WO2003039259A1 - Fongicides - Google Patents

Fongicides Download PDF

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Publication number
WO2003039259A1
WO2003039259A1 PCT/GB2002/004734 GB0204734W WO03039259A1 WO 2003039259 A1 WO2003039259 A1 WO 2003039259A1 GB 0204734 W GB0204734 W GB 0204734W WO 03039259 A1 WO03039259 A1 WO 03039259A1
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Prior art keywords
alkyl
heteroaryl
alkylamino
aryl
amino
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PCT/GB2002/004734
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English (en)
Inventor
Paul Anthony Worthington
Ingrid Aurelie Valancogne
Delphine Raymonde Suzanne Fawke
Markus Dobler
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Syngenta Limited
Syngenta Participations Ag
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Publication of WO2003039259A1 publication Critical patent/WO2003039259A1/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
    • 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

Definitions

  • This invention relates to the use as plant fungicides of certain substituted 5-1,2,4-tri- azolo[l,5-a]pyrimidine compounds. It also relates to plant fungicidal compositions containing these compounds and to many of the compounds themselves. There are many substituted s-l,2,4-triazolo[l,5-a]pyrimidines known from the patent literature as being useful for controlling phytopathogenic fungi.
  • the present invention is concerned with the provision of alternative substituted s- l,2,4-triazolo[l,5-a]pyrimidines for use as plant fungicides.
  • R is H, halo, C 1-8 alkyl or cyano;
  • X and Y are independently halo, C 1-8 alkoxy, C ⁇ -8 alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkoxy, alkoxy, aryl(C 1- )alkylthio, heteroaryl(C 1- )alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, di(C 2-8 )alkenylamino, di(C 2-8 )alkynylamino, C 2-8 alkenyl-
  • (C 2-8 )alkynylamino C 2-8 alkynyl(C 1-8 )alkylamino or C 2-8 alkenyl(C 1-8 )alkylamino arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, aryl(C 1- )alkylamino, aryl(C 1-4 )alkyl(C 1-8 alkyl)amino, heteroaryl(C 1- )alkylamino, heteroaryl(C 1- )alkyl (C 1-8 alkyl)amino, morpholino or piperidino, or Y is hydroxy, provided that when X is C 1-8 alkoxy, aryloxy, morpholino or piperidino, R and Y are not both halo; any of the foregoing alkyl, alkenyl, alkynyl, aryl, heteroaryl,
  • alkyl (C 1-8 alkyl)amino or Y is hydroxy, morpholino or piperidino, provided that when X is other than halo, R and Y are not both halo; any of the foregoing alkyl, alkenyl, alkynyl, aryl, heteroaryl, morpholino or piperidino groups or moieties being optionally substituted.
  • R is H, halo, C 1-8 alkyl or cyano
  • X is halo, C 1-8 alkylthio, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkylthio, heteroaryl(C ⁇ -4 )alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, aryl(C 1-4 )alkylamino, aryl(C ⁇ .
  • Y is halo, hydroxy, Cj -8 alkoxy, C 1-8 alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1- )alkoxy, heteroaryl(C 1-4 )alkoxy, aryl(C 1- )alkylthio, heteroaryl(C 1-4 )alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(Ci- 8 )alkylamino, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, aryl(C 1- )alkyl
  • the compounds of the invention may contain one or more asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. However, these mixtures may be separated into individual isomers or isomer pairs, and this invention embraces such isomers and mixtures thereof in all proportions. It is to be expected that for any given compound, one isomer may be more fungicidally active than another. Except where otherwise stated, alkyl groups and alkyl moieties of alkoxy, alkylamino, etc., suitably contain from 1 to 6, typically from 1 to 4, carbon atoms in the form of straight or branched chains.
  • Examples are methyl, ethyl, n- and zs ⁇ -propyl, n-, sec-, iso- and tert- butyl, n-pentyl and n-hexyl.
  • suitable optional substituents of alkyl groups and moieties include halo, hydroxy, C 1- alkoxy and C M alkoxy(C 1-4 )alkoxy. Where the optional substituent is halo, the haloalkyl group or moiety is typically trichloromethyl or trifluoromethyl.
