EP1828191A2 - 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles - Google Patents

7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles

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Publication number
EP1828191A2
EP1828191A2 EP05816549A EP05816549A EP1828191A2 EP 1828191 A2 EP1828191 A2 EP 1828191A2 EP 05816549 A EP05816549 A EP 05816549A EP 05816549 A EP05816549 A EP 05816549A EP 1828191 A2 EP1828191 A2 EP 1828191A2
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EP
European Patent Office
Prior art keywords
het
compounds
formula
chlorine
hydrogen
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EP05816549A
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German (de)
English (en)
Inventor
Oliver Wagner
Thomas Grote
Joachim Rheinheimer
Barbara Nave
Reinhard Stierl
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BASF SE
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BASF SE
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Publication of EP1828191A2 publication Critical patent/EP1828191A2/fr
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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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • 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 7-amirio-6-hetaryl-1, 2,4-triazolo [1, 5-a] pyrimidine compounds and their use for controlling harmful fungi and crop protection agents containing at least one such compounds as an active ingredient.
  • EP-A 71 792, EP-A 550 113, EP-A 834 513 and WO-A 98/46608 describe fungi cid effective 1, 2,4-triazolo [1, 5-a] pyrimidines, which in the 6-position an optionally substituted phenyl ring, in the 5-position a halogen atom and in the 7-position carry an amino group.
  • WO 02/50077 describes comparable 1, 2,4-triazolo [1, 5-a] pyrimidines, which can also carry in the 6-position a heterocyclic radical. Compounds bearing a 6-membered heteroaromatic radical in this position are not described.
  • EP-A 613 900 describes f 1, 2,4-triazolo [1, 5-a] pyrimidine compounds which have a hydrogen atom or halogen atom in the 5-position and a secondary or in the 7-position having tertiary amino group. These compounds have in the 6-position a cycloalkyl or heterocyclyl radical, e.g. a 3-thienyl radical. Compounds bearing a 6-membered heteroaromatic radical in this position are not described.
  • 1,2,4-triazolo [1,5-a] pyrimidine compounds having in the 5-position a halogen atom, a cyano group, an alkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, an alkylamino group or an alkoxycarbonyl group.
  • these compounds may carry, inter alia, a tertiary amino group.
  • These compounds have in the 6-position a 5- or 6-membered heterocyclyl radical which is selected from unsubstituted or substituted pyrrolyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl and pyrimidinyl.
  • the 1,2,4-triazolo [1,5-a] pyrimidines known from the prior art are in some cases unsatisfactory with regard to their fungicidal activity or have undesired properties, such as a low crop tolerance.
  • the present invention is therefore based on the object to provide new compounds with better fungicidal activity and / or better crop compatibility.
  • the present invention thus relates
  • Het a 6-membered heteroaromatic radical which is selected from pyridinyl, pyridazinyl, pyrazinyl, 1, 2,4-triazinyl and 1, 3,5-triazinyl, wherein the 6-membered heteroaromatic radical 1, 2, 3 or 4 , preferably 1, 2 or 3 may have identical or different substituents L,
  • R 1, R 2 are independently hydrogen, C r C 8 alkyl, -C 8 haloalkyl, C 1 -C 8 -alkoxy, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 5 -C 10 bicycloalkyl, Ca-C ⁇ -halocycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 4 -C 0 -alkadienyl, C 2 -C 8 haloalkenyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 kinyloxy -alkyl, C 2 -C 8 haloalkynyl, NH 2, -C 8 alkylamino, di-Ci-C8 alkylamino, phenyl , Naph
  • R 1 and R 2 may also together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and has one, two or three further heteroatoms from the group Pe O, N and S may contain as ring member and / or one or more substituents, for example, 1, 2, 3 or 4 substituents, from the group halogen, d-Ce-alkyl, CrCe-haloalkyl, C 2 -C 6 3 -C 6 haloalkenyloxy, and can carry alkenyl, C 2 -C 6 haloalkenyl, Ci-C 6 alkoxy, -C 6 alkoxycarbonyl, -C 6 haloalkoxy, C 3 -C 6 kenyloxy Al, C / or wherein two substituents bonded to adjacent ring atoms may be C 1 -C 6 -alkylene, oxy-C 2 -C 4 -alkylene or oxy
  • R 1 and / or R 2 may carry one, two, three or four identical or different groups R a :
  • R a is cyano, nitro, hydroxy, carboxyl, dC 6 alkyl, -C 6 haloalkyl,
  • -C 6 alkylcarbonyl C 3 -C 6 cycloalkyl, -C 6 alkoxy, dC 6 haloalkoxy, d-Ce-alkoxycarbonyl, Ci-C 6 alkylthio, Ci-C 6 -alkylamino, di-C 1 -C 6 alkylamino, d-Ce-alkylaminocarbonyl,
  • R a in which the aliphatic, alicyclic or aromatic groups in R a may themselves be partially or completely halogenated or may carry one, two or three groups R b :
  • R b is cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkadienyl, alkenyloxy,
  • X is hydrogen, OH, halo, cyano, NR 3 R 4, C 8 alkyl, C 1 -C 8 -alkoxy, CrC ⁇ -alkylthio, CrC 8 alkylsulfinyl, C r C 8 alkylsulfonyl, C 2 -C 8 Alkenyl or
