WO1994027969A1 - Derives d'isoquinolinetrione utilises comme herbicides - Google Patents

Derives d'isoquinolinetrione utilises comme herbicides Download PDF

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Publication number
WO1994027969A1
WO1994027969A1 PCT/GB1994/001094 GB9401094W WO9427969A1 WO 1994027969 A1 WO1994027969 A1 WO 1994027969A1 GB 9401094 W GB9401094 W GB 9401094W WO 9427969 A1 WO9427969 A1 WO 9427969A1
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Prior art keywords
compound
optionally substituted
ethyl
preparation
prepared
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PCT/GB1994/001094
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English (en)
Inventor
David John Collins
David Philip John Pearson
Christopher Victor Coles
Glynn Mitchell
Stuart Martin Ridley
Eric Daniel Clarke
Kevin James Gillen
Shaheen Tiffin
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Zeneca Limited
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Priority to AU67274/94A priority Critical patent/AU6727494A/en
Publication of WO1994027969A1 publication Critical patent/WO1994027969A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to herbicidal compositions containing isoquinolinetrione derivatives, to novel herbicidal isoquinolinetrione derivatives, and to processes for their preparation.
  • a herbicidal composition comprising a compound of formula (I), or a salt thereof where
  • R is selected from hydrogen; optionally substituted alkyl; optionally substituted alkoxy; acyloxy; hydroxy; NR 4 R 5 where R 4 and R 5 are
  • Suitable optional substituents for the ring formed by R 2 and R 3 include one or more groups selected from halogen; hydroxy; alkoxy; NR 10 R 11 where R 10 and R 11 are independently selected from hydrogen, alkyl or sulphonyl and R 11 may additionally be acyl; COR 12 where R 12 is hydrogen hydroxy, alkoxy, or optionally substituted alkyl or a group NR 13 R 14 where R 13 and R 14 are independently hydrogen or alkyl, alkenyl or alkynyl any of which may be optionally substituted; optionally substituted phenyl; alkyl; cyano; nitro; haloalkyl; S(O) n R 15 where n is 0, 1 or 2 and R 15 is
  • a particular class of compounds of formula (I) are those of formula
  • R 1 , X, Y and Z are as defined above and R 16 , R 17 , R 18 and R 19 are independently selected from hydrogen or the groups listed above as optional substituents for the fused aromatic carbocyclic or heterocyclic rings, including the case where any adjacent two of R 16 , R 17 , R 18 and R 19 together with the carbon atoms which they are attached form a fused saturated or unsaturated carbocyclic or heterocyclic ring.
  • a herbicidal composition comprising a compound of formula (II), where X, Y and Z are all oxygen, R is selected from hydrogen; optionally substituted alkyl; optionally substituted alkoxy; acyloxy; hydroxy; NR 9 R 10 where R 9 and R 10 are independently hydrogen or alkyl; or optionally substituted aryl; and R 16 , R 17 , R 18 and R 19 are independently selected from hydrogen; halogen; hydroxy; alkoxy; NR 20 R 21 where R 20 and R 21 are independently selected from hydrogen, or alkyl and R 21 may additionally be acyl; COR 22 where R 22 is hydrogen or optionally substituted alkyl or a group OR 23 or NR 23 R 24 where R 23 and R 24 are independently hydrogen or alkyl, alkenyl or alkynyl any of which may be optionally substituted; alkyl; cyano; nitro; haloalkyl; S(O) n R 25 where n is 0, 1 or 2 and R 25 is
  • R 2 and R 3 form a fused optionally substituted furan, thiophene, pyrrole, pyrazole, thiazole, isothiazole, oxazole, imidazole, isoxazole, pyridine, or pyrimidine ring.
  • R 1 , X, Y and Z are as defined above for formula (I)
  • R 26 and R 27 are independently hydrogen or are selected from the groups described above as substituents for the ring formed by R 2 and R 3 , or R 26 and R 27 together form an optionally substituted fused saturated or unsaturated carbocylic or heterocyclic ring.
  • R 26 is preferably hydrogen or phenyl.
  • alkyl includes straight or branched alkyl chains, suitably containing up to 10 carbon atoms, preferably from 1 to 6 carbon atoms.
  • alkenyl and “alkynyl” includes unsaturated straight or branched chain containing up to 10 carbon atoms, preferably from 2 to 6 carbon atoms.
  • alkoxy relates to such an alkyl group linked with an oxygen atom.
