WO1992007835A1 - Fongicides aux imidazoles - Google Patents

Fongicides aux imidazoles Download PDF

Info

Publication number
WO1992007835A1
WO1992007835A1 PCT/GB1991/001836 GB9101836W WO9207835A1 WO 1992007835 A1 WO1992007835 A1 WO 1992007835A1 GB 9101836 W GB9101836 W GB 9101836W WO 9207835 A1 WO9207835 A1 WO 9207835A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
alkyl
compound
aryl
alkenyl
Prior art date
Application number
PCT/GB1991/001836
Other languages
English (en)
Inventor
John Henry Parsons
Russell George Hunt
Philip John Dudfield
Original Assignee
Schering Agrochemicals Limited
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 Schering Agrochemicals Limited filed Critical Schering Agrochemicals Limited
Publication of WO1992007835A1 publication Critical patent/WO1992007835A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/70—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3

Definitions

  • This invention relates to imidazole fungicides.
  • R 1 is -S0 ⁇ 7 2R- , -P-R 7 or -COR 8
  • R 5 is aryl, optionally substituted alkyl or optionally substituted amino
  • R 6 and R 7 may be the same or different and are amino, alkoxy or alkylthio, each of which is optionally substituted;
  • R 8 has the same meaning as R 5 or can be alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy;
  • R 9 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, acyl, aryl or cycloalkyl;
  • R 10 is hydrogen, optionally substituted alkyl, alkenyl or alkynyl
  • R 11 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, all of which are optionally substituted, or is aryl;
  • ,12 has the same meaning as Rll or is acyl
  • Z is oxygen or sulfur; and p is 0 or 1.
  • R 3 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkanoyl or amino, all of which are optionally substituted, hydrogen, halogen, hydroxy, nitro, acyl,
  • R 12 0 or aryl
  • R 5 is aryl, optionally substituted alkyl or optionally substituted amino
  • R 6 and R 7 may be the same or different and are amino, alkoxy or alkylthio, each of which is optionally substituted
  • R 9 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, acyl, aryl or cycloalkyl
  • R 10 is hydrogen, optionally substituted alkyl, alkenyl or lkynyl
  • R 11 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl or amino, all of which are optionally substituted, or is aryl;
  • R 12 has the same meaning as R 11 or is acyl; Z is oxygen or sulfur; and p is 0, 1 or 2.
  • Alkyl, alkanoyl and alkoxy groups are preferably of 1 to 8 carbon atoms, especially methyl, and alkenyl and alkynyl groups are usually of 3 to 4 carbon atoms. Substituents, when present on any such group, include halogen, hydroxy, alkoxy and aryl.
  • Aryl groups are usually phenyl, optionally substituted, e.g.
  • R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
  • R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
  • R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
  • sulfamoyl optionally substituted amino, alkyl-SO , or aryl-SO , where g is 0, 1 or 2, and any alkyl or alkoxy group is optionally substituted.
  • aryl may include heteroaryl groups such as thienyl, furyl or pyridyl and can also include polynuclear aromatic groups, such as naphthyl and benzimidazolyl.
  • acyl can include residues of both carboxylic and sulfonic acids and includes the groups R 13 (0) r C0 and R 13 S0 2 , where R 13 has the same meaning as R 11 , or is optionally substituted amino and r is 0 or 1. It thus includes residues of carba ic and sulfa ic acids.
  • Acyl groups are preferably alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, N,N-dialkylsulfamoyl or N-alkyl-N-arylsulfamoyl, in which the alkyl groups are e.g. of 1 to 4 carbon atoms, and the alkyl and phenyl can be substituted as previously mentioned.
  • Amino groups are usually substituted by one or more of the groups R 11 , acyl, optionally substituted amino (including groups substituted through a double bond) , hydroxy or optionally substituted alkoxy, or two substituents can form a ring, e.g. a morpholino or piperidino ring.
  • Sulfamoyl groups can be substituted similarly to amino groups.
  • Cycloalkyl groups are usually of 3 to 8 carbon atoms especially cyclopentyl or cyclohexyl.
  • R 1 is generally a substituted sulfamoyl group, especially dimethylsulfamoyl.
  • R 2 is preferably cyano or thiocarbamoyl.
  • R 3 is preferably phenyl or benzoyl, optionally substituted by up to three groups, selected from halogen, alkyl (especially methyl) , trifluoromethyl, nitro and alkoxy (especially methoxy) .
  • the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. downy mildews, especially vine downy mildew fPlasmopara viticola) , and late tomato blight and potato blight fPhytophthora infestans . They are also active against powdery mildews, such as barley powdery mildew (Erysiphe ⁇ raminis) , as well as being active against diseases such as rice blast (Pyricularia orvzae) and apple scab (Venturia inaequalis) . They may also have activity against other fungi, such as Botrvtis spp. ,
  • the invention thus also provides a method of combating fungi at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I.
  • the invention also provides an agricultural composition
  • an agricultural composition comprising a compound of formula I in admixture with an agriculturally acceptable diluent or carrier.
  • composition of the invention may of course include more than one compound of the invention.
  • composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal,insecticidal or acaricidal properties.
  • additional active ingredients for example compounds known to possess plant-growth regulant, herbicidal, fungicidal,insecticidal or acaricidal properties.
  • the compounds of the invention can be used in sequence with the other active ingredient.
  • the diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent, emulsifying agent or wetting agent.
  • Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono- or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulfates such as sodium dodecyl sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; ethoxylated fatty alcohol sulfates; ethoxylated alkylphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene s
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • amide sulfonates e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl- 5-decyne-4,7-diol, or ethoxylated acetylenic glycols.
  • a cationic surface-active agent examples include, for instance, an aliphatic mono-, di- or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
  • a dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example, kaolin.
  • a granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient absorbed or adsorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.
  • Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.01 to 3.0 per cent by weight, especially 0.01 to 1.0 per cent by weight.
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
  • the compound is generally applied to seeds, plants or their habitat.
  • the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds.
  • the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds.
  • a suitable application rate is within the range of from 0.01 to 10 kg per hectare, more preferably from 0.05 to 1 kg per hectare.
  • the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure.
  • the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged.
  • the spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary.
  • a suitable rate of application is from 0.01 to 10 kg. per hectare, preferably from 0.05 to 5 kg per hectare.
  • the compounds of the invention may be prepared, in known manner, in a variety of ways, for example by reacting a compound of formula II ⁇ N
  • R 2 is as defined above, except for thiocarbamoyl, with a compound of formula R*Q, where Q is a leaving group, such as halogen, especially chlorine.
  • Compounds of formula II can be obtained by reacting the corresponding compound where R 2 is trihalomethyl with ammonium hydroxide to give a compound where R 2 is cyano.
  • Compounds of formula I, where R 2 is cyano can be modified in known manner to give compounds where R 2 is thiocarbamoyl, by reaction with hydrogen sulfide and if desired modifying this group in known manner to give compounds where R 9 is not hydrogen. These reactions are usually carried out using a suitable acyl halide or isocyanate, for instance as described in EP 219192.
  • R 30 CO is the same alkanoyl or aroyl group, e.g. using a dichromate, such as pyridinium dichromate.
  • the invention is illustrated in the following Examples. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses. Temperatures are in °C and are uncorrected.
  • the compounds of the invention were assessed for activity against one or more of the following:
  • Plasmopara viticola vine downy mildew (PV)
  • Phytophthora infestans late tomato blight (PI)
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were sprayed onto the appropriate plant and then inoculated by spraying with spore suspensions of the fungi. Plants were then kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the leaf surface was visually estimated.

