EP0640083A1 - Derives de pyrido 1,2-a]pyrimidinone substituee utiles comme fongicides - Google Patents

Derives de pyrido 1,2-a]pyrimidinone substituee utiles comme fongicides

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Publication number
EP0640083A1
EP0640083A1 EP93911028A EP93911028A EP0640083A1 EP 0640083 A1 EP0640083 A1 EP 0640083A1 EP 93911028 A EP93911028 A EP 93911028A EP 93911028 A EP93911028 A EP 93911028A EP 0640083 A1 EP0640083 A1 EP 0640083A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
haloalkyl
alkoxy
alkenyl
alkynyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP93911028A
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German (de)
English (en)
Inventor
Thomas Paul Selby
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0640083A1 publication Critical patent/EP0640083A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • This invention relates to certain substituted pyrido[1,2*-a]pyrimidinone compounds useful as fungicides, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides, in particular for the control of wheat powdery mildew both preventive and curative- Urban et al., Helv. Chi . Acta, 1970, 53, 905, disclose pyrido[1,2-a]pyrimidinones of Formula i and their use as analgesics and antiinflammatory agents.
  • This invention comprises compounds of Formula ⁇ including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and method of use of said compounds, salts, or compositions as fungicides,
  • Q is 0 or S; is O; S; S(O) ; S(0) 2 ; NH; or NR 9 ;
  • X is CR 3 or N;
  • Y is CR 4 or N;
  • CR 5 N;
  • N CR 6 ;
  • S O; or NR 7 ;
  • having the directionality of the CR 5 CR 6 r
  • R 1 is C- j ⁇ -C- L ⁇ alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18 alkenyl; C 2 -C 18 alkynyl; C-L-C-- ⁇ haloalkyl; C 2 -C 1 8 haloalkenyl; C 2 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alk lthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl;
  • C 4 -C 18 cycloalkylalkyl C 4 -C 18 alkenyloxyalkyl; C 4 -C 18 alkynyloxyalkyl; C 4 -C 18 cycloalkyloxy- alkyl; C 4 -C 18 alkenylthioalkyl; C 4 -C 18 alkynyl- thioalkyl; C 6 -C 18 cycloalkylthioalkyl; C 2 -C 18 haloalkoxyalkyl; C 3 -C 18 haloalkenyloxyalkyl;
  • R 3 and R 5 are each independently hydrogen; halogen; C ! -C 4 alkyl; C 1 -C 4 haloalkyl; C 1 -C alkoxy; or C 2 -C haloalkoxy; R 4 and R 6 are each independently hydrogen; halogen; c ⁇ -c 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl;
  • R 8 and R 9 are each independently O -C ⁇ alkyl;
  • R 10 and R 11 are each independently H or C x -C 4 alkyl;
  • R 12 is C- L -Cg alkyl;
  • R 8' and R 10 can be taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -,
  • R 5 and R 6 is equal to or less than 16; iii) the total number of nitrogen atoms incorporated into the bicyclic framework is less than or equal to four; iv) R 3 and R 4 are not both hydrogen; and v) X and Y are not both nitrogen.
  • Preferred for reasons of ease of synthesis or greater fungicidal activity are compounds of Formula I, denoted as Preferred 1, wherein: ' is 0; S; NH; or NR 9 ; X is CR 3 ; Y is CR 4 ;
  • R 1 is C-i-Cs alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 2 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; Ci-Ce alkoxy; C*-_-C 18 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkenylthio; or C 4 -C 8 alkenyloxyalkyl;
  • R 2 is C- j ⁇ -C ⁇ alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C 1 -C 8 haloalkyl; C -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; or phenyl optionally substituted with R 13 ; and R 4 and R 6 are each independently hydrogen; halogen; C- ⁇ Cs alkyl; C 3 -C 8 cycloalkyl; - j ⁇ -Cs haloalkyl; C ⁇ C**** alkoxy; C- j ⁇ -Cs haloalkoxy; C- j ⁇ -Ce alkylthio; C 1 -C 8 alkyls
  • R 1 is C -C Q alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C- j ⁇ -Cs haloalkyl; or C 2 -C 8 haloalkenyl;
  • R 2 is C ⁇ -C Q alkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C**_-C 8 haloalkyl; C 2 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ;
  • R 4 and R 6 are each independently hydrogen; halogen; C-L-C-3 alkyl; C 1 -C 8 haloalkyl; CJ ⁇ -C Q alkoxy; or C* j _-C 8 haloalkoxy.
  • compounds of Preferred 3 wherein said compounds are
  • alkyl used either alone or in compound words such as “alkylthio,” “haloalkyl,” or “alkylthioalkyl” denotes straight-chain or branched alkyl; e.g., methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl, hexyl, etc. isomers.
  • Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyl- oxyalkyl denotes the cycloalkyl groups linked through an oxygen atom to an alkyl chain. Examples include cyclopentyloxymethyl and cyclohexyloxybutyl.
  • the ter ⁇ i "cycloalkylthioalkyl” are the cycloalkyl groups linked through a sulfur atom to an alkyl chain; e.g., cyclo- propylthiopentyl .
  • Cycloalkylalkyl denotes a cycloalkyl ring attached to a branched or straight- chain alkyl; e.g. cyclopropylmethyl and cyclohexyl- butyl .
  • Alkenyl denotes straight chain or branched alkenes; e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl , pentenyl, hexenyl, etc. isomers. Alkenyl also denotes polyenes such as 1, 3-hexadiene and 2, 4, 6-heptatriene.
  • Alkenyl also denotes polyenes such as 1, 3-hexadiene and 2, 4, 6-heptatriene.
  • Alkenyl denotes straight chain or branched alkynes; e.g., ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl, hexynyl, etc. isomers.
  • Alkynyl can also denote moieties comprised of multiple triple bonds; e.g., 2, 7-octadiyne and 2, 5, 8-deca
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy, hexyloxy, etc. isomers.
  • alkylthioalkenyl and "alkylthioalkynyl.”
  • alkylthioalkenyl and "alkylthioalkynyl.”
  • alkenyloxyalkyl denotes groups in which the alkenyloxy moiety is attached to an alkyl group.
  • Alkynyloxy denotes straight or branched alkynyloxy moieties. Examples include HC ⁇ CCH 2 0,
  • Alkynylthioalkyl denotes alkynylthio moieties bonded to alkyl groups.
  • Alkylthio denotes methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio groups attached to an alkyl chain; e.g., CH 3 CH 2 SCH 2 CH(CH 3 ) and (CH 3 ) 2 CHSCH 2 .
  • Alkylsulfinyl denotes both enantiomers of an alkylsulfinyl group. For example, CH 3 S (0) , CH 3 CH 2 S (0) , CH 3 CH 2 CH 2 S (0) , (CH 3 ) 2 CHS(0) and the different but lsulfinyl, pentylsulfinyl and hexylsufinyl isomers.
  • Alkylsulfinylalkyl denotes alkylsulfinyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(0)CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(0)CH 2 .
  • alkylsulfonyl examples include CH 3 S(0) 2 , CH 3 CH 2 S(0) 2 , CH 3 CH 2 CH 2 S(0) 2r (CH 3 ) 2 CHS (O) 2 and the different butylsulfonyl, pentylsulfonyl and hexyl- sulfonyl isomers.
  • Alkylsulfonylalkyl denotes alkyl- sulfonyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(0) 2 CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS (0) 2 CH 2 .
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CF 2 . Examples of
  • Examples of “haloalkynyl” include HC ⁇ CCHCl, CF 3 C---C,
