WO1998012184A1 - Composes de pyrimidine, procede de preparation correspondant et agents de lutte antiparasitaire - Google Patents

Composes de pyrimidine, procede de preparation correspondant et agents de lutte antiparasitaire Download PDF

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Publication number
WO1998012184A1
WO1998012184A1 PCT/JP1997/003292 JP9703292W WO9812184A1 WO 1998012184 A1 WO1998012184 A1 WO 1998012184A1 JP 9703292 W JP9703292 W JP 9703292W WO 9812184 A1 WO9812184 A1 WO 9812184A1
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Prior art keywords
group
formula
alkyl
compound
represent
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PCT/JP1997/003292
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English (en)
Japanese (ja)
Inventor
Isami Hamamoto
Keiichi Ishimitsu
Yoichi Ihori
Hidemitsu Takahashi
Takehiko Nakamura
Takao Iwasa
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Nippon Soda Co., Ltd.
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Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU42217/97A priority Critical patent/AU4221797A/en
Publication of WO1998012184A1 publication Critical patent/WO1998012184A1/fr

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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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a compound having a novel pyrimidine skeleton and a pesticidal composition containing the compound as an active ingredient.
  • ⁇ 1 ⁇ ! ⁇ 1 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, X ', X 2 represents an oxygen atom, a sulfur atom, N r simultaneously' One represents a 3, etc.
  • An object of the present invention is to provide a novel pesticidal agent which has a certain effect and can be used safely.
  • R ′, R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R ′. , Scale '' and 1 ⁇ are each independently a hydrogen atom, a halogen atom, C -s alkyl group, Haroa alkyl group, C!
  • R e and R 7 each independently represent a hydrogen atom, a halogen atom, an alkyl group or a C i -S haloalkyl group,
  • R 13 represents a hydrogen atom, a (halogen atom, a C, —B alkoxy group, a cyano group, a tri C
  • Arukirushi Li group an alkylcarbonyl group, C, - S alkoxycarbonyl group, Te preparative La arsenide Dorofuraniru group, is also rather substituted with a conversion which may be full We two Le group) which may C,-beta alkyl group, but it may also be substituted by a halogen atom c 2 - 8 alkenyl group, C 2 -B alkynyl group, and C e alkyl group, even mono optionally substituted phenylpropyl group Or a disubstituted radical group, COR 11 (R M is an alkyl group, a C 3 -s cycloalkyl group, a C,- «alkoxy group,
  • the present invention relates to a compound having a pyrimidine skeleton represented by a pre-empirical formula [II], and an insecticide and acaricide containing the compound as an active ingredient.
  • R u ⁇ beauty R 12 are each independently a hydrogen atom, full Tsu containing chlorine , Bromine and other halogen atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, etc., C1 alkyl groups, trifluoromethyl groups, etc.
  • C 6 Alkyl groups Cs alkoxy groups such as methoxy, ethoxy, n-propoxy, and isopropoxy groups
  • Cis alkylthio groups such as methylthio, ethylthio, propylthio, and isopropylthio groups
  • C such as butoxy group, Bruno, mouth alkoxy group, a Mi amino group, two collected by filtration group, Shiano group, main Chirusuruhoniru, Echirusuruhoniru, n -.
  • a methoxy group such as a ethoxy group or the like, a methoxy group, a nitro group or the like; a phenyl group; Halogen atom such as bromine, C, -B alkyl group such as methyl and ethyl, methoxy.
  • Ethoxy group, etc. may be substituted with 6- alkoxy group, nitro group, etc.) 2 — pyri Ziloxy group, (Hydroxy, chlorine, bromine, etc.
  • Emissions atoms, methylation, alkyl groups such as Echiru, main butoxy, 6 alkoxy group such as e butoxy group, may be substituted with two collected by filtration group) 3 - pyridyl Jiruokishi group, arbitrary in (pyridinium Jin ring Substituted with a halogen atom such as fluorine, chlorine, odor purple, etc., a C, -s alkyl group such as methyl and ethyl, a methoxy group, an ethoxy group, etc. An alkoxy group, a nitrogen group, etc.
  • R 'and R 2 also rather is R 2 and R 3 since it conversion is good main switch which may have been down Jiokishi group or Te preparative la together It may form a hydrofuranyl ring.
  • R e, R 7 are each independently a hydrogen atom, full Tsu-containing, chlorine, Ha androgenic atom such as a bromine atom, methylation, Echiru, C etc.
