for example.
  • Alkynyl straight-chain or branched hydrocarbon groups having 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, i-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-
  • Cycloalkyl monocyclic, saturated hydrocarbon groups having 3 to 8, preferably up to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 8, preferably to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
  • Bicycloalkyl bicyclic hydrocarbon radical having 5 to 10 C atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, bicyclo 2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl and bicyclo [4.4.0] decyl;
  • Alkylamino for an alkyl group bonded via an NH group, in which alkyl is one of the abovementioned alkyl radicals having generally 1 to 6 and in particular 1 to 4 C atoms, such as methylamino, ethylamino, n-propylamino, isopropylamino, n- Butylamino and the like;
  • Dialkylamino for a radical of the formula N (AIKyI) 2 , wherein alkyl is one of the aforementioned ge alkyl radicals having usually 1 to 6 and in particular 1 to 4 carbon atoms, for.
  • alkyl is one of the aforementioned ge alkyl radicals having usually 1 to 6 and in particular 1 to 4 carbon atoms, for.
  • C 1 -C 4 -alkoxy for an oxygen-bonded alkyl group having 1 to 4 carbon atoms: z. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • C 1 -C 6 -alkoxy for C 1 -C 4 -alkoxy, as mentioned above, and z.
  • -C 4 -haloalkoxy a C r C 4 alkoxy as mentioned above, the, chlorine, bromine / or iodine and is preferably fluorine stituiert sub ⁇ by partially or fully by fluorine, ie.
  • d-Cs-haloalkoxy for C r C 4 haloalkoxy, as mentioned above, and z.
  • Alkenyloxy Alkenyl as mentioned above, which is bonded via an oxygen atom, for.
  • 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;
  • Alkylene for a linear saturated hydrocarbon chain having 2 to 6 and in particular 2 to 4 C atoms such as ethane-1, 2-diyl, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl or hexane-1, 6-diyl;
  • z. B mono- and bicyclic heterocycles having 7 Ringglie- the, containing in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro [1 H] 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 [1 H] azepine-1, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1, -2-, -3-, -4-,
  • X is halogen, especially chlorine, or C 1 -C 4 -alkyl, especially methyl, more preferably halogen and most preferably chlorine;
  • A is a chemical bond or CH 2 , in particular a chemical bond
  • R 1 is hydrogen or C 1 -C 4 -alkyl or R 1 forms with R 2 a linear or branched C 2 -C 6 -alkylene group, in particular a linear C 3 -C 4 -alkylene group;
  • R 2 is C 2 -C 6 -alkyl, trifluoromethyl or a group (CH 2 ) k -R b , where k is 1 or 2 and R b has the abovementioned meanings;
  • R 3 is hydrogen
  • n 1, 2, 3 or 4, in particular 1, 2 or 3;
  • L is halo, cyano, Ci-C 6 alkyl, -C 6 haloalkyl, C 1 -C 6 -alkoxy or CrCerAlkoxycarbonyl, in particular fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkyl, -C 4 haloalkyl, C 1 -C 4 -alkoxy or C
  • compounds I are preferred in which at least one group L is arranged in ortho position to the point of attachment to the triazolopyrimidine skeleton.
  • Y is a group OR 4 , in which R 4 has the meanings given above.
  • Y is a group OR 4 , in which R 4 with the radical R 2 is a C 2 -C 4 -alkylene group.
  • Y is a group NR 5 R 6 , wherein R 5 , R 6 have the meanings given above.
  • R 5 herein is H, C r C 4 alkyl or C 3 -C 4 alkenyl and especially methyl, ethyl, n-propyl or n-propenyl.
  • R 6 is in particular H, C r C 4 -alkyl or C 3 -C 4 -alkenyl and in particular H, methyl, ethyl or n-propyl.
  • R 5 and R 6 may also form, with the nitrogen atom to which they are bonded, a saturated 5- to 7-membered nitrogen heterocycle which may optionally have a further heteroatom selected from O, S and N as the ring member and which may optionally have 1 to 4 methyl groups: z.
  • Y is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl or 4-methylpiperazin-1-yl.