  • Haloalkoxyalkyl denotes haloalkoxy groups bonded to straight-chain or branched alkyl groups; e.g., CF 2 HCH 2 CH 2 0CH 2 CH 2 , CC1 3 CH 2 0CH(CH 3 ) and CF 3 OCH 2 .
  • Trialkylsilyl designates a group with three alkyl groups bonded to silicon; e.g., (CH 3 ) 3 Si and t-Bu(CH 3 ) 2 Si.
  • "Trialkylsilylalkyl” denotes trialkylsilyl groups bonded to another straight-chain or branched alkyl group. Examples include (CH 3 ) 3 SiCH 2 and t-Bu(CH 3 ) 2 SiCH 2 CH(CH 3 )CH 2 .
  • the total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 20.
  • C 1 -C 3 alkyl- sulfonyl designates methylsulfonyl through propyl- sulfonyl
  • C 2 alkoxyalkoxy designates CH 3 OCH 2 0
  • C 3 alkoxyalkoxy designates, for example, CH 3 OCH CH 2 0 or
  • CH 3 CH 2 OCH 0; and C 4 alkoxyalkoxy designates the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 0, and CH 3 CH 2 OCH 2 CH 2 0.
  • alkoxyalkyl include CH 3 0CH 2 , CH 3 0CH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • Compounds of Formula I can be prepared using one or more of the reactions and techniques described in Schemes 1-4 hereinafter, or by following the procedures given in Examples 1-6.
  • G 0, S,NH, NR 3
  • Bromination of compounds of Formula Ig with bromine or N-bromosuccinimide (NBS) yields brominated adducts of Formula VII which can be coupled with stannanes of Formula R 14 Sn(CH 3 ) 3 in the presence of a palladium catalyst such as tetrakis (triphenylphosphine)- palladium(O) or bis (triphenylphosphine)palladium(II) chloride to afford products of Formula If.
  • a palladium catalyst such as tetrakis (triphenylphosphine)- palladium(O) or bis (triphenylphosphine)palladium(II) chloride to afford products of Formula If.
  • Bromoheterocycles of Formula VII can also be coupled with terminal alkynes using palladium catalysis in the presence of base (such as triethylamine) and cuprous iodide.
  • Salts of compounds of Formula I can be formed by treating the free base of Formula I with strong acids such as hydrochloric or sulfuric acid.
  • N-oxides of compounds of Formula I can be made by oxidizing compounds of Formula I with a strong oxidizing agent such as jneta-chloroperoxybenzoic acid.
  • reaction mixture was partitioned between 150 mL of water and 200 mL of ethyl acetate and the organic layer separated followed by washing with water (3 times) and brine. After drying over magnesium sulfate, the solvent was evaporated in vacuo to give a yellow solid residue which was flash chromatographed on silica gel (10:1-5:1-3:1 hexane/ethyl acetate) to afford 5.2 g of the title compound as a white solid, m.p.
  • t - is tertiary OMe - is ethoxy s - is secondary SEt - is ethylthio n - is normal CN - is cyano i - is iso TMS - is trimethylsilyl Me - is methyl S(0)Me - is methylsulfinyl Et - is ethyl S(0) Me - is methylsulfonyl Ph - is phenyl
  • compositions of this invention comprise an effective amount of a compound of Formula I as defined above and at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent
  • useful formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • Weight Percent weight percent
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
  • Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S. 3,060,084.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4,
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in DE 3,246,493.
  • Compound 3 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Compound 3 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
  • Example C Extruded Pellet Compound 3 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Compound 3 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.
  • the compounds and compositions of this invention are usef l as plant disease control agents.
  • the present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling an effective amount of a compound of Formula I, an N-oxide thereof, an agriculturally suitable salt thereof, or a fungicidal composition containing said compound, N-oxide, or salt.
  • the compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops.
  • pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi- component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathio ⁇ -methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, methamidophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxych
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the plant or portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
  • the compounds can also be applied to the seed to protect the seed and seedling.
  • Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
  • Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
  • The'following Tests demonstrate the control efficacy of compounds of this invention on specific pathogens. The pathogen control protection a forded by the compounds is not limited, however, to these species. See Index Tables A and B for compound descriptions.
  • Test compounds were first dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem® 014
  • test suspensions were then used in the following tests.
  • test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore dust of Erysiphe graminis f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at
  • test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore suspension of
  • Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
  • TEST C The test suspension was sprayed to the point of run-off on rice seedlings. The following day the seedlings were inoculated with a spore suspension of Pyricularia oryzae (the causal agent of rice blast) and incubated in a saturated atmosphere at 27°C for 24 h, and then moved to a growth chamber at 30°C for 5 days, after which disease ratings were made. TEST D The test suspension was sprayed to the point of run-off on tomato seedlings.
  • test suspension was sprayed to the point of run-off on grape seedlings.
  • seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made.
  • Plasmopara viticola the causal agent of grape downy mildew
  • TEST F The test suspension was sprayed to the point of run-off on cucumber seedlings. The following day the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Botrytis cinerea the causal agent of gray mold on many crops
  • Results for Tests A-F are given in Table C.
  • a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls) .
  • NT Not Tested.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composés de pyrido[1,2-a]pyrimidinone substituée répondant à la formule (I) dans laquelle Q représente O ou S; W représente O, S, S(O), S(O)2, NH, ou NR9; X représente CR3 ou N; Y représente CR4 ou N; Z représente CR?5=CR6, CR5¿=N, N=CR6, S, O, ou NR?7; et R1, R2, R3, R4, R5, R6 et R7¿ représentent des groupes divers. L'invention concerne également des compositions agricoles contenant un ou plusieurs de ces composés, utiles comme fongicides pour lutter contre des maladies végétales.
EP93911028A 1992-05-13 1993-05-10 Derives de pyrido 1,2-a]pyrimidinone substituee utiles comme fongicides Withdrawn EP0640083A1 (fr)

