WO1993022291A1 - Aminopyrimidines arthropidicides et fongicides - Google Patents

Aminopyrimidines arthropidicides et fongicides Download PDF

Info

Publication number
WO1993022291A1
WO1993022291A1 PCT/US1993/002757 US9302757W WO9322291A1 WO 1993022291 A1 WO1993022291 A1 WO 1993022291A1 US 9302757 W US9302757 W US 9302757W WO 9322291 A1 WO9322291 A1 WO 9322291A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
haloalkyl
optionally substituted
halogen
alkoxyalkyl
Prior art date
Application number
PCT/US1993/002757
Other languages
English (en)
Inventor
Renée Marie LETT
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
Publication of WO1993022291A1 publication Critical patent/WO1993022291A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/30—Germanium compounds

Definitions

  • This invention relates to aminopyrimidines
  • U.S. 4,895,849, U.S. 4,985,426, U.S. 4,435,402 and EP 424,125 each disclose aminopyrimidines useful as insecticides having substituents at the claimed R 3 position limited to H, halogen or lower alkyl.
  • DE 3,905,364 discloses certain aminopyrimidines as aldose reductase inhibitors.
  • This invention comprises compounds of Formula I, including all geometric and stereoisomers,
  • A is C 1 -C 5 straight or branched chain alkylene or C 3 -C 6 cycloalkylene, wherein any one atom of A can be optionally substituted with R 7 ;
  • X is Ge or Si;
  • R 1 is H, halogen, C 1 -C 4 -alkyl or C 1 -C 4 haloalkyl
  • R 2 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 4 cyanoalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 alkylthioalkyl;
  • R 3 is H, halogen, CN, NO 2 , CO 2 R 16 , C(O)R 16 ,
  • R 4 is H, formyl, C 2 -C 6 alkoxyalkyl C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6
  • haloalkoxycarbonyl C(O)R 15 , R 11 OC(O)S-, R 11 OC(O)N(R 12 )S-, R 11 (R 12 )NS- or SR 8 ; or R 4 is C 1 -C 6 alkyl optionally substituted with halogen, CN, NO 2 , S(O) n R 11 , C(O)R 11 , CO 2 R 11 or C 1 -C 3 haloalkoxy; or R 4 is phenyl optionally substituted with halogen, CN, and C 1 -C 2 haloalkyl;
  • R 5 is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 alkenyl, C 2 -C6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylalkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylthioalkyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 hal
  • R 6 is H, halogen, CN, NO 2 , C 1 -C 2 alkyl, C 1 -C 2 alkoxy or CF 3 ;
  • R 7 is CN, C(O)R 8 , CO 2 R 8 , C(O)N(R 8 )R 9 , N 3 , NO 2 ,
  • R 8 and R 10 are independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 1 -C 6 nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl optionally substituted with W; or benzyl optionally substituted with W on the phenyl ring;
  • R 9 is H or C 1 -C 4 alkyl
  • R 8 and R 9 can be taken together when attached to the same atom as -(CH 2 ) 4 -, -(CH 2 ) 5 - or
  • R 11 and R 12 are independently C 1 -C 4 alkyl
  • R 13 is C 1 -C 4 alkyl, C 1 -C 4 alkoxyalkyl or phenyl
  • R 14 is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, phenyl or benzyl, each phenyl or benzyl
  • R 15 is , , or ;
  • R 16 and R 17 are independently H, C 1 -C 4 alkyl or
  • W is CN, NO 2 , C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio, C 1 -C 2 alkylsulfonyl, C 1 -C 2 haloalkylsulfonyl or 1-5 halogens; and
  • n 0, 1 or 2.
  • Preferred Compounds A are compounds of Formula I
  • A is C 1 -C 5 straight or branched alkylene
  • R 1 is H
  • R 2 is C 1 -C 6 alkyl, C 2 -C 4 cyanoalkyl or C 1 -C 4 haloalkyl; R 4 is H;
  • R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkoxyalkoxy or phenoxy optionally substituted with W;
  • R 6 is H, halogen or C 1 -C 2 alkyl;
  • R 11 , R 12 and R 13 are independently C 2 -C 2
  • R 14 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy or phenyl
  • W is halogen or C 1 -C 2 haloalkyl.
  • Preferred Compounds B are compounds of Preferred A wherein Q is Q-1.
  • Preferred Compounds C are compounds of Preferred A wherein Q is Q-2.
  • Preferred Compounds D are compounds of Preferred A wherein Q is Q-3.
  • the present invention further comprises
  • compositions containing an effective amount of one or more compounds of Formula I and at least one of (a) a surfactant (b) an organic solvent, and (c) at least one solid or liquid diluent.
  • the present-invention further comprises a method for controlling foliar, aquatic and soil-inhabiting anthropod pests comprising application of an effective amount of a compound of Formula I or an agricultural composition as described above containing one or more compounds of Formula I to the locus of infestation, area to be protected, or directly onto said pests.
  • stereoisomers are meant all of the isomers of the Formula I compounds which include enantiomers, diastereomers, and geometric isomers.
  • enantiomers diastereomers