  • propyl Lee Sopuro propyl group, -. 6 alkyl group, Or represents a 6 haloalkyl group such as a trifluoromethyl group
  • R '3 represents a hydrogen atom, methylation, Echiru propyl, i Sopuro pills, heptyl, t -.. Heptyl, pentyl, hexyl, Application Benefits Furuoro methylation main Bok carboxymethyl methylation, main butoxy Echiru, main Tokishipuro pill Methoxybutyl, ethoxymethyl.
  • P-chloro C-alkyl which may have a substituent such as benzyl, vinyl, arylalkyl.
  • 4-difluoro-2, 3 - Bed evening may be substitution with a halogen atom such as a Jeniru C 2 - 6 alkenyl group, E Ji Le, C 2, such propargyl group -.
  • R 4 , R 5 .R 9 and R 12 represent a hydrogen atom
  • R′.R 2 , R 3 , R 8 , R′o and R 11 each independently represent a water purple atom And a halogen atom.
  • Compounds having a C haloalkyl group, a ⁇ - haloalkoxy group, a cyano group, or a nitro group have particularly excellent insecticidal activity as compared with the compound described in WO94 / 02470. Show.
  • the compound of the present invention can be produced, for example, as follows. Manufacturing method 1
  • R ′, R 2 , R 3 , R 1 , R 5 , R 6 , R 7 , R s , R ′, R ′., R 1 R ′ 3 have the same meanings as described above. Represents.
  • a dihalogenobilimidine such as dichloropyrimidine represented by the formula [II] is added to the formula [II! Is reacted in the presence of a base to obtain an intermediate (IV), and then the aniline represented by the formula (V) is reacted in the presence of a base. It is what makes them.
  • Palladium catalysts that can be used in this reaction include palladium chloride, bis (triphenylphosphine) dichloroharadium, and tetrakis (triphenyl). Phosphine) palladium, tris (dibenzylideneacetate) diparadium.chloroform adducts, and the like.
  • the amount of the catalyst is preferably from 1 mol% to 20 mol% with respect to 1 mol of the halogeno pyrimidine represented by the formula [IV]:
  • the triflic acid is preferably used.
  • Production method 3 in which the reaction can be carried out in the co-presence of a phosphorus compound such as triaryl phosphine such as enyl phosphine or tritril phosphine.
  • the compound of the present invention can also be produced by the following method.
  • R 1 , R 2 , R 3 , R 4 , R 5 RR 7 , RRRRR 12 and R 13 represent the same meaning as described above.
  • an aniline represented by the formula (V) is allowed to act on a dihalogeno pyrimidine such as a dicyclopyrimidine represented by the formula (II) in the presence of a base to form an intermediate (V).
  • a dihalogeno pyrimidine such as a dicyclopyrimidine represented by the formula (II)
  • the funinols represented by the formula [111] are reacted in the presence of a base.
  • R 13 is a group other than a hydrogen atom
  • R 13 is a group other than a hydrogen atom
  • R 1 2 are the same as defined above, R '3' is the table as defined above R 1 3 except hydrogen atom, X represents a leaving group.
  • the compound represented by the formula [I-11] can be produced by reacting a compound represented by the formula [I-11] with a compound represented by the formula [VI] in the presence or absence of a base.
  • a compound represented by the formula [ ⁇ ] include, for example, halogenated alkyls such as methyl iodide, isopropyl iodide, isopropyl bromide, and aryl chloride; and dialkyl sulfates such as dimethyl sulfate.
  • esters alkyl sulfonic acid esters such as propyl tosylate and butyl methyl sulphate; phosphoric acid esters such as trimethyl phosphite; ortho esters such as ethyl ethyl formate; dimethylformyl Alkylating agents such as formamide salts such as amide dimethyl acetal, etc., onium salts such as diazomethane and dimethyloxosulfonium salt,
  • Carboxylic acid derivatives such as acetyl chloride, acetic anhydride, formic acid, and methyl acetate; dimethylation; acylation agents such as potassium rubavamoyl chloride; and acylation agents such as haematogen compounds such as methansulfinyl chloride; Nilchloride, methane sulfone Sulfonylating agents such as sulfur halides such as chlorochloride; sulfinylating agents; sulfenylating agents; and the like. Further, the sulfinyl-sulfonylation can also be produced by sequentially oxidizing the corresponding sulfinyl compound with an oxidizing agent.