  • Y is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, -C 4 haloalkyl, C 1 -C 4 -alkoxy, CrCrAlkylthio, C 1 -C 4 - AI kylsu If i nyl, C r C 4 alkylsulfonyl, formyl , C r C 4 alkylcarbonyl, CrC.j alkoxycarbonyl, CONR 3 R 4 or C ⁇ haloalkoxy; in which
  • L is selected from halogen, cyano, hydroxy, cyanato (OCN), nitro, -C 8 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, -C 6 haloalkyl, C 2 -C 10 haloalkenyl , C 1 -C 6 -alkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6- Cycloalkoxy,
  • R 5 , R 6 are independently selected from hydrogen, C 1 -C 6 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkenyl where the last 5 radicals can be partially or fully halogenated or one, two, three or four radicals selected from cyano, C 1 -C 4 alkoximino, C 2 -C 4 alkenyloximino, C 2 -C 4 alkynyloximino or C 1 -C 4 alkoxy;
  • a 1 represents hydrogen, hydroxy, -C 8 -alkyl, amino, CrC 8 -alkylamino or di- (C 1 -C 8 alkyl) amino;
  • n 0, 1 or 2;
  • a 2 is C 2 -C 8 alkenyl, C r C 8 alkoxy, -C 6 haloalkoxy, C 2 -C 10 alkenyloxy, • C 2 -C 10 -alkynyloxy or one of said at A 1 groups is;
  • R 7, R 8, R 9, R 10, R 11, R 12 and R 13 are independently selected from hydrogen, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 -alkynyl, wherein the four last-mentioned radicals may have one, two, three, four, five or six radicals R a ; or
  • the invention furthermore relates to compounds of the general formula I and their salts, where R 1 , Het, X and Y have the abovementioned meanings and R 2 is an organic radical having 3 to 13 carbon atoms and one or more, for example Contains 1, 2 or 3 silicon atoms, and optionally 1 to 3 identical or different heteroatoms from the group oxygen, nitrogen and sulfur, and which is unsubstituted or 1, 2, 3 or 4 bears identical or different substituents which are halogen atoms and the substituents R a are selected.
  • the invention furthermore relates to compounds of the general formula I 1 in which Het, X and Y have the abovementioned meanings and R 1 and R 2, together with the nitrogen atom to which they are bonded, represent a heterocyclic ring having preferably 3 to 12 ring members which has one or more, for example 1, 2 or 3 silicon atoms and which is unsubstituted or carries 1, 2, 3 or 4 identical or different substituents which are selected from halogen atoms and the substituents R a .
  • the present invention furthermore relates to an agent for controlling harmful fungi, comprising at least one compound of the general formula I and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both the pure enantiomers or diastereomers and mixtures thereof.
  • Suitable compounds of general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • Agriculturally useful salts 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 ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion the desired one to four CrC 4 Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tri (C r C
  • 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 may be formed by reaction of I with an acid of the corresponding anion, preferably hydrochloric, hydrobromic, sulfuric, phosphoric or nitric acid.
  • d-Ce-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,
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above: especially d-Ca-haloalkyl, such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromomethyl, 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,
  • Alkenyl and the alkenyl moieties in alkenyloxy monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 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-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
  • Alkadienyl diunsaturated, straight-chain or branched hydrocarbon radicals having 4 to 10 carbon atoms and two double bonds in any position, e.g. 1, 3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, Hexa-1, 4-dien-3-yl, hexa-1, 4-dien-6-yl, hexa-1, 5-dien-1-yl, hexa-1, 5-dien-3-yl, hexa 1, 5-dien-4-yl, hepta-1, 4-dien-1-yl, hepta-1, 4-dien-3-yl, hepta-1, 4-dien-6-yl, hepta-1, 4-dien-3-yl, hepta-1, 4-dien-6-yl, hepta-1, 4-die
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals with
  • Alkynyl and the alkynyl moieties in alkynyloxy straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two triple bonds 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-hexyn
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 8, preferably 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopentene-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexene-4 yl and the like;
  • 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,
  • C 1 -C 4 -alkoxy for an oxygen-bonded alkyl group having 1 to 4 carbon atoms, for. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • d-Ce-alkoxy for C 1 -C 4 -alkoxy, as mentioned above, and z.
  • -C 6 -haloalkoxy for -C 4 -haloalkoxy, as mentioned above, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-Brompentoxy, 5-lodpentoxy, Undecafluorpentoxy, 6-Fluorhexoxy, 6-Chlorhexoxy, 6-Bromhexoxy, 6-lodhexoxy or dodecafluorohexoxy;
  • Alkenyloxy alkenyl as mentioned above, which is bonded via an oxygen atom, for example C 3 -C 6 alkenyloxy such as 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,
  • 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,
  • Alkylthio Alkyl as defined above attached via an S atom.
  • Alkylsulfinyl alkyl as defined above bonded through an SO group.
