WO1993023398A1 - Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides - Google Patents

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

Info

Publication number
WO1993023398A1
WO1993023398A1 PCT/US1993/004188 US9304188W WO9323398A1 WO 1993023398 A1 WO1993023398 A1 WO 1993023398A1 US 9304188 W US9304188 W US 9304188W WO 9323398 A1 WO9323398 A1 WO 9323398A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
propyl
haloalkyl
alkoxy
alkenyl
Prior art date
Application number
PCT/US1993/004188
Other languages
English (en)
Inventor
Thomas Paul Selby
Original Assignee
E.I. Du Pont De Nemours And Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to EP93911028A priority Critical patent/EP0640083A1/fr
Publication of WO1993023398A1 publication Critical patent/WO1993023398A1/fr

Links

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 curativeUrban et al., Helv. Chim . Acta, 1970, 53, 905, disclose pyrido [1,2-a]pyrimidinones of Formula i and their use as analgesics and antiinflammatory agents.
  • W is O; S or NH;
  • This invention comprises compounds of Formula I 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 O or S
  • W is O; S; S(O); S(O) 2 ; NH; or NR 9 ;
  • X is CR 3 or N
  • Y is CR 4 or N
  • R 1 is C 1 -C 18 alkyl; C 3 -C 7 cycloalkyl; C 2 -C 18
  • alkenyl C 2 -C 18 alkynyl; C 1 -C 18 haloalkyl; C 2 -C 18 haloalkenyl; C 2 -C 18 haloalkynyl; C 2 -C 18 alkoxyalkyl; C 2 -C 18 alkylthioalkyl; C 2 -C 18 alkylsulfinylalkyl; C 2 -C 18 alkylsulfonylalkyl;
  • C 4 -C 18 haloalkynyloxyalkyl C 4 -C 18 alkoxyalkenyl; C 4 -C 18 alkoxyalkynyl; C 4 -C 18 alkylthio alkenyl; C 4 -C 18 alkylthioalkynyl; C 4 -C 18 trialkylsilylalkyl; C 1 -C 18 alkyl substituted with NR 8 R 10 , cyano, or nitro; C 1 -C 8 alkyl substituted with CO 2 R 8 ; C 1 -C 18 alkoxy; C 1 -C 18 haloalkoxy; C 3 -C 18 alkynyloxy; C 3 -C 18 alkenyloxy; C 1 -C 18 alkylthio; C 3 -C 18 alkenylthio; or C 3 -C 18 alkynylthio;
  • R 2 is C 1 -C 18 alkyl; C 3 -C 7 cycloalkyl; C 3 -C 18
  • alkenyl C 3 -C 18 alkynyl; C 1 -C 18 haloalkyl;
  • nitroalkyl C 1 -C 8 alkyl substituted with CO 2 R 8 ; or phenyl, benzyl, or phenethyl each optionally substituted on the phenyl ring with R 13 ; or
  • R 1 and R 2 can be taken together along with the
  • R 3 and R 5 are each independently hydrogen; halogen;
  • R 4 and R 6 are each independently hydrogen; halogen;
  • R 7 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 8 and R 9 are each independently C 1 -C 4 alkyl
  • R 10 and R 11 are each independently H or C 1 -C 4 alkyl;
  • R 12 is C 1 -C 8 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 13 is halogen; C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkyl;
  • R 5 and R 6 is equal to or less than 16; iii) the total number of nitrogen atoms
  • 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: W is O; S; NH; or NR 9 ;
  • X is CR 3 ;
  • Y is CR 4 ;
  • R 1 is C 1 -C 8 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 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 2 -C 8 cyanoalkyl; C 1 -C 8 alkoxy; C 1 -C 18 haloalkoxy; C 3 -C 8 alkenyloxy; C 3 -C 8 alkenylthio; or C 4 -C 8 alkenyloxyalkyl;
  • R 2 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8
  • alkynyl C 1 -C 8 haloalkyl; C 2 -C 8
  • R 4 and R 6 are each independently hydrogen; halogen; C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 1 -C 8 haloalkyl; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 1 -C 8 alkylthio; C 1 -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; or cyano.
  • W is O; S; NH; or NMe
  • R 1 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8
  • alkynyl C 1 -C 8 haloalkyl; C 2 -C 8 halo- alkenyl; C 1 -C 8 alkoxy; C 2 -C 8 alkoxyalkyl; or C 3 -C 8 alkenyloxy;
  • R 2 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8
  • R 4 and R 6 are each independently hydrogen; halogen; C 1 -C 8 alkyl; C 1 -C 8 haloalkyl; C 1 -C 8 alkoxy; C 1 -C 8 haloalkoxy; C 3 -C 8 trialkylsilyl; or cyano.
  • R 1 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8
  • alkynyl C 1 -C 8 haloalkyl; or C 2 -C 8 haloalkenyl
  • R 2 is C 1 -C 8 alkyl; C 2 -C 8 alkenyl; C 2 -C 8
  • alkynyl C 1 -C 8 haloalkyl; C 2 -C 8
  • R 4 and R 6 are each independently hydrogen; halogen; C 1 -C 8 alkyl; C 1 -C 8 haloalkyl; C 1 -C 8 alkoxy; or C 1 -C 8 haloalkoxy.
  • 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.
  • cycloalkylthioalkyl are the cycloalkyl groups linked through a sulfur atom to an alkyl chain; e.g., cyclopropylthiopentyl.
  • Cycloalkylalkyl denotes a
  • cycloalkyl ring attached to a branched or straight-chain alkyl; e.g. cyclopropylmethyl and cyclohexylbutyl.
  • Alkenyl denotes straight chain or branched alkenes; e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl , pentenyl, hexenyl, etc.
  • Alkenyl also denotes polyenes such as
  • Alkynyl 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
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy,
  • alkoxyalkenyl and “alkoxyalkynyl” denoted groups in which the alkoxy group is bonded throught the oxygen atom to an alkenyl or alkynyl group, respectively. Examples include