Landscapes

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

Abstract

Composés de la formule (I), dans laquelle R1 représente -SO¿2R?5 ou (a), R2 is -CN, (b) ou -CH=N-OR10, R3 est alcoyle, cycloalkyle, cycloalcényle, alcényle, alcynyle, alcanoyle, ou amino, tous étant éventuellement substitués, hydrogène, halogène, hydroxy, nitro, acyle, R12O ou aryle; R5 est aryle, alkyle éventuellement substitué ou amino éventuellement substitué; R6 et R7 peuvent être identiques ou différents, et sont amino, alkoxy ou alkylthio, chacun étant éventuellement substitué; R9 est hydrogène, alkyle, alcényle, alcynyle, alcoxycarbonyle, acyle, aryle ou cycloalkyle éventuellement substitué; R10 est hydrogène, alcyle, alcényle ou alcynyle éventuellement substitué; R11 est alcyle, cycloalkyle, cycloalcényle, alcényle, alcynyle ou amino, tous étant éventuellement substitués, ou aryle; R12 a la même notation R11 ou est acyle; Z est oxygène ou soufre; et p est 0, 1 ou 2; lesdits composés présentent une activité contre les champignons phytopathogènes.
PCT/GB1991/001836 1990-10-24 1991-10-21 Fongicides aux imidazoles WO1992007835A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909023082A GB9023082D0 (en) 1990-10-24 1990-10-24 Fungicides
GB9023082.2 1990-10-24

