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WO1992016527A1 - Derive de pyridine substitue en position 2, sa production, et bactericide d'agrohorticulture - Google Patents

Derive de pyridine substitue en position 2, sa production, et bactericide d'agrohorticulture Download PDF

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Publication number
WO1992016527A1
WO1992016527A1 PCT/JP1992/000336 JP9200336W WO9216527A1 WO 1992016527 A1 WO1992016527 A1 WO 1992016527A1 JP 9200336 W JP9200336 W JP 9200336W WO 9216527 A1 WO9216527 A1 WO 9216527A1
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Prior art keywords
group
compound
formula
general formula
optionally substituted
Prior art date
Application number
PCT/JP1992/000336
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English (en)
Japanese (ja)
Inventor
Isamu Kasahara
Teruyuki Iihama
Shou Hashimoto
Shinsuke Sano
Hiroyasu Hosokawa
Original Assignee
Nippon Soda Co., Ltd.
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 Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU14223/92A priority Critical patent/AU1422392A/en
Publication of WO1992016527A1 publication Critical patent/WO1992016527A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to a novel pyridine derivative, a method for producing the same, and a fungicide for agricultural and horticultural use.
  • Japanese Patent Application Laid-Open Nos. 54-17070 and 61-37784 disclose compounds similar to the compound of the present invention. Disclosure of the invention:
  • An object of the present invention is to provide a novel compound which can be industrially advantageously synthesized, has a certain effect, and can be used as an agricultural and horticultural fungicide which can be used safely.
  • the present invention has the general formula (I):
  • A represents an optionally substituted aryl group or an optionally substituted heteroaryl group
  • B is an oxygen atom, a sulfur atom, a formula —N (R 1 ) — (wherein, R 1 represents a hydrogen atom, a lower alkyl group or an acyl group.),
  • r 1 , r 2 , r 3 , r, r 5 , and r 6 are each a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxy group, a cyano group, a phenyl group, and a lower alkylcarbonyloxy group.
  • n 0 or 1
  • Y is a lower alkyl group, a halogen atom, a lower alkoxy group, an acyloxy group, a benzyloxy group, a lower alkylsulfonyloxy group, an optionally substituted phenylsulfonyloxy group
  • a cyano group, a lower alkylthio group, a mono- or di-lower-alkylamino group, a carbamoyloxyalkyl group, a compound represented by the formula: CH-CH—CH CH—, or a lower alkoxy group.
  • n 0, 1 or 2;
  • the method for producing the compound of the present invention is as follows.
  • L represents a leaving group
  • A, B, n, R, Y, m, and q have the same meaning as described above.
  • Examples of the leaving group for L include a halogen such as bromine and chlorine, a methanesulfonyl group, and a tosyl group.
  • solvents that can be used include alcohols such as ethanol, methanol, and n-propanol; ethers such as dioxane, tetrahydrofuran, dimethoxetane, and dimethyl ether; cellsolves such as methylcellsolve and ethylcellsolve; benzene; and toluene.
  • examples include hydrocarbons, halogenated hydrocarbons such as carbon tetrachloride, and chloroform, water, DMF, and DMS0.
  • the precipitate is filtered from the reaction solution after completion of the reaction to obtain an HL salt or a thiazolylpyridine compound corresponding to the general formula [I] ′.
  • it is neutralized, subjected to ordinary post-treatments such as extraction, and, if necessary, subjected to operations such as chromatography and recrystallization to give the desired thiazolylpyridine compound represented by the general formula [I] ′.
  • L is a halogen in the pyridine derivative represented by the general formula [III], it can be synthesized by the following route.
  • Hal represents a halogen atom
  • Y, m, and R have the same meaning as described above.
  • a cyano viridine derivative represented by the general formula [IV] obtained by the method described in J. Org. Chem., 48, 1375 (1983) and a Grignard reagent represented by the general formula [V]. Or by reacting with an alkyl lithium represented by the general formula (VI), and further by subjecting the obtained imidium salt to acid hydrolysis.
  • a biliyl ketone derivative represented by the general formula [Vi i] is obtained. Further, this ketone derivative is converted to a brominating agent such as pyridinium bromide or bromine, or a chlorinating agent such as sulfuryl chloride or chlorine.
  • a haloketone derivative represented by the general formula [ ⁇ ⁇ _1] is obtained.
  • the compound of the present invention may have the following (b), (c), (d),
  • Se0 oxidizing agent such as 2
  • This reaction is carried out in a solvent such as ethers such as dioxane, alcohols such as ethanol, water and mixtures thereof, For 10 minutes to 24 hours. Further, it can also be obtained by using an oxidizing agent such as chromic anhydride, manganese dioxide, and potassium permanganate described in ACS Monograph 186 "Oxidations in Organic Chemistry," 1990, 103-104.
  • a solvent such as ethers such as dioxane, alcohols such as ethanol, water and mixtures thereof.
  • an oxidizing agent such as chromic anhydride, manganese dioxide, and potassium permanganate described in ACS Monograph 186 "Oxidations in Organic Chemistry," 1990, 103-104.