  • CH 3 OCH 2 CH CH and (CH 3 ) 2 CHOCH 2 C ⁇ CCH 2 .
  • alkenylthioalkyl denotes the alkenylthio moieties bonded to an alkyl group.
  • H 2 C CHCH 2 SCH(CH 3 ) CH(CH 3 ) and
  • Alkynyloxy denotes straight or branched
  • alkynyloxy moieties examples include HC ⁇ CCH 2 O,
  • Alkynyloxyalkyl denotes alkynyloxy moieties bonded to alkyl groups; e.g.,
  • Alkynylthioalkyl denotes alkynylthio moieties bonded to alkyl groups.
  • Example include CH 3 C ⁇ CCH 2 SCH 2 CH 2 and CH 3 C ⁇ CCH 2 CH 2 SCH(CH 3 )CH 2 .
  • Alkylthio denotes methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and
  • alkylthioalkyl denotes alkylthio groups attached to an alkyl chain; e.g.,
  • Alkylsulfinyl denotes both enantiomers of an alkylsulfinyl group. For example, CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different
  • Alkylsulfinylalkyl denotes alkylsulfinyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(O)CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(O)CH 2 .
  • alkylsulfonyl examples include CH 3 S(O) 2 ,
  • alkylsulfonylalkyl denotes alkylsulfonyl groups attached to an alkyl chain; e.g.,
  • 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, ClCH 2 , CF 3 CH 2 and CF 3 CF 2 . Examples of
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C,
  • Haloalkynyloxyalkyl denotes haloalkynyl groups bonded through an oxygen atom to an alkyl moiety. Examples include CF 3 C ⁇ CCH 2 OCH 2 CH 2 ,
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, CF 2 HCH 2 CH 2 O and CF 3 CH 2 O.
  • Haloalkoxyalkyl denotes haloalkoxy groups bonded to straight-chain or branched alkyl groups; e.g.,
  • Trialkylsilyl designates a group with three alkyl groups bonded to silicon; e.g., (CH 3 ) 3 Si and
  • 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 .
  • C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " 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 O
  • C 3 alkoxyalkoxy designates, for example, CH 3 OCH 2 CH 2 O or
  • CH 3 CH 2 OCH 2 O; 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 O, and CH 3 CH 2 OCH 2 CH 2 O.
  • alkoxyalkyl examples include CH 3 OCH 2 , CH 3 OCH 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
  • Formula lb wherein G is S with a suitable oxidizing agent such as meta-chloroperoxybenzoic acid furnishes products of Formula Ic.
  • 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 (C H3 ) 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
  • 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.
  • base such as triethylamine
  • 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
  • n - is normal CN - is cyano
  • Me - is methyl S(O)Me - is methylsulfinyl Et - is ethyl S(O) 2 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
  • 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.
  • Granules and pellets can be made by
  • 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 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • the compounds and compositions of this invention are useful 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 are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These 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
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides,
  • insecticides such as monocrotophos, carbofuran, tetrachlorvinphos,
  • 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, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate,
  • fungicides such as carbendazim, thiuram, dodine, maneb, chloroneb, benomyl, cymoxanil, fenpropidine, fenpropimorph, triadimefon, captan, thiophanate-methyl, thiabendazole, phosethyl-Al, chlorothalonil, dichloran, metalaxyl, captafol, iprodione, oxadixyl, vinclozolin,
  • nematocides such as aldoxycarb, fenamiphos and
  • bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyrad and fenbutatin oxide; and biological agents such as Bacillus thuringiensis and baculovirus.
  • 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
  • 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 suspension was sprayed to the point of run-off on rice seedlings.
  • 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 suspension was sprayed to the point of run-off on tomato seedlings.
  • seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Phytophthora infestans the causal agent of potato and tomato late blight
  • 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 suspension was sprayed to the point of run-off on cucumber seedlings.
  • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (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.
PCT/US1993/004188 1992-05-13 1993-05-10 Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides WO1993023398A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP93911028A EP0640083A1 (fr) 1992-05-13 1993-05-10 Derives de pyrido 1,2-a]pyrimidinone substituee utiles comme fongicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US88221592A 1992-05-13 1992-05-13
US07/882,215 1992-05-13