  • Bases that can be used in the reactions of these production methods i to 4 are, for example, triethylamine, diisopropylethylamine, pyridine, and 1,8-diazabicyclo. -[5,4.0]-7- ⁇ decane (DBU), carbonates such as potassium carbonate and sodium carbonate, hydroxides such as sodium hydroxide and potassium hydroxide, and water Hydrides such as sodium hydride, sodium methoxide ', metal alkoxides such as sodium ethoxide, and calcium-t-butoxide.
  • DBU decane
  • carbonates such as potassium carbonate and sodium carbonate
  • hydroxides such as sodium hydroxide and potassium hydroxide
  • water Hydrides such as sodium hydride, sodium methoxide ', metal alkoxides such as sodium ethoxide, and calcium-t-butoxide.
  • Solvents that can be used in these reactions include N, N : —dimethylformamide (DMF), N, N—dimethylacetamide (DMA), N— Pads such as methylpyrrolidone, ethers such as tetrahydrofuran (THF), and ethyl ether, alcohols such as methanol and ethanol, benzene, toluene, and xylene Examples thereof include aromatic hydrocarbons such as butane, esters such as ethyl acetate, nitriles such as acetonitril, dimethyl sulfoxide (DMSO), and the like. These reactions proceed smoothly within the temperature range of the boiling point of the solvent used after zero. In any of the reactions, after completion of the reaction, the desired product can be obtained by performing post-operations by a usual synthetic chemistry technique.
  • DMF dimethylformamide
  • DMA dimethylacetamide
  • Pads such as methylpyrrolidone, ethers such as t
  • the structure of the reaction product was identified by measuring various spectra such as NMR, 1R, and MASS.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an insecticidal, nymphalidic, larvicidal, and ovicidal action.
  • the following are typical examples.
  • Lepidopteran pests for example, scutellaria spp. , Kinmonhosoga, Myimaga, Jiyadokuga, Nikkameiga, Kobunomeiga, Yoichichi Biancon Borra-, Americana Horitori, Sujimadara Mega, Heliotisu, Helicobelpa, Aggrotis II, Iga, Kodlinga, Ichimami Mimi, etc.
  • Hemiptera pests for example, peach aphid, petal aphid, Nisedai kombi, wheat bilea aphid, scorpion worm, mosquito mosquito, yano okaigamurashi, kukonakaigaramushi, konshika nagamurashibushi, shikomi shikoku , Tobi-iron power, Hime-to-bin power, Sedge lownka, Tsumagurokonokoi, etc.
  • Coleopteran pests for example, Leaf beetle, Leaf beetle, Colorado beetle, Rice mud beetle, Red beetle, Azuki beetle, Bean beetle, Brown beetle, Japrotica genus, Evening beetle, Leaf beetle Mikiri, sesame power, agriculture, nervous system, coconut, pork, etc.
  • Nuptera pests for example, house flies, oak fly, sentinella flies, flies, flies, rice flies, rice flies, flies, flies, flies, flies The power of swords, the power of shinahamadara, etc.
  • Orthoptera pests for example, southern blue thistle, cyano thistle, etc., Lepidopteran insects, for example, blue ants, hornets, wasps, etc., orthopterous insects, for example, japonicus Panic cockroaches, red cockroaches, black cockroaches, black cockroaches, etc.
  • Pests of the order Isoptera for example, Yeshiroa, Yamatoshiro
  • Laminariae pests for example, human fleas, lice Pests, for example, human louse, etc.
  • Mites for example, Namihadani, Kanzahadaji, Micani spider mite, Lingo spider mite, Mikansabida (2) Lingo Savidani, Chino Hoko Ridani, Blevi Palpa ⁇ , Je te Tranikas, Kobinedani, Kenagakonadani, Konahi-y ⁇ mikomi, Oshishima mite, Scarabidae, etc.
  • Plant-parasitic nematodes such as sweet potato nematode, nexarecenti, soybean ciscentium, rice singarecenti, matsunosaisenyu and the like.
  • the compound of the present invention has an excellent insecticidal and acaricidal effect against not only susceptible strains but also insect pests of organic phosphorus, carbamate or pyrethide-resistant strains and mites of acaricide-resistant strains. It is a drug.
  • the compound of the present invention is a highly safe drug with low phytotoxicity, low toxicity to fish poisons and mixed animals.
  • the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets.
  • the compound of the present invention when applied as an insecticide or acaricide, it can be used in a pure form without adding other components, and it can be used in general agricultural chemicals for use as a broad medicine. That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, powders, flowables and the like.