Publications (1)

Publication Number Publication Date
WO1992007835A1 true WO1992007835A1 (fr) 1992-05-14

Family

ID=10684244

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/001836 WO1992007835A1 (fr) 1990-10-24 1991-10-21 Fongicides aux imidazoles

Country Status (2)

Country Link
GB (1) GB9023082D0 (fr)
WO (1) WO1992007835A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6043377A (en) * 1996-06-11 2000-03-28 Bayer Aktiengesellschaft Imidazole compounds
US9873671B2 (en) 2014-01-16 2018-01-23 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9884818B2 (en) 2013-05-17 2018-02-06 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9895349B2 (en) 2013-04-03 2018-02-20 Janssen Sciences Ireland Us N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10071961B2 (en) 2013-10-23 2018-09-11 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10077239B2 (en) 2015-09-29 2018-09-18 Novira Therapeutics, Inc. Crystalline forms of a hepatitis B antiviral agent
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10160743B2 (en) 2013-05-17 2018-12-25 Janssen Sciences Ireland Uc Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10196376B2 (en) 2011-12-21 2019-02-05 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US10213420B2 (en) 2014-02-05 2019-02-26 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
JP2019069940A (ja) * 2012-08-28 2019-05-09 ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー スルファモイル−アリールアミド及びｂ型肝炎の治療のための薬剤としてのその使用
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US10441589B2 (en) 2016-04-15 2019-10-15 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US10450270B2 (en) 2013-07-25 2019-10-22 Janssen Sciences Ireland Uc Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10537580B2 (en) 2015-03-19 2020-01-21 Novira Therapeutics, Inc. Azocane and azonane derivatives and methods of treating hepatitis B infections
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10973801B2 (en) 2018-03-14 2021-04-13 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
US11491148B2 (en) 2019-05-06 2022-11-08 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4574010A (en) * 1985-05-06 1986-03-04 Stauffer Chemical Company Herbicidal esters of N-substituted 2-bromo-4-methylimidazole-5-carboxylic acid
EP0284277A1 (fr) * 1987-03-21 1988-09-28 AgrEvo UK Limited Fongicides de cyanoimidazole
EP0337103A2 (fr) * 1988-03-11 1989-10-18 ISHIHARA SANGYO KAISHA, Ltd. Composition biocide
EP0432892A1 (fr) * 1989-11-15 1991-06-19 AgrEvo UK Limited Fongicides dérivés de l'imidazol
EP0298196B1 (fr) * 1987-03-13 1993-06-02 Ishihara Sangyo Kaisha, Ltd. Composés d'imidazole et compositions biocides les contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4574010A (en) * 1985-05-06 1986-03-04 Stauffer Chemical Company Herbicidal esters of N-substituted 2-bromo-4-methylimidazole-5-carboxylic acid
EP0298196B1 (fr) * 1987-03-13 1993-06-02 Ishihara Sangyo Kaisha, Ltd. Composés d'imidazole et compositions biocides les contenant
EP0284277A1 (fr) * 1987-03-21 1988-09-28 AgrEvo UK Limited Fongicides de cyanoimidazole
EP0337103A2 (fr) * 1988-03-11 1989-10-18 ISHIHARA SANGYO KAISHA, Ltd. Composition biocide
EP0432892A1 (fr) * 1989-11-15 1991-06-19 AgrEvo UK Limited Fongicides dérivés de l'imidazol