  • Alkylsulfonyl Alkyl as defined above attached via an S (O) 2 group.
  • heterocyclyl - five- or six-membered saturated or partially unsaturated heterocycle (hereinafter also heterocyclyl) containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: e.g. monocyclic saturated or partially unsaturated heterocycles 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, e.g.
  • 2-imidazolidinyl 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1, 2,4- Thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiazolidin-2-yl, 1, 3,4-triazolidine 2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydro-thienyl 2-yl, 2,3-dihydro-thien-3-yl,
  • tetra- and hexahydroazepinyl such as 2,3,4,5-tetrahydro [1 H] azepine-1- l -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepine-2-, -3-, -A-, -5-, -6- or -7-yl , 2,3,4,7-tetrahydro [1 H] azepine-1- l -2-, -3-, -A-, -5-, -6- or -7-yl, 2,3,6, 7-tetrahydro [1 H] azepine-1, -2, -3, -A, 5, 6 or 7-yl,
  • Hexahydroazepine-1 -, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2, -3-, -A-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1H] oxepin-2, -3, -A-, -5-, -6- or -7- yl, 2,3,6,7-tetrahydro [1 H] oxepin-2-, -3-, -A-, -5-, -6- or -7-yl, hexahydroazepin-1 -, -2-, -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyI,
  • Alkylene divalent unbranched chains of 1 to 6 CH 2 groups, eg CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2I CH 2 CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 J
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • organic radicals which contain 3 to 13 carbon atoms and one or more silicon atoms and optionally 1 to 3 hetero or heteroatoms from the group consisting of oxygen, nitrogen and sulfur, and which are unsubstituted or 1 to 4, the same or different SiMe 3 , SiMe 2 Et, SiMe 2 CHMe 2 , SiMe 2 CH 2 CHMe 2 , SiMe 2 CH 2 CMe 3 , SiMe 2 OCHMe 2 , SiMe 2 OCH 2 CHMe 2 , CH 2 SiMe 3 , CH 2 SiMe 2 Et, CH 2 SiMe 2 CHMe 2 , CH 2 SiMe 2 CH 2 CHMe, CH 2 SiMe 2 OMe, CH 2 SiMe 2 OCHMe 2 , CH 2 SiMe 2 OCH 2 CHMe 2 , CHMeSiMe 3 , CHMeSiMe 2 OMe, (CH 2 ) 2 SiMe 3 , (CH 2 J 2 SiMe 2 Et,
  • fungicidal activity preference is given to compounds of the general formula I in which at least one of the radicals R 1 or R 2 is different from hydrogen. Preferred among these are compounds of the general formula I in which R 1 is different from hydrogen and R 2 is hydrogen. Equally preferred are compounds of the general formula I in which R 1 and R 2 are different from hydrogen. Among these, preference is given to compounds of the general formula I in which R 2 is C 1 -C 4 -alkyl, especially methyl or ethyl.
  • R 1 is in particular C 1 -C 6 -alkyl, C 2 -C 6 -alkynyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, which is 1, 2, 3 or 4-times may be substituted by halogen or C 1 -C 4 alkyl, or C 1 -C 8 haloalkyl.
  • a particularly preferred embodiment relates to compounds of the general formula I in which R 1 is a group B:
  • Z 1 is hydrogen, fluorine or C r C 4 fluoroalkyl
  • Z 2 is hydrogen or fluorine
  • R 16 is hydrogen or methyl.
  • R 1 is C 3 -C 6 -cycloalkyl, which may be substituted by dC 4 alkyl.
  • R 1 and R 2 together with the nitrogen atom to which they are attached represent saturated or monounsaturated, in particular 5 or 6-membered heterocyclyl, as defined above.
  • R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted piperidinyl, morpholinyl or thiomorpholinyl ring, especially a piperidinyl ring.
  • Iyi are unsubstituted or substituted by 1, 2 or 3 substituents R a, where preferred substituents on R a heterocyclyl selected from halogen, C r C 4 alkyl, and -C 4 haloalkyl.
  • R a substituents on R a heterocyclyl selected from halogen, C r C 4 alkyl, and -C 4 haloalkyl.
  • substituents on R a heterocyclyl selected from halogen, C r C 4 alkyl, and -C 4 haloalkyl are particularly preferred compounds I are those where R 1 and R 2 together with the nitrogen atom to which they are connected Ge, a 4-methylpiperidine, 4-Trifluormethylpiperidinring, a morpholine ring or a 3,4-dimethylpiperidine, and specifically a 4 -Methylpiperidinring or form a 3,4-dimethylpiperidine ring.
  • a further particularly preferred subject of the invention are compounds I in which R 1 and R 2 together with the nitrogen atom to which they are attached represent 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 2 trifluoromethyl groups in the 3,5-position.
  • X is in a first embodiment of the invention, hydrogen, OH, halo, cyano, NR 3 R 4, C 1 -C 8 -alkoxy, CrC 8 alkylthio, d-C ⁇ -alkylsulfinyl, C r C 8 alkylsulfonyl, wherein the 4 last-mentioned radicals may be partially or fully halogenated and / or one, two or three substituents selected from nitro, cyano, -C 2 -alkoxy, CrC 4 -Alkythio, C 1 -C 4 alkoxycarbonyl, amino, -C 4 alkylamino and Di-Ci -C 4 -alkylamino, and wherein R 3 and R 4 independently of one another have the meanings given for R 1 or R 2 .
  • X in this embodiment in particular halogen, cyano, Ci-C 4 alkoxy or -C 2 haloalkoxy, more preferably halogen, cyano or C 1 -C 2 -alkoxy, such as chlorine, cyano, methoxy or ethoxy, particularly preferably Halogen and especially for chlorine.
  • X is C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl, where the 3 radicals can be partially or completely halogenated and / or one, two or three halogens three substituents selected from nitro, cyano, C 1 -C 2 -alkoxy,