Applications Claiming Priority (3)

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US88221592A 1992-05-13 1992-05-13
US882215 1992-05-13
PCT/US1993/004188 WO1993023398A1 (fr) 1992-05-13 1993-05-10 Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides

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EP0640083A1 true EP0640083A1 (fr) 1995-03-01

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BR112019025740A2 (pt) 2017-06-05 2020-06-23 Ptc Therapeutics, Inc. Compostos para tratar a doença de huntington
CA3065547A1 (fr) 2017-06-14 2018-12-20 Ptc Therapeutics, Inc. Procedes de modification de l'epissage de l'arn
BR112019027719A2 (pt) 2017-06-28 2020-07-28 Ptc Therapeutics, Inc. métodos para tratar a doença de huntington
US11382918B2 (en) 2017-06-28 2022-07-12 Ptc Therapeutics, Inc. Methods for treating Huntington's Disease
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EP3814360A1 (fr) 2018-06-27 2021-05-05 PTC Therapeutics, Inc. Composés hétéroaryles pour le traitement de la maladie de huntington
EA202092896A1 (ru) 2018-06-27 2021-04-13 ПиТиСи ТЕРАПЬЮТИКС, ИНК. Гетероциклические и гетероарильные соединения для лечения болезни гентингтона
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AU4231293A (en) 1993-12-13

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