  • geometric isomers One skilled in the art will appreciate that one or the other of said stereoisomer (s) will be the more active. It is also known how to separate such enantiomers, diastereomers, and geometric isomers.
  • the present invention comprises racemic mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in a compound word such as “alkylthio” or “haloalkyl”, denotes straight or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl, or the different butyl, pentyl or hexyl isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy or hexyloxy isomers.
  • Alkenyl denotes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.
  • Alkynyl denotes straight chain or branched alkynes such as ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkylthio denotes methylthio, ethylthio and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl, alkylsulfonyl, alkylamino, etc. are defined analogously to the above examples.
  • Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • 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 CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • halocycloalkyl “haloalkenyl” and “haloalkynyl” are defined analogously to the term “haloalkyl”.
  • 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 8.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkoxy designates OCH 2 OCH 3
  • 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
  • cyanoalkyl designates CH 2 CN and C 3 cyanoalkyl
  • C 2 alkylcarbonyl would designates C(O)CH 3 and C 4 alkylcarbonyl includes C(O)CH 2 CH 2 CH 3 and C(O) CH (CH 3 ) 2 ; and as a final example, C 3 alkoxycarbonylalkyl designates CH 2 CO 2 CH 3 and C 4 alkoxycarbonylalkyl includes CH 2 CH 2 CO 2 CH 3 , CH 2 CO 2 CH 2 CH 3 and CH(CH 3 )CO 2 CH 3 .
  • insects include insects, mites and nematodes.
  • Z represents a displaceable group such as a halogen atom, an alkylthio group, or an alkyl- or arylsulfonyloxy group;
  • A, Q, R 2 and R 3 are as previously defined for Formula I .
  • the reaction of pyrimidine II with amine III is best carried out in the presence of an acid acceptor or base.
  • the base can be, but is not limited to, triethylamine, pyridine, sodium hydride, or potassium carbonate.
  • the synthetic process can be carried out in the absence or presence of a solvent. Suitable
  • solvents include those that will not participate in the above reaction, for example, toluene, xylene, ethanol, propanol, N,N-dimethylformamide, and N,N-dimethylacetamide.
  • Preferred temperatures for this process are from about 20°C to 200°C with temperatures between 80°C and 150°C being particularly preferred.
  • Compounds of Formula I where R 4 is an alkyl or acyl group can be best prepared by reacting an amine of Formula III where R 4 is an alkyl or acyl group with a pyrimidine of Formula II.
  • the amine of Formula III where R 4 is alkyl or acyl can be prepared by acylating or alkylating an amine of Formula III, where R 4 is equal to hydrogen, using conventional methods known to those skilled in the art.
  • Amines of Formula III wherein A is equal to CH 2 CH 2 can be prepared by reduction of nitriles of Formula IV using alane. In situ formation of alane in ether and then treatment with nitrile IV at 0°C gives the desired primary amines in high yields. Nitriles of Formula IV can in turn be synthesized by the displacement of a bromine atom from a bromide of Formula V with potassium cyanide as in Scheme 3, wherein Q is as previously defined for Formula I. SCHEME 3
  • Bromides of Formula V can be prepared according to the process shown in Scheme 4, wherein Q is as previously defined in Formula I, and NBS is N-bromosuccinimide.
  • Aryl methyl groups in compounds of Formula VI are subject to free radical bromination by N-bromosuccinimide (NBS) in the presence of light.
  • NBS N-bromosuccinimide
  • the dibromides can, in turn, be prepared from compounds of Formula VI.
  • Aryl methyl compounds of Formula VI are subject to free radical bromination with two equivalents of N-bromosuccinimide in the presence of light in refluxing carbon tetrachloride according to Scheme 7, wherein Q is as previously defined in
  • Pyrimidines of Formula II can be prepared by a variety of literature methods. Some efficient
  • Some pyrimidines of Formula II where R 3 is equal to halogen or nitro can be prepared by the reaction of a 4-pyrimidinol with an electrophile (Scheme 8). Electrophilic reagents that transfer halogen
  • pyrimidines of Formula II can be prepared by simple functional group transformations using
  • Palladium complexes of triarylphosphines are the preferred catalysts of this reaction.
  • Some examples are tetrakis (triphenylphosphine)pallpadium(O), bis (triphenylphosphine)palladium(II)dichloride, and tris- (dibenzylideneacetone)dipalladium(O) with 1,1'-bis
  • the reaction can be carried out in a variety of solvents including dimethylsulfoxide, dimethylformamide, triethylamine, tetrahydrofuran, dioxane, and toluene.