  • Alkenyl and alkynyl moieties also suitably contain from 1 to 6, typically from 1 to 4, carbon atoms in the form of straight or branched chains. Examples are allyl, 2-methylallyland propargyl.
  • Optional substituents include halo, typically fluoro, for example, 2,2,2-trifluoro-l- methylethyl.
  • Halo includes fluoro, chloro, bromo and iodo. Most commonly it is fluoro, chloro or bromo.
  • Aryl is usually phenyl but also includes naphthyl, anthryl and phenanthryl.
  • Heteroaryl is typically a 5- or 6-membered aromatic ring containing one or more O, N or S heteroatoms, which may be fused to one or more other aromatic or heteroaromatic rings, such as a benzene ring.
  • Examples are thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl, oxadiazolyl, pyrazolyl, imidazolyl, triazolyl, isothiazolyl, tetrazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzofuryl, benzothienyl, dibenzofuryl, benzothiazolyl, benzoxazolyl, benzimidazolyl, indolyl, quinolinyl and quinoxalinyl groups and, where appropriate, N-oxides thereof.
  • any of the aryl or heteroaryl values are optionally substituted by one or more, typically 1, 2 or 3, substituents of the kind that are customarily present in pesticidal compounds.
  • Substituents which may be present include one or more of the following: halo, hydroxy, mercapto, C 1-8 alkyl (especially methyl and ethyl), C 2-6 alkenyl (especially allyl), C 2- 6 alkynyl (especially propargyl), C 1-6 alkoxy (especially methoxy), C 2-6 alkenyloxy (especially allyloxy), C 3-6 alkynyloxy (especially propargyloxy), halo(C 1-8 )alkyl (especially trifluoromethyl), halo(C 1-6 )alkoxy (especially trifluoromethoxy), C 1-6 alkylthio (especially methylthio), hydroxy(C 1-6 )alkyl, C 1-4 alkoxy(C 1- )alkyl, C ⁇ -4 al
  • Substituents which may be present in the aryl or heteroaryl rings of any of the foregoing substituents include one or more of the following: halo, hydroxy, mercapto, C 1- alkyl, C 2-4 , alkenyl, C 2-4 alkynyl, C 1-4 alkoxy, C 2- alkenyloxy, C 3-4 alkynyloxy, halo- (C ⁇ -4 )alkyl, halo(C 1-4 )alkoxy, C 1-4 alkylthio, halo(C 1-4 )alkylthi ⁇ , hydroxy(C ⁇ - )alkyl, C 1- alkoxy(C ⁇ -4 )alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl(C 1-4 )alkyl, alkanoyloxy, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyana
  • X or Y is aryloxy, arylthio, heteroaryloxy, heteroarylthio, alkoxy, heteroaryl(C 1-4 )alkoxy, aryl(C 1-4 )alkylthio, heteroaryl(C 1-4 )alkylthio, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, aryl(C 1- )alkylamino, aryl(C 1-4 )alkyl(C 1-8 alkyl)amino, heteroaryl(C 1-4 )alkylamino or heteroaryl(C 1-4 )alkyl(C 1-8 alkyl)amino the other is suitably halo, C 1-8 alkoxy, C 1-8 alkylthio, C 1-8 alkylamino, di(C 1-8 )- alkylamino, or, in the case of Y, hydroxy
  • the invention provides the use as a plant fungicide of a compound of the general formula (I) wherein R is H, halo, C ⁇ -8 alkyl or cyano; X is halo, C 1-8 alkoxy, C ⁇ -8 alkylthio, C 1-8 alkylamino or di(C ⁇ -8 )alkylamino and Y is aryloxy, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkoxy, heteroaryl(C 1-4 )- alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C ⁇ -8 )alkylamino, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, ary C] ⁇ )- alkylamino, aryl(C 1-4 cyan
  • R is typically halo or C 1-4 alkyl and X is typically halo (especially bromo), C 1-4 alkoxy or C ⁇ -4 alkylthio.
  • Aryl is usually phenyl and heteroaryl is, for example, pyridyl, pyrimidinyl, thienyl or imidazolyl.