  • Y is a group NR 5 R 6 , wherein R 5 with the radical R 2 is a C 2 -C 4 -alkylene group and R 6 is hydrogen.
  • the phenyl group substituted by L m is the group of the formula
  • L 1 is fluorine, chlorine, CH 3 or CF 3
  • L 2 , L 4 are independently hydrogen, chlorine or fluorine, where L 4 may also be NO 2
  • L 3 is hydrogen, fluorine, chlorine, cyano, NO 2, C r C 4 alkyl, especially CH 3, C 1 -C 4 -alkoxy, in particular OCH 3, or CO (A 2) wherein A 2 is OH, C r is C 4 alkoxy, especially OCH 3 , NH 2 , C 1 -C 4 alkylamino
  • L 5 is hydrogen, fluorine, chlorine, or C 1 -C 4 -alkyl, especially CH 3 .
  • R 1 represents hydrogen or R 1 with R 2 forms a linear or branched C 2 -C 6 -alkylene group, in particular a linear C 3 -C 5 -alkylene group.
  • R 3 is in particular hydrogen.
  • R 2 is C 2 -C 6 -alkyl.
  • R 3 is in particular hydrogen.
  • R 1 then also represents hydrogen in particular.
  • those compounds of the formula I are particularly preferred in which R 3 is hydrogen, W is oxygen and Y is a group OR 4 , which has the abovementioned meanings and in particular the preferred meanings, and the radicals R 1 and R 2 those of the following amino acids: proline, piperic acid, leucine, isoleucine, methionine, phenylalanine, tyrosine and valine.
  • R 3 is hydrogen
  • W is oxygen
  • Y is a group OR 4 , which has the abovementioned meanings and in particular the preferred meanings
  • R 1 and R 2 those of the following amino acids: proline, piperic acid, leucine, isoleucine, methionine, phenylalanine, tyrosine and valine.
  • R 2 is a group (CH 2 ) k -R b , where k is 1 or 2 and R b has the meanings mentioned above.
  • R 3 is in particular hydrogen.
  • R 1 then also stands in particular for hydrogen.
  • R has the meanings b particular Float ⁇ phenyl, 4-hydroxyphenyl, 3,4-dihydroxyphenyl,-yl imidazol-4, indol-3-yl, 5-3 Hydroxindol yl, C r C 4 alkylthio, especially S-CH 3 , C r C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl.
  • Y in formula I is a group NR 5 R 6 , R 5 and R 6 independently of one another have the following meanings: H or C 1 -C 4 -alkyl.
  • R 9 particularly represents H, C r C 4 alkyl, C (O) H or CrC 4 alkylcarbonyl;
  • R 10 is in particular H or C 1 -C 4 -alkyl;
  • R 11 and R 12 are in particular H, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkyl (thiocarbonyl).
  • NR 11 R 12 is 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 13 is in particular C 1 -C 4 -alkyl.
  • R 14 is in particular H or C 1 -C 4 -alkyl.
  • R 15 is in particular H or C 1 -C 4 -alkyl.
  • R 16 is in particular H or C 1 -C 4 -alkyl.
  • Examples of preferred compounds of the formula I according to the invention are the enantiomers of the formulas IL and ID given in Tables 1 to 60 below, and the racemate of the formula IR, in which the variables R 1 , R 2 , R 3 and Y in each case jointly denote those described in one of the lines 1 to 814 of Table A has haben ben:
  • Table 1 Compounds of the formulas IL, ID and IR, in which X is chlorine, L m is 2-fluoro-6-chloro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 2 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,6-difluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 3 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,6-dichloro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 4 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2-fluoro-6-methyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 5 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,4,6-trifluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of the table A corresponds Table 6 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,6-difluoro-4-methoxy and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of the table A corresponds
  • Table 7 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is pentafluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 8 Compounds of the formulas ID, IL and IR, in which X is chlorine, L 17 , 2-methyl-4-fluoro be ⁇ and the combination of Y, R 1 , R 2 and R 3 is a compound in each case one row of Table A corresponds
  • Table 9 Compounds of the formulas ID, IL and IR, in which X denotes chlorine, L n , 2-trifluoromethyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 2-methoxy-6-fluoro mean 10 compounds of the formulas ID, IL and IR, in which X is chlorine, L m and the combination of for each compound corresponds to one line of Table A.