  • the temperature of the reaction is determined by the nature of the catalyst and displaceable group R 3 . Generally the reaction is carried out at temperatures in the range of 25°C to 200°C with temperatures of 60°C to 150°C being preferred.
  • reagents MR 3 are potassium cyanide, cuprous iodide with trimethylsilylacetylene, and vinyltrimethyltin. Detailed procedures are
  • R 3 is equal to CO 2 R 16 , C(O)R 16 , and CHO.
  • 6-ethyl-4-pyrimidinol (1.2 g, 10 mmole) and N-iodosuccinimide (2.2 g, 10 mmole) were heated at 61°C in chloroform (20 mL) for four hours.
  • the reaction mixture was cooled and concentrated under vacuum to a solid residue.
  • the crude solid was treated with hot water and filtered.
  • the moist solid was recrystallized from methanol to give a pure white solid product
  • Step B 4-chloro-6-ethyl-5-iodopyrimidine
  • Step C 6-ethyl-5-iodo-N-[1-[4-(trimethylsilyl)-phenyl]ethyl]-4-pyrimidinamine
  • Step B The product of Step B (1.5 g, 5.6 mmole), ⁇ -methyl-4-trimethylsilylbenzenemethanamine (1.1 g, 5.6 mmole), and triethylamine (1.6 mL, 11 mmole) were dissolved in toluene (5 mL) and heated at 110°C for 24 hours. The reaction mixture was cooled and treated with water and ether. After extraction of the aqueous phase with ether, the combined organic phases were dried (MgSO 4 ), concentrated, and chromatographed on silica gel with 10% ethyl acetate/ hexane. The resultant product was a waxy solid (1.9 g, 82% yield).
  • Step D 6-ethyl-4-[[1-[4-(trimethylsilyl)phenyl]-ethyl]amino]-5-pyrimidinecarbonitrile
  • Step D ⁇ -methyl-4-trimethylsilylbenzenemethanamine The product of Step C (91 g, 0.28 mole) and
  • Step E 6-ethyl-N-[1-[4-(trimethylsilyl)phenyl]ethyl]-4-pyrimidinamine
  • 6-ethyl-4-pyrimidinol (1.0 g, 8.5 mmole) was dissolved in 10 mL of tetramethylene sulfone by warming to 30°C. Nitronium tetrafluoroborate (2.5 g, 19 mmole) was added portionwise and the reaction mixture was heated at 60°C for one hour. The reaction was cooled, poured into ice water, and extracted several times with ethyl acetate. The combined organic phases were washed two times with water, dried (MgSO 4 ), concentrated, and chromatographed on silica gel with 10% methanol/ chloroform. The product was an orange solid (0.85 g, 59% yield).
  • Step B 4-chloro-6-ethyl-5-nitropyrimidine
  • Step A The product of Step A (0.85 g, 5.0 mmole) was combined with phosphorus oxychloride (10 mL) and heated at 100°C for one hour, during which the slurry became homogeneous. The mixture was concentrated under vacuum and the residue was added to ice. Concentrated NH 4 OH solution was carefully added until the aqueous phase was basic. This solution was extracted several times with ether and the combined organic phases were dried (MgSO 4 ) and concentrated to give a waxy solid product (0.64 g, 68% yield).
  • Step C 6-ethyl-5-nitro-N-[1-[4-(trimethylsilyl)-phenyl]-ethyl]-4-pyrimidinamine
  • Tables 1 to 4 can be prepared.
  • the compounds in Table 1, line 1 can be referred to as 1-1, 1-2, 1-3, 1-4 and 1-5 (as designated by line and column). All the other specific compounds covered in these Tables can be designated in an analogous fashion relying on the Table number to help distinguish between compounds 1-1 of Table 1 and 1-1 of Table 2, etc.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Useful formulations can be prepared in conventional ways. They include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like. 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.
  • formulations will typically contain effective amounts of an active ingredient, diluent and a surfactant within the following approximate ranges wherein the active ingredient plus surfactant and/or diluent equals 100 weight percent.
  • compositions Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and
  • All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
  • Solutions are prepared by simply mixing the ingredients. 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.
  • the ingredients are blended and ground in a hammer mill to produce a high strength concentrate
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
  • the ingredients are thoroughly blended.
  • the liquid surfactant is added by spraying upon the solid
  • Compound 1 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No.
  • the active ingredient is dissolved in a volatile solvent such as acetone and sprayed upon dedusted and pre-warmed attapulgite granules in a double cone blender.
  • a volatile solvent such as acetone
  • the acetone is then driven off by heating , and the granules are allowed to cool.
  • Compound 1 25.0% hydrated attapulgite 3.0% crude calcium ligninsulfonate 10.0% sodium dihydrogen phosphate 0.5% water 61.5% The ingredients are ground together in a ball mill or roller mill until the solid particles have been reduced to diameters under 10 microns.
