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WO1994004527A1 - Derives pyridylethoxy, pyridylethylamino, et pyridylpropyle de quinoline et de quinazoline utilises comme insecticides et fongicides - Google Patents

Derives pyridylethoxy, pyridylethylamino, et pyridylpropyle de quinoline et de quinazoline utilises comme insecticides et fongicides Download PDF

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Publication number
WO1994004527A1
WO1994004527A1 PCT/US1993/007120 US9307120W WO9404527A1 WO 1994004527 A1 WO1994004527 A1 WO 1994004527A1 US 9307120 W US9307120 W US 9307120W WO 9404527 A1 WO9404527 A1 WO 9404527A1
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Prior art keywords
compound
alkyl
halo
compounds
phenyl
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PCT/US1993/007120
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English (en)
Inventor
Barry A. Dreikorn
Robert G. Suhr
Peter L. Johnson
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Dowelanco
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Publication date
Application filed by Dowelanco filed Critical Dowelanco
Priority to AU47908/93A priority Critical patent/AU4790893A/en
Publication of WO1994004527A1 publication Critical patent/WO1994004527A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • This invention provides new organic compounds having exceptional insecticidal, miticidal, nematicidal, and fungicidal activity.
  • the invention also provides new pesticide methods and compositions utilizing the new compounds.
  • the invention provides new compounds of the formula (1) :
  • X 1 is N or CR 1 ;
  • R 1 are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, NO 2 , CN, lower alkoxy- carbonyl;
  • Y is CH 2 , NR 3 , or 0, where R 3 is selected from H, lower alkyl, lower alkyl-carbonyl, lower alkyl-carbonyloxy, SOq- lower alkyl, SOq-phenyl or substituted phenyl; and q is an integer from 0 to 2;
  • one of X 2 and X 3 is N and the other is CR 1 ;
  • R 2 is -Z-R 4 , phenyl, or substituted phenyl
  • Z is 0 or S
  • R 4 is (C 1 -C 4 ) alkyl, (C 3 -C 7 ) branched alkyl, halo (C 1 -C 7 ) alkyl, halo (C 3 -C 7 ) branched alkyl, (C 1 -C 4 ) alkoxy substituted (C 1 -C 4 ) alkyl, or naphthyl or phenyl, either of which may
  • TESHEET optionally be substituted with up to three groups selected from halo, (Ci-Cio) alkyl, branched (C3-C7) alkyl, halo(C ⁇ -C7) alkyl, hydroxy (C 1 -C 7 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy, O-phenyl, O-substituted phenyl, phenyl, substituted phenyl, naphthyl, CN, NO 2 , OH, (C 1 -C 4 ) alkanoyloxy, or benzyloxy.
  • the invention also provides new pesticide methods and compositions utilizing the compounds of formula (1) .
  • halo refers to F, Cl, Br, and I atoms.
  • lower alkyl refers to Cl to C6 straight hydrocarbon chains and C3 to C6 branched and cyclic hydrocarbon groups.
  • lower alkenyl and “lower alkynyl” refer to C2 to C6 straight hydrocarbon chains and C3 to C6 branched hydrocarbon groups containing at least one unsaturated bond.
  • haloalkyl refers to lower alkyl groups substituted with one or more halo atoms.
  • haloalkoxy refers to lower alkoxy groups substituted with one or more halo atoms.
  • substituted phenyl refers to groups wherein the phenyl ring is substituted with lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo, hydroxy, NO 2 , haloalkyl, haloalkoxy, haloalkylthio, CN, phenyl, substituted phenyl, -O-phenyl, -O-substituted phenyl, C1-C 4 alkanoyloxy, benzyloxy, or S(0) p -lower alkyl, where p is 0-2.
  • HPLC refers to a high pressure liquid chromatography
  • R 1 are selected from H and F
  • the compounds of this invention are made using well known chemical procedures.
  • the required starting materials are commercially available or are readily synthesized using standard procedures.