  • R ′ represents an electron-withdrawing group such as nitrile or carboxylate
  • L, D, Y, m, q, and A have the same meaning as described above.
  • This reaction proceeds in a solvent in the presence of a base at 0 to 150 ° C for 1 to 24 hours.
  • the solvent include aromatic hydrocarbons such as DMF, DMSO, benzene, and toluene, ethers such as dioxane, tetrahydrofuran, and getyl ether, and the like, and mixtures thereof.
  • Examples of the base include alkali metal hydrides such as sodium hydride, alkyl lithiums such as n-butyl lithium, alkali metal alkoxides such as sodium methoxide, and inorganic bases such as sodium hydroxide. And organic bases such as DBU.
  • alkali metal hydrides such as sodium hydride
  • alkyl lithiums such as n-butyl lithium
  • alkali metal alkoxides such as sodium methoxide
  • inorganic bases such as sodium hydroxide.
  • organic bases such as DBU.
  • B ′ represents an oxygen atom, a sulfur atom, and the formula —NR 1 — (R has the same meaning as described above.), And L, D, Y, m, q, and A have the same meanings as described above. .
  • This reaction can be obtained by reacting in the absence of a solvent, preferably in a solvent, in the presence of a base at 0 to 150 for 1 to 24 hours. Wear.
  • the solvent examples include aromatic hydrocarbons such as DMF, DMSO, benzene and toluene, ethers such as dioxane and tetrahydrofuran, etc., acetonitril, pyridine, water and the like, and mixtures thereof.
  • aromatic hydrocarbons such as DMF, DMSO, benzene and toluene
  • ethers such as dioxane and tetrahydrofuran, etc.
  • acetonitril pyridine, water and the like, and mixtures thereof.
  • the base examples include alkali metal hydrides such as sodium hydride, alkyl lithiums such as n-butyl lithium, alkali metal alkoxides such as sodium methoxide, and carbon dioxide.
  • examples include inorganic bases such as lime and sodium hydroxide, and organic bases such as triethylamine and pyridin.
  • the substrate is an aniline, it can also serve as a solvent and a base.
  • L ′ represents a halogen atom such as chlorine, bromine, iodine or the like or an alkylthio group
  • B ⁇ represents the above.
  • M represents a Grignard residue of MgC ⁇ , MgBr or Mgl.
  • This reaction is carried out in a solvent in the presence of a catalyst.
  • catalysts examples include transition metal catalysts typified by nickel chloride diphenylphosphinoethane.
  • This reaction is performed by heat treatment in a solvent in the presence of an oxidizing agent.
  • a solvent include aromatic hydrocarbons such as benzene and toluene, ethers such as dioxane and tetrahydrofuran, halogenated hydrocarbons such as carbon tetrachloride and the like, and mixtures thereof.
  • the oxidizing agent include iodine, bromine, aqueous hydrogen peroxide and the like.
  • a 1,2,4-thiadiazole compound of the general formula [I] wherein D is a nitrogen atom is synthesized by a method described in ELSEVIER, Rodd's Chemistry of Carbon Compounds volume WD pl27-130 (1986). can do.
  • the desired product after completion of the reaction, the desired product can be obtained by performing ordinary post-treatment.
  • the structure of the compound of the present invention was determined from IR, NMR, MASS and the like.
  • Example 1 the compound of the present invention will be further described with reference to Examples and Reference Examples.
  • Example 1 the compound of the present invention will be further described with reference to Examples and Reference Examples.
  • the port-form layer was washed with a 1N aqueous sodium hydroxide solution, further washed with a saturated saline solution, and dried over anhydrous magnesium sulfate.
  • a Grignard solution was prepared by stirring 0.57 g of benzene chloride and 0.09 g of magnesium in 5 ml of ether at room temperature for 2 hours.
  • Cold water was added to the reaction solution under ice-cooling, and the aqueous layer was further acidified to pH 1 with a 3N hydrochloric acid aqueous solution, followed by stirring at room temperature for 30 minutes.
  • T_9 2-C1 // // li> t oDJ
  • the compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi, it can be used for controlling various diseases that occur during cultivation of agricultural and horticultural crops including flowers, turf and pasture.
  • brown spot of sugar beet (Cercosporabetico 1a)
  • brown spot of laccasei (Mycosphaerellaarachidi s)
  • P. kuroshibu (Mycosphaerellaberkeley i)
  • powdery mildew of cucumber S phaerothecafuligina no.
  • benzimidazole fungicides for example, thiophane monomethyl, benomyl, carbendazim), gray mold (B_o try t_is_cinerea), sugar beet brown spot (Cercosporabeticola), and lingos Fungus (Venturiainaequalis)
  • the compounds of the present invention are also effective against pear scabs (Venturianashicola) as well as susceptible bacteria.
  • the compound of the present invention is similar to bacteria that are resistant to gray mold fungi (B 0 trytiscinerea) that show shochu properties on dicarboximide fungicides (eg, vinclozolin, procymidone, ibrodione). It is valid.
  • gray mold fungi B 0 trytiscinerea
  • dicarboximide fungicides eg, vinclozolin, procymidone, ibrodione. It is valid.
  • the compound of the present invention may not be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets.