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
  • the ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These can be used directly after drying, or the dried pellets can be crushed to pass a U.S.S. No. 20 sieve (0.84 mm
  • the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) can be used and the fines recycled.
  • Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%
  • the ingredients are combined and stirred with gentle warming to speed solution.
  • a fine screen filter is included in packaging operation to insure the absence of extraneous undissolved material in the product.
  • Wettable powder of Example B 10.0% pyrophyllite (powder) 90.0%
  • the wettable powder and the pyrophyllite diluent are thoroughly blended.
  • the compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health.
  • arthropods term includes insects, mites and nematodes
  • Those skilled in the art will appreciate that not all compounds are equally effective against all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the
  • Order Lepidoptera eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and
  • the compounds of this invention are also active against pests of the Orders Hymenoptera,
  • the compounds of this invention are also useful as plant disease control agents. They provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete and Oomycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar
  • pathogens of ornamental, vegetable, field, cereal, and fruit crops include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Rhizoctinia Solani, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera
  • the compounds of this invention also control seed pathogens.
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides,
  • insecticides such as monocrotophos, carbofuran, avermectin B, tetrachlor-vinphos, malathion, parathion-methyl, methomyl, chlor- dimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fonophos, isofenphos, methidathion, metha-midophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor,
  • fungicides such as carbendazim, thiuram, dodine, maneb, chloroneb, benomyl, cymoxanil,
  • bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite and fenbutatin oxide; and biological agents such as Bacillus thuringiensis, and baculovirus.
  • Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the compounds of this
  • a preferred method of application is by spraying with equipment that distributes the compound in the
  • granular formulations of these compounds can be applied to the foliage or applied to or
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like which entice them to ingest or otherwise contact the compounds.
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the 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.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • suitable carriers diluents, and surfactants
  • the rate of application required for effective control arthropod will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. In general, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to provide large-scale effective control of pests in agronomic ecosystems under normal circumstances, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectare may be required. For nonagronomic
  • 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • Rates of application for these compounds as plant disease control agents 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 10,000 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.
  • test compounds were 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 (polyhydric alcohol esters). This 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 growth chamber at 20°C for 7 days, after which disease ratings were made. Of the compounds tested, the following gave 70% disease control or higher: 1, 2, 3, 4, 5, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18.
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then
  • test compounds were 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 (polyhydric alcohol esters). This suspension is sprayed to the point of run-off on rice seedlings. The following day the seedlings are 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 are made. Of. the compounds tested, the following gave 70% disease control or higher: 1, 2, 7, 18.
  • kidney bean leaves that have been infested on the undersides with 25 to 30 adult mites ( Tetranychus urticae) were sprayed with their undersides facing up on a hydraulic sprayer.
  • the leaf-squares were placed underside up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites cannot escape onto untreated leaf surface.
  • the test units were held at 27°C and 50% relative humidity for 48 hrs., after which time