  • CrC 4 alkoxycarbonyl amino, C ⁇ C ⁇ alkylamino and di-C 1 -C 4 alkylamino.
  • X in this embodiment in particular C 1 -C 4 -AIk ⁇ 1 -C 4 haloalkyl, more preferably C 1 -C 2 -AIk ⁇ as methyl or ethyl, or -C 2 -haloalkyl such as fluoromethyl, chloromethyl, Brommethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl, and especially for methyl.
  • X is 2 -haloalkoxy particular halogen, cyano, C 1 -C 4 -AIRyI, -C 4 haloalkyl, C 1 -C 4 -alkoxy or CrC.
  • compounds of general formula I are preferred in which X is halogen, Ci-C 2 alkyl, cyano or C 1 -C 2 -alkoxy, such as chlorine, methyl, cyano, methoxy or ethoxy.
  • X is especially halogen and especially chlorine.
  • Particular preference is also given Compounds of the formula I in which X is CN, C 1 -C 4 -alkoxy or C 1 -C 4 -alkynio, especially CN, methoxy or methylthio.
  • Y is preferably hydrogen, halogen, cyano, -C 4 alkyl, C r C 4 haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, CrC 4 alkylsulfinyl,
  • Preferred substituents L on Het are halogen, cyano, nitro, NH 2, CRCE-alkylamino, di-C 1 -C ⁇ -alkylamino, -C 6 alkyl, CrC 6 -HaIogenalkyl, C 1 -C 6 -alkoxy, -C 6 alkylamino , Di-CrC 6 -alkylamino, NH-C (O) -CrC 6 -alkyl, a
  • a 2 has the abovementioned meanings and is preferably C 1 -C 4 -alkoxy, NH 2, C 4 alkylamino or di-C 1 -C 4 alkylamino.
  • L groups are independently selected from fluorine, chlorine, bromine, iodine, cyano, nitro, -C 4 alkyl, specially methyl, -C 4 haloalkyl, C 1 -C 4 -alkoxy and CrC 4 alkoxycarbonyl, especially preferably fluorine, chlorine, C 1 -C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -fluoroalkyl, such as trifluoromethyl, C 1 -C 2 -alkoxy, such as methoxy, or C 1 -C 2 -alkoxycarbonyl, such as methoxycarbonyl.
  • At least one of the heteroatoms of the 6-membered heteroaromatic radical Het and / or a substituent L in ortho position to the binding site of Het is arranged on the triazolopyrimidine unit.
  • Preferred substituents L in the ortho position are fluorine, chlorine, bromine, iodine, -C 2 -alkyl such as methyl or ethyl, -C 2 fluoroalkyl such as trifluoromethyl and C 1 -C 2 -alkoxy such as methoxy, furthermore CN, methyl methylthio, Methylsulfinyl, methylsulfonyl, nitro or methoxymethyl.
  • substituents L in the ortho position are CN, methyl, methoxy and methylthio
  • a preferred embodiment of the invention relates to compounds of general formula I 1 wherein Het is pyridinyl which optionally has 1, 2 or 3 substituents L.
  • L has in particular the meanings given as preferred.
  • the residue in the 3-position is selected from chlorine, bromine, iodine, C 1 -C 2 -alkyl such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro and methoxymethyl, and is specially chlorine.
  • the radical is selected in the 5-position by fluorine, chlorine, bromine, cyano, nitro, -C 2 -alkyl such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, -C 2 alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl , CONH 2 , C 1 -C 2 -alkylaminocarbonyl such as methylaminocarbonyl or ethylaminocarbonyl, C 1 -C 2 -alkylcarbonyl such as acetyl and C (S) NH 2 .
  • Het is one of the following radicals of the formulas HeM, Het-2 or Het-3,
  • L 1 represents chlorine, bromine, iodine, -C 2 -alkyl such as methyl or ethyl, C r C 2 alkoxy such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro or methoxymethyl, especially is chlorine, and
  • L 2 represents fluorine, chlorine, bromine, iodine, cyano, nitro, CrQrAlkyl such as methyl or ethyl, C 1 -C 2 -alkoxy WJE methoxy, -C 2 alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl, CONH 2, -C 2 -alkylaminocarbonyl such as methylaminocarbonyl or Ethylaminocarbonyl, C r C 2 alkylcarbonyl such as acetyl or C (S) NH 2 .
  • Het is 3-pyridinyl which optionally has 1, 2 or 3 substituents L.
  • Preferred among these are compounds having a substituent L in the 2-position (ortho to the point of attachment and to the nitrogen of the pyridine ring) and / or a substituent L in the 4-position of the pyridine ring (ortho to the point of attachment and para to the nitrogen of the pyridine ring) exhibit.
  • Het is one of the following radicals of the formulas Het-4, Het-5, Het-6, Het-7 or Het-8,
  • L 3 represents fluorine, chlorine, bromine, iodine, cyano, nitro, -C 2 -alkyl such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, -C 2 alkoxycarbonyl such as methoxycarbonyl or
  • L 4 represents fluorine, chlorine, bromine, iodine, C r C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro or methoxymethyl,
  • L 5 represents fluorine, chlorine, bromine, iodine, C r C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -alkoxy, such as
  • L 6 and L 7 independently of one another have one of the following meanings: fluorine, chlorine, bromine, iodine, C r C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro or methoxymethyl.
  • Het is 4-pyridinyl which optionally has 1 or 2 substituents L.
  • preferred are compounds having a substituent L in the 3-position and / or a substituent L in the 5-position of the pyridine ring.
  • Het is one of the following radicals of the formulas Het-9 or Het-10,
  • L 8 represents fluorine, chlorine, bromine, iodine, C 1 -C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -alkoxy, such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro or methoxymethyl,