  • the thus-obtained compound of the present invention when the thus-obtained compound of the present invention is actually applied, it can be used in an absolute frame without adding other components, and can be in a form that a general pesticide can take for the purpose of being used as a pesticide, that is, It can also be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions and the like.
  • solid additives are used as additives and carriers, vegetable powders such as soybean flour, flour, etc., diatomaceous earth, limestone, gypsum, talc, ⁇ , etc.
  • Mineral fine powders such as irophyllite, clay, mineral oil, and vegetable oil are used.
  • kerosene, mineral oil, petroleum, sorbent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate, mineral oil Use vegetable oil, water, etc. as solvents.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • Wettable powder, emulsion obtained in this way Is used as a suspension or an emulsion by diluting it to a predetermined concentration with water, and the powder and granules are used as they are sprayed on plants.
  • the additives and the addition ratio are not limited to these examples, but can be changed in a wide range. Parts in Formulation Examples are parts by weight.
  • Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts By uniformly mixing and pulverizing finely, a wettable powder with an active ingredient of 40% is obtained.
  • Compound of the present invention 5 parts Clay 7 3 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Sodium phosphate 1 part More than pulverize and mix well and add water. After kneading, the mixture is granulated and dried to obtain granules containing 5% of active ingredient.
  • Compound of the present invention 10 parts Sodium ligninsulfonate 4 parts Sodium dodecylbenzenesulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts or more are mixed. If wet grinding is performed, a suspension containing the active ingredient at 10% is obtained.
  • fungicides insecticides, pesticides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Jibere Li emissions (such Jibere Li down A 3, Jibere Li down A 4, Jibere Li down A 7) I AA, NAA.
  • Test Examples show that the compound of the present invention is useful as an active ingredient of various plant disease controlling agents.
  • the control effect can be evaluated by visually observing the disease state of the test plant at the time of the survey, that is, the degree of growth of the lesions and fungi appearing on the leaves and stems. j, "4" if about 10% is recognized compared to the untreated area,
  • V- 12 // 5 1 0 Table (continued)
  • Test example 3 Wheat powdery mildew control test (prevention test)
  • a rice blast (variety “Nipponbare j, 3.0 leaf stage”) planted in a plastic pot was sprayed with a chemical solution of a wettable powder of the compound of the present invention at a predetermined concentration, air-dried at room temperature, and cultivated.
  • the plants were grown in a constant temperature room at a temperature of 70% or more at a temperature of 70 ° C.
  • the disease status was investigated 7 days after the inoculation, and the control effect was determined, and the results are shown in Table 13.
  • Test Example 5 Wheat eye spot control test (Treatment test)
  • Wheat seedlings grown in plastic pots were spray-inoculated with a suspension of conidiospores of wheat eye spot fungus (Pseudocercosporellaher potrichoides) obtained by culture, and sprayed. After maintaining the high humidity in the dark for 4 days, a chemical solution of a wettable powder of the compound of the present invention was sprayed at a predetermined concentration and air-dried at room temperature. The plants were grown under repeated lighting and darkness under humidity, and 35 days after inoculation, the onset of the disease was investigated, and the control effect was determined, and the results are shown in Table 14.
  • a predetermined concentration of a wettable powder of the compound of the present invention was sprayed onto a seedling of Lingo (cultivar “Kunimitsu j, 3-4 leaf stage”) cultivated in an unglazed pot and air-dried. 1 is) and kept in a room at 20 ° C and high humidity for 2 weeks under light (bright and dark), and the control effect was investigated. It is shown in the table.
  • Test Example 7 Control test for prevention of gray mold on cucumber (preventive test) To a young cucumber (variety “Four-leaf J, 1.0-leaf stage”) grown in an unbaked pot, a chemical solution of a predetermined concentration of a wettable powder of the compound of the present invention was applied to young seedlings. After spraying, the plants were air-dried at room temperature, and cultivated gray mold (Botrytiscie a_, a bacterium susceptible to benzimidazole and dicarboxymid), and a drug-sensitive bacterium. bacteria resistant to.
  • a medicinal solution of a predetermined concentration of a wettable powder of the compound of the present invention was sprayed on young seedlings of laccase (cultivar “Nacateyuta Riki”, 4.0 bileaf stage) raised in unglazed pots. After spraying, the plants are air-dried at room temperature, spray-inoculated with a suspension of the spores of the lactobacillus brown spot disease fungus (CMy cosphaerellaarachidis) obtained by culturing, and kept at 24 to 28 days in high humidity for 1 day. They were grown in a greenhouse at ⁇ 30 ° C for 12 days, their disease status was investigated, and the control effect was determined. The results are shown in Table 17.