  • the compounds of formula (1) wherein Y is 0 can be made by condensing a compound of formula (4)
  • L is a leaving group, such as F, Cl, Br, I, NO 2 , 1,2,3-triazol-l-yl, 1,2,4-triazol-l-yl, 0SiMe 3 , arylthio, alkylthio, alkylsulfonyl, arylsulfonyl, alkoxy, or arylsulfinyl; with an alcohol of the formu
  • R 2 , X 2 , and X 3 are as defined for formula (1) .
  • the reaction is preferably carried out in the presence of a strong base, such as sodium hydride, in a non-reactive solvent, such as DMF, at a temperature in the range of 0 to 25°C.
  • a strong base such as sodium hydride
  • a non-reactive solvent such as DMF
  • R 2 , X 2 , and X 3 are as defined for formula (1) and R3 is H or lower alkyl.
  • the compound of formula (4) is allowed to react with the amine at a temperature in the range 20-180°C, preferably in the presence of an acid acceptor, such a triethylamine.
  • the reaction may be carried out neat, or in a nonreactive organic solvent.
  • R 2 , X 2 , and X 3 are as defined for formula (1) . and X' is halo; to provide a 3,4-dihydro quinazoline or quinoline, which is then oxidized.
  • Compounds of formula (1) wherein Y is CH 2 may also be prepared by reacting a compound of formula (7) with a lithio reagent of the formula (9)
  • R 2 , X 2 , and X 3 are as defined for formula (1) to provide a 3,4-dihydro quinazoline or quinoline, which is then oxidized.
  • the desired compound of the invention may then be separated from other products using conventional means. Typical reaction conditions are those described in Armarego and Smith, J. Chem Soc.. page 5360 (1965) .
  • the compounds of formula (1) wherein Y is CH 2 can also be made by reacting a compound (10)
  • X 1 and R 1 are as defined for formula (1) ; with an aprotic organolithium base, especially lithium diisopropylamide, in a polar aprotic solvent and then reacting with a compound of the formula (11)
  • variable substituents are as defined for formula (1) .
  • the barbituric acid derivative is dissolved in a solution of sodium hydroxide and water and refluxed. The solution is then made slightly acidic and again refluxed.
  • step 1 KOH hydrolysis of the nitrile produces the corresponding carboxylic acid.
  • step 2 lithium aluminum hydride reduction of the carboxylic acid produces the alcohol, Alternatively, the alcohol can be obtained by sodium borohydride reduction of the corresponding aldehyde.
  • the halogenation illustrated in step 3 may be, for example, chlorination with thionyl chloride.
  • Step 5 is a lithium aluminum hydride reduction of the nitrile using a Lewis acid such as H 2 SO 4 or AICI 3 .
  • step 6 hydrolysis of the nitrile gives the pyridylacetic acid derivative, which is reduced to the pyridylethyl alcohol in step 7 using lithium aluminum hydride or other conventional reducing agents.
  • Lithium aluminum hydride (3.70 g, 92.5 mmol) was added in one portion to a stirred solution of aluminum chloride (12.33 g, 92.5 mmol) in 150 mL of ethyl ether, under nitrogen, at 0°C The mixture was stirred for about 15 minutes, then treated dropwise with a solution of (2- (2,2,2- trifluoroethoxy) -5-pyridyl)acetonitrile (20.00 g, 92.5 mmol) in 50 mL of ethyl ether. After the addition was complete the mixture was allowed to warm to room temperature and stirred at room temperature for about two hours.
  • the compounds of the present invention have been found to control fungi, particularly plant pathogens.
  • the compounds When employed in the treatment of plant fungal diseases, the compounds are applied to the plants in a disease inhibiting and phytologically acceptable amount.
  • the exact concentration of compound required varies with the fungal disease to be controlled, the type formulation employed, the method of application, the particular plant species, climate conditions and the like. A suitable application rate is typically in the range from .25 to 4 lb/A.
  • the compounds of the invention may also be used to protect stored grain and other non-plant loci from fungal infestation.