  • Table n Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2-chloro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 12 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2-fluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 13 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,4-difluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 14 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2-fluoro-4-chloro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 15 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2-chloro-4-fluoro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 16 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2,3-difluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 17 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,5-difluoro and the combination of Y, R 1 , R 2 and R 3 for a compound corresponds in each case to one row of Table A.
  • Table 18 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2,3,4-trifluoro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 19 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2-methyl and the combination of Y, R 1 , R 2 and R 3 for a compound corresponds in each case to one row of Table A.
  • Table 20 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,4-dimethyl and the combination of Y, R 1 , R 2 and R 3 for a compound corresponds in each case to one row of Table A.
  • Table 21 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2-methyl-4-chloro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds Table 22 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2-fluoro-4-methyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 23 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2,6-dimethyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 24 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2,4,6-trimethyl and the combination of Y, R 1 , R 2 and R 3 is a compound in each case one row of the table A corresponds
  • Table 25 Compounds of the formulas ID, IL and IR in which X is chlorine, L m is 2,6-difluoro-4-cyano and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of the table A corresponds
  • Table 26 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,6-difluoro-4-methyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 27 Compounds of the formulas ID, IL and IR, in which X is chlorine, L m is 2,6-difluoro-4-methoxycarbonyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one line in each case Table A corresponds
  • Table 28 mean the compounds of formulas ID, IL and IR, in which X is chlorine, L m is 2-trifluoromethyl-4-fluoro and the combination of Y, R 1, R 2 and R 3 for a compound corresponds in each case to one row of Table A
  • Table 29 mean the compounds of formulas ID, IL and IR, in which X is chlorine, L m is 2-trifluoromethyl-5-fluoro and the combination of Y, R 1, R 2 and R 3 for a compound corresponds in each case to one row of Table A
  • Table 30 mean the compounds of formulas ID, IL and IR, in which X is chlorine, L m is 2-trifluoromethyl-5-chloro and the combination of Y, R 1, R 2 and R 3 for a compound corresponds in each case to one row of Table A
  • Table 31 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-fluoro-6-chloro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 32 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-difluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 33 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-dichloro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 34 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-fluoro-6-methyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 35 Compounds of the formulas IL, ID and IR, in which X denotes methyl, L m 2, 4,6-trifluoro and the combination of Y, R 1 , R 2 and R 3 denotes a compound in each case one row of the table A corresponds
  • Table 36 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-difluoro-4-methoxy and the combination of one compound corresponds in each case to one row of Table A.
  • Table 37 Compounds of the formulas IL, ID and IR in which X is methyl, L m is pentafluoro and the combination of one compound corresponds in each case to one row of Table A.
  • Table 38 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-methyl-4-fluoro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 39 Compounds of the formulas IL, ID and IR in which X is methyl, L 171 is 2-trifluoromethyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 40 Compounds of the formula IL, ID and IR, in which X is methyl, L m is 2-methoxy-6-fluoro mean and 3 corresponds to the combination of Y, R 1, R 2 and R for each compound corresponds to one row of Table A
  • Table 41 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-chloro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 42 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-fluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of table A.
  • Table 43 Compounds of the formulas IL, ID and IR, in which X is methyl, L m is 2,4-difluoro and the combination of Y, R 1 , R 2 and R 3 for a compound corresponds in each case to one row of Table A.
  • Table 44 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-fluoro-4-chloro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 45 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-chloro-4-fluoro and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds Table 46 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,3-difluoro and the combination of Y 1 R 1 , R 2 and R 3 for a compound corresponds in each case to one row of Table A.