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Cette invention concerne des aminopyrimidines qui se caractérisent par diverses substitutions en position 5 du cycle de pyrimidine ainsi que des compositions pour l'agriculture les contenant, lesquelles sont utilisées pour éliminer et réguler les arthropodes dans des environnements agricoles et non agricoles.
PCT/US1993/002757 1992-04-24 1993-03-22 Aminopyrimidines arthropidicides et fongicides WO1993022291A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US87346992A 1992-04-24 1992-04-24
US07/873,469 1992-04-24
US93614592A 1992-08-26 1992-08-26
US07/936,145 1992-08-26

Publications (1)

Publication Number Publication Date
WO1993022291A1 true WO1993022291A1 (fr) 1993-11-11

Family

ID=27128300

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/002757 WO1993022291A1 (fr) 1992-04-24 1993-03-22 Aminopyrimidines arthropidicides et fongicides

Country Status (2)

Country Link
AU (1) AU3933493A (fr)
WO (1) WO1993022291A1 (fr)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0665225A1 (fr) * 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phénylaminopyrimidines, procédé pour leur préparation et pesticides pour l'agriculture et l'horticulture les contenant
US5439911A (en) * 1992-12-28 1995-08-08 Shionogi & Co., Ltd. Aminopyrimidine derivatives and their production and use
WO1998007421A1 (fr) * 1996-08-16 1998-02-26 Ishihara Sangyo Kaisha, Ltd. Composition medicinale
US5852023A (en) * 1995-03-29 1998-12-22 Hoechst Schering Agrevo Gmbh Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides
WO2012096061A1 (fr) * 2011-01-14 2012-07-19 株式会社エス・ディー・エス バイオテック Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole
US20140057912A1 (en) * 2011-03-25 2014-02-27 Incyte Corporation Pyrimidine-4,6-diamine derivatives as pi3k inhibitors
CN104292169A (zh) * 2013-07-19 2015-01-21 中国中化股份有限公司 取代的嘧啶胺类化合物及其用途
US9108984B2 (en) 2011-03-14 2015-08-18 Incyte Corporation Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors
US9193721B2 (en) 2010-04-14 2015-11-24 Incyte Holdings Corporation Fused derivatives as PI3Kδ inhibitors
US9199982B2 (en) 2011-09-02 2015-12-01 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US9296701B2 (en) 2012-04-24 2016-03-29 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9309251B2 (en) 2012-04-02 2016-04-12 Incyte Holdings Corporation Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US9340557B2 (en) 2013-03-12 2016-05-17 Vertex Pharmaceuticals Incorporated Substituted quinoxaline DNA-PK inhibitors
US9403847B2 (en) 2009-12-18 2016-08-02 Incyte Holdings Corporation Substituted heteroaryl fused derivatives as P13K inhibitors
US9434746B2 (en) 2009-06-29 2016-09-06 Incyte Corporation Pyrimidinones as PI3K inhibitors
US9527848B2 (en) 2010-12-20 2016-12-27 Incyte Holdings Corporation N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
US9732097B2 (en) 2015-05-11 2017-08-15 Incyte Corporation Process for the synthesis of a phosphoinositide 3-kinase inhibitor
US9988401B2 (en) 2015-05-11 2018-06-05 Incyte Corporation Crystalline forms of a PI3K inhibitor
US10039761B2 (en) 2013-10-17 2018-08-07 Vertex Pharmaceuticals Incorporated Co-crystals and pharmaceutical compositions comprising the same
US10077277B2 (en) 2014-06-11 2018-09-18 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10336759B2 (en) 2015-02-27 2019-07-02 Incyte Corporation Salts and processes of preparing a PI3K inhibitor
US11110108B2 (en) 2016-09-27 2021-09-07 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA-damaging agents and DNA-PK inhibitors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0264217A2 (fr) * 1986-10-08 1988-04-20 Ube Industries, Ltd. Dérivés d'aralkylaminopyrimidine, procédé pour leur préparation et insecticides, acaricides et fongicides contenant ces composés comme ingredients actifs
EP0370704A2 (fr) * 1988-11-21 1990-05-30 Ube Industries, Ltd. Dérivés d'aralkylamine, leur préparation et fungicides les contenant
EP0424125A2 (fr) * 1989-10-18 1991-04-24 Ube Industries, Ltd. Dérivés d'aralkylamine, leur méthode de préparation et fongicides les contenant
EP0519211A1 (fr) * 1991-05-17 1992-12-23 Hoechst Schering AgrEvo GmbH 4-Aminopyrimidines substituées, procédé pour leur préparation et leur utilisation comme parasiticide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0264217A2 (fr) * 1986-10-08 1988-04-20 Ube Industries, Ltd. Dérivés d'aralkylaminopyrimidine, procédé pour leur préparation et insecticides, acaricides et fongicides contenant ces composés comme ingredients actifs
EP0370704A2 (fr) * 1988-11-21 1990-05-30 Ube Industries, Ltd. Dérivés d'aralkylamine, leur préparation et fungicides les contenant
EP0424125A2 (fr) * 1989-10-18 1991-04-24 Ube Industries, Ltd. Dérivés d'aralkylamine, leur méthode de préparation et fongicides les contenant
EP0519211A1 (fr) * 1991-05-17 1992-12-23 Hoechst Schering AgrEvo GmbH 4-Aminopyrimidines substituées, procédé pour leur préparation et leur utilisation comme parasiticide