  • solid additives are used as additives and carriers, soybean grains, vegetable powders such as flour, diatomaceous earth, limestone, gypsum, talc, bentonite, pyrophyllite, clay And organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol , Acetone, trichloroethylene, methyl isoptyl ketone, mineral oil, vegetable oil, water, etc. are used as solvents.
  • a surfactant can be added if necessary.
  • the amount of the active ingredient is preferably 5 to 70%.
  • the wettable powder, emulsion and flowable obtained in this manner are diluted with water at a predetermined temperature to prepare a suspension or emulsion, and the powder and granules are sprayed as they are. Is done.
  • the compound of the present invention is sufficiently effective alone, but it can also be used in combination with one or more of various fungicides, insecticides, acaricides, or synergists. .
  • fungicides insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Captan Forpet, Thiuram, Jiram, Zineb, Maneb, Mancozeb, Provineb, Polycarbamate, Chlorotalonil, Quintzensen, Capita Hor, iplodione, procymidone, vinclozolin, fluorimide, thymoxanil, mepronil, furtranil, penciclone, oxycarboxynin, josetyl aluminum, propamocarb, triadimene Phone, Triadimenol, Propiconabul, Diclobtrazol, Bitertanol, Hexaconazole, Microcrobyl, Flusilazole, Ethaconazole, Fluotrimazole, Full Triafene, benconazole, diconazole, cyproconazoles, fenarymol, triflumisol, prochloraz, imazalil, perfrazoate, tridemorph, fenpropimorph, trifoli
  • Plant growth regulator Plant growth regulator
  • Haruto's 41-fluoro-3-trifluoromethyl was synthesized as follows.
  • the 4-fluoro-3-trifluoromethyl phenol can also be obtained by the method described in Japanese Unexamined Patent Publication No. 1-268685.
  • Table 1 summarizes the compounds of the present invention that can be produced as described above.
  • the above ingredients are mixed and wet-pulverized until the abundance is 1 micron or less, whereby a suspension of 103 ⁇ 4 of the active ingredient is obtained.
  • the acaricidal effectiveness was calculated by the following formula.
  • Example 7 According to the formulation of the wettable powder described in Example 7 of the above-mentioned drug, it was diluted with water so that the compound concentration was 125 ppm. Corn leaves were immersed in the chemical solution for 30 seconds and air-dried, and then the leaves were placed in a scale containing five second instar larvae. They were placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65% with a glass lid, and the insecticidal rate was examined 6 days later. The results are summarized in Table 2. Younger brother
  • Example 7 According to the formula of wettable powder shown in Example 7 of the above-mentioned drug, it was diluted with water so that the compound concentration became 31 pm.
  • the cabbage leaves were soaked in the chemical for 30 seconds, air-dried, and then put into a petri dish containing five tomato larvae: 5 caps, a glass lid, a temperature of 25, and a humidity of 6 5 % In a constant temperature room, and 3 Two reactions.
  • the results are summarized in Table 3.
  • the compound represented by the formula [I] has an excellent insecticidal and acaricidal effect, and the composition containing the compound of the present invention is useful as an insecticide and acaricide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Cette invention concerne de nouveaux composés de pyrimidine représentés par la formule générale (I) ainsi que des agents de lutte antiparasitaire contenant lesdits composés en tant qu'ingrédient actif. Dans la formule (I), R?1, R2, R3, R4, R5, R8, R9, R10, R11 et R12¿ sont chacun indépendamment hydrogène, halogéno, alkyle C¿1?-C6, haloalkyle C1-C6, alcoxy C1-C6, alkylthio C1-C6, haloalcoxy C1-C6 ou analogue; R?6 et R7¿ sont chacun indépendamment hydrogène, halogéno, alkyle C¿1?-C6 ou haloalkyle C1-C6; et R?13¿ est hydrogène, alkyle C¿1?-C6 éventuellement substitué, alkényle C2-C6 éventuellement substitué, alkynyle C2-C6, carbamoyle éventuellement substitué, COR?14 (où R14¿ est alkyle C¿1?-C6, cycloalkyle C3-C6, alcoxy C1-C6 ou analogue) ou SOnR?15 (où R15¿ est alkyle C¿1?-C6, alkényle C2-C6, alkynyle C2-C6 ou di(alkyle C1-C6)amino; et n est égal à 0, 1 ou 2).