  • L 9 represents fluorine, chlorine, bromine, iodine, -C 2 -alkyl such as methyl or ethyl, C r C 2 alkoxy such as methoxy, methylthio, methylsulfinyl, methylsulfonyl, nitro or methoxymethyl, and
  • L 10 represents fluorine, chlorine, bromine, iodine, cyano, nitro, C r C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -alkoxy such as methoxy, -C 2 alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl, CONH 2, -C 2 -Alkylaminocarbonyl such as methylaminocarbonyl or ethylaminocarbonyl, C 1 -C 2 -alkylcarbonyl such as acetyl or C (S) NH 2 .
  • a further preferred embodiment of the invention relates to compounds of the general formula I, wherein Het is 2-pyrazinyl, which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is 3-pyridazinyl which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is 1,3,5-triazinyl which optionally has 1 or 2 substituents L.
  • R 5 and R 6 independently of one another are preferably hydrogen or C r C 4 alkyl.
  • R 7 is preferably hydrogen or in particular CrC ⁇ -alkyl.
  • R 8 and R 9 independently of one another are preferably hydrogen or C r C 6 alkyl.
  • R 10 , R 11 , R 12 and R 13 are preferably independently selected from hydrogen or C 1 -C 6 -AIRyI.
  • a 1 is preferably hydrogen, C 1 -C 6 -alkyl or amino.
  • the index n is preferably 0, 1 or 2.
  • a 2 is preferably C 1 -C 4 -alkoxy, NH 2 , CVC ⁇ alkylamino or di-C 1 -C 4 -alkylamino.
  • Examples of preferred compounds of the general formula I are the compounds I compiled in the following Tables 1 to 11430.
  • the groups mentioned in Tables 1 to 1430 for a substituent Het are also considered separately, independently of the combination in which they are mentioned , a particularly preferred embodiment of the substituent in question.
  • Very particularly preferred compounds of the formula I are those in which Het is 3-chloropyridin-2-yl, 3,5-dichloropyridin-2-yl or 2,4-dichloro-6-methylpyridin-3-yl.
  • Het 5-methoxycarbonylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 4-methylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 3-methylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 3-Ethy Ipyrid i n-2 -y I and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 6-methylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 5-trifluoromethylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 3-trifluoromethylpyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 5-fluoropyridin-2-yl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 3-fluoropyridin-2-yl and the combination of R 1 and R 2 for a corresponds in each case to one line of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Y, R 1 , R 2 and Het have the meanings given above.
  • Hal is halogen, preferably chlorine or bromine.
  • dihydroxytriazolopyrimidines of the formula II are converted into the dihalogen compounds of the formula III by analogy with the cited prior art or methods described in WO-A 94/20501 by reaction with a halogenating agent [HAL].
  • the halogenating agent used is advantageously a phosphorus oxyhalide or a phosphorus (V) halide, such as phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride with phosphorus pentachloride.
  • This reaction of II with the halogenating agent is usually carried out at 0 ° C. to 150 ° C., preferably at 80 ° C.
  • reaction may be carried out in bulk or in an inert solvent, for example a halogenated hydrocarbon, such as dichloromethane, dichloroethane or an aromatic hydrocarbon, such as. for example, toluene, xylene, and the like, or in a mixture of the aforementioned solvents.
  • a halogenated hydrocarbon such as dichloromethane, dichloroethane or an aromatic hydrocarbon, such as. for example, toluene, xylene, and the like, or in a mixture of the aforementioned solvents.
  • reaction of III with amines IV is carried out in analogy to the methods described in the cited prior art or in WO 98/46608 and is advantageously at temperatures in the range of 0 0 C to 70 0 C, preferably 10 0 C to 35 0 C. carried out.
  • the reaction is preferably carried out in an inert solvent, for example an ether, such as dioxane, diethyl ether, diisopropyl ether, tert-butyl methyl ether or, in particular, tetrahydrofuran, a halogenated hydrocarbon, such as dichloromethane.
  • an ether such as dioxane, diethyl ether, diisopropyl ether, tert-butyl methyl ether or, in particular, tetrahydrofuran, a halogenated hydrocarbon, such as dichloromethane.
  • organomethane dichloroethane or an aromatic hydrocarbon such as toluene, xylene and the like or in a mixture of the aforementioned solvents.
  • a base such as tertiary amines, for example triethylamine, biscyclohexylmethylamine, pyridine, picoline or inorganic bases, such as potassium carbonate, is preferred; Excess amine of the formula IV can also serve as a base.
  • the amines IV are generally commercially available or can be prepared by known methods.
  • the compounds of the general formulas II and III and their agriculturally acceptable salts are novel and likewise the subject of the present invention.
  • the compounds of formulas II and III and their agriculturally acceptable salts are also distinguished by their effectiveness against plant-damaging fungi. Their use for controlling fungi which are pathogenic to plants and the corresponding process for this purpose and crop protection agents which comprise at least one compound of the formulas II or III are therefore likewise the subject matter of the present invention.