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Un composé, ainsi que son sel, ont une activité bactéricide dans le domaine de l'agrohorticulture et sont représentés par la formule générale (I) dans laquelle A représente aryle ou hétéroaryle éventuellement substitués; B représente oxygène, soufre, -NR?1- (où R1¿ représente hydrogène, acyle ou alkyle inférieur), (a), ou (b), dans lesquels R1 jusqu'à R2 représentent hydrogène, halogène, etc.; n vaut 0 ou 1; D représente -CR= (où R représente hydrogène, halogène etc.) ou azote; Y représente alkyle inférieur, halogène, etc.; m vaut 0, 1 ou 2; et q vaut 0 ou 1.
PCT/JP1992/000336 1991-03-22 1992-03-19 Derive de pyridine substitue en position 2, sa production, et bactericide d'agrohorticulture WO1992016527A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU14223/92A AU1422392A (en) 1991-03-22 1992-03-19 2-substituted pyridine derivative, production thereof, and agrohorticultural bactericide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3/83590 1991-03-22
JP8359091 1991-03-22
JP3/255891 1991-09-09
JP25589191 1991-09-09

Publications (1)

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WO1992016527A1 true WO1992016527A1 (fr) 1992-10-01

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CN (1) CN1065268A (fr)
AU (1) AU1422392A (fr)
IL (1) IL101291A0 (fr)
TW (1) TW199895B (fr)
WO (1) WO1992016527A1 (fr)

Cited By (22)