  • aryl includes phenyl and naphthyl.
  • acyl includes groups of formula C(O)R 28 where R 28 is optionally substituted alkyl or alkoxy. Examples of acyl include acetyl and methoxy carbonyl.
  • Carbocyclic includes rings of up to 10, preferably up to 7 carbon atoms.
  • heterocyclic includes rings containing up to 10, preferably up to 7 atoms, up to three of which are selected from oxygen, sulphur or nitrogen.
  • halo or “halogen” includes chlorine, fluorine, bromine and iodine.
  • Suitable optional substituents for any alkyl, alkoxyalkyl, alkenyl or alkynyl groups mentioned above include one or more groups selected from halogen such as chloro; hydroxy; nitro; optionally substituted aryl; or
  • R 29 is OR 30 or NR 31 R 32 and R 30 , R 31 , and R 32 are independently selected from hydrogen or alkyl; or P(O)OR 33 OR 34 or
  • Suitable optional substituents for any aryl groups mentioned above include halo, haloalkyl and nitro.
  • R 1 is selected from hydrogen, C 1-6 alkyl or optionally substituted benzyl.
  • R 1 are hydrogen, methyl or ethyl.
  • R 16 , R 17 , R 18 and R 19 suitably are selected from hydrogen, halogen, NR 10 R 11 , CONR 13 N 14 or alkoxy or two of R 2 , R 3 , R 4 and R 5 together form a fused phenyl ring.
  • R 16 , R 17 , R 18 and R 19 are hydrogen, amino, hydroxy, acetamido.
  • R 16 , R 17 , R 18 and R 19 are all hydrogen.
  • R 16 , R 17 , R 18 or R 19 is a salt or ester of carboxy, it is suitably an agriculturally acceptable salt or ester.
  • agriculturally acceptable salts include sodium, potassium or calcium salts, sulphonium or sulphoxonium salts such as those of formula
  • R 35 R 36 R 37 where q is 0 or 1, or ammonium or quaternary ammonium ions of formula N + R 35 R 36 R 37 R 38 where R 35 , R 36 , R 37 and R 38 are independently selected from optionally substituted alkyl, alkenyl, alkynyl, or aryl groups.
  • Examples of agriculturally acceptable esters include optionally substituted alkyl, alkenyl, alkynyl, or aryl esters.
  • salts of compounds containing a carboxyl group has been referred to above.
  • the compound of formula (I) contains a basic group (e.g. an NH 2 group, or a tertiary amine group such as that present when the groups R 2 and R 3 together form a thiazole, imidazole, or oxazole ring)
  • a basic group e.g. an NH 2 group, or a tertiary amine group such as that present when the groups R 2 and R 3 together form a thiazole, imidazole, or oxazole ring
  • Such salts may be prepared from acids having agriculturally acceptable anions, for examples sulphuric, hydrochloric, or phosphoric acid.
  • the invention covers all individual isomers as well as mixtures thereof in all proportions.
  • the invention also covers all tautomers.
  • the oxidation may be carried out, for example, by condensing a compound (IV) with dimethyl p-nitrosoaniline followed by treatment with an acid such as dilute hydrochloric acid or sulphuric acid or other inorganic acids.
  • the reaction may be effected in an organic solvent such as ethanol, methanol or isopropanol at moderate temperatures of from 10 to 50°C, conveniently at ambient temperature.
  • the oxidation may be carried out using a strong oxidising agent such as sodium dichromate.
  • the reaction may be effected in an acidic solvent such as aqueous sulphuric acid or glacial acetic acid, preferably a combination of both, at temperatures of from 0°C to 80°C, conveniently at ambient temperature.
  • the reaction may be effected by heating the compound (V) to a temperature of from 100 to 250°C, either alone or in the presence of an inert solvent such as toluene, xylene or diphenyl ether.
  • an inert solvent such as toluene, xylene or diphenyl ether.
  • the reaction may be effected in a protonic solvent such as water or an alkanol for example ethanol, at temperatures of from 10 to 110°C.
  • a protonic solvent such as water or an alkanol for example ethanol
  • Compounds of formula (VI) can be prepared by reacting a compound of formula (VIII), where R 2 , and R 3 are as defined in relation to formula (I) with acetic anhydride.
  • the reaction may be effected by heating the compound (VIII) in an excess of acetic anhydride as solvent, to a
  • compounds of formula (IV) can be prepared by reacting a compound of formula (VIII) as hereinbefore defined with a compound of formula (VII) as hereinbefore defined.