  • Y is C 1-4 alkylamino, halo(C 1-4 )alkylamino, C 2-4 alkenylamino, halo(C 2-4 )- alkenylamino, C 2- alkynylamino, halo(C 2-4 )alkynylamino, benzyloxy, benzylamino, heteroaryl(C 1-3 )alkylamino where the heteroaryl moiety is, for example, pyridyl, thienyl or imidazolyl and the phenyl moieties of the benzyl groups and the heteroaryl moieties are optionally substituted with halo, C 1- alkyl, C 1-4 alkoxy, halo(C 1- )alkyl, halo(C ⁇ -4 )alkoxy, cyano or nitro.
  • the invention provides the use as a plant fungicide of a compound of the general formula (I) wherein R is H, halo, C ⁇ -8 alkyl or cyano X is aryloxy, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkoxy, heteroaryl(C 1-4 )alkoxy, aryl(C ⁇ .
  • R is typically halo or C 1-4 alkyl and Y is typically halo (especially chloro), hydroxy, C 1-4 alkylamino or halo(C 1- )alkylamino.
  • Aryl is usually phenyl and heteroaryl is, for example, pyridyl, pyrimidinyl, thienyl or imidazolyl.
  • X is phenylthio or heteroarylthio where the heteroaryl moiety is, for example, pyridyl, thienyl or imidazolyl and the phenyl and heteroaryl moieties are optionally substituted with halo, C 1-4 alkyl, C 1- alkoxy, halo . )alkyl, halo(C 1- )alkoxy, cyano or nitro.
  • the invention provides the use as a plant fungicide of a compound of the general formula (I) wherein R is halo (e.g. chloro); X is phenoxy, phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy), heteroarylthio (e.g.
  • Y is C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, di(C 2-8 )alkenylamino, di(C 2- 8 )alkynylamino, C 2-8 alkenyl(C 2-8 )alkynylamino C 2-8 alkynyl(C 1-8 )alkylamino or C 2-8 alkenyl(C 1-8 )alkylamino; any of the foregoing alkyl, alkenyl, alkynyl, phenyl, heteroaryl, morpholino or piperidino groups or moieties being optionally substituted.
  • Halo is a typical substituent of alkyl, alkenyl and alkynyl and halo (e.g. chloro and fluoro), C ⁇ - 4 alkyl, halo(C 1- )alkyl (e.g. trifluoromethyl), C 1-4 alkoxy, halo(C 1-4 )alkoxy (e.g. trifluoromethoxy) and nitro are typical substituents of phenyl and heteroaryl groups.
  • Exemplary values of Y are 2,2,2-trifluoro-l-methylethylamino and N-ethyl-2- methylallylamino.
  • the invention provides the use as a plant fungicide of a compound of the general formula (I) wherein R is halo (e.g. chloro); X is phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy) or heteroarylthio (e.g. pyridinylthio and pyrimidinylthio); and Y is halo (e.g. chloro); any of the foregoing phenyl or heteroaryl moieties being optionally substituted, for example, with the substituents described in the previous paragraph.
  • R is halo (e.g. chloro)
  • X is phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy) or heteroarylthio (e.g. pyridinylthio and pyrimidinylthio)
  • Y is halo (e.g. chloro); any of the
  • the invention also includes those compounds of general formula (I) that are novel.
  • the invention provides a compound of general formula (I) wherein R is H, halo, C 1-8 alkyl or cyano; X and Y are independently halo, C ⁇ -8 alkoxy, C 1-8 alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkoxy, heteroaryl(C ⁇ -4 )alkoxy, aryl(C 1- )alkylthio, heteroaryl(C 1-4 )alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, hetero- aryl(C 1-8 alkyl)amino, aryl(C 1-4 1-4
  • the invention includes a compound of the general formula (I) wherein R is H, halo, C 1-8 alkyl or cyano; X is halo, C 1-8 alkylthio, arylthio, heteroaryloxy, heteroarylthio, aryl(C 1-4 )alkylthio, heteroaryl(C 1- )alkylthio, C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, arylamino, aryl(C 1-8 alkyl)amino, heteroarylamino, heteroaryl(C 1-8 alkyl)amino, aryl(C 1- )alkylamino, aryl(C 1-4 )alkyl(C 1-8 alkyl)amino, heteroaryl(C 1- )alkylamino or heteroaryl(C 1-4 )alkyl (C 1-8 alkyl (C
  • the invention also includes a compound of the general formula (I) wherein R is halo (e.g. chloro); X is phenoxy, phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy), heteroarylthio (e.g.