PCT/JP1997/003292 1996-09-19 1997-09-18 Composes de pyrimidine, procede de preparation correspondant et agents de lutte antiparasitaire WO1998012184A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU42217/97A AU4221797A (en) 1996-09-19 1997-09-18 Pyrimidine compounds, process for the preparation thereof, and pest controlling agents

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP8/269309 1996-09-19
JP26930996 1996-09-19
JP35686796 1996-12-26
JP8/356867 1996-12-26

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000080084A (ja) * 1998-07-14 2000-03-21 American Cyanamid Co 殺ダニ性並びに殺虫性の置換ピリミジン類及びその製造方法
WO2000049001A2 (fr) * 1999-02-16 2000-08-24 E.I. Du Pont De Nemours And Company Phenoxypyrimidines insecticides et acaricides
WO2000071536A1 (fr) * 1999-05-20 2000-11-30 E.I. Du Pont De Nemours And Company Heteroaryloxypyrimidine insecticides et acaricides
US6281219B1 (en) 1998-07-14 2001-08-28 American Cyanamid Co. Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof
US6342499B1 (en) 1998-07-14 2002-01-29 Basf Aktiengesellschaft Parasitic and saprophagous mite control in beneficial insects
EP2222162A2 (fr) * 2007-11-28 2010-09-01 Dana Farber Cancer Institute Inhibiteurs myristate à petites molécules de bcr-abl et procédés d'utilisation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05163249A (ja) * 1990-07-27 1993-06-29 Imperial Chem Ind Plc <Ici> 殺菌性化合物、その製造方法及びそれを含有する殺菌剤組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05163249A (ja) * 1990-07-27 1993-06-29 Imperial Chem Ind Plc <Ici> 殺菌性化合物、その製造方法及びそれを含有する殺菌剤組成物

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000080084A (ja) * 1998-07-14 2000-03-21 American Cyanamid Co 殺ダニ性並びに殺虫性の置換ピリミジン類及びその製造方法
US6281219B1 (en) 1998-07-14 2001-08-28 American Cyanamid Co. Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof
US6342499B1 (en) 1998-07-14 2002-01-29 Basf Aktiengesellschaft Parasitic and saprophagous mite control in beneficial insects
WO2000049001A2 (fr) * 1999-02-16 2000-08-24 E.I. Du Pont De Nemours And Company Phenoxypyrimidines insecticides et acaricides
WO2000049001A3 (fr) * 1999-02-16 2000-12-21 Du Pont Phenoxypyrimidines insecticides et acaricides
WO2000071536A1 (fr) * 1999-05-20 2000-11-30 E.I. Du Pont De Nemours And Company Heteroaryloxypyrimidine insecticides et acaricides
EP2222162A4 (fr) * 2007-11-28 2012-01-18 Dana Farber Cancer Inst Inc Inhibiteurs myristate à petites molécules de bcr-abl et procédés d'utilisation
JP2011504927A (ja) * 2007-11-28 2011-02-17 ダナ−ファーバー キャンサー インスティテュート インク． Ｂｃｒ−ａｂｌの低分子のミリスチン酸エステル阻害剤及びその使用方法
EP2222162A2 (fr) * 2007-11-28 2010-09-01 Dana Farber Cancer Institute Inhibiteurs myristate à petites molécules de bcr-abl et procédés d'utilisation
AU2008331867B2 (en) * 2007-11-28 2014-05-22 Dana-Farber Cancer Institute, Inc. Small molecule myristate inhibitors of Bcr-abl and methods of use
US8921336B2 (en) 2007-11-28 2014-12-30 Dana-Farber Cancer Institute, Inc. Small molecule myristate inhibitors of BCR-ABL and methods of use
CN104311563A (zh) * 2007-11-28 2015-01-28 达那-法伯癌症研究所 Bcr-abl的小分子豆蔻酸酯抑制剂及其使用方法
CN104311563B (zh) * 2007-11-28 2016-12-07 达那-法伯癌症研究所 Bcr-abl的小分子豆蔻酸酯抑制剂及其使用方法
US9670214B2 (en) 2007-11-28 2017-06-06 Dana-Farber Cancer Institute, Inc. Small molecule myristate inhibitors of Bcr-abl and methods of use
US10787455B2 (en) 2007-11-28 2020-09-29 Dana-Farber Cancer Institute, Inc. Small molecule myristate inhibitors of BCR-ABL and methods of use
US11254682B2 (en) 2007-11-28 2022-02-22 The Scripps Research Institute Small molecule myristate inhibitors of Bcr-abl and methods of use
US11932646B2 (en) 2007-11-28 2024-03-19 The Scripps Research Institute Small molecule myristate inhibitors of Bcr-abl and methods of use

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