  • the reaction may be effected at elevated temperatures e.g. temperatures of from 80 to 100°C in the presence of a protonic solvent, such as water.
  • Compounds of formula (VII) are known compounds or can be prepared from known compounds by conventional methods.
  • Compounds of formula (VIII) may be prepared by reacting a compound of formula (IX), where R 2 and R 3 are as defined in relation to formula (I), with a base such as potassium hydroxide or sodium hydroxide in water.
  • a base such as potassium hydroxide or sodium hydroxide in water.
  • the reaction can be carried out at temperatures of from 10°C to 100°C, conveniently at ambient temperature.
  • Compounds of formula (IX) can be prepared by reacting a compound of formula (X), where R 2 , and R 3 are as defined in relation to formula (I), with an alkyl acetoacetate such as ethyl acetoacetate in the presence of a copper (I) species such as cuprous bromide and a strong base such as sodium hydride.
  • the reaction is preferably carried out at temperatures from 70°C to 90°C, using an excess of ethyl acetoacetate as solvent.
  • Compounds of formula (X) are known compounds or can be prepared from known compounds by conventional methods.
  • Compounds of formula (XI) are known compounds or can be prepared from known compounds by conventional methods.
  • compounds of formula (XI) can be prepared by reacting a compound of formula (XII), where R 2 and R 3 are as defined in relation to formula (I), with a source of cyanide ion, preferably potassium cyanide, in the absence of a solvent.
  • the reaction can be conducted at temperatures of from 180°C to 250°C, preferably at 190°C to 210°C.
  • Compounds of formula (I) where X, Y and Z are oxygen may also be prepared by reacting a compound of formula (XIII), where R 2 , and R 3 are as defined in relation to formula (I); with a compound of formula (XIV); where X 1 and X 2 are leaving groups.
  • the ring formed by the groups R 2 , and R 3 include at least some electron-donating groups such as alkoxy in particular methoxy, or alternatively the ring formed by the groups R 2 and R 2 is an electron rich heterocycle such as furan, pyrrole or thiophene.
  • the leaving groups X 1 and X 2 are preferably halogen, mesylate or tosylate.
  • halogen atoms such as chlorine
  • the reaction may be effected at a temperature of from 60 to 180°C in a solvent selected from orthodichlorobenzene, toluene, or xylene, or by heating in the absence of a solvent.
  • Compounds of formula (XIII) may be prepared by reacting a compound of formula (XV), where R 2 , and R 3 are as defined above and R 40 is a halide, with a compound of formula (VII) as hereinbefore defined.
  • the reaction may be effected at moderate temperatures of from 0 to 100°C, in a range of solvents such as water, or in the absence of a solvent.
  • R 40 is chloride
  • the reaction may be effected using a halogenating agent such as thionyl chloride, phosphoryl chloride or phosphorus pentachloride at temperatures of from 20 to 120oC.
  • a halogenating agent such as thionyl chloride, phosphoryl chloride or phosphorus pentachloride at temperatures of from 20 to 120oC.
  • the oxidation is suitably effected using an oxidising agent such as chromium trioxide or sodium dichromate.
  • the reaction can be effected at temperatures of from 0 to 50°C using an aqueous inorganic acid, preferably sulphuric acid and/or an organic acid, such as glacial acetic acid as solvent.
  • Compounds of formula (XVII) can be prepared by oxidation of compounds of formula (XVIII) where R 1 , R 2 , and R 3 are as defined in relation to formula (I) and m- is an anion. Suitable values for m- include halides such as iodides or chlorides, or sulphonates such as para toluene sulphonate.
  • the oxidation can be effected using an oxidising agent such as potassium ferricyanide.
  • Reaction conditions are suitably low temperatures of from -20 to +30°C in a solvent such as water, in the presence of a base, such as sodium or potassium hydroxide.
  • Compounds of formula (XVIII) can be prepared by reacting a compound of formula (XIX); where R 2 , and R 3 are as hereinbefore defined with a compound of formula (XX); where R 1 and m are as hereinbefore defined, in the presence of a base.
  • Compounds of formula (I) where X, Y and Z are oxygen and R 1 is an acyloxy group can be prepared by heating a compound of formula (XXI), where R 2 and R 3 are as defined in relation to formula (I), with an acyl halide such as acetyl chloride.
  • the reaction is suitably carried out at temperatures of from 20°C to 120°C, preferably at 60°C to 80°C.