  • Y is C 1-8 alkylamino, C 2-8 alkenylamino, C 2-8 alkynylamino, di(C 1-8 )alkylamino, di(C 2- 8 )alkenylamino, di(C 2-8 )alkynylamino, C 2-8 alkenyl(C 2-8 )alkynylamino C 2-8 alkyny C], s)alkylamino or C 2-8 alkenyl(C 1-8 )alkylamino; any of the foregoing alkyl, alkenyl, alkynyl, phenyl, heteroaryl, morpholino or piperidino groups or moieties being optionally substituted.
  • Halo is a typical substituent of alkyl, alkenyl and alkynyl and halo (e.g. chloro and fluoro), C 1- alkyl, halo(C 1-4 )alkyl (e.g. trifluoromethyl), C ⁇ _ 4 alkoxy, halo d. 4 )alkoxy (e.g. trifluoromethoxy) and nitro are typical substituents of phenyl and heteroaryl groups.
  • Exemplary values of Y are 2,2,2-trifluoro-l-methylethylamino and N-ethyl-2- methylallylamino.
  • the invention further includes a compound of the general formula (I) wherein R is halo (e.g. chloro); X is phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy) or heteroarylthio (e.g. pyridinylthio and pyrimidinylthio; and Y is halo (e.g. chloro); any of the foregoing phenyl or heteroaryl moieties being optionally substituted, for example, with the substituents described in the previous paragraph.
  • R is halo (e.g. chloro)
  • X is phenylthio, heteroaryloxy (e.g. pyridyloxy and pyrimidinyloxy) or heteroarylthio (e.g. pyridinylthio and pyrimidinylthio
  • Y is halo (e.g. chloro); any of the foregoing phenyl or heteroary
  • the compounds of formula (I) may be prepared as outlined in Routes 1 to 6 below, in which R has the meaning given above and L is a leaving group such as halo.
  • Y is shown as OR l5 NHRi, NHR 2 , NR 2 R 3 or N ⁇ and X is shown as OR x , SRi, SR 2 or NRtR 2 , the values of Ri, R 2 , R 3 and R being derived from the meanings of X and Y given above.
  • H ⁇ nig's base is N,N-di s ⁇ propylethylamine.
  • compounds where Y is an amino-linked substituent (II), in which R is methyl may be prepared by reacting a compound of general formula (HI) with the appropriate primary amine R ⁇ H 2 or secondary amine RtR 2 NH conveniently in a solvent such as dimethyl sulphoxide at about 0°C in the presence of H ⁇ nig's base.
  • the compound of general formula (ID) may be prepared by treating a compound of general formula (IV) with phosphoryl chloride under reflux conditions.
  • the compound of formula (IN) may be prepared by treating a compound of general formula (N) with liquid bromine at room temperature in, for example, glacial acetic acid.
  • the compound of general formula (N) where R is methyl is commercially available.
  • (NH) may be prepared, as shown in Route 3, by chlorinating a compound of general formula
  • the compound of general formula (VET) may be prepared by reacting a compound of general formula (IV) with a thiol of formula R[SH.
  • X is a S-linked substituent and Y is an amino-linked substituent
  • (IX) may also be prepared, as shown in Route 4, by reacting a compound of general formula
  • X is a N-bridged substituent and Y is an amino-linked substituent (XHT) may be prepared, as shown in Route 6, by chlorinating a compound of general formula (XL! with, for example, phosphoryl chloride followed by treatment with an amine R 3 R ⁇ H in DMF.
  • the compound of general formula (XII) may be prepared by reacting a compound of general formula (IV) with an amine of formula R 3 R 4 NH in DMF.
  • the compounds of formula (I) are active fungicides and may be used to control one or more of the following pathogens: Pyricularia oryzae (Magnaporthe grisea) on rice and wheat and other Pyricularia spp. on other hosts; Puccinia triticina (or recondita), Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants); Erysiphe cichoracearum on cucurbits (for example melon); Blumeria (or Erysiphe) graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca macularis on hops, Sphaero
  • Botrytis cinerea grey mould
  • Botrytis cinerea grey mould
  • Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts
  • Venturia spp. including Venturia inaequalis (scab)) on apples, pears, stone fruit, tree nuts and other hosts
  • Cladosporium spp. on a range of hosts including cereals (for example wheat) and tomatoes
  • a compound of formula (I) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of formula (I) may be volatile enough to be active in the vapour phase against one or more fungi on the plant.