Publications (1)

Publication Number Publication Date
WO1993023398A1 true WO1993023398A1 (fr) 1993-11-25

Family

ID=25380142

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/004188 WO1993023398A1 (fr) 1992-05-13 1993-05-10 Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides

Country Status (3)

Country Link
EP (1) EP0640083A1 (fr)
AU (1) AU4231293A (fr)
WO (1) WO1993023398A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110178077A1 (en) * 2008-06-17 2011-07-21 Priscille Brodin Anti-infective compounds
CN103260407A (zh) * 2010-12-27 2013-08-21 住友化学株式会社 节肢害虫防治组合物和用于防治节肢害虫的方法
WO2013119916A3 (fr) * 2012-02-10 2013-10-24 Ptc Therapeutics, Inc. Composés destinés au traitement de l'amyotrophie spinale
TWI489944B (zh) * 2009-08-05 2015-07-01 Du Pont 中離子殺蟲劑
US9371336B2 (en) 2012-03-01 2016-06-21 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
US9914722B2 (en) 2012-03-23 2018-03-13 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
US10195202B2 (en) 2013-12-19 2019-02-05 Ptc Therapeutics, Inc. Methods for modulating the amount of RNA transcripts
US10668171B2 (en) 2015-05-30 2020-06-02 Ptc Therapeutics, Inc. Methods for modulating RNA splicing
US10874672B2 (en) 2015-12-10 2020-12-29 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
CN113214249A (zh) * 2021-04-23 2021-08-06 成都大学 吡啶并[1,2-a]嘧啶-4-硫酮化合物的合成方法
US11382918B2 (en) 2017-06-28 2022-07-12 Ptc Therapeutics, Inc. Methods for treating Huntington's Disease
US11395822B2 (en) 2017-06-28 2022-07-26 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
US11407753B2 (en) 2017-06-05 2022-08-09 Ptc Therapeutics, Inc. Compounds for treating Huntington's disease
US11608501B2 (en) 2017-06-14 2023-03-21 Ptc Therapeutics, Inc. Methods for modifying RNA splicing
US11685746B2 (en) 2018-06-27 2023-06-27 Ptc Therapeutics, Inc. Heteroaryl compounds for treating Huntington's disease
US11702646B2 (en) 2016-11-28 2023-07-18 Ptc Therapeutics, Inc. Methods for modulating RNA splicing
US11780839B2 (en) 2018-03-27 2023-10-10 Ptc Therapeutics, Inc. Compounds for treating Huntington's disease
US11858941B2 (en) 2018-06-27 2024-01-02 Ptc Therapeutics, Inc. Heterocyclic and heteroaryl compounds for treating Huntington's disease