  • substituent R 18 is cyano may be prepared by nitrating a compound (V)
  • the acid (XXII) is converted to the corresponding acid chloride by treatment with a conventional chlorinating agent (e.q. SOCl 2' POCl 3 ) and then into the corresponding amide (XXIII) by reaction with an amine R 1 NH 2 ⁇
  • a conventional chlorinating agent e.q. SOCl 2' POCl 3
  • a amide (XXIII) by reaction with an amine R 1 NH 2 ⁇
  • the amide (XXIII) is then heated with oxalyl chloride to a moderate temperature (e.g. 50-140°C) either with a solvent (e.g. CCl 4 or
  • hydroxylamine salt e.g. the hydrochloride
  • a solvent e.g. ethanol
  • a base e.g. sodium hydride
  • aprotic solvent e.g. dimethyl formamide
  • a dialkyl sulphate e.g. dimethyl sulphate
  • a base e.g. potassium carbonate
  • oximes e.g. the hydrochloride
  • a solvent e.g. ethanol
  • a solvent e.g. dichloromethane
  • a solvent e.g . dichloromethane
  • a base is a secondary amine (e.g. piperidine).
  • an acid e.g. HCl
  • a solvent e.g. a mixture of methanol and water
  • Compounds containing a quaternary nitrogen atom may be prepared for example by reaction of the corresponding heterocycle with an alkyl halide, preferably a bromide or iodide (e.g. methyl or ethyl bromide or iodide).
  • an alkyl halide preferably a bromide or iodide (e.g. methyl or ethyl bromide or iodide).
  • compound 136 may be made by reaction of methyl iodide with compound 134.
  • phenylimino group e.g. a 2-methylphenylimino group
  • X and Z are oxygen
  • a compound of formula (XXIV) with a suitably substituted nitrosobenzene, preferably in a solvent (e.g.
  • compositions containing compounds of formula (I) include both dilute compositions, which are ready for immediate use, and concentrated
  • compositions which require to be diluted before use, usually with water.
  • the compositions contain from 0.01% to 90% by weight of the active ingredient.
  • Dilute compositions ready for use preferably contain from 0.01% to 2% of active ingredient, while concentrated compositions may contain from 20% to 90% of active ingredient, although from 20% to 70% is usually preferred.
  • the solid compositions may be in the form of granules, or dusting powders wherein the active ingredient is mixed with a finely divided solid diluent, e.g. kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth and gypsum. They may also be in the form of dispersible powders or grains, comprising a wetting agent to facilitate the dispersion of the powder or grains in liquid. Solid compositions in the form of a powder may be applied as foliar dusts.
  • a finely divided solid diluent e.g. kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth and gypsum.
  • a finely divided solid diluent e.g. kaolin, bentonite, kieselguhr, dolomite
  • Liquid compositions may comprise a solution or dispersion of an active ingredient in water optionally containing a surface-active agent, or may comprise a solution or dispersion of an active ingredient in a
  • Surface-active agents may be of the cationic, anionic, or non-ionic type or mixtures thereof.
  • the cationic agents are, for example, quaternary ammonium compounds (e.g. cetyltrimethylammonium bromide).
  • Suitable anionic agents are soaps; salts of aliphatic mono ester of sulphuric acid, for example sodium lauryl sulphate; and salts of sulphonated aromatic
  • non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkylphenols such as octyl- or nonyl- phenol (e.g. Agral 90) or
  • non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitan monolaurate; the condensation products of the partial ester with ethylene oxide; the lecithins; and silicone surface active agents (water soluble surface active agents having a skeleton which comprises a siloxane chain e.g. Silwet L77).
  • a suitable mixture in mineral oil is Atplus 411F.
  • aqueous solutions or dispersions may be prepared by dissolving the active ingredient in water or an organic solvent optionally containing wetting or dispersing agent(s) and then, when organic solvents are used, adding the mixture so obtained to water optionally containing wetting or dispersing agent(s).
  • organic solvents include, for example, ethylene di-chloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes and
  • dispersions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, and the concentrate is then diluted with water before use.
  • the concentrates are usually required to withstand storage for prolonged periods and after such storage, to be capable of dilution with water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by
  • Concentrates conveniently contain 20-90%, preferably 20-70%, by weight of the active ingredient(s).
  • Dilute preparations ready for use may contain varying amounts of the active ingredient(s) depending upon the intended purpose; amounts of 0.01% to 10.0% and preferably 0.1% to 2%, by weight of active ingredient(s) are normally used.