  • Representative fungal disease organisms controlled include: Alternaria bra ⁇ sicicola (leaf spot of brassicas) , Alternaria mali (leaf spot of apples) , Alternaria tenuis (leaf spot) , Botryti ⁇ cinerea (grey mold) , Cochliobolus sativus (spot blotch) ,
  • Colletotrichum coffeanum (coffee berry disease) , Colletotrichum lindemuthianum (anthracnose of bean) , Ery ⁇ iphe graminis hordeii (barley powdery mildew) , Erysiphe graminis tri tici (wheat powdery mildew) , Fusariu culmorum (head blight) ,
  • Rhizoctonia cerealis (sharp eyespot of wheat) .
  • Rhizoctonia solani sheath blight
  • Rhynco ⁇ porium secalis leaf scald
  • Uncinula necator (grape powdery mildew)
  • Ustilago maydis (bunt of wheat)
  • Verticillium albo-atrum (wilt of tomatoes)
  • Venturia inaegualis (apple scab) .
  • test compounds were formulated for application by dissolving 50 mg of the compound into 1.25 ml of solvent.
  • the solvent was prepared by mixing 50 ml of "Tween 20" (polyoxyethylene (20) sorbitan monolaurate emulsifier) with 475 ml of acetone and 475 ml of ethanol.
  • the solvent/compound solution was diluted to 125 ml with deionized water.
  • the resulting formulation contains 400 ppm test chemical. Lower concentrations were obtained by serial dilution with the solvent-surfactant mixture.
  • test compounds were applied by foliar spray.
  • the following plant pathogens and their corresponding plants were employed.
  • Puccinia recondita PUCCRT wheat tritici (leaf rust)
  • Leptosphaeria nodorum LEPTNO wheat (glume blotch)
  • the formulated technical compounds were sprayed on all foliar surfaces of the host plants to past run-off. Single pots of each host plant were placed on raised, revolving pedestals in a fume hood. Test solutions were sprayed on all foliar surfaces. All treatments were allowed to dry and the plants were inoculated with the appropriate pathogens within 24 hours.
  • Table II reports the activity of typical compounds of the present invention when evaluated in this experiment. The effectiveness of test compounds in controlling disease was rated using the following scale.
  • the compounds of formula (1) show activity against a number of insects, mites, and nematodes. More specifically, the compounds show activity against cotton aphid, which is a member of the insect order Homoptera. Other members of the Homoptera include leafhoppers, planthoppers, pear pyslla, apple sucker, scale insects, whiteflies, spittle bugs as well as numerous other host specific aphid species. Activity has also been observed against greenhouse thrips, which are members of the order Thysanoptera. The compounds also show activity against Southern armyworm, which is a member of the insect order Lepidoptera .
  • mice codling moth, cutworm, clothes moth, Indian meal moth, leaf rollers, corn earworm, European corn borer, cabbage worm, cabbage looper, cotton bollworm, bagworm, eastern tent caterpillar,beet armyworm, tobacco budworm, sod webworm, and fall armyworm.
  • the compounds also show activity against German cockroach, which is a member of the order Orthoptera.
  • Other typical members of this order are Asian cockroach, oriental cockroach, American cockroach, lubber grasshopper, differential grasshopper, redlegged grasshopper, migratory grasshopper, American grasshopper, vagrant grasshopper, and house cricket.
  • the compounds also show activity against corn rootworm, which is a member of the order Coleoptera .
  • the compounds of formula (1) are useful for reducing populations of insects, mites, and nematodes and are used in a method of inhibiting an insect, mite, or nematode population which comprises applying to a locus of the insect, mite, or nematode an effective insect-, mite-, or nematode-inactivating amount of a compound of formula (1) .
  • locus of insects, mites, or nematodes is a term used herein to refer to the
  • insect-ingesting insects or mites can be controlled by applying the active compound to plant parts, which the insects or mites eat, particularly the foliage. It is contemplated that the compounds might also be useful to protect textiles, paper, stored grain, or seeds by applying an active compound to such substance.
  • inhibiting an insect, mite, or nematode refers to a decrease in the numbers of living insects, mites or nematodes; or a decrease in the number of viable insect, mite, or nematode eggs.