  • Table 47 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,5-difluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 48 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,3,4-trifluoro and the combination of Y, R 1 , R 2 and R 3 is a compound in each case one row of the table A corresponds
  • Table 49 Compounds of the formulas IL, ID and IR, in which X is methyl, L m is 2-methyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 50 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,4-dimethyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 51 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-methyl-4-chloro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 52 Compounds of the formulas IL, ID and IR, in which X is methyl, L m is 2-fluoro-4-methyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 53 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-dimethyl and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 54 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,4,6-trimethyl and the combination of Y, R 1 , R 2 and R 3 is a compound in each case one row of the table A corresponds
  • Table 55 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-difluoro-4-cyano and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of the table A corresponds
  • Table 56 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-difluoro-4-methyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one row of the table A corresponds
  • Table 57 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2,6-difluoro-4-methoxycarbonyl and the combination of Y, R 1 , R 2 and R 3 is a compound of one line in each case Table A corresponds
  • Table 58 Compounds of the formulas IL, ID and IR in which X is methyl, L m is 2-trifluoromethyl-4-fluoro and the combination of Y, R 1 , R 2 and R 3 for each compound corresponds to one row of Table A.
  • Table 59 mean the compounds of formulas IL, IR and ID, in which X is methyl, L m is 2-trifluoromethyl-5-fluoro and the combination of Y, R 1, R 2 and R 3 for a compound corresponds in each case to one row of Table A
  • Table 60 mean the compounds of formulas IL, IR and ID, in which X is methyl, L m is 2-trifluoromethyl-5-chloro and the combination of Y, R 1, R 2 and R 3 for a compound corresponds in each case to one row of Table A
  • heteroatom is bonded to the C atom of the carbonyl group.
  • preferred compounds of the formula I according to the invention are also the enantiomers of the formulas IL 1 and ID 'and the racemate of the formula IR 1 in which R 7 is hydrogen or methyl, X and L m are the meanings given in Tables 1 to 60 and the variables R 1 , R 2 , R 3 and Y in each case together have the meaning given in one of lines 1 to 814 of Table A:
  • Examples of preferred compounds of the formula I according to the invention are also the enantiomers of the formulas IL "and ID” and the racemate of the formula IR "in which L m and X are each the meanings given in Tables 1 to 60 and the variable Y is in each case the same in one of the lines 1 to 16 of Table A 1 has indicated meaning:
  • Table A 1 The compounds of the invention can be obtained in various ways.
  • the preparation of the compounds I, wherein X is halogen and W is oxygen (compounds LA) is generally carried out by reacting 5,7-dihalotriazolopyrimidines of the general formula II with aminocarboxylic acid derivatives of the general formula III according to the formula given in Scheme 1 method shown:
  • R 1 - R 3 , L, m and Y have the meanings given above.
  • Hal is halogen, especially chlorine.
  • Th is the reaction of Il with Aminocarbonklarederiva ⁇ advantageously at 0 0 C to 70 0 C, preferably from 10 0 C to 35 0 C., vor ⁇ preferably in the presence of an inert solvent such as ether, z.
  • an inert solvent such as ether, z.
  • dioxane, diethyl ether or especially tetrahydrofuran halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cp. WO 98/46608; WO 02/48151].
  • a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; It is also possible to use excess aminocarboxylic acid of the formula III as the base.
  • amino acid derivatives of the formula III are known and for the most part commercially available ver ⁇ or can be prepared by known methods for the preparation and derivatization of amino acids.
  • 5,7-Dihalogentriazolopyrimidines of the general formula II are known from the cited prior art or can be prepared in analogy to the methods described therein.
  • R 1 - R 3 , Hal, L, m and Y have the meanings given above.
  • X 1 is 4 -Halogenalkoxylat for cyanide, -C 4 alkoxylate or CrC.
  • the reaction is advantageously carried out in the presence of an inert solvent.
  • the cation M in formula IV has little significance; For practical reasons, ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are usually preferred.
  • the reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. heterocyclic. 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 given above.
  • Hal is 4 haloalkyl in particular chlorine or bromine
  • a 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidine VIII is prepared by reaction of 5-aminotriazole VI with the ketoester VII according to methods known per se [cf. Chem. Pharm. Bull., 9, 801, (1961)].