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6043377A (en) * 1996-06-11 2000-03-28 Bayer Aktiengesellschaft Imidazole compounds
US10196376B2 (en) 2011-12-21 2019-02-05 Novira Therapeutics, Inc. Hepatitis B antiviral agents
US10995064B2 (en) * 2012-08-28 2021-05-04 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10676429B2 (en) 2012-08-28 2020-06-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
AU2018204597B2 (en) * 2012-08-28 2020-03-05 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of Hepatitis B
JP2019069940A (ja) * 2012-08-28 2019-05-09 ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー スルファモイル−アリールアミド及びｂ型肝炎の治療のための薬剤としてのその使用
US10941113B2 (en) 2013-02-28 2021-03-09 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US10125094B2 (en) 2013-02-28 2018-11-13 Janssen Sciences Ireland Uc Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B
US9895349B2 (en) 2013-04-03 2018-02-20 Janssen Sciences Ireland Us N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10398677B2 (en) 2013-04-03 2019-09-03 Janssen Sciences Ireland Uc N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10457638B2 (en) 2013-05-17 2019-10-29 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10160743B2 (en) 2013-05-17 2018-12-25 Janssen Sciences Ireland Uc Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US9884818B2 (en) 2013-05-17 2018-02-06 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10450270B2 (en) 2013-07-25 2019-10-22 Janssen Sciences Ireland Uc Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10377709B2 (en) 2013-10-23 2019-08-13 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10071961B2 (en) 2013-10-23 2018-09-11 Janssen Sciences Ireland Uc Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10392349B2 (en) 2014-01-16 2019-08-27 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US9873671B2 (en) 2014-01-16 2018-01-23 Novira Therapeutics, Inc. Azepane derivatives and methods of treating hepatitis B infections
US10213420B2 (en) 2014-02-05 2019-02-26 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US10632112B2 (en) 2014-02-05 2020-04-28 Novira Therapeutics, Inc. Combination therapy for treatment of HBV infections
US11078193B2 (en) 2014-02-06 2021-08-03 Janssen Sciences Ireland Uc Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10537580B2 (en) 2015-03-19 2020-01-21 Novira Therapeutics, Inc. Azocane and azonane derivatives and methods of treating hepatitis B infections
US10875876B2 (en) 2015-07-02 2020-12-29 Janssen Sciences Ireland Uc Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B
US10077239B2 (en) 2015-09-29 2018-09-18 Novira Therapeutics, Inc. Crystalline forms of a hepatitis B antiviral agent
US10441589B2 (en) 2016-04-15 2019-10-15 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US11129834B2 (en) 2016-04-15 2021-09-28 Novira Therapeutics, Inc. Combinations and methods comprising a capsid assembly inhibitor
US10973801B2 (en) 2018-03-14 2021-04-13 Janssen Sciences Ireland Unlimited Company Capsid assembly modulator dosing regimen
US11096931B2 (en) 2019-02-22 2021-08-24 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases
US11491148B2 (en) 2019-05-06 2022-11-08 Janssen Sciences Ireland Unlimited Company Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases

Also Published As

Publication number Publication date
GB9023082D0 (en) 1990-12-05

Similar Documents

Publication Publication Date Title
EP0299694B1 (fr) Acrylates fongicides
WO1992007835A1 (fr) Fongicides aux imidazoles
EP0750611B1 (fr) Derives d'anilide utilises comme fongicides
US5093364A (en) 5-fluoroanthranilic fungicides
EP0378308B1 (fr) Fongicides acryliques
US6541630B1 (en) Fungicides
AU601558B2 (en) Fungicidal imidazole and 1,2,4-triazole derivatives
JPH0670033B2 (ja) １‐ヘテロアリール‐４‐アリール‐ピラゾリン‐５‐オン
AP225A (en) Imadazole fungicides.
US4783459A (en) Anilinopyrimidine fungicides
GB2173791A (en) Fungicidal cyano oximes
US5096915A (en) Azole fungicides
US5045557A (en) Imidazable fungicides and use thereof
WO1996029305A1 (fr) Composes fongicides
EP0606228B1 (fr) Derives d'acide propenoique
EP0245991A2 (fr) Benzothiazolines comme fongicides
JPS60202868A (ja) 新規なトリアゾリルアルキル誘導体、それらの製造方法ならびにそれらを含有する植物生長調整剤および殺菌剤
EP0337616A1 (fr) Benzthiazoles comme fungicides
JPS60239485A (ja) 環式アゾリルビニルエーテル
HU202367B (en) Fungicide and bactericide compositions containing pyrimidine derivative as active components and process for producing new pyrimidine derivatives
GB2225011A (en) Fungicidal acrylates
WO1998014438A1 (fr) Derives de bisthiadiazole et sels de ces derives, agents en usage dans l'agriculture et l'horticulture pour lutter contre les maladies vegetales, et procede d'utilisation correspondant
RU2171806C2 (ru) Производные n-сульфонилимидазола и их кислотно-аддитивные соли и фунгицидное средство на их основе
GB2245565A (en) Fungicidal heterocyclic compounds
EP0416746A2 (fr) Fongicides contenant un groupe alkoxycarbonylvinyle ou un groupe alkyloxyimino

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP 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 IT LU NL SE

122 Ep: pct application non-entry in european phase