  • a preferred form of concentrated composition comprising the active ingredient which has been finely divided and which has been dispersed in water in the presence of a surface-active agent and a suspending agent.
  • Suitable suspending agents are hydrophilic colloids and include, for example, polyvinylpyrrolidone and sodium carboxymethylcellulose, and the vegetable gums, for example gum acacia and gum tragacanth.
  • Preferred suspending agents are those which impart thixotropic properties to, and increase the viscosity of the concentrate. Examples of preferred
  • suspending agents include hydrated colloidal mineral silicates, such as montmorillonite, beidellite, nontronite, hectorite, saponite, and
  • suspending agents include cellulose derivatives and polyvinyl alcohol.
  • the compounds of formula (I) are active as herbicides and therefore, in a further aspect the invention provides a process for severely damaging or killing unwanted plants which process comprises applying to the plants, or to the growth medium of the plants, a herbicidally effective amount of a compound of formula (I) as hereinbefore defined.
  • the compounds of formula (I) are active against a broad range of weed species including monocotyledonous and dicotyledonous species.
  • the compounds of formula (I) may be applied directly to the plant (post-emergence application) or to the soil before the emergence of the plant (pre-emergence application). They are particularly useful when applied post-emergence.
  • the rate of application of the compounds of the invention will depend on a number of factors including, for example, the compound chosen for use, the identity of the plants whose growth is to be inhibited, the
  • formulations selected for use and whether the compound is to be applied for foliage or root uptake As a general guide, however, an application rate of from 0.001 to 20 kilograms per hectare is suitable while from 0.025 to 10 kilograms per hectare may be preferred.
  • compositions of the invention may comprise, in addition to one or more compounds of the invention, one or more compounds not of the invention but which possess biological activity for example herbicides, fungicides, insecticides (optionally with an insecticide synergist) and plant growth regulators.
  • the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound of formula (I) as hereinbefore defined with at least one other herbicide.
  • the other herbicide may be any herbicide not having the formula (I). It will generally be a herbicide having a complementary action in the particular application.
  • Examples of useful complementary herbicides include:
  • B. hormone herbicides particularly the phenoxy alkanoic acids such as MCPA, MCPA-thioethyl, dichlorprop, 2,4,5-T, MCPB, 2,4-D, 2,4-DB, mecoprop, trichlopyr, clopyralid, and their derivatives (eg. salts, esters and amides);
  • dinitroaniline herbicides such as dinitramine, trifluralin,
  • arylurea herbicides such as diuron, flumeturon, metoxuron,
  • neburon isoproturon, chlorotoluron, chloroxuron, linuron, monolinuron, chlorobromuron, daimuron, methabenzthiazuron;
  • J. triazine herbicides such as atrazine, simazine, aziprotryne, cyanazine, prometryn, dimethametryn, simetryne, and terbutryn
  • K. phosphorothioate herbicides such as piperophos, bensulide, and butamifos
  • L. thiolcarbamate herbicides such as cycloate, vernolate, molinate, thiobencarb, butylate , EPTC , tri-allate, di-allate, esprocarb, tiocarbazil, pyridate, and dimepiperate;
  • N. benzoic acid herbicides such as 2,3,6-TBA, dicamba and
  • O. anilide herbicides such as pretilachlor, butachlor, alachlor, propachlor, propanil, metazachlor, metolachlor, acetochlor, and dimethachlor;
  • P. dihalobenzonitrile herbicides such as dichlobenil, bromoxynil and ioxynil;
  • Q. haloalkanoic herbicides such as dalapon, TCA and salts thereof;
  • R. diphenylether herbicides such as lactofen, fluroglycofen or
  • S. phenoxyphenoxypropionate herbicides such as diclofop and esters thereof such as the methyl ester, fluazifop and esters thereof, haloxyfop and esters thereof, quizalofop and esters thereof and fenoxaprop and esters thereof such as the ethyl ester;
  • T. cyclohexanedione herbicides such as alloxydim and salts thereof, sethoxydim, cycloxyidim, tralkoxydim, and clethodim;
  • U. sulfonyl urea herbicides such as chlorosulfuron, sulfometuron, metsulfuron and esters thereof; benzsulfuron and esters thereof such as DPX-M6313, chlorimuron and esters such as the ethyl ester thereof pirimisulfuron and esters such as the methyl ester thereof, 2-[3-(4-methoxy-6-methy1-1,3,5- triazin-zyl)-3-methylureidosulphonyl) benzoic acid esters such as the methyl ester thereof (DPX-LS300) and pyrazosulfuron;
  • V. imidazolidinone herbicides such as imazaquin, imazamethabenz, imazapyr and isopropylammonium salts thereof, imazethapyr;
  • X. amino acid herbicides such as glyphosate and glufosinate and their salts and esters, sulphosate and bialaphos;
  • Y. organoarsenical herbicides such as monosodium methanearsonate
  • herbicidal amide derivative such as napropamide, propyzamide, carbetamide, tebutam, bromobutide, isoxaben, naproanilide and naptalam;
  • miscellaneous herbicides including ethofumesate, cinmethylin, difenzoquat and salts thereof such as the methyl sulphate salt, clomazone, oxadiazon, bromofenoxim, barban, tridiphane, flurochloridone, quinclorac, dithiopyr and mefanacet;
  • Examples of useful contact herbicides include:
  • bipyridylium herbicides such as those in which the active entity is paraquat and those in which the active entity is diquat;
  • CC. triketone herbicides such as sulcotrione.