  • Dihydroxytriazolopyrimidines of the formula II can be prepared in analogy to the cited prior art or in Adv. Het. Chem. Vol. 57, p. 81 ff. (1993) by reacting a 3-amino-2H-1,2,4-triazole V with correspondingly substituted hetarylmalonates of the formula VI.
  • R is alkyl, preferably C 1 -C 6 -alkyl, in particular methyl or ethyl.
  • Het and Y have the meanings given above.
  • This reaction is usually carried out at temperatures from 80 0 C to 250 0 C, preferably from 120 0 C to 180 0 C, without solvent or in an inert organic solu- solvents in the presence of a base [cp. EP-A 770 615] or in the presence of acetic acid under the conditions described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993) known conditions.
  • Suitable solvents are 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 reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide, N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned. If appropriate, it is also possible to add catalytic amounts of acids, such as p-toluenesulfonic acid, acetic acid or propionic acid.
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal hydrogencarbonates, organometallic compounds, in particular alkali metal alkyls, alkyl magnesium halides and alkali metal and alkaline earth metal alkoxides and Dimethoxymagnesium, also organic bases, eg tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethyl-aminopyridine and bicyclic amines into consideration. Particularly preferred are tertiary amines such as diisopropylethylamine
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • 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 malonate VI in an excess based on the triazole V.
  • Hetarylmalonate of the formula VI are some new and also subject of the present invention, namely when Het 1, 2 or 3 substituents which are independently selected from hydroxy, cyanoato (OCN), CrC 8 alkyl, C 2 -Ci o-alkenyl , C 2 -C 10 alkynyl, -C 6 haloalkyl, C 2 -C 10 haloalkenyl, Ci-C 6 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 10 alkynyloxy, CrC 6 haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkoxy, C 1 -C 8 -alkoximinoalkyl, C 2 -C 10 -alkenyloximinoalkyl, C 2 -C 10 -alkynyloximinoalkyl, C
  • Hetarylmalonates of the formula VI can be prepared from hetaryl compounds of the formula VII by reaction with one or two equivalents of a carbonic acid ester or a chloroformate (compound VIII) in the presence of a strong base (see Scheme 3).
  • R z is hydrogen or a C 1 -C 4 alkoxycarbonyl group.
  • Q is halogen or C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. Het has the meanings given above and R is C 1 -C 4 -alkyl.
  • R z H at least 2 equivalents of the compound VIII must be used in order to achieve a complete conversion of VII.
  • the reaction shown in Scheme 3 is usually carried out in the presence of strong bases.
  • R z is hydrogen, it is usual to use alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base. In this case, the base will be used at least equimolar, based on the compound VII, in order to achieve a complete conversion.
  • R z is an alkoxycarbonyl group, it is preferable to use an alkali metal alcoholate, for example sodium or potassium ethanolate, sodium or potassium butoxide, sodium or potassium methoxide as the base.
  • reaction of VII with VIII can be carried out in one stage or in two separate stages, in which case the compound VII is obtained as an intermediate in which R z is an alkoxycarbonyl group. Otherwise, the reaction of VII with VIII can be carried out analogously to the method described in J. Med. Chem. 25, 1982, p. 745.
  • malonates of the formula VI is also advantageously achieved by reaction of corresponding bromo-hetaryl compounds Br-Het with dialkyl malonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].
  • X 1 is H 1 -C 4 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl, or represents a radical corresponding halogenated, for example, according to the illustrated in Scheme 4 Synthesis be prepared.
  • Y, R 1 , R 2 and Het have the meanings given above.
  • Hal is halogen, preferably chlorine or bromine.
  • X ' is H, C 1 -Ce-Al kVl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl or a corresponding halogenated radical and R is C 1 -C 4 -alkyl.
  • the reactions shown in Scheme 4 can be carried out in analogy to the reactions explained in Schemes 1 and 2.
  • Some of the compounds of the formula VIa are new and are also the subject of the present invention, namely when Het has 1, 2 or 3 substituents which are independently of one another cyano, hydroxyl, cyanoato (OCN), C 1 -C 8 -alkyl, C 2 -C 10 - alkenyl, C 2 -Cio-alkynyl, C r C 6 haloalkyl, C 2 -C 10 haloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 1 o-alkenyloxy, C 2 -C 10 alkynyloxy, d -C 1 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -cycloalkoxy, C 2 -C 10 -alkenyloxycarbonyl,