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE621702A (fr) * 1961-09-06 1962-12-17 Cutter Lab Composés de pyridopyrimidone
US3755582A (en) * 1971-03-04 1973-08-28 Du Pont Quinazolinone fungicides
CA1232904A (fr) * 1984-03-26 1988-02-16 Adi M. Treasurywala Pyrimidones substituees ayant des proprietes antifongiques
EP0339105A1 (fr) * 1986-10-28 1989-11-02 Nissan Chemical Industries Ltd. Composés hétérocycliques contenant de l'azote et compositions pour la lutte contre les parasites et/ou la prévention du mildiou

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE621702A (fr) * 1961-09-06 1962-12-17 Cutter Lab Composés de pyridopyrimidone
US3755582A (en) * 1971-03-04 1973-08-28 Du Pont Quinazolinone fungicides
CA1232904A (fr) * 1984-03-26 1988-02-16 Adi M. Treasurywala Pyrimidones substituees ayant des proprietes antifongiques
EP0339105A1 (fr) * 1986-10-28 1989-11-02 Nissan Chemical Industries Ltd. Composés hétérocycliques contenant de l'azote et compositions pour la lutte contre les parasites et/ou la prévention du mildiou

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 94, no. 2, 12 January 1981, Columbus, Ohio, US; abstract no. 15764s, '7-Alkoxythiazolo(3,2-a)pyrimidine derivatives' page 446 ; *
HELVETICA CHIMICA ACTA vol. 53, no. 5, 1970, BASEL CH pages 905 - 922 R. URBAN ET AL 'Alkylation des "malonyl-alpha-aminopyridines"' cited in the application *

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011524391A (ja) * 2008-06-17 2011-09-01 インスティチュート・パスツール・コリア 抗結核剤としてのピリドピリミジン化合物
US20110178077A1 (en) * 2008-06-17 2011-07-21 Priscille Brodin Anti-infective compounds
US8785452B2 (en) 2008-06-17 2014-07-22 Institut National De La Sante Et De La Recherche Medicale Anti-infective compounds
AU2009267519B2 (en) * 2008-06-17 2014-11-27 Institut National De La Sante Et De La Recherche Medicale Pyridopyrimidine compounds as anti-tubercular agents
TWI489944B (zh) * 2009-08-05 2015-07-01 Du Pont 中離子殺蟲劑
CN103260407A (zh) * 2010-12-27 2013-08-21 住友化学株式会社 节肢害虫防治组合物和用于防治节肢害虫的方法
EP2658380A1 (fr) * 2010-12-27 2013-11-06 Sumitomo Chemical Company Limited Composition et procédé de lutte contre les arthropodes nuisibles
EP2658380A4 (fr) * 2010-12-27 2014-05-28 Sumitomo Chemical Co Composition et procédé de lutte contre les arthropodes nuisibles
JP2015508075A (ja) * 2012-02-10 2015-03-16 ピーティーシー セラピューティクス， インコーポレイテッド 脊髄性筋萎縮症を治療するための化合物
US10851101B2 (en) 2012-02-10 2020-12-01 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
US9586955B2 (en) 2012-02-10 2017-03-07 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
JP2017122097A (ja) * 2012-02-10 2017-07-13 ピーティーシー セラピューティクス， インコーポレイテッド 脊髄性筋萎縮症を治療するための化合物
US9879007B2 (en) 2012-02-10 2018-01-30 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
EA029542B1 (ru) * 2012-02-10 2018-04-30 ПиТиСи ТЕРАПЬЮТИКС, ИНК. ПРОИЗВОДНЫЕ 4Н-ПИРИДО[1,2-а]ПИРИМИДИН-4-ОНА ДЛЯ ЛЕЧЕНИЯ СПИНАЛЬНОЙ МЫШЕЧНОЙ АТРОФИИ
US11753407B2 (en) 2012-02-10 2023-09-12 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
EA037123B1 (ru) * 2012-02-10 2021-02-09 ПиТиСи ТЕРАПЬЮТИКС, ИНК. Соединения для лечения спинальной мышечной атрофии
WO2013119916A3 (fr) * 2012-02-10 2013-10-24 Ptc Therapeutics, Inc. Composés destinés au traitement de l'amyotrophie spinale
US9371336B2 (en) 2012-03-01 2016-06-21 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
US9914722B2 (en) 2012-03-23 2018-03-13 Ptc Therapeutics, Inc. Compounds for treating spinal muscular atrophy
US10688099B2 (en) 2013-12-19 2020-06-23 Ptc Therapeutics, Inc. Methods for modulating the amount of RNA transcripts
US10195202B2 (en) 2013-12-19 2019-02-05 Ptc Therapeutics, Inc. Methods for modulating the amount of RNA transcripts
US10668171B2 (en) 2015-05-30 2020-06-02 Ptc Therapeutics, Inc. Methods for modulating RNA splicing
US11602567B2 (en) 2015-05-30 2023-03-14 Ptc Therapeutics, Inc. Methods for modulating RNA splicing
US10874672B2 (en) 2015-12-10 2020-12-29 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
US10881658B2 (en) 2015-12-10 2021-01-05 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
US11638706B2 (en) 2015-12-10 2023-05-02 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
US11702646B2 (en) 2016-11-28 2023-07-18 Ptc Therapeutics, Inc. Methods for modulating RNA splicing
US11407753B2 (en) 2017-06-05 2022-08-09 Ptc Therapeutics, Inc. Compounds for treating Huntington's disease
US11608501B2 (en) 2017-06-14 2023-03-21 Ptc Therapeutics, Inc. Methods for modifying RNA splicing
US11395822B2 (en) 2017-06-28 2022-07-26 Ptc Therapeutics, Inc. Methods for treating Huntington's disease
US11382918B2 (en) 2017-06-28 2022-07-12 Ptc Therapeutics, Inc. Methods for treating Huntington's Disease
US11780839B2 (en) 2018-03-27 2023-10-10 Ptc Therapeutics, Inc. Compounds for treating Huntington's disease
US11685746B2 (en) 2018-06-27 2023-06-27 Ptc Therapeutics, Inc. Heteroaryl compounds for treating Huntington's disease
US11858941B2 (en) 2018-06-27 2024-01-02 Ptc Therapeutics, Inc. Heterocyclic and heteroaryl compounds for treating Huntington's disease
CN113214249A (zh) * 2021-04-23 2021-08-06 成都大学 吡啶并[1,2-a]嘧啶-4-硫酮化合物的合成方法
CN113214249B (zh) * 2021-04-23 2023-09-19 成都大学 吡啶并[1,2-a]嘧啶-4-硫酮化合物的合成方法