  • EXAMPLE 23 PREPARATION OF COMPOUND 23 A stirred solution of N-ethyl-5-nitroisoquinolin-1,3,4-trione (prepared as described in Example 17 above) (0.200g) in ethanol (10ml) was treated with iron powder (0.135g) followed by concentrated hydrochloric acid (0.5ml).
  • the reaction mixture was heated under reflux for 3 hours, then cooled and filtered through a plug of hyflo to remove the iron residues (the hyflo plug was washed through with ethyl acetate).
  • the combined filtrates were evaporated to dryness in vacuo, and the residue was purified by
  • EXAMPLE 30 PREPARATION OF COMPOUND 30 By a method similar to that described in Example 1 but using N-n-butyl homophthalimide (prepared as described in Preparative Example 26 below)
  • example compound 38A (eluting with ethyl acetate/hexane mixtures) to afford firstly a further quantity of example compound 38A (5mg), followed by example compound 38B, which was obtained as a red solid, yield 2mg.
  • Example 41 (0.010g) in acetic acid (1ml) was treated with a solution of sodium dichromate (0.050g) in 2M sulphuric acid (1ml). The mixture was stirred for 3 hours, then water was added and the mixture was extracted with ethyl acetate. The extract was dried (MgSO 4 ) and evaporated in vacuo. The residue was passed through a silica-gel plug, eluting with ethyl acetate/hexane (1:3), and the filtrate was evaporated in vacuo to leave the title compound, yield 0.008g.
  • EXAMPLE 206 PREPARATION OF COMPOUNDS 206A AND 206B
  • EXAMPLE 207 PREPARATION OF COMPOUNDS 207A AND 207B
  • EXAMPLE 208 PREPARATION OF COMPOUNDS 208A AND 208B
  • EXAMPLE 210 PREPARATION OF COMPOUNDS 210A AND 210B
  • EXAMPLE 211 PREPARATION OF COMPOUNDS 211A AND 211B
  • 3-Carboxynaphthalene-2-acetonitrile (prepared as described in step 2 above) (3.50g) was added to a solution of potassium hydroxide (7.00g) in water (30ml). The dark solution was heated under reflux for 136 minutes, when no more ammonia was evolved. The brown solution was cooled and filtered to remove a trace of insoluble material, then acidified to pHl using 6M hydrochloric acid. The crystalline precipitate was filtered off, washed and dried to afford the product, yield 3.24g.
  • This compound was prepared by a method similar to that described in
  • This compound was prepared by a method similar to that described in
  • reaction mixture was extracted with ethyl acetate (x3), and the combined extracts were washed with saturated sodium bicarbonate solution
  • Example 19 Step 1 above) (0.200g), triethylamine (0.118g) and butyryl chloride (0.124g), and purifying the crude product by chromatography on silica gel (eluting with ethyl acetate/hexane 1:1), the title compound was obtained as a white solid, yield 0.202g.
  • Step 4 Preparation of 2-carboxy-4-cyano-N-ethyl phenylacetamide A stirred solution of 4-amino-2-carboxy-N-ethyl phenylacetamide (prepared as in step 3 above) (2.44g) in 6M hydrochloric acid (20ml) was cooled to
  • Tween 20 is a Trade Mark for a surface-active agent comprising a condensate of 20 molar proportions of ethylene oxide with sorbitan laurate.
