WO2007006722A1 - Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles - Google Patents

Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles Download PDF

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Publication number
WO2007006722A1
WO2007006722A1 PCT/EP2006/063968 EP2006063968W WO2007006722A1 WO 2007006722 A1 WO2007006722 A1 WO 2007006722A1 EP 2006063968 W EP2006063968 W EP 2006063968W WO 2007006722 A1 WO2007006722 A1 WO 2007006722A1
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WIPO (PCT)
Prior art keywords
alkyl
compounds
formula
het
methyl
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PCT/EP2006/063968
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German (de)
English (en)
Inventor
Oliver Wagner
Original Assignee
Basf Aktiengesellschaft
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Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2007006722A1 publication Critical patent/WO2007006722A1/fr

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    • 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

  • EP-A 613 900 is directed to 7-amino-1,2,4-triazolo [1,5-a] pyrimidine compounds and their use as fungicides. These compounds may have a secondary or tertiary amino group in the 7-position and an optionally substituted cycloalkyl ring or a heterocyclic group in the 6-position.
  • a heterocyclic group means a 3-6, preferably 5-6-membered ring system. At position 2, the compounds are not substituted.
  • WO 04/011467 is directed to 1, 2,4-triazolo [1, 5-a] pyrimidines, which can only carry a tertiary amino group in the 7-position, when an amino group is present at this position.
  • These compounds have in the ⁇ -position a 5- or 6-membered heterocyclyl group which may optionally be substituted pyrrolyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl or pyrimidinyl. At position 2, the compounds are not substituted.
  • the present invention is therefore based on the object to provide new compounds with better fungicidal activity and / or better crop compatibility.
  • the amines HNR 1 R 2 used in this process are generally commercially available or can be prepared by methods well known to those skilled in the art.
  • Another object of the present invention are compounds of the formula
  • Suitable solvents are, for example, aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the heteroarylmalonate (IV) in excess, based on the 3-amino-1, 2,4-triazole (V).
  • Preferred compounds of the present invention can be obtained starting from heteroarylmalonates of formula (IV) wherein Het is selected from the Het. Particularly preferred compounds of the present invention are further accessible starting from heteroarylmalonates (IV) wherein Het has the meanings given in Tables 1 to 135.
  • the reaction described above is usually carried out in the presence of strong bases.
  • R z is hydrogen
  • alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base.
  • R z is hydrogen
  • the reaction of the compound (VI) with compounds of the formula (VII) can be carried out in one stage or in two separate stages, in which latter case the intermediate (VI) is obtained in which R z is an alkoxycarbonyl group.
  • the reaction of compound (VI) with (VII) can be carried out analogously to the method described in J.
  • the reaction with Z-Y is preferably carried out in an inert solvent.
  • suitable solvents include ethers such as dioxane, diethyl ether, methyl tert-butyl ether and, preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane or dichloroethane, aromatic hydrocarbons such as toluene, and mixtures thereof.
  • Alkyl and the alkyl moieties in assembled groups saturated, straight-chain or branched hydrocarbon radicals.
  • the alkyl radicals are preferably (C 1 -C 8 ) -alkyl, in particular (C 1 -C 6) -alkyl radicals.
  • it may be preferable to use short-chain alkyl groups such as (C 1 -C 4) -alkyl, but it may also be advantageous to use longer-chain alkyl groups such as (Cs-Cs) -AlkVl.
  • short-chain alkenyloxy radicals such as (C 2 -C 4) -alkenyloxy
  • longer-chain alkenyloxy groups such as (Cs-C ⁇ J-alkenyloxy
  • Alkylthio Alkyl as defined above attached via an S atom.
  • heterocycles containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: for example, mono- and bicyclic heterocycles with 7
  • nitrogen-bonded 5-membered heteroaryl groups containing one to three nitrogen atoms as ring members, for example pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazole 1-yl, 1,2,4-triazol-1-yl, 1-tetrazolyl;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups, which in addition to carbon atoms may contain one to three or one to four nitrogen atoms as ring members, e.g. Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-
  • Het has at least one substituent which is in ortho-position to the point of attachment to the skeleton to which Het is bound.
  • the ortho-position L is fluorine, chlorine, (C 1 -C 2 ) -alkyl, such as methyl or ethyl, (C 1 -C 2 ) -fluoroalkyl, such as trifluoroalkyl or (C 1 -C 2 ) -alkoxy, such as methoxy.
  • L when L is bonded to a ring nitrogen of Het, it is particularly preferred that L each independently is
  • R 1 and R 2 together with the nitrogen atom to which they are attached, are 5- or 6-membered heteroaryl as defined above, which may be unsubstituted or substituted , preferably by 1, 2 or 3 groups R a .
  • the group NR 1 R 2 forms a pyrazole ring which is optionally substituted in the manner described above and especially by 1 or 2 of the following radicals: halogen, (Ci-C 4 ) alkyl or (Ci-C 4 ) -haloalkyl , in particular by 2 methyl groups or two trifluoromethyl groups in the 3,5-position.
  • X is halogen, in particular fluorine, chlorine or bromine, preferably chlorine.
  • Chloropyrazol-1-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table B.
  • Dimethylpyrazol-5-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table B.
  • Dimethylpyrazol-4-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table B.
  • Chloropyrazol-1-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table B.
  • Dimethylpyrazol-3-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table B.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • 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.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and 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, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances can be dissolved as such or in an oil or solvent, by means of wetting, adhesive, Dispersing or Emulgiermitttel be homogenized in water. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • Tetraconazole Tetraconazole, triadimenol, triadimefon, triticonazole;

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne des composés de 7-amino-6-hétéroaryl-1,2,4-triazolo[1,5-a]pyrimidine de formule (I) dans laquelle les substituants Het, R1, R1, X et Y ont les significations définies dans la description.
PCT/EP2006/063968 2005-07-13 2006-07-06 Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles WO2007006722A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005033146 2005-07-13
DE102005033146.7 2005-07-13

Publications (1)

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WO2007006722A1 true WO2007006722A1 (fr) 2007-01-18

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PCT/EP2006/063968 WO2007006722A1 (fr) 2005-07-13 2006-07-06 Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles

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WO (1) WO2007006722A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004011467A1 (fr) * 2002-07-29 2004-02-05 Hokko Chemical Industry Co., Ltd. Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004011467A1 (fr) * 2002-07-29 2004-02-05 Hokko Chemical Industry Co., Ltd. Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines

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