  • the invention therefore provides a method of combating or controlling phytopatho- genic fungi which comprises applying a fungicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a plant, to a seed of a plant, to the locus of the plant or seed or to soil or any other plant growth medium, e.g. nutrient solution.
  • plant as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes protectant, curative, systemic, eradicant and antisporulant treatments.
  • the compounds of formula (I) are preferably used for agricultural, horticultural and turf grass purposes in the form of a composition.
  • a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • SFAs are chemicals that are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • compositions both solid and liquid formulations
  • the composition is generally used for the control of fungi such that a compound of formula (I) is applied at a rate of from 0. lg tolOkg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
  • a compound of formula (I) When used in a seed dressing, a compound of formula (I) is used at a rate of O.OOOlg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
  • the present invention provides a fungicidal composition
  • a fungicidal composition comprising a fungicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor.
  • the invention provides a method of combating and controlling fungi at a locus which comprises treating the fungi or the locus of the fungi with a fungicidally effective amount of a composition comprising a compound of formula (I).
  • compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
  • the formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
  • Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulphate
  • water-soluble organic solids such as a polysaccharide
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, mineral carbonates, sulphates or phosphates
  • Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
  • One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
  • DC Dispersible Concentrates
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclo- hexanone), alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N- alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C 8 -do fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents that have a low solubility in water.
  • Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs.
  • An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
  • SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane).
  • a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
  • a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment.
  • a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
  • a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
  • DS powder for dry seed treatment
  • SS water soluble powder
  • WS water dispersible powder for slurry treatment
  • CS capsule suspension
  • the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
  • Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
  • Wetting agents, dispersing agents and emulsifying agents may be SFAs of the cationic, anionic, amphoteric or non-ionic type.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di- /s ⁇ propyl- and tri-/s ⁇ propyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
  • hydrophilic colloids such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose
  • swelling clays such as bentonite or attapulgite
  • a compound of formula (I) may be applied by any of the known means of applying fungicidal compounds. For example, it may be applied, formulated or unformulated, to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
  • These concentrates which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • a compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers).
  • fertilisers for example nitrogen-, potassium- or phosphorus-containing fertilisers.
  • Suitable formulation types include granules of fertiliser.
  • the mixtures suitably contain up to 25% by weight of the compound of formula (I).
  • the invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the resulting composition may have a broader spectrum of activity or a greater level of intrinsic activity than the compound of formula (I) alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of the compound of formula (I).
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient will depend upon the intended utility of the composition.
  • fungicidal compounds which may be included in the composition of the invention are AC 382042 (N-(l -cyano- l,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) pro- pionamide), acibenzolar-S-methyl, alanycarb, aldimorph, anilazine, azaconazole, azafenidin, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA 41396, CGA 41397, chinomethionate, chlorbenzthiazone, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper
  • the compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. these circumstances other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • test compounds were individually formulated as a solution either in acetone or acetone/ethanol (1 : 1 by volume) which was diluted in reverse osmosis water to a concentration of 75 or lOOppm (that is, 0.75 or lmg of compound in a final volume of 10ml) immediately before use.
  • TWEEN 20 0.05% by volume
  • Each treatment was applied to two or more replicate plants for Plasmopara viticola, Phytophthora infestans lycopersici, Botrytis cinerea, Uncinula necator and Venturia inaequalis and in all tests where the cellulose growing medium was employed.
  • Blumeria graminis f.sp. tritici, Stagonospora nodorum, Puccinia triticina, Rhizoctonia solani and Pyricularia oryzae two replicate pots each containing 6 tolO plants were used for each treatment.
  • the plants were inoculated with a calibrated fungal spore suspension one or two days before (Erad) or 6hours, one day or two days after (Prot) chemical application.
  • the plants were incubated under high humidity conditions and then put into an appropriate environment to allow infection to proceed, until the disease was ready for assessment.
  • the Blumeria graminis f.sp. tritici plants were inoculated using a 'shake' inoculation technique.