  • Span 80 is a Trade Mark for a surface-active agent comprising sorbitan mono-laurate.
  • the volume was made up to 5cm 3 with water, glass beads were added and this mixture was then shaken to effect dissolution or suspension of the chemical, after which the beads were removed. In all cases, the mixture was then diluted with water to the required spray volume. If sprayed independently, volumes of 25cm 3 and 30cm 3 were required for pre-emergence and post-emergence tests respectively; if sprayed together, 45cm 3 was required.
  • the sprayed aqueous emulsion contained 4% of the initial solvent/surfactant mix and the test chemical at an appropriate concentration.
  • the spray compositions so prepared were sprayed onto young pot plants (post-emergence test) at a spray volume equivalent to 400 litres per hectare. Damage to plants was assessed 13 days after spraying by
  • seeds were placed on the surface of plastic trays of compost in the case of tests carried out on Compounds Nos. 1-3, or crop seeds were sown at 2 cm depth (i.e. sugar beet, cotton, rape, winter wheat, maize, rice, soya) and weed seeds at 1 cm depth beneath compost, for the remainder. They were then sprayed with the compositions at a spray volume equivalent to 400 litres per hectare. 20 days after spraying, the seedlings in the sprayed plastic trays were compared with the seedlings in unsprayed control trays, the damage being assessed on the same scale of 0 to 9.
  • Table VI below gives the results of further tests.
  • the compounds were formulated as previously described and diluted to a volume of 10ml.
  • the compositions so prepared were sprayed on to the test plants and seeds at a spray volume of 1000 litres per hectare.

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

Abstract

L'invention concerne une composition herbicide comprenant un composé de la formule (I) ou un sel de celui-ci, formule dans laquelle R1 est sélectionné parmi hydrogène; alkyle éventuellement substitué; alcoxy éventuellement substitué; acyloxy; hydroxy; NR?4R5 où R4 et R5¿ représentent indépendamment hydrogène ou alkyle; ou aryle éventuellement substitué; R2 et R3 forment, réunis, un noyau aromatique carbocyclique ou hétérocyclique, condensé, pentagonal ou hexagonal, éventuellement substitué; et X, Y et Z sont indépendamment sélectionnés parmi = C(CN)¿2?, NOH, NOR?6, NNR7R8¿, NCN ou NR?9, où R6, R7 et R8¿ sont indépendamment sélectionnés parmi hydrogène, alkyle éventuellement substitué, alcényle éventuellement substitué et alcynyle éventuellement substitué, et R9 représente phényle éventuellement substitué; en combinaison avec un excipient ou un diluant.
PCT/GB1994/001094 1993-05-24 1994-05-20 Derives d'isoquinolinetrione utilises comme herbicides WO1994027969A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU67274/94A AU6727494A (en) 1993-05-24 1994-05-20 Isoquinolinetrione derivatives as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB939310700A GB9310700D0 (en) 1993-05-24 1993-05-24 Novel composition
GB9310700.1 1993-05-24

Publications (1)

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WO1994027969A1 true WO1994027969A1 (fr) 1994-12-08

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AU (1) AU6727494A (fr)
GB (1) GB9310700D0 (fr)
WO (1) WO1994027969A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1193257A2 (fr) * 1994-12-29 2002-04-03 The Regents Of The University Of California Composés pour la transduction de signaux à médiation par la céramide
US7714134B2 (en) 2004-06-11 2010-05-11 4Sc Ag Compounds and use of tetrahydropyridothiophenes
US7714136B2 (en) 2005-05-25 2010-05-11 4Sc Ag Tetrahydropyridothiophenes
US7714135B2 (en) 2005-02-09 2010-05-11 4Sc Ag Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer
US7723523B2 (en) 2004-05-28 2010-05-25 4Sc Ag Tetrahydropyridothiophenes