Cited By (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5439911A (en) * 1992-12-28 1995-08-08 Shionogi & Co., Ltd. Aminopyrimidine derivatives and their production and use
US5519139A (en) * 1992-12-28 1996-05-21 Shionogi & Co., Ltd. Aminopyrimidine derivatives and their production and use
EP0665225A1 (fr) * 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phénylaminopyrimidines, procédé pour leur préparation et pesticides pour l'agriculture et l'horticulture les contenant
US5852023A (en) * 1995-03-29 1998-12-22 Hoechst Schering Agrevo Gmbh Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides
WO1998007421A1 (fr) * 1996-08-16 1998-02-26 Ishihara Sangyo Kaisha, Ltd. Composition medicinale
US6429212B1 (en) * 1996-08-16 2002-08-06 Ishihara Sangyo Kaisha Ltd. Medicinal composition
US6515129B1 (en) 1996-08-16 2003-02-04 Ishihara Sangyo Kaisha Ltd. Pharmaceutical composition
US9975907B2 (en) 2009-06-29 2018-05-22 Incyte Holdings Corporation Pyrimidinones as PI3K inhibitors
US10428087B2 (en) 2009-06-29 2019-10-01 Incyte Corporation Pyrimidinones as PI3K inhibitors
US9434746B2 (en) 2009-06-29 2016-09-06 Incyte Corporation Pyrimidinones as PI3K inhibitors
US10829502B2 (en) 2009-06-29 2020-11-10 Incyte Corporation Pyrimidinones as PI3K inhibitors
US11401280B2 (en) 2009-06-29 2022-08-02 Incyte Holdings Corporation Pyrimidinones as PI3K inhibitors
US9403847B2 (en) 2009-12-18 2016-08-02 Incyte Holdings Corporation Substituted heteroaryl fused derivatives as P13K inhibitors
US9193721B2 (en) 2010-04-14 2015-11-24 Incyte Holdings Corporation Fused derivatives as PI3Kδ inhibitors
US9815839B2 (en) 2010-12-20 2017-11-14 Incyte Corporation N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
US9527848B2 (en) 2010-12-20 2016-12-27 Incyte Holdings Corporation N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
JP2012148981A (ja) * 2011-01-14 2012-08-09 Sds Biotech Corp 農園芸用の有害生物防除剤としてのピリミジン誘導体
WO2012096061A1 (fr) * 2011-01-14 2012-07-19 株式会社エス・ディー・エス バイオテック Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole
US9108984B2 (en) 2011-03-14 2015-08-18 Incyte Corporation Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors
US9126948B2 (en) * 2011-03-25 2015-09-08 Incyte Holdings Corporation Pyrimidine-4,6-diamine derivatives as PI3K inhibitors
US20140057912A1 (en) * 2011-03-25 2014-02-27 Incyte Corporation Pyrimidine-4,6-diamine derivatives as pi3k inhibitors
US9707233B2 (en) 2011-09-02 2017-07-18 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US10646492B2 (en) 2011-09-02 2020-05-12 Incyte Corporation Heterocyclylamines as PI3K inhibitors
US10092570B2 (en) 2011-09-02 2018-10-09 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US9730939B2 (en) 2011-09-02 2017-08-15 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US11433071B2 (en) 2011-09-02 2022-09-06 Incyte Corporation Heterocyclylamines as PI3K inhibitors
US9199982B2 (en) 2011-09-02 2015-12-01 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US10376513B2 (en) 2011-09-02 2019-08-13 Incyte Holdings Corporation Heterocyclylamines as PI3K inhibitors
US11819505B2 (en) 2011-09-02 2023-11-21 Incyte Corporation Heterocyclylamines as PI3K inhibitors