Also Published As

Publication number Publication date
EP0640083A1 (fr) 1995-03-01
AU4231293A (en) 1993-12-13

Similar Documents

Publication Publication Date Title
EP0836602B1 (fr) Pyrimidinones fongicides
US5747497A (en) Fungicidal fused bicyclic pyrimidinones
WO1993023398A1 (fr) Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides
AU677448B2 (en) Fungicidal cyclic amides
EP0642502B1 (fr) Imidazolinones fongicides
WO1998026664A1 (fr) Quinazolinones fongicides
WO1996026191A1 (fr) Amides cycliques fongicides
EP0632803B1 (fr) Amides arthropodicides
WO2000051992A1 (fr) Fongicides d'oxazinone et de thiazinone bicycliques fusionnes
EP0630370A1 (fr) Oxazolidinones fongicides
WO1993022311A1 (fr) 1,3,4-oxadiazines et 1,3,4-thiadiazines fongicides
EP0623125A1 (fr) Fongicides heterocycliques pontes
WO2000008026A2 (fr) Hétérocycles bicycliques fondus fongicides
WO1992019615A2 (fr) Pyrazoles, pyrazolines et tetrahydropyridazines fongicides
WO1999011129A1 (fr) Compositions enantiomeriquement enrichies et leur utilisation pesticide
EP0869963A1 (fr) Organosilanes et organogermanes arthropodicides et fongicides
WO1998020003A1 (fr) Amides cycliques fongicides
US6255311B1 (en) Fungicidal fused bicyclic pyrimidinones
USH1829H (en) Fungicidal fused bicyclic pyrimidinones
US5514678A (en) Arthropodicidal 1,2,4-triazinyl amides
JP2003528848A (ja) 殺節足動物性カルボキシアニリド類

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR CA CZ FI HU JP KP KR KZ LK MG MN MW NO NZ PL RO RU SD SK UA US VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
EX32 Extension under rule 32 effected after completion of technical preparation for international publication

Ref country code: BY

LE32 Later election for international application filed prior to expiration of 19th month from priority date or according to rule 32.2 (b)

Ref country code: BY

WWE Wipo information: entry into national phase

Ref document number: 1993911028

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1993911028

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1993911028

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: CA