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WO1994012496A1 (fr) * 1992-11-26 1994-06-09 Bayer Aktiengesellschaft 3-pyridyl-1,2,4-thiadiazoles utilises comme pesticides
JP2000007658A (ja) * 1998-04-23 2000-01-11 Takeda Chem Ind Ltd ナフタレン誘導体
US6184225B1 (en) 1996-02-13 2001-02-06 Zeneca Limited Quinazoline derivatives as VEGF inhibitors
US6265411B1 (en) 1996-05-06 2001-07-24 Zeneca Limited Oxindole derivatives
US6291455B1 (en) 1996-03-05 2001-09-18 Zeneca Limited 4-anilinoquinazoline derivatives
US6294532B1 (en) 1997-08-22 2001-09-25 Zeneca Limited Oxindolylquinazoline derivatives as angiogenesis inhibitors
WO2003006015A1 (fr) * 2001-07-13 2003-01-23 Bristol-Myers Squibb Pharma Company Thiazoles et oxazoles substitutes utilises comme ligands hormonaux de liberation de la corticotrophine
US6573289B1 (en) 1998-04-23 2003-06-03 Takeda Chemical Industries, Ltd. Naphthalene derivatives, their production and use
US6673803B2 (en) 1996-09-25 2004-01-06 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
WO2004033452A1 (fr) * 2002-10-11 2004-04-22 Sumitomo Chemical Company, Limited Compose de thiadiazole et son utilisation
US7105550B2 (en) 2000-03-01 2006-09-12 Christopher Love 2,4-disubstituted thiazolyl derivatives
US7160889B2 (en) 2000-04-07 2007-01-09 Astrazeneca Ab Quinazoline compounds
US7173038B1 (en) 1999-11-05 2007-02-06 Astrazeneca Ab Quinazoline derivatives as VEGF inhibitors
US7262201B1 (en) 1998-10-08 2007-08-28 Astrazeneca Ab Quinazoline derivatives
CN100448868C (zh) * 2002-04-04 2009-01-07 比奥根艾迪克Ma公司 三取代的杂芳基以及制备方法和其用途
WO2009123316A1 (fr) 2008-04-04 2009-10-08 武田薬品工業株式会社 Dérivé hétérocyclique et son utilisation
US8686007B2 (en) 2011-04-22 2014-04-01 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
US9604965B2 (en) 2010-04-23 2017-03-28 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US9730886B2 (en) 2010-04-23 2017-08-15 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
JP2023062154A (ja) * 2017-04-06 2023-05-02 エフ エム シー コーポレーション 殺真菌性オキサジアゾール
WO2023158602A1 (fr) * 2022-02-15 2023-08-24 Fmc Corporation Halométhylcétones, hydrates et éthers d'énol fongicides

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CN103183669B (zh) * 2011-12-27 2015-11-18 湖南化工研究院 噻唑甲胺基吡啶类化合物及其制备方法
CN104387377B (zh) * 2014-10-14 2017-03-29 湖南海利常德农药化工有限公司 一种噻唑甲胺基吡啶类化合物的制备方法

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Cited By (45)

* Cited by examiner, † Cited by third party
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US5633267A (en) * 1992-11-26 1997-05-27 Bayer Aktiengesellschaft Pyridyl-1,2,4-thiadiazoles as pest-control agents
US5756523A (en) * 1992-11-26 1998-05-26 Bayer Aktiengesellschaft Pyridyl-1,2,4-thiadiazoles
WO1994012496A1 (fr) * 1992-11-26 1994-06-09 Bayer Aktiengesellschaft 3-pyridyl-1,2,4-thiadiazoles utilises comme pesticides
US6031104A (en) * 1992-11-26 2000-02-29 Bayer Aktiengesellschaft Pyridyl-1,2,4-thiadiazoles
US6100402A (en) * 1992-11-26 2000-08-08 Bayer Aktiengesellschaft Pyridyl-1,2,4-thiadiazoles
US6184225B1 (en) 1996-02-13 2001-02-06 Zeneca Limited Quinazoline derivatives as VEGF inhibitors
US6291455B1 (en) 1996-03-05 2001-09-18 Zeneca Limited 4-anilinoquinazoline derivatives
US6265411B1 (en) 1996-05-06 2001-07-24 Zeneca Limited Oxindole derivatives
US6673803B2 (en) 1996-09-25 2004-01-06 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
USRE42353E1 (en) 1996-09-25 2011-05-10 Astrazeneca Uk Limited Quinazoline derivatives and pharmaceutical compositions containing them
US6897210B2 (en) 1996-09-25 2005-05-24 Zeneca Limited Quinazoline derivatives and pharmaceutical compositions containing them
US6294532B1 (en) 1997-08-22 2001-09-25 Zeneca Limited Oxindolylquinazoline derivatives as angiogenesis inhibitors
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AU1422392A (en) 1992-10-21
IL101291A0 (en) 1992-11-15
CN1065268A (zh) 1992-10-14

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