  • the compounds of the formula VIa can be prepared analogously to standard processes in the sense of a mixed ester condensation from the corresponding hetaryl acid esters by reaction with the corresponding aliphatic C 2 -C 5 carboxylic acid alkyl esters such as ethyl acetate, ethyl propionate, ethyl butyrate or ethyl valerate or with a reactive derivative thereof, for example an acid chloride or an acid anhydride, in the presence of a strong base, for example an alcoholate, an alkali metal amide or an organolithium compound, for example in analogy to that described in J. Chem. Soc. Perkin Trans 1967, 767 or Eur. J. Org. Chem. 2002, p. 3986.
  • the compounds of the formula IX are, depending on the group X 'to be introduced, an inorganic cyanide, an alkoxylate, a thiolate or a haloalkoxylate.
  • the reaction is advantageously carried out in an inert solvent.
  • the cation M 1 in formula IX has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred (Scheme 5).
  • reaction temperature is 0 to 120 0 C 1 is preferably at 10 to 40 0 C [cp. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Suitable solvents include ethers, such as dioxane, diethyl ether,
  • halogenated hydrocarbons such as dichloromethane or dichloroethane
  • aromatic hydrocarbons such as toluene and mixtures thereof.
  • Compounds of formula I in which X is C 1 -C 8 -alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl or C 2 C 8 -haloalkynyl can advantageously be prepared by reacting compounds I in which X is halo with organometallic compounds X a -Mt, in which X a is C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl or C 2 -C 8 haloalkynyl and Mt represents lithium, magnesium or zinc.
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (I) iodide.
  • the reaction is carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the temperatures required for this purpose are in the range of -100 to +100 0 C and especially in the range of -80 0 C to +40 0 C. Processes are known, for. B. from the cited prior art (see, for example, WO 03/004465)
  • compounds of the formula I in which X is C 1 -C 8 -alkyl can also be prepared by reacting compounds I in which X is halogen, in particular chlorine, with malonates of the formula X.
  • This synthetic route is shown in Scheme 6.
  • X is hydrogen or C 1 -C 3 -alkyl and RC 1 -C 4 -alkyl.
  • the compounds I are converted into compounds of the formula XI, which are subsequently decarboxylated to compounds I after saponification [cf. US 5,994,360].
  • the subsequent saponification of the ester XI is carried out under generally customary conditions. Depending on the various structural elements, the alkaline or acidic saponification of the compounds Xi may be advantageous.
  • the decarboxylation to I already take place 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. Butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone,
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are z.T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature from volatile constituents. 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 outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, D ⁇ uteromycetes, Oomycetes and Bassidiomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. They are particularly important for the control of a variety of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soy, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers. Beans, tomatoes, potatoes and cucurbits, as well as the seeds of these plants.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • Cochliobolus species on corn, cereals, rice e.g., Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice
  • Gaeumanomyces graminis on cereals Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice)
  • the compounds (I) are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Gera tocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds of formula (I) may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods.
  • 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 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.
  • Seed treatment may be by techniques known to those skilled in the art such as Seed Dressing, Seed Coating, Seed Dusting, Seed Soaking and Seet Pelleting.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg are used.
  • a further subject of the invention is therefore seed comprising a compound of the formula (I) according to the invention in an amount of from 1 to 1000 g per 100 kg.
  • 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 usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case 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 compound with solvents and / or excipients, if desired with use of emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • Aromasoles e.g., Solvesso products, xylene
  • paraffins e.g., petroleum fractions
  • alcohols e.g., methanol, butanol, pentanol, benzyl alcohol
  • ketones e.g., cyclohexanone, gamma-butyrolactone
  • NMP pyrrolidones
  • NOP 1 acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals e.g., kaolins, clays, talc, chalk
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, Alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, Nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether
  • mineral oil fractions of medium to high boiling point such as kerosine 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 kerosine 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 derivative
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, chalk 1 chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, chalk 1 chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as