  • the extent of reduction accomplished by a compound depends, of course, upon the application rate of the compound, the particular compound used, and the target insect, mite, or nematode species. At least an insect-inactivating, mite-inactivating or nematode inactivating amount should be used.
  • the terms "insect-inactivating amount”, “mite-inactivating amount” and “nematode-inactivating amount” are used to describe the amount, which is sufficient to cause a measurable reduction in the treated insect, mite, or nematode population. Generally an amount in the range from about 1 to about 1000 ppm active compound is used.
  • CA cotton aphid
  • NEM peanut rootknot nematode
  • SCRW southern corn rootworm
  • TBW tobacco budworm
  • TSSM tobacco budworm
  • GECR refers to German cockroach
  • each test compound was formulated as a 400 ppm solution, and this solution was then diluted with water to give lesser concentrations.
  • the 400 ppm solution was prepared by combining 19.2 mL of .05% solution of Tween 20
  • Activity against aster leafhopper was tested as follows. The test was run using concentrations of 400 ppm and 50 ppm. One ounce plastic cups containing a cotton wick was sprayed with 0.4 mL of formulated material using a flat-fan nozzle. The excess moisture was allowed to evaporate. Then five to ten carbon dioxide anesthetized adult leafhoppers were added to each cup. The cups were capped and held at room temperature for 24 hours. Percent mortality was then determined.
  • Activity against beet armyworm was evaluated as follows. The test is run using concentrations of 400 ppm and 50 ppm. A general purpose lepidoptera artificial diet was diluted to half strength with a 5% non nutritive agar. 8 mL of this diet material was dispensed into one ounce diet cups. One hour prior to treatment, 35 to 40 eggs were dispensed onto the diet surface. The cups were then sprayed with formulated material through a flat-fan nozzle. Treated cups were air dried prior to sealing with plastic caps. The cups were held for 6 days at room temperature. Activity was then rated based on the total number of live and dead larvae, and on the size of live larvae.
  • Activity against peanut rootknot nematode was evaluated as follows. Five untreated cucumber seeds are placed into the bottom of a clear one ounce cup, 20 g of clean white sand is added, and the cups were sprayed while rotating on a pedestal allowing 1.0 mL of a 400 ppm solution to be deposited on the sand. To each cup was dispensed 2.5 to 3.0 mL of deionized water containing 300 to 500 nematodes. The cups were held for 10 to 12 days in an environmental growth chamber at a temperature of 76 to 85 °F and ambient humidity of 50 to 60%. After 10 to 12 days the cups were evaluated by inverting the cup and observing nematode mortality and feeding damage to the cucumber plants.
  • Activity against tobacco budworm was evaluated as follows. A general purpose lepidoptera artificial diet was diluted to half strength with a 5% non nutritive agar. 8 mL of this diet material was dispensed into each one ounce diet cup. One hour prior to treatment 18 to 20 eggs were dispensed onto the diet surface. The cups were then
  • Activity was then rated based on the total number of live and dead insects.
  • compositions which are important embodiments of the invention, and which comprise a compound of formula (1) and a phytologically-acceptable inert carrier.
  • the compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations which
  • compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of the compounds of this invention. Some description of the formulation of the compositions will be given, however, to assure that agricultural chemists can readily prepare any desired composition.
  • the dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds.
  • Such water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates or aqueous suspensions.
  • Wettable powders which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants.
  • the concentration of the active compound is usually from about 10% to about 90% by weight.
  • the inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates.
  • Effective surfactants comprising from about 0.5% to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phenols.
  • Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 10% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers.
  • a compound such as from about 50 to about 500 grams per liter of liquid, equivalent to about 10% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers.
  • Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha.
  • Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives,
  • Suitable emulsifiers for emulsifi ⁇ able concentrates are chosen from conventional nonionic surfactants, such as those discussed above.
  • Aqueous suspensions comprise suspensions of water-insoluble compounds of this invention, dispersed in an aqueous vehicle at a concentration in the range from about 5% to about 50% by weight.
  • Suspensions are prepared by finely grinding the compound, and vigorously mixing it into a vehicle comprised of water and surfactants chosen from the same types discussed above.