  • the Uncinula necator plants were inoculated using a 'blowing' inoculation technique.
  • the time period between chemical application and assessment varied from five to fourteen days according to the disease and environment. However, each individual disease was assessed after the same time period for all compounds.
  • Pyricularia oryzae assessments were carried out collectively on the plants in each replicate pot or cellulose medium. For Rhizoctonia solani, the number of infected plants in each of two replicate pots was assessed.
  • the disease level present that is, the percentage leaf area covered by act vely sporulating disease
  • percentage of infected plants per pot was assessed visually.
  • the assessed values for all its replicates were meaned to provide mean disease values.
  • Untreated control plants were assessed in the same manner.
  • This Example illustrates the fungicidal properties of compounds of formula (I), where the compounds were tested against a variety of foliar fungal diseases of plants in a leaf disk assay, with methods described below. Test compounds were dissolved in DMSO, and diluted into water to 200 ppm.
  • Erysiphe graminis f.sp. hordei barley leaf segments were placed on agar in a 24- well plate and sprayed with a solution of the test compound. After allowing to dry completely, for between 12 and 24 hours, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed four days after inoculation as preventive fungicidal activity.
  • Erysiphe graminis f.sp. tritici wheat leaf segments were placed on agar in a 24-well plate and sprayed with a solution of the test compound.
  • the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed four days after inoculation as preventive fungicidal activity.
  • Pyricularia oryzae rice blast: rice leaf segments were placed on agar in a 24-well plate and sprayed with a solution of the test compound. After allowing to dry completely, for between 12 and 24 hours, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed four days after inoculation as preventive fungicidal activity.
  • Botrytis cinerea grey mould: bean leaf disks were placed on agar in a 24-well plate and sprayed with a solution of the test compound. After allowing to dry completely, for between 12 and 24 hours, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed four days after inoculation as preventive fungicidal activity.
  • Phytophthora infestans (late blight of potato on tomato): tomato leaf disks were placed on water agar in a 24-well plate and sprayed with a solution of the test compound. After allowing to dry completely, for between 12 and 24 hours, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed four days after inoculation as preventive fungicidal activity.
  • Plasmopara viticola downy mildew of grapevine: grapevine leaf disks were placed on agar in a 24-well plate and sprayed a solution of the test compound. After allowing to dry completely, for between 12 and 24 hours, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound was assessed seven days after inoculation as preventive fungicidal activity.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne l'utilisation comme fongicide pour plante d'un composé représenté par la formule (I) dans laquelle R représente H, halo, C1-8 alkyle ou cyano; X and Y are indépendamment halo, C1-8 alcoxy, C1-8 alkylthio, aryloxy, arylthio, hétéroaryloxy, hétéroarylthio, aryl(C1-4)-alcoxy, hétéroaryl(C1-4)alcoxy, aryl(C1-4)alkylthio, hétéroaryl(C1-4)alkylthio, C1-8 alkylamino, C2-8 alcénylamino, C2-8 alkynylamino, di(C1-8)alkylamino, di(C2-8)-alcénylamino, di(C2-8)alkynylamino, (C2-8)alkynylamino C2-8 alkyl-(C1-8)alkylamino ou C2-8 alcényl(C1-8)alkylamino arylamino, aryl(C1-8 alkyl)amino, hétéroarylamino, hétéroaryl(C1-8 alkyl) amino, aryl(C1-4)alkylamino, aryl(C1-4)alkyle-(C1-8 alkyl)amino, hétéroaryl(C1-4)alkylamino, hétéroaryl(C1-4)alkyle (C1-8 alkyl)amino, morpholino ou piperidino, ou Y représente hydroxy à la condition que, lorsque X représente C1-8 alcoxy, aryloxy, morpholino ou piperidino, R et Y ne représentent pas tous deux halo; n'importe lequel des groupes ou des fractions précédents, à savoir alkyle, alcényle, alkynyle, aryle, hétéroaryle, morpholino ou piperidino étant substitués. L'invention concerne également des compositions fongicides pour plante contenant ces composés et bon nombre des composés eux-mêmes.