Landscapes

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

Abstract

L'invention concerne de nouvelles 7-amino-6-hétaryl-1,2,4-triazolo[1,5-a]pyrimidines et leurs sels utilisables en agriculture, l'utilisation de ces composés pour lutter contre des champignons nuisibles, ainsi que des produits phytosanitaires contenant au moins un de ces composés comme composant actif. Ces nouvelles 7-amino-6-hétaryl-1,2,4-triazolo[1,5-a]pyrimidines sont représentées par la formule générale (I), dans laquelle les substituants R<SUP>1</SUP>, R<SUP>2</SUP>, Het, X et Y ont les significations suivantes : Het représente un groupe hétéroaromatique à 6 membres choisi parmi les groupes pyridinyle, pyridazinyle, pyrazinyle, 1,2,4-triazinyle et 1,3,5-triazinyle, ce groupe hétéroaromatique à 6 membres pouvant présenter 1, 2 ou 3 substituants L identiques ou différents, R<SUP>1</SUP> et R<SUP>2</SUP> représentent indépendamment un atome d'hydrogène ou un groupe alkyle C<SUB>1</SUB>-C<SUB>8</SUB>, halogénoalkyle C<SUB>1</SUB>-C<SUB>8</SUB>, alcoxy C<SUB>1</SUB>-C<SUB>8</SUB>, cycloalkyle C<SUB>3</SUB>-C<SUB>8</SUB>, cycloalcoxy C<SUB>3</SUB>-C<SUB>8</SUB>, bicycloalkyle C<SUB>5</SUB>-C<SUB>10</SUB>, halogénocycloalkyle C<SUB>3</SUB>-C<SUB>8</SUB>, alcényle C<SUB>2</SUB>-C<SUB>8</SUB>, alcényloxy C<SUB>2</SUB>-C<SUB>8</SUB>, alcadiényle C<SUB>4</SUB>-C<SUB>10</SUB>, halogénoalcényle C<SUB>2</SUB>-C<SUB>8</SUB>, cycloalcényle C<SUB>3</SUB>-C<SUB>8</SUB>, halogénocycloalcényle C<SUB>3</SUB>-C<SUB>8</SUB>, alcynyle C<SUB>2</SUB>-C<SUB>8</SUB>, alcynyloxy C<SUB>2</SUB>-C<SUB>8</SUB>, halogénoalcynyle C<SUB>2</SUB>-C<SUB>8</SUB>, NH<SUB>2</SUB>, alkylamino C<SUB>1</SUB>-C<SUB>8</SUB>, di-C<SUB>1</SUB>-C<SUB>8</SUB>-alkylamino, phényle ou naphtyle ou un hétérocycle saturé, partiellement insaturé ou aromatique à cinq ou six membres, X représente un atome d'hydrogène, un atome d'halogène ou un groupe OH, cyano ou alkyle C<SUB>1</SUB>-C<SUB>4</SUB> et similaire et Y représente un atome d'hydrogène, un atome d'halogène ou un groupe cyano ou alkyle C<SUB>1</SUB>-C<SUB>4</SUB> et similaire.
EP05816549A 2004-12-17 2005-12-16 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles Withdrawn EP1828191A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102004060958 2004-12-17
DE102004062199 2004-12-23
PCT/EP2005/013577 WO2006066818A2 (fr) 2004-12-17 2005-12-16 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles

Publications (1)

Publication Number Publication Date
EP1828191A2 true EP1828191A2 (fr) 2007-09-05

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EP05816549A Withdrawn EP1828191A2 (fr) 2004-12-17 2005-12-16 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles

Country Status (8)

Country Link
US (1) US20080227796A1 (fr)
EP (1) EP1828191A2 (fr)
AR (1) AR052341A1 (fr)
BR (1) BRPI0517432A (fr)
PE (1) PE20060772A1 (fr)
TW (1) TW200637864A (fr)
UY (1) UY29260A1 (fr)
WO (1) WO2006066818A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
EP2066177B1 (fr) * 2007-01-19 2014-12-24 Basf Se Mélanges fongicides constitués d'anilides de l'acide 1-methylpyrazol-4-yl carboxylique et d'azolopyrimidinylamines
CN101588719B (zh) * 2007-01-30 2013-07-17 巴斯夫欧洲公司 基于唑并嘧啶基胺衍生物和杀虫剂的农药混合物
CN104395298A (zh) 2012-06-22 2015-03-04 住友化学株式会社 稠合杂环化合物

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GB0126914D0 (en) * 2001-11-08 2002-01-02 Syngenta Ltd Fungicides
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
DE10325133A1 (de) * 2003-06-04 2004-12-23 Bayer Cropscience Ag Triazolopyrimidine
DE10328481A1 (de) * 2003-06-25 2005-01-13 Bayer Ag Triazolopyrimidine
DE10360370A1 (de) * 2003-12-22 2005-07-14 Bayer Cropscience Ag Triazolopyrimidine

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Title
See references of WO2006066818A2 *

Also Published As

Publication number Publication date
PE20060772A1 (es) 2006-09-28
WO2006066818A3 (fr) 2006-11-02
US20080227796A1 (en) 2008-09-18
AR052341A1 (es) 2007-03-14
BRPI0517432A (pt) 2008-10-07
UY29260A1 (es) 2006-07-31
TW200637864A (en) 2006-11-01
WO2006066818A2 (fr) 2006-06-29

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