  • the 5-aminotriazole VI used is commercially available.
  • the preparation of the starting compounds VII is advantageously carried out under the conditions known from EP-A 10 02788.
  • halogenating agents are chlorination or bromination agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride used.
  • the reaction can be carried out in bulk or in the presence of a solvent. Typical reaction temperatures are from 0 to 150 ° C. or preferably from 80 to 125 ° C.
  • the reaction of the 7-Halogenotriazolopyrimidin IX with the amino carboxylic acid derivative of formula III is advantageously carried out ist ⁇ at 0 0 C to 70 0 C, in particular from 10 0 C to 35 0 C.
  • the reaction is preferably carried out in the presence of an inert solvent. agent, such as an ether, e.g. For example, dioxane, diethyl ether or tetrahydrofuran in particular, a halogenated hydrocarbon such as dichloromethane, an aromatic hydrocarbon such as toluene, xylene, etc. by [cf. WO 98/46608].
  • an ether e.g.
  • dioxane diethyl ether or tetrahydrofuran
  • a halogenated hydrocarbon such as dichloromethane
  • an aromatic hydrocarbon such as toluene, xylene, 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 amino carboxylic acid derivative of the formula III can also serve as a base.
  • compounds of the formula I.C can also be prepared by reacting compounds LA and malonic acid dialkyl esters of the formula X and subsequent decarboxylation by the method illustrated in Scheme 5 [cf. US 5994360].
  • R 1 - R 3 , L, m and Y have the meanings given above.
  • X '" is hydrogen, C r C 3 -alkyl or C r C 3 -haloalkyl and R is C 1 -C 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.
  • a malonic acid dialkyl ester of the formula X preferably in the presence of a base, or with the salt of X.
  • the reaction can be carried out in analogy to the method described in US 5994360.
  • Malonates X are known in the literature [J. At the. Chem. Soc., Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the cited literature.
  • the subsequent saponification of the ester XI is carried out under generally customary conditions [cf. US 5,994,360].
  • the alkaline or acidic saponification of the compounds XI may be advantageous.
  • the decarboxylation to I. C can already be carried out in whole or in part.
  • the decarboxylation is usually carried out at temperatures of 20 0 C to 180 0 C, preferably 50 0 C to 120 0 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 customary manner, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of Roh ⁇ products.
  • the intermediate and end products fall z. T. in the form of colorless or slightly brownish, viscous oils, which are freed from volatile fractions under reduced pressure and at moderately elevated temperature or purified. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • the compounds I are suitable as fungicides. They are distinguished by their outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. They are in part systemically effective and can be used in crop protection as foliar and soil fungicides.
  • the compounds I are also suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (eg wood, paper, dispersions for the paint, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Paecilomyces variotii in the protection of materials (eg wood, paper, dispersions for the paint, fibers or fabrics) and in the protection of stored products.
  • the compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidal treated effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • the compounds I can be converted into the customary formulations, for.
  • solutions emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; In each case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • aromatic solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg highly disperse silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl, Tri
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as Ke rosin or diesel oil, coal tar oils and oils plant or animal Ur ⁇ jump, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, Me ⁇ ethanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvent, eg. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium, fat, magnesium oxide, milled plastics, fertilizers such.
  • ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as Geidemehl, Baumrinden-, wood and nutshell, cellulose powder and other solid carriers.
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations include products for dilution in water, e.g. B.