PCT/GB2002/004734 2001-11-08 2002-10-21 Fongicides WO2003039259A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0126914A GB0126914D0 (en) 2001-11-08 2001-11-08 Fungicides
GB0126914.1 2001-11-08

Publications (1)

Publication Number Publication Date
WO2003039259A1 true WO2003039259A1 (fr) 2003-05-15

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AR (1) AR037266A1 (fr)
GB (1) GB0126914D0 (fr)
GT (1) GT200200227A (fr)
TW (1) TW200302051A (fr)
WO (1) WO2003039259A1 (fr)

Cited By (10)

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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
WO2004113341A2 (fr) * 2003-06-24 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2005025315A1 (fr) * 2003-09-12 2005-03-24 Basf Aktiengesellschaft 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines permettant de combattre des parasites des animaux
WO2005067716A1 (fr) * 2004-01-20 2005-07-28 Basf Aktiengesellschaft Melanges fongicides
WO2005089555A1 (fr) * 2004-03-17 2005-09-29 Basf Aktiengesellschaft Melanges fongicides
WO2006066818A2 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006066799A1 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre les champignons pathogenes
JP2007506665A (ja) * 2003-06-27 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト ピラゾロピリミジン
WO2009080546A1 (fr) 2007-12-21 2009-07-02 Basf Se Utilisation de composés 6-halogéno-[1,2,4]-triazolo-[1,5-a]-pyrimidine dans la lutte contre les nuisibles chez l'animal

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* 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
JPWO2004011467A1 (ja) * 2002-07-29 2005-12-15 北興化学工業株式会社 トリアゾロピリミジン誘導体および農園芸用殺菌剤
WO2004113341A2 (fr) * 2003-06-24 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
JP2007506657A (ja) * 2003-06-24 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺真菌性トリアゾロピリミジン類
WO2004113341A3 (fr) * 2003-06-24 2005-05-12 Bayer Cropscience Ag Triazolopyrimidines
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
JP2007506659A (ja) * 2003-06-25 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト トリアゾロピリミジン類
JP2007506665A (ja) * 2003-06-27 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト ピラゾロピリミジン
KR101141562B1 (ko) * 2003-09-12 2012-05-22 메리얼 리미티드 동물 해충의 방제를 위한 6-할로게노-〔1,2,4〕트리아졸로〔1,5-ａ〕피리미딘
EA010091B1 (ru) * 2003-09-12 2008-06-30 Басф Акциенгезельшафт 6-ГАЛОГЕНО[1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ ДЛЯ БОРЬБЫ С ВРЕДИТЕЛЯМИ
AU2004271715B2 (en) * 2003-09-12 2010-08-26 Basf Aktiengesellschaft 6-halogeno-(1,2,4)triazolo(1,5-a)pyrimidines for combating animal pests
JP2007505077A (ja) * 2003-09-12 2007-03-08 ビーエーエスエフ　アクチェンゲゼルシャフト 動物害虫を駆除するために用いる６−ハロゲノ−［１，２，４］トリアゾロ［１，５−ａ］ピリミジン類
US8664235B2 (en) 2003-09-12 2014-03-04 Merial Limited 6-Halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests
WO2005025315A1 (fr) * 2003-09-12 2005-03-24 Basf Aktiengesellschaft 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines permettant de combattre des parasites des animaux
AP1762A (en) * 2004-01-20 2007-07-31 Basf Ag Fungicidal mixtures
WO2005067716A1 (fr) * 2004-01-20 2005-07-28 Basf Aktiengesellschaft Melanges fongicides
WO2005089555A1 (fr) * 2004-03-17 2005-09-29 Basf Aktiengesellschaft Melanges fongicides
WO2006066818A3 (fr) * 2004-12-17 2006-11-02 Basf Ag 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006066799A1 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre les champignons pathogenes
WO2006066818A2 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2009080546A1 (fr) 2007-12-21 2009-07-02 Basf Se Utilisation de composés 6-halogéno-[1,2,4]-triazolo-[1,5-a]-pyrimidine dans la lutte contre les nuisibles chez l'animal
AU2008340434B2 (en) * 2007-12-21 2014-02-06 Boehringer Ingelheim Animal Health USA Inc. The use of 6-halogeno-[1,2,4]-triazolo-[1,5-a]-pyrimidine compounds for combating pests in and on animals

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