US9309251B2 (en) 2012-04-02 2016-04-12 Incyte Holdings Corporation Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US10259818B2 (en) 2012-04-02 2019-04-16 Incyte Corporation Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US9944646B2 (en) 2012-04-02 2018-04-17 Incyte Holdings Corporation Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US10501439B2 (en) 2012-04-24 2019-12-10 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US10391095B2 (en) 2012-04-24 2019-08-27 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9376448B2 (en) 2012-04-24 2016-06-28 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9592232B2 (en) 2012-04-24 2017-03-14 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US10076521B2 (en) 2012-04-24 2018-09-18 Vertex Pharamceuticals Incorporated DNA-PK inhibitors
US11021465B2 (en) 2012-04-24 2021-06-01 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9296701B2 (en) 2012-04-24 2016-03-29 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9925188B2 (en) 2012-04-24 2018-03-27 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors and uses thereof
US10442791B2 (en) 2012-04-24 2019-10-15 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US11008305B2 (en) 2012-04-24 2021-05-18 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9878993B2 (en) 2012-04-24 2018-01-30 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors for treatment of cancer
US9340557B2 (en) 2013-03-12 2016-05-17 Vertex Pharmaceuticals Incorporated Substituted quinoxaline DNA-PK inhibitors
US9987284B2 (en) 2013-03-12 2018-06-05 Vertex Pharmaceuticals Incorporated Substituted benzooxadiazole DNA-PK inhibitors
US10258627B2 (en) 2013-03-12 2019-04-16 Vertex Pharmaceutical Incorporated DNA-PK inhibitors
US11813267B2 (en) 2013-03-12 2023-11-14 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US10786512B2 (en) 2013-03-12 2020-09-29 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US9359380B2 (en) 2013-03-12 2016-06-07 Vertex Pharmaceuticals Incorporated DNA-PK inhibitors
US10973830B2 (en) 2013-03-12 2021-04-13 Vertex Pharmaceuticals Incorporated Substituted quinoxaline DNA-PK inhibitors
CN104292169A (zh) * 2013-07-19 2015-01-21 中国中化股份有限公司 取代的嘧啶胺类化合物及其用途
US10039761B2 (en) 2013-10-17 2018-08-07 Vertex Pharmaceuticals Incorporated Co-crystals and pharmaceutical compositions comprising the same
US10716789B2 (en) 2013-10-17 2020-07-21 Vertex Pharmaceuticals Incorporated Co-crystals and pharmaceutical compositions comprising the same
US11130767B2 (en) 2014-06-11 2021-09-28 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10479803B2 (en) 2014-06-11 2019-11-19 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10077277B2 (en) 2014-06-11 2018-09-18 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US11999751B2 (en) 2014-06-11 2024-06-04 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US11084822B2 (en) 2015-02-27 2021-08-10 Incyte Corporation Salts and processes of preparing a PI3K inhibitor
US10336759B2 (en) 2015-02-27 2019-07-02 Incyte Corporation Salts and processes of preparing a PI3K inhibitor
US12024522B2 (en) 2015-02-27 2024-07-02 Incyte Corporation Salts and processes of preparing a PI3K inhibitor
US9732097B2 (en) 2015-05-11 2017-08-15 Incyte Corporation Process for the synthesis of a phosphoinositide 3-kinase inhibitor
US10125150B2 (en) 2015-05-11 2018-11-13 Incyte Corporation Crystalline forms of a PI3K inhibitor
US9988401B2 (en) 2015-05-11 2018-06-05 Incyte Corporation Crystalline forms of a PI3K inhibitor
US11110108B2 (en) 2016-09-27 2021-09-07 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA-damaging agents and DNA-PK inhibitors
US11980633B2 (en) 2016-09-27 2024-05-14 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA-damaging agents and DNA-PK inhibitors