US7741488B2 (en) 2005-02-11 2010-06-22 4Sc Ag Tetrahydropyridothiophenes as antiproliferative agents for the treatment of cancer
US7763728B2 (en) 2005-05-25 2010-07-27 4Sc Ag Tetrahydropyridothiophenes
US7902179B2 (en) * 2001-04-26 2011-03-08 Ajinomoto Co., Inc. Heterocyclic compounds
US8779144B2 (en) 2006-03-16 2014-07-15 Evotec (Us) Inc. Bicycloheteroaryl compounds as P2X7 modulators and uses thereof
JP2014520776A (ja) * 2011-07-04 2014-08-25 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用
CN106674108A (zh) * 2016-11-09 2017-05-17 苏州大学 3－亚氨基异喹啉－1，4－二酮衍生物的制备方法
WO2020102245A1 (fr) 2018-11-12 2020-05-22 University Of Virginia Patent Foundation Photooxygénation en flux d'aminothienopyridinones générant de nouveaux inhibiteurs de phosphatase ptp4a3
JP2021527125A (ja) * 2018-06-07 2021-10-11 ディサーム・セラピューティクス・インコーポレイテッドＤｉｓａｒｍ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． Ｓａｒｍ１阻害剤
US11655237B2 (en) 2020-03-30 2023-05-23 Gilead Sciences, Inc. Solid forms of a Cot inhibitor compound
US11827662B2 (en) 2019-06-14 2023-11-28 Gilead Sciences, Inc. Cot modulators and methods of use thereof
US11845737B2 (en) 2020-04-02 2023-12-19 Gilead Sciences, Inc. Process for preparing a Cot inhibitor compound
US11905299B2 (en) 2015-07-06 2024-02-20 Gilead Sciences, Inc. Cot modulators and methods of use thereof

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1193257A2 (fr) * 1994-12-29 2002-04-03 The Regents Of The University Of California Composés pour la transduction de signaux à médiation par la céramide
EP1193257A3 (fr) * 1994-12-29 2002-06-26 The Regents Of The University Of California Composés pour la transduction de signaux à médiation par la céramide
US7902179B2 (en) * 2001-04-26 2011-03-08 Ajinomoto Co., Inc. Heterocyclic compounds
US7723523B2 (en) 2004-05-28 2010-05-25 4Sc Ag Tetrahydropyridothiophenes
US7803945B2 (en) 2004-05-28 2010-09-28 4Sc Ag Tetrahydropyridothiophenes
US7714134B2 (en) 2004-06-11 2010-05-11 4Sc Ag Compounds and use of tetrahydropyridothiophenes
US7714135B2 (en) 2005-02-09 2010-05-11 4Sc Ag Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer
US7741488B2 (en) 2005-02-11 2010-06-22 4Sc Ag Tetrahydropyridothiophenes as antiproliferative agents for the treatment of cancer
US7714136B2 (en) 2005-05-25 2010-05-11 4Sc Ag Tetrahydropyridothiophenes
US7763728B2 (en) 2005-05-25 2010-07-27 4Sc Ag Tetrahydropyridothiophenes
US8779144B2 (en) 2006-03-16 2014-07-15 Evotec (Us) Inc. Bicycloheteroaryl compounds as P2X7 modulators and uses thereof
JP2014520776A (ja) * 2011-07-04 2014-08-25 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用
US11905299B2 (en) 2015-07-06 2024-02-20 Gilead Sciences, Inc. Cot modulators and methods of use thereof
CN106674108A (zh) * 2016-11-09 2017-05-17 苏州大学 3－亚氨基异喹啉－1，4－二酮衍生物的制备方法
CN106674108B (zh) * 2016-11-09 2019-01-01 苏州大学 3－亚氨基异喹啉－1，4－二酮衍生物的制备方法
JP2021527125A (ja) * 2018-06-07 2021-10-11 ディサーム・セラピューティクス・インコーポレイテッドＤｉｓａｒｍ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． Ｓａｒｍ１阻害剤
WO2020102245A1 (fr) 2018-11-12 2020-05-22 University Of Virginia Patent Foundation Photooxygénation en flux d'aminothienopyridinones générant de nouveaux inhibiteurs de phosphatase ptp4a3
WO2020102243A2 (fr) 2018-11-12 2020-05-22 University Of Virginia Patent Foundation Photooxygénation à écoulement entrant d'aminothiénopyridinones produisant de nouveaux inhibiteurs de phosphatase ptp4a3
US11827662B2 (en) 2019-06-14 2023-11-28 Gilead Sciences, Inc. Cot modulators and methods of use thereof
US11655237B2 (en) 2020-03-30 2023-05-23 Gilead Sciences, Inc. Solid forms of a Cot inhibitor compound
US11845737B2 (en) 2020-04-02 2023-12-19 Gilead Sciences, Inc. Process for preparing a Cot inhibitor compound

Also Published As

Publication number Publication date
AU6727494A (en) 1994-12-20
GB9310700D0 (en) 1993-07-07

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