  • Inert ingredients such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous vehicle. It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.
  • the compounds may also be applied as granular compositions, which are particularly useful for applications to the soil.
  • Granular compositions usually contain from about 0.5% to about 10% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance.
  • Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been pre-formed to the appropriate particle size, in the range of from about 0.5 to 3 mm.
  • Such compositions may also be formulated by making a dough or paste of the carrier and compound, and crushing and drying to obtain the desired granular particle size.
  • Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the like. Dusts can suitably contain from about 1% to about 10% of the compound.
  • Insecticides and miticides are generally applied in the form of a dispersion of the active ingredient in a liquid carrier. It is conventional to refer to application rates in terms of the concentration of active ingredient in the carrier. The most widely used carrier is water.
  • the compounds of formula (1) can also be applied in the form of an aerosol composition.
  • the active compound is dissolved or dispersed in an inert carrier, which is a pressure-generating propellant mixture.
  • the aerosol composition is packaged in a container from which the mixture is dispensed through an atomizing valve.
  • Propellant mixtures comprise either low-boiling halocarbons, which may be mixed with organic solvents, or aqueous suspensions pressurized with inert gases or gaseous hydrocarbons.
  • the actual amount of compound to be applied to loci of insects and mites is not critical and can readily be determined by those skilled in the art in view of the examples above. In general, concentrations of from 10 ppm to 5000 ppm of compound are expected to provide good control. With many of the compounds, concentrations of from 100 to 1500 ppm will suffice.
  • a suitable application rate for the compounds is about 0.5 to 1.5 lb/A, typically applied in 50 gal/A of spray formulation containing 1200 to 3600 ppm of compound.
  • a suitable application rate is from about 100 to 1500 gal/A spray formulation, which is a rate of 100 to 1000 ppm.
  • the locus to which a compound is applied can be any locus inhabited by an insect or arachnid, for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants. Inasmuch as many mite species are specific to a particular host, the foregoing list of mite species provides

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  • Life Sciences & Earth Sciences (AREA)
  • 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)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Des dérivés pyridyléthoxy, pyridyléthylamino, et pyridylpropyle de quinoline et de quinazoline, par exemple N-(2-(2-(2,2,2-trifluoréthoxy)-5-pyridyl)éthyl)-8-fluoroquinazoline-4-amine, présentent une activité insecticide, antimite, antinématode et fongicide.
PCT/US1993/007120 1992-08-19 1993-07-29 Derives pyridylethoxy, pyridylethylamino, et pyridylpropyle de quinoline et de quinazoline utilises comme insecticides et fongicides WO1994004527A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47908/93A AU4790893A (en) 1992-08-19 1993-07-29 Pyridylethoxy-, pyridylethylamino-, and pyridylpropyl-derivatives of quinoline and quinazoline as insecticides and fungicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93239792A 1992-08-19 1992-08-19
US07/932,397 1992-08-19

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WO1994004527A1 true WO1994004527A1 (fr) 1994-03-03

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CN (1) CN1083811A (fr)
AU (1) AU4790893A (fr)
IL (1) IL106723A0 (fr)
MX (1) MX9305026A (fr)
WO (1) WO1994004527A1 (fr)

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WO1997010215A1 (fr) * 1995-09-12 1997-03-20 Basf Aktiengesellschaft Fongicides quinoleiques
US6521618B2 (en) 2000-03-28 2003-02-18 Wyeth 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors
WO2010025451A2 (fr) * 2008-08-29 2010-03-04 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(hétéroaryloxy)-phényle) éthylamino) quinazolines et leur utilisation en tant que produits agrochimiques