Also Published As

Publication number Publication date
AU3933493A (en) 1993-11-29

Similar Documents

Publication Publication Date Title
WO1993022291A1 (fr) Aminopyrimidines arthropidicides et fongicides
AU658159B2 (en) Insecticidal, acaricidal and fungicidal aminopyrimidines
WO1995007278A1 (fr) Aminopyrimidines fongicides, acaricides et arthropodicides
JP3597194B2 (ja) 殺節足動物性オキサゾリン類およびチアゾリン類
WO1995003306A1 (fr) Heterocycles azacycliques arthropodicides
WO1999031072A1 (fr) Arthropodicides et fongicides de cyclohexylamine
US5728693A (en) Arthropodicidal oxadiazine-thiadiazine-or triazine-carboxanilides
US5328915A (en) Arthropodicidal amidrazone ureas
EP0632803B1 (fr) Amides arthropodicides
WO1997011057A1 (fr) 1,4-dihydropyridines et 1,4-dihydropyrimidines arthropodicides
EP0869963A1 (fr) Organosilanes et organogermanes arthropodicides et fongicides
WO1995019972A1 (fr) 2-oxa et thia-zolines arthropodicides
WO1994008976A1 (fr) Aminopyrimidines fongicides et acaricides
EP0636121A1 (fr) Sulfonates de pyrazole arthropodicides
US5444079A (en) Arthropodicidal oxazolines
AU3058492A (en) Arthropodicidal and nematicidal sulfonates
EP0533734A1 (fr) Iminooxazolidinones fongicides
WO1995016676A1 (fr) Anilides arthropodicides a substitution pentafluorothio
WO1993022289A1 (fr) Imidazolidines agissant contre les arthropodes
US5514678A (en) Arthropodicidal 1,2,4-triazinyl amides
WO1993021150A2 (fr) Arlylsulfonates arthropodicides
WO1993021161A1 (fr) Nitroguanidines et nitroethylenes arthropodicides
WO1995000491A1 (fr) Sulfonates arthropodicides
EP0629201A1 (fr) Amides utilises pour la lutte contre les arthropodes
WO1996033180A1 (fr) Arthropodicides d'oxazoline et de thiazoline

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR JP NZ US

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

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
122 Ep: pct application non-entry in european phase