  • DC Dispersible Concentrates
  • Emulsifiable Concentrates 15 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). Dilution in water results in an emulsion;
  • D Emulsions (EW, EO): 40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced by means of an emulsifier (Ultraturax) in water and brought to a homogeneous emulsion. Dilution in water results in an emulsion
  • E Suspensions 20 parts by weight of a compound according to the invention are comminuted with the addition of dispersants and wetting agents and water or an organic solvent in a stirred ball mill to give a fine active substance suspension. 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 by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble Granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient;
  • WP, SP Water-dispersible and water-soluble powders: 75 parts by weight of a compound according to the invention are mixed with dispersing and wetting agents and silica gel in a rotor-stator mill marry. Dilution in water results in a stable dispersion or solution of the active ingredient;
  • H dusts (DP) 5 parts by weight of a compound according to the invention are finely ground and intimately mixed with 95% finely divided kaolin. This gives a dusting agent;
  • I granules (GR, FG, GG, MG): 0.5 parts by weight of a compound according to the invention are finely ground and combined with 95.5% excipients. Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application;
  • the active compounds can be used as such, in the form of their formulations or the application forms prepared therefrom, eg. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
  • the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • wetting agents emulsions, pastes or oil dispersions
  • effective substance wetting agents, adhesives, dispersants or emulsifiers and any concentrates which are solvent or oil, which are suitable for dilution with water emulsion concentrates, pastes or oil dispersions.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions of the invention may also be present in the application form as fungicides together with other active ingredients, the z.
  • fungicides As with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • fertilizers When mixing the compounds I or the agents containing them in the application form as fungicides with other fungicides is obtained in many cases, an enlargement of the fungicidal spectrum of activity.
  • 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, imazali, metconazole, myclobutanil,
  • the active compounds were prepared as stock solution with 0.25% by weight of active compound in acetone or DMSO. This solution was 1 wt .-% emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) zuge ⁇ sets and diluted according to the desired concentration with water.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the active compounds were prepared as a stock solution, wherein 25 mg of active ingredient with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing on the basis of ethoxylated alkylphenols) in the volume ratio solvent-emulsifier from 99 to 1 up to a total volume of 10 ml and the mixture was then diluted with water to 100 ml.
  • This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.

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Abstract

L'invention concerne de nouveaux composés de triazolopyrimidine de formule générale (I) dans laquelle X désigne halogène, cyano, alkyle C<SUB>1</SUB>-C<SUB>4</SUB>, halogénure d'alkyle C<SUB>1</SUB>-C<SUB>4</SUB>, alcoxy C<SUB>1</SUB>-C<SUB>4</SUB> ou halogénure d'alcoxy C<SUB>1</SUB>-C<SUB>2</SUB>; W désigne oxygène ou soufre; Y désigne O-R<SUP>4</SUP> ou un groupe NR<SUP>5</SUP>R<SUP>6</SUP>; A désigne une liaison chimique ou un groupe CR<SUP>7</SUP>R<SUP>8</SUP>; et les variables L, R<SUP>1</SUP> à R<SUP>7</SUP> ont les significations mentionnées dans la revendication 1. L'invention concerne en outre l'utilisation des composés triazolopyrimidine de formule générale (I), de leurs tautomères et leurs sels compatibles sur le plan agricole, pour lutter contre des champignons phytopathogènes (= champignons nuisibles), ainsi qu'un procédé pour lutter contre des champignons phytopathogènes. Ledit procédé se caractérise en ce qu'il est prévu de traiter les champignons ou les matériaux à protéger de l'infestation par les champignons, comme les plantes, le sol ou les semences, avec une quantité efficace d'un composé de formule générale (I), un tautomère de (I) et/ou avec un sel compatible sur le plan agricole de (I) ou son tautomère.
EP05761748A 2004-06-25 2005-06-24 Composes tirazolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles Withdrawn EP1761544A1 (fr)

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AP2006003867A0 (en) 2006-12-31
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MXPA06013943A (es) 2007-03-15
EA200700007A1 (ru) 2007-08-31
BRPI0512557A (pt) 2008-03-25
AU2005256507A1 (en) 2006-01-05
PE20060112A1 (es) 2006-03-24
CR8795A (es) 2007-08-28
WO2006000436A1 (fr) 2006-01-05
IL180177A0 (en) 2007-06-03
ECSP067083A (es) 2007-02-28
TW200605792A (en) 2006-02-16
CN1972948A (zh) 2007-05-30
ZA200700630B (en) 2008-09-25
KR20070024646A (ko) 2007-03-02
UY28986A1 (es) 2006-01-31
US20070185099A1 (en) 2007-08-09
JP2008503538A (ja) 2008-02-07
CA2570578A1 (fr) 2006-01-05

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