WO2011025505A1 (fr) * 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
WO2014063642A1 (fr) 2012-10-25 2014-05-01 中国中化股份有限公司 Composé à pyrimidines substituées et ses applications
US8895568B2 (en) 2009-08-31 2014-11-25 Dow Agrosciences, Llc. Compositions comprising substituted pteridines as agrochemicals
US10487091B2 (en) 2015-10-05 2019-11-26 The Trustees Of Columbia University In The City Of New York Activators of autophagic flux and phospholipase D and clearance of protein aggregates including tau and treatment of proteinopathies

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326331A2 (fr) * 1988-01-29 1989-08-02 DowElanco Quinoléines et cinnolines substituées
EP0326329A2 (fr) * 1988-01-29 1989-08-02 DowElanco Dérivés de quinazoline
EP0326328A2 (fr) * 1988-01-29 1989-08-02 DowElanco Dérivés de quinoléine, quinazoline et cinnolines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326331A2 (fr) * 1988-01-29 1989-08-02 DowElanco Quinoléines et cinnolines substituées
EP0326329A2 (fr) * 1988-01-29 1989-08-02 DowElanco Dérivés de quinazoline
EP0326328A2 (fr) * 1988-01-29 1989-08-02 DowElanco Dérivés de quinoléine, quinazoline et cinnolines

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997010215A1 (fr) * 1995-09-12 1997-03-20 Basf Aktiengesellschaft Fongicides quinoleiques
US5955473A (en) * 1995-09-12 1999-09-21 Basf Aktiengesellschaft Fungicidal quinolines
US6521618B2 (en) 2000-03-28 2003-02-18 Wyeth 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors
US6689772B1 (en) 2000-03-28 2004-02-10 Wyeth 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors
US8268843B2 (en) 2008-08-29 2012-09-18 Dow Agrosciences, Llc. 5,8-difluoro-4-(2-(4-(heteroaryloxy)-phenyl)ethylamino)quinazolines and their use as agrochemicals
US9000162B2 (en) 2008-08-29 2015-04-07 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(heteroaryloxy)-phenyl)ethylamino)quinazolines and their use as agrochemicals
WO2010025451A3 (fr) * 2008-08-29 2010-06-17 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(hétéroaryloxy)-phényle) éthylamino) quinazolines et leur utilisation en tant que produits agrochimiques
WO2010025451A2 (fr) * 2008-08-29 2010-03-04 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(hétéroaryloxy)-phényle) éthylamino) quinazolines et leur utilisation en tant que produits agrochimiques
CN102574855A (zh) * 2009-08-31 2012-07-11 陶氏益农公司 喋啶和它们作为农药的用途
US8895568B2 (en) 2009-08-31 2014-11-25 Dow Agrosciences, Llc. Compositions comprising substituted pteridines as agrochemicals
WO2011025505A1 (fr) * 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
EA022487B1 (ru) * 2009-08-31 2016-01-29 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Птеридины, полезные в качестве агрохимикатов и продуктов для здоровья животных
WO2014063642A1 (fr) 2012-10-25 2014-05-01 中国中化股份有限公司 Composé à pyrimidines substituées et ses applications
US10487091B2 (en) 2015-10-05 2019-11-26 The Trustees Of Columbia University In The City Of New York Activators of autophagic flux and phospholipase D and clearance of protein aggregates including tau and treatment of proteinopathies
US10865214B2 (en) 2015-10-05 2020-12-15 The Trustees of Columbia University in they City of New York Activators of autophagic flux and phospholipase D and clearance of protein aggregates including tau and treatment of proteinopathies
US11008341B2 (en) 2015-10-05 2021-05-18 The Trustees Of Columbia University In The City Of New York Activators of autophagic flux and phospholipase D and clearance of protein aggregates including tau and treatment of proteinopathies
US11230558B2 (en) 2015-10-05 2022-01-25 The Trustees Of Columbia University In The City Of New York Activators of autophagic flux and phospholipase D and clearance of protein aggregates including tau and treatment of proteinopathies
US11261199B2 (en) 2015-10-05 2022-03-01 The Trustees Of Columbia University In The City Of New York Activators of autophagic flux and phospholipase d and clearance of protein aggregates including tau and treatment of proteinopathies

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IL106723A0 (en) 1993-12-08
AU4790893A (en) 1994-03-15
CN1083811A (zh) 1994-03-16
MX9305026A (es) 1994-03-31

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